# US 10,870,869 B2 · Enzymatic method for preparing glyceryl butyrate

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- Number: US 10,870,869 B2
- Document ID: US10870869B2
- Status: Granted
- Kind: B2
- Application number: 16/348,890
- Filed: 2017-11-08
- Published: 2019-09-12
- Granted: 2020-12-22
- Earliest claimed: 2016-11-11
- Assignees: South China University of Technology
- Applicants: South China University of Technology
- Inventors: Yonghua Wang; Weifei Wang; Bo Yang; Dongming Lan; Fanghua Wang; Xuehui Li; Dongqi Zhu; Daoming Li; Zhigang Li; Huayong Chen
- Web page: https://patentgrep.com/patent/US10870869B2

## CPC

- C12P 7/6454: by esterification
- C12N 9/20: Triglyceride splitting, e.g. by means of lipase
- C12Y 301/01003: Triacylglycerol lipase (3.1.1.3)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12Y: ENZYMES

## Abstract

An enzymatic method for preparing glyceryl butyrate, comprising: (1) carrying out an esterification reaction between n-butyric acid and glycerol using lipase as a catalyst, ethyl acetate and/or ethyl formate as an additive; (2) separating the reaction product, recovering the additive by distillation under reduced pressure to obtain glyceryl butyrate. The invention uses lipase as a catalyst to catalyze the esterification reaction of n-butyric acid and glycerin at normal temperature and normal pressure, reduces the energy consumption of the reaction. Also, the reaction condition is mild, no side reaction happens, and no water-carrying agent is used. In addition, the additive increases the catalytic efficiency of the lipase and the conversion rate of butyric acid.

## Claims

### Claim 1

An enzymatic method for preparing glyceryl butyrate, comprising:
(1) carrying out an esterification reaction between n-butyric acid and glycerol using lipase as a catalyst and ethyl acetate and/or ethyl formate as an additive;
(2) separating the reaction product and recovering the additive by distillation under reduced pressure to obtain glyceryl butyrate.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the additive is added in an amount of 10%-60% by mass of the n-butyric acid.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the molar ratio of the n-butyric acid to the glycerol in step (1) is 3:1-1:3.

### Claim 4 (depends on 1)

The method according to any of claim 1, wherein the lipase is added in an amount of 0.5%-10% by mass of the n-butyric acid.

### Claim 5 (depends on 4)

The method according to claim 4, wherein the lipase in step (1) is selected from at least one of lipase of Rhizopus, Aspergillus, Mucor, bacteria and yeast, and pancreatic lipase.

### Claim 6 (depends on 4)

The method according to claim 4, wherein the esterification reaction is carried out at 20° C.-50° C. with stirring at a speed of 200 rpm or more.

### Claim 7 (depends on 4)

The method according to claim 4, wherein the separating in step (2) is natural stratification, then the organic phase is recovered, and ethyl acetate is distilled under reduced pressure to obtain glyceryl butyrate.

### Claim 8 (depends on 2)

The method according to claim 2, wherein the lipase is added in an amount of 0.5%-10% by mass of the n-butyric acid.

### Claim 9 (depends on 8)

The method according to claim 8, wherein the lipase in step (1) is selected from at least one of lipase of Rhizopus, Aspergillus, Mucor, bacteria and yeast, and pancreatic lipase.

### Claim 10 (depends on 8)

The method according to claim 8, wherein the esterification reaction is carried out at 20° C.-50° C. with stiffing at a speed of 200 rpm or more.

### Claim 11 (depends on 8)

The method according to claim 8, wherein the separating in step (2) is natural stratification, then the organic phase is recovered, and ethyl acetate is distilled under reduced pressure to obtain glyceryl butyrate.

### Claim 12 (depends on 3)

The method according to claim 3, wherein the lipase is added in an amount of 0.5%-10% by mass of the n-butyric acid.

### Claim 13 (depends on 12)

The method according to claim 12, wherein the lipase in step (1) is selected from at least one of lipase of Rhizopus, Aspergillus, Mucor, bacteria and yeast, and pancreatic lipase.

### Claim 14 (depends on 12)

The method according to claim 12, wherein the esterification reaction is carried out at 20° C.-50° C. with stiffing at a speed of 200 rpm or more.

### Claim 15 (depends on 12)

The method according to claim 12, wherein the separating in step (2) is natural stratification, then the organic phase is recovered, and ethyl acetate is distilled under reduced pressure to obtain glyceryl butyrate.