Process of manufacturing polyols

Patent metadata

Field	Value
Publication number	US-11912822-B2
Application number	US-201816642216-A
Country	US
Kind code	B2
Filing date	Sep 14, 2018
Priority date	Sep 14, 2017
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

Abstract

A method of producing a polyether polyol includes reacting a low molecular weight initiator with ethylene oxide in the presence of a polymerization catalyst, and the low molecular weight initiator has a nominal hydroxyl functionality at least 2. The polymerization catalyst is a Lewis acid catalyst having the general formula M(R1)1(R2)1(R3)1(R4)0 or 1, whereas M is boron, aluminum, indium, bismuth or erbium, R1, R2, R3, and R4 are each independent, R1 includes a fluoroalkyl-substituted phenyl group, R2 incudes a fluoroalkyl-substituted phenyl group or a fluoro/chloro-substituted phenyl group, R3 includes a fluoroalkyl-substituted phenyl group or a 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.

First claim

The invention claimed is:

1. A method of producing a polyether polyol, 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 2, and the polymerization catalyst being a Lewis acid catalyst having the general formula M(R 1 ) 1 (R 2 ) 1 (R 3 ) 1 (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 a polyether polyol 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.

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

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

4. The method as claimed in claim 1 , wherein the Lewis acid catalyst has the general formula M(R 1 ) 1 (R 2 ) 1 (R 3 ) 1 (R 4 ) 0 or 1 , whereas R 2 is the second fluoroalkyl-sustituted 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.

5. The method as claimed in claim 1 , wherein the Lewis acid catalyst has the general formula M(R 1 ) 1 (R 2 ) 1 (R 3 ) 1 (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 that same as the first fluoro or chloro-substituted phenyl group.

6. The method as claimed in claim 1 , wherein the Lewis acid catalyst has the general formula M(R 1 ) 1 (R 2 ) 1 (R 3 ) 1 (R 4 ) 0 or 1 , whereas at least one of R 2 and R 3 is a fluoro/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.

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

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

9. The method as claimed in claim 8 , wherein R 4 is a cyclic ether having 3-10 carbon atoms.

10. The method as claimed in claim 8 , wherein R 4 is a ketone having 3-10 carbon atoms.

11. The method as claimed in claim 1 , wherein the polyether polyol has a yield of at least 60% based on actual yield of an ethylene oxide capped polyol and a theoretical yield of the ethylene oxide capped polyol.

12. The method as claimed in claim 1 , wherein the low molecular weight initiator is a polyether diol or triol derived from at least one selected from propylene oxide, ethylene oxide, and butylene oxide.

13. A method of producing a polyurethane product, the method comprising:
producing a polyether polyol by 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 2, and the polymerization catalyst being a Lewis acid catalyst having the general formula M(R 1 ) 1 (R 2 ) 1 (R 3 ) 1 (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 ; the polyether polyol 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; and
providing an isocyanate.

Assignees

• Dow Global Technologies Llc

Inventors

• Raghuraman Arjun
• Heath William H
• 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

• C08G18/4841

  containing oxyethylene end groups · CPC title

• C08G18/4854

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

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title