Poly(p-phenylene methylene)

Structure of poly(p-phenylene methylene)

Poly(p-phenylene methylene) is an organic polymer with the formula (C6H4CH2)n.[1] In the simplest formulation, it consists of 1,4-phenylene rings linked by methylene groups. It however likely consists of various linkages, in addition to the 1,4 motif. Samples are amorphous and colorless. It is also known as polybenzyl.

Also called poly(benzyl), it was first observed by Friedel and Crafts who treated benzyl chloride with aluminium trichloride:[2].

n C6H5CH2Cl → (C6H4CH2)n + n HCl

It also arises by acid-catalyzed dehydration of benzyl alcoholl:

n C6H5CH2OH → (C6H4CH2)n + n H2O

Because the reaction is highly exothermic, safety regulations warn against heating bulk benzyl alcohol.

A more modern route entails acid-catalyzed polymerization from tribenzylborate.[3]


References

  1. ↑ Brühne, Friedrich; Wright, Elaine (2000). "Benzyl Alcohol". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a04_001. ISBN 978-3-527-30385-4.
  2. ↑ Friedel, C.; Crafts, C. M. (1885). "Action du chlorure de benzyle sur le sulfure de carbone en préesence du chlorure d'aluminium". Bull. Soc. Chim. 43: 53.
  3. ↑ Gunes, Deniz; Yagci, Yusuf; Bicak, Niyazi (2010). "Synthesis of Soluble Poly( p -phenylene methylene) from Tribenzylborate by Acid-Catalyzed Polymerization". Macromolecules. 43 (19): 7993–7997. Bibcode:2010MaMol..43.7993G. doi:10.1021/ma1008435.
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