Selective synthesis of triphenoxysilane by the reaction of metallic silicon with phenol using copper(I) chloride as the catalyst

Masaki Okamoto, Naoto Watanabe, Eiichi Suzuki, Yoshio Ono

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

When copper(1) chloride was used as a catalyst in the reaction of silicon with phenol, a high selectivity for triphenoxysilane (HSi(OPh)3) (94%) was obtained, the other product being tetraphenoxysilane (Si(OPh)4). Addition of a small amount of propyl chloride to the feed for poisoning metallic copper enhanced the selectivity for HSi(OPh)3 without affecting the rate of silicon consumption. This result indicates that HSi(OPh)3 is an exclusive primary product and that Si(OPh)4 is formed by the secondary reaction between HSi(OPh)3 and phenol. The reaction mechanism involving surface silylene intermediate is proposed for the formation of HSi(OPh)3 as the sole primary product. The intermediacy of surface silylene was confirmed by adding ethylene in the silicon-phenol reaction to give rise to the trapped product ethyldiphenoxysilane, obtained in a 5.8% selectivity.

Original languageEnglish
Pages (from-to)51-55
Number of pages5
JournalJournal of Organometallic Chemistry
Volume515
Issue number1-2
DOIs
Publication statusPublished - 1996 May 31
Externally publishedYes

Fingerprint

Silicon
Phenol
phenols
Phenols
chlorides
Copper
catalysts
copper
Catalysts
selectivity
silicon
synthesis
products
Poisoning
Chlorides
poisoning
Ethylene
ethylene
cuprous chloride

Keywords

  • Catalyst
  • Copper
  • Direct synthesis
  • Organosilane
  • Phenol
  • Silicon
  • Triphenoxysilane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Selective synthesis of triphenoxysilane by the reaction of metallic silicon with phenol using copper(I) chloride as the catalyst. / Okamoto, Masaki; Watanabe, Naoto; Suzuki, Eiichi; Ono, Yoshio.

In: Journal of Organometallic Chemistry, Vol. 515, No. 1-2, 31.05.1996, p. 51-55.

Research output: Contribution to journalArticle

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AU - Watanabe, Naoto

AU - Suzuki, Eiichi

AU - Ono, Yoshio

PY - 1996/5/31

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N2 - When copper(1) chloride was used as a catalyst in the reaction of silicon with phenol, a high selectivity for triphenoxysilane (HSi(OPh)3) (94%) was obtained, the other product being tetraphenoxysilane (Si(OPh)4). Addition of a small amount of propyl chloride to the feed for poisoning metallic copper enhanced the selectivity for HSi(OPh)3 without affecting the rate of silicon consumption. This result indicates that HSi(OPh)3 is an exclusive primary product and that Si(OPh)4 is formed by the secondary reaction between HSi(OPh)3 and phenol. The reaction mechanism involving surface silylene intermediate is proposed for the formation of HSi(OPh)3 as the sole primary product. The intermediacy of surface silylene was confirmed by adding ethylene in the silicon-phenol reaction to give rise to the trapped product ethyldiphenoxysilane, obtained in a 5.8% selectivity.

AB - When copper(1) chloride was used as a catalyst in the reaction of silicon with phenol, a high selectivity for triphenoxysilane (HSi(OPh)3) (94%) was obtained, the other product being tetraphenoxysilane (Si(OPh)4). Addition of a small amount of propyl chloride to the feed for poisoning metallic copper enhanced the selectivity for HSi(OPh)3 without affecting the rate of silicon consumption. This result indicates that HSi(OPh)3 is an exclusive primary product and that Si(OPh)4 is formed by the secondary reaction between HSi(OPh)3 and phenol. The reaction mechanism involving surface silylene intermediate is proposed for the formation of HSi(OPh)3 as the sole primary product. The intermediacy of surface silylene was confirmed by adding ethylene in the silicon-phenol reaction to give rise to the trapped product ethyldiphenoxysilane, obtained in a 5.8% selectivity.

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