Synthesis of several single C₁₀, C₁₁, and C₁₂ chloroalkanes

Different chlorinated compounds with a chain length of C₁₀, C₁₁, and C₁₂ have been synthesized as single standards for the residue analysis of chlorinated paraffins. Two dichlorodecadienes, two tetrachlorodecenes, and two hexachlorodecanes could be isolated after stepwise chlorine addition to 1,5,9-decatriene. Through radicalic addition of CCl₄ to 1,5,9-decatriene, two tetrachloroundecadienes and two octachlorododecadienes were formed, which gave the corresponding octachloro-undecanes and decachlorododecanes after chlorine addition. Further chlorodecanes were obtained by HCl addition to dichlorodecadienes and tetrachlorodecenes. Elimination of one HCl from hexachlorodecanes yielded a mixture of several pentachlorodecene diastereoisomers and, after chlorination or hydrogenation of this mixture, a hexachlorodecene or a tetrachlorodecane respectively was isolated. Additionally, hydrogenation of tetrachlorodecenes and octachlorododecenes led also to the corresponding saturated chloro compounds. Furthermore, the number of compounds could be enlarged by the radical CCl₄ addition to 1,7-octadiene and 1,8-nonadiene, from which the corresponding octachlororodecane and octachloroundecane were obtained. The addition of one mole CCl₄ to 1,9-decadiene afforded a tetrachloroundecene, which reacted with chlorine to form hexachlorodecane.