Low-toxicity olefinic ester compositions and methods of using the same
View Patent ↗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.
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.