Monsanto Company

Solutia Incorporated

Bp Chemicals Limited

Frank E Paulik

Arnold Hershman

James F Roth

Walter R Knox

Robert G Schultz

Thomas C Singleton

David J Weinkauff

John H Craddock

Carol R Weiss

An improved hydrolysis process comprising a process for the preparation of 2-carboxyalkyl(aryl)phosphinic acid using a controlled addition of water to an acrylation reaction mixture, and control of the temperature. Preparation of 2-carboxyalkyl(aryl)phosphinic acid cyclic anhydride is disclosed using a controlled addition of water, wherein up to about one mole of water per mole of dichloro(aryl)-phosphine charged to the acrylation reaction is added, and temperature is controlled.

Process for the preparation of 2-carboxyalkyl(aryl)phosphinic acid and corresponding anhydride(s)

Processes for producing 2-carboxyalkyl(phenyl)phosphinic acid comprising hydrolyzing the reaction mixture produced from the reaction of dichloro(phenyl)phosphine with a carboxylic acid in the presence of water, wherein the hydrolysis is conducted with reduced levels of water.

Production of 2-carboxyalkyl (phenyl)phosphinic acid

Certain (1,3,2-dioxaphosphorinanemethan) amine compounds, which are useful as flame retardant compounds, are disclosed. The compounds are particularly useful in polyurethane compositions.

Cyclic phosphorus containing flame retardant compounds

Certain (1,3,2-dioxaphosohorinanemethan) amine compounds, which are useful as halogen-free flame retardant compounds, are disclosed. The compounds are particularly useful in polyurethane compositions.

Halogen-free cyclic phosphorus-containing flame retardant compounds

Alkylidene diesters such as ethylidene diacetate are produced by reacting an ether and/or an ester under substantially anhydrous conditions with carbon monoxide and hydrogen in contact with a catalyst system comprising a rhodium compound and a halogen component at a temperature in the range from 125.degree. to 300.degree. C. and at a carbon monoxide partial pressure in the range from about 1.0 to 1100 kg/cm.sup.2. When ethylidene diacetate is the product, it can then be decomposed to produce vinyl acetate and acetic acid by well-known techniques. Since one mole of acetic acid is also produced in the synthesis of the diacetate, the invention makes possible an overall process for the production of vinyl acetate which produces acetic acid rather than consumes it.

Preparation of alkylidene diesters

This invention involves a process for the carbonylation of a carbonylatable reactant, e.g., an alkyl ester, a dialkyl ether or mixtures thereof by reacting the same with carbon monoxide. The process comprises effecting the carbonylation in the presence of a solution of a catalyst system containing a rhodium compound, an iodide and a lithium component at a temperature of from 50.degree. C. to 400.degree. C. at a carbon monoxide partial pressure of 1 psig to 15,000 psig. Hydrogen may also be present. The invention also concerns a carbonylation catalyst system effective for the addition of carbon monoxide to a carbonylatable reactant which comprises a solution containing as essential components a rhodium containing active component, an iodide and a lithium component.

Carbonylation process and catalyst

Alkylidene diesters such as ethylidene diacetate are selectively produced in high yields by reacting an ether and/or an ester under substantially anhydrous conditions with carbon monoxide and hydrogen in contact with a catalyst system comprising a rhodium compound, a halogen component, a palladium cocatalyst and a promoter component which is an agent for liberation of carboxylic acid anions. The process is carried out in the liquid phase in a solvent comprising a carboxylic acid at a temperature in the range of 150.degree. to 190.degree. C. and at a carbon monoxide partial pressure in the range from about 1.0 to 1100 kg/cm.sup.2 and a carbon monoxide/hydrogen mole ratio of 6:1 to 1:2 for the ester reaction and 10:1 to 1:2 for the ether reaction. When ethylidene diacetate is the product, it can then be decomposed to produce vinyl acetate and acetic acid by well-known techniques. Since one mole of acetic acid is also produced in the synthesis of the diacetate, the invention makes possible an overall process for the production of vinyl acetate which produces acetic acid rather than consumes it.

A catalyst system having high activity and selectivity to carbonylation products comprises a rhodium-containing catalytically active component and a halogen-containing promoter component, the halogen being selected from the group consisting of bromine, iodine, bromide compounds, and iodide compounds.

Carbonylation catalysts

The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) and iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases and unreacted olefin, alcohol or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the carbon monoxide deficient zones of the system of a catalyst stabilizer which is a germanium (IV) compound, an alkali metal compound, and mixtures thereof.

Carbonylation process with an alkali metal acetate as catalyst stabilizer

Rhodium-containing carbonylation catalysts with halogen-containing

The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system containing a rhodium component and an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer which is a tin component which may be tin or a tin compound.

Process for stabilizing carbonylation catalyst in soluble form

The present invention relates to a process for the preparation of dicarboxylic acids, specifically by the reaction of non-vicinal glycols; halogen containing derivatives in which the OH radical of the glycol is substituted by Cl, Br, or I; ester derivatives of glycols; and cyclic ether derivatives of glycols; with carbon monoxide in the presence of catalyst compositions essentially comprising rhodium or iridium compounds and complexes, together with a halide promoter.

Production of dicarboxylic acids

The present invention relates to an improved one-step process for the preparation of propionic acid, specifically by the reaction of ethylene with carbon monoxide and water at mild pressure, in the presence of catalyst compositions essentially comprising critical proportions of rhodium components with a bromide promoter. Under these reaction conditions, the process is catalytic both with respect to the rhodium and the bromide components.

Production of propionic acid

The present invention relates to an improved one-step process for the preparation of propionic acid, specifically by the reaction of ethylene with carbon monoxide and water at mild pressure, in the presence of catalyst compositions essentially comprising critical proportions of iridium components with a bromide promoter. Under these reaction conditions, the process is catalytic both with respect to the iridium and the bromide components.

Growing community of inventors

St. Louis, MO, United States of America

Frank E Paulik