Alkoxylated fatty esters and derivatives from natural oil metathesis

A nonionic emulsifier for agricultural applications comprising:

• (a) an alkoxylated fatty ester composition comprising a reaction product of a metathesis-derived C10-C17 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—R1
• wherein:
• R1 is C1-C4 alkyl;
• AO is C2-C4 oxyalkylene;
• R2 is R3—CH═CH—(CH2)7— or R1(AO)nO—CO—(CH2)7—CH═CH—(CH2)7—;
• R3 is hydrogen or C1-C7 alkyl;
• and n, which is the average number of oxyalkylene units, has a value within the range of 1 to 100;
• and
• wherein when R3 is C1-C7 alkyl, the acid or ester derivative reactant has at least 1 mole % of trans-Δ9 unsaturation;
• or
• (b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

An agricultural solvent comprising:

• (a) an alkoxylated fatty ester composition comprising a reaction product of a metathesis-derived C10-C17 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—R1
• wherein:
• R1 is C1-C4 alkyl;
• AO is C2-C4 oxyalkylene;
• R2 is R3—CH═CH—(CH2)7— or R1(AO)nO—CO—(CH2)7—CH═CH—(CH2)7—;
• R3 is hydrogen or C1-C7 alkyl;
• and n, which is the average number of oxyalkylene units, has a value within the range of 1 to 100;
• and
• wherein when R3 is C1-C7 alkyl, the acid or ester derivative reactant has at least 1 mole % of trans-Δ9 unsaturation;
• or
• (b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

A water-soluble herbicide composition comprising:

• (a) an alkoxylated fatty ester composition comprising a reaction product of a metathesis-derived C10-C17 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—R1
• wherein:
• R1 is C1-C4 alkyl;
• AO is C2-C4 oxyalkylene;
• R2 is R3—CH═CH—(CH2)7— or R1(AO)nO—CO—(CH2)7—CH═CH—(CH2)7—;
• R3 is hydrogen or C1-C7 alkyl;
• and n, which is the average number of oxyalkylene units, has a value within the range of 1 to 100;
• and
• wherein when R3 is C1-C7 alkyl, the acid or ester derivative reactant has at least 1 mole % of trans-Δ9 unsaturation;
• or
• (b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.

An antimicrobial composition comprising:

• (a) an alkoxylated fatty ester composition comprising a reaction product of a metathesis-derived C10-C17 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—R1
• wherein:
• R1 is C1-C4 alkyl;
• AO is C2-C4 oxyalkylene;
• R2 is R3—CH═CH—(CH2)7— or R1(AO)nO—CO—(CH2)7—CH═CH—(CH2)7—;
• R3 is hydrogen or C1-C7 alkyl;
• and n, which is the average number of oxyalkylene units, has a value within the range of 1 to 100;
• and
• wherein when R3 is C1-C7 alkyl, the acid or ester derivative reactant has at least 1 mole % of trans-Δ9 unsaturation;
• or
• (b) a derivative made by sulfonating or sulfitating the alkoxylated fatty ester composition.