CN111500651A - Preparation method of phenylethylamine - Google Patents
Preparation method of phenylethylamine Download PDFInfo
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Abstract
The invention discloses a preparation method of phenethylamine, belonging to the technical field of chemical industry. The preparation method comprises the following steps: reacting a reactant solution for generating phenylethylamine through a reaction column to obtain a product mixed solution; the reaction column is filled with a biocatalyst, a silica gel ball and pyridoxal phosphate; evaporating the product mixed solution; adsorbing the product mixed solution after the evaporation treatment by an adsorption column; the adsorption column is filled with weak acid cation exchange resin; performing reverse analysis on the adsorption column subjected to adsorption treatment by using methanol to obtain an analysis solution; and (4) sequentially evaporating and distilling the analytic solution under reduced pressure to obtain phenylethylamine. According to the invention, the reactant solution is reacted through the reaction column filled with the biocatalyst, the silica gel ball and the pyridoxal phosphate, and the phenylethylamine is adsorbed by the adsorption column filled with the weak-acid cation exchange resin, so that the conversion rate and the yield of the phenylethylamine can be greatly improved.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a preparation method of phenethylamine.
Background
Phenethylamines can be prepared by reacting acetophenone and isopropylamine. Currently, phenylethylamine preparation methods generally include the following steps: the reactants are firstly put into a kettle type reactor for reaction, and then the reaction liquid is treated by adding acid, extraction, dissociation, evaporation, reduced pressure distillation and the like to separate the phenethylamine.
However, the above preparation method of phenylethylamine has a poor separation effect on phenylethylamine, and has the problems of low one-time conversion rate, complicated operation, more waste salts and low phenylethylamine yield.
Disclosure of Invention
The present invention aims at providing a preparation method of phenethylamine to solve the problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a preparation method of phenylethylamine comprises the following steps:
reacting a reactant solution for generating phenylethylamine through a reaction column to obtain a product mixed solution; the reaction column is filled with a biocatalyst, a silica gel ball and pyridoxal phosphate;
evaporating the product mixed solution;
the product mixed solution after the evaporation treatment is subjected to adsorption treatment through at least one group of adsorption columns; the adsorption column is filled with weak acid cation exchange resin;
performing reverse analysis on the adsorption column subjected to adsorption treatment by using methanol to obtain an analysis solution;
and (4) sequentially evaporating and distilling the analytic solution under reduced pressure to obtain phenylethylamine.
Preferably, the reactant solution comprises acetophenone, isopropylamine and water; the volume ratio of the acetophenone to the isopropylamine to the water is 20: 3-5: 0.05-0.2.
Preferably, in the step of reacting the reactant solution for generating phenylethylamine through the reaction column, the reaction temperature is 30-50 ℃.
Preferably, the mass ratio of the biocatalyst, the silica gel ball and the pyridoxal phosphate is (600-800) to (400-600) to 1.
Preferably, the mass-to-volume ratio of the pyridoxal phosphate to the reactant solution is 1: 8-12 in mg/m L.
Preferably, in the step of evaporating the product mixture, the temperature of the evaporation treatment is 60 to 80 ℃.
Preferably, the weakly acidic cation exchange resin is a polymer of 2-acrylic acid and divinylbenzene.
Preferably, the mass ratio of the weak acid cation exchange resin to the product mixed solution after evaporation treatment is 5: 6-10.
Preferably, in the step of sequentially evaporating and distilling the analysis solution under reduced pressure, the evaporation temperature is 65 to 85 ℃.
Preferably, in the step of sequentially evaporating and distilling the analysis solution under reduced pressure, the temperature of the reduced pressure distillation is 110 to 120 ℃.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
according to the preparation method of phenylethylamine provided by the embodiment of the invention, the reactant solution is reacted through the reaction column filled with the biocatalyst, the silica gel ball and the pyridoxal phosphate, and the phenylethylamine is adsorbed by the adsorption column filled with the weak-acid cation exchange resin, so that the conversion rate and the yield of the phenylethylamine can be greatly improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The embodiment of the invention provides a preparation method of phenethylamine, which comprises the following steps:
(1) reacting a reactant solution for generating phenylethylamine through a reaction column to obtain a product mixed solution, wherein the reaction temperature is 30-50 ℃, the reaction column is filled with a biocatalyst, a silica gel ball and pyridoxal phosphate, the mass ratio of the biocatalyst to the silica gel ball to the pyridoxal phosphate is (600-800) to (400-600) to 1, the mass-to-volume ratio of the pyridoxal phosphate to the reactant solution is 1 to (8-12) in mg/m L, the reactant solution comprises acetophenone, isopropylamine and water, the volume ratio of the acetophenone, the isopropylamine and the water is 20 to (3-5) to (0.05-0.2), and in addition, the biocatalyst can be selected from the existing immobilized enzymes.
(2) Evaporating the product mixed solution; the temperature of the evaporation treatment is 60-80 ℃.
(3) The product mixed solution after the evaporation treatment is subjected to adsorption treatment through at least one group of adsorption columns; the adsorption column is filled with weak acid cation exchange resin; the weak-acid cation exchange resin is a polymer of 2-acrylic acid and divinylbenzene; the mass ratio of the weak acid cation exchange resin to the product mixed solution after evaporation treatment is 5: 6-10.
(4) Performing reverse analysis on the adsorption column subjected to adsorption treatment by using methanol to obtain an analysis solution; (5) sequentially evaporating and distilling the resolving solution under reduced pressure to obtain phenylethylamine; in the step of sequentially evaporating and distilling the analysis solution under reduced pressure, the evaporating temperature is 65-85 ℃, and the distilling temperature under reduced pressure is 110-120 ℃.
The following examples are given for specific embodiments of the above method in practice.
Example 1
The embodiment provides a preparation method of phenethylamine, which comprises the following steps:
(1) mixing 80m of L acetophenone, 12m of L isopropylamine and 0.2m of L water to obtain a reactant solution, passing the reactant solution through a reaction column filled with 6.915g of biocatalyst, 4.61g of silica gel spheres and 11.525mg of pyridoxal phosphate, and circulating by using a peristaltic pump to react the reactant solution at 20 ℃ for 24 hours to obtain a product mixed solution, wherein the biocatalyst is the existing transaminase.
(2) Evaporating the product mixed solution by using a rotary evaporator under the conditions of 60 ℃ and-0.090 MPa to remove isopropylamine and acetone generated by the reaction, thus obtaining the product mixed solution after evaporation treatment.
(3) 60g of the product mixed solution after evaporation treatment is parallelly passed through two groups of adsorption columns filled with 50g of weakly acidic cation exchange resin for adsorption treatment, and the residual liquid can be recycled; among them, the weakly acidic cation exchange resin is a commercially available polymer of 2-acrylic acid and divinylbenzene (Dowex MAC-3 ion exchange resin, CAS No. 9052-45-3).
(4) The adsorption column after the adsorption treatment was subjected to reverse direction analysis 2 times with 30m L of methanol to obtain an analysis solution.
(5) Evaporating the analysis solution by a rotary evaporator at 65 ℃ and under the pressure of-0.090 MPa to remove methanol and water until no liquid flows down; then, the receiving bottle is replaced, and the temperature is raised to 110 ℃ for reduced pressure distillation treatment, so that the phenethylamine can be obtained.
Example 2
The embodiment provides a preparation method of phenethylamine, which comprises the following steps:
(1) mixing 80m L acetophenone, 20m L isopropylamine and 0.8m L water to obtain a reactant solution, passing the reactant solution through a reaction column filled with 6.72g of biocatalyst, 5.04g of silica gel spheres and 8.4mg of pyridoxal phosphate, and circulating by using a peristaltic pump to react the reactant solution at 50 ℃ for 12 hours to obtain a product mixed solution, wherein the biocatalyst is the existing transaminase.
(2) Evaporating the product mixed solution by a rotary evaporator at 80 ℃ and under the pressure of-0.090 MPa to remove isopropylamine and acetone generated by the reaction, thus obtaining the product mixed solution after evaporation treatment.
(3) 80g of the product mixed solution after evaporation treatment is parallelly passed through two groups of adsorption columns filled with 40g of weak acid cation exchange resin for adsorption treatment, and the residual liquid can be recycled; among them, the weakly acidic cation exchange resin is a commercially available polymer of 2-acrylic acid and divinylbenzene (Dowex MAC-3 ion exchange resin, CAS No. 9052-45-3).
(4) The adsorption column after the adsorption treatment was subjected to reverse direction analysis 2 times with 30m L of methanol to obtain an analysis solution.
(5) Evaporating the analysis solution by a rotary evaporator at 85 ℃ and under the pressure of-0.090 MPa to remove methanol and water until no liquid flows down; then, the receiving bottle is replaced, and the temperature is raised to 120 ℃ for reduced pressure distillation treatment, so that the phenethylamine can be obtained.
Example 3
The embodiment provides a preparation method of phenethylamine, which comprises the following steps:
(1) mixing 80m L acetophenone, 18m L isopropylamine and 0.5m L water to obtain a reactant solution, passing the reactant solution through a reaction column filled with 7.5g of a biocatalyst, 5g of silica gel spheres and 10mg of pyridoxal phosphate, and circulating by using a peristaltic pump to allow the reactant solution to react for 24 hours at 40 ℃ to obtain a product mixed solution, wherein the biocatalyst is the existing transaminase.
(2) Evaporating the product mixed solution by using a rotary evaporator under the conditions of 60 ℃ and-0.090 MPa to remove isopropylamine and acetone generated by the reaction to obtain 82.6281g of the product mixed solution after evaporation treatment, wherein the mass ratio of acetophenone, phenethylamine and water in the product mixed solution after evaporation treatment is 67.0991: 15.0290: 0.5000.
(3) 82.6281g of the product mixed solution after evaporation treatment is parallelly passed through two groups of adsorption columns filled with 50g of weak acid cation exchange resin for adsorption treatment, 14.1273g of phenethylamine is adsorbed together, and the rest 68.4008g of liquid can be recycled, wherein the water content is 0.585%; among them, the weakly acidic cation exchange resin is a commercially available polymer of 2-acrylic acid and divinylbenzene (Dowex MAC-3 ion exchange resin, CAS No. 9052-45-3).
(4) The adsorption column after the adsorption treatment was subjected to reverse direction analysis 2 times with 30m L of methanol to obtain an analysis solution.
(5) Evaporating the analysis solution by a rotary evaporator at 65 ℃ and under the pressure of-0.090 MPa to remove methanol and water until no liquid flows down; then, the receiving bottle was replaced, and the temperature was raised to 120 ℃ to conduct distillation under reduced pressure, thereby obtaining 13.2390g of phenethylamine.
Example 4
The embodiment provides a preparation method of phenethylamine, which comprises the following steps:
(1) mixing 800kg of acetophenone, 124.2kg of isopropylamine and 5kg of water to obtain a reactant solution, and passing the reactant solution through a reaction column filled with 75.75kg of biocatalyst, 50kg of silica gel beads and 102.4g of pyridoxal phosphate; then, the reactant solution is circulated by a peristaltic pump to react for 24 hours at the temperature of 40 ℃ to obtain a product mixed solution. Wherein the biocatalyst is an existing transaminase.
(2) And (3) evaporating the product mixed solution by using a rotary evaporator under the conditions of 60 ℃ and-0.090 MPa to remove isopropylamine and acetone generated by the reaction to obtain 800kg of the product mixed solution after evaporation treatment, wherein the mass ratio of the acetophenone, the phenethylamine and the water in the product mixed solution after evaporation treatment is 638.4: 161.6: 5.
(3) Adsorbing 800kg of the product mixed solution after evaporation treatment by two groups of adsorption columns filled with 490kg of weak acid cation exchange resin in parallel to adsorb 153.52kg of phenethylamine, wherein the water content is 0.767 percent, and the rest 651.48kg of liquid can be recycled; among them, the weakly acidic cation exchange resin is a commercially available polymer of 2-acrylic acid and divinylbenzene (Dowex MAC-3 ion exchange resin, CAS No. 9052-45-3).
(4) The adsorption column after the adsorption treatment was subjected to reverse direction analysis 2 times with 188.43kg of methanol to obtain an analysis solution.
(5) Evaporating the analysis solution by a rotary evaporator at 65 ℃ and under the pressure of-0.090 MPa to remove methanol and water until no liquid flows down; then, the receiving bottle was replaced, and the temperature was raised to 120 ℃ to conduct distillation under reduced pressure, thereby obtaining 135.23kg of phenethylamine.
Comparative example 1
The comparative example provides a method of preparing phenethylamine, comprising the steps of:
(1) mixing 80m L acetophenone, 18m L isopropylamine and 0.5m L water to obtain a reactant solution, passing the reactant solution through a reaction column filled with 7.5g of a biocatalyst, 5g of silica gel spheres and 10mg of pyridoxal phosphate, and circulating by using a peristaltic pump to allow the reactant solution to react for 24 hours at 40 ℃ to obtain a product mixed solution, wherein the biocatalyst is the existing transaminase.
(2) Evaporating the product mixed solution by using a rotary evaporator under the conditions of 60 ℃ and-0.090 MPa to remove isopropylamine and acetone generated by the reaction to obtain 82.6280g of the product mixed solution after evaporation treatment, wherein the mass ratio of acetophenone, phenethylamine and water in the product mixed solution after evaporation treatment is 67.0991: 15.0290: 0.5000.
(3) 82.6280g of the product mixed liquid after evaporation treatment is parallelly passed through two groups of adsorption columns filled with 50g of strong-acid cation exchange resin for adsorption treatment, so that 12.335g of phenethylamine is adsorbed, and the rest 68.4005g of liquid can be recycled, wherein the water content is 0.586%; wherein the weakly acidic cation exchange resin is commercially available D001 macroporous strongly acidic styrene cation exchange resin with CAS number 53025-53-9.
(4) The adsorption column after the adsorption treatment was subjected to reverse direction analysis 2 times with 30m L aqueous hydrochloric acid solution to obtain an analysis solution.
(5) Adding 30m of L NaOH aqueous solution into the analytic solution to neutralize hydrochloric acid and dissociate phenylethylamine, distilling the mixture by using a rotary evaporator at 65 ℃ and under the condition of-0.090 MPa under reduced pressure until milky white liquid is obtained, starting to collect milky white liquid segments which are mainly the topiramate and the phenylethylamine, replacing a receiving bottle after the milky white liquid segments are completely flowed out and the distillate is transparent and homogeneous, heating to 110 ℃, and starting to collect the phenylethylamine until no liquid flows down to obtain 8.477g of the phenylethylamine.
Comparative example 2
The comparative example provides a method of preparing phenethylamine, comprising the steps of:
(1) firstly, 80m of L acetophenone, 17m of L isopropylamine and 0.5m of L water are mixed to obtain a reactant solution, the reactant solution is added into a three-neck flask, then, 7.5g of a biocatalyst and 10mg of pyridoxal phosphate are weighed and added into the three-neck flask, then, stirring is started, and the reactant solution reacts for 24 hours at the temperature of 40 ℃ to obtain a product mixed solution, wherein the biocatalyst is the existing transaminase.
(2) Evaporating the product mixed solution by using a rotary evaporator under the conditions of 60 ℃ and-0.090 MPa to remove isopropylamine and acetone generated by the reaction to obtain 82.6280g of the product mixed solution after evaporation treatment, wherein the mass ratio of acetophenone, phenethylamine and water in the product mixed solution after evaporation treatment is 73.2085: 9.4195: 0.5000.
(3) 82.6280g of the product mixed liquid after evaporation treatment is parallelly passed through two groups of adsorption columns filled with 50g of strong-acid cation exchange resin for adsorption treatment, so that 7.818g of phenethylamine is adsorbed, and the rest 74.81g of liquid can be recycled, wherein the water content is 0.8276%; wherein the weakly acidic cation exchange resin is commercially available D001 macroporous strongly acidic styrene cation exchange resin with CAS number 53025-53-9.
(4) The adsorption column after the adsorption treatment was subjected to reverse direction analysis 2 times with 30m L aqueous hydrochloric acid solution to obtain an analysis solution.
(5) Adding 30m of L NaOH aqueous solution into the analytic solution to neutralize hydrochloric acid and dissociate phenylethylamine, distilling the mixture by using a rotary evaporator at 65 ℃ and under the condition of-0.090 MPa under reduced pressure until milky white liquid is obtained, starting to collect milky white liquid segments which are mainly the topiramate and the phenylethylamine, replacing a receiving bottle after the milky white liquid segments are completely flowed out and the distillate is transparent and homogeneous, heating to 110 ℃, and starting to collect the phenylethylamine until no liquid flows down to obtain 5.2381g of the phenylethylamine.
The conversion of phenethylamine, the adsorption rate of phenethylamine (adsorption rate of the adsorption column to phenethylamine) and the yield of phenethylamine were calculated from the phenethylamines obtained in examples 3 to 4 and comparative examples 1 to 2, and the calculation results are shown in table 1 below.
TABLE 1
| Group of | Conversion rate/% | Adsorption rate/%) | Yield/% |
| Example 3 | 18.3 | 94 | 88.09 |
| Example 4 | 20.2 | 94 | 88.1 |
| Comparative example 1 | 18.3 | 82.1 | 68.7 |
| Comparative example 2 | 11.4 | 83 | 67 |
As can be seen from table 1 above, the conversion rate of phenethylamine can be significantly improved by using the reaction mode of the reaction column instead of the kettle-type reaction; the weak-acidic cation exchange resin is used for replacing the strong-acidic cation exchange resin to adsorb the phenylethylamine, so that the adsorption rate of the phenylethylamine can be obviously improved; the adsorption column adsorbing the phenylethylamine is analyzed by using methanol instead of a hydrochloric acid aqueous solution, so that the yield of the phenylethylamine can be obviously improved.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (10)
1. The preparation method of phenylethylamine is characterized by comprising the following steps of:
reacting a reactant solution for generating phenylethylamine through a reaction column to obtain a product mixed solution; the reaction column is filled with a biocatalyst, a silica gel ball and pyridoxal phosphate;
evaporating the product mixed solution;
the product mixed solution after the evaporation treatment is subjected to adsorption treatment through at least one group of adsorption columns; the adsorption column is filled with weak acid cation exchange resin;
performing reverse analysis on the adsorption column subjected to adsorption treatment by using methanol to obtain an analysis solution;
and (4) sequentially evaporating and distilling the analytic solution under reduced pressure to obtain phenylethylamine.
2. The method of claim 1, wherein the reactant solution comprises acetophenone, isopropylamine and water; the volume ratio of the acetophenone to the isopropylamine to the water is 20 (3-5) to (0.05-0.2).
3. The method for preparing phenylethylamine according to claim 1, wherein in the step of reacting the reactant solution for generating phenylethylamine through the reaction column, the reaction temperature is 30-50 ℃.
4. The method for preparing phenylethylamine according to claim 1, wherein the mass ratio of the biocatalyst to the silica gel beads to the pyridoxal phosphate is (600-800): (400-600): 1.
5. The method for producing phenethylamine according to claim 1 or 4, wherein the mass-to-volume ratio of pyridoxal phosphate to the reactant solution is 1 (8-12) in mg/m L.
6. The method for preparing phenethylamine according to claim 1, wherein in the step of evaporating the product mixture, the temperature of the evaporation treatment is 60 to 80 ℃.
7. The method of claim 1, wherein the weakly acidic cation exchange resin is a polymer of 2-acrylic acid and divinylbenzene.
8. A method for preparing phenethylamine according to claim 1 or 7, wherein the mass ratio of the weakly acidic cation exchange resin to the product mixture after evaporation is 5 (6-10).
9. The method for preparing phenethylamine according to claim 1, wherein in the step of sequentially evaporating and distilling the solution under reduced pressure, the temperature of evaporation is 65 to 85 ℃.
10. The method for preparing phenethylamine according to claim 1 or 9, wherein in the step of sequentially evaporating and distilling the desorption solution under reduced pressure, the temperature of the reduced pressure distillation is 110 to 120 ℃.
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| CN114181192A (en) * | 2021-11-21 | 2022-03-15 | 福建科宏生物工程股份有限公司 | Resin deamination method in R-lipoic acid synthesis process |
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