Alkoxylated fatty esters and derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-2016102271-A1
Application number	US-201514881283-A
Country	US
Kind code	A1
Filing date	Oct 13, 2015
Priority date	Oct 25, 2010
Publication date	Apr 14, 2016
Grant date	—

Abstract

Alkoxylated fatty ester compositions are disclosed. In one aspect, the compositions comprise a reaction product of a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with one or more alkylene oxides in the presence of an insertion catalyst to give an alkoxylated fatty ester. In another aspect, the metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or its ester derivative is reacted with a glycol ether or a glycol ether alkoxylate, to give an alkoxylated fatty ester. In yet another aspect, the metathesis-derived C 10 -C 17 monounsaturated acid or octadecene-1,18-dioic acid is reacted with one or more alkylene oxides to give a fatty acid alkoxylate, followed by etherification of the fatty acid alkoxylate.

First claim

1 . An alkoxylated fatty ester composition comprising a reaction product of a metathesis-derived C 10 -C 17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with: (a) one or more alkylene oxides in the presence of an insertion catalyst to give an alkoxylated fatty ester; (b) a glycol ether or a glycol ether alkoxylate, optionally in the presence of an esterification or transesterification catalyst, to give an alkoxylated fatty ester; or (c) one or more alkylene oxides to give a fatty acid alkoxylate, followed by etherification of the fatty acid alkoxylate;
wherein the alkoxylated fatty ester composition has the formula:
R 2 —CO—O—(AO) n —R 1

wherein: R 1 is C 1 -C 4 alkyl; AO is C 2 -C 4 oxyalkylene; R 2 is R 3 —CH═CH—(CH 2 ) 7 — or R 1 (AO) n O—CO—(CH 2 ) 7 —CH═CH—(CH 2 ) 7 —; R 3 is hydrogen or C 1 -C 7 alkyl; and n, which is the average number of oxyalkylene units, has a value within the range of 1 to 100; and
wherein when R 3 is C 1 -C 7 alkyl, the acid or ester derivative reactant has at least 1 mole % of trans-Δ 9 unsaturation.

2 . A derivative made by sulfonating or sulfitating the composition of claim 1 .

3 . The composition of claim 1 wherein the acid or ester derivative reactant has at least 25 mole % of trans-Δ 9 unsaturation.

4 . The composition of claim 1 wherein the alkylene oxide in (a) or (c) is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxides, and combinations thereof.

5 . The composition of claim 1 wherein the alkylene oxide is ethylene oxide.

6 . (canceled)

7 . The composition of claim 1 wherein AO is oxyethylene and n has a value within the range of 1 to 5.

8 . The composition of claim 1 wherein AO is oxyethylene and n has a value within the range of 5 to 15.

9 . The composition of claim 1 wherein AO is oxyethylene and n has a value within the range of 15 to 50.

10 . The composition of claim 1 wherein R 1 is methyl.

11 . (canceled)

12 . The composition of claim 1 wherein glycol ether or glycol ether alkoxylate is selected from the group consisting of C 1 -C 4 alkyl ethers of ethylene glycol, propylene glycol, and their adducts with ethylene oxide, propylene oxide, or combinations thereof.

13 . The composition of claim 1 wherein the C 10 -C 17 monounsaturated acid or ester derivative comprises a C 10 and a C 12 monounsaturated acid or ester derivative.

14 - 29 . (canceled)

Assignees

• Stepan Co

Inventors

• Allen Dave R
• Alonso Marcos
• Bernhardt Randal J
• Brown Aaron
• Buchek Kelly
• Ganguly-Mink Sangeeta
• Holland Brian
• Malec Andrew D
• Masters Ronald A
• Murphy Dennis S
• Skelton Patti
• Sook Brian
• Wiester Michael
• Wolfe Patrick Shane

Classifications

• C09K15/28

  containing nitrogen, oxygen and sulfur · CPC title

• C07C303/18

  by reaction of sulfides with compounds having functional groups with formation of sulfo or halosulfonyl groups · CPC title

• A61K8/42

  Amides · CPC title

• A01N25/02

  containing liquids as carriers, diluents or solvents · CPC title

• C07C67/02

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