Ethyl Corporation

Robert I Davidson

Ronny W Lin

Venkataraman Ramachandran

Nubar Ozbalik

John R Maloney

This invention relates to additives for oleaginous fluids containing extreme pressure and antiwear agents and containing less than 15 GC area percent higher dialkyl polysulfides and to a process for their production comprising:

Process for mixed extreme pressure additives

Perfluoroalkylaromatic compounds containing at least two carbons in the perfluoroalkyl group are prepared by reacting an aromatic bromide or iodide with a potassium perfluoroalkanoate corresponding to the formula KOOC(CF.sub.2).sub.n CF.sub.3 wherein n is an integer of at least one in the presence of cuprous iodide and a dipolar aprotic solvent.

Perfluoroalkylation process

Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with a tetraalkylammonium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.

Trifluoromethylation process

Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide, a phase transfer agent, and a dipolar aprotic solvent.

Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.

An olefin, especially an activated olefin, is telomerized by reaction with an arylamine, such as an aniline, in the presence of an alkyl nitrite, a copper catalyst, and a catalytic amount of water and/or acid and in the absence of more than about 0.5 volume part of inert solvent per volume part of olefin.

Telomerization of olefins

An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.

Arylation of olefins

6-Alkoxy-5-trifluoromethyl-1-naphthoic acids are prepared by (1) cyanating a 6-alkoxytetralone so as to form a 6-alkoxy-1-cyano-3,4-dihydronaphthalene, (2) converting the 6-alkoxy-1-cyano-3,4-dihydronaphthalene to a naphthoic acid precursor selected from a 6-alkoxy-1-cyanonaphthalene and a hydrocarbyl 6-alkoxy-1-naphthoate, (3) halogenating the naphthoic acid precursor to the corresponding 5-halo derivative, (4) trifluoromethylating the 5-halo derivative to replace the 5-halo substituent with a 5-trifluoromethyl group, and (5) hydrolyzing the resultant product to a 6-alkoxy-5-trifluoromethyl-1-naphthoic acid. In a preferred embodiment of the invention, the process is conducted so as to prepare 6-methoxy-5-trifluoromethyl-1-naphthoic acid, which, like the other products, is known to be useful as a pharmaceutical intermediate.

Substituted naphthoic acid process

An alpha-arylacrylonitrile is prepared by reacting an aryl ketone having a removable hydrogen alpha to the carbonyl group with a cyanide ion source which is free of radicals that would stabilize a cyanohydrin corresponding to the aryl ketone and with a Lewis acid in the presence of an activating amount of water and/or HCl and preferably in the presence of a solvent. In a preferred embodiment, the aryl ketone is a tetralone, the cyanide ion source is sodium cyanide, the Lewis acid is aluminum chloride, and the product is a 1-cyano-3,4-dihydronaphthalene.

Process for preparing alpha-arylacrylonitriles

An arylamine is coupled with an aromatic compound in the presence of water, an inorganic nitrite, and an alkanoic acid containing 5-7 carbons. In a preferred embodiment of the invention, 2-(4-amino-3-fluorobenzene)propionitrile is coupled with benzene in the presence of water, sodium nitrite, and hexanoic acid to form a flurbiprofen intermediate.

Aryl coupling process

Nitriles, such as 2-(2-fluoro-4-biphenyl)propionitrile, contaminated with ketones having similar boiling points are purified by treating the nitrile/ketone mixture with an alkali metal borohydride, e.g., sodium borohydride, to complex the ketone. After complexing of the ketone, the nitrile can be separated therefrom by distillation.

Nitrile purification

A 2-hydroxyacetonitrile is reacted with thionyl chloride in the presence of a trialkylamine and a suitable solvent to form a 2-chloroacetonitrile. In a preferred embodiment of the invention, 2-chloropropionitrile is prepared by reacting lactonitrile with an excess of thionyl chloride in the presence of triethylamine and dichloromethane.

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Baton Rouge, LA, United States of America

Robert I Davidson