Process for preparing chlorinated aromatics

Claim 1

A process for preparing a nuclear polychloro alkyl aromatic hydrocarbon without undue chlorination of the alkyl substituent on the aromatic hydrocarbon which comprises contacting an alkyl aromatic hydrocarbon, wherein the alkyl substituent has from one to 20 carbon atoms, with (1) a nitrate ion, a nitrite ion, NO or NO2, (2) HCl, (3) water, (4) molecular oxygen and (5) a protonic acid having an ionization constant at 25* C. greater than about 10 2 selected from the group consisting of perchloric acid, toluene sulfonic acid, trifluoroacetic acid, sulfuric acid and iodic acid at a temperature of about 15* to about 200* C. and a pressure of about 0.1 to about 10,000 pounds per square inch gauge for about 0.0001 to about 200 hours, wherein the amount of nitrate ion, nitrite ion, NO or NO2, on a molar basis, relative to the alkyl aromatic hydrocarbon reactant, is from about 2:1 to about 1:106, the initial molar ratio of HCl to the alkyl aromatic hydrocarbon reactant is in the range of about 4:1 to about 10.1, the amount of water, on a molar basis, relative to the alkyl aromatic compound reactant is in the range of about 1000:1 to about 0.1:1, the amount of molecular oxygen, on a molar basis, relative to the alkyl aromatic hydrocarbon reactant, is from about 1000:1 to about 1:10, and the amount of protonic acid, on a molar basis, relative to water, is from about 2:1 to about 1:20, and maintaining the molar ratio of HCl to the alkyl aromatic hydrocarbon reactant at approximately the initial level during the course of the reaction.