Title of Invention

METHOD FOR PRODUCING AMINO ALCOHOL COMPOUND Technical Field

[0001]

The present invention is intended to provide a method for producing an amino alcohol compound. Background Art

[0002]

An amino · alcohol compounds such as 2-amino-3-buten-l-ol or the like represented by the formula (2) :

[0003]

[Chemical formula 1]

(wherein R ¹ , R ² , and R ³ each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a hydrogen atom) (hereinafter, may be sometimes referred to as amino alcohol compound (2)) is an important compound as a monomer for functional polymers and as ^c a raw material for the production of pharmaceuticals, agrochemicals , and the like. [0004]

As a method for producing an amino alcohol compound (2) , for example, Non-Patent Document 1 describes a method for producing 2-amino-3-buten-l-ol through ammonolysis of

1 , 2-epoxybutene by mixing it with aqueous ammonia.

Citation List

Non-Patent Literatures

[0005]

Non-Patent Document 1: J. Amer. Chem. Soc, vol. 79, p

4792-4796, (1950)

Summary of the Invention

Technical Problem

[0006]

An object of the present invention is to provide a novel method that can produce an amino alcohol compound (2) ..

Solution to Problem

[0007]

As a result of diligent studies on a method for producing an amino alcohol compound (2) , the present inventor have reached the present invention.

[0008]

That is, the present ^' invention is as follows.

[1] A method for producing an amino alcohol compound represented by the formula (2) :

[0009]

[Chemical- formula 2]

wherein R ¹ , R ² , and R ³ each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a hydrogen atom, the method comprising a step of reacting a compound represented by the formula (1) :

[0010]

[Chemical formula 3]

wherein R ¹ , R ² , and R ³ each have the same meaning as defined above, with ammonia in the presence of a compound of Group 6 element in the periodic table.

[2] The method according to [1], wherein the step described above is a step of reacting a compound represented by the formula (1) with ammonia at a temperature selected from the range between 10°C and 50°C.

[3] The method according to [1] or [2], wherein the compound of Group 6 element in the periodic table is a heteropoly acid or salt thereof containing a Group 6 element in the periodic table.

[4] The method according to [1] or [2], wherein the compound of Group 6 element in the. periodic table is a heteropoly acid or salt thereof containing at least one element selected from the group consisting of tungsten and molybdenum.

[5] The method according to any one of [1] to [4] , wherein the compound represented by the formula (1) is

1, 2-epoxy-3-butene, and the amino alcohol compound represented by the formula (2) is 2-amino-3-buten-l-ol .

Advantageous Effects of Invention

[0011]

According to the present invention, it is possible to provide a novel method that can produce- an amino alcohol compound (2 ) .

Description of Embodiments

[0012]

A method for producing amino alcohol compound (2) according to the present invention is characterized in that the method includes a step of reacting a compound represented by the ^' formula (1) (hereinafter, may be sometimes referred to as compound (1) ) with ammonia in the presence of a compound of Group 6 element in the periodic table. [0013]

R R ² , and R ³ in the formulae (1) and (2) each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a hydrogen atom.

[0014]

Examples of the alkyl group include linear, branched, or cyclic alkyl groups having 1 to 20 carbon atoms, such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a n-pentyl group, a n-decyl group, a cyclopropyl group, a 2 , 2-dimethylcyclopropyl group, a cyclopentyl group, a cyclohexyl group, or a menthyl group. The alkyl group is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms.. Such an alkyl group may have, for example, at least one group selected from the group consisting of an alkoxy group having 1 to 6 carbon atoms, a halogen atom, an alkoxycarbonyl group having 2 to 8 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a carboxy group. Examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group and an ethoxy group; examples of the halogen.atom include a fluorine atom, a chlorine atom, and a bromine atom; examples of the alkoxycarbonyl group having 2 to 8 carbon atoms include a methoxycarbonyl group and an ethoxycarbonyl group; and examples of the aryl group having 6 to 10 carbon atoms include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. Examples of the alkyl group having a β substituent include a chloromethyl group, a fluoromethyl group, a trifluoromethyl group, a methoxymethyl group, an ethoxymethyl group, a 1-methoxyethyl group, a 2-methoxyethyl group, a methoxycarbonylmethyl group, and a benzyl group.

[0015]

Examples of the aryl group include aryl groups having 6 to 10 carbon atoms, such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. Such an aryl group may have at least one group selected from the group consisting of the

above-mentioned alkoxy group, halogen atom, alkoxycarbonyl group, aryl group, and carboxyl group.

[0016]

The compound (1) include the compound (1) wherein R ¹ , R ² , and R ³ are hydrogen atoms, the compound (1) wherein R ¹ is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, and R ² and R ³ are hydrogen atoms, the compound (1) wherein R ¹ is an alkyl group having 1 to 4 carbon atoms, either R ² or R ³ is a hydrogen atom, and another is an alkyl group having 1 to 4 carbon atoms, and the compound (.1 ) wherein R1 is a hydrogen ~atom, either R2 or R is a hydrogen atom, and another is an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms.

[0017]

Examples. of the compound (1) include 1, 2-epoxy-3-butene,

1, 2-epoxy-3-methyl-3-butene,

1, 2-epoxy-3, 4-dimethyl-3-butene, 1, 2-epoxy-4-methyl-3-butene, 1, 2-epoxy-3-phenyl-3-butene and

1 , 2-epoxy-4-phenyl-3-butene .

[0018]

The compound (1) can be produced by known methods, such as a method (see, for example, Japanese patent No. 2,854,059) including oxidizing a diene compound with oxygen in the presence of a silver-containing catalyst.

[0019]

The compound of Group 6 element in the periodic table is not limited as long as it is a compound that contains a Group 6 element in the periodic table, and examples thereof include chromic acid, molybdic acid, tungstic acid, and salts thereof, and preferably include a heteropoly acid or salt thereof containing a Group 6 element ^' in the periodic table. Examples of the Group 6 element in the periodic table include at least one kind selected from the group consisting of chromium, molybdenum,, and tungsten, and preferably include at least one kind selected from the group consisting of molybdenum and tungsten. That is, the compound of Group 6 element in the periodic table is preferably a heteropoly acid or salt thereof containing at least one element selected from the group consisting of tungsten and molybdenum.

[0020]

Examples of the heteropoly acid containing a Group 6 element in the periodic table include heteropolytungstic acid and heteropolymolybdic acid. Examples of the salt of heteropoly acid containing a Group 6 element in the periodic table include a salt of heteropolytungstic acid and a salt of heteropolymolybdic acid.

[0021]

Examples of the heteropolytungstic acid include phosphotungstic acid, silicotungstic acid, and borotungstic acid. Examples of the heteropolymolybdic acid include phosphomolybdic acid, silicomolybdic acid, and boromolybdic acid. Examples of the salt of heteropolytungstic acid include aluminum phosphotungstate , aluminum silicotungstate, and aluminum borotungstate. Examples of the salt of

heteropolymolybdic acid include aluminum phosphomolybdate, ammonium phosphomolybdate, aluminum silicomolybdate , ammonium silicomolybdate, aluminum boromolybdate, and ammonium boromolybdate .

[0022]

The heteropoly acid or salt thereof containing a Group 6 element in the periodic table is preferably at least one kind selected from the group consisting of phosphotungstic acid, phosphomolybdic acid, aluminum phosphotungstate, ammonium phosphotungstate, aluminum phosphomolybdate, or ammonium phosphomolybdate.

[0023]

One or two or more kinds of the compounds of Group 6 element in the periodic table may be used. Some of the compounds of Group 6 element in the periodic table may be present in the form of a hydrate among the compounds of Group 6 element in the periodic table, but the compound of Group 6 element in the periodic table may be a hydrate form or an anhydride form. The compound of Group 6 element in the periodic table may be commercially available or may be prepared according to a known method. For example, as the heteropoly acid or its ammonium salt containing a Group 6 element in the periodic table, a commercially available heteropoly acid or its ammonium salt containing a Group 6 element in the periodic table can.be used. In addition, as for the aluminum salt of heteropoly acid containing a Group 6 element in the periodic table, it is possible to use those that are prepared according to the method described in the literature (Catalysis Today, vol. 133-135, ^' (2008) , p 181-186) .

[0024]

The compound of Group 6 element. in the periodic table may be one that is supported on a carrier (hereinafter, may be sometimes referred to as supported catalyst) or may be one that is not supported on a carrier. Examples of the carrier include at least one kind selected from the group consisting of activated carbon, alumina, silica, zeolite, diatomaceous earth and zirconium oxide. The carrier preferably has a wide surface area in that the reaction activity is improved. The supported catalyst may be a commercially available one or may be one obtained by supporting at least one member selected from the group consisting of nitrate, sulfate, acetate, halide, and oxide of the Group 6 element in the periodic table, on the above-mentioned carrier by a co-precipitation method or a impregnation method, and then allowing it to be calcinated.

[0025]

Ammonia may be in any form of gaseous ammonia, liquefied ammonia, and an ammonia solution. The ammonia solution may be a solution in which ammonia is dissolved in a polar organic solvent such as methanol or the like, or may be an aqueous ammonia solution in which ammonia is .dissolved in water. The ammonia solution may be a commercially available one or may be one prepared by dissolving ammonia in a polar organic solvent or water. Ammonia is preferably gaseous ammonia, liquefied ammonia, or an aqueous ammonia solution, and more preferably an aqueous ammonia solution.

[0026]

The reaction of compound (1) with ammonia may be carried out in the presence of a solvent or may be carried out in the absence of a solvent. Examples of the solvent include ether solvents such as diethyl ether, methyl tert-butyl ether, and tetrahydrofuran; halogenated hydrocarbon solvents such as chloroform and chlorobenzene ; alcohol solvents such as methanol, ethanol, isopropanol, and tert-butanol; nitrile solvents such as acetonitrile and propionitrile; and water.

The solvent is preferably water.

[0027]

The reaction of compound (1) with ammonia may be carried out under a normal pressure condition or may be carried out under a pressurized condition. When the reaction is carried out under the pressurized condition, the pressurized condition is preferably about 0.3 MPa to about 2 MPa . The temperature at which the reaction is carried out is selected from the range of, for example, about -20°C to about 150°C, preferably selected from the range of about 0°C to about 100°C, and more preferably selected from the range between 10°C and 50°C . In the case where the temperature is higher than about 150°C, the occurrence- of by-products caused by the side reactions tends to increase, and in the case where the temperature is lower than about -20°C, the reactivity of the reaction tends to decrease.

[0028]

The reaction of compound (1) with ammonia can be carried out by contacting and mixing, for example, the compound (1), ammonia, the compound of Group 6 element in the periodic table, and optionally the solvent, and the mixing order of these components is not limited. The reaction can be carried out, for example, by any one of the methods according to (a) to (e) below.

[0029]

(a) A method of mixing ammonia, the compound of Group 6 element in the periodic table, and optionally the solvent and adding the compound (1) to the resulting mixture at a predetermined temperature;

(b) a method of mixing the compound (1), ammonia, the compound of Group 6 element in the periodic table, and optionally the solvent and adjusting the resulting mixture to a- predetermined temperature;

(c) a -method of mixing the compound (1) , ammonia, and optionally the solvent and adding the compound of Group 6 element in the periodic table to the resulting mixture at a predetermined temperature;

(d) a _^ method of mixing the compound (1) , the compound of Group 6 element in the periodic table, and optionally the solvent and adding ammonia to the resulting mixture at a predetermined temperature; and

(e) a method of mixing ammonia and the solvent and adding the compound ( 1 ) , .the compound of Group 6 element in the periodic table, and optionally the solvent to the resulting mixture at a. predetermined temperature.

[0030]

From the viewpoint of suppressing a further reaction of the resulting amino alcohol compound (2) with the compound (1) , the reaction is carried out preferably by the method described in (a) or (e), and more preferably by the method described in (a) . In addition, when the reaction is carried out under the pressurized condition, for example, a method of injecting ammonia under pressure can be employed for the addition of ammonia in the method of (d)..

[0031]

The amount of the compound of Group 6 element in the periodic table to be used is preferably 0.001 mol or more based on 1 mol of the compound (1) . The upper limit of the amount of the compound of Group 6 element in the periodic table to be used is not limited, but considering the economic aspects, the amount to be used is practically 0.5 mol or less based on 1 mol of the compound (1) .

[0032]

The amount of ammonia to be used is, for example, 1 mol or more based on 1 mol of the compound (1) . From the viewpoint of suppressing a further reaction of the resulting amino alcohol compound (2) with the compound (1) , ammonia is preferably used, for example, in excess based on the compound (1) . When the reaction is carried out by the method according to any one of (b) to (d) described above., the amount of ammonia to be used is 10 mol or more based on 1 mol of the compound (1) . When the reaction is carried out by the method according to any one of (b) to (d) described above, the upper limit of ammonia used is not limited, but considering production efficiency or the like, it is practically 100 mol or less. When the reaction is carried out by the method according to (a) or (e) described above, the amount of ammonia to be used is preferably 5 mol or more, and more preferably 10 mol or more based on 1 mol of the compound (1) . When the reaction is carried out by the method according to (a) or (e) described above, the upper limit of ammonia used is not limited, but considering production efficiency or the like, it is practically 100 mol or less. [0033]

When the reaction is carried out in the presence of the solvent, the amount of the solvent to be used is not limited, but considering volumetric efficiency or the like, it is practically 100 parts by weight or less based on 1 part by weight of the compound (1) .

[0034]

The progress of the reaction can be confirmed by an analysis means, such as gas chromatography, high performance liquid chromatography, thin layer chromatography, nuclear magnetic resonance spectrum analysis, infrared absorption spectrum analysis, or the like.

[0035]

After completion of the reaction, the amino alcohol compound (2) can be extracted by, for example, recovering ammonia through, for example, optional evaporation of ammonia used in excess, then filtering and processing the reaction mixture, and subjecting the obtained filtrate to concentration processing, separation processing, crystallization processing, and the like. The compound of Group 6 element in the periodic table used in the reaction may be recovered as a solid by, for example, the above filtration processing, or may be recovered as a solution by, for example, the above separation processing. The amino' alcohol compound (2) can also be purified by crystallizing it as a salt with oxalic acid, purifying the oxalate, and then decomposing the oxalate (for example, see J. Amer. Chem. Soc, vol. 79, p 4792-4796, (1950)) . The amino alcohol compound (2) may be further purified by the technique, such as distillation, column chromatography, and the like. The compound (2) can also be purified by, for example, rectification using a rectifying column.

[0036]

Examples of the thus obtained amino alcohol compound (2) include 3-butene-2-amino-l-ol ,

3-methyl-3-butene-2 -amino- l-ol ,

3, 4-dimethyl-3-butene-2-amino-l-ol ,

4 -methyl-3-butene-2 -amino-l-ol,

3-phenyl-3-butene-2-amino-l-ol , and

4-phenyl-3-butene-2-amino-l-ol .

[0037]

After completion ..of the reaction, the compound of Group

6 element in the periodic table that has been recovered as a solid by, for example, the filtration processing can be re-used in the reaction as it is or after optional purification. In addition, after completion of the reaction, the compound of Group 6 element in the periodic table that has been recovered as a solution by, for example, the separation processing is concentrated as needed, and can be re-used in the reaction as it. is or after optional purification. Examples

[0038] Hereinafter, the present invention will be described in detail by way of Examples.

[0039]

Example 1

<Production of 2-amino-3-buten-l-ol (amino alcohol compound (2))>

Into a 100 mL-stainless steel reaction tube equipped with a magnetic rotor were added 200 mg of 3-butene-l , 2-epoxide , 10 g of 28% aqueous ammonia, and 10 mg of aluminum phosphotungstate , and the resulting mixture was stirred at an inner temperature of 40°C for 6 hours so that 3-butene-l , 2-epoxide and ammonia were reacted. The pressure inside the reaction tube during the reaction was 0.3 MPa to 0.4 MPa . The resulting reaction mixture was cooled to room temperature, and ammonia was removed from. the reaction mixture by evaporation, so that the pressure inside the reaction tube was maintained at normal pressure. Then, the total content of 2-amino-3-buten-l-ol and its regioisomer l-amino-3-buten-2-ol contained in the obtained reaction mixture and the content of 3-butene-l, 2-epoxide were determined by GC analysis (internal standard method) . In.- addition, the ratio of 2-amino-3-buten-l-ol and l-amino-3-buten-2-ol was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield of 2-amino-3-buten-l-ol : 58%

Yield of l-amino-3-buten-2-ol : 40%

Recovery rate of raw material 3-butene-l , 2-epoxide : 0% [0040]

Example 2

<Production of 2-amino-3-buten-l-ol (amino alcohol compound (2))>

Into a 100 mL-stainless steel reaction tube equipped with a magnetic rotor were added 200 mg of 3-butene-l, 2-epoxide, 10 g of 28% aqueous ammonia, and 10 mg of phosphotungstic acid, and the resulting mixture was stirred at an inner temperature of 40°C for 7 hours so that 3-butene-l , 2-epoxide and ammonia were reacted. The pressure inside the reaction tube during the reaction was 0.3 MPa to 0.4 MPa . The resulting reaction mixture was cooled to room temperature, and ammonia was removed from the reaction mixture by evaporation, so that the pressure inside the reaction tube was maintained at normal pressure. Then, the total content of 2-amino-3-buten-l-ol and its regioisomer l-amino-3-buten-2-ol contained in the obtained _. reaction mixture and the content of 3-butene-l, 2-epoxide were determined by GC analysis (internal standard method). In addition, the ratio of 2-amino-3-buten-l-ol and l-amino-3-buten-2-ol was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield _s of 2-amino—3-buten-l-ol : 57%

Yield of l-amino-3-buten-2-ol: 41%

Recovery rate of raw mate ^' rial 3-butene-l , 2-epoxide : 0% [0041]

Example 3 <Production of 2-amino-3-buten-l-ol (amino alcohol compound (2) )>

Into a 100 mL-stainless steel reaction tube equipped with a magnetic rotor were added 200 mg of 3-butene-l, 2-epoxide, 10 g. of 28% aqueous ammonia, and 10 mg of ammonium phosphomolybdate , and the resulting mixture was stirred at an inner temperature of 40°C for 7 hours so that 3-butene-l, 2-epoxide and ammonia were reacted. The pressure inside the reaction tube during the reaction was 0.3 MPa to 0.4 MPa . The resulting reaction mixture was cooled to room temperature, and ammonia was removed from the reaction mixture by evaporation, so that the pressure inside the reaction tube was maintained at normal pressure. Then, the total content of 2-amino-3-buten-l-ol and its regioisomer l-amino-3-buten-2-ol contained in the obtained reaction mixture and the content of 3-butene-l, 2-epoxide were determined by GC analysis (internal standard method) . In addition, the ratio- of 2-amino-3-buten-l-ol and l-amino-3-buten-2-ol was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield of 2-amino-3-buten-l-ol : 57%

Yield of l-amino-3-buten-2-ol: 41%

Recovery rate of raw material 3-butene-l, 2-epoxide : 0% [0042]

Example. 4

Production of 2-amino-3-buten-l-ol (amino alcohol compound (2) )> Into a 300 mL-Schlenk flask equipped with a magnetic rotor were added 100 g of 28% aqueous ammonia and 100 mg of aluminum phosphotungstate, and 10 g of 3-butene-l , 2-epoxide was added dropwise to the resulting mixture under stirring at an inner temperature of 0°C over a period of one hour. Then, the obtained mixture was stirred at an inner temperature of 25°C for 4 hours so that 3-buten.e-l, 2-epoxide and ammonia were reacted. The reaction, the aqueous ammonia and the unreacted

3-butene-l, 2-epoxide were removed from the reaction mixture by evaporation, thereby to obtain 12.0 g of a colorless oil. The total content of 2-amino-3-buten-l-ol and

l-amino-3-buten-2-ol contained in the obtained colorless oil and the content of 3-butene-l , 2-epoxide were determined by GC analysis (internal standard method) . In addition, the ratio of 2-amino-3-buten-l-ol and l-amino-3-buten-2-ol was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield of 2-amino-3-buten-l-ol: 47%

Yield of l-amino-3-buten-2-ol: 48%

Recovery rate of raw material 3-butene-l , 2-epoxide : 0%

[0043]

Reference Example 1

<Purification of 2-amino-3-buten-l-ol (amino alcohol compound (2))>

Into a 100 mL-flask were added 5.0 g of the colorless oil obtained in Example 4 and 10 g of ethanol, and the two components were dissolved. To the resulting solution, a solution prepared by dissolving 5.0 g of oxalic acid in 20 g of ethanol was added. Then, ethanol was evaporated from the resulting solution on a rotary evaporator at a bath temperature of 30°C until crystals were slightly precipitated. The concentrated solution was cooled with ice water for one hour and the precipitated crystals (first crystal) were filtered, and dried to obtain- 4..2 g of the crystals (first crystal). After the crystals were subjected to salt decomposition by mixing with an aqueous sodium hydroxide solution, the ratio of 2-amino-3-buten-l-ol and

l-amino-3-buten-2-ol that had been extracted with chloroform was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield of 2-amino-3-buten-l-ol : 22%

Yield of l-amino-3-buten-2-ol : 78%

[0044]

The filtrate obtained in the filtration of the first crystal was concentrated, and the resulting precipitated crystals (second crystal) were filtered and dried to obtain 1.8 g of the crystals (second crystal) . The filtrate obtained in the filtration of the second crystal was made alkaline with a 10% aqueous sodium hydroxide solution, and extracted twice with 10 mL of diethyl ether. The obtained diethyl ether layer was concentrated to give 1.97 g of 2-amino-3-buten-l-ol as a colorless oil. The ratio of 2-amino-3-buten-l-ol and l-amino-3-buten-2-ol contained in the colorless oil was determined as a diacylated derivative using acetyl chloride and pyridine.

Yield of 2-amino-3-buten-l-ol: 90%

Yield of l-amino-3-buten-2-ol : 10%

[0045]

Example 5

<Production of 2-amino-3-buten-l-ol (amino alcohol compound (2))>

Into a 100 mL-stainless steel reaction tube equipped with a magnetic rotor were added 200 mg of 3-butene-l, 2-epoxide, 10 g of 28% aqueous ammonia, and 10 mg of silicotungstic acid, and the resulting mixture was stirred at an inner temperature of 40°C for 6 hours so that 3-butene-l, 2-epoxide and ammonia were reacted. The pressure inside the reaction tube during the reaction was 0.3 MPa to 0.4 MPa . The resulting reaction mixture was cooled to room temperature, and ammonia was removed from the reaction mixture by evaporation, so that the pressure inside the reaction tube was maintained at normal pressure. Then, the total content of 2-amino-3-buten-l-ol and its regioisomer l-amino-3-buten-2-ol contained in the obtained reaction mixture and the content of 3-butene-l, 2-epoxide were determined by GC analysis _. (internal standard method) . In addition, the ratio of 2-amino-3-buten-l-ol and l-amino-3-buten-2-ol was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield of 2-amino-3-buten-l-ol: 43% Yield of l-amino-3-buten-2-ol : 53%

Recovery rate of raw material 3-butene-l, 2-epoxide : 0% [0046]

Example 6

<Production of 2-amino-3-buten-l-ol (amino alcohol compound (2))>

Into a 100 mL-stainless steel reaction tube equipped with a magnetic rotor were added 200 mg of 3-butene-l, 2-epoxide, 10 g of 28% aqueous ammonia, and 10 mg of molybdenum oxide supported on silica gel, and the resulting mixture was stirred at an inner temperature of 40°C for 6 hours so that 3-butene-l, 2-epoxide and ammonia were reacted. The pressure inside the reaction tube during the reaction was 0.3 MPa to 0.4 MPa. The resulting reaction mixture was cooled to room temperature, and ammonia was removed from the reaction mixture by evaporation, so that the pressure inside the reaction tube was maintained at normal pressure.. Then, the total content of 2-amino-3-buten-l-ol and its regioisomer l-amino-3-buten-2-ol contained in the obtained reaction mixture and the content of 3-butene-l , 2-epoxide were determined by GC analysis (internal standard method) . In addition, the ratio of 2-amino-3-buten-l-ol and

l-amino-3-buten-2-ol was determined as a diacylated derivative using acetyl chloride and pyridine, and the following yields were calculated.

Yield of 2-amino-3-buten-l-ol : 50%

Yield of l-amino-3-buten-2-ol: 48% Recovery rate of raw material 3-butene-l, 2-epoxide : 0%

Industrial Applicability

[0047]

The amino alcohol compound (2) is an important compound as a monomer for functional polymers and as ^' a raw material for the production of pharmaceuticals , agrochemicals , and the like. The present invention is industrially applicable as a method for producing the amino alcohol compound (2).