CRUDE BIOGLYCERIN

This application claims priority to U.S. Serial No. 13/348,777, entitled METHOD OF BIOBASED CHEMICAL PRODUCTION FROM CRUDE BIOGLYCERIN OF PLANT ORIGIN, filed January 12, 2012, U.S. Serial No. 13/348,785, entitled METHOD OF

BIOBASED CHEMICAL PRODUCTION FROM CRUDE BIOGLYCERIN OF ANIMAL ORIGIN, filed January 12, 2012, U.S. Serial No. 13/348,794, entitled METHOD OF

BIOBASED CHEMICAL PRODUCTION FROM CRUDE BIOGLYCERIN OF RECYCLED OIL, GREASE, AND FAT ORIGIN, filed January 12, 2012. All of the forgoing patent applications are incorporated herein by reference.

I. Background

A. Field

[0001] The present invention is directed generally to a method of production of value- added, biobased chemicals, derivative products, and purified glycerin from bioglycerin. A method of purification of a crude bioglycerin is described herein, which provides methods for desalinating, decolorizing, and concentrating bioglycerin for the production of biobased chemicals, derivative products, and purified glycerin.

B. Description of the Related Art

[0002] The world currently faces depletion of fossil fuels while demands for these fuels are ever increasing. Petrochemicals provide an energy source and a component of the majority of raw materials used in many industries. In fact, approximately 95% of all chemicals manufactured today are derived from petroleum. However, this heavy reliance upon fossil fuels is creating harm to the environment. The burning of these fossil fuels has led to the pollution of air, water and land, as well as global warming and climate changes. Through the use of fossil fuels, the environment has been harmed, perhaps irreparably, in an effort to meet the nearly insatiable demand for energy and manufactured products. Fossil fuels are a finite natural resource, with the depletion of readily available oil reserves across the globe; the supply chain has shifted to more complex and environmentally risky production technologies. A reduction and conservation of fossil fuels is clearly needed. Some alternatives to fossil fuels, like solar power, wind power, geothermal power, hydropower, and nuclear power, are used to a degree. However, a more efficient use of renewable resources is always being sought.

[0003] In particular, biofuels, which come from a renewable, carbonaceous source, are targeted to become one of these more efficient resources. In the demand for fossil fuels, biodiesel, a type of biofuel, has emerged as a potentially inexhaustible alternative to petroleum diesel, particularly during an oil crisis, a surge in crude oil prices, and/or political unrest in the oil producing regions of the world. This renewable and clean-burning diesel replacement can reduce our dependence on foreign petroleum and create new employment within the green industry.

II. Summary

[0004] This Summary is provided to introduce a selection of concepts in a simplified form that are further described below in the Detailed Description. This Summary is not intended to identify key factors or essential features of the claimed subject matter, nor is it intended to be used to limit the scope of the claimed subject matter.

[0005] Accordingly, described herein is a method for biorefining. It may include the steps of providing bioglycerin, treating the bioglycerin to provide treated bioglycerin, and producing at least one derivative product from at least one of bioglycerin and treated bioglycerin.

[0006] In one implementation, the method further comprises the step of providing bioglycerin as a by-product of biodiesel production. [0007] In another implementation, bioglycerin is provided from at least one bioglycerin of plant-based bioglycerin, animal-based bioglycerin, and bioglycerin of recycled oil, grease, and fat origin.

[0008] In still another implementation, plant-based bioglycerin is provided from at least one plant-based triglyceride of soybean oil, corn oil, cottonseed oil, canola oil, rice bran oil, flax oil, sunflower oil, safflower oil, artichoke oil, sesame oil, peanut oil, castor oil, coconut oil, colza oil, false flax oil, hemp oil, mustard oil, palm oil, radish oil, rapeseed oil, tigernut oil, tung oil, copaiba oil, jatropha oil, jojoba oil, karanj oil, milk bush (pencil bush) oil, neem oil, olive oil, salicornia oil, and paradise oil.

[0009] In yet another implementation, animal-based bioglycerin is provided from at least one animal-based triglyceride of meat, meat by-products, animal fats, animal tallow, choice white grease, yellow grease, lard, fish, fish by-products, fish oil, milk, milk fat, butter fat, and eggs.

[0010] In still yet another implementation, animal-based bioglycerin is provided from at least one animal-based triglyceride of cattle, pigs, boar, sheep, horses, rabbits, deer, antelope, bison, ox, chickens, turkeys, geese, ducks, quail, ostrich, elk, emu, whales, sharks, dolphins, fish, clams, and mussels.

[0011] In one implementation, bioglycerin from at least one recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one triglyceride of recycled plant-based oil, recycled plant-based fat, recycled plant-based grease, recycled plant- based butter, recycled plant-based margarine, recycled plant-based lard, and recycled plant-based shortening.

[0012] In another implementation, the recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one product of recycled soybean oil, recycled corn oil, recycled cottonseed oil, recycled canola oil, recycled rice bran oil, recycled flax oil, recycled sunflower oil, recycled safflower oil, recycled artichoke oil, recycled sesame oil, recycled peanut oil, recycled castor oil, recycled coconut oil, recycled colza oil, recycled false flax oil, recycled hemp oil, recycled mustard oil, recycled palm oil, recycled radish oil, recycled rapeseed oil, recycled tigernut oil, recycled tung oil, recycled copaiba oil, recycled jatropha oil, recycled jojoba oil, recycled karanj oil, recycled milk bush (pencil bush) oil, recycled neem oil, recycled olive oil, recycled salicornia oil, and recycled paradise oil.

[0013] In still another implementation, bioglycerin from at least one recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one triglyceride of recycled animal-based oil, recycled animal-based fat, recycled animal-based grease, recycled animal-based butter, recycled animal-based margarine, recycled animal-based lard, recycled animal-based shortening, trap grease, and brown grease.

[0014] In yet another implementation, the recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one source of recycled meat, recycled meat byproducts, recycled animal fat, recycled animal tallow, recycled choice white grease, recycled yellow grease, recycled lard, recycled fish, recycled fish by-products, recycled milk, and recycled eggs.

[0015] In still yet another implementation, the recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one source of cattle, pigs, boar, sheep, lambs, horses, rabbits, deer, antelope, bison, ox, chickens, turkeys, geese, ducks, quail, ostrich, elk, emu, whales, sharks, dolphins, fish, clams, and mussels.

[0016] In one implementation, the bioglycerin from at least one recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one recycled triglyceride of residences, restaurants, cafeterias, schools, hotels, camps, hospitals, food preparation facilities, food processing facilities, other food-based businesses, Tenderers, and commercial, industrial, and municipal waste treatment facilities. [0017] In another implementation, the step of treating the bioglycerin to provide treated bioglycerin comprises at least one treatment of desalination treatment, decolorization treatment, and concentration treatment.

[0018] In still another implementation, the desalination treatment provides desalinated bioglycerin as treated bioglycerin.

[0019] In yet another implementation, the decolorization treatment provides decolorized bioglycerin as treated bioglycerin.

[0020] In still yet another implementation, the concentration treatment provides concentrated bioglycerin as treated bioglycerin.

[0021] In one implementation, treating bioglycerin to provide desalinated bioglycerin further comprises the step of utilizing a desalination treatment.

[0022] In yet another implementation, the method further comprises recovering salt.

[0023] In another implementation, the method further comprises the step of lowering a freezing point of an aqueous solution with salt.

[0024] In still another implementation, the step of treating bioglycerin to provide desalinated bioglycerin further comprises the step of adding a solvent.

[0025] In still yet another implementation, the step of treating bioglycerin to provide desalinated bioglycerin further comprises the step of utilizing an ion exchange treatment.

[0026] In one implementation, performing the ion exchange treatment under a batch condition. [0027] In another implementation, performing the ion exchange treatment under a continuous flow condition.

[0028] In still another implementation, the ion exchange treatment further comprises the steps of recovering water during the ion exchange treatment and recycling the water during the ion exchange treatment.

[0029] In yet another implementation, the ion exchange treatment further comprises the steps of recovering a solvent during the ion exchange treatment and recycling the solvent during the ion exchange treatment.

[0030] In still yet another implementation, the ion exchange treatment further comprises the steps of regenerating an ion exchange resin during the ion exchange treatment and recycling the ion exchange resin during the ion exchange treatment.

[0031] In one implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of utilizing a decolorization treatment.

[0032] In another implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of adding a solvent.

[0033] In still another implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of utilizing activated charcoal in the decolorization treatment.

[0034] In yet another implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of recovering a solvent during the

decolorization treatment and recycling the solvent during the decolorization treatment. [0035] In still yet another implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of performing the decolorization treatment under a batch condition or a continuous flow condition.

[0036] In one implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of recovering a solvent during the decolorization treatment with the activated charcoal and recycling the solvent during the decolorization treatment with the activated charcoal.

[0037] In another implementation, the step of treating bioglycerin to provide decolorized bioglycerin further comprises the step of regenerating the activated charcoal during the decolorization treatment and recycling the activated charcoal during the decolorization treatment.

[0038] In still another implementation, the step of treating bioglycerin to provide concentrated bioglycerin further comprises the step of utilizing a concentration treatment.

[0039] In yet another implementation, the step of treating bioglycerin to provide concentrated bioglycerin further comprises the step of utilizing an evaporation or distillation process during the concentration treatment.

[0040] In still yet another implementation, the method further comprises the steps of: recovering water during the concentration treatment and recycling the water during the concentration treatment.

[0041] In one implementation, the method further comprises the steps of: recovering a solvent during the concentration treatment and recycling the solvent during the concentration treatment.

[0042] In another implementation, the method further comprises the step of performing the concentration treatment under a batch condition or a continuous flow condition. [0043] In still another implementation, the bioglycerin has a weight, the treated bioglycerin has a weight, and the weight of treated bioglycerin is greater than about 60% of the weight of bioglycerin.

[0044] In yet another implementation, the bioglycerin has a weight, the treated bioglycerin has a weight, and the weight of treated bioglycerin is greater than about 80% of the weight of bioglycerin.

[0045] In still yet another implementation, the bioglycerin has a weight, the treated bioglycerin has a weight, and the weight of treated bioglycerin is greater than about 90% of the weight of bioglycerin.

[0046] In one implementation, the method further comprises the step of selectively producing the derivative product from the bioglycerin and the treated bioglycerin.

[0047] In another implementation, producing at least one derivative product comprising at least one chemical of commodity chemicals, fine chemicals, and specialty chemicals.

[0048] In still another implementation, producing at least one of derivative product comprises at least one process of a chemical process, a biological process, a catalytic process, and a pyrolytic process.

[0049] In yet another implementation, the method further comprises the step of functionalizing bioglycerin or treated bioglycerin prior to production of at least one derivative product.

[0050] In still yet another implementation, at least one of the derivative products comprise purified glycerin, glycerin derivatives, C1-C3 alcohols, C2/C3 diols, C1-C3 aldehydes/ketones, C1-C3 carboxylic acids, C1-C3 esters of C1-C3 carboxylic acids, C5/C6 polyols, polyol derivatives, glycidol, glycidyl derivatives, glyceraldehyde, glyceraldehyde derivatives, and epihalohydrins produced from the bioglycerin or treated bioglycerin.

[0051] In one implementation, at least one of the C1-C3 alcohols comprise methanol, ethanol, n-propanol, isopropanol, allyl alcohol, and propargyl alcohol.

[0052] In another implementation, at least one of the C2/C3 diols comprise ethylene glycol, 1,2-propanediol, and 1,3-propanediol.

[0053] In still another implementation, at least one of the C1-C3 aldehydes/ketones comprise formaldehyde, acetaldehyde, propionaldehyde, glyoxal, acrolein, acetone, 1- hydroxyacetone, and 1,3-dihydroxyacetone.

[0054] In yet another implementation, at least one of the C1-C3 carboxylic acids comprise formic acid, acetic acid, glycolic acid, glyoxylic acid, oxalic acid, propionic acid, lactic acid, 2,3-dihydroxypropionic acid, pyruvic acid, acrylic acid, malonic acid, and hydroxymalonic acid.

[0055] In still yet another implementation, at least one of the C1-C3 esters of C1-C3 carboxylic acids comprise methyl formate, methyl acetate, methyl glycolate, methyl glyoxylate, dimethyl oxalate, methyl propionate, methyl lactate, methyl 2,3-dihydroxypropionate, methyl pyruvate, methyl acrylate, dimethyl malonate, dimethyl hydroxymalonate, ethyl formate, ethyl acetate, ethyl glycolate, ethyl glyoxylate, diethyl oxalate, ethyl propionate, ethyl lactate, ethyl 2,3-dihydroxypropionate, ethyl pyruvate, ethyl acrylate, diethyl malonate, diethyl

hydroxymalonate, n-propyl formate, n-propyl acetate, n-propyl glycolate, n-propyl glyoxylate, di-n-propyl oxalate, n-propyl propionate, n-propyl lactate, n-propyl 2,3-dihydroxypropionate, n- propyl pyruvate, n-propyl acrylate, di-n-propyl malonate, di-n-propyl hydroxymalonate, isopropyl formate, isopropyl acetate, isopropyl glycolate, isopropyl glyoxylate, diisopropyl oxalate, isopropyl propionate, isopropyl lactate, isopropyl 2,3-dihydroxypropionate, isopropyl pyruvate, isopropyl acrylate, diisopropyl malonate, diisopropyl hydroxymalonate, allyl formate, allyl acetate, allyl glycolate, allyl glyoxylate, diallyl oxalate, allyl propionate, allyl lactate, allyl 2,3-dihydroxypropionate, allyl pyruvate, allyl acrylate, diallyl malonate, and diallyl hydroxymalonate .

[0056] In one implementation, at least one of the purified glycerin and glycerin derivatives comprise purified glycerin, glycerol formal, 4-(hydroxymethyl)-l,3-dioxolan-2-one, 4-methyl-l,3-dioxolane, (2,2-dimethyl-l,3-dioxolan-4-yl)methanol, and 1,4- dioxaspiro[4.5]decane-2-methanol.

[0057] In another implementation, at least one of the glyceraldehyde and

glyceraldehyde derivatives comprise glyceraldehyde, 2,2-dimethyl-l,3-dioxolane-4- carbaldehyde, and l,4-dioxaspiro[4.5]decane-2-carbaldehyde.

[0058] In still another implementation, at least one of the glycidol and glycidyl derivatives comprise glycidol, glycidyl methyl ether, glycidyl ethyl ether, glycidyl n-propyl ether, glycidyl isopropyl ether, glycidyl n-butyl ether, glycidyl isobutyl ether, glycidyl sec-butyl ether, glycidyl tert-butyl ether, glycidyl allyl ether, glycidyl propargyl ether, glycidyl hexadecyl ether, glycidyl octyl/decyl ether, glycidyl phenyl ether, glycidyl benzyl ether, glycidyl formate, glycidyl acetate, glycidyl propionate, glycidyl isopropionate, glycidyl n-butyrate, glycidyl isobutyrate, glycidyl sec-butyrate, glycidyl acrylate, glycidyl methacrylate, diglycidyl 1,2- cyclohexanedicarboxylate, glycidyl benzoate, and glycidyl 4-nitrobenzoate.

[0059] In yet another implementation, at least one of the epihalohydrins comprise epichlorohydrin and epibromohydrin.

[0060] In still yet another implementation, at least one of the polyols and polyol derivatives comprise ribitol, arabitol, xylitol, mannitol, sorbitol, galactitol, allitol, iditol, and bis- (2,2-dimethyl- (l,3)dioxolan-4-yl methanol .

[0061] In one implementation, at least one of the derivative products comprise achiral, racemic, and optically pure products. [0062] In another implementation, the method further comprises the step of using at least one of the derivative product in the production of other chemicals, materials, and products.

[0063] In still another implementation, desalinated bioglycerin has a weight, and a waste product of the desalinated bioglycerin is less than 60% of the desalinated bioglycerin weight.

[0064] In yet another implementation, decolorized bioglycerin has a weight, and a waste product of the decolorized bioglycerin is less than 60% of the decolorized bioglycerin weight.

[0065] In still yet another implementation, concentrated bioglycerin has a weight, and a waste product of the concentrated bioglycerin is less than 60% of the concentrated bioglycerin weight.

[0066] In one implementation, the method for biorefining comprising the steps of: providing bioglycerin; treating the bioglycerin to provide treated bioglycerin; and using waste product from the treated bioglycerin to produce energy.

[0067] In another implementation, the energy is heat or power.

[0068] In still another implementation, the method of biorefining, comprising the steps of providing bioglycerin as a by-product of biodiesel production wherein the bioglycerin is provided from at least one bioglycerin of plant-based bioglycerin, animal-based bioglycerin, and bioglycerin of recycled oil, grease, and fat origin; providing the plant-based bioglycerin from at least one plant-based triglyceride of soybean oil, corn oil, cottonseed oil, canola oil, rice bran oil, flax oil, sunflower oil, safflower oil, artichoke oil, sesame oil, peanut oil, castor oil, coconut oil, colza oil, false flax oil, hemp oil, mustard oil, palm oil, radish oil, rapeseed oil, tigernut oil, tung oil, copaiba oil, jatropha oil, jojoba oil, karanj oil, milk bush (pencil bush) oil, neem oil, olive oil, salicornia oil, and paradise oil; providing the animal-based bioglycerin from at least one animal- based triglyceride of meat, meat by-products, animal fats, animal tallow, choice white grease, yellow grease, lard, fish, fish by-products, fish oil, milk, milk fat, butter fat, and eggs; providing the animal-based bioglycerin from at least one animal-based triglyceride of cattle, pigs, boar, sheep, horses, rabbits, deer, antelope, bison, ox, chickens, turkeys, geese, ducks, quail, ostrich, elk, emu, whales, sharks, dolphins, fish, clams, and mussels; providing the bioglycerin of recycled oil, grease, and fat origin wherein at least one bioglycerin is provided from at least one triglyceride of recycled plant-based oil, recycled plant-based fat, recycled plant-based grease, recycled plant-based butter, recycled plant-based margarine, recycled plant-based lard, and recycled plant-based shortening; providing the bioglycerin of recycled oil, grease, and fat origin wherein at least one bioglycerin is provided from at least one oil of recycled soybean oil, recycled corn oil, recycled cottonseed oil, recycled canola oil, recycled rice bran oil, recycled flax oil, recycled sunflower oil, recycled safflower oil, recycled artichoke oil, recycled sesame oil, recycled peanut oil, recycled castor oil, recycled coconut oil, recycled colza oil, recycled false flax oil, recycled hemp oil, recycled mustard oil, recycled palm oil, recycled radish oil, recycled rapeseed oil, recycled tigernut oil, recycled tung oil, recycled copaiba oil, recycled jatropha oil, recycled jojoba oil, recycled karanj oil, recycled milk bush (pencil bush) oil, recycled neem oil, recycled olive oil, recycled salicornia oil, and recycled paradise oil; providing the bioglycerin of recycled oil, grease, and fat origin wherein at least one bioglycerin is provided from at least one triglyceride of recycled animal-based oil, recycled animal-based fat, recycled animal-based grease, recycled animal-based butter, recycled animal-based margarine, recycled animal-based lard, recycled animal-based shortening, trap grease, and brown grease; providing the bioglycerin of recycled oil, grease, and fat origin wherein at least one of the recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one of recycled meat, recycled meat by-products, recycled animal fat, recycled animal tallow, recycled choice white grease, recycled yellow grease, recycled lard, recycled fish, recycled fish by-products, recycled milk, and recycled eggs; providing the bioglycerin of recycled oil, grease, and fat origin wherein at least one recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one of cattle, pigs, boar, sheep, lambs, horses, rabbits, deer, antelope, bison, ox, chickens, turkeys, geese, ducks, quail, ostrich, elk, emu, whales, sharks, dolphins, fish, clams, and mussels; providing the bioglycerin of recycled oil, grease, and fat origin wherein at least one bioglycerin from at least one recycled product of recycled oil, recycled grease, and recycled fat is provided from at least one recycled triglyceride of residences, restaurants, cafeterias, schools, hotels, camps, hospitals, food preparation facilities, food processing facilities, other food-based businesses, Tenderers, and commercial, industrial, and municipal waste treatment facilities;

treating the bioglycerin to provide treated bioglycerin comprising at least one treatment of desalination treatment, decolorization treatment, and concentration treatment; treating the bioglycerin to provide desalinated bioglycerin using an ion exchange treatment in at least one condition of a batch flow condition and continuous flow condition; treating the bioglycerin to provide decolorized bioglycerin using activated charcoal in at least one condition of a batch flow condition and continuous flow condition; treating the bioglycerin with the activated charcoal; treating the bioglycerin to provide concentrated bioglycerin using at least one of an evaporation process and distillation process in at least one condition of a batch flow condition and continuous flow condition; producing at least one derivative product from the bioglycerin and the treated bioglycerin by at least one process of a chemical process, biological process, catalytic process, and pyrolytic process; recovering and recycling the water, the solvent, and the ion exchange resin from the desalination process; recovering the salt from the desalination process; recovering and recycling the solvent from the decolorization process; recovering and recycling the activated charcoal from the decolorization process; recovering and recycling the water from the concentration process; recovering and recycling the solvent from the concentration process; recovering the treated bioglycerin, wherein the bioglycerin has a weight, the treated bioglycerin has a weight, and the weight of treated bioglycerin is greater than 80% of the weight of bioglycerin; reducing a waste product of the treated bioglycerin, wherein the treated bioglycerin has a weight, and the waste product of the treated bioglycerin is less than 60% of the desalinated bioglycerin weight; producing energy from the waste product of the treated bioglycerin;

functionalizing the bioglycerin and the treated bioglycerin prior to production of at least one derivative product; and producing at least one derivative product comprising purified glycerin and glycerin derivatives, C1-C3 alcohols, C2/C3 diols, C1-C3 aldehydes/ketones, C1-C3 carboxylic acids, C1-C3 esters of C1-C3 carboxylic acids, C5/C6 polyols, polyol derivatives, glycidol, glycidyl derivatives, glyceraldehyde, glyceraldehyde derivatives, and epihalohydrins from the bioglycerin and the treated bioglycerin. [0069] The present invention provides methods for purifying crude bioglycerin and converting crude bioglycerin and/or a purified bioglycerin into value-added, biobased chemicals, derivative products, and/or purified glycerin while minimizing waste products.

[0070] Further, the method described herein provides a method for biorefining that is easy to implement and use.

[0071] To the accomplishment of the foregoing and related ends, the following description and annexed drawings set forth certain illustrative aspects and implementations. These are indicative of but a few of the various ways in which one or more aspects may be employed. Other aspects, advantages and novel features of the disclosure will become apparent from the following detailed description when considered in conjunction with the annexed drawings.

III. Brief Description of the Drawings

[0072] What is disclosed herein may take physical form in certain parts and

arrangement of parts, and will be described in detail in this specification and illustrated in the accompanying drawings which form a part hereof and wherein:

[0073] FIGURE 1 is a flow diagram schematically illustrating what is disclosed herein.

[0074] FIGURE 2 is a flow diagram schematically illustrating what is disclosed herein.

[0075] FIGURE 3 is a flow diagram schematically illustrating what is disclosed herein.

[0076] FIGURE 4 is a flow diagram schematically illustrating what is disclosed herein. [0077] FIGURE 5 is a flow diagram schematically illustrating what is disclosed herein.

[0078] FIGURE 6 is a flow diagram schematically illustrating what is disclosed herein.

[0079] FIGURE 7 is a flow diagram schematically illustrating what is disclosed herein.

[0080] FIGURE 8 is a flow diagram schematically illustrating what is disclosed herein.

[0081] FIGURE 9 is a flow diagram schematically illustrating what is disclosed herein.

[0082] FIGURE 10 is a flow diagram schematically illustrating what is disclosed herein.

[0083] FIGURE 11 is a flow diagram schematically illustrating what is disclosed herein.

[0084] FIGURE 12 is a flow diagram schematically illustrating what is disclosed herein.

Detailed Description

[0085] Referring now to the drawings wherein the showings are for purposes of illustrating embodiments of the invention only and not for purposes of limiting the same.

Relative language used herein is best understood with reference to the drawings, in which like numerals are used to identify like or similar items. [0086] Biodiesel is considered as an environmentally friendly, renewable transportation and heating fuel relative to petroleum diesel. Biodiesel can be made from plant-based and animal-based triglycerides as well as triglycerides from recycled oil, grease, and/or fat origin. Biodiesel from a triglyceride feedstock consists of mono-alkyl esters of long chain fatty acids that are produced by reaction of the triglyceride with an alcohol. This process yields biodiesel through a hydrolysis and/or transesterification reaction during which the crude bioglycerin is cleaved as a by-product from the triglyceride. Thus, the process yields two products: biodiesel and a crude bioglycerin. Unfortunately, the production of biodiesel from a triglyceride feedstock does present a waste product: a crude bioglycerin. The crude bioglycerin is formed in approximately 1 part to each 10 parts of the biodiesel.

[0087] In the pure form, glycerin is a colorless, viscous liquid; however, crude bioglycerin may be a yellowish to dark brown liquid. It may be a clear to a turbid liquid, or have a syrup-like consistency. The crude bioglycerin may contain significant amounts of particulate matter, dissolved inorganic salts, alcohol, water, unreacted fatty acids, and other impurities from the biodiesel process. Because of the high content of these impurities, which can range from about 5% to more than about 30%, uses for the crude bioglycerin are limited while escalating global biodiesel production is culminating in a market glut for this by-product. Additionally, varying purity levels of the crude bioglycerin due to different feedstock sources of the biodiesel, even among various feedstock sources, as well as different levels of in-process control among biodiesel producers, do not provide a uniform approach to treating the crude bioglycerin byproduct. Even if the crude bioglycerin is treated, the purification of the crude bioglycerin historically has been too expensive and commercial implementation of a crude bioglycerin purification process is yet to prove economical at large scale. If an economical process was found to purify the crude bioglycerin, these triglycerides and waste streams of triglycerides may provide renewable means for replacing fossil fuels.

[0088] The crude bioglycerin described in the process herein may be received from various sources. The crude bioglycerin may be obtained from at least one bioglycerin of plant- based bioglycerin, animal-based bioglycerin, and bioglycerin of recycled oil, grease, and fat origin. [0089] Agricultural plant oils and/or other plant-based oils may contain plant-based triglycerides from which biodiesel may be made. Some of these agricultural plant oils may be soybean oil, corn oil, cottonseed oil, canola oil, rice bran oil, flax oil, sunflower oil, safflower oil, artichoke oil, sesame oil, and peanut oil. Some of these other plant-based oils may be castor oil, coconut oil, colza oil, false flax oil, hemp oil, mustard oil, palm oil, radish oil, rapeseed oil, tigernut oil, tung oil, copaiba oil, jatropha oil, jojoba oil, karanj oil, milk bush (pencil bush) oil, neem oil, olive oil, salicornia oil, and paradise oil. Based on this plant-based feedstock sources for biodiesel, agricultural plant oils and/or other plant-based oils, and waste streams of agricultural plant oils and/or other plant-based oils, may provide renewable means for replacing fossil fuels.

[0090] Biodiesel can also be made from animal-based triglycerides. Some of these animal-based triglycerides include tallow, fat, lard, oils, and greases. These animal-based triglycerides, which often pose problems in effective disposal, are a by-product of meat processing and could be an efficient way to produce biodiesel. The crude animal-based bioglycerin may come from a variety of animal-based triglyceride sources. Unlike many of the plant-based bioglycerin feedstock sources that may, for example, use the oil from the seeds and nuts, no animals are bred particularly for fat production. Additionally, the crude bioglycerin of recycled oil, grease, and/or fat origin may be provided from at least one recycled triglyceride provided from a recycled product of recycled plant-based oil, recycled plant-based fat, recycled plant-based grease, recycled plant-based butter, recycled plant-based margarine, recycled plant- based lard, recycled plant-based shortening, recycled animal-based oil, recycled animal-based fat, recycled animal-based grease, recycled animal-based butter, recycled animal-based margarine, recycled animal-based lard, and recycled animal-based shortening. The animal-based triglycerides can be found in various animal products, such as meat, meat by-products, animal fats, animal tallow, choice white grease, yellow grease, lard, fish, fish by-products, milk, and eggs. The animal-based triglycerides may come from cattle, pigs, boar, sheep and/or lambs, horses, rabbits, deer, antelope, bison, ox, chickens, turkeys, geese, ducks, quail, ostrich, elk, emu, whales, sharks, dolphins, fish, clams, and mussels. Fish oil, milk fat, and butter fat may also be sources for animal-based bioglycerin. The types (saturated fat, unsaturated fat, and polyunsaturated fat) of animal-based triglycerides can vary with the species of animal and the fats in their food. In contrast with plants where lipids can be stored in seeds or fruits, fats may be found everywhere in animals. Animals may have more abundant triglycerides in adipose cells, which are found either in concentrated location either subcutaneously or intraperitoneally, or infiltrated among muscle cells and are present in high concentration in bones. Additionally, the animal-based triglycerides are much more saturated and contain a relatively narrow range of fatty acids when compared to most plant-based triglycerides.

[0091] Finally, biodiesel can also be made from recycled plant-based triglycerides of agricultural or other plant origin as well as recycled animal-based triglycerides. Some of these recycled products of agricultural origin may include recycled soybean oil, recycled corn oil, recycled cottonseed oil, recycled canola oil, recycled rice bran oil, recycled flax oil, recycled sunflower oil, recycled safflower oil, recycled artichoke oil, recycled sesame oil, and recycled peanut oil. Some of these other recycled products of plant origin may include recycled castor oil, recycled coconut oil, recycled colza oil, recycled false flax oil, recycled hemp oil, recycled mustard oil, recycled palm oil, recycled radish oil, recycled rapeseed oil, recycled tigernut oil, recycled tung oil, recycled copaiba oil, recycled jatropha oil, recycled jojoba oil, recycled karanj oil, recycled milk bush (pencil bush) oil, recycled neem oil, recycled olive oil, recycled salicornia oil, and recycled paradise oil. Biodiesel may also be made from recycled products of animal-based triglycerides. The recycled animal-based triglyceride can come from various animal products, such as recycled meat, recycled meat by-products, recycled animal fat, recycled animal tallow, recycled choice white grease, recycled yellow grease, recycled lard, recycled fish, recycled fish by-products, recycled milk, and/or recycled eggs. The recycled animal-based triglycerides can originate from cattle, pigs, boar, sheep and/or lambs, horses, rabbits, deer, antelope, bison, ox, chickens, turkeys, geese, ducks, quail, ostrich, elk, emu, whales, sharks, dolphins, fish, clams, and mussels. Based on the sources of recycled products of recycled triglycerides for biodiesel, recycled plant-based oil, recycled plant-based grease, and/or recycled plant-based fat, and/or recycled animal-based oil, recycled animal-based grease, and/or recycled animal-based fat may provide renewable means for replacing fossil fuels; this biodiesel may be made from recycled product of recycled oil, grease, and/or fat origin. The recycled product of recycled oil, grease, and/or fat origin may come from recycled plant-based triglyceride products and/or recycled animal-based triglyceride products that may be provided from various sources as this recycled waste product. The various sources for the recycled product of recycled oil, grease, and/or fat origin may include residences, restaurants, cafeterias, schools, hotels, camps, hospitals, food preparation facilities, food processing facilities, and/or other food-based businesses. The recycled product of recycled oil, grease, and/or fat origin may also include waste oils, fats, grease, butter, margarine, lard, and/or shortening. Additional sources of the recycled product of recycled oil, grease and/or fat origin may include Tenderers, and commercial, industrial, and municipal waste treatment facilities that collect either trap grease and/or brown grease. The recycled product of recycled oil, grease, and/or fat origin from various sources may then be recycled within the process described herein to provide a bioglycerin of recycled oil, grease, and/or fat origin.

[0092] Prior to the production of biodiesel, the recycled product of recycled oil, fat, and/or grease origin may require filtration to remove particulates. These particulates may be food particles and/or other particles that have been introduced into the recycled product of recycled oil, fat, and/or grease origin. Depending on the size and/or nature of the particulates, different methods to remove these particulates may be required. Even though the recycled product of recycled oil, fat, and/or grease origin may be recycled to provide biodiesel, the production of biodiesel from the recycled product of recycled oil, fat, and/or grease origin does present a production by-product: a crude bioglycerin of recycled oil, grease, and/or fat origin.

[0093] Because the crude bioglycerin can be expensive to purify and market demand for the crude material is limited, it is often sold at a significant discount relative to the price of a petroleum-based glycerin. In lieu of a market outlet, the crude bioglycerin would quickly accumulate as an unwanted waste product of biodiesel production with associated disposal costs. Although this green process of creating biofuel is grounded upon the sustainable use of renewable resources, the process unfortunately generates a low- value by-product that diminishes the overall green value of biodiesel production. However, a purified bioglycerin from the production of this biofuel would provide an even greener process as well as become a potential additional revenue stream for biodiesel producers. Such a purified bioglycerin could compete and function as a green replacement to a petroleum-derived glycerin and/or serve as a renewable feedstock for the production of value-added, biobased chemicals, derivative products, and/or purified glycerin.

[0094] In the pure form, glycerin has many uses. It is used in the food and beverage industry as a humectant, sweetener, solvent, preservative, filler, emulsifier, and thickening agent. It also has several uses in the personal care and pharmaceutical industries where it functions as a lubricant, humectant, laxative, bacteriostat, moisturizer and pharmaceutical excipient. It is a well-known component of glycerin soaps. It also has applications in tobacco, polyether polyols, alkyd resins, paints, coatings, lubricants, textiles, paper, biological research, fabric softeners, cellophane, explosives, and epoxy resins. Purer forms of bioglycerin also command a higher market value as compared to a less pure bioglycerin. Additionally, potential emerging applications for bioglycerin include its conversion into commodity chemicals, like 1,2- propanediol and 1,3-propanediol, and into fine chemicals like epichlorohydrin, glycidyl ethers and glycidyl esters. Once implemented, these applications are expected to further improve global market demand for bioglycerin. Overall, a purified bioglycerin from biodiesel production could serve as a feedstock for production of value-added, biobased chemicals, derivative products, and/or purified glycerin, and as a means to reduce costs associated with waste stream disposal.

[0095] FIGURE 1 shows an overall process of converting a crude bioglycerin 10 into a purified bioglycerin 40, and further to the production of biobased chemicals 50. It is a summary of the multiple pathways to process and use the crude bioglycerin 10 as a renewable,

carbonaceous material for the production of biobased chemicals 50.

[0096] The crude bioglycerin 10 can be a by-product of biodiesel production 60 through the hydrolysis and/or transesterification process used in the manufacture of biodiesel 62. Biodiesel production 60 from feedstock sources yields mostly biodiesel 62, with roughly 10% of the product mass being a crude bioglycerin 10. Escalating biodiesel production 60 across the globe is generating large quantities of crude bioglycerin 10 that could be used in the production of a purified bioglycerin 40 and/or the production of biobased chemicals 50. Additionally, the crude bioglycerin 10 may come from other various sources. Crude bioglycerin 10 can also be provided from at least one bioglycerin of 1) plant-based bioglycerin, 2) animal-based bioglycerin, and 3) bioglycerin of recycled oil, grease, and fat origin.

[0097] The crude bioglycerin 10 can contain several impurities from the hydrolysis and/or transesterification process used in the manufacture of biodiesel 62. Such impurities can include water and an alcohol like methanol or ethanol, with methanol the more typical alcohol impurity. The presence of an alcohol in the crude bioglycerin 10 may be due to the fact that an excess of this alcohol can be used to drive the hydrolysis and/or transesterification process of biodiesel production 60 to completion. Also, different biodiesel manufacturers may recover the excess alcohol to varying extents, leading to an inconsistent crude bioglycerin 10. In addition to the alcohol and water impurities, the crude bioglycerin 10 may contain dissolved salts, like sodium chloride, sodium sulfate, potassium chloride, potassium sulfate, calcium chloride, and calcium sulfate. These salts may arise from neutralization of the transesterification and/or hydrolysis process used in biodiesel production 60. Furthermore, the crude bioglycerin 10 may contain residual fatty acids and other impurities leading to color. These impurities may result from either an incomplete process of biodiesel production 60 or from contaminants in the feedstock source entering the refinery. The levels of water and alcohol contamination in the crude bioglycerin 10 may be controlled by evaporation/distillation or by implementing tighter control of the biodiesel processing parameters. However, the salts, which may amount to about 4% to about 10% of the total impurities in the crude bioglycerin 10, can be more challenging to remove. Further these salts may impede transformations of the crude bioglycerin 10 into purified bioglycerin 40 and/or the production of biobased chemicals 50.

[0098] Because of these impurities, there may be a limited market demand for the crude bioglycerin 10 and the market that does exist often may command a price as low as 1/10 ^ώ that of petroleum-derived glycerin. The reason for this limited demand may be that these impurities, and in particular the salts, may severely hamper or restrict uses of the crude bioglycerin 10. Historically, the purification of the crude bioglycerin 10, and in particular the removal of the salt impurities, has proven too expensive for commercial implementation. For example, the purification of the crude bioglycerin 10 by distillation can be a very energy demanding process because the boiling point of glycerin is about 290°C (554°F). However, the purification process illustrated in FIGURE 1 provides a low energy, self-contained process that can remove both the salts and other impurities from the crude bioglycerin 10. The purification process shown in FIGURE 1 can operate as a stand-alone biorefinery receiving the crude bioglycerin 10 for production of purified bioglycerin 40 and also the production of biobased chemicals 50, or it can provide an additional on-site option to a biodiesel manufacturer for waste stream reduction and also the production of value-added products production.

[0099] During biodiesel production 60, the crude bioglycerin 10 may have an inconsistent appearance or impurity profile from batch to batch or from producer to producer. These differences in appearance or impurity profile may be associated with the characteristics of different feedstock sources coming into these biodiesel facilities and/or differences in the processes and manufacturing controls used across different biodiesel facilities. The crude bioglycerin 10 obtained from biodiesel production 60 can appear as a golden or slightly yellow liquid, a dark brown substance, or a blackish liquid. It may have a liquid to a syrup-like character. The crude bioglycerin 10 can be translucent or turbid in appearance. Depending on the condition of the crude bioglycerin 10, several steps within the process of FIGURE 1 can be carried out to produce a purified bioglycerin 40 and/or the production of biobased chemicals 50. These processes can be tailored to meet the end product requirements for a purified bioglycerin 40 and/or the raw material specification requirements for the production of biobased chemicals 50 from a purified bioglycerin 40.

[0100] Depending on the condition of the crude bioglycerin 10, it may need to be subjected to at least one treatment of the desalination treatment 12, the decolorization treatment 22, and the concentration treatment 32. These processing treatments required for purifying the crude bioglycerin 10 depend on the end product requirements for the purified bioglycerin 40 and/or the raw material specification requirements for the production of biobased chemicals 50 from a purified bioglycerin 40. [0101] For instance, if the crude bioglycerin 10 from the biodiesel production 60 requires desalination, it may undergo the desalination treatment 12 to become a desalinated bioglycerin 20. Because these salt impurities can interfere with the purified bioglycerin 40 in the production of biobased chemicals 50, the desalination treatment 12 step is used to remove these impurities in order to provide a desalinated bioglycerin 20. The desalination treatment 12 step is further detailed in FIGURE 2. The desalinated bioglycerin 20 may then go through the decolorization treatment 22 to obtain a decolorized bioglycerin 30 if a lighter colored material is needed. If the crude bioglycerin 10 has not been desalinated, it may also go through the decolorization treatment 22 if required. The decolorization treatment 22 may reduce the level of residual fatty acids and other colored impurities in the material. The decolorization treatment 22 step is further detailed in FIGURE 8.

[0102] The crude bioglycerin 10, the desalinated bioglycerin 20, and/or the decolorized bioglycerin 30 may then undergo the concentration treatment 32 wherein further the alcohol and water impurities are removed to provide a concentrated bioglycerin 38. The concentration treatment 32 step is detailed in FIGURE 9. After the concentration treatment 32 step is complete, a purified bioglycerin 40 can be produced. If desired, the purified bioglycerin 40 can then be transformed into commodity chemicals, fine chemicals, and/or specialty chemicals through a production of biobased chemicals 50 step or it can be further purified. For this process, the purification of the crude bioglycerin 10 does not have to begin with the desalination treatment 12. The purification process may start with the desalination treatment 12, the decolorization treatment 22, or the concentration treatment 32, or it can proceed directly to the production of biobased chemicals 50.

[0103] Within the overall process of converting the crude bioglycerin 10 into a purified bioglycerin 40 and potentially further into production of biobased chemical products 50, several steps may be omitted if the crude bioglycerin 10 does not require at least one step of the desalination treatment 12, the decolorization treatment 22, and the concentration treatment 32 to achieve the end product specification for the purified bioglycerin 40 and/or for the production of biobased chemicals 50. Depending on the condition of the intermediate bioglycerin product during any step of the process shown in FIGURE 1, a determination of whether the material needs to undergo a further treatment can be made. For example, the crude bioglycerin 10 may be subjected to the desalination treatment 12 to remove the salt impurities. If the crude bioglycerin 10 does not require desalination, the desalination treatment 12 can be skipped and crude bioglycerin 10 may then be sent to the decolorization treatment 22 to improve its color. If desalination is required at this point, the decolorized bioglycerin 30 can then be subjected to the desalination treatment 12 to remove the salt impurities. If no desalination is needed, then the decolorized bioglycerin 30 can either go through the concentration treatment 32, or it can be directly converted into purified bioglycerin 40. Alternatively, crude bioglycerin 10 may directly be sent to the concentration treatment 32 for production of a concentrated bioglycerin 38, which may be converted into either purified bioglycerin 40 and/or sent for the production of biobased chemicals 50 if neither desalination nor decolorization is required. In other instances, the crude bioglycerin 10 may omit the desalination treatment 12, the decolorization treatment 22, and the concentration treatment 32 and be directly converted into commodity chemicals, fine chemicals, and/or specialty chemicals with the production of biobased chemicals 50 step.

[0104] After the desalination treatment 12, the desalinated bioglycerin 20 may be sufficiently treated to become a purified bioglycerin 40 if the specification requirements are met for a purified bioglycerin 40 and/or for the production of biobased chemicals 50. Alternatively, if additional processes are needed for the desalinated bioglycerin 20 but not the decolorization treatment 22, then the desalinated bioglycerin 20 may be sent to the concentration treatment 32 where it becomes a concentrated bioglycerin 38, which can be used for the conversion to a purified bioglycerin 40 and/or sent for the production of biobased chemicals 50.

[0105] Additionally, the concentrated bioglycerin 38 may be processed to a purified bioglycerin 40, or undergo either the desalination treatment 12 or the decolorization treatment 22 before it can be used for the conversion to a purified bioglycerin 40 and/or sent for the production of biobased chemicals 50. [0106] One detail to note during these processes is that the summary of the pathway shown in FIGURE 1 may be changed to include a different order for the processes. This is designated by the additional arrows that demonstrate that the final product may not be dependent upon a particular order of the treatments, but rather which treatments can be applied and what processes may be required for the desired end product. This difference in order may be needed due to processing limitations or discoveries with respect to what may be required to meet the specifications of the end product or intended use as a purified bioglycerin 40 and/or sent for the production of biobased chemicals 50. In other words, the order of treatments provided in FIGURE 1 does not have to be strictly followed. The desalination treatment 12, the

decolorization treatment 22, and the concentration treatment 32 may occur in any order depending on the end product requirements for the purified bioglycerin 40 and/or the production of biobased chemicals 50. The order for the treatments may also depend upon logistics of the processing facility.

[0107] Also, any of the process treatment steps like the desalination treatment 12, the decolorization treatment 22, or the concentration treatment 32, may be repeated to provide the requirements for a purified bioglycerin 40 and/or the production of biobased chemicals 50.

[0108] Furthermore, any of the process treatment steps like the desalination treatment 12, the decolorization treatment 22, or the concentration treatment 32, may be conducted under batch or flow conditions for the production of a purified bioglycerin 40 and/or the production of biobased chemicals 50.

[0109] The processing outlined in FIGURE 1 can also address problems with processing the crude bioglycerin 10 without the need to invest large amounts of capital in expensive processing equipment to purify this by-product of biodiesel production 60. [0110] The processing outlined in FIGURE 1 can further avoid the high costs of purifying the crude bioglycerin 10 by conventional means in that the process in FIGURE 1 can be low energy and self-contained.

[0111] FIGURE 2 illustrates an overview of the process for the desalination treatment 12 in which the high salt bioglycerin 14 may be transformed into a desalinated bioglycerin 20. This desalination process may occur through ion exchange to remove the salt impurities. The ion exchange treatment or process can be a two-stage process consisting of both the anion exchange treatment 16 and the cation exchange treatment 18. This two-step, ion exchange treatment can utilize both anion exchange resins and cation exchange resins to purify the high salt bioglycerin 14 by acting to exchange the ions that contribute to the salt impurities of the high salt bioglycerin 14. Anions are atoms or groups of atoms that have gained electrons, and are therefore negatively charged. Cations are atoms or groups that have lost an electron to become positively charged. Together, anions and cations form salts like sodium chloride, sodium sulfate, potassium chloride, potassium sulfate, calcium chloride, and calcium sulfate. Anion exchange resins and cation exchange resins can be both selective and versatile, where specific types of ions can be removed from a material depending on the specific anion exchange treatment 16 and the cation exchange treatment 18 chosen.

[0112] First, the high salt bioglycerin 14 may be received. The high salt bioglycerin 14 can originate from a crude bioglycerin 10, a decolorized bioglycerin 30, and/or a concentrated bioglycerin 38. The high salt bioglycerin 14 may then undergo the anion exchange treatment 16. The anion exchange treatment 16 step can serve to reduce or remove the anionic impurities present in the high salt bioglycerin 14 by use of an anion exchange resin, which exchanges the negatively charged ions of the salt impurities in the high salt bioglycerin 14 with the counterion bound to the resin. For instance, this anion exchange treatment 16 may remove halide, sulfate, and other anions first from the high salt bioglycerin 14 and replace those anions with hydroxide anions. Through the anion exchange treatment 16, the anionic components of the salt impurities can be removed from the high salt bioglycerin 14. After the anion exchange treatment 16 step is completed, the cation exchange treatment 18 step may then occur to reduce and replace the cations from the salt impurities present in the high salt bioglycerin 14 with the counterion bound to the cation exchange resin, typically a proton. Through the cation exchange treatment 18, the cationic components of the salt impurities may be reduced and removed from the high salt bioglycerin 14. For example, this cation exchange treatment 18 may remove sodium, potassium, calcium, and other cations and replace those cations with protons. Therefore, through both anion and cation exchange treatment steps, the high salt bioglycerin 14 can be reduced in levels of both positively and negatively charged ionic salt impurities, and the desalinated bioglycerin 20 may now be formed. The desalinated bioglycerin 20 may then go through one or more additional treatments of decolorization, concentration, and transfer to the production of biobased chemicals 50 as described in FIGURE 1. In the course of the desalination treatment 12, water can be produced as a by-product through a combination of the hydroxide anions derived from the anion exchange treatment 16 step with the protons derived from the cation exchange treatment 18 step. To reduce waste streams, this water may be recovered and reused in the desalination treatment 12.

[0113] Although the desalination treatment 12 in which the high salt bioglycerin 14 is transformed into a desalinated bioglycerin 20 can be achieved by first subjecting the high salt bioglycerin 14 to the anion exchange treatment 16 step and following that step with the cation exchange treatment 18 step, the process is not limited to this order of ion exchange treatments. Instead, the high salt bioglycerin 14 can first undergo the cation exchange treatment 18, and then followed by the anion exchange treatment 16. In other words, either ion exchange treatment can be used first.

[0114] Alternatively, the high salt bioglycerin 14 can undergo only one of the exchange treatments, either the anion exchange treatment 16 or the cation exchange treatment 18.

Depending on the condition of the high salt bioglycerin 14 or the conditions required for the desalinated bioglycerin 20, the anion exchange treatment 16 or the cation exchange treatment 18 can be omitted. [0115] Alternatively, an amphoteric exchange treatment could be used instead wherein both the anion exchange treatment 16 and the cation exchange treatment 18 occur at once. This type of amphoteric exchanger will exchange both cations and anions simultaneously. Instead of completing two different steps where the anion exchange treatment 16 step and the cation exchange treatment 18 step are separate, a process where all of the ion exchanging can occur in a condensed step may also be used.

[0116] Moreover in the course of the desalination treatment 12, each of the steps of the anion exchange treatment 16 and the cation exchange treatment 18 may be conducted more than one time. Repeating the anion exchange treatment 16 step and/or the cation exchange treatment 18 step can allow for applications wherein the levels of dissolved salts in the desalinated bioglycerin 20 may be further reduced, especially if required for certain specifications of intended product use.

[0117] The reduction in levels of both positively and negatively charged ions in the desalination treatment 12 may lead to the formation of a desalinated bioglycerin 20 since the salt impurities are reduced or removed by the ion exchange treatment or process. With the desalination treatment 12 of the high salt bioglycerin 14, both the possibility of creating value- added products and the prevention of a costly waste stream may provide incentives for utilizing the desalination treatment 12 process.

[0118] In FIGURE 3, a detailed batch purification method for the desalination treatment 12 of the high salt bioglycerin 14 is shown. During this batch process, the high salt bioglycerin 14 can be converted into a desalinated bioglycerin 20. The ion exchange treatment or process may be done through multiple batch anion exchange and cation exchange treatments. These anion and cation exchange treatments typically employ an ion exchange resin to remove the negatively charged and positively charged ions that are present in the salt impurities of the high salt bioglycerin 14. [0119] Ion exchange resins are classified as cation exchangers, on which positively charged mobile ions may be available for exchange, and anion exchangers, on which the exchangeable ions are negatively charged. Both anion exchange resins and cation exchange resins may be produced from the same basic organic polymers. These resin types differ in the ionic functional group attached to the organic polymer network. It is this ionic functional group that determines the chemical behaviour of the resin. Ion exchange resins can be broadly classified as strong or weak acid cation exchangers, or strong or weak base anion exchangers. Ion exchange resins are insoluble substances containing loosely bound counterions that are able to be exchanged with other ions in solutions that come into contact with the resin. These exchanges take place without any physical alteration to the ion exchange material other than the exchange of the loosely bound counterions.

[0120] For the anion exchange treatment 16 and the cation exchange treatment 18 of the high salt bioglycerin 14 shown in FIGURE 2, two different purification methods can be used: batch purification and continuous flow purification. In both instances, the high salt bioglycerin 14 would be subjected to ion exchange resins. Batch purification allows for purification in discrete batches. Batch purification is especially advantageous where different end products are needed. Continuous flow purification provides processing in a continuous flow, and allows for an increased production of a particular end product. A batch purification method is shown in FIGURE 3. A continuous flow purification method is outlined in FIGURE 4. There are, however, different modifications that must be considered in determining which purification method to use. In the batch purification method, the ion exchange resin is isolated by filtration before regeneration. This regeneration process for the batch purification method is illustrated generally in FIGURE 6. Unlike the batch purification method, the continuous flow purification method regenerates the ion exchange resin within a column, as shown in FIGURE 7. No matter which method is utilized, either method will provide the desalinated bioglycerin 20.

[0121] Returning now to FIGURE 3, the high salt bioglycerin 14 can be received in the batch purification method for the desalination treatment 12. The high salt bioglycerin 14 may originate from a crude bioglycerin 10, a decolorized bioglycerin 30, and/or a concentrated bioglycerin 38. As the crude bioglycerin 10, the decolorized bioglycerin 30, and/or the concentrated bioglycerin 38 may be brought together as the high salt bioglycerin 14, an optional solvent addition 8 can be done. This optional solvent addition 8 can be water, an alcohol, an alcohol/water mixture, or another solvent in which the high salt bioglycerin 14 may be miscible. The optional solvent addition 8 may typically be an alcohol like methanol, but may also be ethanol. This optional solvent addition 8 can serve to reduce the viscosity of the high salt bioglycerin 14 and help enhance recovery of the desalinated bioglycerin 20 from the ion exchange resins. Solvents used in the optional solvent addition 8 may be recovered in the concentration treatment 32, as shown in FIGURE 1.

[0122] For FIGURE 3, the high salt bioglycerin 14 may be subjected to multiple treatments with both anionic and cationic ion exchangers in order to produce the desalinated bioglycerin 20. The flow path for the ion exchange treatments can depend upon the anion and cation level specifications for production of either the desalinated bioglycerin 20 or purified bioglycerin 40 for the production of biobased chemicals 50. Although FIGURE 3 provides a general flow in the production of a desalinated bioglycerin 20, the process may instead provide a purified bioglycerin 40 for the production of biobased chemicals 50. A general flow is outlined in FIGURE 3, but any of the exchange treatments may be repeated or skipped altogether, depending on the requirements and product specifications for the intended use. Additionally, FIGURE 3 shows a batch flow that is first subjected to anion exchange treatments and is then subjected to cation exchange treatments. However, the cation exchange treatments may be conducted before the anion exchange treatments if the material requires this process or if the batch process desalination treatment 12 is set-up to process the high salt bioglycerin 14 with the batch cation exchange treatments first.

[0123] The batch purification method outlined in FIGURE 3 shows a series of both anion and cation exchange treatments. The batch anion exchange treatment 80 may occur first. In an anion exchange resin treatment, the resin can reduce or remove halide, sulfate, and other anions that are present as impurities in the high salt bioglycerin 14 and instead replace those anions by the counterion bound to the anion exchange resin, typically hydroxide anions. A second and third anion exchange treatment, the batch anion exchange treatment 82 and the batch anion exchange treatment 84, may then occur. The purpose of second and third batch anion exchange treatments can be to further reduce the respective anion impurity levels of the product to specification for a desalinated bioglycerin 20 and/or a purified bioglycerin 40 for the production of biobased chemicals 50. Depending upon the resin, the anion exchange resin can be regenerated with an alkali base like aqueous sodium hydroxide, aqueous potassium hydroxide, or aqueous ammonia after the anion exchange treatment 82. This resin regeneration process is detailed further in FIGURE 6.

[0124] The batch cation exchange treatment 90 may then occur after the anion exchange treatment(s). In a cation exchange resin treatments, the resin may reduce or remove sodium, potassium, calcium, and other cations from the impurities present in the high salt bioglycerin 14 and replace those cations by the counterion bound to the cation exchange resin, typically protons. The high salt bioglycerin 14 may then undergo a second and third cation exchange, the batch cation exchange treatment 92 and the batch cation exchange treatment 94. Like the anion exchange treatment process, the purpose of second and third batch cation exchange treatments can be to further reduce the respective cation levels of the product to specification for a desalinated bioglycerin 20 and/or a purified bioglycerin 40 for the production of biobased chemicals 50. Depending on the resin, the cation exchange resin can be regenerated with aqueous mineral acids like aqueous hydrochloric acid or aqueous sulfuric acid, as detailed further in FIGURE 6.

[0125] Besides the resin regeneration that provides a greener and less costly means of desalinating the high salt bioglycerin 14, the batch purification method of FIGURE 3 also can potentially generate both salt and water as recoverable by-products. This process is detailed further in FIGURE 5.

[0126] In FIGURE 4, a detailed continuous flow purification method for the

desalination treatment 12 of the high salt bioglycerin 14 is shown. During this continuous flow process, the high salt bioglycerin 14 can be converted into a desalinated bioglycerin 20. The ion exchange treatment may be done through multiple anion exchange and cation exchange treatments. These anion and cation exchange treatments typically employ an ion exchange resin to remove the negatively charged and positively charged ionic impurities present in the high salt bioglycerin 14.

[0127] First, the high salt bioglycerin 14 may be received in the continuous flow purification method for the desalination treatment 12. The high salt bioglycerin 14 can originate from at least one bioglycerin of crude bioglycerin 10, a decolorized bioglycerin 30, and a concentrated bioglycerin 38. As the crude bioglycerin 10, the decolorized bioglycerin 30, and/or the concentrated bioglycerin 38 may be brought together as the high salt bioglycerin 14, an optional solvent addition 8 can be done. This optional solvent addition 8 can be water, an alcohol, an alcohol/water mixture, or other solvent in which the high salt bioglycerin 14 may be miscible. The optional solvent addition 8 may typically be an alcohol like methanol, but may also be ethanol. This optional solvent addition 8 serves to reduce the viscosity of the high salt bioglycerin 14 and helps enhance recovery of the desalinated bioglycerin 20 from the ion exchange resins. Solvents used in the optional solvent addition 8 may be recovered in the concentration treatment 32, as shown in FIGURE 1.

[0128] Like the batch purification method in FIGURE 3, the high salt bioglycerin 14 of FIGURE 4 may be subjected to multiple treatments with both anionic and cationic ion exchangers in order to produce the desalinated bioglycerin 20. The flow path for the ion exchange treatments depends upon the anion and cation level specifications for the production of either a desalinated bioglycerin 20 and/or a purified bioglycerin 40 for the production of biobased chemicals 50. Although FIGURE 4 provides a general flow in the production of a desalinated bioglycerin 20, the process may instead lead to a purified bioglycerin 40 for the production of biobased chemicals 50.

[0129] The general flow outlined in FIGURE 4 shows a continuous flow process that can be first subjected to the flow anion exchange treatments 86, and is then subjected to the flow cation exchange treatments 96. However, the cation exchange treatments may be conducted prior to the anion exchange treatments if the material requires this desalination process or if the continuous flow process desalination treatment 12 is set-up to process the high salt bioglycerin 14 with the cation exchange treatments first.

[0130] Optionally, a reduced anion bioglycerin 88 may be obtained from the flow anion exchange treatment 86, which may be subjected to one or more cycles of the flow anion exchange treatment 86. These treatments are optional cycles of flow anion exchange where the reduced anion bioglycerin 88 can be sent through the flow exchange column again to further reduce anion levels to the desired specifications for the desalinated bioglycerin 20 and/or purified bioglycerin 40 for the production of biobased chemicals 50.

[0131] Also, the reduced cation bioglycerin 98 may be optionally subjected to one or more cycles of the flow cation exchange treatment 96 in order to meet the cation levels to the desired specifications for the production of the desalinated bioglycerin 20 and/or a purified bioglycerin 40 for the production of biobased chemicals 50. Like the optional cycles of the flow anion exchange treatment 86 of the reduced anion bioglycerin 88, the reduced cation bioglycerin 98 can be subjected to optional cycles of the flow cation exchange treatment 96.

[0132] Depending upon the resin, the anion exchange resin can be regenerated with an alkali base like aqueous sodium hydroxide, aqueous potassium hydroxide, or aqueous ammonia, and the cation exchange resin can be regenerated with aqueous mineral acids like aqueous hydrochloric acid or aqueous sulfuric acid after the continuous flow exchange process. Besides the resin regeneration providing a greener and less costly means of desalinating the high salt bioglycerin 14, the continuous flow purification method of FIGURE 4 also can potentially generate both salt and water as recoverable by-products. This process is detailed further in FIGURES 5, 6 and 7.

[0133] FIGURE 5 illustrates an optional water and salt recovery in the desalination treatment 12 operating under batch flow or continuous flow conditions. As the high salt bioglycerin 14 may be received, it can be subjected to the desalination treatment 12 to provide a desalinated bioglycerin 20. In the desalination treatment 12, both the recovered water 114 and the recovered inorganic salt 116 may be salvaged and used to either provide additional products or prevent additional waste streams. Besides the desalinated bioglycerin 20 and/or a purified bioglycerin 40 for the production of biobased chemicals 50, the recovered water 114 and the recovered inorganic salt 116 can be considered as additional products from the desalination treatment 12 rather than unwanted by-products or waste streams.

[0134] FIGURE 6 shows the optional exchange resin regeneration 118 in the desalination treatment 12 operating under batch flow or continuous flow. After the high salt bioglycerin 14 is received, it may undergo the desalination treatment 12 to provide the desalinated bioglycerin 20. This desalination treatment 12 can use ion exchange resins to desalinate the high salt bioglycerin 14. Ion exchange resins are polymers that are capable of exchanging particular cations or anions within the polymer with ions within a solution that is passed through the ion exchange resins.

[0135] One of the advantages of using an ion exchange treatment or process to desalinate the high salt bioglycerin 14 for other applications can be that the treatment or process itself can generate little to no waste. Another advantage may be that the ion exchange resins used in the ion exchange treatment or process can be regenerated and recycled. In other words, the ion exchange resins can be used multiple times, providing a greener process with fewer waste products and minimizing costs with purchasing new ion exchange resins.

[0136] The exchange resin regeneration 118 is detailed further in FIGURE 7 for the continuous flow ion exchange process.

[0137] FIGURE 7 offers a depiction of the desalination treatment 12 with both the exchange resin regeneration 118 as well as the salt and water recovery while operating in a continuous flow. It also provides several optional methods to control wastes and costs associated with the ion exchange treatment or process and allow for additional products to be formed, namely the recovered water 114 and the recovered inorganic salt 116.

[0138] In FIGURE 7, the exchange resin regeneration 118 can be used to further reduce costs and potential wastes associated with the process. One of the advantages of using an ion exchange treatment or process to desalinate the high salt bioglycerin 14 may be that the process itself generates little to no waste. Like the other green aspects of this process, the ion exchange resins used can be regenerated and recycled. In fact, the ion exchange resins can be used multiple times, providing a greener process with fewer waste products and minimizing costs with purchasing new ion exchange resins.

[0139] Ion exchange resins are polymers that are capable of exchanging particular ions within the polymer with ions within a solution that is passed through the ion exchange resins. This can occur for anion resin exchangers in the flow anion exchange treatment 86 and for cation exchange resins in the flow cation exchange treatment 96 of FIGURES 4 and 7. The ion exchange resins can be regenerated or loaded with desirable ions by washing the resin with an excess of the desired ions. The ion exchange resin can then be then flushed free of the newly- exchanged ions from desalination of the high salt bioglycerin 14 by contacting the resin with a solution of the desirable ions. Ion exchange resin regeneration 118 may be initiated after most of the active sites on the resin have been exchanged with ions from the high salt bioglycerin 14 and the ion exchange treatment or process may no longer be effective. With the exchange resin regeneration 118, the same resin beads can be used over and over again for the flow anion exchange treatment 86 or the flow cation exchange treatment 96, and the ions that need to be removed from the system can be concentrated from the aqueous inorganic salt 112 to provide the recovered water 114 and the recovered inorganic salt 116.

[0140] There are two types of ion exchange resins used in the continuous flow process. The first may be an anion exchange resin and the second may be a cation exchange resin.

Whether the anion exchange resin or the cation exchange resin may be used, the regeneration process can be similar. Although the anion exchange resin and the cation exchange resin may be processed similarly, each ion exchange resin can be separately regenerated.

[0141] After acting to desalinate the high salt bioglycerin 14 of FIGURE 4, either the flow anion exchange treatment 86 or the flow cation exchange treatment 96 can be brought into the regeneration process of FIGURE 7. This flow anion exchange treatment 86 or the flow cation exchange treatment 96 may consist of either the anion exchange resin or the cation exchange resin at least partially saturated with ionic impurities removed from the high salt bioglycerin 14. The anion exchange resin can then be put through the saturated anion exchange resin column 102, and the cation exchange resin may then subjected to the saturated cation exchange resin column 108. In these resin columns, the exchange resin regeneration 118 can occur. These columns can be the same or different columns from that used in the flow anion exchange treatment 86 and the flow cation exchange treatment 96.

[0142] For the anion exchange resin regeneration, typically an aqueous alkali 100 may be added to the anion exchange resin in the saturated anion exchange resin column 102. In this process, the regenerated anion exchange resin column 104 will be formed along with an aqueous inorganic salt 112. Typically, this aqueous alkali 100 can be aqueous sodium hydroxide, aqueous potassium hydroxide, aqueous ammonia, or another source of aqueous hydroxide anion that may be compatible with the anion exchange resin. From the regenerated anion exchange resin column 104, the anion exchange resin can be reused after it is directed back to the flow anion exchange treatment 86.

[0143] Alternatively in the cation exchange resin regeneration, an aqueous mineral acid 106 can be added to the cation exchange resin in the saturated cation exchange resin column 108, and the regenerated cation exchange resin column 110 may be formed along with an aqueous inorganic salt 112. Typically, this aqueous mineral acid 106 can be aqueous hydrochloric acid or aqueous sulfuric acid, with aqueous sulfuric acid being the less expensive option and could be used to keep costs down. Depending on compatibility with the cation exchange resin, certain other protic acids may be used in the regenerated cation exchange resin column 110. After this regeneration process in the regenerated cation exchange resin column 108, the cation exchange resin can be reused after it is directed back to the flow cation exchange treatment 96.

[0144] Besides the regeneration of both the anion and cation exchange resins, the process can also provide the recovered water 114 and the recovered inorganic salt 116. After both the flow anion exchange treatment 86 and the flow cation exchange treatment 96, an aqueous inorganic salt 112 may be formed in the saturated anion exchange resin column 102 and the saturated cation exchange resin column 108. Instead of initiating another waste stream, this aqueous inorganic salt 112 salt can generate yet another profitable chemical source and/or prevent disposal of another waste stream. A separation of the recovered water 114 and the recovered inorganic salt 116 can be achieved through at least one separation process of evaporation, distillation, reverse osmosis, ion exchange, and crystallization of the salt from a saturated solution. The recovered salt may be sold for industrial applications such as road salt, chilling salts, or the like. In some cases, the salt formed during this phase may also be recovered for use as fertilizer or as a material for lowering the freezing point. Other potential applications may also include water softening, food additives, de-icing, and the production of

pharmaceuticals and other chemicals.

[0145] After the water is removed from the aqueous inorganic salt 112 as the recovered water 114, it can either be safely added to the wastewater system or it could be recycled and reused elsewhere in the desalination process of FIGURE 1 so as to minimize a waste stream.

[0146] FIGURE 8 describes the decolorization treatment 22 that can be used in either the batch process or continuous flow process. The decolorization treatment 22 may be done on the crude bioglycerin 10, a desalinated bioglycerin 20, and/or a concentrated bioglycerin 38. At least one of the crude bioglycerin 10, the desalinated bioglycerin 20, and/or the concentrated bioglycerin 38 can be brought into the treatment as the colored bioglycerin 120. [0147] After the colored bioglycerin 120 is collected, it may undergo an optional solvent addition 8. Like the optional solvent addition 8 in the desalination treatment 12 shown in FIGURES 3 and 4, the decolorization treatment 22 does not require this step. This optional solvent addition 8 can be water, an alcohol, an alcohol/water mixture, or other solvent in which the colored bioglycerin 120 may be miscible. The optional solvent addition 8 may typically be an alcohol like methanol, but may also be ethanol. This optional solvent addition 8 serves to reduce the viscosity of the colored bioglycerin 120 and helps enhance recovery of the

decolorized bioglycerin 30 from the charcoal treatment 122. The optional solvent addition 8 may be recovered in the concentration treatment 32, as shown in FIGURE 1.

[0148] With or without the optional solvent addition 8, the colored bioglycerin 120 may then be subjected to the charcoal treatment 122. If it is used, the charcoal treatment 122 serves to reduce or remove color and improve the clarity of the resulting decolorized bioglycerin 30. The charcoal treatment 122 may work primarily by an adsorption mechanism. Adsorption is the adhesion of solid materials or dissolved materials onto a surface based on surface energy.

During the charcoal treatment 122, the level of residual fatty acids and colored impurities present in colored bioglycerin 120 can be reduced or removed by adhesion onto an adsorbent, typically activated charcoal. That is, the charcoal treatment 122 may be a more selective adsorption method for removal of these impurities than it can be for the decolorized bioglycerin 30. The colored impurities may adhere to the activated charcoal adsorbent used in the charcoal treatment 122. This charcoal treatment 122 may provide a lighter colored to a nearly clear decolorized bioglycerin 30. Depending upon the stage of the purification process of FIGURE 1, the decolorized bioglycerin 30 can be over 99% pure after removal of any optionally added solvent.

[0149] Furthermore, a reduction in the level of residual fatty acid and colored impurities in the colored bioglycerin 120 can be additionally controlled depending on the number of charcoal treatments 122. Depending on the intended use of the decolorized bioglycerin 30, the charcoal treatment 122 may have a variety of different processing methods. These methods may include the additional step of repeating cycles of the charcoal treatment 122 of the color treated bioglycerin 124. The optional charcoal treatment 122 and the number of its repeating cycles can depend on the color of the colored bioglycerin 120 and level of the colored impurities. However, a more decolorized bioglycerin 30 may require increased energy and costs associated with additional cycles of the charcoal treatment 122.

[0150] After the desired color of the color treated bioglycerin 124 may be achieved through the charcoal treatment(s) 122, the color treated bioglycerin 124 can move to a decolorized bioglycerin 30. The resulting decolorized bioglycerin 30 may be sent to the desalination treatment 12, or the concentration treatment 32, or can become a purified

bioglycerin 40 for the production of biobased chemicals 50 as illustrated in FIGURE 1.

[0151] In FIGURE 8, the activated charcoal used in the charcoal treatment 122 can be regenerated and recycled more than one time to further reduce costs and potential wastes associated with the decolorization treatment 22. This regeneration may take place whenever the adsorbent becomes saturated with impurities removed from the colored bioglycerin 120, or when the efficiency of the charcoal treatment 122 is reduced. The activated charcoal can be regenerated through an adsorbent regeneration 160 step involving at least one of steam

regeneration, thermal activation regeneration, and chemical regeneration. One of the advantages of using the decolorization treatment 22 or process to decolorize the colored bioglycerin 120 may be that the process itself generates little to no waste. Like the other green aspects of this crude bioglycerin purification process, the activated charcoal adsorbent used can be regenerated and recycled. In fact, the activated charcoal adsorbent can be used more than one time to decolorize the colored bioglycerin 120, providing a greener process with fewer waste products and minimizing costs with purchasing new adsorbent.

[0152] FIGURE 9 describes the concentration treatment 32 that can be used in either the batch process or continuous flow process. FIGURE 9 shows the process in which a diluted bioglycerin 130 may be treated to provide the concentrated bioglycerin 38 and/or the recovered alcohol and water 134. [0153] The concentration treatment 32 may be done on the crude bioglycerin 10, a desalinated bioglycerin 20, and/or a decolorized bioglycerin 30. At least one of the crude bioglycerin 10, the desalinated bioglycerin 20, and/or the decolorized bioglycerin 30 can be brought into the treatment as the diluted bioglycerin 130.

[0154] With the concentration treatment 32, the diluted bioglycerin 130 may undergo the evaporator/concentrator treatment 132 to produce the concentrated bioglycerin 38 and/or the recovered alcohol and water 134. In the evaporator/concentrator treatment 132, the lower boiling alcohol and water impurities can be separated from the diluted bioglycerin 130 under reduced pressure and modest temperatures. When the alcohol is methanol or ethanol, these temperatures may be about 25° C to about 60° C. These reduced pressures may be about 20 mm Hg to about 70 mm Hg. These temperatures may also be higher or the pressures further reduced depending upon the material and equipment capabilities and requirements. By using this concentration treatment 32, the recovered alcohol and water 134 may be removed from the diluted bioglycerin 130 and the resulting concentrated bioglycerin 38 may be further processed by the desalination treatment 12, or the decolorization treatment 22, and/or be sent to a purified bioglycerin 40 for the production of biobased chemicals 50 as shown in FIGURE 1.

[0155] Similarly with the concentration treatment 32, the diluted bioglycerin 130 may undergo the evaporator/concentrator treatment 132 to remove solvent from the diluted bioglycerin 130 which may be added during the desalination treatment 12 and/or the

decolorization treatment 22 steps of the purification process in FIGURE 1. That is to say, the concentration treatment 32 may produce the concentrated bioglycerin 38, and/or the recovered alcohol and water 134, and/or a solvent.

[0156] FIGURE 10 shows a flowchart of several biobased chemicals, derivative products, and purified glycerin that may be formed from the process. First, the production of biobased chemicals 50 may be provided by a purified bioglycerin 40 of various purities.

Alternatively, the production of biobased chemicals 50 may be provided by the crude bioglycerin 10 as shown in FIGURE 1. Additionally, an optional functionalization process 140 can also be done to provide the functionalized bioglycerin products 142 and also lead further to the production of biobased chemicals 50. This optional functionalization process 140 may serve to further present added commodity chemicals 144, fine chemicals 146, and/or specialty chemicals 148 that may not be made without this functionalization. This optional functionalization process 140 may include chemical, catalytic, and/or biological means of functionalizing the purified bioglycerin 40, and/or the crude bioglycerin 10, prior to the production of biobased chemicals 50. Examples of an optional functionalization process 140 may include, but are not limited to, the preparation of 5- and 6-membered ring acetals and ketals, esterifications, and oxidations of the purified bioglycerin 40 and/or the crude bioglycerin 10 to provide functionalized bioglycerin products 142 like glycerol formal, 4-(hydroxymethyl)-l,3-dioxolan-2-one, solketal, and glyceraldehyde.

[0157] From the production of biobased chemicals 50, either with or without the optional functionalization process 140, commodity chemicals 144, fine chemicals 146, and/or specialty chemicals 148 may be produced. Several of these commodity chemicals 144, fine chemicals 146, and/or specialty chemicals 148 may be those shown in FIGURES 11 and 12.

[0158] FIGURE 11 illustrates the production of biobased chemicals 50 from either the purified bioglycerin 40 and/or the functionalized bioglycerin products 142. In other instances, the production of biobased chemicals 50 may directly proceed from the crude bioglycerin 10 as shown in FIGURE 1. These derivative biobased products 158 can be converted into commodity chemicals 144, fine chemicals 146, and/or specialty chemicals 148. From FIGURE 11, the purified bioglycerin 40 and/or the functionalized bioglycerin products 142 may be converted into derivative biobased products 158 through methods of chemical production 150, catalytic production 152, biological production 154, and/or pyrolytic production 156. By using at least one of the conversion methods, including chemical production 150, catalytic production 152, biological production 154, and/or pyrolytic production 156, the purified bioglycerin 40 and/or the functionalized bioglycerin products 142 may be able to produce the derivative biobased products 158 that have both financial value by conversion to value-added products and utilization of a low-value by-product/waste stream of biodiesel production 60. Additionally, the plurality of the production of biobased chemicals 50 and/or the derivative biobased products 158 produced from the functionalized bioglycerin products 142 and/or the purified bioglycerin 40 may comprise at least one of achiral, racemic, and optically pure products. These derivative biobased products 158, including commodity chemicals 144, fine chemicals 146, and/or specialty chemicals 148, may be specifically modified to provide at least one of achiral, racemic, and optically pure products. Based on the method of conversion of the purified bioglycerin 40 and/or the functionalized bioglycerin products 142 to the production of biobased chemicals 50, the derivative biobased products 158 may be selectively produced.

[0159] FIGURE 12 provides some potential end products from the production of biobased chemicals 50. These end products from the production of biobased chemicals 50 may further include the production of other chemicals, materials, and products. These products may be selectively produced using the method described herein.

[0160] The product categories of the end products from the production of biobased chemicals 50 may include but are not limited to purified glycerin, glycerin derivatives, C1-C3 alcohols, C2/C3 diols, C1-C3 aldehydes/ketones, C1-C3 carboxylic acids, C1-C3 esters of Cl- C3 carboxylic acids, C5/C6 polyols, polyol derivatives, glycidol, glycidyl derivatives, glyceraldehyde, glyceraldehyde derivatives, and epihalohydrins. Thereunder the production of biobased chemicals 50, a plurality of specific chemicals can be made comprising but not limited to purified glycerin, methanol, ethanol, n-propanol, isopropanol, allyl alcohol, propargyl alcohol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, formaldehyde, acetaldehyde,

propionaldehyde, glyoxal, acrolein, acetone, 1-hydroxyacetone, 1,3-dihydroxyacetone, formic acid, acetic acid, glycolic acid, glyoxylic acid, oxalic acid, propionic acid, lactic acid, 2,3- dihydroxypropionic acid, pyruvic acid, acrylic acid, malonic acid, hydroxymalonic acid, methyl formate, methyl acetate, methyl glycolate, methyl glyoxylate, dimethyl oxalate, methyl propionate, methyl lactate, methyl 2,3-dihydroxypropionate, methyl pyruvate, methyl acrylate, dimethyl malonate, dimethyl hydroxymalonate, ethyl formate, ethyl acetate, ethyl glycolate, ethyl glyoxylate, diethyl oxalate, ethyl propionate, ethyl lactate, ethyl 2,3-dihydroxypropionate, ethyl pyruvate, ethyl acrylate, diethyl malonate, diethyl hydroxymalonate, n-propyl formate, n- propyl acetate, n-propyl glycolate, n-propyl glyoxylate, di-n-propyl oxalate, n-propyl propionate, n-propyl lactate, n-propyl 2,3-dihydroxypropionate, n-propyl pyruvate, n-propyl acrylate, di-n- propyl malonate, di-n-propyl hydroxymalonate, isopropyl formate, isopropyl acetate, isopropyl glycolate, isopropyl glyoxylate, diisopropyl oxalate, isopropyl propionate, isopropyl lactate, isopropyl 2,3-dihydroxypropionate, isopropyl pyruvate, isopropyl acrylate, diisopropyl malonate, diisopropyl hydroxymalonate, allyl formate, allyl acetate, allyl glycolate, allyl glyoxylate, diallyl oxalate, allyl propionate, allyl lactate, allyl 2,3-dihydroxypropionate, allyl pyruvate, allyl acrylate, diallyl malonate, diallyl hydroxymalonate, glycerol formal, 4-(hydroxymethyl)-l,3- dioxolan-2-one, 4-methyl-l,3-dioxolane, (2,2-dimethyl-l,3-dioxolan-4-yl)methanol, 1,4- dioxaspiro[4.5]decane-2-methanol, glyceraldehyde, 2,2-dimethyl- 1 ,3-dioxolane-4- carbaldehyde,l,4-dioxaspiro[4.5]decane-2-carbaldehyde, glycidol, glycidyl methyl ether, glycidyl ethyl ether, glycidyl n-propyl ether, glycidyl isopropyl ether, glycidyl n-butyl ether, glycidyl isobutyl ether, glycidyl sec -butyl ether, glycidyl tert-butyl ether, glycidyl allyl ether, glycidyl propargyl ether, glycidyl hexadecyl ether, glycidyl octyl/decyl ether, glycidyl phenyl ether, glycidyl benzyl ether, glycidyl formate, glycidyl acetate, glycidyl propionate, glycidyl isopropionate, glycidyl n-butyrate, glycidyl isobutyrate, glycidyl sec-butyrate, glycidyl acrylate, glycidyl methacrylate, diglycidyl 1,2-cyclohexanedicarboxylate, glycidyl benzoate, glycidyl 4- nitrobenzoate, epichlorohydrin, epibromohydrin, ribitol, arabitol, xylitol, mannitol, sorbitol, galactitol, allitol, iditol, and bis-(2,2-dimethyl-(l,3)dioxolan-4-yl methanol. This production of biobased chemicals 50 as described herein can allow for both the utilization of a renewable, carbonaceous by-product in the production of value-added chemicals and biobased products and an even greener biodiesel production 60 process.

[0161] The flow diagrams depicted herein are provided merely as an example to clearly and concisely describe embodiments of the method within the scope of the present invention. Some steps may be skipped or modified, new steps may be added, existing steps may be deleted, or the order of steps may be altered from that shown in the flow diagrams without departing from the scope of the present invention. It will be apparent to those skilled in the art that the above methods may incorporate changes and modifications without departing from the general scope of the appended claims or the equivalents thereof. It is intended to include all such modifications and alterations in so far as they come within the scope of the appended claims or the equivalents thereof.