Metathesis of tobacco fatty acid methyl esters: Generation of industrially important platform chemicals

•Self-metathesis in unsaturated rich tobacco (Nicotiana tabacum, 82.2% unsaturation) fatty acid methyl esters was performed using Grubbs second generation catalyst.•9-octadecene (24%), a major hydrocarbon, lube-range oil intermediate was observed.•Cyclic hydrocarbon, namely cyclodecyclododecene was...

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Bibliographic Details
Published in:Industrial crops and products 2013-10, Vol.50, p.701-706
Main Authors: Vyshnavi, Yelchuri, Prasad, Rachapudi B.N., Karuna, Mallampalli S.L.
Format: Article
Language:English
Subjects:
esters
Grubbs second generation catalyst
hydrocarbons
Metathesis
Nicotiana tabacum
Non-edible oils
oleic acid
Platform chemicals
polymers
tobacco
Tobacco methyl esters
vegetable oil
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Summary:•Self-metathesis in unsaturated rich tobacco (Nicotiana tabacum, 82.2% unsaturation) fatty acid methyl esters was performed using Grubbs second generation catalyst.•9-octadecene (24%), a major hydrocarbon, lube-range oil intermediate was observed.•Cyclic hydrocarbon, namely cyclodecyclododecene was also observed in good amounts (19%).•The study discusses the reaction mechanism involved in the formation of metathesized products. Self-methathesis of vegetable oil based unsaturated fatty acids provide a renewable and convenient route for the preparation of a number of platform chemicals useful for the production of polymers, biolubricants and other industrial products. The present study is focused on the use of the unsaturated non-edible oil methyl esters of tobacco (Nicotiana tabacum 82.2%) self- metathesis. Metathesis was carried out reacting equimolar quantities of fatty acid methyl esters (6.8mm) with Grubbs second generation catalyst (0.3mm) at 40–45°C for 36h. The metathesized products were characterized using GC and GC–MS analysis. Self-metathesis of the tobacco methyl esters resulted in the formation of hydrocarbons, of which 9-octadecene (24%) and a cyclodecacyclododecene (19%) were found to be major. In addition 9-octadecenoic acid methyl ester (17%) and 9,12-octadecadienoic acid methyl esters (11%) were also observed. The study also discusses the molecules involved in the formation of the above intermediates which are useful for the preparation of a number of industrial products.
ISSN:0926-6690
1872-633X
DOI:10.1016/j.indcrop.2013.08.020