Low-toxicity olefinic ester compositions and methods of using the same

Patent metadata

Field	Value
Publication number	US-10358409-B2
Application number	US-201514847664-A
Country	US
Kind code	B2
Filing date	Sep 8, 2015
Priority date	Sep 15, 2014
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

Compositions including certain olefinic ester compounds are generally disclosed. In some embodiments, such compositions are compositions having low toxicity, such as low aquatic toxicity. Therefore, in some embodiments, such compositions can be suitable used as solvents or as part of a solvent system for applications where low toxicity is desirable. Such uses include, but are not limited to, cleaning applications on or near waterways, use in oil or gas recovery, and the like. In some other embodiments, such compositions are treatment fluids for oil wells, and can therefore be introduced into an oil well to remove buildup and other deposits. In some embodiments, the olefinic ester compounds are derived from a natural oil or a natural oil derivative.

First claim

What is claimed is:

1. A compound of formula (I):

wherein:
R 1 is —(CH 2 ) 7 —CH═CH—CH 2 —CH 3 ;
R 2 is R 3 or -G 3 -R 3 ;
G 3 is —CH 2 — or —CH 2 —CH 2 ; and
R 3 is:
C 3-12 cycloalkyl, which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms, unsubstituted C 1-4 alkyl groups, C 1-4 fluoroalkyl groups, C 1-4 alkoxy groups, C 1-4 fluoroalkoxy groups, —OH groups, —NH 2 groups, —NH(C 1-4 alkyl) groups, —N(unsubstituted C 1-4 alkyl) 2 groups, —CN groups, —COOH groups, —COO(C 1-4 alkyl) groups, —CONH 2 groups, —CONH(C 1-4 alkyl) groups, —CON(C 1-4 alkyl) 2 groups, —CHO groups, —CO(C 1-4 alkyl) groups, hydroxy- and/or C 1-4 alkoxy-substituted C 1-4 alkyl groups, and any combinations thereof;
C 2-20 heterocycloalkyl, which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms, unsubstituted C 1-4 alkyl groups, C 1-4 fluoroalkyl groups, C 1-4 alkoxy groups, C 1-4 fluoroalkoxy groups, —OH groups, —NH 2 groups, —NH(C 1-4 alkyl) groups, —N(C 1-4 alkyl) 2 groups, —CN groups, —COOH groups, —COO(C 1-4 alkyl) groups, —CONH 2 groups, —CONH(C 1-4 alkyl) groups, —CON(C 1-4 alkyl) 2 groups, —CHO groups, —CO(C 1-4 alkyl) groups, hydroxy- and/or C 1-4 alkoxy-substituted C 1-4 alkyl groups, and any combinations thereof;
C 6-20 aryl, which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms, unsubstituted C 1-4 alkyl groups, C 1-4 fluoroalkyl groups, C 1-4 alkoxy groups, C 1-4 fluoroalkoxy groups, —OH groups, —NH 2 groups, —NH(C 1-4 alkyl) groups, —N(unsubstituted C 1-4 alkyl) 2 groups, —CN groups, —COOH groups, —COO(C 1-4 alkyl) groups, —CONH 2 groups, —CONH(C 1-4 alkyl) groups, —CON(C 1-4 alkyl) 2 groups, —CHO groups, —CO(C 1-4 alkyl) groups, hydroxy- and/or C 1-4 alkoxy-substituted C 1-4 alkyl groups, and any combinations thereof; or
C 3-20 heteroaryl, which is optionally substituted.

2. The compound of claim 1 , wherein R 2 is -G 3 -R 3 .

3. The compound of claim 1 , wherein R 2 is R 3 .

4. The compound of claim 3 , wherein R 3 is C 3-12 cycloalkyl, which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms, unsubstituted C 1-4 alkyl groups, C 1-4 fluoroalkyl groups, C 1-4 alkoxy groups, C 1-4 fluoroalkoxy groups, —OH groups, —NH 2 groups, —NH(C 1-4 alkyl) groups, —N(unsubstituted C 1-4 alkyl) 2 groups, —CN groups, —COOH groups, —COO(C 1-4 alkyl) groups, —CONH 2 groups, —CONH(C 1-4 alkyl) groups, —CON(C 1-4 alkyl) 2 groups, —CHO groups, —CO(C 1-4 alkyl) groups, hydroxy- and/or C 1-4 alkoxy-substituted C 1-4 alkyl groups, and any combinations thereof.

5. The compound of claim 4 , wherein R 3 is cyclopentyl, cyclohexyl, norbornyl, or adamantyl.

6. The compound of claim 5 , wherein R 3 is cyclohexyl.

7. The compound of claim 3 , where R 3 is C 2-2C heterocycloalkyl, which is optionally substituted with one or more substituents selected from the group consisting of halogen atoms, unsubstituted C 1-4 alkyl groups, C 1-4 fluoroalkyl groups, C 1-4 alkoxy groups, C 1-4 fluoroalkoxy groups, —OH groups, —NH 2 groups, —NH(C 1-4 alkyl) groups, —N(C 1-4 alkyl) 2 groups, —CN groups, —COOH groups, —COO(C 1-4 alkyl) groups, —CONH 2 groups, —CONH(C 1-4 alkyl) groups, —CON(C 1-4 alkyl) 2 groups, —CHO groups, —CO(C 1-4 alkyl) groups, hydroxy- and/or C 1-4 alkoxy-substituted C 1-4 alkyl groups, and any combinations thereof.

8. The compound of claim 7 , wherein R 3 is tetrahydrofuranyl, tetrahydropyranyl, or dioxanyl.

9. The compound of claim 3 , wherein R 3 is phenyl.

10. The compound of claim 3 , wherein R 3 is furanyl, oxazolyl, or isoxazolyl.

Assignees

• Elevance Renewable Sciences

Inventors

• Dantale Shubhada
• Ngantung Frederyk
• Erhan Selim

Classifications

• C07C69/75 Primary

  of acids with a six-membered ring · CPC title

• C07C69/74

  Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C69/533

  Monocarboxylic acid esters having only one carbon-to-carbon double bond · CPC title

• C07D319/12

  not condensed with other rings · CPC title