Ethyl Corporation

Albemarle Corporation

Gene C Robinson

Bonnie G McKinnie

Steven P Diefenbach

Ronny W Lin

G Patrick Stahly

Robert H Allen

Keith G Anderson

Andrew D Overstreet

Larry H Nemec

Charles R Everly

David C Eisenberg

William J Layman

A process for preparing tetraalkylated cyclopentadienes comprises (a) pyrolyzing an isobornyl carboxylate so as to form a mixture of 1,2,3- and 1,2,4-trimethylcyclopentadienes, (b) alkylating said mixture with an alkylating agent so as to form a mixture of alkyltrimethylcyclopentadiene isomers including 1,2,3,4-alkyltrimethylcyclopentadiene and, (c) thermally isomerizing the mixture of isomers obtained in step (b) so as to increase the proportion of 1,2,3,4-alkyltrimethylcyclopentadiene in said mixture of isomers.

Preparation of polyalkylated cyclopentadienes from isobornyl carboxylates

This invention relates to a process for preparing tetrahydrocarbylsilane in high yield, comprising: a) forming a reaction mass from molten metal and trihydrocarbylaluminum, in an hydrocarbon solvent under an inert gas atmosphere; b) maintaining the reaction mass at a temperature in the range of from about 100.degree. to about 130.degree. C. for a period of time sufficient to form sodium tetrahydrocarbylaluminate; c) contacting the sodium tetrahydrocarbylaluminate with organotrihalosilane; and d) heating the contacted tetrahydrocarbylaluminate and organotrihalosilane to a temperature and for a period of time sufficient to form the tetrahydrocarbylsilane, wherein the tetrahydrocarbylaluminate and tetrahydrocarbylsilane are formed at a pressure of less than about 3000 KPa and wherein the hydrocarbyl group of the tetrahydrocarbyl silane is one or a mixture of hydrocarbyl groups having less than about 8 carbon atoms each.

Synthesis of tetraalkylsilanes

Linear 1-olefins are prepared from internal olefins by (i) reacting them in the presence of an isomerization catalyst and a tri-lower alkyl aluminum so as to cause internal olefin to isomerize to 1-olefins which displace the lower alkyl groups to form a trialkyl aluminum compound in which at least one of the alkyl groups is a linear alkyl derived from the 1-olefin, and, thereafter, (ii) reacting the trialkyl aluminum compound with a 1-olefin so as to displace the linear alkyl from the trialkyl aluminum compound, thereby forming a linear 1-olefin product which is substantially free of internal olefins.

Aluminum alkyls and linear 1-olefins from internal olefins

Linear 1-olefins are prepared from internal olefins by (i) reacting them in the presence of an isomerization catalyst and a tri-lower alkyl aluminum so as to cause the internal olefin to isomerize to 1-olefins which displace the lower alkyl groups to form a trialkyl aluminum compound in which at least one of the alkyl groups is a linear alkyl derived from the 1-olefin, and, thereafter, (ii) reacting the trialkyl aluminum compound with a 1-olefin so as to displace the linear alkyl from the trialkyl aluminum compound, thereby forming a linear 1-olefin product which is substantially free of internal olefins.

The polyetherimides have repeating groups which may be represented by the general formula: ##STR1## They are produced from novel monomers of the formula ##STR2## Synthesis procedures for forming such monomers are also described.

Polyetherimide

Polyetherimides and their production

Alkyl groups in trialkyl aluminum are displaced by .alpha.-olefins in the presence of a nickel catalyst. The displaced alkyl group evolve as .alpha.-olefins. The displacement is fast and the catalyst is then poisoned with a catalyst poison such as lead to prevent undesired side reactions such as isomerization of .alpha.-olefins to internal olefins or dimerization to vinylidene olefins.

Nickel catalyzed displacement reaction

An alkali metal or an alkaline earth metal salt of an acyloxybenzenesulfonate of the formula: ##STR1## wherein R is a hydrocarbyl group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, aryl, aralkyl and M is an alkali metal or an alkaline earth metal is prepared by reacting at elevated temperature the corresponding hydroxybenzene sulfonate salt of the formula: ##STR2## with an aryl ester of the formula: ##STR3## wherein R is as defined above.

Alkanoyloxybenzenesulfonate salt production

4-(.alpha.-hydrocarbyl-.alpha.-cyano-methyl)2,6-di-substituted phenols having the formula ##STR1## wherein R is selected from hydrogen, hydrocarbyl radicals, substituted hydrocarbyl radicals and hydrocarbyloxy radicals and R.sub.1 and R.sub.2 are the same or different monovalent substituent selected from the group consisting of alkyl, aralkyl and cyclic alkyl radicals and are prepared by reacting a di-substituted phenol having the formula ##STR2## when R.sub.1 and R.sub.2 are as defined above with an aldehyde having at least one aldehyde radical and containing an R group as defined above and an alkali metal cyanide or an alkaline earth metal cyanide in a suitable solvent. The 4-(.alpha.-hydrocarbyl-.alpha.-cyano-methyl)2,6-di-substituted phenol thus formed can readily be converted to the corresponding 4-(.alpha.-hydrocarbyl-.alpha.-cyano-methyl)-phenol by dealkylating the substituent groups ortho to the hydroxyl group from the 4-(.alpha.-hydrocarbyl-.alpha.-cyano-methyl)-2,6-di-substituted phenol which then can be converted on hydrolysis to the corresponding .alpha.-hydrocarbyl-4-hydroxyphenylacetic acid. These acids are insecticidal and acaricidal intermediates and are deemed to have utility as insecticides themselves as are the 4-(.alpha.-hydrocarbyl-.alpha.-cyano-methyl)2,6-di-substituted phenols of the present invention.

Preparation of 4-(.alpha.-alkyl-.alpha.-cyano-methyl)-2,6-di-substituted

A process for making mixed dialkylmagnesiums wherein magnesium metal is reacted with ethylene and an alkyl halide in the presence of a hydrocarbon solvent and in a substantially moisture-free and ether-free atmosphere, under relatively high pressure and at a relatively high temperature followed by separation of undissolved solids from the resulting solution. A composition of matter produced by the process comprising dialkylmagnesium compounds having at least four different alkyl groups, a hydrocarbon solvent and a small amount of an alkyl or alkoxy aluminum compound.

Mixed dialkylmagnesium

A composition of matter comprising di-isoamylmagnesium and diethylmagnesium, with an isoamyl: ethyl alkyl group ratio of about 1.4 to about 4:1, which is soluble in aliphatic, cycloaliphatic, and aromatic hydrocarbon solvents is disclosed, as is a process for making such mixed dialkylmagnesium wherein magnesium metal is reacted with an ethyl halide and an isoamyl halide in the presence of the hydrocarbon solvent and in a substantially moisture-free and ether-free atmosphere, followed by separation of undissolved solids from the resulting solution.

Hydrocarbon soluble dialkyl magnesium composition

Adducts containing a six-membered olefinically unsaturated ring having a halogen atom on one of the ethylenic carbon atoms (e.g., 3,5-diketo-4,8-dioxa-12-chlorotricyclo[5.3.2.0.sup.2,6 ]-dodec-11-ene) are formed by heating a dienophile (e.g., maleic anhydride) with a gem-dihalocyclopropane which has at least 4 carbon atoms in the molecule and at least one hydrogen on a carbon atom singly bonded to the cyclopropane ring (e.g., 7,7-dichloro-2-oxabicyclo[4.1.0] heptane). The adducts have toxicological properties and thus may be used as insecticides, fungicides, bactericides, herbicides, miticides and the like. They are also useful in the manufacture of plasticizers, flameproofing agents, water mark detecting agents, waterproofing agents, degreasing solvents, surface active agents, and the like.

Diels-Alder type process involving a geminal-dihalocyclopropane and a

To obviate eutrophication of lakes, streams, etc., non-phosphorus highly biodegradable builders and sequestrants are provided for household and industrial use. These builders and sequestrants are either (1) a cis-2,5-disubstituted tetrahydrofuran in which the substituents are carboxy or carboxymethyl groups, (2) water soluble salts of such tetrahydrofurans, or (3) mixtures of (1) and (2). Conventional detergent actives may also be utilized in combination with the builders or sequestrants of this invention.

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Baton Rouge, LA, United States of America

Gene C Robinson