Alkoxylated fatty esters and derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-9187712-B2
Application number	US-201113878972-A
Country	US
Kind code	B2
Filing date	Oct 25, 2011
Priority date	Oct 25, 2010
Publication date	Nov 17, 2015
Grant date	Nov 17, 2015

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

We claim:

1. An anionic emulsifier for agricultural applications comprising:
(a) 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; or
(b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

2. A nonionic emulsifier for agricultural applications comprising:
(a) 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:
R2—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; or
(b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

3. An agricultural solvent comprising:
(a) 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; or
(b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

4. A water-soluble herbicide composition comprising:
(a) 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; or
(b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

5. An antimicrobial composition comprising:
(a) 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; or
(b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

Assignees

• 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
• 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

• C11C3/08 Primary

  with fatty acids · CPC title

• A61K8/416

  Quaternary ammonium compounds (A61K8/35 takes precedence) · CPC title

• A01N41/04

  Sulfonic acids; Derivatives thereof · CPC title

• C07C219/08

  having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C11C3/00

  Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom (sulfonated fats or oils C07C309/62; factice C08H; drying oils C09F) · CPC title