Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 2/9/2011
Publication Date: 9/27/2011
Citation: Biswas, A., Sharma, B.K., Vermillion, K., Willett, J.L., Cheng, H.N. 2011. Synethesis of cyclic ketal from soybean oil and fatty esters. Journal of Agricultural and Food Chemistry. 59(7):3066-3070. Interpretive Summary: In this research, we discovered a new, environmentally-friendly, fast method to make acetonido vegetable oil. Accetonide-containing oils have possible applications as ingredients in lubricants, coatings, cosmetics, biodiesel fuel, agricultural chemicals, spandex fibers, antioxidants and pharmaceuticals. This method produced no byproducts and the inexpensive iron catalyst was filtered off. This discovery will benefit industrial chemical manufacturers, among others, because it produces a cheap, environmentally friendly material that requires less energy usage.
Technical Abstract: In this work we have shown a facile and environmentally friendly reaction to form a cyclic ketal out of soybean oil, methyl soyate, methyl linoleate, and methyl oleate. There are many advantages of this reaction. First, the ketal reaction produces a branched fatty acid moiety and is reversible. Secondly, we use ferric chloride (a Lewis acid), and it is less likely to cause hydrolysis of the ester or glyceride. Ferric chloride is also not soluble in water and can be more easily separated and (if needed) recycled. Thirdly, acetone is cheap and more environmentally friendly. Finally, we use room temperature for the reaction, resulting in less energy usage.