Process of manufacturing surfactants and lubricants

Patent metadata

Field	Value
Publication number	US-11970574-B2
Application number	US-201816646060-A
Country	US
Kind code	B2
Filing date	Sep 14, 2018
Priority date	Sep 14, 2017
Publication date	Apr 30, 2024
Grant date	Apr 30, 2024

Abstract

A method of producing an alcohol ethoxylate surfactant or lubricant, the method including reacting a low molecular weight initiator with ethylene oxide in the presence of a polymerization catalyst, the low molecular weight initiator having a nominal hydroxyl functionality at least 1, and the polymerization catalyst being a Lewis acid catalyst having the general formula M(R1)I(R2)I(R3)I(R4)0 or 1, whereas M is boron, aluminum, indium, bismuth or erbium, R1, R2, R3, and R4 are each independent, R1 includes a first fluoroalkyl-substituted phenyl group, R2 includes a second fluoroalkyl-substituted phenyl group or a first fluoro/chloro-substituted phenyl group, R3 includes a third fluoroalkyl-substituted phenyl group or a second fluoro/chloro-substituted phenyl group, and optional R4 includes a functional group or functional polymer group, R1 being different from at least one of R2 and R3. The method further including forming an alcohol ethoxylate surfactant or lubricant having a number average molecular weight of greater than the number average molecular weight of the low molecular weight initiator in the presence of the Lewis acid catalyst.

First claim

The invention claimed is:

1. A method of producing an alcohol ethoxylate surfactant or lubricant, the method comprising:
reacting a low molecular weight initiator with ethylene oxide in the presence of a polymerization catalyst, the low molecular weight initiator having a nominal hydroxyl functionality at least 1, and the polymerization catalyst being a Lewis acid catalyst having the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas M is boron, aluminum, indium, bismuth or erbium, R 1 , R 2 , R 3 , and R 4 are each independent, R 1 includes a first fluoroalkyl-substituted phenyl group, R 2 includes a second fluoroalkyl-substituted phenyl group or a first fluoro or chloro-substituted phenyl group, R 3 includes a third fluoroalkyl-substituted phenyl group or a second fluoro or chloro-substituted phenyl group, and optional R 4 includes a functional group or functional polymer group, R t being different from at least one of R 2 and R 3 ; and
forming an alcohol ethoxylate surfactant or lubricant having a number average molecular weight of greater than the number average molecular weight of the low molecular weight initiator in the presence of the Lewis acid catalyst, wherein:
the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-substituted phenyl group that is the same as the first fluoroalkyl-substituted phenyl group, and R 3 is the second fluoro or chloro-substituted phenyl group, or
the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-substituted phenyl group that is the same as the first fluoroalkyl-substituted phenyl group, and R 3 is the third fluoroalkyl-substituted phenyl group that is different from the first fluoroalkyl-substituted phenyl group, or
the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-substituted phenyl group that is different from the first fluoroalkyl-substituted phenyl group, and R 3 is the third fluoroalkyl-substituted phenyl group that is different from the first fluoroalkyl-substituted phenyl group and the second fluoroalkyl-substituted phenyl group, or
the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas at least one of R 1 , R 2 , and R 3 is a 3,4- or 3,5-bis(fluoroalkyl)-substituted phenyl group, or
the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) I .

2. The method as claimed in claim 1 , wherein the alcohol ethoxylate surfactant or lubricant has a yield of at least 60% based on actual yield of an ethylene oxide capped alcohol and a theoretical yield of the ethylene oxide capped alcohol.

3. A method of producing an alcohol ethoxylate surfactant or lubricant, the method comprising:
reacting a low molecular weight initiator with ethylene oxide in the presence of a polymerization catalyst, the low molecular weight initiator having a nominal hydroxyl functionality at least 1, and the polymerization catalyst being a Lewis acid catalyst having the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas M is boron, aluminum, indium, bismuth or erbium, R 1 , R 2 , R 3 , and R 4 are each independent, R 1 includes a first fluoroalkyl-substituted phenyl group, R 2 includes a second fluoroalkyl-substituted phenyl group or a first fluoro or chloro-substituted phenyl group, R 3 includes a third fluoroalkyl-substituted phenyl group or a second fluoro or chloro-substituted phenyl group, and optional R 4 includes a functional group or functional polymer group, R 1 being different from at least one of R 2 and R 3 ; and
forming an alcohol ethoxylate surfactant or lubricant having a number average molecular weight of greater than the number average molecular weight of the low molecular weight initiator in the presence of the Lewis acid catalyst,
wherein the low molecular weight initiator is a secondary alcohol having a number average molecular weight of less than 3,000 g/mol and the alcohol ethoxylate surfactant or lubricant is a secondary alcohol ethoxylate surfactant or lubricant.

4. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-substituted phenyl group that is the same as first fluoroalkyl-substituted phenyl group, and R 3 is the second fluoro or chloro-substituted phenyl group.

5. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-substituted phenyl group that is the same as first fluoroalkyl-substituted phenyl group, and R 3 is the third fluoroalkyl-substituted phenyl group that is different from the first fluoroalkyl-substituted phenyl group.

6. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-substituted phenyl group that is different from the first fluoroalkyl-substituted phenyl group, and R 3 is the third fluoroalkyl-substituted phenyl group that is different from the first fluoroalkyl-substituted phenyl group and the second fluoroalkyl-substituted phenyl group.

7. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas R 2 is the first fluoro or chloro-substituted phenyl group and R 3 is the second fluoro or chloro-substituted phenyl group that is the same as the first fluoro or chloro-substituted phenyl group.

8. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas at least one of R 2 and R 3 is a fluoro or chloro-fluoroalkyl-substituted phenyl group, difluoro or chloro-fluoroalkyl-substituted phenyl group, trifluoro or chloro-fluoroalkyl-substituted phenyl group, or tetrafluoro or chloro-fluoroalkyl-substituted phenyl group.

9. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) 0 or 1 , whereas at least one of R 1 , R 2 , and R 3 is a 3,4- or 3,5-bis(fluoroalkyl)-substituted phenyl group.

10. The method as claimed in claim 3 , wherein the Lewis acid catalyst has the general formula M(R 1 ) I (R 2 ) I (R 3 ) I (R 4 ) I .

11. The method as claimed in claim 10 , wherein R 4 is a cyclic ether having 3-10 carbon atoms.

12. The method as claimed in claim 10 , wherein R 4 is a ketone having 3-10 carbon atoms.

13. An alcohol ethoxylate surfactant or lubricant prepared using the method as claimed in claim 1 .

14. A composition that includes the alcohol ethoxylate surfactant or lubricant prepared using the method as claimed in claim 1 .

Assignees

• Dow Global Technologies Llc

Inventors

• Raghuraman Arjun
• Heath William H
• Hook Bruce D
• Yu Wanglin
• Mukhopadhyay Sukrit
• Spinney Heather A
• Wilson David R

Classifications

• C08G65/2654 Primary

  Aluminium or boron; Compounds thereof · CPC title

• C07F5/027

  Organoboranes and organoborohydrides · CPC title

• C08G18/48

  Polyethers · CPC title

• C08G18/4841

  containing oxyethylene end groups · CPC title

• C08G18/4854

  Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group · CPC title