Ruhrchemie Aktiengesellschaft

M.a.n. Maschinenfabrik Augsburg-Nurnberg A.g.

Hoechst Aktiengesellschaft

Bayer Aktiengesellschaft

Clariant Corporation

Maschinenfabrik Augsburg-Nurnberg Aktiengesellschaft

Ruhrchemie Aktiengesekkschaft

Boy Cornils

Helmut Bahrmann

Werner Konkol

Ernst Wiebus

Hanswilhelm Bach

Jurgen Weber

Hans Tummes

Wilhelm Gick

Wolfgang Lipps

Helmut Springer

Wolfgang Payer

Ludger Bexten

Josef Hibbel

Hans Feichtinger

Gerhard Diekhaus

Jurgen Falbe

Bela Tihanyi

Werner DeWin

Peter Lappe

August Muhlratzer

Edwin Erben

Carl D Frohning

Heinz Noeske

Ernest Wiebus

Roderich Gartner

Bernhard Lieder

Carl-Dieter Frohning

Heinz-Dieter Hahn

Dieter Kupies

Peter Schneller

Gunther Kessen

Waldemar Kascha

Friedrich Schnur

Steffen Haber

Wolfgang Greb

John V Hobes

Volkmar Schmidt

Wolfgang Zgorzelski

Hans-Walter Birnkraut

Wolfgang Bernhagen

Andreas Dierdorf

Georg Dambkes

Heinz Kalbfell

Siegfried Lutze

Mufit Bahadir

Winfried Materne

Werner De Win

Josef Meis

Joachim Much

Bernd Bussemeier

Norbert Breitkopf

Joseph Hibbel

Walter Rottig

Ingrid Forster

Herbert Gutwein

Roland Bertinger

Volker Heim

Gehard Diekhaus

Herbert Gothel

Willi Nollen

Hans-Dieter Hahn

Guunter Hetkamp

Karl Otterbein, Deceased

Karl Otterbein

Dieter Ernst

Hans-Joachim Tomuschat

Bern-Hard Lieder

Nitro compound-reducing process

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

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 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

The invention relates to new quaternary ammonium salts of di and trisulfonated triarylphosphines as well as a process for their preparation. The salts are of Formula I ##STR1## wherein Ar.sub.1, Ar.sub.2, and Ar.sub.3 are each independently an aryl; X.sup.1, X.sup.2, and X.sup.3 are each independently a sulfogroup; y.sup.1, y.sup.2, and y.sup.3 are each independently 0 or 1, provided that their sum is at least 1; A is an alkyl, hydroxyalkyl, aralkyl, or aryl having 6-25 carbon atoms; B, C, and D are straight chain or branched alkyl having 1-4 carbons; and n is a whole number of 1-3.

Quaternary ammonium salts of sulfonated triarylphosphines and process

A process for the production of 2-ethyl-hexanol comprising reacting propene with carbon monoxide and hydrogen, in the presence of an aqueous catalyst containing rhodium and at least one sulfonated triarylphosphine, to form an aqueous phase and an organic phase, said organic phase comprising a mixture of materials having boiling points lower than that of n-butanal and substances having boiling points equal to or higher than that of n-butanal, said materials including i-butanal, separating said material from said substances, subjecting said substances to aldol condensation, in the presence of aqueous alkali, to form 2-ethyl hexenal, first hydrogenating said 2-ethyl-hexenal in a gas phase in the presence of a first hydrogenation catalyst and thereafter hydrogenating said 2-ethyl-hexenal in a liquid phase to form 2-ethyl-hexanol in the presence of a second hydrogenation catalyst.

Process for the production of 2-ethyl-hexanol

The invention relates to new quaternary ammonium salts of di and trisulfonated triarylphosphines as well as a process for their preparation. The salts are of Formula I ##STR1## wherein Ar.sub.1, Ar.sub.2, and Ar.sub.3 are each independently an aryl; X.sup.1, X.sup.2, and X.sup.3 are each independently a sulfo group; y.sup.1, y.sup.2, and y.sup.3 are each independently 0 or 1, provided that their sum is at least 1; A is an alkyl, hydroxyalkyl, aralkyl, or aryl having 6-25 carbon atoms; B, C, and D are straight chain or branched alkyl having 1-4 carbons; and n is a whole number of 1-3.

A process for the purification of salts of at least one member of the group consisting of diphenylphosphine-phenyl-m-sulfonic acid, phenylphosphine-di-(m-phenylsulfonic acid) and triphenylphosphine-tri-(m-sulfonic acid) from aqueous solutions thereof comprising adding at least a molar equivalent amount of at least one member of the group consisting of di-(n-pentyl)-amine, di-(n-hexyl)-amine and water-soluble salts of said amines to an aqueous solution containing at least one member of the group consisting diphenylphosphine-phenyl-m-sulfonic acid, phenylphosphine-di-(m-phenylsulfonic acid), triphenylphosphine-tri(m-sulfonic acid) and salts thereof to adjust the pH value to .ltoreq.7, recovering the precipitate, washing the precipitate and dissolving the same in an aqueous basic solution.

Process for the purification of sulfonated aryl phosphines

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.

Process for preparing aldehydes

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Boy Cornils