Preparation and use of high quality esterquats from rice bran fatty acids

Patent metadata

Field	Value
Publication number	US-11773347-B2
Application number	US-201917258952-A
Country	US
Kind code	B2
Filing date	Jul 10, 2019
Priority date	Jul 11, 2018
Publication date	Oct 3, 2023
Grant date	Oct 3, 2023

Abstract

Esterquats find major applications as fabric softeners. After Tallow fatty acids and Palm oil fatty acids, fatty acids from sustainable sources like Rice bran fatty acids (RBFA) are desired. RBFA is formed as a by-product during refining of Rice bran oil and hence it is contained in the non edible portion of the oil. The production of high quality esterquats from this by-product is challenging, but the invention describes a process to produce high quality esterquats having low odour and a low acid value. This enhances easy formulation of various products and better customer acceptance. Liquid esterquats produced from RBFA enable e.g. cold processing for fabric softener formulations.

First claim

The invention claimed is:

1. A process for production of an esterquat composition, wherein the process comprises the steps of:
(i) esterification of a fatty acid or a mixture of fatty acids with an alkanolamine to form an ester amine or a mixture of ester amines; and
(ii) quaternization of the amino group of the resultant ester amine or the amino groups of the mixture of ester amines with a quaternizing agent,
wherein the fatty acid or mixture of fatty acids is a rice bran fatty acid or a mixture of rice bran fatty acids, and are from non-edible sources generated during refinement of a rice bran oil, and
wherein the fatty acid or mixture of fatty acids is directly esterified, is subjected to a chemical processing before being esterified, is changed before being esterified by using one or more separation techniques, or a combination thereof.

2. The process according to claim 1 , wherein the alkanolamine in the esterification step (i) is a trialkanolamine.

3. The process according to claim 1 , wherein at least a part of the quaternization step (ii), is carried out without a solvent, and a solvent is optionally added only after the at least partial completion, of the quaternization step (ii).

4. The process according to claim 1 , wherein a solvent is used after the quaternization step (ii) and the solvent is an alcohol.

5. The process according to claim 1 , wherein the crude rice bran oil, is a side product of rice bran processing.

6. The process according to claim 1 , wherein the rice bran fatty acid or mixture of rice bran fatty acids is subjected to a step of chemical processing before the esterification step (i), wherein the step of chemical processing is selected from the group consisting of halogenation, hydrohalogenation, hydroboration, ozonolysis, Diels-Alder reactions, hydrogenation, epoxidation and any combination thereof.

7. The process according to claim 1 , wherein the composition of rice bran fatty acids or mixture of rice bran fatty acids is changed before the esterification step (i) by using one or more separation techniques selected from the group consisting of crystallisation, winterisation, distillation, sublimation, filtration, chromatography including column, flash, high performance liquid chromatography, liquid-liquid extraction, solid-liquid-extraction and any combination thereof.

8. The process according to claim 1 , wherein the esterification step (i) is carried out at temperatures between 50 and 250° C. and/or the quaternisation step is carried out at temperatures from 20 to 120° C.

9. The process according to claim 1 , wherein the molar ratio of fatty acids to alkanolamine in esterification step (i) is from 1:2 to 3:1.

10. The process according to claim 1 , wherein the molar ratio of ester amine to quaternising agent in the quaternisation step (ii) is from 2:1 to 1:3.

11. An esterquat composition product prepared by a process according to claim 1 .

12. The esterquat composition produced by the process according to claim 1 , wherein the acid value of the esterquat composition is lower than 7 mg KOH/g of the sample.

13. The esterquat composition produced by the process according to claim 1 , wherein the esterquat composition has an active esterquat content of above 0.7 meq/g as measured by Epton titration.

14. The esterquat composition produced by the process according to claim 1 , wherein the content of a methylated solvent is below 10000 ppm.

15. The esterquat composition produced by the process according to claim 1 , having a colour value on the Gardner colour scale of less than 8.

16. The esterquat composition produced by the process according to claim 1 , wherein the esterquat composition is a liquid esterquat composition.

17. A fabric softener composition comprising the esterquat composition product according to claim 11 .

Assignees

• Clariant Int Ltd

Inventors

• Wadekar Sushant Dattaram
• Contractor Prerak Rajendrakumar

Classifications

• C11D3/0015 Primary

  liquid · CPC title

• C07C227/28

  from natural products · CPC title

• C07C229/22

  the carbon skeleton being further substituted by oxygen atoms · CPC title

• C11D1/62

  Quaternary ammonium compounds · CPC title

• C11D1/64

  of unknown constitution {, e.g. natural products} · CPC title