Simple ring-closing metathesis approach for synthesis of PA11, 12, and 13 precursors from oleic acid

Ajith Yapa Mudiyanselage, Sridhar Viamajala, Sasidhar Varanasi, Kana Yamamoto

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Due to the concerns over limited fossil resources and increasing CO2 emissions, there is a strong interest in use of renewable resources in production of valuable synthetic materials. PA11, 12, and 13, more commonly known as Nylon, are high-strength polymers that find use in various industrial sectors. They are traditionally produced from petroleum-derived material or exotic fatty acids using reaction sequences that involve 4-6 steps. Herein we report a simple three-step synthesis of these polyamide precursors from oleic acid, an abundant natural fatty acid available from common plant sources as well as oleaginous micro-organisms such as microalgae. This approach represents the first example where ring-closing metathesis was used for the key C-C bond forming step, featuring introduction of amine functionality required in the final product. Our versatile approach allows preparation of nylon precursors of various chain-lengths from a single starting material for economical and sustainable production of these polymers.

Original languageEnglish
Pages (from-to)2831-2836
Number of pages6
JournalACS Sustainable Chemistry and Engineering
Volume2
Issue number12
DOIs
Publication statusPublished - 2014 Dec 1
Externally publishedYes

Keywords

  • Green chemistry
  • Nylon
  • Nylon 12
  • Olefin metathesis
  • Oleic acid
  • PA
  • PA12
  • Synthetic methods

ASJC Scopus subject areas

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

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