Laundry builders and surfactants derived from bio-based hydroxyacids and epoxides

Patent metadata

Field	Value
Publication number	US-11168284-B2
Application number	US-201816216453-A
Country	US
Kind code	B2
Filing date	Dec 11, 2018
Priority date	Dec 11, 2017
Publication date	Nov 9, 2021
Grant date	Nov 9, 2021

Abstract

Fatty acid based surfactants and methods for producing fatty acid based surfactants are described. The method includes reacting a fatty acid ester epoxide with a hydroxy acid, a hydroxy ester, a polyoxyalkyl diol, or a polyamine. Any remaining esters from the original fatty acid ester epoxide or hydroxy ester can optionally be hydrolyzed. Methods for making citric acid derived surfactants are also described.

First claim

What is claimed is:

1. A method for producing a fatty acid based surfactant comprising:
reacting a fatty acid ester epoxide with a hydroxy acid in the presence of a tetrafluoroborate salt catalyst or a metal hydroxide catalyst to produce an acid with an ether functionality, a hydroxy ester in the presence of a tetrafluoroborate salt catalyst, a metal hydroxide catalyst, or a metal halide catalyst to produce a poly-ester with an ether functionality, a polyoxyalkyl diol in the presence of a tetrafluoroborate salt catalyst or a metal hydroxide catalyst to produce an ester alcohol with an ether functionality, or a polyamine in the presence of a tetrafluoroborate salt catalyst, a metal hydroxide catalyst, or a metal halide catalyst to produce an amide with an amine functionality, wherein the polyamine is ethylene diamine, spermidine, tris (2-aminoethyl)amine, or diaminohexane.

2. The method of claim 1 further comprising hydrolyzing the ester from the fatty acid ester epoxide or the hydroxy ester under basic conditions.

3. The method of claim 1 wherein the fatty acid ester epoxide is reacted with the hydroxy ester and wherein the hydroxy ester contains an alkyl group having 1 to 20 carbon atoms.

4. The method of claim 1 wherein the fatty acid ester epoxide is reacted with the hydroxy acid or hydroxy ester and wherein the hydroxy acid comprises one or more of citric acid, malic acid, lactic acid, glycolic acid, or tartaric acid, or wherein the hydroxy ester comprises one or more of triethyl citrate, trimethyl citrate, diethyl malate, dimethyl malate, ethyl lactate, methyl lactate, ethyl glycolate, methyl glycolate, ethyl tartrate, or methyl tartrate.

5. The method of claim 1 wherein the fatty acid ester epoxide is reacted with the polyoxyalkyl diol and wherein the polyoxyalkyl diol comprises one or more of diethylene glycol, triethylene glycol, poly(ethylene glycol), dipropylene glycol, tripropylene glycol, or polypropylene glycol).

6. The method of claim 1 wherein the fatty acid ester epoxide is formed by epoxidizing a fatty acid ester.

7. The method of claim 1 wherein the fatty acid ester epoxide is derived from a high oleic oil or a mid-oleic oil.

8. The method of claim 1 wherein the fatty acid ester epoxide is derived from one of more of high oleic soybean oil, high oleic algal oil, high oleic olive oil, high oleic canola oil, or high oleic sunflower oil.

9. The method of claim 1 wherein the fatty acid ester epoxide comprises one or more of epoxidized methyl oleate, epoxidized methyl soyate, epoxidized 9-decenoic acid methyl ester, epoxidized soybean oil, epoxidized algal oil, epoxidized algal oil methyl ester, epoxidized olive oil, epoxidized canola oil, or epoxidized sunflower oil.

10. The method of claim 1 wherein the fatty acid ester epoxide is derived from one of more of high oleic soybean oil, high oleic algal oil, high oleic olive oil, high oleic canola oil, or high oleic sunflower oil.

11. A method of making a citric acid derived surfactant comprising:
reacting an alkyl oxide with a citric acid trialkyl ester in the presence of a tetrafluoroborate catalyst.

12. The method of claim 1 wherein the fatty acid ester is reacted with the hydroxy acid.

13. The method of claim 1 wherein the fatty acid ester is reacted with the hydroxy ester.

14. The method of claim 1 wherein the fatty acid ester is reacted with the polyamine.

Assignees

• Battelle Memorial Institute

Inventors

• Garbark Daniel B
• Cafmeyer Jeffrey T
• Lalgudi Ramanathan S

Classifications

• C11D1/42 Primary

  Amino alcohols or amino ethers · CPC title

• C11C3/003 Primary

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

• C11D1/74

  Carboxylates or sulfonates {esters} of polyoxyalkylene glycols · CPC title

• C07C237/20

  the carbon skeleton containing six-membered aromatic rings · CPC title

• C11D1/83

  Mixtures of non-ionic with anionic compounds · CPC title