Patent GB-730890-A (GB)
Title: Aromatic carboxylic acids and their derivatives and processes for preparing the same
IPC: C07C51/363
Filed: 1952-10-01
Abstract: The invention comprises polynuclear aromatic carboxylic acids containing 3-13 separate aromatic rings separated by bivalent aliphatic groups, and having at least 2 carboxyl groups attached to different rings from which linear polyesters may be prepared, the products obtained by hydrogenation of the aromatic rings, and the esters, salts and amides of such carboxylic acids some of which serve as plasticizers.  Also a process for preparing them, (see Group IV (b)).  Products containing polymerizable linkages give useful resins. In examples, dicarboxy dibenzylbenzene obtained by the process described is converted into a polyester with ethylene glycol suitable for filaments and fibres; other polyesters may be made with allyl, methallyl, ethallyl, and chloroallyl alcohols and 3-hexenol; the esters beated with benzoyl peroxide give hard, clear polymer sheets; moulded sheets can be obtained with a mixture of polyvinyl chloride and dicarbohexoxydibenzylbenzene (obtainable by the process described), or dicarbamyldibenzylbenzene, as plasticizers, with stabilizer.  For products for use as plasticizers, those in which the aromatic acid is esterified with specified alcohols, diols and triols of 1-10 C atoms and the amides and N-substituted amides of such acids, having alkyl substituents of 1-12 C atoms are preferred.  The cobalt, iron, manganese and lead salts of the polynuclear acids may be used as stabilizers for polyvinyl chloride.ALSO:The invention comprises polynuclear aromatic carboxylic acids containing 3-13 separate aromatic rings separated by bivalent aliphatic groups, and having at least 2 carboxyl groups obtained by hydrogenation of the aromatic rings, and the esters, salts and amides of such carboxylic acids; also a process for preparing the above compounds by the Friedel-Craft action of a haloalkyl-aromatic carboxylic acid or derivative thereof on an aromatic carboxylic acid or derivative thereof having a replaceable hydrogen in the ring, or an aromatic compound having at least 2 replaceable hydrogens.  In examples: 4-chloromethylbenzoic acid and its esters, and 3-chloromethylbenzoic acid, are condensed with benzoic acid, p-toluic acid, benzene, ethylbenzoate and other esters, and benzamide to give products including 4:41-dicarboxydiphenylmethane, 3 : 31 - dicarboxydiphenylmethane, dicarboxyphenyl - tolyl - methane, which may be esterified, dicarboxydibenzylbenzene, which may be esterified, carboethoxyphenylcarboxyphenyl methane, and similar esters, carbamylphenyl carboxyphenylmethane, dicarbohexoxy - dibenzylbenzene and related esters; 4-chloro-methylbenzamide and its N-alkyl and cycloalkyl derivatives react with benzene to give dicarbamyl- and N-substituted dicarbamyl-dibenzylbenzenes; potassium dicarboxydibenzylbenzene may be reduced with Raney nickel to give di-(carboxycyclohexylmethyl) cyclohexane.  A product containing 13 aromatic rings may be obtained by the action of a benzene derivative as described above, containing 4 reactive halogen atoms with a 1 : 4-bis-(phenoxymethyl) - benzene - 41 : 411 - dicarboxylic acid, which is among many aromatic acids specified.