Rhone-Poulenc Chimie

Rhodia Fiber & Resin Intermediates

R. P. Fiber & Resin Intermediates

Rhone-Poulenc Fiber & Resin Intermediates

Rhodia Feber & Resin Intermedaites

Marc Huser

Robert M Perron

Paolo Burattin

Pierre Coqueret

John Osborn

Dominique Horbez

Alex Chamard

Sylvain Mutez

Larbi Aouni

Hydrocyanation catalysts comprising aqueous solutions of at least one water-soluble phosphine and nickel values, well suited for the hydrocyanation of ethylenically unsaturated organic compounds such as diolefins, olefinic nitrites and monolefins, are produced by (a) admixing an aqueous solution of such at least one water-soluble phosphine with a nickel hydroxide, (b) adding hydrogen cyanide or a compound which generates hydrogen cyanide to the mixture thus formed, (c) stirring the resulting mixture until the nickel values have at least partially dissolved, and (d) reducing at least a portion of said nickel values having an oxidation state of greater than zero to the zero oxidation state.

Production of hydrocyanation catalysts

Water-soluble sulfonated organophosphorus compounds are purified by at least partially removing contaminating sulfite values therefrom, by decreasing the pH of a solution of such sulfonated organophosphorus compounds to a value of less than or equal to 4, and maintaining the pH of the solution at this value of 4 or less for such period of time as to reduce the weight concentration of sulfite in the solution to less than 100 ppm; the organophosphorus compounds thus purified are well suited for the two-phase cocatalysis of a wide variety of organic reactions.

Purified sulfonated organophosphorus compounds and catalysis of organic reactions therewith

Ethylenically unsaturated organic compounds, for example diolefins, olefinic nitriles and monoolefins, are noncontaminatingly hydrocyanated into corresponding nitriles by (a) reacting such ethylenically unsaturated organic compounds with hydrogen cyanide in the presence of an aqueous solution containing a catalytically effective amount of a catalyst which comprises at least one nickel compound and at least one water-soluble phosphine, (b) thereafter separating the organic phase from the aqueous phase which result, the separated aqueous phase comprising a solid phase formed during hydrocyanation, and (c) thence treating the separated aqueous phase, or a solid phase removed therefrom, with hydrogen cyanide to thus at least partially dissolve said solid phase contained therein or removed therefrom.

Production of nitriles via hydrocyanation of ethylenically unsaturated organic compounds

Transition metal (0) or (1)/phosphine catalysts suited, e.g., for the hydrocyanation of ethylenically unsaturated compounds, are produced by reducing, via hydrogenation, aqueous solutions containing at least one transition metal compound and at least one monodentate or bidentate water-soluble phosphine, advantageously at least one phosphine having one of the following formulae (I) and/or (II):

Preparation of transition metal/phosphine catalysts by hydrogen reduction

Catalyst compounds comprising at least one transition metal in an oxidation state of 0 to 1, and at least one monodentate or bidentate water-soluble phosphine, well suited for the hydrocyanation of ethylenically unsaturated compounds, are electrochemically synthesized, by electrolyzing an aqueous solution catholyte (contained in the cathode compartment of any suitable electrolytic cell) comprising at least one transition metal compound and at least one monodentate or bidentate water-soluble phosphine, advantageously at least one phosphine having the following formulae (I) and/or (II):

Electrochemical synthesis of transition metal/phosphine catalysts

The present invention relates to a process for the hydrocyanation of organic compounds containing ethylenic unsaturation to nitrites, in particular the hydrocyanation of diolefins or of substituted olefins, such as alkenenitriles. More specifically, it comprises a process for the hydrocyanation of organic compounds containing at least one ethylenic double bond by reaction with hydrogen cyanide in the presence of an aqueous solution of a catalyst comprising at least one transition metal compound and at least one water-soluble phosphine, characterized in that the said water-soluble phosphine is a monodentate or bidentate phosphine.

Process for the hydrocyanation of organic compounds containing ethylenic

Catalyst compounds comprising at least one transition metal having an oxidation number of 0 or 1 and at least one sulfonated phosphine are electrochemically synthesized, by electrolyzing an aqueous solution catholyte (contained in the cathode compartment of any suitable electrolytic cell) comprising at least one transition metal compound and at least one sulfonated phosphine.

Electrochemical synthesis of transition metal/phosphine catalyst

Ethylenically unsaturated aliphatic nitriles, for example the linear pentenenitriles, are converted/hydrocyanated into their corresponding dinitriles, for example adiponitrile, by reacting such nitriles with hydrogen cyanide, in an aqueous reaction medium which comprises (1) a catalytically effective amount of a transition metal compound and a sulfonated phosphine, together with (2) a cocatalytically effective amount of at least one Lewis acid; the Lewis acid cocatalyst promotes the linearity of the final product dinitriles and/or prolongs the useful life of the catalyst.

Hydrocyanation of olefinically unsaturated nitriles into dinitrile

2-Methyl-3-butenenitrile is efficiently and readily converted into a linear pentenenitrile, notably 3-pentenenitrile, a valuable intermediate for the production of adiponitrile, by isomerizing same in the presence of a catalytically effective amount of an aqueous solution of at least one sulfonated phosphine and at least one transition metal compound.

Isomerization of 2-methyl-3-butenenitrile

Difunctional butenes are linearly dicarbonylated into 3-hexene-1,6-dioic acid or alkyl diesters thereof, well suited for the ultimate production of, e.g., adipic acid, by reacting such difunctional butene with carbon monoxide and, if appropriate, an alcohol, at an elevated temperature under superatmospheric pressure, in the presence of at least one source of hydrogen chloride and a catalytically effective amount of palladium, at least a portion of which palladium being in the zero oxidation state, as well as a quaternary onium chloride of nitrogen or phosphorus, the nitrogen or phosphorus atom being tetracoordinated to carbon atoms, with the proviso that the nitrogen atom may be coordinated to two pentavalent phosphorus atoms.

Linear dicarbonylation of difunctionalized butenes

A process of alkoxycarbonylation making use of a new catalyst consisting of a palladium-phosphine complex, the phosphine having a pKa greater than or equal to 7, a chlorinated aromatic compound, carbon monoxide and an alcohol.

Alkoxycarbonylation process

A process of hydrogenolysis utilizing a new catalyst consisting of a palladium phosphine complex, the phosphien having a pKa greater than or equal to 6, a chlorinated aromatic compound and hydrogen.

Hydrogenolysis process

New palladium-based complexes permit the complexing of chlorinated aromatic derivatives. These complexes make it possible to perform hydrogenolysis, hydrocarbonylation and alkoxycarbonylation reaction on chlorinated compounds.

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Villeurbanne, France

Marc Huser