Ruhrchemie Aktiengesellschaft

Hoechst Aktiengesellschaft

Ruhrechemie Aktiengesellschaft

Werner Konkol

Helmut Bahrmann

Boy Cornils

Hanswilhelm Bach

Ernst Wiebus

Wilhelm Gick

Wolfgang Lipps

Ernest Wiebus

Wolfgang Anton Herrmann

Jurgen Kulpe

Josef Hibbel

Bernhard Lieder

Ludger Bexten

Georg Dambkes

Heinz-Dieter Hahn

Jurgen Weber

Thomas Muller

Wolfgang Greb

Christian Kohlpaintner

Volkmar Schmidt

Gerhard Diekhaus

Heinz Kalbfell

Gunther Kessen

Joachim Much

Jugen Weber

Volker Heim

W A Herrmann

Gehard Diekhaus

A process for regenerating a water-soluble hydroformylation catalyst system comprising a coupler rhodium hydrogen-carbonyl complex of rhodium and compounds of the formula ##STR1## wherein Ar.sup.1 and Ar.sup.2 and Ar.sup.3 are individually phenyl or naphthyl, Y.sup.1, Y.sup.2 and Y.sup.3 are individually selected from the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms, halogen, --OH, --CN, --NO.sub.2 and R.sup.1 R.sup.2 N--, R.sup.1 and R.sup.2 are individually alkyl of 1 to 4 carbon atoms, X.sup.1, X.sup.2 and X.sup.3 are individually carboxylate (--COO.sup.-) or sulfonate (--SO.sub.3.sup.-), m.sub.1, m.sub.2 and m.sub.3 are individually integers of 0 to 3, at least one of m.sub.1, m.sub.2 or m.sub.3 being equal to or greater than 1, and n.sub.1, n.sub.2 and n.sub.3 are individually integers of 0 to 5 and if appropriate in excess comprising adding maleic acid, fumaric acid or olefinically unsaturated compounds of formula ##STR2## wherein X is selected from the group consisting of O, S, -- ##STR3## or ##STR4## and R.sup.3, R.sup.4 and R.sup.5 are individually hydrogen, or alkyl or aryl to an aqueous solution of the catalyst system in an amount sufficient to remove sulfonated or carboxylated alkyl-arylphosphanes.

Reactivation of water-soluble hydroformylation catalysts

A process for separating rhodium from mixtures thereof, comprising extracting said rhodium with an aqueous solution of a rhodium complexing agent and a solubilizer. A process for preparing aldehydes in the presence of both the complexing agent and the solubilizer is also set forth. The solubilizer is generally selected from salts of carboxylic acids having 8-20 carbon atoms, alkyl sulfonates, alkyl aryl sulfonates, amines and quaternary ammonium compounds of Formula II ##STR1## wherein A is alkyl, alkoxy, hydroxyalkyl, aryl having 6-25 carbon atoms, or R.sup.7 CONHCH.sub.2 CH.sub.2 CH.sub.2 --wherein R.sup.7 is alkyl having 5-11 carbon atoms; B is an alkyl having 1-25 carbon atoms, an aryl having 6-25 carbon atoms, or an .omega.-hydroxy alkyl having 1-4 carbon atoms; C and D are each independently an alkyl or .omega.-hydroxy alkyl having 1-4 carbon atoms or form, together with each other and the bridging N, a 5 or 6 membered heterocyclic ring; E is a halide, sulfate, borate, sulfonate, lactate or citrate; and p is the number of charges on E. The rhodium complexing agent is preferably a triaryl phosphine carboxylate or sulfonate.

Process for hydroformylation with rhodium catalysts and the separation

Bis{.mu.-hydroxy)bis[tris(sodium m-sulfonatophenyl)-phosphane]-rhodium(I)} dodecahydrate and methods of preparation thereof. The compounds are useful as catalysts for the hydroformylation reaction.

Complex compound of rhodium-containing sulfonated triphenylphosphane

Mixtures of substances containing metal complex compounds, organoelemental ligands, and/or other components are separated according to the invention by chromatography on stationary supports in an aqueous or aqueous/organic medium.

Process for separating mixtures of substances contained in an aqueous or

A process for the preparation of aldehydes including reacting olefins with carbon monoxide and hydrogen in an aqueous liquid phase in the presence of a rhodium catalyst and a specific class of water soluble aryl phosphines. These phosphines are preferably mixtures of alkali metal salts and quaternary ammonium salts of sulfonated aryl phosphines.

Process for the preparation of aldehydes

In a hydroformylation process for the preparation of aldehydes by reacting aliphatic olefins of 2 to 12 carbon atoms with carbon monoxide and hydrogen at temperatures of 20.degree. to 150.degree. C. and pressures of 0.1 to 20 mPa in the liquid phase and in the presence of an aqueous solution of a catalyst containing originally 50 to 800 wt. ppm of rhodium and 25 to 30 wt. % of complex-forming, sulfonated or carboxylated triarylphosphines, in each case based on the aqueous solution, the improvement comprising adding fresh phosphine solution to maintain the original phosphine concentration, until the total concentration of complex-forming phosphines and secondary and degradation products of the phosphines not capable of forming complexes amounts to about 35 to 45 wt. % based on the aqueous solution to selectively form n-aldehydes.

Hydroformylation process

A process for the preparation of aldehydes by hydroformylation of olefins in the presence of an aqueous solution containing rhodium as a catalyst. The aqueous solution preferably contains rhodium in a concentration of 450 to 800 weight-ppm and sulfonated or carboxylated triarylphosphines as complex ligands in a concentration of 25 to 30% by weight, both based on the aqueous solution.

In a hydroformylation process for the preparation of aldehydes by reacting aliphatic olefins of 2 to 12 carbon atoms with carbon monoxide and hydrogen at temperatures of 20.degree. to 150.degree. C. and pressures of 0.1 to 20 mPa in the liquid phase and in the presence of an aqueous solution containing 50 to 800 wt. ppm of rhodium and 25 to 30 wt. % of phosphines, in each case based on the aqueous solution as a catalyst system and in addition the transformation products of the phosphines, the improvement comprising draining off a portion of the aqueous solution of the catalyst system together with the reaction product and replacing the same by fresh aqueous solution of the catalyst system whereby the original catalyst selectivity for formation of n-aldehydes is maintained.

A process for the preparation of a rhodium catalyst comprising dissolving a carboxylic acid salt of rhodium in a solvent taken from the class consisting of aliphatic, cycloaliphatic, aromatic hydrocarbons and mixtures thereof. The carboxylic acid has 2 to 18 carbon atoms. This salt is reacted with carbon monoxide and hydrogen to form a rhodium hydridrocarbonyl which is reacted with an aqueous solution of a triaryl phosphine. The aqueous solution may be present during the initial reaction of the rhodium salt or may be added thereafter. A catalyst which is the product of the foregoing process is also disclosed, as is a method of producing aldehydes using the catalyst.

Rhodium catalysts and methods of preparation and use thereof

The present invention relates to a process for the preparation of aldehydes by the reaction of olefinic compounds with hydrogen and carbon monoxide in the presence of a catalyst system containing rhodium and aromatic phosphines. The aromatic phosphines are soluble in organic media and represent salts of sulfonated or carboxylated triarylphosphines which are insoluble in water. After hydroformylation, the reaction product is treated with a diluted aqueous solution of a base and the aqueous phase containing rhodium and aromatic phosphines is separated. Thus, thermal loading of the catalyst, for example by the redistillation of the reaction product, is avoided.

The present invention relates to a process for the preparation of nonadecanediols by the hydroformylation of oleyl alcohol. Rhodium and salts of sulfonated or carboxylated triarylphosphines, which are soluble in organic media and insoluble in water, are used as hydroformylation catalysts. The hydroformylation product is then treated with a diluted solution of a base dissolved in water, the aqueous phase separated and the hydroformylation product treated with hydrogen at elevated temperature in the presence of a hydrogenation catalyst.

Process for the preparation of nonadecanediols

A process for the purification of a gas containing one or more of hydrogen sulfide, hydrogen cyanide, and carbonyl sulfide as impurities comprising contacting the gas with at least one aliphatic aldehyde which is liquid under the purification conditions. The gas is inert to the aldehyde under such conditions. The process is useful in the purification of synthesis gas for use in reactions wherein sensitive catalysts are employed.

Process for purification of gases

A method for the production of aldehydes from olefins with CO/H.sub.2 in the presence of a water-soluble rhodium-containing catalyst system is described. The reaction proceeds at 0.1 to 10 MPa and 20 to 160.degree. C. Ultrasound acts on the reaction mixture, consisting of an aqueous catalyst, an olefin, synthesis gas and the end products.

Process for the production of aldehydes

A process for the hydroformylation of aldehydes comprising reacting aliphatic olefins with carbon monoxide and hydrogen in a liquid phase in the presence of water, a rhodium catalyst and a water soluble salt of a sulfonated or carboxylated triarylphosphine, the reaction taking place in the presence of an aqueous phase having a pH of about 5.5 to about 6.2.

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Werner Konkol