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Method for producing 2-hydroxyisobutyric acid and methacrylic acid from acetone cyanohydrin

A technology of acetone cyanohydrin and hydroxyisobutyric acid, applied in the direction of chemical instruments and methods, microorganism-based methods, biochemical equipment and methods, etc., can solve the problems of lack, low waste production, enzyme inactivation, etc.

Inactive Publication Date: 2005-07-06
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, U.S. 5,756,306 teaches that "When using nitrilase or nitrile hydratase to hydrolyze or hydrate α-hydroxynitrilase to produce α-oxoacid or α-hydroxyamide, there is a problem that the enzyme is inactivated in the short term
[0010] The problem to be solved is still the lack of microbial catalysts for the easy conversion of acetone cyanohydrin to 2-hydroxyisobutyric acid in a process characterized by high conversion, high concentration and high selectivity, compared to previously known The method has additional advantages of low process temperature and low waste yield

Method used

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  • Method for producing 2-hydroxyisobutyric acid and methacrylic acid from acetone cyanohydrin
  • Method for producing 2-hydroxyisobutyric acid and methacrylic acid from acetone cyanohydrin

Examples

Experimental program
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Effect test

Embodiment 1

[0104] Hydrolysis of acetone cyanohydrin to 2-hydroxyl by Pseudomonas testosteroni 5-MGAM-4D cells Isobutyric acid

[0105] A suspension of 0.383g (pasty wet cells) of Pseudomonas testosterone 5-MGAM-4D cells (ATCC55744) in 5.56mL, 50mM potassium phosphate buffer (pH6.0) was placed in a 15mL polypropylene centrifuge tube, Then 51.0 mg of acetone cyanohydrin was added (the final concentration of acetone cyanohydrin in the suspension was 0.10 M) and the resulting suspension was mixed at 25° C. on a rotating platform. The sample for analysis (0.180 mL) was mixed with 0.020 mL of 1.0 M propionic acid (HPLC external standard), centrifuged, and the supernatant was analyzed by HPLC for acetone cyanohydrin, acetone and 2-hydroxyisobutyric acid. After 4 h, the yields of 2-hydroxyisobutyric acid, 2-hydroxyisobutyramide and acetone were 73.5%, 0% and 20.4%, respectively, and no acetone cyanohydrin remained.

Embodiment 2

[0107] Hydrolysis of acetone cyanohydrin to 2-hydroxyisobutyric acid by Pseudomonas testosteroni 22-1

[0108]A suspension of 0.343 g (pasty wet cells) of Pseudomonas testosteroni 22-1 cells (ATCC PTA-1853) in 5.61 mL, 50 mM potassium phosphate buffer (pH 6.0) was placed in a 15 mL polypropylene centrifuge tube , and then add 51.0 mg of acetone cyanohydrin (the final concentration of acetone cyanohydrin in the suspension is 0.10 M), and mix the resulting suspension at 25° C. on a rotating platform. The sample for analysis (0.180 mL) was mixed with 0.020 mL of 1.0 M propionic acid (HPLC external standard), centrifuged, and the supernatant was analyzed by HPLC for acetone cyanohydrin, acetone and 2-hydroxyisobutyric acid. After 21 hours, the yields of 2-hydroxyisobutyric acid, 2-hydroxyisobutyramide and acetone were 40.4%, 0% and 34.5%, respectively, and the remaining acetone cyanohydrin was 18.4%.

Embodiment 3

[0110] Conversion of acetone cyanohydrin to 2-hydroxyisobutyric acid by Pseudomonas facilis 72W 0.36g (paste wet cells) Pseudomonas facilis 72W cells (ATCC 55746) in 5.58 mL of the suspension in 100 mM potassium phosphate buffer (pH 6.0) was placed in a 15 mL polypropylene centrifuge tube containing 51.0 mg of acetone cyanohydrin (the final concentration of acetone cyanohydrin in the suspension was 0.10 M), and the resulting suspension was mixed on a rotating platform at 25°C. The sample for analysis (0.180 mL) was mixed with 0.020 mL of 1.0 M propionic acid (HPLC external standard), centrifuged, and the supernatant was analyzed by HPLC for acetone cyanohydrin, acetone, 2-hydroxyisobutyric acid and 2-hydroxy isobutyramide. After 22 hours, the yields of 2-hydroxyisobutyric acid, 2-hydroxyisobutyramide and acetone were 22.0%, 0% and 70.2%, respectively, and the remaining acetone cyanohydrin was 2.5%.

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Abstract

The present invention relates to a process for the production of 2-hydroxyisobutyric acid in which acetone cyanohydrin is converted to 2-hydroxyisobutyric acid using a catalyst having nitrilase activity or using a catalyst having combined nitrile hydratase and amidase activity acid. The invention also relates to the production of methacrylic acid in which 2-hydroxyisobutyric acid prepared with said catalyst is dehydrated to produce methacrylic acid.

Description

field of invention [0001] The invention is a method for producing 2-hydroxyisobutyric acid using an enzyme catalyst. More specifically, the present invention relates to the use of catalysts with the activity of Pseudomonas facilis 72W nitrilase or a combination of Pseudomonas testosterone 5-MGAM-4D or Pseudomonas testosterone 22-1 nitrile hydratase and Amidase-active catalyst for the production of 2-hydroxyisobutyric acid from acetone cyanohydrin. 2-Hydroxyisobutyric acid can be used as an intermediate in the production of methacrylic acid. Background of the invention [0002] Methacrylic acid and its esters are widely used in the production of polyacrylate sheets, cast products, coatings and impact modifiers. It is also used in products such as detergent builders, flow modifiers, motor oil additives, insoluble inks, paints and polishes. Although several production methods for the preparation of methacrylic acid exist, the hydrolysis of methacrylamide sulfate (prepared wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/377C07C51/44C12N1/21C12N9/78C12P7/40C12P7/42C12R1/19
CPCC07C51/377C07C51/44C12N9/78C12P7/42C07C57/04C07C59/00C07C57/02
Inventor S·乔汉R·迪科西莫R·D·法隆J·E·加瓦甘L·E·曼泽M·S·佩恩
Owner EI DU PONT DE NEMOURS & CO
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