Processes employing reusable aluminum catalysts

A process for alkylating (A) an alkylatable mononuiclear aromatic reactant of the formula:

• ##STR2## where Q.sup.1 and Q.sup.2 are the same or different and each is a hydrogen atom, an alkyl group, or an aprotic substituent, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be the same or different and each is either a hydrogen atom or an alkyl group, at least one of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 being a hydrogen atom, with (B) a haloalkane having from 1 to 2 halogen atoms, with the proviso that when 2 halogen atoms are present, the respective halogen atoms are bonded to different carbon atoms, the process comprising:
• (a) agitating a reaction mixture of the aromatic reactant and the haloalkane in the presence of a catalyst system which is formed from constituents which comprise,
• (i) an aluminum compound comprising, at least one aluminum trihalide, alkyl aluminum halide, 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, 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;
• (b) subsequent to (a), causing the formation of a first layer comprised of a liquid clathrate which is formed from constituents comprising, (i), (ii) and (iii), which is immiscible in the Friedel-Crafts reaction product, and which exhibits Friedel-Crafts catalytic activity, and a second layer comprised of the alkylated aromatic reactant;
• and
• (c) optionally, recovering at least a portion of the liquid clathrate layer for use in a subsequent Friedel-Crafts reaction mixture to provide at least a part of the catalyst needs for such subsequent reaction mixture.

A process for enriching the 1,2-bis(3,4-dimethylphenyl)ethane content of a mixture of bis(dimethylphenyl)ethanes, the process comprising:

• agitating the mixture in the presence of a catalyst system, at least a portion of the system being present as a liquid clathrate 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 any one of the aromatic reactants.

A process for the production of 1,2-bis(3,4-dimethylphenyl)ethane, the process comprising:

• (a) agitating a reaction mixture comprised of o-xylene and a dihaloethlane in the presence of a first catalyst system which is formed from constituents which comprise,
• (i) an aluminum compound selected from at least one aluminum trihalide, alkyl aluminum halide, 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, ternary sulfonium salt, or a mixture of any two or more of the foregoing, and
• (iii) o-xylene;
• to form a reaction product;
• (b) causing the formation of the reaction product of a first layer comprised of a liquid clathrate which is formed from constituents comprising (i), (ii) and (iii), which is immiscible in the reaction product, and which exhibits Friedel-Crafts catalytic activity, and a second layer comprised of alkylated o-xylene;
• (c) separating the first layer and the second layer from each other;
• (d) recovering 1,2-bis(3,4-dimethylphenyl)ethane from the second layer;
• (e) thereafter, agitating at least a portion of the second layer with at least a portion of the liquid clathrate and optionally a second catalyst system which is formed from constituents which comprise,
• (i) at least an aluminum compound comprising at least one aluminum trihalide, alkyl aluminum halide, aluminum trialkyl, or a mixture of any two or more of the foregoing, and optionally,
• (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, terniary sulfonium salt, or a mixture of any two or more of the foregoing, and
• (iii) o-xylene, and repeating steps (b), (c) and (d).