Ethyl Corporation

Albemarle Corporation

Albermale Corporation

Bruce C Berris

John M Power

Donald R Bell

Chi-Hung Cheng

Charles H Kolich

Ronny W Lin

Arthur G Mack

Steven P Diefenbach

Bo Liu

Jamie R Strickler

William J Layman, Jr

John F Balhoff

Feng-Jung Wu

Douglas W Luther

David W Owens

Govindarajulu Kumar

Kimberly M White

Kevin Coppola

Rajeev S Mathur

Zhongxin Ge

Junzuo Wang

Troy E DeSoto

Jonathan P McCarney

Jorge Morice

Christopher D Claeboe

David A Caillet

Described are a particular group of novel aromatic hydrocarbon telomers that, on bromination, result in the formation of novel flame retardants having a uniquely beneficial combination of properties. The resultant flame retardants and uses thereof are also described. The disclosure includes descriptions of methods for preparing both the aromatic hydrocarbon telomers and the brominated flame retardant polymers.

Brominated flame retardants and precursors therefor

A process for the preparation of organic cation tetrakis(aryl) borate salts. The process includes preparation of intermediate, mono-hydrazine substituted (aryl) compound, from (aryl) compound using hydrazine at temperatures below 78&#xb0; C. A stoichiometric excess of hydrazine to the (aryl) compound to the (aryl) compound is used. The process further includes the preparation of the organic cation tetrakis(aryl) borate in ethereal medium.

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Processes are provided for producing triphenylene by combining at least dodecahydrotriphenylene, a dehydrogenation catalyst such as palladium on carbon, and an aliphatic solvent having a boiling point greater than 180&#xb0; C. to form a reaction mixture, heating the reaction mixture to at least about 180&#xb0; C. but lower than the boiling point of the aliphatic solvent, maintaining the temperature of the reaction mixture at 180&#xb0; C. but lower than the boiling point of the aliphatic solvent, and passing a purge fluid comprising an inert fluid through the reaction mixture, for a period of time adequate for production of triphenylene.

Processes for preparing triphenylene

Lithiated haloarenes, although useful as intermediates in the synthesis of various end products, can be hazardous to prepare since unstable, shock sensitive compounds can be formed during lithiation of haloarenes. To avoid this problem, a reaction of a polyhaloarene with a hydrocarbyl lithium compound is conducted in the presence of another reactant so that the lithiated haloarene, if formed at all, exists as a transitory intermediate in low concentration. In this way, transitory lithiated haloarene which may be, and presumably is, formed in the reaction is converted into a non-hazardous functionally-substituted haloarene essentially as soon as such lithiated haloarene is formed. Thus, an arene having a halogen atom of atomic number greater than 9 substituted on at least two non-adjacent carbon atoms is concurrently reacted with a non-fluoro halotrihydrocarbylsilane and a hydrocarbyl lithium compound, in proportions such that a haloarene having at least one trihydrocarbylsilyl ring substituent is formed.

Production of silated haloarenes by selective silylation of

Impure tetra(dihydrocarbylamino)phosphonium halide is contacted with a liquid cyclic ether to dissolve the phosphonium halide and leave at least a portion of the impurities comprising at least quaternary ammonium halide or an amidophosphoxide remaining in the solid state. The solids and the liquid phase are separated from each other, an anhydrous non-solvent for the tetra(dihydrocarbylamino)phosphonium halide is mixed with the separated liquid phase to precipitate the tetra(dihydrocarbylamino)phosphonium halide, which is then separated from the liquid phase. The so-treated tetra(dihydrocarbylamino)phosphonium halide is more efficient as a catalyst for halogen exchange reactions than the original untreated tetra(dihydrocarbylamino)phosphonium halide.

Catalysis in halogen exchange reactions

A metallocene having one or two hydrocarbyl groups bonded to a Group 4 metal are produced from a crude impure pasty or non-wet mixture containing at least 50% by weight of a metallocene having two halogen atoms bonded to a Group 4 metal atom, by (a) mixing liquid aromatic hydrocarbon with the crude impure pasty or non-wet mixture; (b) mixing a solution of an organolithium compound in a suitable anhydrous ether or paraffinic hydrocarbon solvent or a mixture thereof, with the mixture from (a) and agitating the resulting mixture so that lithium halide solids are formed; and (c) separating the solids and recovering the resultant liquid portion which is mainly a solution of the metallocene having one or two hydrocarbyl groups bonded to a Group 4 metal. Additional optional steps include (d) replacing the original solvent from the solution from (c) with a liquid paraffinic hydrocarbon diluent to form a slurry of product solids; and (e) recovering the product metallocene solids. Preferred organolithium compounds have the formula, RLI.nLiX, where R is tert-alkyl, aryl, alkaryl, benzyl, or alkyl-substituted benzyl, or most preferably, methyl, and X is Br or I.

Metallocene synthesis

A mixture is made from (i) a tris(dihydrocarbylamino) phosphoroamidite and/or a hydrohalide thereof, (ii) a strong base (e.g., NaOH) in proportions of about 2.0 to about 4.0 moles of (ii) per mole of (i), and (iii) at least one solvent for the base (e.g., H.sub.2 O). To this mixture is added a hydrocarbyl monohalide (e.g., EtBr) in proportions of about 1.0 to about 3.0 moles per mole of phosphoroamidite used in forming the initial mixture, and the resultant reaction produces tetrakis(dihydrocarbylamino)phosphonium halide. The process enables more efficient production of tetrakis(dihydrocarbylamino)phosphonium halides, and is capable of being effectively used in large scale production facilities while satisfying the economic constraints of commercial operations.

Preparation of tetrakis(dihydrocarbylamino)phosphonium halide

A 1,3,5-trimethyl-2,4,6-tris(3,5-dialkyl-4-hydroxybenzyl)benzene is prepared in high yield by reacting a 2,6-dialkyl-4-methoxymethylphenol with mesitylene in a hydrocarbon solvent and in the presence of at least about 10 mol %, based on the amount of mesitylene, of a hydrocarbon-soluble acid (e.g., an alkylbenzenesulfonic acid having 12-18 carbons in the alkyl group, a carboxylic acid, or a dialkylsulfosuccinate) as a catalyst or co-catalyst while distilling methanol by-product out of the reaction mixture as it is formed. The process may be conducted so as to provide a substantially pure product or a product, such as 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, having fairly high purity (e.g., about 98-98%) and a melting point much lower than would be expected of a product having such high purity.

Phenolic antioxidant and process

Improved methods for producing polysilane compounds using diphosphorous nickel chloride catalysts. Novel bicyclic polysilane compounds, among other compounds, can be produced using these improved methods.

Bicyclic polysilicon compounds

Improved methods for producing polysilane compounds using tetrakis(triethylphosphine)nickel (O) catalysts.

Method of producing polysilane compounds

Improved methods for producing polysilane compounds using diphosphorous nickel chloride catalysts.

A quaternary ammonium salt catalyst is recovered from mixtures where the salt is in contact with an aqueous alkaline phase by adding water to completely dissolve the salt and adding base to cause the dissolved catalyst to separate as a hydroxide which forms an oily upper phase.

Phase transfer catalyst recovery

Transition metal cyclopentadienyl carbonyl compounds of the formula:

Process for preparing transition metal cyclopentadienyl carbonyl

Improved methods for producing silanes using phosphorous rhodium dimer catalysts.

Growing community of inventors

Baton Rouge, LA, United States of America

Bruce C Berris