Synthesis and characterization of azidated Adenopus breviflorus benth seed oil

Abstract

Azidation of plant seed oils was re-investigated using methods reported in the literature, to re-examine if triacylglycerol backbone, important for maintaining biodegradability in plant oil products is retained in the final azidated oil. Reaction of NaN3 with epoxidized Adenopus breviflorus oil (EADBO) using NH4Cl as catalyst (Method A), gave acidolysis products and mixture of products containing triacylglycerol backbone. Reaction of EADBO with NaN3 in water using an ionic liquid, 1-methyl imidazolium tetrafluoroborate ([Hmim]BF4−), as catalyst (Method B), generated a product containing only triacylglycerol backbone while product of reaction of EADBO with NaN3 in DMF, using [Hmim]BF4− catalyst (Method C) gave highest yield but did not contain any triacylglycerol backbone. Thus, Method B was best for environmentally friendliness of its azidated product. Azido compounds generally prepared from petrochemicals may now be prepared from plant oil source using method B for preparation of biodegradable vicinal hydroxyl triglyceride which is very versatile in surfactant industries.