Cyclopropenimines for activation of carbon dioxide

Patent metadata

Field	Value
Publication number	US-12415889-B2
Application number	US-202217821094-A
Country	US
Kind code	B2
Filing date	Aug 19, 2022
Priority date	Aug 19, 2022
Publication date	Sep 16, 2025
Grant date	Sep 16, 2025

Abstract

A process, apparatus, and material for generating polymers are disclosed. Generating the polymers comprises reacting carbon dioxide (CO2) with a cyclopropenimine (CPI). Generating the polymers further comprises reacting monomers with a product of the reaction between the CPI and the CO2.

First claim

What is claimed is:

1. A process of generating polymers, comprising:
reacting carbon dioxide (CO 2 ) with a cyclopropenimine (CPI); and
reacting monomers with a product of the reacting, wherein the monomers comprise a monomer having nucleophilic functional groups.

2. The process of claim 1 , wherein the monomers further comprise a monomer having halide functional groups or sulfonate functional groups.

3. The process of claim 1 , wherein the nucleophilic functional groups comprise hydroxyl groups.

4. The process of claim 3 , wherein the reacting the monomers with the product generates a polycarbonate.

5. The process of claim 1 , wherein the nucleophilic functional groups comprise amine groups.

6. The process of claim 5 , wherein the reacting the monomers with the product generates a polyurethane.

7. The process of claim 1 , wherein the reacting the CO 2 with the CPI comprises adding the CO 2 to a suspension of the CPI in a polar organic solvent.

8. The process of claim 1 , wherein the reacting the CO 2 with the CPI comprises obtaining the CO 2 from air.

9. The process of claim 1 , wherein the CPI is incorporated into a support material.

10. The process of claim 1 , wherein the CPI is a superbase.

11. The process of claim 1 , wherein the CPI comprises electron-donating amine substituents and wherein the product of the reacting the CO 2 with the CPI is a CPI-CO 2 adduct comprising a tris(amino)cyclopropenium (TAC) ion that is stabilized by the electron-donating amine substituents.

12. The process of claim 11 , wherein the reacting the product with the monomers results in formation of a polymer and a conjugate acid of the CPI-CO 2 adduct, wherein the polymer is polycarbonate or polyurethane.

13. The process of claim 12 , further comprising recovering the CPI from the conjugate acid in a biphasic process comprising mixing the conjugate acid with an aqueous alkaline solution and a non-polar organic solvent.

14. The process of claim 11 , wherein the CPI-CO 2 adduct has the following structure:

wherein each R is an organic substituent, and wherein the starred bond is to a carbon atom.

15. The process of claim 1 , wherein the CPI has the following structure:

wherein each R is an organic substituent, and wherein the starred bond is to a carbon atom.

16. The process of claim 15 , wherein the starred bond is a bond to a polymer repeat unit.

17. The process of claim 15 , wherein the organic substituent is cyclohexyl.

18. The process of claim 1 , wherein the CPI is a functional group bound to a polystyrene solid support.

19. The process of claim 1 , wherein the reacting the CO 2 with the CPI comprises:
providing an absorption column packed with CPI-functionalized particles; and
passing atmospheric gas containing the CO 2 through the absorption column.

Assignees

• IBM
• Univ Columbia

Inventors

• Wu Dino
• Campos Luis M
• Park Nathaniel H
• Hedrick James L
• Kwon Junho

Classifications

• C08G64/1608

  saturated · CPC title

• C08G71/04 Primary

  Polyurethanes · CPC title

• C08G64/205

  characterised by the apparatus used · CPC title

• C08G64/323 Primary

  and alcohols · CPC title