Thermal polymerizations of alkali 4-(2-bromoethyl)benzoates in bulk

Fumihiko Akutsu, Mari Inoki, Koichi Shinoda, Takashi Susukida, Yoshio Kasashima, Tadashi Shimura, Masaomi Tsuchiya

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6 Citations (Scopus)


Thermal polymerizations of alkali 4-(2-bromoethyl)benzoates (2-BEBAs) were investigated. The polymerization of the lithium salt at 220 °C for 2 h under reduced pressure in bulk, followed by esterification, produced poly(methyl 4-vinylbenzoate), having a number-average molecular weight (M̄n) of 9500 in a 54% yield. Thus, elimination of hydrogen bromide to form a double bond occurred, followed by vinyl polymerization. In contrast, polymerization of the potassium salt at 200 °C for 2 h afforded poly(oxycarbonyl-1,4-phenylene-ethylene) (polyester 1), having an inherent viscosity of 0.19 dL g-1 in a 95% yield: i.e., polycondensation proceeded to afford the polyester. Reaction of the sodium salt at 220 °C for 2 h produced polyester 1 having M̄n of 4000 in a 28% yield as well as 4-vinylbenzoic acid in a 9% yield. In the reaction of the sodium salt, both polycondensation and double bond formation occurred. Thus, these polymerizations depended on the counter cations of 2-BEBAs.

Original languageEnglish
Pages (from-to)2055-2060
Number of pages6
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Issue number13
Publication statusPublished - 1999 Jul 1

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry


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