Union Carbide Chemicals & Plastics Technology Corporation

Dow Technology Investments LLC

Union Carbide Chemicals & Technology LLC

Ailene Gardner Phillips

David Robert Bryant

John Robert Briggs

Jeffrey Scott Kanel

Brian Michael Roesch

John Michael Maher

Diane Lee Packett

Max Min Lee

David James Schreck

Thomas Carl Eisenschmid

Kurt Damar Olson

Ravindra Tupe

Donald Lee Morrison

David James Miller

Liping L Zhang

Anil Sakharam Guram

Michael Leo Tulchinsky

Paul Foley

Hwaili Soo

Erik Bruce Tjaden

Balu Shivaji Uphade

Arun Basrur

Paul Victor Hinman

Sasanka Raha

Biju M Devassy

Elaine Susan Brigham

Eric Bruce Tjaden

Liping Zhang

Ravindra Radhakisan Tupe

Disclosed herein are methods of using scaled selectivities to assist in determining whether changes to the value of a target ethylene oxide production parameter&#x2014;such as ethylene oxide production rate&#x2014;used in the process of epoxidizing ethylene with a high-selectivity catalyst, have caused the process to move away from optimal operation. If the deviation from optimal operation has not worsened, it is generally unnecessary to perform a full optimization study even if the value of a target ethylene oxide production parameter has changed, which reduces or eliminates process disturbances caused by carrying out such studies. Methods are also disclosed which use both scaled selectivities and scaled reaction temperatures. If scaled selectivities reveal that a change in the value of a target ethylene oxide production parameter has moved the process away from optimal operation, scaled reaction temperatures can, under certain conditions, provide an indication of the directions in which the reaction temperature and/or overall catalyst chloriding effectiveness should be changed to move toward optimal operation. If a change in the value of a target ethylene oxide production parameter has improved the scaled selectivity, the scaled reaction temperature may also be used to guide further adjustments which may further improve scaled selectivity.

Process for manufacturing ethylene oxide using scaled selectivity values

Methods of reducing or maintaining the value of an alkylene oxide production parameter (such as alkylene oxide production rate) in a process of making an alkylene oxide by reacting an alkylene and oxygen over a high efficiency catalyst are shown and described. One method comprises reducing the concentration of oxygen in the reactor feed gas to reduce or maintain the value of the alkylene oxide production parameter.

Method of reducing or maintaining the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst

A process for conditioning a high efficiency silver catalyst used to manufacture ethylene oxide from ethylene, oxygen, and at least one organic chloride is described. A non-reactive conditioning gas comprising at least one of ethylene, oxygen, and a ballast gas is introduced to the catalyst at a conditioning temperature ranging from 150&#xb0; C. to 180&#xb0; C. for a selected period of at least 4 hours.

Process for conditioning a high efficiency ethylene oxide catalyst

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 products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, in which said reaction product fluid exhibits phase behavior depicted by FIG.,, wherein said process comprises (1) supplying said reaction product fluid from a reaction zone to a separation zone, (2) controlling concentration of said one or more nonpolar reaction solvents and said one or more polar reaction solvents, temperature and pressure in said separation zone sufficient to obtain by phase separation two immiscible liquid phases depicted by regions,and,of FIG.,comprising a polar phase and a nonpolar phase and to prevent or minimize formation of three immiscible liquid phases depicted by region,of FIG.,and one homogeneous liquid phase depicted by regions,and,of FIG.,, and (3) recovering said polar phase from said nonpolar phase or said nonpolar phase from said polar phase.

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 products from a reaction product fluid comprising a metal-organophosphorus ligand complex catalyst, optionally free organophosphorus ligand, said one or more products, one or more nonpolar reaction solvents and one or more polar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one nonpolar extraction solvent and at least one polar extraction solvent, to obtain a nonpolar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent and a polar phase comprising said one or more products, said one or more polar reaction solvents and said at least one polar extraction solvent, and (2) recovering said polar phase from said nonpolar phase; wherein (i) the organophosphorus ligand has a partition coefficient Kp1 defined herein between the nonpolar phase and the polar phase of greater than about 5, and (ii) the one or more products have a partition coefficient Kp2 defined herein between the nonpolar phase and the polar phase of less than about 2.0.

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, said one or more products, one or more polar reaction solvents and one or more nonpolar reaction solvents, wherein said process comprises (1) subjecting said reaction product fluid to fractional countercurrent extraction with at least two immiscible extraction solvents, said at least two immiscible extraction solvents comprising at least one polar extraction solvent and at least one nonpolar extraction solvent, to obtain a polar phase comprising said metal-organophosphorus ligand complex catalyst, said optionally free organophosphorus ligand, said one or more polar reaction solvents and said at least one polar extraction solvent and a nonpolar phase comprising said one or more products, said one or more nonpolar reaction solvents and said at least one nonpolar extraction solvent, and (2) recovering said nonpolar phase from said polar phase; wherein (i) the organophosphorus ligand has a partition coefficient Kp1 defined herein between the polar phase and the nonpolar phase of greater than about 5, and (ii) the one or more products have a partition coefficient Kp2 defined herein between the polar phase and the nonpolar phase of less than about 2.0.

This invention relates in part to processes for producing one or more substituted or unsubstituted 1,6-hexanediols which comprise subjecting one or more substituted or unsubstituted penten-1-ols to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.

Processes for producing 1,6-hexanediols

This invention relates in part to processes for selectively producing one or more substituted or unsubstituted 1,6-hexanedials, e.g., adipaldehyde, which comprise: (a) subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, or a mixture comprising one or more substituted or unsubstituted alkadienes to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and at an alkadiene partial pressure and/or a carbon monoxide partial pressure sufficient to selectively produce one or more substituted or unsubstituted pentenals or a reaction mixture comprising one or more substituted or unsubstituted pentenals; and (b) subjecting said one or more substituted or unsubstituted pentenals or said reaction mixture comprising one or more substituted or unsubstituted pentenals to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to selectively produce said one or more substituted or unsubstituted 1,6-hexanedials. The substituted or unsubstituted 1,6-hexanedials produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanedials as principal product(s) of reaction.

Processes for producing 1,6-hexanedials and derivatives

This invention relates in part to processes for selectively producing one or more substituted or unsubstituted alkenals. The process hydroformylates at least one substituted or unsubstituted alkadienes, e.g., butadiene, or a mixture of one or more substituted or unsubstituted alkadienes in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and at an alkadiene and/or carbon monoxide partial pressure sufficient to selectively produce at least one substituted or unsubstituted alkenals, e.g., pentenals. The substituted and unsubstituted alkenals produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., hydrogenation to alkenols, particularly pentenols. This invention also relates to reaction mixtures containing one or more substituted or unsubstituted alkenals or alkenols as principal product(s) of those reactions.

Processes for producing alkenals and alkenols

This invention relates in part to processes for producing one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanals, which comprise subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted hydroxyaldehydes. The substituted and unsubstituted hydroxyaldehydes produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted hydroxyaldehydes as principal product(s) of reaction.

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Charleston, WV, United States of America

Ailene Gardner Phillips