Polymerization of diphenyl disulfide by the S-S bond cleavage with a Lewis acid. A novel preparation route to poly(p-phenylene sulfide)

Eishun Tsuchida, Kimihisa Yamamoto, Hiroyuki Nishide, Shu Yoshida, Mitsutoshi Jikei

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Abstract

Poly (p-phenylene sulfide) (PPS) is efficiently and conveniently produced by a cationic and oxidative polymerization. Diphenyl disulfide is allowed to react with a Lewis acid such as antimony pentachloride at room temperature and is polymerized to PPS. The polymer is isolated as a white powder, whose 1,4 structure is confirmed by IR. Phenylbis(phenylthio)sulfonium ion acts as an active species, which is formed by oxidation of the S-S bond of diphenyl disulfide with the Lewis acid, and is electrophilically substituted on the phenyl ring. The polymerization mechanism is discussed and compared to a model reaction using dimethyl disulfide.

Original languageEnglish
Pages (from-to)2101-2106
Number of pages6
JournalMacromolecules
Volume23
Issue number8
Publication statusPublished - 1990 Jan 1

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Lewis Acids
Sulfides
Polymerization
Acids
Antimony
Powders
Polymers
Ions
Oxidation
Temperature
diphenyl disulfide
poly-para-phenylene
antimony pentachloride
dimethyl disulfide

ASJC Scopus subject areas

  • Materials Chemistry

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Polymerization of diphenyl disulfide by the S-S bond cleavage with a Lewis acid. A novel preparation route to poly(p-phenylene sulfide). / Tsuchida, Eishun; Yamamoto, Kimihisa; Nishide, Hiroyuki; Yoshida, Shu; Jikei, Mitsutoshi.

In: Macromolecules, Vol. 23, No. 8, 01.01.1990, p. 2101-2106.

Research output: Contribution to journalArticle

Tsuchida, Eishun ; Yamamoto, Kimihisa ; Nishide, Hiroyuki ; Yoshida, Shu ; Jikei, Mitsutoshi. / Polymerization of diphenyl disulfide by the S-S bond cleavage with a Lewis acid. A novel preparation route to poly(p-phenylene sulfide). In: Macromolecules. 1990 ; Vol. 23, No. 8. pp. 2101-2106.
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