Process for preparing cyclic carbonate esters from olefins in a single reaction mixture
AssigneeExxon Research & Engineering Co.
InventorsRichard G. Austin, Robert C. Michaelson, Richard S. Myers
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Abstract
A process for reacting in admixture, an olefin with oxygen, CO, and water, to form a cyclic alkylene carbonate, in the presence of a catalyst composition comprising a catalytically active osmium compound, copper containing co-catalyst I (e.g. CuBr.sub.2) and a co-catalyst II (e.g. pyridine) is disclosed.
Claims17
A process for preparing at least one cyclic alkylene carbonate ester which comprises reacting in a liquid phase admixture at least one olefin containing at least one ethylenic unsaturation, water, molecular oxygen, and carbon monoxide in the presence of an osmium containing catalyst composition, thereby forming said cyclic alkylene carbonate ester product, with the proviso that the total amount of water present in said liquid phase during reaction being a molar ratio of water to ethylenic unsaturation to be reacted of from about 0.1:1 to about 20:1;
- said catalyst composition comprising:
- (A) at least one catalytically active osmium containing compound;
- (B) an amount of at least one copper containing compound co-catalyst I effective to increase at least one of the rate and selectivity in the formation of said cyclic carbonate ester product relative to its absence;
- (C) at least one co-catalyst II in an amount effective to increase the rate of said cyclic carbonate ester product formation relative to its absence, said co-catalyst II being selected from at least one member of the group consisting of:
- (i) 1,4-diazabicyclo (2.2.2) octane;
- (ii) hexamethylenetetraamine;
- and
- (iii) at least one compound represented by at least one of the structural formulae:
- ##STR30## wherein:
- (1) in structural formula (XIIa):
- (a) Z.sub.2 to Z.sub.6 independently represent a member selected from the group consisting of a methylidyne group, a substituted methylidyne group represented, by the formula .tbd.CR.sub.11, and a tertiary nitrogen group;
- said R.sub.11 substituent being selected from the group consisting of hydroxy, alkyl, aryl, aralkyl and alkaryl;
- and
- (b) any two of said R.sub.11 substituents located on adjacent carbons of said Z.sub.2 to Z.sub.5 groups of structural formula (XIIa) together can constitute part of a monocyclic or fused bicyclic ring system, which partial ring systems are (i) aromatic, or heteroaromatic in nature, said heteroatom being nitrogen, and (ii) completed by, and fused with parent structure (XIIa) through said adjacent carbons of Z.sub.2 to Z.sub.5 groups;
- and
- (2) in structural formula (XIIb):
- (a) Z.sub.7 to Z.sub.9 independently represent a member selected from the group consisting of a methylidyne group, and a substituted methylidyne group represented by the formula .tbd.CR'.sub.11 wherein R'.sub.11 is independently selected from the group consisting of alkyl, aryl, aralkyl, and alkaryl;
- and
- (b) R.sub.12 is selected from the group consisting of alkyl, aryl, aralkyl, and alkaryl.
Dependencies are inferred from the claim text.