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

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 (6.8 mm) with Grubbs second generation catalyst (0.3 mm) at 40-45 °C for 36 h. 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.