Union Carbide Chemicals & Plastics Technology Corporation

Dow Global Technolgoies LLC

Dow Technology Investments LLC

Donald Lee Morrison

David Robert Bryant

Brian Michael Roesch

Jeffrey Scott Kanel

Wei-Jun Peng

John Robert Briggs

David James Miller

Michael Leo Tulchinsky

Kurt D Olson

Paul Foley

Anthony G Abatjoglou

Donald L Bunning

Kenneth Elwood Stockman

David A Babb

Zenon Lysenko

John Michael Maher

Aaron W Sanders

Alan K Schrock

Pulikkottil Jacob Thomas

Ailene Gardner Phillips

Joe D Phillips

Christopher W Derstine

Max Min Lee

H Ray Jouett

James H Gilchrist

Eric P Wasserman

Cynthia L Rand

Thomas Carl Eisenschmid

Ernst Billig

Thomas H Newman

Kenneth A Burdett

James Clair Nicholson

Bob R Maughon

Jeffrey G Hippler

Donald Leroy Bunning

Vincent Joseph Stricker

Walter C Reed

Craig Alan Beasley

Michael David Warholic

Anthony George Abatjoglou

An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates.

Aldehyde compositions derived from seed oils

A method of preparing an aromatic phosphine monosulfonate in zwitterionic form, such as dicyclohexylphenylphosphine monosulfonate zwitterion, involving contacting an aromatic phosphine with a sulfonating agent to provide a reaction mixture containing aromatic phosphine monosulfonate in acid form and unconverted sulfonating agent; quenching or removing substantially all of the unconverted sulfonating agent; partially neutralizing the aromatic phosphine monosulfonate in acid form to phase separate aromatic phosphine monosulfonate in zwitterionic form as a solid or neat liquid layer; and collecting the zwitterion as a solid or neat liquid. The zwitterion may be neutralized to form the corresponding aromatic phosphine monosulfonate metal salt, which is useful in preparing catalysts for hydroformylation processes.

Process for the monosulfonation of aromatic phosphines, and zwitterionic product derived therefrom

A non-aqueous hydroformylation process with liquid catalyst recycle involving a hydroformylation step and one or more stages of phase separation to recover a high molecular weight aldehyde product with efficient recovery of rhodium catalyst. The process includes a hydroformylation step to prepare a non-aqueous hydroformylation reaction product composition comprising one or more aldehyde products, one or more conjugated polyolefins, a rhodium-organophosphorus ligand complex, free organophosphorus ligand, and an organic solubilizing agent for said complex and said free ligand, and thereafter one or more stages of phase separation using added water under a carbon monoxide gas, hydrogen gas, or a mixture thereof. The process requires a specific range of total pressure for the hydroformylation, a specific range of total pressure for at least one of the separation stages, and a minimum sum of the total pressure of the hydroformylation step and the total pressure of the separation stage containing said gas.

Hydroformylation process and product separation with improved recovery of rhodium

An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates. An alcohol composition derived by hydrogenation of the aforementioned aldehyde composition, containing a mixture of hydroxymethyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoalcohol {mono(hydroxymethyl)}, greater than about 1 to less than about 65 percent diol {di(hydroxymethyl)}, greater than about 0.1 to less than about 10 percent triol, tri(hydroxymethyl)-substituted fatty acids or fatty acid esters; preferably greater than about 3 to less than about 35 percent saturates; and preferably, less than about 10 percent unsaturates. The alcohol composition can be converted into an oligomeric polyol for use in the manufacture of polyurethane slab stock flexible foam.

Aldehyde and alcohol compositions derived from seed oils

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 &#x3b1;-electron-withdrawing group, such as, an &#x3b1;,&#x3b2;-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).

Minimization of ligand degradation products, or reversion of same to useful phosphine ligands

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,&#x3b2;-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).

Minimization of ligand degradation products, of reversion of same to useful phosphine ligands

An olefin metathesis process involving contacting an unsaturated fatty acid ester or unsaturated fatty acid, such as methyloleate or oleic acid, with a lower olefin, preferably ethylene, in the presence of a metathesis catalyst so as to prepare a first product olefin, preferably, a reduced chain &#x3b1;-olefin, such as methyl-9-decenoate or 9-decenoic acid, respectively. The metathesis catalyst contains ruthenium or osmium and a chelating ligand, preferably, a chelating ligand containing a carbene moiety and a second donor moiety of a Group 15 or 16 element Optionally, the catalyst can be supported on a catalyst support, such as, a cross-linked polymeric resin.

Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins

This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more polar solvents and one or more nonpolar solvents by phase separation wherein (i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.5, and (iii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more reaction byproducts is expressed by a partition coefficient ratio Ef,which is a value greater than about 2.5.

Separation processes

This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophoshorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a nonpolar solvent and a polar solvent by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5 (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.5, and (iii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more reaction byproducts is expressed by a partition coefficient ratio Ef3 which is a value greater than about 2.5.

Metal-ligand complex catalyzed processes

This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more products from a continuously generated reaction product fluid comprising one or more unreacted reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, one or more nonpolar solvents and one or more polar solvents by phase separation wherein (i) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1which is a value greater than about 2.5, (ii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.5, and (iii) the selectivity of the nonpolar phase for the organophosphorus ligand with respect to the one or more reaction byproducts is expressed by a partition coefficient ratio Ef3 which is a value greater than about 2.5.

This invention relates to a process for separating one or more organophosphorus ligand degradation products, one or more reaction byproducts and one or more formylester products from a reaction product fluid comprising one or more unreacted unsaturated ester reactants, a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more organophosphorus ligand degradation products, said one or more reaction byproducts, said one or more products, a polar solvent and a nonpolar solvent by phase separation wherein(i) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more products is expressed by a partition coefficient ratio Ef1 which is a value greater than about 2.5, (ii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more organophosphorus ligand degradation products is expressed by a partition coefficient ratio Ef2 which is a value greater than about 2.5, and (iii) the selectivity of the polar phase for the organophosphorus ligand with respect to the one or more reaction byproducts is expressed by a partition coefficient ratio Ef3 which is a value greater than about 2.5.

This invention relates to a method of stabilizing a metal-organophosphorus ligand complex catalyst against deactivation in a process which comprises reacting one or more reactants in the presence of a metal-organophosphorus ligand complex catalyst and optionally free organophosphorus ligand to produce a reaction product fluid comprising one or more products, and in which at least a portion of said process is conducted under separation conditions sufficient to effect at least some deactivation of the metal-organophosphorus ligand complex catalyst, which method comprises conducting the portion of said process that occurs under separation conditions in the presence of one or more alkadienes sufficient to prevent and/or lessen deactivation of the metal-organophosphorus ligand complex catalyst.

This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a nonpolar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a polar solvent to obtain by phase separation a non-polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said nonpolar solvent and a polar phase comprising said one or more products and polar solvent, and (2) recovering said polar phase from said nonpolar phase; wherein said organophosphorus ligand has a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 5, and said one or more products have a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 0.5.

This invention relates to a process for separating one or more products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, a polar solvent and said one or more products, wherein said process comprises (1) mixing said reaction product fluid with a nonpolar solvent to obtain by phase separation a polar phase comprising said metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand and said polar solvent and a nonpolar phase comprising said one or more products and nonpolar solvent, and (2) recovering said nonpolar phase from said polar phase; wherein said organophosphorus ligand has a partition coefficient between the polar solvent and the nonpolar solvent of greater than about 10, and said one or more products have a partition coefficient between the nonpolar solvent and the polar solvent of greater than about 0.5.

This invention relates to a process which comprises reacting one or more reactants in the presence of a metal-organophosphite ligand complex catalyst and dissolved water and optionally free organophosphite ligand to produce a reaction product fluid comprising one or more products, wherein said process is conducted in the presence of carbon dioxide in an amount sufficient not to effect substantial degradation of any said organophosphite ligand and/or substantial deactivation of said metal-organophosphite ligand complex catalyst.

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Hurricane, WV, United States of America

Donald Lee Morrison