Abstract: A process for the production of 1,12-dodecanoic diacid by hydroformylating an olefin in the presence of a rhodium catalyst and oxidation with oxygen of the aldehyde which is thus formed wherein 1,9-decadiene is hydroformylated in the presence of hydridotris-triphenylphosphine-rhodium-carbonyl combined with triphenylphospine and/or triphenylphosphite, and the 1,12-dodecanedialdehyde which was thus formed is oxidized with oxygen in the presence of inorganic or organic Co(II) salts.

Abstract: 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as unreacted carbon monoxide, inert gases and unreacted olefin, alcohol or alcohol derivatives are vaporized and can be withdrawn from the separation zone.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.

Abstract: A process for the production of 1,12-dodecanoic diacid by hydroformylating an unsaturated carboxy compound in the presence of a rhodium catalyst and oxidation of the aldehyde with oxygen, wherein undecyl-10-ene-acid is hydroformylated in the presence of hydridotristriphenylphosphine-rhodium-carbonyl combined with triphenylphosphine and/or triphenylphosphite, and the 11-formyl undecanioc acid which is thus formed is oxidized with oxygen in the presence of inorganic and organic Co(II) salts.

Abstract: Carboxylic acid esters are produced by reacting an unsaturated hydrocarbon, for example an olefin or an alkyne, with carbon monoxide and an alcohol in the presence of a protonic acid and as catalyst (a) at least one of the metals palladium, rhodium, ruthenium, iridium and cobalt, and (b) copper. In a modification of the invention carboxylic acids are produced by omitting the alcohol reactant and replacing it with water in an amount up to 8 mole equivalents based on the unsaturated hydrocarbon and a solvent other than an alochol, for example tetrahydrofuran.

Abstract: Carboxylic acid esters are produced by reacting an olefinic hydrocarbon with an ester of formic acid in the presence of both carbon monoxide and oxygen at a temperature of up to 200.degree. and a pressure of up to 300 bar in the presence of water, typically in an amount of from 0.01 to 5% w/w, a source of protons, which is preferably a mineral acid or a tectometallosilicate in the hydrogen form, and as catalyst (a) a source of palladium, and (b) a source of copper.

Abstract: A process for the selective hydrocarboxylation of propylene to produce predominantly isobutyric acid in the liquid phase is provided. The reaction of propylene, carbon monoxide and water is effected at a temperature of about 75.degree. C. to about 150.degree. C. and at a pressure of about 250 psi to about 5000 psi in the presence of a suitable solvent and a catalyst comprising palladium or a palladium compound supported on an inert carrier, an organo-arsine ligand compound and a hydrogen halide.

Abstract: A carboxylic acid, such as propionic acid, is prepared by carbonylation of an olefin, such as ethylene in the presence of water by the use of a molybdenum-nickel-alkali metal, tungsten-nickel alkali metal, or chromium-nickel-alkali metal co-catalyst in the presence of a halide.

Abstract: The preparation of 3-pentenoic acid by hydrocarboxylating butadiene with carbon monoxide and water in the presence of a rhodium-containing catalyst, an iodide promoter and certain inert halocarbon solvents, e.g., methylene chloride.

Abstract: Alkylcarboxylic acids (where alkyl is of 6 to 20 carbon atoms) are manufactured by hydrocarboxylating the corresponding olefins by means of cobalt carbonyl compounds in the presence of from 0.5 to 1.5 kg of N-methylpyrrolidone, per kg of the olefin, as the solvent.

Abstract: A novel method for producing branched carboxylic acids or esters from alpha-unsaturated olefins is disclosed. Such olefins are reacted with a novel, sterically hindered, ortho substituted phenylphosphine palladium halide catalysts in the presence of water or primary or secondary alcohols to produce high branched end product yields. Such catalysts have phosphine ligand cone angles of between about 170.degree. and 180.degree.. Tris(o-methoxyphenyl)phosphine palladium halide and o-trifluoromethylphenyldiphenylphosphine palladium halide catalysts are preferred.

Abstract: Substituted succinic acid amides, in particular substituted succinic acid amides containing differing derivative groups, are prepared by reacting unsaturated carboxamides with carbon monoxide and with a nucleophilic component containing at least one mobile hydrogen atom, in the presence of cobalt compounds and, if appropriate, in the presence of one or more tertiary nitrogen bases, under an elevated pressure and at an elevated temperature.

Abstract: Carboxylic acids, for example n-butyric and isobutyric are prepared from an olefin such as propylene in a process comprising passing a liquid feed consisting of an olefin, an alkyl halide or heterocyclic amine promoter, a protonic coreactant, and a low concentration of a soluble metal catalyst, optionally in the presence of a solvent, and a gas consisting essentially of carbon monoxide over a carbon bed maintained at a temperature of from about 200.degree. C. to about 400.degree. C. and a pressure of from about 500 psi to about 4000 psi or greater.

Abstract: Reaction mixtures which are obtained on hydroformylation or carbonylation of olefinically unsaturated compounds and which contain dissolved non-volatile complex compounds of metals of group VIII of the periodic table are worked up by a method wherein the products, after distillative removal of low-boiling constituents alone, or of these constituents plus a part of the high-boiling residue, or a part of the high-boiling residue after distillative removal of the desired products, are or is extracted with carbon dioxide, a C.sub.2 -C.sub.4 -paraffin, a C.sub.2 -C.sub.4 -olefin or a normally gaseous halohydrocarbon at above the critical temperature and above the critical pressure of these (extractant) compounds.

Abstract: A process for the selective hydrocarboxylation of propylene to produce predominantly isobutyric acid in the liquid phase is provided. The reaction of propylene, carbon monoxide and water wherein a water to propylene ratio is maintained of from about 0.01 to a value less than 1.0 is effected at a temperature of about 75.degree. C. to about 150.degree. C. and at a pressure of about 250 psi to about 5000 psi in the presence of a carboxylic acid solvent and a catalyst comprising a coordinating palladium compound, an organo-arsine and a hydrogen halide.

Abstract: Process using selected sulfones, e.g., tetramethylenesulfone as solvents in the carbonylation of nitriles, e.g., 3-pentenenitrile and acids, e.g., 3-pentenoic acid to produce highly linear products.

Abstract: The present invention provides an improvement in methods for preparing and processing readily polymerizable acrylate monomers. The improvement comprises employing phenyl-para-benzoquinone, 2,5-di-phenyl-para-benzoquinone, and mixtures thereof as process inhibitors. The process inhibitors are present in a concentration of about 50 to 3000 ppm, preferably about 250 to 2000 ppm, and most preferably about 500 ppm.

Abstract: A process for the selective hydrocarboxylation of propylene to produce predominantly isobutyric acid in the liquid phase is provided. The reaction of propylene, carbon monoxide and water is effected at a temperature of about 75.degree. C. to about 150.degree. C. and at a pressure of about 250 psi to about 5000 psi in the presence of a suitable solvent and a catalyst comprising palladium or a palladium compound, a phosphoamine promoter ligand compound and a hydrogen halide.

Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen oxide compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.

Abstract: 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) 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 component selected from N,N,N',N'-tetramethyl-o-phenylenediamine and 2,3'-dipyridyl.

Abstract: 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.

Abstract: Carbonylation of olefins is carried out in the presence of a hydroxylic compound, carbon monoxide and a catalyst system comprising an organic phosphine liganded palladium compound and a perfluorosulfonic acid.

Abstract: A process for hydroformylating olefinically unsaturated compounds by means of rhodium/triphenylphosphine/carbonyl complexes formed in situ from rhodium acetate, triphenylphosphine and carbon monoxide, wherein the hydroformylation reaction is preceded by a starting phase in which the mixture of the hydroformylation medium, the triphenylphosphine and rhodium acetate is heated at from 90.degree. to 120.degree. C. under a CO/H.sub.2 pressure of from 5 to 20 bar and the acetic acid liberated is discharged from the reactor in gaseous form in a stream of CO and H.sub.2, until virtually no more acetic acid can be detected in this gaseous discharge.

Abstract: A carboxylic acid, such as propionic acid, is prepared by carbonylation of an olefin, such as ethylene in the presence of water by the use of a molybdenum-nickel or tungsten-nickel cocatalyst in the presence of a promoter comprising an organophosphorus compound or an organo-nitrogen compound wherein the phosphorus and nitrogen are trivalent and in the presence of a halide.

Abstract: Alkanoic acids containing largely the alpha-methyl isomers thereof, and/or the corresponding esters, are prepared by reacting an alpha-olefin, carbon monoxide and water and/or a monoalkanol in the presence of a catalytically effective amount of a catalyst composition comprising (i) a zero-valent Group VIII metal or metal alloy in which the Group VIII metal is the major component by weight thereof, (ii) an aryl ligand selected from the group consisting of arylarsine, arylstibine and arylbismuthine and (iii) a Lewis acid and/or hydrochloric acid.

Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt or ruthenium carbonyl and a promoter ligand. The promoter ligand is selected from the group consisting of heterocyclic nitrogen oxide compounds and phosphorus or sulfur oxides. These reactions are carried out under relatively mild conditions of temperature and pressure.

Abstract: A one-step process is disclosed for forming a carboxylic acid and its anhydride directly from the corresponding olefin which comprises reacting the olefin with carbon monoxide, hydrogen and oxygen in the presence of a stable rhodium complex catalyst. The rhodium catalyst is stabilized by a pentavalent Group V ligand, such as a phosphine oxide. The reaction is preferably conducted in an inert organic solvent. In an alternate embodiment, a carboxylic acid may be obtained by oxidation of an aldehyde (produced, for example, by hydroformylation of the corresponding olefin) in the presence of a rhodium complex catalyst stabilized by a pentavalent Group V ligand. This reaction is also preferably conducted in an inert organic solvent.

Abstract: A N-acyl .alpha.-amino acid is manufactured by reacting an unsaturated vegetable oil or a C.sub.8 -C.sub.30 mono-olefinic compound with an amide, carbon monoxide and hydrogen, in the presence of a cobalt catalyst. The process is operated in one step, providing for an increased selectivity as compared with a two-step process.

Abstract: Water, primary alcohols or secondary alcohols together with carbon monoxide can be added across ethylenic or acetylenic bonds in a wide variety of organic compounds to form acids or esters. The reaction is conducted in the presence of a catalyst system consisting of an organophosphorus palladium halide compound and certain metal halide compounds.

Abstract: A solid supported catalyst useful in the carbonylation of olefins represented by the formula ##STR1## wherein Resin- represents a cross-linked solvent swellable high molecular weight resin; X represents a halide; m+n=4. A method for the carbonylation of .alpha.-olefins using the above-mentioned solid-supported catalyst.

Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.

Abstract: A carbonylation process is provided for conversion of olefinically unsaturated hydrocarbons to a mixture of esters or acids with a high ratio of iso:normal ester or acid by reaction with carbon monoxide and a hydroxylic compound, said process being carried out in the absence of added hydrogen or oxygen and in the presence of a palladium salt complexed with an arsine or stibine ligand as catalyst; 2-10 additional moles of arsine or stibine ligand per mole of catalyst may be present in said process to further enhance the ratio of iso:normal product and to promote catalyst stability. The catalyst, for example, may be palladium dichloride bis(triphenylarsine) or palladium dichloride bis(tri-p-tolyl arsine).

Abstract: Differential esterification or hydrolysis is utilized to effect separations of isomeric acids or esters.

Abstract: This invention relates to the selective production of fatty acid derivatives from aliphatic diene substrates, such as 1,3-butadiene, in the presence of dual-function homogeneous palladium complexes and certain classes of organic tertiary nitrogen bases.

Abstract: The present process is suitable for preparing carboxylic acids wherein greater than 50 mole percent of the carboxylate groups are at the terminal position which comprises bringing together in a reaction zone an olefin or mixture of olefins wherein greater than 50 mole percent of the olefin has unsaturation at other than the terminal position, water and carbon monoxide in the presence of a cobalt catalyst and a pyridine-type promoter, preferably pyridine, in a mole ratio of promoter to catalyst between about 5:1 and 15:1, at pressures from about 70 kilograms per square centimeter to about 300 kilograms per square centimeter, at temperatures between about 180.degree. C. and about 220.degree. C.

Abstract: The rate of reaction of ethylenically unsaturated compounds, carbon monoxide and water in the presence of catalyst systems consisting essentially of a rhodium or iridium compound and a halogen promoter to produce carboxylic acids is accelerated by including a minor amount of a compound of cobalt, iron or manganese in the reaction system.

Abstract: This invention relates to the selective production of fatty acid derivatives from aliphatic diene substrates, such as 1,3-butadiene, in the presence of dual-function homogeneous palladium complexes and certain classes of organic tertiary nitrogen bases.

Abstract: An improved process for the simultaneous and continuous production of acetic and propionic acids in a single reactor wherein the rate of propionic acid production is enhanced over that which prevails when this acid is produced separately in the same reactor under the same conditions, said rate enhancement being achieved by the introduction of methanol at a critical rate.