Catalyst composition for cyclic carbonate production from CO2 and epoxides

Patent metadata

Field	Value
Publication number	US-12496575-B2
Application number	US-202017764399-A
Country	US
Kind code	B2
Filing date	Sep 30, 2020
Priority date	Sep 30, 2019
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

The present invention relates to catalyst composition for cyclic carbonate production from CO 2 and epoxides under mild conditions, which can effectively catalyze the cyclic carbonate synthesis and provides good selectivity to cyclic carbonate, wherein said catalyst composition comprising:
a) the metal complex as shown in structure (I):

wherein,
M represents transition metal atom;
R 1 , R 2 , and R 3 represent independent group selected from hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, amine group, phenyl group, benzyl group, cyclic hydrocarbon group comprising hetero atom, perfluoroalkyl group, or nitro group;
R 4 represents group selected from alkylene group, cycloalkylene group, or phenylene group;
X represents group selected from hydrogen atom, acetate group, or triflate group; and
b) the organic compound as the co-catalyst selected from compound containing nitrogen, compound of quaternary ammonium salts, or compound of iminium salts.

First claim

The invention claimed is:

1 . A catalyst composition for cyclic carbonate production from CO 2 and epoxides, wherein said catalyst composition comprises:
a) the metal complex as shown in structure (I):

wherein,
M represents transition metal atom selected from the group consisting of chromium, cobalt and iron;
R 1 , R 2 , and R 3 represent independent group selected from hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, alkoxy group, amine group, phenyl group, benzyl group, cyclic hydrocarbon group comprising hetero atom, perfluoroalkyl group, or nitro group;
R 4 represents group selected from alkylene group, cycloalkylene group, or phenylene group;
X represents group selected from halogen atom, acetate group, or triflate group; and
b) the organic compound as the co-catalyst is selected from the group consisting of 4-dimethylaminopyridine (DMAP), tetrabutylammonium bromide (TBAB), tetrabutylammonium chloride (TBAC), tetrabutylammonium iodide (TBAI), imidazolium bromide, imidazolium chloride, imidazolium iodide, bis(triphenylphosphine) iminium bromide, bis(triphenylphosphine) iminium chloride, bis(triphenylphosphine) iminium iodide, and mixtures thereof.

2 . The catalyst composition according to claim 1 , wherein in the metal complex in a), Mis chromium metal atom.

3 . The catalyst composition according to claim 1 , wherein in the metal complex in a), R 1 , R 2 , and R 3 represent independent group selected from hydrogen atom, halogen atom, alkyl group having 1 to 4 carbon atoms, alkenyl group having 1 to 4 carbon atoms, alkynyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, amine group, phenyl group, benzyl group, cyclic hydrocarbon group comprising hetero atom, perfluoroalkyl group, or nitro group.

4 . The catalyst composition according to claim 1 or 3 , wherein in the metal complex in a), R 1 , R 2 , and R 3 represent independent group selected from hydrogen atom, chlorine atom, methyl group, ethyl group, iso-propyl group, n-butyl group, tert-butyl group, methoxy group, ethoxy group, iso-propoxy group, n-butoxy group, tert-butoxy group, phenyl group, benzyl group, trifluoromethyl group, or nitro group.

5 . The catalyst composition according to claim 4 , wherein in the metal complex in a), R 1 and R 3 are tert-butyl group and R 2 is hydrogen atom.

6 . The catalyst composition according to claim 1 , wherein in the metal complex in a), R 4 represents group selected from alkylene group having 2 to 3 carbon atoms, cycloalkylene group having 6 carbon atoms, or phenylene group.

7 . The catalyst composition according to claim 1 or 6 , wherein in the metal complex in a), R 4 represents group selected from ethylene group, 1,3-propylene group, 1,2-cyclohexylene group, or 1,2-phenylene group.

8 . The catalyst composition according to claim 7 , wherein in the metal complex in a), R 4 is ethylene group.

9 . The catalyst composition according to claim 1 , wherein in the metal complex in a), X represents group selected from chlorine atom, bromine atom, iodine atom, acetate group, or triflate group.

10 . The catalyst composition according to claim 1 , wherein the metal complex in a) is selected from N—N′-bis(ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(ethylenesalicylidene)-cyclohexane-1,2-diamino metal (III) chloride, N—N′-bis(3,5-di-tert-butyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride,
N—N′-bis(3,5-di-methyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(5-methyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(5-tert-butyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-tert-butyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-methyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-trifluoromethyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-methoxy ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-nitro ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-chloro ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-trifluoromethyl ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-methoxy ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-nitro ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-chloro ethylenesalicylidene)-ethane-1,2-diamino metal (III) chloride,
N—N′-bis(3,5-di-tert-butyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3,5-di-methyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-methyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(5-methyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-tert-butyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(5-tert-butyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-tert-butyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-methyl ethylenesalicylidene)-propane-1,3-diamino metal chloride, N—N′-bis(3-tert-butyl, 5-trifluoromethyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-methoxy ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-nitro ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-chloro ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-trifluoromethyl ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-methoxy ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-nitro ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-chloro ethylenesalicylidene)-propane-1,3-diamino metal (III) chloride,
N—N′-bis(3,5-di-tert-butyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3,5-di-methyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(5-methyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(5-tert-butyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-tert-butyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-methyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-trifluoromethyl ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-methoxy ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-nitro ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-tert-butyl, 5-chloro ethylenesalicylidene)-benzene-1,2-diamino metal (III) chloride, N—N′-bis(3-methyl, 5-trifluoromethyl ethylenesalicylidene)-benzene-1,2-diamino

Assignees

• Ptt Global Chemical Public Co Ltd

Inventors

• Kiriratnikorn Jiraya
• Vongnam Kunnigar
• Thavornsin Nopparat
• Sae-Ung Pornpen
• Kaeothip Sophon
• Euapermkiati Anucha
• Phomphrai Khamphee

Classifications

• C07D317/44

  ortho- or peri-condensed with carbocyclic rings or ring systems · CPC title

• C07D317/38

  Ethylene carbonate · CPC title

• B01J2531/842

  Iron · CPC title

• B01J2531/62

  Chromium · CPC title

• B01J2531/0252

  Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde · CPC title