E.i. Dupont De Nemours and Company

Dsm N.v.

E. I. Du Pont De Nemours

Dsm Desotech, Inc.

Patrick M Burke

Wilson Tam

James Michael Garner

Henk Oevering

Norman Herron

Leo Ernest Manzer

Francis Joseph Waller

Kenneth Gene Moloy

Kristina Ann Kreutzer

Joe Douglas Druliner

Emilio Enrique Bunel

Antonius J Teunissen

Imre Toth

Onko Jan Gelling

James B Sieja

Carina S Snijder

Carolina B Hansen

Manxue Wang

Stephan James McLain

Otto E Sielcken

Anne Irisa Breikss

The invention relates to a process for the making organic aldehyde compounds from an unsaturated compound by hydroformylation and in the presence of a catalyst system comprising a Group VIII metal and a bidentate phosphorus ligand having two trivalent phosphorus atoms bound to salicylanilide groups.

Process for preparing aldehyde compounds

Supported bis(phosphorus) ligands are disclosed for use in hydroformylation reactions, including the hydroformylation of olefins. Catalysts are formed when the ligands are complexed with a catalytically active metal (e.g., rhodium or iridium).

Hydroformylation of olefins using supported bis(phosphorus) ligands

Process for the preparation of an alkyl pentenoate respectively an aryl pentenoate by contacting an alkoxy-butene respectively an aryloxy-butene compound with carbon monoxide in the presence of a catalyst system comprising palladium, a phosphorus ligand and an acid promotor, wherein the molar ratio of 3-alkoxy-1-butene to 1-alkoxy-2-butene, respectively the molar ratio of 3-aryloxy-1-butene to 1-aryloxy-2-butene, is higher than 4.

Process to prepare a pentenoic acid derivative

A process for the carbonylation of allylic butenol or butenyl ester of a carboxylic acid (e.g., crotyl acetate, 3-acetoxybutene-1 and mixtures thereof) in an anhydrous carboxylic acid solvent and production of beta-gamma unsaturated carboxylic acid anhydride (e.g., 3-pentenoic acid anhydride) utilizing a rhodium-containing catalyst (e.g., dicarbonylacetylacetonate rhodium(I)) promoted with a metal iodide (e.g., dicarbonylacetylacetonate rhodium(I), or the like). The following representative reaction showing a crotyl ester (i.e., a carboxylic acid ester of 2-buten-1-ol) as the reactant producing a corresponding pentenoic acid anhydride is illustrative of the overall carbonylation. ##STR1## Suitable allylic compounds are of the form ##STR2## where one of the groups R.sup.1, R.sup.2, and R.sup.3 is methyl and the other two groups are H and wherein R.sub.4 is selected from the group consisting of H and ##STR3## wherein R.sup.5 is selected from the group consisting of a C.sub.1 to C.sub.10 alkyl. Such a process is particularly useful in the production of beta-gamma unsaturated carboxylic acid anhydride without promoting the back reaction producing butadiene and a carboxylic acid.

Rhodium catalyzed carbonylation of an allylic butenol or butenyl ester

Process to prepare a pentenoic acid anhydride in the pressence of a catalyst comprising palladium and an organic phosphine ligand, wherein the corresponding alkoxycarbonyl butene is reacted with carbon monoxide at a temperature between 50 and 130.degree. C. and that the phosphine is a monodentate phosphine or a bidentate phosphine.

Process to prepare a pentenoic acid anhydride

A hydroformylation process for preparating a terminal aldehyde involves reacting an ethylenically unsaturated organic compound with carbon monoxide and hydrogen in the presence of a catalyst system iridium or rhodium and a bidentate organic phosphite ligand wherein the two phosphorus atoms of the phopshite ligand are linked with a 2,2'-dihydroxyl-1,1'-binapthalene bridging group having the following structure (Q): ##STR1## in which R.sup.1 and R.sup.2 are substituents other than hydrogen and in which R.sup.3 and R.sup.4 are the same or different substituted monovalent aryl groups and/or any one of OR.sup.3 and OR.sup.4 connected to one phosphorus atom forms an --O--R.sup.5 --O-group, where R.sup.5 is a divalent organic group containing one or two aryl groups.

Process to prepare a terminal aldehyde

Process for making 3-pentenoic acid acid by reacting an allylic butenyl alcohol or its corresponding ester with carbon monoxide in the presence of nickel, and a source of iodide. ##STR1##

Process for the preparation of 3-pentenoic acid from allylic butenyl

Process for making 3-pentenoic acid by reacting butadiene with carbon monoxide in the presence of nickel and an iodide source.

Process for the preparation of 3-pentenoic acid from butadiene using a

A hydroformylation catalyst composition comprising iridium or rhodium and a bidentate organic phosphite ligand wherein the two phosphorus atoms of the phopshite ligand are linked with a 2,2'-dihydroxyl-1,1'-binapthalene bridging group having the following structure (Q): ##STR1## in which R.sup.1 and R.sup.2 are substituents other than hydrogen.

The invention relates to a process for the preparation of linear aldehydes by hydroformylation of ethylenically unsaturated organic compounds in the presence of a catalyst system comprising a Group VIII metal and a bidentate organic ligand. The bidentate organic ligand is characterized in that it has two trivalent phosphorus atoms each containing at least one P--C or one P--N bond.

Process to prepare a linear aldehyde

A hydroformylation process for the production of linear aldehydes of an olefin, with hydrogen and carbon monoxide in a solvent containing a catalyst having a platinum component, a bidentate diaryl phosphine component where the bridging group is ferrocenyl, and an acid promoter component.

Hydroformylation process

A hydroformylation process for the production of 5-formylvaleric acid from 2-, or 3-pentenoic acid, or 5-formylvaleric acid ester from 2-, or 3-pentenoic acid ester, or 5-formylvaleronitrile from 2-, or 3-pentenenitrile by reaction with hydrogen and carbon monoxide in a solvent containing a catalyst having a platinum component, a bidentate diaryl phosphine component, an acid promoter component.

A hydroformylation process for the production of linear aldehydes from linear olefins, by the reaction of the olefin with hydrogen and carbon monoxide in a solvent containing a catalyst having a platinum component or palladium component, a bidentate diaryl phosphine component where the bridging group is ferrocenyl or 3 to 6 carbon atoms, and a metal promoter component.

An improved process for the isomerization of saturated alkyl carboxylic acids is obtained by using aluminum iodide or aluminum bromide promoted rhodium or iridium catalysts.

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Wilmington, DE, United States of America

Patrick M Burke