Direct synthesis of cyclic carbonates using choline chloride as catalyst under mild conditions

Patent metadata

Field	Value
Publication number	US-11897860-B2
Application number	US-202217694287-A
Country	US
Kind code	B2
Filing date	Mar 14, 2022
Priority date	Mar 14, 2022
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

A method for direct synthesis of cyclic carbonates is achieved by reacting at least one epoxide with carbon dioxide in the presence of a choline catalyst, such as choline chloride, under mild conditions such as a temperature between about 25° C. to 150° C. and a pressure of from about atmospheric to 75 psi (0.52 MPa), in a cyclic carbonate solvent. The choline catalyst may be the only catalyst used, and a co-catalyst or hydrogen bond donor is not necessary. The concentration of choline catalyst in the solvent ranges from about 0.5 mol % to about 10 mol %, based on the epoxide.

First claim

What is claimed is:

1. A method for direct synthesis of cyclic carbonates comprising:
reacting at least one epoxide with carbon dioxide in the presence of a choline catalyst at a temperature between about 25° C. to 150° C. and a pressure of from about atmospheric to 75 psi (0.52 MPa), in a cyclic carbonate solvent; and
recovering at least one cyclic carbonate product.

2. The method of claim 1 where the at least one epoxide is selected from the group consisting of ethylene oxide and propylene oxide.

3. The method of claim 1 where the direct synthesis is achieved with the choline catalyst as the only catalyst.

4. The method of claim 1 where the direct synthesis is achieved in the absence of a co-catalyst or a hydrogen bond donor.

5. The method of claim 1 where the reacting is conducted at a temperature in the range of from about 50° C. to about 145° C. and the pressure is from about 30 psi (0.21 MPa) to about 50 psi (0.34 MPa).

6. The method of claim 1 where the concentration of choline catalyst in the solvent ranges from about 0.3 mol % to about 10 mol %, based on the epoxide.

7. The method of claim 1 where the molar ratio of epoxide to carbon dioxide ranges from about 1:1 to about 1:1.2.

8. The method of claim 1 where the choline catalyst is choline chloride.

9. The method of claim 1 where the cyclic carbonate solvent is the same as the cyclic carbonate product.

10. A method for direct synthesis of cyclic carbonates comprising:
reacting at least one epoxide with carbon dioxide in the presence of a choline catalyst at a temperature between about 25° C. to 150° C. and a pressure of from about atmospheric to 75 psi (0.52 MPa), in a cyclic carbonate solvent, where the molar ratio of epoxide to carbon dioxide ranges from about 1:1 to about 1:1.2; and
recovering at least one cyclic carbonate product;
where the choline catalyst is choline chloride, and where the at least one epoxide is selected from the group consisting of ethylene oxide and propylene oxide.

11. The method of claim 10 where the direct synthesis is achieved with the choline catalyst as the only catalyst.

12. The method of claim 10 where the concentration of choline catalyst in the solvent ranges from about 0.3 mol % to about 10 mol %, based on the epoxide.

13. The method of claim 10 where the cyclic carbonate solvent is the same as the cyclic carbonate product.

14. A method for direct synthesis of cyclic carbonates comprising:
reacting at least one epoxide with carbon dioxide in the presence of a choline catalyst at a temperature between about 50° C. to about 145° C. and a pressure of from about 30 psi (0.21 MPa) to about 50 psi (0.34 MPa), in a cyclic carbonate solvent; and
recovering at least one cyclic carbonate product.

15. The method of claim 14 where the at least one epoxide is selected from the group consisting of ethylene oxide and propylene oxide.

16. The method of claim 14 where the direct synthesis is achieved with the choline catalyst as the only catalyst.

17. The method of claim 14 where the concentration of choline catalyst in the solvent ranges from about 0.5 mol % to about 10 mol %, based on the epoxide.

18. The method of claim 14 where the molar ratio of epoxide to carbon dioxide ranges from about 1:1 to about 1:1.2.

19. The method of claim 14 where the choline catalyst is choline chloride.

Assignees

• Baker Hughes Oilfield Operations Llc

Inventors

• Carrasco Analette
• Weers Jerry J
• Blackwell Catherine C
• Murugesan Sankaran
• Wang Xiaofeng
• Nugent Douglas
• Roberts Corby A

Classifications

• C07D317/38 Primary

  Ethylene carbonate · CPC title

• B01J31/0239

  Quaternary ammonium compounds · CPC title

• C07C2527/24

  Nitrogen compounds · CPC title

• C07D317/36

  Alkylene carbonates; Substituted alkylene carbonates · CPC title

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title