IP Library Granted Patent US 10,851,392
Granted Patent B2
US 10,851,392 · App. 14/405,593 · Granted Dec 1, 2020

Method for producing methacrylic acid ester

Inventors: Eiji Sato (Kanagawa, JP); Fujio Yu (Kanagawa, JP); Wataru Mizunashi (Kanagawa, JP); Eiji Nakajima (Kanagawa, JP)
Assignee: Mitsubishi Chemical Corporation
C12P7/62C12N1/20C12N9/1025C12Y203/01084
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Quick Facts
Patent No.
US 10,851,392
App. No.
14/405,593
Granted
Dec 1, 2020
Kind
B2
Abstract

Provided is a method for producing a methacrylic acid ester using a biocatalyst, said method comprising a step for treating methacrylyl-CoA with an alcohol or phenol in the presence of an alcohol acyltransferase to synthesize the methacrylic acid ester. According to this production method, a methacrylic acid ester can be efficiently produced while largely reducing energy, resource and environmental load, compared with the conventional chemical production processes.

Claims (14)

1. A method for producing methacrylic acid ester, the method comprising:

transforming isobutyryl-CoA or 3-hydroxyisobutyryl-CoA to form methacrylyl-CoA, and

contacting methacrylyl-CoA with an alcohol or a phenol in the presence of an alcohol acyltransferase, wherein the methacrylic acid ester accumulated has a concentration of at least 0.001 mM, and wherein the alcohol acyltransferase is of plant origin and wherein the plant belongs to a genus of Malus.

2. The method for producing a methacrylic acid ester according to claim 1 , comprising transforming isobutyryl-CoA to form the methacrylyl-CoA, wherein the isobutyryl-CoA is produced from 2-oxoisovaleric acid.

3. The method for producing a methacrylic acid ester according to claim 1 , wherein said alcohol or phenol is a linear or branched C1-10 unsubstituted alcohol, aralkyl alcohol or phenol.

4. The method for producing a methacrylic acid ester according to claim 3 , wherein the methacrylic acid ester accumulated has a concentration of at least 0.010 mM.

5. The method for producing a methacrylic acid ester according to claim 1 , wherein the methacrylic acid ester accumulated has a concentration of at least 0.010 mM.

6. The method for producing a methacrylic acid ester according to claim 1 , wherein said alcohol or phenol is selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, tert-butanol, n-pentylalcohol, isopentyl alcohol, tert-pentyl alcohol, n-hexyl alcohol, isohexyl alcohol, 2-hexyl alcohol, dimethylbutyl alcohol, ethylbutyl alcohol, heptyl alcohol, octyl alcohol, 2-ethylhexyl alcohol, benzyl alcohol and phenol.

7. The method for producing a methacrylic acid ester according to claim 1 , wherein the methacrylic acid ester accumulated has a concentration of at least 0.010 mM.

8. The method for producing methacrylic acid ester according to claim 1 , wherein the alcohol acyltransferase is expressed by a genetically modified microorganism that has been transformed to express the alcohol acyltransferase.

9. The method for producing methacrylic acid ester according to claim 8 , wherein the genetically modified microorganism belongs to the Rhodococcus genus.

10. A method for producing a methacrylic acid ester, the method comprising:

transforming isobutyryl-CoA or 3-hydroxyisobutyryl-CoA to form methacrylyl-CoA, and

contacting methacrylyl-CoA with an alcohol or a phenol in the presence of an alcohol acyltransferase, wherein the methacrylic acid ester accumulated has a concentration of at least 0.001 mM, and wherein the alcohol acyltransferase is of plant origin and wherein said plant is selected from the group consisting of Malus pumila, Malus domestica, Malus baccata, Malus halliana, Malus floribunda , and Malus prunifolia.

Assignments (2)
CHANGE OF NAME Recorded Jul 10, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043136/0132 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 4, 2014
From: SATO, EIJI; YU, FUJIO; MIZUNASHI, WATARU; NAKAJIMA, EIJI
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 034377/0897 →
Priority Claims (3)
JP 2012-198840 · Sep 10, 2012 · national
JP 2013-160300 · Aug 1, 2013 · national
JP 2013-170404 · Aug 20, 2013 · national
Continuity (1)
Related Publication 20150184207A1 · Jul 2, 2015