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Metathesis of 9-octadecenoic acid methyl ester: diversity and mechanism of product formation at various Grubbs’ catalyst concentrations
Yelchuri Vyshnavi (1)
, Rachapudi Badari Narayana Prasad (2) , Mallampalli Sri Lakshmi Karuna (3,*) (1) Centre for Lipid Research, Council of Scientific and Industrial Research, Indian Institute of Chemical Technology, Hyderabad 500007, India
(2) Centre for Lipid Research, Council of Scientific and Industrial Research, Indian Institute of Chemical Technology, Hyderabad 500007, India
(3) Centre for Lipid Research, Council of Scientific and Industrial Research, Indian Institute of Chemical Technology, Hyderabad 500007, India
(*) Corresponding Author
Received: 02 Feb 2015, Accepted: 25 Apr 2015, Published: 30 Sep 2015
Abstract
Self-metathesis of 9-octadecenoic acid methyl ester was carried out with varying the concentration of Grubbs’ second generation catalyst from 0.03 mmol to 0.18 mmol at 40-45 °C for 36 h. Only two products (9-octadecene 30%, and dimethyl-9-octadecene-dienoate 23%) resulted when 0.06 mmol of catalyst was employed, while at other concentrations four metathesized products were observed. 9-Octadecene generated at 0.03, 0.06 and 0.12 mmol completely disappeared and dimethyl-9-octadecene-dienoate (64%) was observed in major amounts at 0.18 mmol concentration.
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DOI: 10.5155/eurjchem.6.3.275-278.1250
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Citations
[1]. James W. Herndon
The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015
Coordination Chemistry Reviews 329, 53, 2016
DOI: 10.1016/j.ccr.2016.08.007
[2]. Vyshnavi Yelchuri, K Srikanth, R B N Prasad, M S L Karuna
Olefin metathesis of fatty acids and vegetable oils
Journal of Chemical Sciences 131(5), , 2019
DOI: 10.1007/s12039-019-1615-8
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