Dow Technology Investments LLC

Dow Global Technolgoies LLC

Basf Se Corporation

Michael A Brammer

Glenn A Miller

Thomas Carl Eisenschmid

Marinus A Bigi

Rick B Watson

George R Phillips

Michael C Becker

Jeffrey Scott Sawrey

Wanglin Yu

Jens Rudolph

Martin Smidt

Irvin B Cox

Amarnath Singh

Sung-Yu Ku

Avery L Watkins

Edward Adrian Lord

Jason F Giles

Donald L Campbell, Jr

Hans-Rüdiger Reeh

William N Felsted, Ii

Thomas C Eisenschmid

Hans-Rudiger Reeh

Stephen W King

John Michael Maher

Richard W Wegman

Heather Spinney

Wei-Jun Peng

Morteza Mokhtarzadeh

Huifeng Qian

Cloid Russell Smith, Iii

Christopher S Letko

Adrian Lord

Kenneth L Kearns, Jr

Hans-Günter Thelen

Donald L Campbell

Britt A Vanchura, Ii

Sally Demaio-Turner

Hugo Tricas

Robert David John Froese

Pertrus W N M Van Leeuwen

Olivier Diebolt

Michael John Bainbridge

Robert Hetterley

Stephane Wambergue

Maximilian Walter

Jeffrey S Sawrey

Donald L Campbell Jr

William N Felsted Ii

Jr Campbell Donald L

Martin Lucas Smidt

Hans-Gunter Thelen

The present disclosure provides a process. In an embodiment, the process includes providing a first blend composed of nonanals, Colefins and C-Calkanes. The process includes adding, to the first blend, a component selected from Caldehyde, Caldehyde, and combinations thereof to form a non-aqueous reaction mixture having an initial water content from 0 wt % to 10 wt % water. The process includes introducing an organic base catalyst to the non-aqueous reaction mixture and heating the non-aqueous reaction mixture to a temperature from 30° C. to 100° C. and cross-aldol condensing the non-aqueous reaction mixture. The process includes forming a cross-aldol product composed of a component selected from Cenals, Cenals, Cenals, Cenals, and Cenals, and combinations thereof.

Organic catalyst for non-aqueous aldol condensation

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 catalyst compositions for hydroformylation processes and to hydroformylation processes utilizing certain catalysts. In one aspect, a catalyst composition for a hydroformylation process comprises (a) a transition metal; (b) a monophosphine; and (c) a tetraphosphine having the structure described herein, and wherein the composition comprises at least 40 moles of monophosphine per mole of transition metal.

Catalyst compositions and hydroformylation processes

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

The present invention relates to methods of controlling hydroformylation processes for producing normal (N) and iso (I) aldehydes at a N:I ratio. In one aspect, a method of controlling a hydroformylation process comprises contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of increasing the N:I ratio by adding additional tetraphosphine to a reaction zone; decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or increasing the N:I ratio by volatilization of the free monophosphine.

Methods of controlling hydroformylation processes

Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products. In some embodiments, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.

Methods to rejuvenate a deactivated hydroformylation catalyst solution

A mixture of octanols, nonanols and decanols is useful for the preparation of alkoxylates, which alkoxylates may be used as surfactants, which surfactants have surprisingly good biodegradability.

Readily biodegradable alkoxylate mixtures

Disclosed herein are methods of treating a hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products and wherein the hydroformylation catalyst solution is used to hydroformylate an olefin in an operating hydroformylation unit. In some embodiments, such methods comprise contacting the catalyst solution with a peroxide in the operating hydroformylation unit.

Methods of treating a hydroformylation catalyst solution

The present invention relates to methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in a hydroformylation process. In one aspect, a method comprises (a) contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a tetraphosphine having the structure described herein, and, optionally, (C) a monophosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions; and (b) adding additional monophosphine having the structure described herein to a reaction zone.

Methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in hydroformylation processes

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

The present invention relates to hydroformylation processes for producing aldehydes. In some embodiments, the process comprises contacting in a reaction zone reactants comprising an olefin, hydrogen and CO in the presence of a rhodium-organophosphite based catalyst, optionally with free organophosphite ligand, and 0.1 to 3 weight percent, based on the total weight of the fluid in the reaction zone, of certain polymers specified herein, such that the solubility of the polymer in the aldehyde is greater than or equal to 1 weight percent at 40&#xb0; C.

Some embodiments of the present invention relate to processes for reducing heavies formation in a solution comprising one or more aldehydes, such as a reaction fluid in a hydroformylation process. In some embodiments, the process comprises providing 0.1 to 5 wt. percent of an organic nitrogen compound based on the total weight of the aldehyde solution, the organic nitrogen compound comprising: wherein each of R1-R5 are independently hydrogen, an alkyl, or an aryl radical. 

Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polydentate phosphine ligands, and polydentate phosphine ligand degradation products. In one embodiment, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.

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

Growing community of inventors

Freeport, TX, United States of America

Michael A Brammer