IP Library Granted Patent US 11,802,298
Granted Patent B2
US 11,802,298 · App. 17/082,124 · Granted Oct 31, 2023

Decanedioic acid produced by microbial fermentation process and preparation method thereof

Inventors: Min Xu (Shanghai, CN); Yingli Hao (Shanghai, CN); Chen Yang (Shanghai, CN); Naiqiang Li (Shanghai, CN); Xiucai Liu (Shanghai, CN)
Assignees: Cathay Biotech Inc.; CIBT America Inc.
C12P7/6409C07C55/20C08G63/16C08G69/26C12P7/44
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Quick Facts
Patent No.
US 11,802,298
App. No.
17/082,124
Granted
Oct 31, 2023
Kind
B2
Abstract

The present invention provides a decanedioic acid produced by microbial fermentation process, in which the content of C10 aliphatic acid and C10 hydroxy aliphatic acid is maintained at a very low level. The present invention also provides a preparation method of the decanedioic acid and a polymer prepared by using the decanedioic acid as monomer. The decanedioic acid provided by the present invention is prepared by microbial fermentation process. The decanedioic acid product which is produced through the processes of microbial fermentation and separation has a higher purity, a higher thermal stability, and a lower impurity content. The decanedioic acid provided by the present invention could satisfy the requirements of high grade product of polyamide or polyester to produce polymer with excellent qualities. The preparation method of the decanedioic acid provided by the present invention which has many advantages of mild reaction conditions, environmental friendliness, high yield, and good product quality, may replace the chemical method to be used in industrial scale production of the decanedioic acid.

Claims (30)

1. A method of preparing decanedioic acid, comprising:

culturing Candida tropicalis to obtain a seed culture;

inoculating the obtained seed culture with a fermentation medium;

starting a fermentation process to produce fermentation broth by adding decane; and

purifying the obtained fermentation broth to give the decanedioic acid;

wherein the fermentation medium comprises the following ingredients: 1-10 g/L potassium nitrate, 1-10 g/L potassium phosphate monobasic, and 1-4 g/L ammonium sulfate, and

wherein the content of aliphatic acid comprising 10 carbons is less than 200 ppm, and the content of hydroxy aliphatic acid comprising 10 carbons is less than 300 ppm.

2. The method according to claim 1 , wherein the fermentation medium also comprises the following ingredients: 0-50 g/L glucose, 2-10 g/L corn steep liquor and 1-8 g/L yeast extract.

3. The method according to claim 1 , wherein the fermentation medium comprises the following ingredients: 1.2-2.5 g/L potassium nitrate, 1.8-3.5 g/L potassium phosphate monobasic, and 1.2-2 g/L ammonium sulfate.

4. The method according to claim 1 , wherein the decane is added when OD 620 of the fermentation medium with a dilution of 1:30 reaches more than 0.5.

5. The method according to claim 4 , wherein the OD 620 of the fermentation medium with a dilution of 1:30 is maintained at 0.3-0.8 in the fermentation process.

6. The method according to claim 1 , wherein relative dissolved oxygen is maintained at more than 10% (v/v).

7. The method according to claim 6 , wherein the relative dissolved oxygen is maintained at 10% to 70% in the fermentation process.

8. The method according to claim 1 , wherein pH value is maintained at 5.0-8.0 in the fermentation process.

9. The method according to claim 1 , wherein the content of decane in fermentation system is maintained at more than or equal to 1% (v/v) by feeding the decane in a continuous way or in a batch way in the fermentation process, and wherein the content of decane in the obtained fermentation broth is maintained at less than or equal to 0.5% (v/v) when the fermentation process is terminated.

10. The method according to claim 1 , wherein the Candida tropicalis is Candida tropicalis CAT N145.

11. The method according to claim 1 , wherein purifying the obtained fermentation broth comprises the following steps:

S1: removing impurities by one or more separation processes consisting of membrane filtration, plate and frame filtration, and centrifugation to obtain decanedioic acid crude product;

S2: purifying the obtained decanedioic acid crude product by one or more crystallization processes to obtain decanedioic acid crystals; and

S3: washing and drying the decanedioic acid crystals to yield the decanedioic acid.

12. The method according to claim 11 , wherein a crystallization solvent is used in the one or more crystallization processes in the step S2;

wherein the crystallization solvent is selected from the group consisting of water, ethanol, acetic acid, ethyl acetate, and butyl acetate.

13. The method according to claim 12 , the crystallization process using water as solvent comprising: mixing the decanedioic acid crude product with a certain amount of water to obtain a mixture with a 5%-10% (w/v) decanedioic acid content; heating the mixture to a temperature of 95° C.-110° C., followed by cooling down to 25° C.-30° C. to crystallize; and obtaining the crystals through centrifugation or plate and frame filtration.

14. The method according to claim 12 , the crystallization process using acetic acid as solvent comprising: heating the solution of the decanedioic acid crude product in acetic acid to a temperature of 90° C.-95° C., then cooling down to 20° C.-30° C. to crystallize;

wherein the mass ratio of the decanedioic acid crude product to acetic acid is 1/2 to 1/4.

15. The method according to claim 12 , wherein the crystallization solvent is acetic acid, and the content of acetic acid in the obtained decanedioic acid crystals is maintained at less than 500 ppm.

16. A decanedioic acid product produced by the method according to claim 1 .

17. The decanedioic acid product according to claim 16 , wherein the thermal stability of the decanedioic acid is more than 90%.

18. A polymer prepared by using the decanedioic acid produced by the method according to claim 1 as monomer, wherein the polymer is selected from polyamide or polyester.

19. The polymer according to claim 18 , wherein the polymer is polyamide polymerized by the decanedioic acid and aliphatic amine comprising 5 to 12 carbons, and wherein the aliphatic amine is selected from pentamethylene diamine, hexamethylene diamine, or decamethylene diamine.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2023
From: XU, MIN; HAO, YINGLI; YANG, CHEN; LI, NAIQIANG; LIU, XIUCAI
To: CATHAY R&D CENTER CO., LTD.; CATHAY INDUSTRIAL BIOTECH LTD.
Reel/Frame 065004/0952 →
CHANGE OF NAME Recorded Sep 25, 2023
From: SHANGHAI CATHAY BIOTECH R&D CENTER LTD.
To: CATHAY BIOTECH INC.
Reel/Frame 065004/0984 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2023
From: CATHAY INDUSTRIAL BIOTECH LTD.
To: CIBT AMERICA INC.
Reel/Frame 065004/0996 →
Priority Claims (1)
CN 201710653289.0 · Aug 2, 2017 · national
Continuity (2)
Continuation 16049119 · Jul 30, 2018
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