Dow Technology Investments LLC

Osi Specialties, Inc.

Basf Se Corporation

Dow Global Technolgoies LLC

Union Carbide Chemicals & Plastics Technology Corporation

Union Carbide Chemical and Plastics Technology Technology

Crompton Gmbh

Glenn A Miller

Michael A Brammer

Thomas Carl Eisenschmid

Ernst Billig

Marinus A Bigi

George R Phillips

Michael C Becker

Rick B Watson

Jeffrey Scott Sawrey

Irvin B Cox

Martin Smidt

Jason F Giles

Jens Rudolph

Amarnath Singh

Morteza Mokhtarzadeh

Michael W Jorgenson

Donald L Campbell

Edward Adrian Lord

Donald L Campbell, Jr

Hans-Rüdiger Reeh

Richard Budnik

Victoria L Biedenstein

Anthony G Abatjoglou

Richard M Gerkin

Christopher W Derstine

Ronald R Peterson

Cloid Russell Smith, Iii

Mark E Harakal

Adrian Lord

Gretchen Baier

David Welch

Kenneth L Kearns, Jr

Susan B McVey

Hans-Günter Thelen

Rainer Potthast

Atul Manilal Shah

Britt A Vanchura, Ii

James D Duston

Stephane Wambergue

Steven H Fisher

Maximilian Walter

Edward H Yonemoto

Anthony G Abatjoglon

Shankhadeep Das

Seshadri Kumar

Lee F Lawler

David L Kirchner

Nilesh Parmar

Pramod Dalvi

Ravindrakumar N Raval

Martin Lucas Smidt

Hans-Rudiger Reeh

Donald L Campbell Jr

The present invention generally relates to processes for the recovery of rhodium from a catalyst purge stream from a C6 or higher olefin hydroformylation process. In one embodiment, the process comprises (a) treating a catalyst-containing liquid purge stream from the hydroformylation process, wherein the catalyst comprises a precious metal and an organophosphorous ligand, with an oxidant in the presence of a separate liquid aqueous phase comprising a halide-free acid at a sufficient temperature to effect oxidation of a majority of the contained organophosphorous ligand, wherein the halide-free acid is a C1-C6 organic acid or phosphorous acid; (b) recovering the aqueous phase; (c) contacting the aqueous phase with a separate organic phase by mixing the two phases under a syngas atmosphere, wherein the separate organic phase comprises water-insoluble, hydrolysable organophosphorous ligand and recycled olefin from a hydroformylation process; and (d) separating the organic phase to be recycled back to a hydroformylation process.

Processes for recovery of rhodium from a hydroformylation process

The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms. In one aspect, a process comprises (a) hydroformylating a mixed C4 olefin stream, wherein the mixed C4 olefin stream comprises 1-butene, 2-butene, and optionally isobutene, with a hydroformylation catalyst, wherein the hydroformylation catalyst comprises rhodium with monodentate organophosphorous ligand and optionally polydentate organophosphorous ligand, to produce a mixture comprising linear and branched C5 aldehydes; (b) separating the branched C5 aldehydes from the linear C5 aldehydes to provide a branched C5 aldehyde stream and a linear C5 aldehyde stream; (c) dehydrating the branched C5 aldehydes in the branched C5 aldehyde stream using a dehydration catalyst to form a stream comprising isoprene; (d) hydrogenating the linear C5 aldehydes in the linear C5 aldehyde stream to form a C5 alcohol stream; (e) dehydrating the C5 alcohols in the C5 alcohol stream with a second dehydration catalyst to form a C5 olefin stream; (f) hydroformylating the C5 olefins in the C5 olefin stream to generate a C6 aldehyde stream; (g) hydrogenating the C6 aldehydes in the C6 aldehyde stream to form a C6 alcohol stream; and (h) dehydrating the C6 alcohols in the C6 alcohol stream with a third dehydration catalyst to form a C6 olefin stream.

Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms

Embodiments of the present invention are directed to processes to improve rhodium accountability in continuous liquid recycle hydroformylation processes. In some embodiments, a process comprises contacting in a reaction zone reactants comprising mixed C8 olefins or mixed C9 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the reaction fluid is introduced to a strip gas vaporizer to produce a product stream and a vaporizer tails stream, and wherein the vaporizer tails stream comprises at least 1.2 percent by weight C8 internal olefins or at least 1.3 percent by weight C9 internal olefins.

Hydroformylation process

Embodiments of the present invention are directed to processes for purifying ligands such as organopolyphosphite ligands. In one embodiment, a process comprises: (a) receiving a solid organopolyphosphite compound that has been recrystallized or triturated at least once, wherein the solid organopolyphosphite compound comprises greater than one weight percent of an oxidized phosphite impurity and wherein the organopolyphosphite compound is substantially free of solvent; (b) slurrying the solid organopolyphosphite compound in a Cor higher alcohol at a temperature of at least 60&#xb0; C. for at least 20 minutes to reduce the oxidized phosphite impurity in the solid phase; and (c) removing liquid comprising dissolved oxidized phosphite impurity from the slurry, wherein the residual oxidized phosphite impurity content of the organopolyphosphite compound following step (c) is 1 weight percent or less.

Processes for purifying ligands

In one aspect, a hydroformylation reaction process comprises contacting an olefin, hydrogen, and CO in the presence of a homogeneous catalyst in a cylindrical reactor to provide a reaction fluid, wherein the reactor has a fixed height, and wherein a total mixing energy of at least 0.5 kW/m3 is delivered to the fluid in the reactor; removing a portion of the reaction fluid from the reactor; and returning at least a portion of the removed reaction fluid to the reactor, wherein the returning reaction fluid is introduced in at least two return locations positioned at a height that is less than 80% of the fixed height, wherein the at least two return locations are positioned above a location in the reactor where hydrogen and carbon monoxide are introduced to the reactor, and wherein at least 15% of the mixing energy is provided by the returning reaction fluid.

Hydroformylation reaction process

The present invention relate to processes for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive. In one embodiment, the process comprises (a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream; (b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates; (c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and (d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof is suitable for use as a gasoline additive.

Process for converting olefins to alcohols, ethers, or combinations thereof

A hydroformylation process wherein the hydrolyzable organophosphorous ligand component of the catalyst is supplied as a stabilized ligand composition comprising a hydrolyzable organophosphorous ligand and, per 100 moles compound, from 0.05 to 13 acid-neutralizing equivalents of an acid scavenger.

Stabilized organophosphorous compounds

A process involving admixing a ligand and an alkanolamine. The process allows the use of ligand despite the presence of contaminating amounts of phosphorus acid, and improves the shelf life of premixed ligand solutions.

Method for the preparation of a stabilized organophosphorous compound solution

The catalyst solution used in a hydroformylation process is prepared for storage by first reducing its acid concentration and/or water content, and then storing the solution under a blanket of syngas and/or an inert gas. Alternatively, or in addition to, the catalyst solution can be stored with an aqueous buffer comprising materials that will neutralize and/or absorb the acid species within the catalyst solution.

Methods to store transition metal organophosphorous ligand based catalysts

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in a an aromatic hydrocarbon solvent in the absence of water and free amine, wherein the hydrocarbon solvent comprises an aromatic hydrocarbon, a saturated aliphatic hydrocarbon, or a mixture thereof; and (c) removing undissolved phosphorous acid from the solution, wherein the acid content of the organophosphite following step (c) is 30 ppm or less.

Processes for producing organophosphorous compounds

The present invention relates to processes for producing organophosporous compositions having low acid content as well as processes for reprocessing partially degraded organophosporous compositions that contain high levels of phosphorous acid. In one embodiment, a process comprises: (a) receiving a solid organophosphite compound that has been recrystallized or triturated, wherein the solid organophosphite compound comprises phosphorous acid; (b) dissolving the solid organophosphite compound in an organic solvent; (c) treating the solution with a weakly basic adsorbent; and (d) collecting the treated organophosphite solution, wherein the acid content of the organophosphite following step (d) is 30 ppm or less.

Residual wash solvent, e.g., ethyl acetate, is removed from polyphosphite, e.g., bisphosphite, crystals by a process comprising the steps of: A. Mixing the polyphosphite crystals and residual wash solvent with a secondary alcohol, e.g., isopropyl alcohol (IPA), to form a mixture of polyphosphite crystals, residual wash solvent and secondary alcohol, and B. Drying the mixture to remove the residual wash solvent and secondary alcohol to a content of less than 0.5 wt % based on the weight of the polyphosphite crystals.

Preventing solvent of crystallization in production of polyphosphite ligands

A hydroformylation process wherein a water-soluble amine is contacted with the reaction fluid, liquid from the reactor is sent to an extraction zone, and a neutralized phosphorus acidic compound is at least partially removed from the extraction zone.

A ligand crystal structure of 6,6'-[[3,3&#x2032;,5,5&#x2032;-tetrakis(1,1-dimethylethyl)-[1,1&#x2032;-biphenyl]-2,2&#x2032;-diyl]bis(oxy)]bisdibenzo[d,f][1,3,2]-dioxaphosphepin. Formule (I) 

Crystalline ligand

The present invention relates generally to hydroformylation processes. In one embodiment, a process of the present invention comprises: (a) contacting CO, H, and at least one olefin under hydroformylation conditions sufficient to form at least one aldehyde product in the presence of a hydroformylation catalyst; (b) removing a product-containing liquid from the reaction zone and sending it to a vaporizer, which comprises a vaporizing zone and a vapor/liquid separation zone, wherein the product-containing liquid, which comprises crude product and catalyst, is heated in the vaporizing zone to form a mixture of gas and catalyst-containing liquid, which mixture is then phase separated in the separation zone, which separation zone has a liquid withdrawal port, a liquid region, a vapor space and a gas-liquid interface, wherein the liquid region comprises at least one divider plate, which optionally contains at least one perforation, wherein at least a portion of at least one divider plate is in proximity to the gas-liquid interface, with the proviso that at least a portion of at least one divider plate is at or below the interface, and wherein the temperature of the catalyst-containing liquid, measured at the liquid withdrawal port, is lower than the temperature of the vapor space.

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South Charleston, WV, United States of America

Glenn A Miller