Carbonated estolides and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-9850222-B2
Application number	US-201615224934-A
Country	US
Kind code	B2
Filing date	Aug 1, 2016
Priority date	Aug 13, 2015
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

Disclosed herein are the conversion of estolide compounds having unsaturated fatty acid groups into estolides containing cyclic carbonate moieties and methods of making and using the same. The estolides containing a cyclic carbonate may be used to produce urethane containing estolides.

First claim

We claim:

1. An estolide containing a cyclic carbonate having the Formula

wherein x and y are each equal to 1 or greater than 1 and x is independent from each occurrence and y is independent from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

2. A method of making an estolide containing a cyclic carbonate, said method comprising
(a) forming epoxidized estolide by reacting formic acid and H 2 O 2 with at least one estolide compound of the Formula

wherein x and y are each equal to 1 or greater than 1 and x is independent from each occurrence and y is independent from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

(b) reacting said epoxidized estolide with an alkylammonium salt and pressurized CO 2 to form an estolide containing a cyclic carbonate having the Formula

wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

wherein residual epoxide or unsaturated groups may still be present.

3. The method according to claim 2 , wherein residual epoxide or unsaturated groups are not present.

4. An estolide containing a cyclic carbonate having the Formula

wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

said estolide containing a cyclic carbonate prepared by the method according to claim 2 .

5. A urethane containing estolide having the Formula

wherein x and y are each equal to 1 or greater than 1 and x is independent from each occurrence and y is independent from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

R 11 and R 12 are independently selected from H, any alkyl chain [C1-C14], any branched alkyl chain [C1-C14], any alkyl chain containing an amine or hydroxyl group [C1-C14].

6. A method to making a urethane containing estolide, said method comprising
(a) forming epoxidized estolide by reacting formic acid and H 2 O 2 with at least one estolide compound of the Formula

wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

(b) reacting said epoxidized estolide with an alkylammonium salt and pressurized CO 2 to form an estolide containing a cyclic carbonate having the Formula

wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
wherein n is 0-9,
R 1 is H, or an linear alkyl chain or a branched alkyl chain or

wherein R 9 and R 10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
and R 2 -R 7 are independently selected from —CH 2 —, —C═C—, or

(c) and reacting said estolide containing a cyclic carbonate with an amine or diamine to form a urethane containing estolide having the Formula

R 11 and R 12 are independently selected from H, any alkyl chain [C1-C14], any branched alkyl chain [C1-C14], any alkyl chain containing an amine or hydroxyl group [C1-C14].

7. A urethane containing estolide having the Formula

wherein x and y are each equal to 1 o

Assignees

• Us Agriculture

Inventors

• Doll Kenneth M
• Isbell Terry
• Cermak Steven C
• Kenar James A

Classifications

• C07C271/20

  to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C07C269/04

  from amines with formation of carbamate groups · CPC title

• C07D317/36 Primary

  Alkylene carbonates; Substituted alkylene carbonates · CPC title