A novel synthesis of branched high-molecular-weight (C+40) long-chain alkanes

Hans Joachim Lehmler, Robert G. Bergosh, Mark S. Meier, Robert M.K. Carlson

Research output: Contribution to journalArticlepeer-review

3 Scopus citations


Many biological and geochemical questions remain concerning the structures, functions, and properties of naturally occurring high-molecular-weight (C40+) alkanes with various mid-chain alkylation patterns. Above C40, these alkanes are exceedingly difficult to separate and purify, and syntheses can be blocked by the low solubility of intermediates. To overcome these problems, a facile three-step synthesis employing the alkylation of 1,3-dithiane with a suitable a, v-dibromoalkane was developed. Bisalkylation of the bis(dithianyl)alkane intermediate with the appropriate 1-bromoalkane and subsequent desulfurization with Raney nickel furnished the desired long-chain alkane. Long-chain alkanes modified at mid-chain and/or symmetrically near the chain termini (or unmodified, i.e., long-chain α, ω-paraffins) are accessible by the selection of appropriate bromoalkanes. Nine mid-chain methylated (C38H78 to C53H108), one symmetrical terminal-chain dimethylated (C40H82), and fourlinear (C44H90 to C58H118) long-chain alkanes were synthesized by using this approach. High-temperature gas chromatography (HTGC) was found to have important advantages for evaluating the purity of the synthetic high-molecular-weight alkanes.

Original languageEnglish
Pages (from-to)523-531
Number of pages9
JournalBioscience, Biotechnology and Biochemistry
Issue number3
StatePublished - 2002


  • Bran-ched alkane
  • Dithiane
  • Linear alkane
  • Long-chain alkane

ASJC Scopus subject areas

  • General Medicine


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