Method for polyol synthesis from triacylglyceride oils

Patent metadata

Field	Value
Publication number	US-10189761-B2
Application number	US-201615736999-A
Country	US
Kind code	B2
Filing date	Jun 27, 2016
Priority date	Jun 24, 2015
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

A method for preparation of polyols from an unsaturated TAG oil that involves first epoxidizing the unsaturated TAG oil; then subjecting the epoxidized TAG oil to transesterification using a diol and/or triol in the presence of a catalyst to produce hydroxyalkyl esters of fatty acid epoxides; and finally hydroxylating the transesterification product using a diol and/or triol and a solid acid catalyst to obtain a polyol with relatively high hydroxyl value and low viscosity.

First claim

What is claimed is:

1. A method for the preparation of polyols from an unsaturated triacylglycerol (TAG) oil comprising the steps of:
(a) fully or partially epoxidizing the unsaturated TAG oil to obtain an epoxidized TAG oil;
(b) transesterifying the epoxidized TAG oil using a diol and/or triol in the presence of a catalyst and a solvent, to produce a hydroxyalkyl esters of fatty acid epoxides; and
(c) hydroxylating the transesterification product using a diol and/or triol and a catalyst to obtain a polyol.

2. The method of claim 1 , wherein the unsaturated TAGs comprises canola oil, high oleic canola oil, sunflower oil, juvenile canola oil, flax oil, camelina oil, solin oil, yellow mustard oil, brown mustard oil, oriental mustard oil, palm oil olein, palm oil, palm kernel oil, soy oil, high erucic acid rapeseed oil, hemp oil, corn oil, olive oil, peanut oil, safflower oil, cottonseed oil or mixtures thereof, and the catalyst of step (c) comprises a solid acid catalyst.

3. The method of claim 2 , wherein the unsaturated TAG oil comprises canola oil.

4. The method of claim 2 wherein the unsaturated TAG oil comprises flax oil.

5. The method of claim 1 , wherein in step (a), the unsaturated TAG oil is epoxidized with an oxidizing agent and a carboxylic acid.

6. The method of claim 5 , wherein the oxidizing agent comprises hydrogen peroxide and the carboxylic acid comprises formic acid.

7. The method of claim 5 , wherein the unsaturated TAG is mixed with the oxidizing agent at a temperature of about 20° to about 40° C.

8. The method of claim 7 , wherein the temperature is subsequently gradually increased to about 40° to about 60° C. as the acid is added slowly.

9. The method of claim 8 , wherein the epoxidized unsaturated TAG is extracted using an organic solvent and dried.

10. The method of claim 1 , wherein in step (b) and/or (c), the diol comprises 1,2-propane diol, 1,3-propane diol, 1,4-butane diol, ethylene glycol, glycerol, glycerol acetates, or mixtures thereof.

11. The method of claim 10 , wherein the diol comprises 1,3-propane diol.

12. The method of claim 1 , wherein in step (b) the catalyst comprises an alkoxide.

13. The method of claim 12 , wherein the alkoxide comprises sodium methoxide.

14. The method of claim 1 , wherein the epoxidized unsaturated TAG is mixed with the catalyst and the diol or the triol at a temperature of about 40° to about 70° C.

15. The method of claim 14 , wherein the catalyst is neutralized by addition of a mineral acid, or a solid acid catalyst.

16. The method of claim 15 , wherein the mineral acid comprises sulfuric acid and the solid acid catalyst comprises an acidic heterogeneous macroreticular ion exchange resin.

17. The method of claim 2 , wherein in step (c), the solid acid catalyst comprises an acidic heterogeneous macroreticular ion exchange resin.

18. The method of claim 16 , wherein the solid catalyst is added to a mixture of the epoxidized unsaturated TAG and the diol and/or triol once the mixture has reached a temperature of about 40° to about 60° C.

Assignees

• Univ Alberta

Inventors

• Curtis Jonathan M
• Omonov Tolibjon S
• Kharraz Ereddad
• Kong Xiaohua
• Tavassoli-Kafrani Hossein M

Classifications

• C11C3/006

  by oxidation · CPC title

• C11C3/003

  by esterification of fatty acids with alcohols (C11C3/02 takes precedence) · CPC title

• B01J41/08

  Use of material as anion exchangers; Treatment of material for improving the anion exchange properties · CPC title

• B01J31/0212

  Alkoxylates · CPC title

• C08G18/36

  Hydroxylated esters of higher fatty acids · CPC title