Method of preparing bio-polyols from epoxidized fatty acid esters

Patent metadata

Field	Value
Publication number	US-10766841-B2
Application number	US-201916662321-A
Country	US
Kind code	B2
Filing date	Oct 24, 2019
Priority date	Nov 13, 2018
Publication date	Sep 8, 2020
Grant date	Sep 8, 2020

Abstract

A method of preparing bio-polyols from epoxidized fatty acid esters, wherein the bio-polyols are synthesized via hydroxylation with epoxidized fatty acid esters and ring-opening reagent, using the acidic ionic liquids as catalysts. The bio-polyols are used to synthesize bio-polyurethane and bio-polyurethane foams. The acidic ionic liquids in this process is used in esterification, epoxidation, and ring-opening reaction to synthesize bio-polyols. The ionic liquids catalysts have several advantages such as easy to separate, reusable, and may reduce pollution.

First claim

What is claimed is:

1. A method of preparing bio-polyols from epoxidized fatty acid esters comprising steps of:
replacing amphoteric compound by using alkyl sulfonic acid, wherein the alkyl sulfonic acid are synthesized with Brønsted strong acid to produce Brønsted acid IL, a molar ratio of the alkyl sulfonic acid and the Brønsted strong acid is within 1.0 to 1.5;
mixing the epoxidized fatty acid esters and the Brønsted acid IL at a predetermined ratio, adding alcohols for using as ring-opening reagent, thus producing reaction solution, wherein the reaction solution is heated within a temperature of 30° C. to 100° C. for 1 to 24 hours to cause ring-opening hydroxylation, wherein a molar ratio of the alcohols and the epoxidized fatty acid esters is within 4 to 20, and a molar ratio of the Brønsted acid IL and the epoxidized fatty acid esters is within 0.01 to 0.15; and
extracting and layering the reaction solution by using deionized water to acquire upper-layer solution and lower-layer solution, wherein the lower-layer solution consists of ionic liquid which is concentrated and dried to recycle reusable ionic liquid, and the upper-layer solution consists of bio-polyols which are extracted by using the deionized water and alkaline water and then dehydrated.

2. The method as claimed in claim 1 , wherein the alkyl sulfonic acid is C n H 2n , and the n is a positive integer within 3 to 6.

3. The method as claimed in claim 1 , wherein the Brønsted strong acid is any one of phosphoric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid.

4. The method as claimed in claim 1 , wherein a molar ratio of of the alkyl sulfonic acid in the Brønsted acid IL and the Brønsted strong acid is within 1.0 to 1.2.

5. The method as claimed in claim 1 , wherein the epoxidized fatty acid esters are epoxide of fatty acid alkyl esters, the fatty acid alkyl esters are any one of biodiesel, unsaturated fatty acid alkyl esters, and a mixture of the biodiesel and the unsaturated fatty acid alkyl esters, wherein the biodiesel is fatty acid methyl ester which is transesterificated from vegetable oil, animal oil, and waste cooking oil, wherein the unsaturated fatty acid alkyl esters is any one or a mixture of more than two of alkyloleate, alkyl linoleate, and alkyllinolenate.

6. The method as claimed in claim 1 , wherein the alcohols are any one of monohydric alcohol, polyols, and a mixture of the monohydric alcohol and the polyols, wherein the monohydric alcohol are any one of methanol, ethanol, propanol, butanol, and isomer of the methanol, the ethanol, the propanol, and the butanol, wherein the polyols are ethylene glycol, propylene glycol, butanediol, and isomer of the ethylene glycol, the propylene glycol and the butanediol, and glycerol.

7. The method as claimed in claim 5 , wherein a reacting time of the ring-opening hydroxylation of epoxide of the biodiesel is within 1 to 20 hours, a reacting time of ring-opening hydroxylation of epoxide of the unsaturated fatty acid alkyl esters is within 4 to 24 hours, and a reacting time of ring-opening hydroxylation of epoxide of the biodiesel and the unsaturated fatty acid alkyl esters is within 1 to 20 hours.

8. The method as claimed in claim 1 , wherein a molar ratio of the alcohols and the epoxidized fatty acid esters is within 4 to 12.

9. The method as claimed in claim 1 , wherein a molar ratio of the Brønsted acid IL and the epoxidized fatty acid esters is within 0.05 to 0.12.

10. The method as claimed in claim 9 , wherein a molar ratio of the Brønsted acid IL and the epoxidized fatty acid esters is within 0.05 to 0.10.

11. The method as claimed in claim 1 , wherein a reacting temperature of ring-opening hydroxylation is within 40° C. to 80° C.

12. The method as claimed in claim 11 , wherein a reacting temperature of ring-opening hydroxylation is within 40° C. to 60° C.

Assignees

• Cpc Corp Taiwan
• Cpc Corp

Inventors

• Tu You-Liang
• Lin Ya-Shiuan
• Tsai Ming-Tsang
• Li Chiu-Ping

Classifications

• B01J31/0277

  comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature · CPC title

• B01J31/0225

  comprising sulfonic acid groups or the corresponding salts · CPC title

• B01J2531/002

  Materials · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G18/36 Primary

  Hydroxylated esters of higher fatty acids · CPC title