3-Hydroxycarboxylic acid production and use in branched polymers
AssigneeE. I. Du Pont de Nemours and Company
InventorsMichael G. Bramucci, Robert Dicosimo, Robert Fallon, John E. Gavagan, Frank Herkes, Lech Wilczek
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Abstract
This invention relates to a process for the preparation of a 3-hydroxycarboxylic acid from a 3-hydroxynitrile. More specifically, 3-hydroxyvaleronitrile is converted to 3-hydroxyvaleric acid in high yield at up to 100 % conversion, using as an enzyme catalyst 1) nitrile hydratase activity and amidase activity or 2) nitrilase activity of a microbial cell. 3-Hydroxyvaleric acid is used as a substitute for ε-caprolactone in the preparation of highly branched copolyester.
Claims18
A process for hydrolyzing 3-hydroxynitrile to 3-hydroxycarboxylic acid comprising the steps of:
- (a) contacting a 3-hydroxynitrile in an aqueous reaction mixture with an enzyme catalyst characterized by 1) nitrile hydratase and amidase activity or 2) nitrilase activity;
- and
- (b) optionally, recovering the 3-hydroxycarboxylic acid produced in step (a).
A process for preparing 3-hydroxyvaleric acid comprising the steps of:
- (a) contacting 3-hydroxyvaleronitrile in an aqueous reaction mixture with an enzyme catalyst characterized by
- 1) nitrile hydratase activity and amidase activity of microbial cells selected from the group consisting of Acidovorax facilis 72W (ATCC 55746), Comamonas testosteroni 22-l(ATCC PTA-1853), Comamonas testosteroni 5-MGAM-4D (ATCC 55744), Dietzia sp. ADL1 (ATCC PTA-1854), Syctalidium spp. 3LD-122P (ATCC PTA-1855), Rhodococcus sp. 25-1 (ATCC PTA-1856), and Pseudomonas putida 5B-MGN-2P (NRRL-B-18668);
- or
- 2) nitrilase activity of microbial cells selected from the group consisting of Acidovorax facilis 72-PF-15 (ATCC 55747), Acidovorax facilis 72-PF-17 (ATCC 55745), and Acidovorax facilis 72W (ATCC 55746), the Acidovorax facilis 72W (ATCC 55746) heat-treated to inactivate nitrile hydratase and amidase activities;
- and
- (b) optionally, recovering 3-hydroxyvaleric acid produced in step (a).
A process for preparing 3-hydroxyvaleric acid comprising the steps of:
- (a) contacting 3-hydroxyvaleronitrile in an aqueous reaction mixture with an enzyme catalyst characterized by nitrile hydratase activity and amidase activity of microbial cells selected from the group consisting of Acidovorax facilis 72W (ATCC 55746), Comamonas testosteroni 22- 1 (ATCC PTA-1853), Comamonas testosteroni 5-MGAM-4D (ATCC 55744), Dietzia sp. ADL1 (ATCC PTA-1854), Syctalidium spp. 3LD-122P (ATCC PTA-1855), Rhodococcus sp. 25-1 (ATCC PTA-1856), and Pseudomonas putida 5B-MGN-2P (NRRL-B-18668);
- and
- (b) optionally, recovering 3-hydroxyvaleric acid produced in step (a).
A highly branched copolyester comprising at least two repeat units derived from at least one linear 3-hydroxycarboxylic acid or its ester of the structure R2O-CR4R5CR6R7C(O)OR1 and at least one hyperbranching hydroxycarboxylic acid or its ester of the structure (R2O)n—R—[C(O)OR1]m, wherein R is C1-12 hydrocarbyl radical with n+m free valencies, R1 is H, C1-12 or hydroxyl substituted C1-12 hydrocarbyl radical, R3, R4, R5, R6, R7 is H or C1-12 hydrocarbyl radical, R2 is H or (O)C R3, n+m is 3 or more, and provided that one of n and m is 1.
A process for synthesizing a highly branched copolyester product comprising the steps of:
- (a) contacting and heating a mixture of
- 1) at least one hyperbranching hydroxycarboxylic acid or its ester of the structure (R2O)n—R—[C(O)O R1]m, wherein R is C1-12 hydrocarbyl radical with n+m free valencies, R1 is H, C1-12 or hydroxyl substituted C1-12 hydrocarbyl radical, R3, R4, R5, R6, R7 is H or C1-12 hydrocarbyl radical, R2 is H or (O)C R3, n+m is 3 or more, and provided that one of n and m is 1,
- 2) a linear 3-hydroxycarboxylic acid or its ester of the structure R2O—C R4 R5C R6 R7C(O)O R1, and
- 3) an esterification catalyst;
- and
- (b) collecting the highly branched copolyester product of step (a).
A process for synthesizing a highly branched copolyester product:
- (a) contacting a 3-hydroxynitrile in an aqueous reaction mixture with an enzyme catalyst characterized by
- 1) nitrile hydratase and amidase activity of microbial cells selected from the group consisting of Acidovorax facilis 72W (ATCC 55746), Comamonas testosteroni 22-1(ATCC PTA-1853), Comamonas testosteroni 5-MGAM-4D (ATCC 55744), Dietzia sp. ADL1 (ATCC PTA-1854), Syctalidium spp. 3LD-122P (ATCC PTA-1855), Rhodococcus sp. 25-1 (ATCC PTA-1856), and Pseudomonas putida 5B-MGN-2P (NRRL-B-18668);
- or
- 2) nitrilase activity of microbial cells selected from the group consisting of Acidovorax facilis 72-PF-15 (ATCC 55747), Acidovorax facilis 72-PF-17 (ATCC 55745), and Acidovorax facilis 72W (ATCC 55746), the Acidovorax facilis 72W (ATCC 55746) heat-treated to inactivate nitrile hydratase and amidase activities;
- (b) contacting and heating a mixture of
- (1) at least one hyperbranching hydroxycarboxylic acid of the structure (R2O)n—R—[C(O)O R1]m, wherein R is C1-12 hydrocarbyl radical with n+m free valencies, R1 is H, C1-12 or hydroxyl substituted C1-12 hydrocarbyl radical, R3, R4, R5, R6, R7 is H or C1-12 hydrocarbyl radical, R2 is H or O(O)CR3, n+m is 3 or more, and provided that one of n and m is 1,
- (2) a linear 3-hydroxycarboxylic acid of the structure R2O—C R4 R5C R6 R7C(O)O R1 recovered from step (a), and
- (3) a esterification catalyst;
- and
- (c) collecting the highly branched copolyester product of step (b).
Isolated microorganisms characterized by nitrile hydratase activity and amidase activity and selected from the group consisting of Comamonas testosteroni 22-1 (ATCC PTA-1853), Dietzia sp. ADL1 (ATCC PTA-1854), Scytalidium spp. 3LD-122P (ATCC PTA-1855), and Rhodococcus sp. 25-1 (ATCC PTA-1856).
Dependencies are inferred from the claim text.