Polymers of ethylene oxide and carbon dioxide
AssigneeCornell University
InventorsGeoffrey W. Coates, Scott Allen, Tsuyoshi Ando
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Abstract
The present disclosure is directed, in part, to methods of synthesizing a poly(ethylene carbonate) polymer from the reaction of ethylene oxide (EO) and carbon dioxide (CO2) in the presence of a metal complex. The present disclosure also provides novel metal complexes. In one aspect, the metal complex is of formula (I), wherein R1, R2, R3, M, X and Ring A are as defined herein.
Claims35
A method of synthesizing a poly(ethylene carbonate) polymer, comprising a step of reacting ethylene oxide and carbon dioxide in the presence of a metal complex, wherein the metal complex is of the formula:
- wherein:
- the poly(ethylene carbonate) polymer is made up of Y, and optionally Z, and wherein the percentage of Y is greater than the percentage of Z,
- M is a metal selected from zinc, cobalt, chromium, aluminum, titanium, ruthenium or manganese;
- X is absent or is a nucleophilic ligand;
- each instance of R1, R2, and R3 is, independently, selected from hydrogen, halogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, and optionally substituted heteroaryl, or R1 and R2, or R2 and R3, are joined to form an optionally substituted aryl or optionally substituted heteroaryl ring;
- and
- Ring A forms an optionally substituted 5- to 6-membered ring.
22-31. (canceled)
37-53. (canceled)
A method of synthesizing a poly(ethylene carbonate) polymer, comprising a step of reacting ethylene oxide with carbon dioxide in the presence of a cobalt complex,
- wherein the cobalt complex is any one of the formulae:
- wherein X is absent or is a nucleophilic ligand.
A metal complex of the formula:
- wherein:
- M is a metal selected from zinc, cobalt, chromium, aluminum, titanium, ruthenium or manganese;
- X is absent or is a nucleophilic ligand;
- R3 is, independently, selected from hydrogen, halogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, and optionally substituted heteroaryl;
- Ring A forms an optionally substituted cyclohexyl or phenyl ring;
- R7 and R9 are, independently, selected from hydrogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl;
- wherein at least one of R7 and R9 is selected from the group consisting of:
- —[C(CH3)2CH2CH2N(Bu)3]+, —C(CH3)2CH2C(CH3)3, —CH(CH2CH3)C6H5, —CH(C6H5)CH═CH2, —C(CH3)2CH2CH3, 1-methyl-cyclohexyl, cyclohexyl and —C(CH3)2Ph;
- wherein R9 is other than —[C(CH3)2CH2CH2N(Bu)3]+ when R7 is —[C(CH3)2CH2CH2N(Bu)3]+;
- wherein R9 is other than hydrogen when R7 is —CH(CH2CH3)C6H5;
- wherein R9 is other than —C(CH3)2CH2C(CH3)3 when R7 is —C(CH3)2CH2C(CH3)3;
- wherein R9 is other than —C(CH3)3 when R7 is —CH(C6H5)CH═CH2;
- wherein R9 is other than —C(CH3)3 when R7 is —C(CH3)2CH2CH3;
- wherein R9 is other than —C(CH3)2CH2CH3 when R7 is —C(CH3)2CH2CH3;
- wherein R9 is other than —C(CH3)3 when R7 is 1-methyl-cyclohexyl;
- wherein R9 is other than —C(CH3)2CH2CH3 when R7 is 1-methyl-cyclohexyl;
- wherein R9 is other than —CH3 when R7 is cyclohexyl;
- and
- wherein R9 is other than —C(CH3)2Ph when R7 is —C(CH3)2Ph.
56-61. (canceled)
A metal complex of the formula:
- wherein:
- M is a metal selected from zinc, cobalt, chromium, aluminum, titanium, ruthenium or manganese;
- X is absent or is a nucleophilic ligand;
- R7 and R9 are, independently, selected from hydrogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl;
- and
- R4A, R4B, R5A, R5B, and R6A, R6B are independently, selected from hydrogen, halogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, and/or, R4A and R4B, and/or R5A and RSB, and/or and R6A and R6B are optionally joined to form an oxo (=O) group, an oxime (=NORa) group, an imine (=NN(Ra)2) group, an alkenyl (=C(Rb)2) group, and/or a 3- to 6-membered spirocyclic ring, wherein each instance of Ra and Rb is, independently, hydrogen or optionally substituted aliphatic, wherein optionally two Ra groups or two Rb groups are joined to form a 3- to 6-membered ring.
63-72. (canceled)
A metal complex of the formula:
- wherein:
- M is a metal selected from zinc, cobalt, chromium, aluminum, titanium, ruthenium or manganese;
- X is absent or is a nucleophilic ligand;
- R1, R2, R3 are, independently, selected from hydrogen, halogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, and optionally substituted heteroaryl;
- R7 and R9 are, independently, selected from hydrogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl;
- and
- Ring A forms an optionally substituted cyclohexyl or phenyl ring.
74-98. (canceled)
Dependencies are inferred from the claim text.