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 language | English |
|---|---|
| Pages (from-to) | 2831-2836 |
| Number of pages | 6 |
| Journal | ACS Sustainable Chemistry and Engineering |
| Volume | 2 |
| Issue number | 12 |
| DOIs | |
| Publication status | Published - 2014 Dec 1 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Simple ring-closing metathesis approach for synthesis of PA11, 12, and 13 precursors from oleic acid
AU - Mudiyanselage, Ajith Yapa
AU - Viamajala, Sridhar
AU - Varanasi, Sasidhar
AU - Yamamoto, Kana
PY - 2014/12/1
Y1 - 2014/12/1
N2 - 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.
AB - 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.
KW - Green chemistry
KW - Nylon
KW - Nylon 12
KW - Olefin metathesis
KW - Oleic acid
KW - PA
KW - PA12
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=84928501334&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84928501334&partnerID=8YFLogxK
U2 - 10.1021/sc500599u
DO - 10.1021/sc500599u
M3 - Article
VL - 2
SP - 2831
EP - 2836
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
SN - 2168-0485
IS - 12
ER -