Amoco Corporation

Standard Oil Company (indiana)

The Standard Oil Company

Walter Partenheimer

Wayne P Schammel

Juergen K Holzhauer

George E Kuhlmann

Douglas E Fjare

Bruce I Rosen

Neal R Nowicki

Howard B Yokelson

Gregory P Hussmann

David A Young

Stephen V Hoover

Kristi A Fjare

Frank G Belmonte

Paul A Sanchez

Diane J Graziano

Jeffrey L Broeker

Robert K Gipe

John K Darin

James D Lowry, Jr

Gayle G Chany

Joseph D Figuly

A process for the manufacture of aromatic dicarboxylic acids is disclosed using a low bromine to metals ratio facilitated by the use of cerium along with the cobalt and manganese catalyst. Aromatic dicarboxylic acids such as terephthalic acid are useful in the manufacture of fiber, films, bottles and molded products.

Process for the manufacture of aromatic dicarboxylic acids utilizing

A process for preparing 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl) propane anhydride is disclosed. 1,1,1,3,3,3-hexafluoro-2,2-di(3,4 -dimethylphenyl) propane is oxidized under liquid phase conditions in the presence of an oxygen-containing gas, bromine and heavy metal catalyst components to 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl) propane in high yield. Addition of an anhydride of a low molecular weight carboxylic acid to the oxidation reaction mixture converts the 1,1,1-hexafluoro-2,2-di(3,4-dicarboxyphenyl)propane to 1,1,1,3,3,3-hexafluoro-2,2-di(3,4-dicarboxyphenyl) propane anhydride.

Preparation of 1,1,1,3,3,3-hexafluoro-2,2-Di(3,4-dicarboxyphenyl)propane

The addition of hafnium to oxidation catalysts provided by a heavy transition metal-bromine ion catalyst combination containing cobalt-manganese-bromine or manganese-bromine or cobalt-bromine and a soluble source of hafnium uniquely increases catalytic activity of the said catalyst combination for converting methyl groups on the benzene nucleus. The presence of hafnium in the total reactor contents is equal to or less than 250 parts per million by weight of the total reactor mother liquor. The solubility of the hafnium in the reactor solvent is such that reactor product cake contains less than 0.3 ppm by weight. Bromine emissions can be reduced.

Production of polycarboxylic acids with hafnium-activated cobalt catalyst

There is provided a process for the partial oxidation of a polymethylbenzene to the corresponding aromatic polycarboxylic acid, which process comprises contacting in a reaction zone said polymethylbenzene with molecular oxygen in the presence of an oxidation catalyst comprising at least one heavy-metal compound, said heavy-metal compound being acetate free, a source of bromine, and a non-metal acetate compound, the concentration of acetate in the reaction zone being employed to control the rate of oxidation and the selectivity of oxidation. There is also provided the catalyst that is employed in the process.

Process for making aromatic polycarboxylic acids and oxidation catalyst

A method for producing an aromatic polycarboxylic acid by oxidizing an aromatic feed compound having at least 3 oxidizable ring substituents, wherein, after initiation of the oxidation water from an external source is added and the reaction temperature is raised.

Process for the production of an aromatic polycarboxylic acid

The addition of molybdenum to oxidation catalysts provided by a heavy transition metal-bromine ion combination containing cobalt uniquely increases catalytic activity of said combustion for converting methyl groups to the corresponding carboxylic acid groups on the benzene nucleus. Such greater catalytic activity is manifested by higher yields of aromatic acids. The polycarboxylic acids produced by the novel process are useful as raw materials for fibers and films.

Production of polycarboxylic acids with a molybdenum-activated cobalt

A method for making 2,6-naphthalene dicarboxylic acid by the oxidation of 2,6-diisopropylnaphthalene or its oxidation derivatives in the presence of a catalyst comprising cobalt, manganese, cerium and bromine components is disclosed.

Method for making 2,6-naphthalene dicarboxylic acid

An improved process is disclosed for preparation of silicon-containing aromatic polyacids by liquid phase oxidation of a mono- or polyalkyl substituted diaryldialkylsilane in the presence of oxygen and a catalyst comprising cobalt-manganese-bromine. Bis(p-tolyl)dimethylsilane is oxidized to bis(p-carboxyphenyl)dimethylsilane and bis(3,4-dimethylphenyl)-dimethylsilane is oxidized to bis(3,4-dicarboxylphenyl)dimethylsilane.

Process for producing silicon-containing aromatic polyacids

A continuous process is disclosed for producing trimellitic acid by the liquid-phase air oxidation of pseudocumene in an acetic acid medium in the presence of a cobalt-manganese-bromine catalyst or a zirconium-cobalt-manganese-bromine catalyst wherein the mole ratio of cobalt-to-manganese is about 1.0:0.1 to about 1:5 and the ratio of zirconium-to-cobalt is about 0.005:1 to about 0.20:1, and mole ratio of bromine to total metals of said cobalt-manganese-bromine catalyst or zirconium-cobalt-manganese-bromine catalyst is from about 0.2:1.0 to about 2.0:1.0, which process comprises conducting the reaction continuously in two stages comprising a first-stage reaction at a temperature of about 250.degree. F. to about 350.degree. F. and a second-stage reaction at a temperature of about 350.degree. F. to about 450.degree. F. and recycling the cobalt-manganese catalyst or the zirconium-cobalt-manganese catalyst by oxalate precipitation of the catalyst at temperatures of about 250.degree. F. to about 375.degree. F. prior to the separation of mother liquor and using about 0.25 to about 2.5 moles of oxalic acid per mole of cobalt and manganese or mole of zirconium-cobalt-manganese and continuously recycling the recovered catalyst metals to the first-stage oxidation. The product of this novel process, trimellitic acid, is useful for the manufacture of polyamide-imides which are used as fibers or molded articles, including automotive parts.

Process for the manufacture of trimellitic acid

A novel method of oxidizing di- and trimethylbenzenes with molecular oxygen to the corresponding di- or tricarboxylic acid under liquid-phase conditions is disclosed. The process is conducted at a temperature of about 100.degree. C. to 260.degree. C. This process comprises conducting the oxidation in the presence of a catalyst system comprising a source of bromine with nickel, manganese and zirconium. The benzene di- and tricarboxylic acids have wide industrial application, including the manufacture of polyesters, polyamides, and fibers and films.

Oxidation process for the manufacture of aromatic acids from

A process for the manufacture of polycarboxylic acids having at least three carboxylic acid groups for each benzene ring is disclosed. In this novel process, water is used in the last third of the reaction to improve the yield of cobalt-manganese-bromine or oxidation system and eliminate catalyst deactivation. Polycarboxylic acids such as durene are converted to pyromellitic acid which is used to manufacture a polyimide ring used as molding compounds for replacement of metals.

Process for the production of aromatic polycarboxylic acids

This invention relates to the reclamation of metal oxidation catalysts by water extraction of a high boiling residual mixture remaining after separation of a benzene di- and/or tricarboxylic acid; e.g., the phthalic acids, trimesic acid or trimellitic acid and reaction solvent, if one is used, from the fluid oxidation effluents produced by the catalytic liquid phase oxidation of a xylene, mesitylene, psendocumene or o-xylene and psendocumene with a source of molecular oxygen in the presence or in the absence of a reaction solvent.

Minimizing oxygenated aromatic compound content of aqueous solution of

This invention relates to the selective removal of dissolved copper from an aqueous solution also containing dissolved cobalt, or manganese or cobalt and manganese with other extraneous metals such as iron, nickel and chromium and more particularly pertains to such removal of copper where its content and the respective contents of iron, nickel and chromium are a small fraction of; e.g., from 0.01 to 0.1 times, the concentration of cobalt, and manganese if present can be in a concentration from 2 up to 10 times the concentration of cobalt.

Removal of dissolved copper from aqueous solution also containing

This invention relates to the removal of nickel, iron and copper co-dissolved with cobalt or manganese, or cobalt and manganese in water so that cobalt, manganese, or cobalt and manganese can be precipitated as carbonates and then converted to their acetates sufficiently low in nickel, iron and copper so that said acetates can be recycled to the liquid phase air oxidation of a di- or trimethyl benzene to its corresponding di- or tricarboxylic acid without material inhibition of such oxidation.

Removal of nickel from cobalt and manganese

The present disclosure relates to a method for the stabilization of certain phosphorus-vanadium-oxygen complex catalysts by the repetitive reactivation of such catalysts using a specified class of reactivating agents. The present method is specifically applicable to the stabilization of phosphorus-vanadium-oxygen complex catalysts which are suitable for the production of maleic anhydride from aromatic or aliphatic feed streams. In a specific instance, the stabilization process incorporates passing a feed stream of an aliphatic hydrocarbon and oxygen over a phosphorus-vanadium-oxygen catalyst to cause it to deactivate, thereafter contacting the deactivated catalyst with a specified class of reactivating agents and thereafter repeating this sequence at least once. This process tempers the catalyst so it deactivates at a lower rate and is improved in its performance.

Growing community of inventors

Naperville, IL, United States of America

Walter Partenheimer