Alkyl alkoxylates containing unique end groups
View Patent ↗Described is a process for the alkoxylation of alcohols with I, Cl, or CH 3 CO 2 endgroups, using alkylene epoxides in the presence of boron based catalysts.
1. A process comprising: contacting one or more alcohols of the formula R 1 —OH with one or more 1,2 alkylene epoxides of the formula Q(O),
wherein Q is a linear alkylene group of the formula C y H 2y where y is an integer from 2 to 10,
R 1 is Y—R′ where R′ is a linear, branched, cyclic, or aromatic hydrocarbyl group, optionally substituted, having from 1 to 30 carbon atoms, and Y is I, Br, Cl or CH 3 CO 2 ;
at a temperature from about 60° C. to about 200° C. and a pressure from ambient atmospheric pressure to about 1035 KPa;
in the presence of a catalyst at a molar ratio of alcohol to catalyst of from about 200 to 15,
wherein the catalyst is MB(OR 1 ) x (X) 4-x or B(OR 1 ) 3 /MX, where M is Na + , K + , Li + , R 2 R 3 R 4 R 5 N + , or R 2 R 3 R 4 R 5 P + , where R 2 , R 3 , R 4 , and R 5 independently are hydrocarbyl groups, X is Br, F, or I, and x is 1 to 3;
to form an alkyl alkoxylate of the formula R 1 O(QO) m H where m is from 1 to 20.
2. The process of claim 1 wherein the alkylene epoxide is ethylene oxide, propylene oxide, butylene oxide, or a mixture thereof.
3. The process of claim 1 wherein the alkylene epoxide is ethylene oxide.
4. The process of claim 1 wherein the catalyst is formed in situ.
5. The process of claim 1 where M is R 2 R 3 R 4 R 5 N + and R 2 , R 3 , R 4 , and R 5 are alkyl groups of 1 to 4 carbon atoms.
6. The process of claim 1 wherein R′ is a alkyl group having from 2-10 carbons.
7. The process of claim 1 wherein R′ is CH 2 CH 2 .
8. The process of claim 1 wherein the alkyl alkoxylate of the formula R 1 O(QO) m H is a telomeric mixture.
9. The process of claim 8 wherein the average value of m is from about 6 to about 12.
10. A composition of the formula R 1 O(QO) m H that is a telomeric mixture, wherein
Q is a linear alkylene group of the formula C y H 2y where y is from 2 to 10, and
R 1 is Y—R′ where R′ is a linear, branched, cyclic, or aromatic hydrocarbyl group, optionally substituted, having from 1 to 30 carbon atoms, Y is I, Br, Cl or CH 3 CO 2 , and m is from 1 to 20.
11. The composition of claim 10 wherein Y is I or Br.
12. The composition of claim 10 wherein R′ is a alkyl group having from 2-10 carbons.
13. The composition of claim 10 wherein R′ is CH 2 CH 2 .
14. The composition of claim 13 wherein the average value of m is from about 6 to about 12.