Ethyl Corporation

Albemarle Corporation

Lawrence H Shepherd, Jr

Edward A Burt

John Y Lee

Samuel A Sangokoya

Gerhard O Kuehnhanss

William J DeWitt

Meng-Sheng Ao

Robert M Moore, Jr

Kevin J Theriot

Stephen E Belmont

Niomi L Krzystowczyk

Richmond M Starrett

Clarinda M Whitton

Yueh-Dong Chen

Robert J Ellis

Edward G Woods

Eric P Breidenbach

An aluminoxane product is prepared by reacting water which contains a stabilizing agent, such as a lithium halide, with a hydrocarbyl aluminum compound, such as tri-methylaluminum, in an organic solvent. The product has increased resistance to gel-formation therein because of the stabilizing agent dissolved in the water used in forming the reaction product.

Aluminoxane process and product

A aluminoxane product is prepared by reacting water which contains a stabilizing agent, such as a lithium halide, with a hydrocarbyl aluminum compound, such as trimethylaluminum, in an organic solvent.

Exo-isomers of polyalkylcyclopentadienes are converted to endo-isomers by contacting the exo-isomers with an acid such as aqueous HCl.

Process for converting exo-isomers of alkyl substituted cyclopentadienes

Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.

Decarboxylation process

This invention relates to a process for reducing the biological activity in water by feeding a solution of BrCl stabilized by a hydrohalic acid or an aqueous halide salt into the water to be treated in an amount sufficient to effect the reduction of biological activity in the water thus treated.

Water treatment process

A process of selectively preparing p-bromo-o-alkylanilines (e.g. 4-bromo-2-methylaniline) by reacting o-alkylanilines (e.g., 2-methylaniline) with unadsorbed bromine in a solvent selected from the group consisting of an inert di- tri- or tetrahaloaliphatic hydrocarbon (e.g., dichloromethane and dibromomethane), an alkyl nitrile (e.g., acetonitrile) and mixtures thereof.

Para-bromination of ortho-alkyl anilines

Ether disulfonates or mixtures of ether monosulfonates and ether disulfonates are disclosed as useful surfactants in the recovery of oil.

Oil recovery process

An ether sulfinate/sulfonate or disulfonate having the following formula: ##STR1## wherein: R is a hydrocarbon group having from about 6 to about 24 carbon atoms,

Chemical composition

10-oxytetracyclo[4.2.1.2.sup.3,8.0.sup.2,5 ]undecane and its lower alkyl-substituted congeners and their synthesis by contacting a tricyclo[4.2.1.0.sup.2,5.0]non-7-en-3-yl-methanol with a strong acid so that cyclization occurs. The compounds of this invention have desirable fragrance characteristics and their stability against oxidative deterioration during storage, transportation, and use enhances their usefulness as fragrance materials.

Caged compounds and their synthesis

By treating a primary or secondary alkenol having an olefinic bond in the sixth position relative to the carbon atom carrying the hydroxyl group and at least one methyl group in the fifth position relative to said carbon atom with a strong acid (e.g., 85 percent phosphoric acid), 2,2-dialkyltetrahydropyrans are produced via a cyclization reaction. The products have desirable fragrance characteristics.

2,2-Dialkyltetrahydropyrans

Aldehydes are produced by cleaving 2,2-dialkyltetrahydropyrans bearing two hydrogen atoms in the sixth position with a strong acid. The 2,2-dialkyltetrahydropyran can be formed in situ by contacting the strong acid with a primary 6-alken-1-ol having at least one methyl group in the fifth position so that cyclization occurs.

Aldehyde synthesis

Chloro alkyl nitriles containing from about 3 to about 7 carbon atoms, such as chlorobutyronitrile, are produced in high purity by reacting the corresponding bromochloro alkane, typically 1-bromo-3-chloropropane, with alkali metal cyanide or alkaline earth metal cyanide in an aqueous system in the presence of catalyst of the formula (R).sub.4 MX wherein M is a Group V-A element; one, two or three of the R groups are lower alkyl having from 1 to about 4 carbon atoms, or phenyl; each of the other R groups is alkyl having from 2 to about 20 carbon atoms, or phenyl; X is a compatible anion such as chlorine, iodine, or bromine atom or a hydroxyl group. Such catalysts, especially tributyl methyl ammonium chloride, bromide, or iodide are effective during the reaction and are readily removed from the product after the reaction. Organic phase product from this reaction is purified in a sequence of several steps. Preferably, it is washed with water to remove at least a part of the residual catalyst present therein. Then the washed product is subjected to distillation to remove unreacted bromochloro alkane. After distillation, contaminant bromo alkyl nitrile is converted to chloro alkyl nitrile by a reaction with a water soluble chloride salt in the presence of catalyst of the foregoing type, additional catalyst being added if necessary. Following the last reaction, the aqueous and organic phases are separated removing the bromine as the bromine counterpart of the water soluble chloride salt used in the last reaction and the product is again washed with water to remove at least part of the catalyst used in the purification reaction.

Purification of chlorobutyronitrile

Tricyclo[4.2.1.0.sup.2,5 ]non-7-enes wherein the 3 position is substituted by a methylol group may be made by reacting a bicyclo[2.2.1]hepta-2,5-diene with a 2-alkenyl magnesium compound in a 1:1 ratio to yield a molecular addition product which is then oxidized and hydrolyzed to give the 3-methylol product. These substituted tricyclo[4.2.1.0.sup.2,5 ]non-7-enes are useful, inter alia, as intermediates for the manufacture of lubricating oil additives and various other useful products and they may be used for gas scrubbing applications and the like.

Growing community of inventors

Baton Rouge, LA, United States of America

Lawrence H Shepherd, Jr