Monsanto Company

The Nutrasweet Company

Bp Chemicals Limited

Monsanto Technology LLC

Arnold Hershman

Frank E Paulik

James F Roth

Denis Forster

Indra Prakash

Jerry R Ebner

Zhi Guo

Walter R Knox

Mark D Paster

Loraine M Klein

Donald E Morris

John H Craddock

David R Eaton

Robert G Schultz

James W Gambell

David E Gross

Walter K Gavlick

Gary Klopf

Anthony J Pearson

Donald J Bauer

Robert M Friedman

3,3-Dimethylbutanal is prepared from 3,3-dimethybutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converted 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.

Process for the preparation of 3,3-dimethylbutanal

3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.

The present invention is directed to an analytical method for measuring the concentration of an N-(phosphonomethyl)iminodiacetic acid (&ldquo;NPMIDA&rdquo;) substrate, an N-(phosphonomethyl)glycine product, formaldehyde, formic acid, N-methyl-N-(phosphonomethyl)glycine (&ldquo;NMG&rdquo;), N-methyl-aminomethylphosphonic acid (MAMPA) or aminomethylphosphonic acid (&ldquo;AMPA&rdquo;)) in an aqueous mixture thereof, using infrared spectroscopy. The present invention is also directed to a process for oxidizing an N-(phosphonomethyl)iminodiacetic acid substrate to form a N-(phosphonomethyl)glycine product, and as part of the process, measuring the concentration of at least one reactant, product or byproduct of the oxidation reaction using the analytical method of the present invention and controlling the oxidation process in response to the measurement taken.

Use of infrared spectroscopy for on-line process control and endpoint detection

3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.

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

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

Rhodium-containing carbonylation catalysts with halogen-containing

Processes are described wherein formaldehyde or formic acid and similar materials are oxidized to produce carbon dioxide and water by contact with oxygen in the presence of a noble metal catalyst on a carbon support that is protected from poisonous amines by a polymer coating.

Oxidation with coated catalyst

Tertiary amines such as alkyl or benzyl amines are catalytically oxidized by oxygen over an activated carbon catalyst to selectively produce secondary amines.

Production of secondary amines

Tertiary phosphonomethylamines are oxidized with oxygen, preferably in contact with activated carbon, to cause cleavage of a phosphonomethyl group and selective production of a secondary amine.

Oxidation of phosphonomethylamines

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 complexes [Ir(CO).sub.3 I], [HIr(CO).sub.3 I.sub.2 ], [HIr(CO).sub.2 I.sub.2 (H.sub.2 O)], [RIr(CO).sub.2 I.sub.2 ], [(RCO)Ir(CO).sub.2 I.sub.2 ] where R is an alkyl radical, are described. Processes for preparing the aforesaid complexes are described and in addition a new process for preparation of [Ir(CO).sub.3 I.sub.3 ] is described.

Iridium carbonyl complexes

The conversion of linear or branched primary diamines to saturated secondary cyclic amines with the repression of the formation of linear or branched secondary amines, tertiary amines and polymers is carried out in the vapor phase, with a diluent, preferably hydrogen, over a solid catalyst comprising an element selected from the group consisting of nickel, copper, cobalt or iron.

Repression of polymer formation in the conversion of linear or branched

The present invention relates to an improved process for the preparation of carboxylic acids, specifically by the reaction of ethylenically unsaturated compounds with carbon monoxide and water, in the presence of catalyst compositions essentially comprising iridium compounds and complexes, together with an iodide promoter, the improvement being the provision of at least 50 percent by weight of the iridium in the reaction solution in a highly catalytically active form as a species having infrared absorption bands at 2098 cm.sup.-.sup.1 (vs), 2155 cm.sup.-.sup.1 (w), 2180 cm.sup.-.sup.1 (vw, br). By monitoring the infrared absorption spectra of reacting solutions and following the magnitude of the 2098 cm.sup.-.sup.1 band the operating conditions are adjusted so that this band is present in 50 percent or more concentration relative to the infrared absorption spectral bands of the other iridium species in solution. Through this monitoring and control process significantly increased reactor productivity to carboxylic acids is achieved.

Growing community of inventors

St. Louis, MO, United States of America

Arnold Hershman