Preparation of alkenyl succinic anhydrides from vegetable oil FAME

Abstract : Sunflower oil and oleic motif‐enriched sunflower oil methyl esters were used to prepare alkenyl succinic anhydrides. A classic batch reactor was selected to carry out the synthesis. The range in which the temperature, reaction time, and molar ratio between the number of moles of maleic anhydride and the equivalent number of double bonds present in the unsaturated vegetable oil methyl esters (the most influential factors in the process) varied was determined in a preliminary study. A secondorder Doehlert uniform network design was used to investigate the influence of the temperature and molar ratio for all the methyl esters on the yield of alkenyl succinic anhydride from methyl oleate, the conversion of methyl oleate, the formation of side reaction products, the Gardner color of the product, and viscosity. The optimal reaction conditions for obtaining the maximal yield (around 95%) of alkenyl succinic anhydride from methyl oleate were 235°C, a molar ratio of 1.5, and a reaction lasting 8 h. However, the products synthesized under these conditions showed high viscosity (215 cP), a very dark color (18+ Gardner color), and a high content of undesirable side products (4%), which hindered their direct industrial use. The increase in the product viscosity was probably due to the formation of side reaction products. A molar ratio of less than 1.5 led to a less viscous product, although with a lower alkenyl succinic anhydride content.
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Joaquín Quesada, Marie Morard, Carlos Vaca-Garcia, Marie-Elisabeth Borredon. Preparation of alkenyl succinic anhydrides from vegetable oil FAME. Journal of the American Oil Chemists' Society, Springer Verlag, 2003, 80 (3), pp.281-286. ⟨10.1007/s11746-003-0690-4⟩. ⟨hal-02080809⟩

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