Telomerization

This article is about the polymerization reaction. For the DNA component, see telomere.

Telomerization is a reaction that produces a particular kind of oligomer with two distinct end groups. The oligomer is called a telomer.[1] Some telomerizations proceed by radical pathways, many do not. A generic equation is:

where M is the monomer, and A and B are the end groups, and n is the degree of polymerization.

One example is the coupled dimerization and hydroesterification of buta-1,3-diene. This step produces a doubly unsaturated C9-ester:[2]

2 CH2=CH-CH=CH2 + CO + CH3OH → CH2=CH(CH2)3CH=CHCH2CO2CH3

The monomer in this reaction is butadiene, the degree of polymerization is 2, and the end groups are vinyl and the carboxy methyl (CO2CH3). This and several related reactions proceed with palladium catalysts.[3] Many telomerizations are used in industrial chemistry.[4]

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "telomerization". doi:10.1351/goldbook.T06260
  2. ^ J. Grub; E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2. ISBN 978-3527306732.
  3. ^ Kiss, Gabor (2001). "Palladium-Catalyzed Reppe Carbonylation". Chemical Reviews. 101 (11): 3435–3456. doi:10.1021/cr010328q. PMID 11840990.
  4. ^ Lehmler, HJ (Mar 2005). "Synthesis of environmentally relevant fluorinated surfactants—a review". Chemosphere. 58 (11): 1471–96. Bibcode:2005Chmsp..58.1471L. doi:10.1016/j.chemosphere.2004.11.078. PMID 15694468.