Toward Sustainable Synthesis of PA12 (Nylon-12) Precursor from Oleic Acid Using Ring-Closing Metathesis

Godwin Ameh Abel, Sridhar Viamajala, Sasidhar Varanasi, Kana Yamamoto

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The efficient reaction conditions for ring-closing metathesis of homoallyloleamide (2) for the synthesis of PA12 (Nylon-12) precursor (4) are presented. Systematic screening of a series of commercially available metathesis catalysts identified a catalyst that promotes the reaction at low temperature (60 °C), enabling use of nonhalogenated solvents, ethyl acetate and hexanes. The catalyst was adsorbed on mesoporous silica gel to aid its postreaction recovery and reuse, which was demonstrated in hexanes up to three cycles without significant loss of reaction conversion (>90%). The identification of reaction-compatible green solvents as well as the demonstration of the potential for recycling of the supported catalyst are steps further toward establishing environmentally sustainable production of the polyamide precursors from oleic acid.

Original languageEnglish
Pages (from-to)5703-5710
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume4
Issue number10
DOIs
Publication statusPublished - 2016 Oct 3
Externally publishedYes

Fingerprint

Oleic acid
Oleic Acid
catalyst
Hexanes
Hexane
Catalysts
acid
Nylons
Silica Gel
Silica gel
Polyamides
Catalyst supports
Recycling
Screening
Demonstrations
Recovery
acetate
recycling
gel
silica

Keywords

  • Fatty acids
  • Green chemistry
  • Nylon
  • Olefin metathesis
  • Oleic acid
  • Polyamide
  • Ruthenium catalyst

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

Cite this

Toward Sustainable Synthesis of PA12 (Nylon-12) Precursor from Oleic Acid Using Ring-Closing Metathesis. / Abel, Godwin Ameh; Viamajala, Sridhar; Varanasi, Sasidhar; Yamamoto, Kana.

In: ACS Sustainable Chemistry and Engineering, Vol. 4, No. 10, 03.10.2016, p. 5703-5710.

Research output: Contribution to journalArticle

Abel, Godwin Ameh ; Viamajala, Sridhar ; Varanasi, Sasidhar ; Yamamoto, Kana. / Toward Sustainable Synthesis of PA12 (Nylon-12) Precursor from Oleic Acid Using Ring-Closing Metathesis. In: ACS Sustainable Chemistry and Engineering. 2016 ; Vol. 4, No. 10. pp. 5703-5710.
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