A novel synthesis of branched high-molecular-weight (C40+) long-chain alkanes

Hans-Joachim Lehmler; Robert G Bergosh; Mark S Meier; Robert M K Carlson

doi:10.1271/bbb.66.523

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A novel synthesis of branched high-molecular-weight (C40+) long-chain alkanes

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A novel synthesis of branched high-molecular-weight (C40+) long-chain alkanes

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

Bioscience, biotechnology, and biochemistry, Vol.66(3), pp.523-531

03/2002

DOI: 10.1271/bbb.66.523

PMID: 12005044

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Abstract

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 alpha,omega-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 n-paraffins) are accessible by the selection of appropriate bromoalkanes. Nine mid-chain methylated (C38H78 to C53H108), one symmetrical terminal-chain dimethylated (C40H82), and four linear (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.

Indicators and Reagents

Alkanes - chemical synthesis

Chromatography, Gas

Alkanes - chemistry

Alkylation

Sulfur - chemistry

Details

Title: Subtitle: A novel synthesis of branched high-molecular-weight (C40+) long-chain alkanes
Creators: Hans-Joachim Lehmler - Graduate Center for Toxicology, University of Kentucky, Lexington 40536, USA. hjlehm1@uky.edu
Robert G Bergosh
Mark S Meier
Robert M K Carlson
Resource Type: Journal article
Publication Details: Bioscience, biotechnology, and biochemistry, Vol.66(3), pp.523-531
DOI: 10.1271/bbb.66.523
PMID: 12005044
NLM abbreviation: Biosci Biotechnol Biochem
ISSN: 0916-8451
eISSN: 1347-6947
Publisher: England
Language: English
Date published: 03/2002
Academic Unit: Occupational and Environmental Health; Iowa Neuroscience Institute
Record Identifier: 9984000927102771

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