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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C69-757
http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C409-00
filingDate 1960-04-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_94524cf44f6fe65417f01e577a52bf2c
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_9cf336373ed862ae557480d739c4bafe
publicationDate 1961-07-05-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-872355-A
titleOfInvention Improvements in or relating to the production of a tetrabasic acid and esters thereof
abstract 2.3.5-Tricarboxycyclopentaneacetic acid is produced by reacting one molar proportion of dicyclopentadiene with substantially two molar proportions of ozone in a medium comprising a carboxylic acid at a temperature of 10 DEG -45 DEG C. so as to obtain the diozonide and thereafter oxidising the resulting diozonide to 2.3.5-tricarboxycyclopentaneacetic acid, at least the final stage of the oxidation being effected with hydrogen peroxide in the presence of an acid having an ionization constant at least as great as that of formic acid. Suitable carboxylic acids for use in the ozonization step are, for example, formic, acetic, propionic, butyric, valeric, caproic, heptanoic, caprylic, pelargonic or capric acid and mixtures thereof. If desired additional inert liquids, e.g. esters, such as ethyl acetate, or water may be present. Preferably formic acid is used in the ozonisation step and this is suitable to serve as the acid in the oxidation step without further addition of other acid. The oxidation is carried out preferably at 50 DEG -103 DEG C. and may be effected, for example, partly by treatment with oxygen alone, oxygen with traces of ozone, or by hydrogen peroxide in acetic acid. For at least the final stage of the process the oxidation is carried out by hydrogen peroxide in the presence of an acid at least as strong as formic acid i.e. having an ionization constant of at least 2.14x10-4 e.g., sulphuric, nitric, phosphoric, benzene sulphonic, trichloroacetic or trifluoroacetic acid, or formic acid itself. The acid may be converted into esters by methods known per se and examples are given of the preparation of the tetramethyl and tetrabutyl esters. Examples are given of the preparation of the acid using hydrogen peroxide in the presence of sulphuric acid, formic acid, and trifluoroacetic acid as oxidising agents. When sulphate ions are present in the product they may be removed by ion exchange treatment.
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