Ethyl Corporation

Albemarle Corporation

Won S Park

Everett M Marlett

Charles R Everly

William R Beard

K Pushpananda Senaratne

Arcelio J Malcolm

Andrew O Wikman

Liquid clathrate compositions useful as reusable aluminum catalysts in Friedel-Crafts reactions are described. In one embodiment, the liquid clathrate composition is formed from constituents comprising (i) at least one aluminum trihalide, (ii) at least one salt selected from alkali metal halide, alkaline earth metal halide, alkali metal pseudohalide, quaternary ammonium salt, quaternary phosphonium salt, or ternary sulfonium salt, or a mixture of any two or more of the foregoing, and (iii) at least one aromatic hydrocarbon compound.

Liquid clathrate compositions

A mixture formed from one or more alkyl disulfides, benzene, and at least about 1.5 equivalents of Lewis acid catalyst is heated to form alkanethiobenzene. Reaction in a mixture formed from excess benzene, dimethyldisulfide (DMDS) and AlCl.sub.3 in which the mole ratio of AlCl.sub.3 to DMDS was 2:1 was complete in 2 hours and afforded 98% conversion and 93% yield of thioanisole. In contrast, the same reaction when attempted using a 1:1 mole ratio of AlCl.sub.3 to DMDS after 6 hours achieved only 66% conversion and a thioanisole yield of only 35%. So far as is known, this is the first example of a highly efficient electrophilic aromatic substitution of the inactivated benzene ring by an alkanethio group.

Alkanethiolation process

Described are novel processes which employ reusable aluminum catalysts in Friedel-Crafts reactions. In one aspect, a novel process for producing a Friedel-Crafts reaction product is described, the process comprising: providing, to a reactor, aromatic reactant and a catalyst system, which system is formed from constituents which comprise (i) an aluminum compound selected from at least one aluminum trihalide, alkyl aluminum halide, or aluminum trialkyl, or a mixture of any two or more of the foregoing, (ii) a salt selected from alkali metal halide, alkaline earth metal halide, alkali metal or alkaline earth metal pseudohalide, quaternary ammonium salt, quaternary phosphonium salt or ternary sulfonium salt, or a mixture of any two or more of the foregoing, and (iii) an aromatic compound which may be the same as or different from the aromatic reactant, the aluminum compound (i), the salt (ii), and the aromatic compound (iii) forming a liquid clathirate which is immiscible in the Friedel-Crafts reaction product and which exhibits Friedel-Crafts catalytic activity. In a preferred embodiment, the liquid clathrate is recovered and reused to catalyze the same or a different Friedel-Crafts reaction.

Processes employing reusable aluminum catalysts

Non-solvated hydridomagnesium chloride is prepared in high yield under moderate conditions by reacting magnesium hydride and magnesium chloride in a hydrocarbon solvent and in the presence of a trialkylaluminum catalyst.

Preparation of hydridomagnesium chloride

Improved process for separating ethylsilane from silane by selective adsorption onto an effectively treated carbon bed and method of treatment of such carbon bed to enhance the selective adsorption of ethylsilane.

Silane compositions and process

Improved molecular sieves and processes for treatment of molecular sieves which permit use for separation of ethylene and silane without attending formation of ethylsilane. Such treatment includes treatment of sieves with silane at an effective temperature, pressure and time.

A process for preparing a silane mixture of the formula

Process for preparation of organosilicon halides

Tertiary amine alanes are produced by reacting sodium aluminum hydride and magnesium dichloride. A tertiary amine is admixed to extract the tertiary amine alane. Stoichiometric ratios of sodium aluminum hydride to magnesium dichloride can be varied to effect the magnesium compound by-product produced.

Preparation of amine alanes

A process for selective reduction is provided wherein an organic compound containing a reducible group such as acid, acid chloride, ester, aldehyde, ketone, epoxide, amide, oxime, imine, nitrile, or the like, is reacted with a tertiary amine alane such that an alcohol or an amine is produced, substantially without reduction of another group in the molecule such as a halogen-containing functionality, nitro group, or double bond.

Selective reducing agents

Improved processes for the production of silane. Hydridomagnesium chloride and trichlorosilane are reacted in an ether solvent to co-produce silane and magnesium chloride. Recycle schemes are presented for the recovery of magnesium values.

Silane production from hydridomagnesium chloride

Lithium aluminum hydride reacts with a tertiary amine to produce an amine alane and Li.sub.3 AlH.sub.6. Lithium values are recycled by reacting Li.sub.3 AlH.sub.6 with aluminum and hydrogen to produce LiAlH.sub.4. Since no metal halide by-product is produced in the first step, it has an advantage over other routes. The amine alane can react with SiF.sub.4 to produce silane and AlF.sub.3.

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Baton Rouge, LA, United States of America

Won S Park