In situ alkaline transesterification: An effective method for the production of fatty acid esters from vegetable oils

The production of simple alkyl FA esters by direct alkali-catalyzed in situ transesterification of the acylglycerols (AG) in soybeans was examined. Initial experiments demonstrated that the lipid in commercially produced soy flakes was readily transesterified during agitation at 60 degreesC in sealed containers of alcoholic NaOH. Methyl, ethyl, and isopropyl alcohols readily participated in the reaction, suggesting that the phenomenon is a general one. Statistical experimental design methods and response surface regression analysis were used to optimize reaction conditions, using methanol as alcohol. At 60 degreesC, the highest yields of methyl ester with minimal contamination by FFA and AG were predicted at a molar ratio of methanol/AG/NaOH of 226:1:1.6 with an approximately 8-h incubation. An increase in the amount of methanol, coupled with a reduced alkali concentration, also gave high ester yields with low FFA and AG contamination. The reaction also proceeded well at 23 degreesC (room temperature), giving higher predicted ester yields than at 60 degreesC. At room temperature, maximal esterification was predicted at a molar ratio of 543:1:2.0 for methanol/AG/NaOH, again in 8 h. Of the lipid in soy flakes, 95% was removed under such conditions. The amount of FAME recovered after in situ transesterification corresponded to 84% of this solubilized lipid. Given the 95% removal of lipid from the soy flakes and an 84% efficiency of conversion of this solubilized lipid to FAME, one calculates an overall transesterification efficiency of 80%. The FAME fraction contained only 0.72% (mass basis) FFA and no AG. Of the glycerol released by transesterification, 93% was located in the alcoholic ester phase and 7% was on the post-transesterification flakes.