Process for the preparation of diphenylmethane dicarbamates and polymethylene polyphenyl carbamates
AssigneeAtlantic Richfield Company
InventorEdward T. Shawl
Life of this patent
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Abstract
Diphenylmethane dicarbamates and polymethylene polyphenyl carbamate homologs and derivatives of these compounds are produced by the acid catalyzed condensation of an N-aryl carbamic acid ester, such as ethylphenylcarbamate, with a carbonyl compound, such as formaldehyde, at a reaction temperature of from about 30.degree. C. to 170.degree. C. while removing any water added with the reactants and the water of condensation formed in the reaction, by azeotropic distillation with an azeotroping solvent which is non-reactive with the reactants and products of the condensation and which form a binary minimum-boiling azeotrope with water within the condensation, temperature range at atmospheric, sub-atmospheric or super-atmospheric pressure.
Claims9
In a process for the preparation of a mixture of diphenylmethane dicarbamates and polymethylene polyphenyl carbamates by the acid catalyzed condensation of an N-aryl carbamic acid ester with formaldehyde, para-formaldehyde or trioxane or mixtures thereof, at temperatures of from about 30.degree. C. to 170.degree. C., the improvement which comprises removing from the reaction zone with water collection means, during said condensation, water added with reactants and water of condensation by azeotropic distillation with an inert water-azeotroping solvent which forms a binary minimum-boiling azeotrope with water within the condensation temperature range at atmospheric, sub-atmospheric or super-atmospheric pressure, in order to maintain an acid concentration of at least 75 weight percent during the reaction and reduce production of N-(alkoxycarbonyl)phenylaminomethylphenyl impurities.
In a process for the preparation of a mixture of diphenylmethane dicarbamate, diethyl ester and polymethylene polyphenyl carbamates, ethyl esters, by the acid catalyzed condensation of ethylphenylcarbamate with formaldehyde at a temperature of from about 50.degree. C. to 130.degree. C., the improvement which comprises removing from the reaction zone with water collection means, during said condensation by azeotropic distillation with from 25 to 75 weight per cent, based on the total reaction mixture, of an inert water-azeotropic solvent which forms a binary minimum-boiling azeotropic with water within the temperature range of from 50.degree. C. to 130.degree. C. at atmospheric, sub-atmospheric or superatmospheric pressure, in order to maintain an acid concentration of at least 75 weight percent during the reaction and reduce production of N-[(ethoxycarbonyl)phenylaminomethyl]phenyl carbamate acid, ethyl ester impurities.
Dependencies are inferred from the claim text.