GB620038A - Improvements in and relating to the diazo-type process - Google Patents

Abstract

Diamines of the formula NH2-R-NZ-CO-R1-CO-NZ-R-NH2, wherein R is an arylene group which may be substituted, R1 is nothing, an aliphatic saturated or unsaturated chain which may or may not contain atoms other than carbon, a mixed aliphatic aromatic residue, or a hydroaromatic or aromatic residue, and Z is H, alkyl, or aryl, are prepared by reacting the acid chloride Cl-CO-R1-CO-Cl with the amine NHZ-R, nitrating and reducing. Adipyl-di-(2 : 5 - diethoxyanilide) is prepared by reacting adipyl dichloride with aminohydroaquinone diethyl ether in pyridine. Oxalyl-di-(2 - methoxyanilide) and terephthalyl - di - (2 : 5 - diethoxyanilide) are similarly prepared. Adipyl - di - (4 - nitro - 2 : 5 - diethoxyanilide) is prepared by nitrating p with fuming nitric acid an acetic acid solution of adipyl-di-(2 : 5-diethoxyanilide). Oxalyl - di - (4 - nitro - 2 - meth - oxyanilide), terephthalyl - di - (4 - nitro-2 : 5 - di - ethoxyanilide) maleyl - di - (p : p1 - nitro - N : N1\h - ethylanilide), p : p1 - dinitrodiglycollic acid anilide, m - phenylene - di - (p - nitroacetanilide), and hexa - hydroterephthaloyl-di-p-nitroanilide are similarly prepared. Adipyl - di - (4 - amino - 2 : 5 - diethoxyanilide) is prepared by reducing with iron and hydrochloric acid an alcoholic solution of adipyl-di-(4 - nitro - 2 : 5 - diethoxyanilide). Oxalyl-di-(4-amino - 2 - methoxyanilide) terephthalyldi - (4 - amino-2 : 5 - diethoxyanilide), maleyl - di - (p : p1-amino - N : N1 - ethylanilide hydrochloride), p : p1-diaminodiglycollic acid anilide hydrochloride, m - phenylene - di - (p - aminoacetanilide hydro - chloride), and hexahydroterexhthaloyl - di - (p - aminoacetanilide hydrochloride) are similarly prepared. M-Phenylenediacetyl chloride is prepared by reacting m-phenylenediacetic acid with thionylchloride.