Phillips Petroleum Company

Cobb, Raymond L.

Raymond L Cobb

Michael S Matson

Carl A Uraneck

Lawrence M Fodor

John E Burleigh

Michael D Mitchell

An acid-sulfolane catalyzed process of preparing cyclic alkylated compounds such as indanes by reacting a monovinyl aromatic compound with an olefinic compound, such reaction further improved by the addition of a lanthanide oxide, or Group VI A elements and/or oxides or a mixture of such oxides.

Acid-sulfolance catalyzed production of cyclic alkylated compounds

An improved process for preparing high yields of 4,4'-difluorobiphenyl comprised of reacting a p-halofluorobenzene Grignard reagent with a p-halofluorobenzene coupling reagent in the presence of a palladium chloride triphenylphosphine catalyst.

Process for preparing 4,4'-difluorobiphenyl

In a process for reacting an aromatic compound (preferably chlorobenzene) with free chlorine in the presence of a catalyst comprising a zeolite of the L family (zeolite L) under such reaction conditions as to obtain a product comprising 1,4-dichlorobenzene, the improvement comprises employing ammonium ion-exchanged zeolite of the L family.

Synthesis of 1,4-dichlorobenzene

1,2-dichlorobenzene is isomerized to 1,4-dichlorobenzene in the presence of a catalyst comprising (a) at least one of AlCl.sub.3 and AlBr.sub.3 and (b) at least one of iodine, alkaline earth metal halides and sulfates and lanthanide halides. Benzene and/or dichlorobenzene is chlorinated with free chlorine in the presence of a catalyst composition comprising (a) at least one suitable metal halide (preferably AlCl.sub.3, SbCl.sub.5 or FeCl.sub.3) and (b) free iodine and/or at least one organic iodo-compound (preferably methyl iodide of p-iodochlorobenzene), so as to obtain a reaction product comprising 1,4-dichlorobenzene. A preferred catalyst composition comprises (a) at least one of AlCl.sub.3 and AlBr.sub.3, (b) free iodine and (c) at least one of alkaline earth metal halides, alkaline earth metal sulfates and lanthanide halides.

Preparation of 1,4-dichlorobenzene

1,2-dichlorobenzene is isomerized to 1,4-dichlorobenzene in the presence of a catalyst comprising (a) at least one of AlCl.sub.3 and AlBr.sub.3 and (b) at least one of iodine, alkaline earth metal halides and sulfates and lanthanide halides. Benzene and/or dichlorobenzene is chlorinated with free chlorine in the presence of a catalyst composition comprising (a) at least one suitable metal halide (preferably AlCl.sub.3, SbCl.sub.5 or FeCl.sub.3) and (b) free iodine and/or at least one organic iodo-compound (preferably methyl iodide or p-iodochlorobenzene), so as to obtain a reaction product comprising 1,4-dichlorobenzene). A preferred catalyst composition comprises (a) at least one of AlCl.sub.3 and AlBr.sub.3, (b) free iodine and (c) at least one of alkaline earth metal halides, alkaline earth metal sulfates and lanthanide halides.

Monohalobenzene compounds are iodinated with an iodination reagent selected from the group consisting of (i) iodine monochloride and (ii) I.sub.2 /Cl.sub.2 mixtures having a mol ratio of about 1:3-5:1, in the presence of a catalyst selected from the group consisting of MoCl.sub.5, FeCl.sub.3, lanthanide chlorides and mixtures thereof. Preferably one of chlorobenzene and fluorobenzene is at least partially converted to at least one of para-iodochlorobenzene and para-iodofluorobenzene. Various other aromatic compounds, preferably di- and trichlorobenzene, xylenes, nitrobenzene and ethyl benzoate, are iodinated with an iodination reagent selected from the group consisting of (i) iodine monochloride and (ii) I.sub.2 /Cl.sub.2 mixtures having a mol ratio of about 1:3-5:1, in the presence of a catalyst comprising FeCl.sub.3 and, optionally, a lanthanide chloride.

Preparation of aromatic iodine compounds

An improved process for the removal of by-product amounts of undesirable aromatic hydrocarbon compounds from a mixture comprised of such compounds and predominantly tetramethyltetrahydronaphthalene is provided. In accordance with the process the mixture is contacted with a concentrated sulfuric acid solution whereby the undesirable aromatic hydrocarbons are dissolved therein and the acid phase containing said hydrocarbons is removed from the mixture.

Tetramethyltetrahydronaphthalene purification process

Hydrocarbon solutions containing iodine or iodine-containing impurities are rendered essentially color-free by distillation in the presence of small amounts of a hydrocarbon soluble organometallic compound.

Purification of iodine-containing mixtures and compositions useful

The alkylation of para-substituted isopropyl benzenes with dipentenes employing an aluminum halide catalyst system produces novel tetracyclic compounds.

Novel tetracyclic trienes

The self condensation of monovinyl aromatic compounds to acyclic dimers, the cross-reaction of monovinyl aromatic compounds with olefins in the presence of acid catalysts to produce cyclialkylated aromatic compounds, and the production of cyclialkylated aromatic compounds by reaction of olefins with acyclic dimers of monovinyl aromatic compounds in the presence of acid catalysts is improved by employing a tetrahydrothiophene 1,1-dioxide solvent.

Acid catalyzed reactions of monovinyl aromatic compounds

A process is provided for preparing polymethylbenzenes by simultaneously contacting (a) a phenolic compound, preferably phenol, with (b) a methylating agent, preferably methanol, in the presence of (c) zinc aluminate as catalyst, under such conditions as will result in the at least partial conversion of the reactants to either pentamethylbenzene or hexamethylbenzene or a mixture of both.

Preparation of polymethylbenzenes

The alkylation of aromatic compounds with olefinic compounds is catalyzed by catalyst consisting essentially of aluminum halide and elemental iodine.

Alkylation of aromatic compounds

In the production of 1,1-dimethyl-6-hydroxyindans through the reaction of phenols with isoprene or 2,3-dimethyl-1,3-butadiene in the presence of phosphoric acid, an improvement is comprised of using a phosphoric acid concentration of about 100% instead of 85% or less and also of the distillation of the product mixture from a solution containing phosphoric acid of about 95% concentration.

Process for production of 1,1-dimethyl-6-hydroxyindans

The alkylation of aromatic compounds with olefins can be conducted more efficiently in the presence of certain catalysts.

Growing community of inventors

Bartlesville, OK, United States of America

Raymond L Cobb