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filingDate 1930-03-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1931-07-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-353464-A
titleOfInvention Improvements in the synthesis of aromatic compounds at high pressures
abstract Aurines; hydroxy carboxylic acids; hydroxy ketones; ethers; amines; ureas; amino carboxylic acids; aminoketones; resins.-Organic compounds are synthesized by reacting carbon dioxide with aromatic hydroxy or amino bodies in the presence of metallic halides of the type adapted to promote the Friedel and Craft's reaction under conditions of high pressure and moderate or elevated temperature. Aluminium, zinc and iron halides are specified as suitable catalysts, and pressures greater than 10 atmospheres and temperatures between 80 and 150 DEG C. as suitable reacting conditions. The course of the reaction is affected by the pressure and temperature conditions, the duration of the reaction, and the particular catalyst employed. The following details are recorded :-(1) Phenol in presence of aluminium chloride at 70 atmospheres and 105-110 DEG yields 4.41-dihydroxybenzophenone and a little aurin; at 90 atmospheres salicylic acid is formed; at 70 atmospheres and 150 DEG the main product is 2.41- (admixed with some 4.41-)-dihydroxybenzophenone, together with aurin, an isomer of aurin (probably containing one o-hydroxy grouping), and salicylic acid; at 120 atmospheres and 200 DEG diphenylether is formed: (2) m- and p-cresol in presence of aluminium chloride at 70 atmospheres and 150 DEG yield m- and p-cresotinic acids respectively: (3) o-cresol in presence of aluminium chloride at 70 atmospheres and 150 DEG yields a bright red substance (probably an analogue of aurin) and 2.41-dihydroxy-3.51-dimethylbenzophenone (which substance is also prepared by condensing o-cresotinic acid with o-cresol in presence of stannic chloride; it dyes chromemordanted wool a light yellow): (4) b -naphthol and resorcin in presence of aluminium chloride are resinified: (5) aniline in presence of aluminium chloride at 60 atmospheres and 130 DEG yields diphenylurea: (6) ethylaniline in presence of aluminium chloride at 60 atmospheres and 110-150 DEG yields mainly monoethyldiphenylurea (which is also prepared by condensing phenylisocyanate with ethylaniline at room temperature) together with diphenylurea and diethyldiaminobenzophenone; in presence of zinc chloride at 70 atmospheres and 150 DEG p-ethylaminobenzoic acid is obtained: (7) dimethylaniline in presence of zinc chloride at 70 atmospheres and 150 DEG yields p-dimethylaminobenzoic acid; in presence of aluminium chloride at 65 atmospheres tetramethyldiaminobenzophenone, tetramethyldiaminodiphenylmethane and p-dimethylaminobenzoic acid are obtained. The Provisional Specification is not confined to the treatment of amino and hydroxy bodies, but refers to aromatic compounds generally. Specification 307,223, [Class 2 (iii), Dyes &c.], are referred to.
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priorityDate 1930-03-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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