Method for preparing thermally cleavable surfactants without deprotonation
View Patent ↗The present invention describes surfactants of formula (I), wherein R, R N , and m are defined herein, processes for their preparation, and methods for their decomposition.
1. A process to prepare a compound according to formula (I),
wherein
R N is —L—G, wherein
L is -aryl-, -heteroaryl-, —(C 8 -C 30 )alkyl-, —(C 6 -C 20 )haloalkyl-, —(C 3 -C 10 )cycloalkyl-, or -heterocyclyl-; and
G is —S(O) 2 OM,
wherein M is H, Li, Na, K, Rb, or Cs;
R is —L 1 —R′, wherein,
L 1 is a bond, —(C 1 -C 4 )alkyl-O—, -aryl-, or —(C 3 -C 10 )cycloalkyl-; and
R′ is —(C 8 -C 30 )alkyl, —(C 6 -C 20 )haloalkyl, or —((C 1 -C 4 )alkyl-O) j —R″, wherein
j is an integer from 2 to 100; and
R″ is —H or methyl; and m is an integer from 1 to 4, comprising the steps of:
(i) contacting a furanyl compound of formula (IV),
wherein
R is —L 1 —R′, wherein,
L 1 is a bond, —(C 1 -C 4 )alkyl-O—, -aryl-, or —(C 3 -C 10 ) cycloalkyl-; and
R′ is —(C 8 -C 30 )alkyl, —(C 6 -C 20 )haloalkyl, or —((C 1 -C 4 )alkyl-O) j -R″, wherein
j is an integer from 2 to 100; and
R″ is —H or methyl; and
m is an integer from 1 to 4;
with a maleimide compound of formula (V),
wherein
R N is —L—G, wherein
L is -aryl-, -heteroaryl-, —(C 8 -C 30 )alkyl-, —(C 6 -C 20 )haloalkyl-, —(C 3 -C 10 )cycloalkyl-, or -heterocyclyl-; and
G is —S(O) 2 OM,
wherein M is H, Li, Na, K, Rb, or Cs;
in an optional polar organic solvent; and
(iii) heating the composition to a temperature of about 25° C. to about 55° C.
2. The process according to claim 1 , wherein
R N is —L—G, wherein
L is -aryl-, —(C 8 -C 30 )alkyl-, or —(C 6 -C 20 )haloalkyl-; and
G is —S(O) 2 OM,
wherein M is H, Li, Na, K, Rb, or Cs.
3. The process according to claim 1 , wherein
R is —L 1 —R′, wherein,
L 1 is a bond or —(C 1 -C 4 )alkyl-O—; and
R′ is —(C 8 -C 30 )alkyl or —(C 6 -C 20 )haloalkyl.
4. The process according to claim 1 , wherein the maleimide compound is of formula (VI),
5. The process according to claim 4 , wherein maleimide compound is N-(4-sodium sulfophenyl) maleimide.
6. The process according to claim 1 , wherein m is 1 or 2.
7. The process according to claim 1 , wherein the furanyl compound is of formula (VII),
8. The process according to claim 1 , wherein
R is —L 1 —R′, wherein,
L 1 is a bond or —(C 1 -C 4 )alkyl-O—; and
R′ is —(C 8 -C 30 )alkyl or —(C 6 -C 20 )haloalkyl.
9. The process according to claim 1 , wherein the furanyl compound is 2-docecylfuran or 2-octadecyfuran.
10. The process according to claim 1 , wherein the polar organic solvent is water, methanol, ethanol, i-propanol, t-butanol, glyme, diglyme, tetrahydrofuran, acetonitrile, dimethylsulfoxide, N,N-dimethylfuran, N,N-dimethylacetamide, N-methylpyrridinone, and mixtures thereof.
11. The process according to claim 10 , wherein the solvent is N,N-dimethylformamide.
12. The process according to claim 1 , wherein the temperature is from about 30° C. to about 55° C.
13. The process according to claim 1 , wherein the temperature is from about 40° C. to about 55° C.
14. The process according to claim 1 , wherein the temperature is from about 45° C. to about 55° C.
15. The process according to claim 1 , wherein the temperature is from about 50° C. to about 55° C.