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AssigneeUnion Carbide Chemicals & Plastics Technology Corporation
InventorsJohn R. Briggs, Wei-Jun Peng, Brian M. Roesch, Anthony G. Abatjoglou, Donald L. Morrison
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A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an a-electronwithdrawing group, such as, an a,β-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property. Further, a process for reversion of phosphonium ion ligand degradation product(s) back to useful triorganophosphine ligand(s), the reversion involving treating a reaction product fluid containing the degradation product(s) with an inert gas, hydrogen, synthesis gas, or a mixture thereof under conditions sufficient to regenerate the triorganophosphine ligand(s).
A method of minimizing the production of one or more phosphonium ion ligand degradation products in a reaction process wherein a polyunsaturated olefin is reacted in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin comprising an α,β-unsaturated aldehyde, the minimization method comprising conducting the reaction process with a triorganophosphine ligand having a ligand cone angle greater than 135° or a pKa of less than 8.3, under process conditions sufficient to minimize the formation of phosphonium ion ligand degradation product(s) such that the rate of ligand usage is less than about 2 grams ligand per liter reaction fluid per day.
A process of reverting a phosphonium ion ligand degradation product or mixture of such products back to triorganophosphine ligand(s), the phosphonium ion ligand degradation product or mixture of such products being capable of reversion to useful triorganophosphine ligand and comprising an adduct of a triorganophosphine ligand and a conjugated functionalized olefin comprising an α,β-unsaturated aldehyde;
An integrated process for carbonylation of a polyunsaturated olefin or mixture thereof comprising (a) contacting a polyunsaturated olefin or mixture thereof with carbon monoxide in the presence of hydrogen, and in the presence of a transition metal-triorganophosphine ligand complex catalyst and free triorganophosphine ligand, under process conditions sufficient to prepare a reaction product fluid comprising a transition metal-triorganophosphine ligand complex catalyst, optionally free triorganophosphine ligand, one or more reaction products, by-products, and/or intermediate products including an α,β-unsaturated aldehyde and one or more phosphonium ion ligand degradation products capable of reversion to useful ligand;
An integrated process for carbonylation of a polyunsaturated olefin or a mixture thereof comprising (a) contacting a polyunsaturated olefin or mixture thereof with carbon monoxide in the presence of hydrogen, and in the presence of a transition metal-triorganophosphine ligand complex catalyst and free triorganophosphine ligand, under process conditions sufficient to prepare a reaction product fluid comprising a transition metal-triorganophosphine ligand complex catalyst, optionally free triorganophosphine ligand, one or more reaction products, by-products, and/or intermediate products including an α,β-unsaturated aldehyde, and one or more phosphonium ion ligand degradation products capable of reversion;
Dependencies are inferred from the claim text.