Studies on the synthesis of linear aliphatic compounds. Part. 3 The synthesis of paraffins with very long chains

Abstract

The approach derived in Part 2 has been modified to increase the purity and yield of intermediates. The C₁₂ starting materials have been doubled in chain length five times, and by using components of similar or different chain length in Wittig condensations ω-halogeno-acetals with 12n carbon atoms have been made up with n up to 32. They have been converted into paraffins with 102, 104, 150, 198, 246, 294, and 390 carbon atoms. Those paraffins with 150 or more carbon atoms show chain-folding in the crystalline state; this observation is contributing to the understanding of chain-folding behaviour long known in linear polyethylene but hitherto unknown in essentially pure paraffins.