LUO LUBIN (US)
LOPEZ-BARRON CARLOS (US)
ROHDE BRIAN (US)
DAVIS MARK (US)
RAUSHEL FRANK (US)
YANG YONG (US)
GALUSKA ALAN (US)
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CLAIMS We claim: 1. A process for producing a cyclic olefin, the process comprising: introducing a polymer to a metathesis catalyst in a reaction vessel under reaction conditions; and obtaining a product comprising the cyclic olefin. 2. The process of claim 1, wherein the polymer is an unsaturated polymer. 3. The process of claim 2 or 3, wherein the unsaturated polymer is selected from the group consisting of a polypentenamer, a polyhexenamer, a polyheptenamer, a polyoctenamer, a polynonenamer, a polydecenamer, a polyundecenamer, a polydodecenamer, a polytridecenamer, a polytetradecenamer, a polypentadecenamer, and copolymers thereof. 4. The process of claim 3, wherein the unsaturated polymer is a polypentenamer, polyoctenamer, or copolymer thereof. 5. The process of any preceding claim, wherein the reaction conditions comprise one or more of: the reaction vessel has a temperature of about 55°C to about 200°C; the reaction vessel has a pressure of about 0.1 psig to about 1,000 psi (about 0.7 kPa to about 6.9 MPa); or a residence time of about 0.25 seconds to about 5 hours. 6. The process of claim 2, 3, 4, or 5, wherein the catalyst is present at from 0.001 nanomoles of transition metal per mole of unsaturated polymer to 1 millimole of transition metal per mole of unsaturated polymer, based upon the moles of unsaturated polymer. 7. The process of any preceding claim, wherein a molar ratio of monomer units of the polymer to catalyst is from about 1000:1 to about 1,000,000:1. 8. The process of any preceding claim, wherein the process is performed free of diluent present in the reaction vessel. 9. The process of any preceding claim, wherein the process is performed with the reaction vessel comprising an oil or wax. 10. The process of claim 9, wherein the process is performed with the reaction vessel comprising the wax, the wax having: a density of from about 0.7 g/cm3 (at 100°C) to about 0.95 g/cm3 (at 100°C) according to ASTM D4052; a kinematic viscosity of from 5 mm2/s (at 100°C) to about 30 mm2/s (at 100°C) according to ASTM D341; and a melting point of from about 25°C to about 100°C according to ASTM D87, a melting point of from about 25°C to about 100°C. 11. The process of any preceding claim, wherein the metathesis catalyst has an activity of about 800 or greater g-cyclic olefin/g-catalyst/hour. 12. The process of any preceding claim, wherein introducing further comprises introducing an isomerization catalyst to the polymer, wherein the metathesis catalyst is different than the isomerization catalyst. 13. The process of any preceding claim, wherein obtaining the product comprises obtaining the cyclic olefin in greater than 90 mol% yield, based on the amount of the polymer. 14. The process of any preceding claim, wherein the product has: a linear olefin content, based on the weight of the product, of less than about 2 wt%; a saturated cycloalkane content, based on the weight of the product, of less than about 2 wt%; and a saturated linear alkane content, based on the weight of the product, of less than about 2 wt%. 15. A method comprising: introducing a recycled cyclic olefin to a metathesis catalyst in a reaction vessel under polymerization reaction conditions and producing a product that includes a polymer. 16. The method of claim 15, wherein the polymer has a molecular weight greater than 300 kDa and less than 1000 kDa. 17. The method of claim 15 or 16, wherein the metathesis catalyst is a Grubbs or Schrock catalyst. 18. The method of claim 15, 16, or 17, wherein the recycled cyclic olefin is a recycled cyclopentene and the polymer is polypentenamer. 19. The method of claim 15, 16, 17, or 18, wherein the reaction conditions include performing ring-opening metathesis polymerization. 20. The method of claim 15, 16, 17, 18, or 19, wherein the metathesis catalyst includes ruthenium. |
[0111] In some embodiments, depolymerization catalysts of the present disclosure may be capable of performing isomerization processes as well as depolymerization. [0112] Depolymerization catalysts of the present disclosure for forming cyclic olefins can be metathesis catalysts. In some embodiments, the metathesis catalyst is represented by the Formula (VI): where M is a Group 8 metal, such as Ru or Os, such as Ru; X and X 1 are, independently, any anionic ligand, such as a halogen (such as chlorine), an alkoxide or a triflate, or X and X 1 may be joined to form a dianionic group and may form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non- hydrogen atoms; L and L 1 are, independently, a neutral two electron donor, such as a phosphine or a N-heterocyclic carbene, L and L 1 may be joined to form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms; L and X may be joined to form a multidentate monoanionic group and may form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms; L 1 and X 1 may be joined to form a multidentate monoanionic group and may form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms; R 4 and R 5 are, independently, hydrogen or C 1 to C 30 substituted or unsubstituted hydrocarbyl (such as a C 1 to C 30 substituted or unsubstituted alkyl or a substituted or unsubstituted C 4 to C 30 aryl); R 5 and L 1 or X 1 may be joined to form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms; and R 4 and L or X may be joined to form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms. [0113] Example alkoxides include those where the alkyl group is a phenol, substituted phenol (where the phenol may be substituted with up to 1, 2, 3, 4, or 5 C 1 to C 12 hydrocarbyl groups) or a C 1 to C 10 hydrocarbyl, such as a C 1 to C 10 alkyl group, such as methyl, ethyl, propyl, butyl, or phenyl. [0114] Example phosphines are represented by the formula: PR 3 ' R 4 ' R 5 ', where R 3 ' is a secondary alkyl or cycloalkyl (such as a C 3 to C 12 secondary alkyl or cycloalkyl), and R 4 ' and R 5' are aryl, C 1 to C 10 primary alkyl, secondary alkyl, or cycloalkyl. R 4 ' and R 5 ' may be the same or different. Example phosphines can include P(cyclohexyl) 3 , P(cyclopentyl) 3 , and/or P(isopropyl) 3 . [0115] Example triflates are represented by the Formula (VII): where R A is hydrogen or a C 1 to C 30 hydrocarbyl group, such as a C 1 to C 12 alkyl group, such as methyl, ethyl, propyl, butyl, or phenyl. [0116] Example N-heterocyclic carbenes are represented by the Formula (VIII) or the Formula (IX): or where each R B is independently a hydrocarbyl group or substituted hydrocarbyl group having 1 to 40 carbon atoms, such as methyl, ethyl, propyl, butyl (including iso-butyl and n-butyl), pentyl, cyclopentyl, hexyl, cyclohexyl, octyl, cyclooctyl, nonyl, decyl, cyclodecyl, dodecyl, cyclododecyl, mesityl, adamantyl, phenyl, benzyl, tolulyl, chlorophenyl, phenol, substituted phenol, or CH 2 C(CH 3 ) 3 ; and each R C is hydrogen, a halogen, or a C 1 to C 12 hydrocarbyl group, such as hydrogen, bromine, chlorine, methyl, ethyl, propyl, butyl, or phenyl. [0117] In other useful embodiments, one of the N groups bound to the carbene in Formula (VIII) or (IX) is replaced with an S, O, or P atom, such as an S atom. [0118] Other useful N-heterocyclic carbenes and their heavier analogues include the compounds described in Hermann, W. A. Chem. Eur. J., 1996, 2, pp. 772 and 1627; Enders, D. et al. Angew. Chem. Int. Ed., 1995, 34, pg.1021; Alder R. W., Angew. Chem. Int. Ed., 1996, 35, pg. 1121; Bertrand, G. et al., Chem. Rev., 2000, 100, pg. 39, and Zabula, A. V. et al., Eur. J. Inorg. Chem.2008, pg.5165. [0119] In at least one embodiment, the metathesis catalyst is one or more of tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazo l-2-ylidene][3-phenyl-1H- inden-1-ylidene]ruthenium(II) dichloride, tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis( 2,4,6-trimethylphenyl)-4,5- dihydro-imidazol-2-ylidene]ruthenium(II) dichloride, tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-di hydroimidazol-2- ylidene][(phenylthio)methylene]ruthenium(II) dichloride, bis(tricyclohexylphosphine)-3-phenyl-1H-inden-1-ylideneruthe nium(II) dichloride, 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene [2-(i-propoxy)-5-(N,N- dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride, or [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]-[2-[[ (4-methylphenyl)imino]methyl]- 4-nitrophenolyl]-[3-phenyl-1H-inden-1-ylidene]ruthenium(II) chloride. [0120] In at least one embodiment, the catalyst is 1,3-bis(2,4,6-trimethylphenyl)-4,5- dihydroimidazol-2-ylidene[2-(i-propoxy)-5-(N,N- dimethylaminosulfonyl)phenyl]methyleneruthenium(II) dichloride and/or tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis( 2,4,6-trimethylphenyl)-4,5- dihydroimidazol-2-ylidene]ruthenium(II) dichloride. [0121] In another embodiment, the metathesis catalyst is represented by Formula (VI) above, where: M is Os or Ru; R 5 is hydrogen; X and X 1 may be different or the same and are any anionic ligand; L and L 1 may be different or the same and are any neutral electron donor; and R 4 may be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. R 4 can be hydrogen, C 1 to C 20 alkyl, or aryl. The C 1 to C 20 alkyl may optionally be substituted with one or more aryl, halide, hydroxy, C 1 to C 20 alkoxy, or C 2 to C 20 alkoxycarbonyl groups. The aryl may optionally be substituted with one or more C 1 to C 20 alkyl, aryl, hydroxyl, C 1 to C 5 alkoxy, amino, nitro, or halide groups. L and L 1 can be phosphines of the formula PR 3 ' R 4 ' R 5 ', where R 3 ' is a secondary alkyl or cycloalkyl, and R 4 ' and R 5' are aryl, C 1 to C 10 primary alkyl, secondary alkyl, or cycloalkyl. R 4 ' and R 5 ' may be the same or different. L and L 1 can be the same and are -P(cyclohexyl) 3 , -P(cyclopentyl) 3 , or -P(isopropyl) 3 . X and X 1 can be the same and can be chlorine. [0122] In another embodiment, the metathesis catalyst is a ruthenium and/or osmium carbene compound represented by the Formula (X): where M is Os or Ru, such as Ru; X, X 1 , L, and L 1 are as described above for Formula (X); and R 9 and R 10 may be different or the same and may be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The R 9 and R 10 groups may optionally include one or more of the following functional groups: alcohol, thiol, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, carboalkoxy, and halogen groups. Such compounds and their synthesis are described in, inter alia, U.S. Patent No.6,111,121. [0123] In another embodiment, the metathesis catalyst useful herein may be any of the catalysts described in US Patent Nos.6,111,121; 5,312,940; 5,342,909; 7,329,758; 5,831,108; 5,969,170; 6,759,537; 6,921,735; and US Patent Publication No.2005-0261451 A1, including, but not limited to, benzylidene-bis(tricyclohexylphosphine)dichlororuthenium, benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2 imidazolidinylidene]dichloro (tricyclohexyl phosphine) ruthenium, dichloro(o-isopropoxyphenylmethylene)(tricyclohexylphosphine )ruthenium(II), (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichl oro(o- isopropoxyphenylmethylene)ruthenium, 1,3-bis(2-methylphenyl)-2-imidazolidinylidene]dichloro(2-iso propoxyphenylmethylene) ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichlo ro[3-(2- pyridinyl)propylidene]ruthenium(II), [1,3-bis(2-methylphenyl)-2-imidazolidinylidene]dichloro(phen ylmethylene) (tricyclohexylphosphine)ruthenium(II), [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichlo ro(3-methyl-2-butenylidene) (tricyclohexylphosphine)ruthenium(II), and [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichlo ro(benzylidene)bis(3- bromopyridine)ruthenium(II). [0124] In another embodiment, the metathesis catalyst is represented by the formula (XI):
where M* is a Group 8 metal, such as Ru or Os, such as Ru; X* and X 1 * are, independently, any anionic ligand, such as a halogen (such as chlorine), an alkoxide or an alkyl sulfonate, or X* and X 1* may be joined to form a dianionic group and may form a single ring of up to 30 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms; L* is N-R**, O, P-R**, or S, such as N-R** or O (R** is a C 1 to C 30 hydrocarbyl or substituted hydrocarbyl, such as methyl, ethyl, propyl or butyl); R* is hydrogen or a C 1 to C 30 hydrocarbyl or substituted hydrocarbyl, such as methyl; R 1 *, R 2 *, R 3 *, R 4 *, R 5 *, R 6 *, R 7 *, and R 8 * are, independently, hydrogen or a C 1 to C 30 hydrocarbyl or substituted hydrocarbyl, such as methyl, ethyl, propyl or butyl, such as R 1 *, R 2 *, R 3 *, and R 4 * are methyl; each R 9 * and R 13 * are, independently, hydrogen or a C 1 to C 30 hydrocarbyl or substituted hydrocarbyl, such as a C 2 to C 6 hydrocarbyl, such as ethyl; R 10 *, R 11 *, R 12 * are, independently hydrogen or a C 1 to C 30 hydrocarbyl or substituted hydrocarbyl, such as hydrogen or methyl; each G, is, independently, hydrogen, halogen or C 1 to C 30 substituted or unsubstituted hydrocarbyl (such as a C 1 to C 30 substituted or unsubstituted alkyl or a substituted or unsubstituted C 4 to C 30 aryl); and where any two adjacent R groups may form a single ring of up to 8 non-hydrogen atoms or a multinuclear ring system of up to 30 non-hydrogen atoms. [0125] Any two adjacent R groups may form a fused ring having from 5 to 8 non-hydrogen atoms. The non-hydrogen atoms may be C and/or O. The adjacent R groups may form fused rings of 5 to 6 ring atoms, such as 5 to 6 carbon atoms. By adjacent is meant any two R groups located next to each other, for example R 3 * and R 4 * can form a ring and/or R 11 * and R 12 * can form a ring. [0126] In at least one embodiment, the metathesis catalyst compound comprises one or more of: 2-(2,6-diethylphenyl)-3,5,5,5-tetramethylpyrrolidine[2-(i-pr opoxy)-5-(N,N-dimethylamino sulfonyl)phenyl]methylene ruthenium dichloride; 2-(mesityl)-3,3,5,5-tetramethylpyrrolidine[2-(i-propoxy)-5-( N,N-dimethylaminosulfonyl) phenyl]methylene ruthenium dichloride; 2-(2-isopropyl)-3,3,5,5-tetramethylpyrrolidine[2-(i-propoxy) -5-(N,N-dimethylaminosulfonyl) phenyl]methylene ruthenium dichloride; 2-(2,6-diethyl-4-fluorophenyl)-3,3,5,5-tetramethylpyrrolidin e[2-(i-propoxy)-5-(N,N- dimethylaminosulfonyl)phenyl]methylene ruthenium dichloride; or mixtures thereof. [0127] For further information on such metathesis catalysts, please see USSN 12/939054, filed November 3, 2010, claiming priority to and the benefit of USSN 61/259,514, filed November 9, 2009. Many of the above named catalysts are generally available from Sigma- Aldrich Corp. (St. Louis, MO) or Strem Chemicals, Inc. (Newburyport, MA). [0128] In at least one embodiment, a metathesis catalyst includes: a Group 8 metal complex represented by the Formula (XII): wherein M" is a Group 8 metal (such as M is ruthenium or osmium, such as ruthenium); each X" is independently an anionic ligand (such as selected from the group consisting of halides, alkoxides, aryloxides, and alkyl sulfonates, such as a halide, such as chloride); R" 1 and R" 2 are independently selected from the group consisting of hydrogen, a C 1 to C 30 hydrocarbyl, and a C 1 to C 30 substituted hydrocarbyl (such as R" 1 and R" 2 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, sec-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, cyclooctyl, and substituted analogs and isomers thereof, such as selected from the group consisting of tert- butyl, sec-butyl, cyclohexyl, and cyclooctyl); R" 3 and R" 4 are independently selected from the group consisting of hydrogen, C 1 to C 12 hydrocarbyl groups, substituted C 1 to C 12 hydrocarbyl groups, and halides (such as R" 3 and R" 4 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, sec-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, cyclooctyl, and substituted analogs and isomers thereof, such as selected from the group consisting of tert-butyl, sec-butyl, cyclohexyl, and cyclooctyl); and L" is a neutral donor ligand, such as L" is selected from the group consisting of a phosphine, a sulfonated phosphine, a phosphite, a phosphinite, a phosphonite, an arsine, a stibine, an ether, an amine, an imine, a sulfoxide, a carboxyl, a nitrosyl, a pyridine, a thioester, a cyclic carbene, and substituted analogs thereof; such as a phosphine, a sulfonated phosphine, an N-heterocyclic carbene, a cyclic alkyl amino carbene, and substituted analogs thereof (such as L" is selected from a phosphine, an N-heterocyclic carbene, a cyclic alkyl amino carbene, and substituted analogs thereof). [0129] A "cyclic carbene" may be defined as a cyclic compound with a neutral dicoordinate carbon center featuring a lone pair of electrons. Such cyclic carbenes may be represented by the Formula (XIII) below: where n is a linking group comprising from one to four ring atoms selected from the group consisting of C, Si, N, P, O, and S, with available valences optionally occupied by H, oxo, hydrocarbyl, or substituted hydrocarbyl groups; such as n comprises two ring atoms of carbon with available valences occupied by H, oxo, hydrocarbyl or substituted hydrocarbyl groups; such as n is C 2 H 2 , C 2 H 4 , or substituted versions thereof; each E is independently selected from the group comprising C, N, S, O, and P, with available valences optionally occupied by Lx, Ly, Lz, and Lz'; such as at least one E is a C; such as one E is a C and the other E is a N; such as both E's are C; and Lx, Ly, Lz, and Lz' are independently selected from the group comprising hydrogen, hydrocarbyl groups, and substituted hydrocarbyl groups; such as Lx, Ly, Lz, and Lz' are independently selected from the group comprising a hydrocarbyl group and substituted hydrocarbyl group having 1 to 40 carbon atoms; such as Lx, Ly, Lz, and Lz' are independently selected from the group comprising C 1-10 alkyl, substituted C 1-10 alkyl, C 2-10 alkenyl, substituted C 2-10 alkenyl, C 2-10 alkynyl, substituted C 2-10 alkynyl, aryl, and substituted aryl; such as Lx, Ly, Lz, and Lz' are independently selected from the group comprising methyl, ethyl, propyl, butyl (including isobutyl and n-butyl), pentyl, cyclopentyl, hexyl, cyclohexyl, octyl, cyclooctyl, nonyl, decyl, cyclodecyl, dodecyl, cyclododecyl, mesityl, adamantyl, phenyl, benzyl, tolulyl, chlorophenyl, 2,6-diethylphenyl, 2,6-diisopropylphenyl, 2-isopropylphenyl, 2-ethyl-6-methylphenyl, 3,5-ditertbutylphenyl, 2-tertbutylphenyl, and 2,3,4,5,6- pentamethylphenyl. Useful substituents include C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, C 1-10 alkoxy, C 2-10 alkenyloxy, C 2-10 alkynyloxy, aryloxy, C 2-10 alkoxycarbonyl, C 1-10 alkylthio, C 1-10 alkylsulfonyl, fluoro, chloro, bromo, iodo, oxo, amino, imine, nitrogen heterocycle, hydroxy, thiol, thiono, phosphorous, and carbene groups. [0130] Examples of cyclic carbenes useful in embodiments include: where Lx, Ly, and Lz are as defined above. In some embodiments, at least two of Lx, Ly, Lz, and Lz' may be joined to form a 3- to 12-membered spirocyclic ring, with available valences optionally occupied by H, oxo, halogens, hydrocarbyl or substituted hydrocarbyl groups. Useful substituents include C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, C 1-10 alkoxy, C 2-10 alkenyloxy, C 2-10 alkynyloxy, aryloxy, C 2-10 alkoxycarbonyl, C 1-10 alkylthio, C 1-10 alkylsulfonyl, fluoro, chloro, bromo, iodo, oxo, amino, imine, nitrogen heterocycle, hydroxy, thiol, thiono, phosphorous, and carbene groups. [0131] Example cyclic carbenes include N-heterocyclic carbenes (NHCs). For purposes of the present disclosure, NHCs are cyclic carbenes of the types described in Formula (XIII) above, where each E is N and the available valences on the N are occupied by Lx and Ly. Example NHCs may be represented by the formula: where n, Lx, and Ly are as described above in Formula (XIII). [0132] Some particularly useful NHCs include: where Lx and Ly are as described above. Other useful NHCs include the compounds described in Hermann, W. A. Chem. Eur. J.1996, 2, 772 and 1627; Enders, D. et al., Angew. Chem. Int. Ed. 1995, 34, 1021; Alder R. W., Angew. Chem. Int. Ed. 1996, 35, 1121; USSN 61/314,388; and Bertrand, G. et al., Chem. Rev.2000, 100, 39. [0133] Example cyclic carbenes include cyclic alkyl amino carbenes (CAACs). In all embodiments herein, CAACs are cyclic carbenes of the types described in Formula (XIII) above, where one E is N and the other E is C, and the available valences on the N and C are occupied by Lx, Ly, and Lz. CAACs may be represented by the formula: where n, Lx, Ly, and Lz are as described above in Formula (XIII). [0134] Some particularly useful CAACs include: . [0135] Other useful CAACs include the compounds described in US Patent No.7,312,331; USSN 61/259,514; and Bertrand et al, Angew. Chem. Int. Ed., 2005, 44, 7236-7239. [0136] Other carbenes useful in embodiments of the present disclosure include thiazolyidenes, P-heterocyclic carbenes (PHCs), and cyclopropenylidenes. [0137] With respect to Group 8 metal complexes of Formula (XII), the phosphine ligands (PHR" 3 R" 4 ) and L" are neutral donor ligands. In some embodiments, L" may be a phosphine having a formula PHR" 5 R" 6 . In such embodiments, the Group 8 metal complex may be represented by the Formula (XIV): wherein M" is a Group 8 metal (such as M is ruthenium or osmium, such as ruthenium); each X" is independently an anionic ligand (such as selected from the group consisting of halides, alkoxides, aryloxides, and alkyl sulfonates, such as a halide, such as chloride); R" 1 and R" 2 are independently selected from the group consisting of hydrogen, a C 1 to C 30 hydrocarbyl, and a C 1 to C 30 substituted hydrocarbyl (such as R" 1 and R" 2 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, sec-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, cyclooctyl, and substituted analogs and isomers thereof, such as selected from the group consisting of tert- butyl, sec-butyl, cyclohexyl, and cyclooctyl); and R" 3 , R" 4 , R" 5 , and R" 6 are independently selected from the group consisting of hydrogen, C 1 to C 12 hydrocarbyl groups, substituted C 1 to C 12 hydrocarbyl groups, and halides (such as R" 3 , R" 4 , R" 5 , and R" 6 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, sec-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, cyclooctyl, and substituted analogs and isomers thereof, such as selected from the group consisting of tert-butyl, sec-butyl, cyclohexyl, and cyclooctyl). [0138] With respect to embodiments where L" is a phosphine having a formula PHR" 5 R" 6 , in some embodiments, at least one phosphine ligand is a secondary phosphine ligand. In such embodiments, where at least one of the neutral donor ligands is a secondary phosphine ligand, R" 3 and R" 4 or R" 5 and R" 6 are selected from the group consisting of C 1 to C 12 hydrocarbyl groups, substituted C 1 to C 12 hydrocarbyl groups, and halides. In particular embodiments, both donor ligands are secondary phosphine ligands and R" 3 , R" 4 , R" 5 , and R" 6 are selected from the group consisting of C 1 to C 12 hydrocarbyl groups, substituted C 1 to C 12 hydrocarbyl groups, and halides. [0139] With respect to embodiments where L" is a phosphine having a formula PHR" 5 R" 6 , in particular embodiments, at least one donor ligand is a primary phosphine ligand. In such embodiments where at least one of the phosphine ligands is a primary phosphine ligand, one of R" 3 and R" 4 or one of R" 5 and R" 6 is selected from the group consisting of C 1 to C 12 hydrocarbyl groups, substituted C 1 to C 12 hydrocarbyl groups, and halides. In particular embodiments, both donor ligands are primary phosphine ligands and one of R" 3 and R" 4 and one of R" 5 and R" 6 is selected from the group consisting of C 1 to C 12 hydrocarbyl groups, substituted C 1 to C 12 hydrocarbyl groups, and halides. [0140] In some embodiments, R" 3 and R" 4 form a ring. With respect to embodiments where L" is a phosphine having a formula PHR" 5 R" 6 , in particular embodiments, R" 5 and R" 6 form a ring. In yet other embodiments, R" 3 and R" 4 form a ring and R" 5 and R" 6 form a ring. In other embodiments, R" 3 and at least one of R" 5 and R" 6 may form a ring, thereby forming a chelating phosphine ligand. In other embodiments, R" 4 and at least one of R" 5 and R" 6 may form a ring, thereby forming a chelating phosphine ligand. [0141] In particular embodiments, the Group 8 metal complex is selected from: [(HP(tert-butyl) 2 ) 2 Ru(C 5 H 8 )Cl 2 ], [(H 2 P(tert-butyl)) 2 Ru(C 5 H 8 )Cl 2 ], [(HP(cyclohexyl) 2 ) 2 Ru(C 5 H 8 )Cl 2 ], [(H 2 P(cyclohexyl)) 2 Ru(C 5 H 8 )Cl 2 ], [(HP(cyclopentyl) 2 ) 2 Ru(C 5 H 8 )Cl 2 ], [(H 2 P(cyclopentyl)) 2 Ru(C 5 H 8 )Cl 2 ], [(HP(n-butyl) 2 ) 2 Ru(C 5 H 8 )Cl 2 ], [(H 2 P(n-butyl)) 2 Ru(C 5 H 8 )Cl 2 ], [(HP(sec-butyl) 2 ) 2 Ru(C 5 H 8 )Cl 2 ], [(H 2 P(sec-butyl)) 2 Ru(C 5 H 8 )Cl 2 ], and fluoride and bromide derivatives thereof (such as wherein the Cl 2 in the above list is replaced with F 2 , Br 2 , ClF, ClBr or FBr). [0142] In some embodiments, the metathesis catalyst may be selected from those described in US 8,329,921; US 8,519,147; US 2011/0112349; US 8,809,563; US 9,024,034; US 8,557,902; US 2012/0077945; US 8,524930; US 9,181,360; US 8,623,962; US 8,063,232; US 8,604,148; and US 9,714,393. [0143] In certain embodiments, the catalyst employed in the process of the present disclosure may be bound to or deposited onto a solid support. In particular, the metathesis catalyst may be bound to or deposited onto a solid support, which may simplify catalyst recovery. In addition, the support may increase catalyst strength and attrition resistance. Suitable catalyst supports include, without limitation, silicas; aluminas; silica-aluminas; aluminosilicates, including zeolites and other crystalline porous aluminosilicates; as well as titanias; zirconia; magnesium oxide; carbon; and cross-linked polymeric resins, such as functionalized cross-linked polystyrenes, e.g., chloromethyl-functionalized cross-linked polystyrenes; such as silica or alumina. The metathesis catalyst may be deposited onto the support by any method known to those skilled in the art, including, for example, impregnation, ion-exchange, deposition-precipitation, and vapor deposition. Alternatively, a component of the catalyst, such as the metathesis catalyst, may be chemically bound to the support via one or more covalent chemical bonds, for example, the catalyst may be immobilized by one or more covalent bonds with one or more of substituents of a ligand of the metathesis catalyst. For example, the metathesis catalyst may be deposited onto a silica support. Further, the metathesis catalyst may be preloaded onto the solid support before forming the catalyst. Alternatively, the supported catalyst may be generated in situ. [0144] If a catalyst support is used, the catalyst compound may be loaded onto the catalyst support in any amount, provided that the metathesis process of the present disclosure proceeds to the metathesis products. Generally, the catalyst compound is loaded onto the support in an amount based on the weight of the transition metal, such as the Group 8 metal, such as ruthenium or osmium, relative to the total weight of the catalysts plus support. The catalyst compound may be loaded onto the support in an amount greater than about 0.01 wt% of the Group 8 metal, based upon the weight of the catalysts plus support and such as greater than about 0.05 wt% of the Group 8 metal. Generally, the catalyst compound is loaded onto the support in an amount that is less than about 20 wt% of the Group 8 metal, and such as less than about 10 wt% of the Group 8 metal. [0145] In embodiments where the catalyst compound utilized in a method of the present disclosure is bound to or deposited on a solid catalyst support, the solid catalyst support will render the catalyst compound heterogeneous. [0146] In certain embodiments, the catalyst employed in the process of the present disclosure is metal-oxide based heterogeneous catalyst. In particular, the metathesis catalyst may be WO 3 /Al 2 O 3 , MoO 3 /Al 2 O 3 , WO 3 /SiO 2 , MoO 3 /SiO 2 , supported Re 2 O 7 , or a combination thereof. Isomerization Catalysts [0147] As mentioned above, an isomerization catalyst can be used in addition to the ring closing metathesis catalyst. Isomerization catalysts may include RCM catalysts, such as ruthenium-based catalysts, their decomposed forms featuring Ru-hydride moieties and/or ruthenium metal species, such as nanoparticles. The isomerization role of metathetically active ruthenium compounds and products of their decomposition or deactivation is described in Fogg, D. E. et al., ChemCatChem, 2016, 8, 2446 (Catalyst Decomposition during Olefin Metathesis Yields Isomerization‐Active Ruthenium Nanoparticles) and Jensen, V. R., J. Am. Chem. Soc., 2017, 139, 16609 (Loss and Reformation of Ruthenium Alkylidene: Connecting Olefin Metathesis, Catalyst Deactivation, Regeneration, and Isomerization), Grela, K. et al., Chem. Eur. J,.2018, 24, 10403 (Sequential Alkene Isomerization and Ring-Closing Metathesis in Production of Macrocyclic Musks from Biomass). [0148] The isomerization catalysts may also be well-defined metal complexes, such as metal hydrides supported by organic ligand frameworks or the complexes where active hydride species are generated in situ. [0149] The isomerization catalysts may be heterogeneous catalysts, such as solid acid catalysts or metal hydrides. [0150] In at least one embodiment, an isomerization catalyst is selected from: [Fe(CO) 5 ], [Fe 3 (CO) 12 ], [RhCl(PPh 3 ) 3 ], [Pd(NCPh) 2 Cl 2 ], [HRuCl(PPh 3 )3], [HNi(PPh 3 ) 3 ]Cl, [HNi(PCy3) 2 Cl], [HCo(CO)4], Tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazo l-2-ylidene][3-phenyl-1H- inden-1-ylidene]ruthenium(II) dichloride, or combination(s) thereof. Cyclic Olefin Products [0151] Cyclic olefin products of the present disclosure can include substituted or unsubstituted cyclic olefins selected from C5-C50 cyclic olefins, such as C5-C40 cyclic olefins, such as C 5 -C 30 cyclic olefins, such as C 5 -C 20 cyclic olefins, such as C 6 -C 15 cyclic olefins, such as C6-C10 cyclic olefins, such as C7-C9 cyclic olefins, alternatively C5-C7 cyclic olefins. Cyclic olefins of the present disclosure can monoolefins, diolefins, or triolefins. In at least one embodiment, a cyclic olefin is a monoolefin. [0152] In some embodiments, a cyclic olefin is a monoolefin selected from cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, cycloundecene, cyclododecene, cyclotridecene, cyclotetradecene, cyclopentadecene, cyclohexadecene, cycloheptadecene, cyclooctadecene, cyclononadecene, cycloicosene, cycloheneicosene, cyclodocosene, cyclotricosene, cyclotetracosene, cyclopentacosene, cyclohexacosene, cycloheptacosene, cyclooctacosene, cyclononacosene, cyclotriacontene, methyl-containing derivatives thereof, ethyl-containing derivatives thereof, vinyl- or vinylidene-containing derivatives thereof, and combination(s) thereof. [0153] In some embodiments, a cyclic olefin is a diolefin selected from cyclopentadiene, cyclohexadiene, cycloheptadiene, cyclooctadiene, cyclononadiene, cyclodecadiene, cycloundecadiene, cyclododecadiene, cyclotridecadiene, cyclotetradecadiene, cyclopentadecadiene, cyclohexadecadiene, cycloheptadecadiene, cyclooctadecadiene, cyclononadecadiene, cycloicosadiene, cycloheneicosadiene, cyclodocosadiene, cyclotricosadiene, cyclotetracosadiene, cyclopentacosadiene, cyclohexacosadiene, cycloheptacosadiene, cyclooctacosadiene, cyclononacosadiene, cyclotriacontadiene, methyl- containing derivatives thereof, ethyl-containing derivatives thereof, vinyl- or vinylidene- containing derivatives thereof, and combination(s) thereof, and combination(s) thereof. [0154] For high yielded processes of the present disclosure, a product formed can be a mixture of cyclic olefin(s), optionally some saturated cycloalkanes, optionally some linear olefins, and optionally some saturated alkanes. In some embodiments, a product has a linear olefin content, based on the weight of the product, of less than about 10 wt%, such as less than about 5 wt%, such as less than about 2 wt%, such as less than about 1 wt%, such as less than about 0.5 wt%, such as less than about 0.1 wt%, such as 0 wt%. For example, a product can have a linear olefin content of about 0.1 wt% to about 10 wt%, such as about 0.1 wt% to about 5 wt%, such as about 0.1 wt% to about 1 wt%, such as about 0.1 wt% to about 0.5 wt%, such 0 wt%. In some embodiments, a product has a saturated cycloalkane content, based on the weight of the product, of less than about 10 wt%, such as less than about 5 wt%, such as less than about 2 wt%, such as less than about 1 wt%, such as less than about 0.5 wt%, such as less than about 0.1 wt%, such as 0 wt%. For example, a product can have a saturated cycloalkane content of about 0.1 wt% to about 10 wt%, such as about 0.1 wt% to about 5 wt%, such as about 0.1 wt% to about 1 wt%, such as about 0.1 wt% to about 0.5 wt%, such 0 wt%. In some embodiments, a product has a saturated linear alkane content, based on the weight of the product, of less than about 10 wt%, such as less than about 5 wt%, such as less than about 2 wt%, such as less than about 1 wt%, such as less than about 0.5 wt%, such as less than about 0.1 wt%, such as 0 wt%. For example, a product can have a saturated linear alkane content of about 0.1 wt% to about 10 wt%, such as about 0.1 wt% to about 5 wt%, such as about 0.1 wt% to about 1 wt%, such as about 0.1 wt% to about 0.5 wt%, such 0 wt%. [0155] In some embodiments, processes of the present disclosure can provide cyclic olefins having a purity (e.g., cyclic olefin content), as determined by Gas Chromatography (GC), of greater than 90%, such as greater than 95%, such as greater than 98%, such as greater than 99%, such as greater than 99.9%, such as from about 90% to about 99.99%, such as from about 95% to about 99.99%, such as 98% to 99.99%, such as 99% to 99.99%. For example, in some embodiments, cyclic olefin products of the present disclosure can have a cyclic olefin content, based on the weight of the cyclic olefin product, as determined by GC, of greater than 90 wt%, such as greater than 95 wt%, such as greater than 98 wt%, such as greater than 99 wt%, such as greater than 99.9 wt%, such as from about 90 wt% to about 99.99 wt%, such as from about 95 wt% to about 99.99 wt%, such as 98 wt% to 99.99 wt%, such as 99 wt% to 99.99 wt%. Advantageously, high purity of cyclic olefins of the present disclosure can be achieved as a reactor effluent without a need for purification steps (such as distillation). In addition, the high yield of high purity cyclic olefins reduces or eliminates the presence of byproducts having similar or the same boiling point as the desired cyclic olefin(s). For example, distillation of linear olefins from cyclic olefins would otherwise result in a significant loss in the amount of pure cyclic olefin (Register, R. A., ACS Macro Letters, 2017, 6, 112). Side products of conventional manufacturing of cyclopentene by selective hydrogenation of cyclopentadiene, 1,3-pentadienes (cis/trans), have a boiling point (42°C) close to that in cyclopentene (44°C), which makes the separation of cyclopentene from these contaminations challenging even at the industrial scale. Non-cyclic olefin contaminations in cyclic olefins serve as chain transfer agents in ROMP thus reducing molecular weights of the resulting polymer products. De-Polymerization Examples [0156] Solid linear and cured polypentenamers were selectively depolymerized into pure cyclopentene upon mechanical mixing with a solid RCM catalyst (Grubbs 2nd generation, 0.05 mol%). No special pretreatment of polypentenamer samples were conducted prior depolymerization. The yield of reclaimed cyclopentene was 75-93%. Interestingly, the sulfur bridging units in the cured sample did not substantially mitigate the activity of the RCM catalyst. Thus, polypentenamer based tires can be recycled back to monomers in high yields. [0157] The purity of the recycled monomer was found to be about 99.5+% by 1 H NMR spectroscopy and GC analysis. The corresponding polymerization-depolymerization cycle can be used for purifying cyclopentene from contaminants including straight olefins. [0158] For purposes herein, the purity of recycled monomer can be monitored and estimated with 1 H NMR method using a Bruker 400 MHz instrument, as indicated. Pulse program zgcw30 can be used with D 1 = 60s and ns = 2 or 4. CDCl 3 can be the lock solvent. The chemical shift of cyclopentene monomer double bond protons is about 5.75 ppm and the chemical shift of polypentenamer double bond protons is about 5.53 ppm. [0159] Gas chromatography (GC) was performed using an Agilent 6890A instrument with split inlet, flame ionization detector (GC-FID) with helium carrier and a Petrocol DH 150m x 0.25mm x 1μm (MilliporeSigma, USA) with a 100% polydimethyl siloxane phase. The parameters of the GC method includes: 1) Injector: 0.1uL; 2) Inlet: 250C, 20:1 Split, 80psi, He; 3) Oven: 60°C (hold 2 min) to 100°C at 4C/min to 300°C at 15C/min (hold 15min); 4) Column: Ramped pressure 80 psi (hold 12 min) to 100 psi at 3 psi/min, initial flow 3.3mL/min; 5) Detector: 270°C, H 2 flow 40mL/min, Air flow 450mL/min, Make up+Column flow 30mL/min. Depolymerization of Natural and Synthetic Rubbers [0160] The strategy for the recycling of cyclic olefins from natural or synthetic rubbers included the application of a catalyst system(s) with active isomerization and ring-closing metathesis capability, such as a ruthenium based system. As shown in Scheme 1 previously, in the first reaction step the isomerization in polyisoprene gave a structural unit where four single C-C bonds are separated by double bonds. Then, the following ring-closing metathesis reaction for the resulting fragment gives methyl-branched cyclopentene. Subsequent isomerization/RCM cycles can further depolymerize a rubber material with the formation of unsaturated of C 5 cyclics and a conjugated polymer. Preparation of Polypentenamers [0161] Sample 1. Typical procedure for preparation of polypentenamer samples: The catalyst was formed in situ by adding solid (p-MeC6H4O)2AlCl (202 mg, 0.731 mmol) to a solution of WCl6 (145 mg, 0.366 mmol) in toluene (10 mL). After stirring for one hour, the resulting mixture was added to the solution of cyclopentene (99.7 g, 1.464 mol) and triethylaluminum (84 mg, 0.732 mmol) in toluene (600 mL) at 0°C. After 75 min of intense mechanical stirring, a solution of 2,6-di-tert-butyl-4-methylphenol (1.00 g, 4.48 mmol) in 100 mL of ethanol/toluene mixture (1:4, v:v, respectively) was added. The obtained mixture was poured into ethanol (2 L). The precipitated polymer was then washed 3 times with ethanol (250 mL each) and dried under vacuum at 50°C for 4 hours to give 50.7 g of the polymeric product. [0162] Sample 2. The catalyst was formed in situ by adding solid (4-(PhCH2)C6H4O)2AlCl (314 mg, 0.731 mmol) to a solution of WCl 6 (145 mg, 0.366 mmol) in toluene (10 mL). After stirring for one hour at ambient conditions, the resulting mixture was added to a solution containing cyclopentene (first comonomer) (99.6 g, 1.463 mol), triethylaluminum (activator) (83 mg, 0.731 mmol), and toluene (600 mL) at 3°C. A solution of dicyclopentadiene (DCPD) (second comonomer) (1.934 g, 15 mmol) in toluene (64 mL) was slowly added to the reaction mixture over 60 minutes under intense mechanical stirring. After additional 2 hours, a solution of 2,6-di-tert-butyl-4-methylphenol (1.00 g, 4.48 mmol) in 100 mL of ethanol/toluene mixture (1:4, v:v, respectively) was added. The obtained mixture was added to methanol (4 L). The precipitated polymer was washed 3 times with methanol (500 mL each) and dried under vacuum at 55°C for 4 hours to give 55.4 g of the product containing 1.8 mol% of incorporated DCPD according to 1 H NMR spectroscopy (Dragutan et.al. Green Metathesis Chemistry: Great Challenges in Synthesis, Catalysis, and Nanotechnology (2010), 369-380). Depolymerization of polypentenamer [0163] Example 1. Hoveyda-Grubbs catalyst (2 nd generation) was used (also referred to as (1,3-bis-(2,4,6,-trimethylphenyl)-2-imidazolidinylidene)dich loro(o- isopropoxyphenylmethylene)ruthenium). A solution of Hoveyda-Grubbs catalyst (2 nd generation, 15 mg, 0.03 mol%) in 1 mL of toluene was added to solid polypentenamer (Sample 1) in a 100 mL flask. The resulting mixture was stirred at 55-85°C under vacuum in a completely closed system cooled by a liquid nitrogen compartment for collecting volatile depolymerization products. After 2 hour, the depolymerization reaction was visually completed yielding ca 5.60 g of a colorless liquid containing cyclopentene (4.70 g) and toluene (0.90 g) according to 1 H NMR spectroscopy. Total monomer recovery: 75%. [0164] Example 2. Solid Hoveyda-Grubbs catalyst (2 nd Generation, 30 mg, 0.007 mol%) was added to the 1 L 2-necked flask, equipped with a mechanical stirrer and an outlet for removal and subsequent condensation of volatile depolymerization products at -196°C, and containing 50 g of polypentenamer Sample 1. Depolymerization under stirring (60-200 rmp) in vacuo at 70-80°C resulted in almost complete disappearance of the polymer in 4 hours. The monomer was recovered in the yield of 46.1 g (92%). [0165] Example 3. Solid Hoveyda-Grubbs catalyst (2 nd Generation, 30 mg) was added to the 1 L 2-necked flask equipped with a mechanical stirrer and an outlet for removal and subsequent condensation of volatile depolymerization products at -196°C and containing 73 g of polypentenamer Sample 1. Depolymerization was performed under stirring (60-200 rmp) in vacuo at 75°C. Upon depolymerizing of polymer to ca ¼ of its original volume, a fresh portion of polypentenamer was added. Totally, 3 subsequent additions were performed (61 g, 46 g and 27 g) to give 154 g of cyclopentene. Yield: 74.4%. [0166] Control Example 4. Polypentenamer Sample 1 (2 g) was heated up (70-80°C) in vacuo for 3 hours under stirring in the absence of ruthenium catalyst. No depolymerization was observed. These results show that the ROMP catalyst residues are metathetically non- active under those conditions and observed depolymerization in previous Examples was induced by ruthenium-based catalysts only. [0167] Example 5. Cyclopentene obtained in Examples 2 and 3 was combined and distilled. Three fractions were collected: 1 st fraction with the boiling point up to 44°C, ca 4 g; 2 nd fraction with the boiling point 44 - 45°C, 160.8 g; and 3 rd fraction with the boiling point 45 - 50°C, 7.5 g. The GC compositions of all three fractions and crude cyclopentene are summarized in Table 3. Table 3. GC composition for the fractions obtained in Example 5. [0168] Example 6. Solid Hoveyda-Grubbs catalyst (2 nd Generation, 50 mg), polypentenamer Sample 1 (140 g) and 4 mL of SpectraSyn4 (a poly alpha-olefin synthetic base stock commercially available from ExxonMobil Corporation) were added to a 1 L 3-necked flask equipped with a mechanical stirrer and a vacuum condenser cooled by liquid nitrogen. Depolymerization was performed under stirring (60-200 rmp) in vacuo at 75°C. Upon depolymerizing of polymer to ca ¼ of its original volume, a new portion of polypentenamer Sample 1 was added. Totally, 2 subsequent additions were performed (135 g and 55 g, 330 g totally) to give 305 g of crude recovered cyclopentene over 4 hours (yield 92.4%). Distillation afforded 275 g of pure cyclopentene (purity 99.8%, GC). Major components of remaining, undistilled product (30 g) were cyclopentene (92.7%) and cyclohexene (3.85%). Cyclohexene and higher cyclic olefins were formed upon isomerization and subsequent RCM of polypentenamer. The GC compositions of the products, obtained in Example 6 are summarized in Table 4. Overall cyclopentene recovery yield: 302 g (91.6%) Table 4. GC composition for the product obtained in Example 6. Depolymerization of cyclopentene-DCPD copolymer [0169] Example 7. Cyclopentene-dicyclopentadiene copolymer Sample 2 (53 g, cis/trans 18/82%, 1.9 mol% DCPD) was depolymerized using Hoveyda-Grubbs catalyst (2 nd Generation, 45 mg). The 1L flask, equipped with a magnetic stirrer was charged with the copolymer, SpectraSyn4 (5 mL) and attached to a receiving flask over an adaptor arm. The system was evacuated before cooling the receiving flask with liquid nitrogen. Depolymerization was performed at 75°C under static vacuum. Complete disappearance of the polymer was observed in 3 hours. Around 49 g of cyclopentene were obtained. Recovery yield: 96%. The GC compositions of the product is summarized in Table 5. Table 5. GC composition for the product obtained in Example 7. Table 6. Summary of Depolymerization Experiments. Cured polypentenamers [0170] Example 8. Vulcanized/cured polypentenamer sample was prepared in two steps. First, the components listed in Table 7 were mechanically mixed at 80°C using an internal (BrabenderTM) mixer. The compounds were then molded into plaques with thickness = 0.5 mm and cured at 160°C for 25 minutes using a hot press. FIG. 1 is a graph illustrating vulcanization (cure kinetics) curve for the polypentenamer sample measured at 160°C. Dotted lines indicates 100% and 90% cure state. The curing time was enough for 90% cure state of the sample, according to the vulcanization curve data measured in an ARES G2 rheometer (TA InstrumentsTM), and shown in FIG. 1. (In FIG.1, the top most solid line is G* vs. time, and the lower solid line is the temperature vs. time). Table 7. Recipe for polypentenamer vulcanization. [0171] Examples 9-11. Second, vulcanized/cured polypentenamer and blends of polypentenamer with polybutadiene and natural rubber were prepared using a representative truck and bus formulation shown in Table 8. A two stage mixing process, involving a 1 st and 2 nd pass non-productive mix and a 3 rd pass productive mix, was carried out on an IntelliTorque brabender on a 66 gram basis. The 1 st non-productive pass initial conditions were 35 RPMs (round-per-minute) and 75°C for the initial addition of the polymer or polymers. Once the polymer was added to the mixing head, RPMs were increased to 50 , after which half the carbon black loading was added over two minutes of mixing, followed by addition of antioxidant, ZnO, stearic acid, and wax over 30 seconds, followed by the second half of the carbon black loading over 2 minutes. After the second half of the carbon black loading was added, RPMs were increased to 100 and the mixture was allowed to mix for 8 minutes or until a mixture achieved the temperature of 150°C, whichever came first. Then, the polymer mixture was removed (“dumped”) from the brabender and cold pressed. The 2 nd non-productive pass involves an initial brabender condition of 35 RPM and 75°C. Over the 30 seconds the productive mix from the 1 st pass was added back into the brabender. Once added, the RPMs were increased to 100 and the polymer mixture was allowed to mix for 3 minutes or until the polymer mixture reached a temperature of 150°C, after which the mixture was “dumped” and cold pressed. Here the amount of polymer mixture added is denoted as the non-productive master batch. The 3 rd pass productive mix involved an initial brabender setting of 35 RPM and 75°C. The polymer mixture was added over the course of 30 seconds, then the remaining cure package components were added to the polymer mixture in the brabender over the course of 1.5 minutes. After the cure package was added, the RPMs were increased to 50 and allowed to mix for 3 minutes. The RPMs were adjusted to keep the mixing temperature below 100°C. After three minutes the polymer mixture was dumped and cold pressed. The polymer mixture cure kinetics were then determined on a Rubber Process Analyzer (RPA) at 160°C, 1 Hz, and 0.1% strain for 60 minutes. The t90, the time it takes for the torque to increase to 90% of the maximum torque plateau, was determine as defined in ASTM 5289. The polymer mixture was then cured into a mold to its t90 plus 5 minutes at 160°C and then used for depolymerization experiments. [0172] Examples 9-11 were dried in a vacuum oven at 55°C at least 4 hours before depolymerization experiments. Table 8. Recipe for polypentenamer blends vulcanization. Depolymerization of cured polypentenamer [0173] Example 12. Grubbs catalyst (2 nd generation) was used (also referred to as benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2- imidazolidinylidene]dichloro(tricyclohexylphosphine) ruthenium). Solid Grubbs catalyst (2 nd generation, 30 mg, 0.05 mol%) was added to solid cured polypentenamer (Example 8, 5.0 g) in a 100 mL flask. The resulting mixture was stirred at 55-85°C under vacuum in a completely closed system cooled by a liquid nitrogen compartment for collecting volatile depolymerization products. After 4 hours, the depolymerization reaction was visually completed yielding ca 4.65 g of a colorless liquid containing pure cyclopentene. The recycled monomer is pure according to 1 H NMR spectroscopy (FIG.2) and does not contain any traces of saturated cyclics or linear alpha olefins at an 1 H NMR noticeable level. Recovery yield: 93%. [0174] Example 13. Cured polypentenamer (4.62 g, Example 9) and Hoveyda-Grubbs catalyst (2 nd Generation, 30 mg) were combined in 100 mL flask equipped with magnetic stirring and an outlet for removal and subsequent condensation of volatile depolymerization products. Depolymerization under stirring (60-200 rmp) in vacuo at 70-80°C did not give a liquid product. Solid Grubbs catalyst (2 nd generation, 30 mg) was then added and temperature was elevated to 90°C. Colorless liquid (0.7 g) was collected in 2 hours. The resulting recycled monomer consists of pure cyclopentene according to 1 H NMR spectroscopy. Recovery yield: 25.4%. [0175] Example 14. Cured polypentenamer (4.40 g, Example 10, cryogrinded), solid Grubbs catalyst (2 nd Generation, 30 mg) and SpectraSyn4 (4 mL) were combined in 100 mL flask equipped with magnetic stirring and an outlet for removal and subsequent condensation of volatile depolymerization products. Depolymerization under stirring (60-200 rmp) in vacuo at 80°C gave 0.68 g of colorless liquid in 2 hours. Further depolymerization for the remaining mixture was induced upon addition of toluene (ca 11 mL) and Hoveyda-Grubbs catalyst (2 nd generation, 30 mg) and afforded in 2 hours at 80°C a colorless solution (10.6 g) containing 0.41 g of cyclopentene in toluene according to 1 H NMR spectroscopy. Overall recovery yield: 1.09 g (59.2%). The GC composition of both fractions are summarized in Table 9. Table 9. GC composition for the products obtained in Example 14. [0176] Example 15. Cured polypentenamer (10.3 g, Example 11, cryogrinded), solid Hoveyda-Grubbs catalyst (2 nd generation, 40 mg) and SpectraSyn4 (20 mL) were combined in 100 mL flask equipped with magnetic stirring and an outlet for removal and subsequent condensation of volatile depolymerization products. Depolymerization under stirring (60-200 rmp) in vacuo at 75°C gave 1.64 g of colorless liquid in 4 hours consisting of pure cyclopentene according to 1 H NMR spectroscopy. The composition, estimated by GC is summarized in Table 10. Recovery yield: 87%. Table 10. GC composition for the products obtained in Example 15. Table 11. Summary of Depolymerization Experiments for Cured and Blended Polypentenamers. [0177] Overall, processes of the present disclosure can include treating a polymer (such as a polypentenamer or polyoctenamer) with a ring closing metathesis (RCM) catalyst to provide high yields of cyclic olefins (such as cyclopentene or cyclooctene). The high yield also provides high purity of the cyclic olefins. It has been discovered that high yields of cyclic olefins may be obtained without the use of added diluent (e.g., solvent) for the depolymerization, which improves the cost and throughput of an industrial scale depolymerization process. It has been further discovered that high yields of cyclic olefins may be obtained when treating vulcanized rubber (such as tires), for example with little or no pretreatment of the vulcanized rubber. Therefore, recycled cyclic olefins can be obtained in high yield (and high purity) for repurposing as starting monomers for polymerizations. The high purity of the recycled cyclic olefins can provide high purity recycled polymers (and vulcanized products thereof). [0178] RE-POLYMERIZATION OF RECYCLED MONOMERS Highly active Ru-based catalysts for the ROMP of cyclopentene typically cannot produce the polymers, polypentenamers, with high molecular weights (>300 kDa) because of the presence of non- cyclic olefins that act as chain-transfer agents even at <1 mol%. It limits the application of Ru- based catalysts for the production of high Mw polypentenamers, suitable for the tire industry. [0179] Commercial cyclopentene contains significant amounts of straight olefins that limits the number of available ROMP catalysts suitable for the production high molecular weight polypentenamers. The purification of cyclopentene from linear olefins by fractional distillation results in the significant loss of cyclopentene. Side products of manufacturing cyclopentene by selective hydrogenation of cyclopentadiene, 1,3-pentadienes (cis/trans), have a boiling points (42°C) close to that in cyclopentene (44°C). It makes the separation of cyclopentene from these disadvantageous contaminations challenging even at the industrial scale. [0180] The purity of reclaimed cyclopentene is sufficient for re-polymerizing into high Mw polypentenamers. In terms of circularity it opens the opportunity to use the scrap polypentenamer-based tires for the production of renewable cyclopentene and subsequent re- polymerizing into high Mw polypentenamers using highly active Ru-cats. [0181] In examples that follow, recycled cyclopentene, produced by depolymerization of polypentenamers (as discussed above), were used for the synthesis of high Mw polypentenamers (> 400 kDa) using Grubbs catalyst or a Ziegler-Natta catalyst. Moreover, the polymerization of the recycled olefin can be performed with any of the catalysts discussed herein. The higher quality of the recycled cyclopentene vs. commercial monomer enables the synthesis of high Mw polymers, suitable for the tire industry. [0182] Example 16. ROMP for Recycled Cyclopentene Using Ru-catalyst. The solution of Grubbs catalyst (dichloro[1,3-bis(2,6-isopropylphenyl)-2- imidazolidinylidene](benzylidene)(tricyclohexylphosphine)rut henium(II), 7 mg, 0.0073 mmol) in toluene was added to neat recycled cyclopentene (50 g, 0.735 mol) at -35°C. The reaction mixture was allowed to warm up to 0°C over 30 minutes before adding 300 mL of dichloromethane containing ethyl vinyl ether (0.5 mL). The resulting mixture was stirred for 12 hours at ambient conditions until all polymer product was dissolved. The product was precipitated with methanol containing 2,6-di-tert-butyl-4-methylphenol (0.5 g) and dried in vacuo at 55°C to give polypentenamer in the yield of up to 94 % (Table 11). [0183] Example 17. ROMP for Commercial Cyclopentene Using Ru-catalyst. The solution of Grubbs catalyst (dichloro[1,3-bis(2,6-isopropylphenyl)-2- imidazolidinylidene](benzylidene)(tricyclohexylphosphine)rut henium(II), 7 mg, 0.0073 mmol) in toluene was added to neat commercial cyclopentene (50 g, 0.735 mol) at -35°C. The reaction mixture was allowed to warm up to 0°C over 30 minutes before adding 300 mL of dichloromethane containing ethyl vinyl ether (0.5 mL). The resulting mixture was stirred for 12 hours at ambient conditions until all polymer product was dissolved. The product was precipitated with methanol containing 2,6-di-tert-butyl-4-methylphenol (0.5 g) and dried in vacuo at 55°C to give polypentenamer in the yield of 74% (Table 11). Table 11. Data for Polypentenamers Produced Using Recycled or Commercial Cyclopentene and Ru-catalyst. [0184] Example 18. ROMP for Recycled Cyclopentene Using Ziegler-Natta Catalyst. The catalyst was formed in situ by adding solid (p-MeC 6 H 4 O) 2 AlCl (102 mg, 0.368 mmol) to a solution of WCl6 (73 mg, 0.184 mmol) in toluene (5 mL). After stirring for one hour, the resulting mixture was added to the solution of cyclopentene (50.2 g, 738 mol) and triethylaluminum (42.1 mg, 0.369 mmol) in toluene (600 mL) at 0°C. After 180 minutes of intense mechanical stirring, a solution of 2,6-di-tert-butyl-4-methylphenol (1.00 g, 4.48 mmol) in 100 mL of ethanol/toluene mixture (1:4, v:v, respectively) was added. The obtained mixture was poured into ethanol (1 L). The precipitated polymer was then washed 3 times with ethanol (ca 100 mL each) and dried under vacuum at 50°C for 4 hours to give 23.0 g of the polymeric product. [0185] Example 19. ROMP for Commercial Cyclopentene Using Ziegler-Natta Catalyst. The catalyst was formed in situ by adding solid (p-MeC6H4O)2AlCl (202 mg, 0.731 mmol) to a solution of WCl 6 (145 mg, 0.366 mmol) in toluene (10 mL). After stirring for one hour, the resulting mixture was added to the solution of cyclopentene (99.7 g, 1.464 mol) and triethylaluminum (84 mg, 0.732 mmol) in toluene (500 mL) at 0°C. After 60 minutes of intense mechanical stirring, a solution of 2,6-di-tert-butyl-4-methylphenol (1.00 g, 4.48 mmol) in 100 mL of ethanol/toluene mixture (1:4, v:v, respectively) was added. The obtained mixture was poured into ethanol (2 L). The precipitated polymer was then washed 3 times with ethanol (250 mL each) and dried under vacuum at 50°C for 4 hours to give 43.0 g of the polymeric product. [0186] Table 12. Data for Polypentenamers Produced Using Recycled or Commercial Cyclopentene and Ziegler-Natta Catalyst. [0187] In at least one embodiment, the reactants (for example, metathesis catalyst; recycled olefin, optional diluent, etc.) are combined in a reaction vessel at a temperature of at a temperature of from less than 30°C to -60°C, preferably at a temperature of from -10°C to -50°C, such as from -20°C up to -40°C, or less than -10°C, -20°C or -30°C, so that the internal temperature of the reactor is maintained in a desired range, e.g., within 1°C, -15°C, -25°C, -35°C and/or at a pressure of about 1 atmosphere, and/or for a residence time of 0.5 seconds to 48 hours (such as 0.25 seconds to 5 hours, such as 30 minutes to 2 hours). [0188] In at least one embodiment of polymerization of a recycled olefin using ROMP reaction, the catalyst is present at from 0.001 nanomoles of transition metal per mole of unsaturated polymer to 1 millimole of transition metal per mole of unsaturated polymer, based upon the moles of unsaturated polymer feed into the reactor. Alternately, the catalyst is present at from 0.01 nanomoles of transition metal per mole of unsaturated polymer to 0.1 millimole of transition metal per mole of unsaturated polymer, alternately from 0.1 nanomoles of transition metal unsaturated polymer to 0.075 millimole of transition metal per mole of unsaturated polymer, based upon the moles of unsaturated polymer feed into the reactor. [0189] Processes of the present disclosure can be batch, semi-batch or continuous. As used herein, the term continuous means a system that operates without interruption or cessation. For example, a continuous process to produce polymers from recycled cyclic olefins would be one where the reactants are continually introduced into one or more reactors and polymer product is continually withdrawn. [0190] The processes for polymerization of recycled olefins may be conducted in any suitable reaction vessel, such as glass lined, stainless steel, or similar type reaction equipment. Useful reaction vessels include reactors (including continuous stirred tank reactors, batch reactors, reactive extruder, pipe, or pump, continuous flow fixed bed reactors, slurry reactors, fluidized bed reactors, and catalytic distillation reactors). The reaction zone may be fitted with one or more internal and/or external heat exchanger(s) in order to control undue temperature fluctuations, or to prevent “runaway” reaction temperatures. [0191] The quantity of catalyst that is employed in a polymerization of recycled olefins is any quantity that provides for an operable metathesis reaction. The ratio of moles of monomer units of a polymer (of the polymer starting material) to moles of catalyst can be typically greater than about 10:1, such as greater than about 100:1, such as greater than about 1000:1, such as greater than about 10,000:1, such as greater than about 25,000:1, such as greater than about 50,000:1, such as greater than about 100,000:1. Alternately, the molar ratio of monomer units of a polymer to catalyst is less than about 10,000,000:1, such as less than about 1,000,000:1, such as less than about 500,000:1. [0192] The contacting time of the reagents and catalyst in a batch reactor can be any duration, provided that the polymer products are obtained. Generally, the contacting time in a reactor is greater than about 5 minutes, such as greater than about 10 minutes. Generally, the contacting time in a reactor is less than about 25 hours, such as less than about 15 hours, such as less than about 10 hours. [0193] The phrases, unless otherwise specified, "consists essentially of" and "consisting essentially of" do not exclude the presence of other steps, elements, or materials, whether or not, specifically mentioned in this specification, so long as such steps, elements, or materials, do not affect the basic and novel characteristics of the present disclosure, additionally, they do not exclude impurities and variances normally associated with the elements and materials used. [0194] For the sake of brevity, only certain ranges are explicitly disclosed herein. However, ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited. Additionally, within a range includes every point or individual value between its end points even though not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited. [0195] All documents described herein are incorporated by reference herein, including any priority documents and or testing procedures to the extent they are not inconsistent with this text. As is apparent from the foregoing general description and the specific embodiments, while forms of the present disclosure have been illustrated and described, various modifications can be made without departing from the spirit and scope of the present disclosure. Accordingly, it is not intended that the present disclosure be limited thereby. Likewise, the term “comprising” is considered synonymous with the term “including” for purposes of United States law. Likewise whenever a composition, an element or a group of elements is preceded with the transitional phrase “comprising,” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of,” “consisting of,” “selected from the group of consisting of,” or “is” preceding the recitation of the composition, element, or elements and vice versa. [0196] While the present disclosure has been described with respect to a number of embodiments and examples, those skilled in the art, having benefit of this disclosure, will appreciate that other embodiments can be devised which do not depart from the scope and spirit of the present disclosure.