Method of fabricating fatty acids through transacylation

Patent metadata

Field	Value
Publication number	US-9586886-B1
Application number	US-201615133418-A
Country	US
Kind code	B1
Filing date	Apr 20, 2016
Priority date	Apr 20, 2016
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

Fatty acids are produced through transacylation. An organic nitrogen-containing compound is reacted with alkyl sultone to generate a white solid of a zwitterionic compound. After being purified and dried, the white solid is powdered to be reacted with a Bronsted strong acid for obtaining a clear viscous water-based acidic ionic liquid (IL) as a catalyst used used to effectively process transacylation between oil and acetic acid (HOAc) for fabricating fatty acid (FFA) and glycerol triacetate (GTA). Therein, unsaturated fatty acid is simultaneously processed through addition acetoxylation to obtain stabilized acetoxy fatty acid (AFFA). After, HOAc is recycled through vacuuming. Then, the product and the IL are stratified. The product at upper layer is taken out. The IL at lower layer can be recycled for processing transacylation and addition acetoxylation repeatedly. Therein, fatty acids including the stabilized AFFA are obtained from the product after taking out GTA through vacuum distillation.

First claim

What is claimed is:

1. A method of fabricating fatty acids through transacylation, comprising steps of:
(a) reacting an organic nitrogen-containing compound with an alkyl sultone to obtain a white solid of a zwitterionic compound; after being purified and dried, obtaining a powder of said white solid to be reacted with a Bronsted strong acid in acetic acid (HOAc) to obtain a clear viscous water-based acidic ionic liquid (IL),
wherein a mole ratio of said Bronsted strong acid to said zwitterionic compound is 1.0˜3.0;

(b) adding a mixture of an oil (triglyceride, TG) and HOAc in said IL; using said oil and HOAc as a reactant feedstock and said IL as a catalyst to process transacylation and addition acetoxylation under reaction conditions of a temperature of 50˜150 celsius degrees (° C.) and a reaction time of 1˜72 hours (hr),
wherein a molar ratio of said IL to said oil is 0.2˜2.0 and a molar ratio of HOAc to said oil (HOAc/TG) in said reactant feedstock is 5˜80; and

(c) after reactions, recycling HOAc through vacuuming by heating under a reduced pressure; stratifying a product and said IL by staying still; taking out said product at upper layer and leaving said IL at lower layer to be recycled to repeatedly process transacylation and addition acetoxylation with said reactant feedstock added; and obtaining fatty acids, including a stabilized acetoxy fatty acid (AFFA), from said product at upper layer after taking out glycerol triacetate (GTA) through vacuum distillation.

2. The method according to claim 1 ,
wherein said organic nitrogen-containing compound is selected from a group consist of an alkylimidazole, an alkylpyridine and an alkylamine.

3. The method according to claim 2 ,
wherein said organic nitrogen-containing compound has an alkyl group of C m H 2m+1 , and m is 1˜18.

4. The method according to claim 1 ,
wherein said alkyl sultone has an alkyl group of C n H 2n , and n is 3˜6.

5. The method according to claim 1 ,
wherein said Bronsted strong acid is selected from a group consist of sulfuric acid (H 2 SO 4 ), an alkyl sulfonic acid (R—SO 3 H) and heteropoly acid (HPA).

6. The method according to claim 5 ,
wherein said alkyl sulfonic acid is selected from a group consist of fluorosulfuric acid (FSO 3 H, FS), trifluoromethane sulfonic acid (CF 3 SO 3 H, TFMSA) and p-toluenesulfonic acid (p-CH 3 —C 6 H 4 —SO 3 H, P-TSA).

7. The method according to claim 5 ,
wherein said HPA is selected from a group consist of phosphotungstic acid (H 3 PW 12 O 40 ), phosphomolybdic acid (H 3 PMo 12 O 40 ), silicotungstic acid (H 4 SiW 12 O 40 ) and silicomolybdic acid (H 4 SiMO 12 O 40 ).

8. The method according to claim 7 ,
wherein said HPA is calcined at a temperature of 100˜500° C. to remove crystal water.

9. The method according to claim 1 ,
wherein said Bronsted acid is sulfuric acid or alkyl sulfonic acid; and
wherein a molar ratio of said IL to TG is 1.0˜1.5.

10. The method according to claim 1 ,
wherein said Bronsted acid is an HPA; and
wherein a molar ratio of said IL to TG is 0.2˜0.5.

11. The method according to claim 1 ,
wherein a molar ratio of HOAc to said oil in said reactant feedstock is 40˜60.

12. The method according to claim 1 ,
wherein said transacylation is processed under conditions of a reaction temperature of 100˜110° C. and a reaction time of 24˜48 hrs.

13. The method according to claim 1 ,
wherein said oil is selected from a group consist of a waste edible oil, an epoxy oil and an energy crop oil.

14. The method according to claim 13 ,
wherein said energy crop oil is a non-edible oil selected from a group consist of jatropha oil, castor oil, high-acid algae oil and pongamia oil.

Assignees

• Cpc Corp Taiwan

Inventors

• Wu Jung-Chung
• Huang Ming-Yu
• Lin Jann-Chen
• Wang Yih-Ping

Classifications

• C07C67/02 Primary

  by interreacting ester groups, i.e. transesterification · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C67/29 Primary

  by introduction of oxygen-containing functional groups · CPC title

• C07C67/04 Primary

  by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds · CPC title

• C07C51/00

  Preparation of carboxylic acids or their salts, halides or anhydrides (of acids by hydrolysis of oils, fats or waxes C11C) · CPC title