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 language | English |
|---|---|
| Pages (from-to) | 5703-5710 |
| Number of pages | 8 |
| Journal | ACS Sustainable Chemistry and Engineering |
| Volume | 4 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 2016 Oct 3 |
| Externally published | Yes |
Fingerprint
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 journal › Article
}
TY - JOUR
T1 - Toward Sustainable Synthesis of PA12 (Nylon-12) Precursor from Oleic Acid Using Ring-Closing Metathesis
AU - Abel, Godwin Ameh
AU - Viamajala, Sridhar
AU - Varanasi, Sasidhar
AU - Yamamoto, Kana
PY - 2016/10/3
Y1 - 2016/10/3
N2 - 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.
AB - 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.
KW - Fatty acids
KW - Green chemistry
KW - Nylon
KW - Olefin metathesis
KW - Oleic acid
KW - Polyamide
KW - Ruthenium catalyst
UR - http://www.scopus.com/inward/record.url?scp=84989909891&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84989909891&partnerID=8YFLogxK
U2 - 10.1021/acssuschemeng.6b01648
DO - 10.1021/acssuschemeng.6b01648
M3 - Article
VL - 4
SP - 5703
EP - 5710
JO - ACS Sustainable Chemistry and Engineering
JF - ACS Sustainable Chemistry and Engineering
SN - 2168-0485
IS - 10
ER -