Exhaustive Chlorination as a Technique in the Analysis of Aromatic Hydrocarbons

Abstract Perchlorination reactions of aromatic compounds have been further investigated. The preparation and properties of decachlorodiphenyl ether and the isomeric o-, m-, and p-tetradecaehloroterphenyls are described. Anthracene, as an example of a polycyclic aromatic hydrocarbon, gave octachloroanthraquinone when treated with the antimony pentachloride iodine reagent, but quantitative conversion to decachloroanthracene could not be obtained with reagent BMC (sulfuryl chloride-aluminum chloride-sulfur monochloide). A new reagent, trichlorosulfur tetra-chloroaluminate (SCl3+ AlCl4), was shown to convert Aroclor 1254 to decadilorobiphenyl. As an application of the perchlorination technique it was shown that polychlorodibenzofurans (dibenzofuran) are not present at 0.5 g/g in samples of Halowax 1014 and technical naphthalene, respectively. Well defined derivatives could not be obtained when phthalate esters or hexabromobiphenyl (fireMaster BP-6) were treated with the BMC or SbCl5I2 reagents.

Exhaustive Chlorination as a Technique in the Analysis of Aromatic Hydrocarbons Academic Article