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

13 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

Fingerprint

Oleic acid
Nylons
Oleic Acid
fatty acid
polymer
Fatty acids
acid
Polymers
renewable resource
Fatty Acids
petroleum
Petroleum
fossil
Chain length
Polyamides
Amines
resource
Crude oil
material
amine

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

Cite this

Simple ring-closing metathesis approach for synthesis of PA11, 12, and 13 precursors from oleic acid. / Mudiyanselage, Ajith Yapa; Viamajala, Sridhar; Varanasi, Sasidhar; Yamamoto, Kana.

In: ACS Sustainable Chemistry and Engineering, Vol. 2, No. 12, 01.12.2014, p. 2831-2836.

Research output: Contribution to journalArticle

Mudiyanselage, Ajith Yapa ; Viamajala, Sridhar ; Varanasi, Sasidhar ; Yamamoto, Kana. / Simple ring-closing metathesis approach for synthesis of PA11, 12, and 13 precursors from oleic acid. In: ACS Sustainable Chemistry and Engineering. 2014 ; Vol. 2, No. 12. pp. 2831-2836.
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