Phillips Petroleum Company

George B Fozzard

John R Norell

Jack E Reece

Robert A Paul

A solvent comprising at least one aromatic hydrocarbon and/or halogenated paraffin is used in a liquid extraction process for extracting diesters from mixtures comprising diesters, the corresponding monoesters and acids, diols and water.

Liquid extraction of diacetoxybutane with halogenated paraffins

Diacyloxyolefins are isomerized by contacting one or more diacyloxyolefins with a catalyst system comprising selenium dioxide and a suitable carboxylic acid. There can be additionally present in the catalyst system at least one compound selected from the group consisting of a carboxylic acid anhydride, a polar compound and an ionic reagent.

Diacyloxybutene isomerization catalysts comprising selenium dioxide and

Diacyloxyolefins are isomerized by contacting one or more diacyloxyolefins with a catalyst system comprising selenium dioxide and a suitable carboxylic acid. There can be additionally present in the catalyst system at least one compound selected from the group consisting of a carboxylic acid anhydride, a polar compound, and an ionic reagent.

Diacyloxybutene isomerization with selenium dioxide

An olefinically unsaturated mononitrile is reacted with a monadduct of an olefinically unsaturated mononitrile and an olefinically unsaturated hydrocarbon compound to produce a dinitrile product and undesired compounds having higher boiling points than the dinitrile product. The undesired compounds are separated from the dinitrile product and subjected to distillation to produce a light cut and a heavy cut thereof. The light cut is then subjected to pyrolysis conditions to decompose at least a portion thereof to olefinically unsaturated mononitrile, olefinically unsaturated hydrocarbon compound, and monoadduct, which can be recovered and recycled to the dinitrile synthesis.

Pyrolysis of heavies formed in production of unsaturated dinitriles

A process is provided for hydrogenation of unsaturated diesters produced by the reaction of conjugated diolefin and monocarboxylic acid in which the diester is contacted with hydrogen in the presence of a noble metal and a monoamine. The presence of the monoamine suppresses hydrogenolysis of the diester to monoester. In a preferred embodiment 1,4-diacetoxy-2-butene is hydrogenated in the presence of a palladium catalyst and a monoamine selected from methylamine, n-butylamine, triethylamine, tripropylamine, quinoline, and toluidine.

Suppression of side reactions in catalytic hydrogenation of diesters

Toluene/perfluoro-n-heptane mixtures, and employment thereof in the purification of perfluoro-n-heptane.

Constant boiling admixtures of toluene/perfluoro-n-heptane

Compounds of the formulas ##STR1## and mixtures thereof are prepared by codimerization of R.sub.f --CF.dbd.CF.sub.2 and R--CH.dbd.CH.sub.2. The cleavage product of the cyclobutane derivatives is copolymerized.

Fluoro compound preparation

A process is disclosed for obtaining a high purity perfluoro-n-heptane from an electrochemical fluorination product which comprises perfluoro-n-heptane, n-heptane, partially fluorinated heptanes, and water soluble acidic components such as hydrofluoric acid and is derived from the electrochemical fluorination of n-heptane.

Process for obtaining high purity perfluoro-n-heptane

In processes of preparing unsaturated dinitriles from olefins, unsaturated mononitriles, and a monoadduct reaction product of an olefin and an unsaturated mononitrile in which undesirable internally unsaturated monoadduct is formed, the improvement of inhibiting the formation of internally unsaturated monoadduct by decomposing at least a portion of the recycle stream of monoadduct to form olefin and unsaturated mononitrile, and passing the thus-formed olefin and unsaturated mononitrile to the reaction.

Unsaturated dinitrile preparation

Phenol, cyclohexanone, and cyclohexylbenzene containing mixtures are extractively distilled to provide overhead of cyclohexylbenzene and cyclohexanone and a kettle product substantially free of cyclohexylbenzene by employing a dialkyl and/or a dicycloalkyl phthalate. Co-agents or modifiers, e.g., sulfolane, polyalkylene glycols, etc., are advantageously used in some instances.

Separation of phenol, cyclohexanone, and cyclohexylbenzene containing

Phenol-cyclohexanone azeotrope, for example, resulting from the cleavage product of 1-phenylcyclohexylhydroperoxide resulting from the oxidation of cyclohexylbenzene, from which cyclohexylbenzene may have been separated, is subjected to an extractive distillation with a selective solvent essentially containing a diester of adipic acid, e.g. a dialkyl and/or a dicycloalkyl ester of adipic acid. Specifically disclosed is a separation of a cyclohexanone-phenol mixture employing di(2-ethylhexyladipate). The diesters up to and including diC.sub.14 are referenced.

Separation of phenol-cyclohexanone azeotrope by extractive distillation

Compounds of the formulas ##EQU1## and mixtures thereof are prepared by codimerization of R.sub.f -CF=CF.sub.2 and R-CH=CH.sub.2. The cleavage product of the cyclobutane derivative is copolymerized.

Tetrafluorocyclobutane is cracked to produce vinylidene fluoride and unavoidably minor amounts of tetrafluoroethylene and ethylene. The reaction effluent to which additional ethylene can be added is subjected to dimerization and/or codimerization conditions under which tetrafluoroethylene is converted to a product or products which can be removed from the desired vinylidene fluoride by conventional fractionation without danger of explosion. Separated tetrafluorocyclobutane can be recycled to the cracking operation. Octafluorocyclobutane can be cracked under optimum conditions in separate zone, usually more severe than those employed for tetrafluorocyclobutane.

Producing vinylidene fluoride substantially free from tetrafluoroethylene

Certain thiazolidine- and thiazine-2-thione compounds, including 4-carboxythiazolidine-2-thione and 3,4-tetramethylene-4H,5,6-dihydro-1,3-thiazine-2-thione, and methods for preparing same are disclosed.

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Bartlesville, OK, United States of America

George B Fozzard