Some methods used for the azidation of plant seed oils reported in literature were investigated with a view to seeing if they support the retention of the triacylglycerol backbone in the final azidated oil since retention of the triacylglycerol backbone is important for maintaining biodegradability in the plant oil products. Reaction of epoxidised Adenopus breviflorus benth oil (EADBO) with NaN3 in presence of NH4Cl as catalyst (Method A) gave mixture of products with some containing triglyceride structures and some acidolysis products while reaction of EADBO with NaN3 in water and in presence of an ionic liquid, 1-methyl imidazolium tetrafluoroborate as catalyst (Method B) yielded a product containing triglyceride structure. The reaction of EADBO with NaN3 in DMF and in presence of 1-methyl imidazolium tetrafluoroborate as catalyst (Method C) however yielded a product with no triglyceride structure. In terms of environmental friendliness, Method B is therefore better than Method A and Method C is least. However the percentage azidation as revealed by the nitrogen content (elemental analysis) and azide functionality showed that it was highest in the product of Method C followed by that obtained by Method A and then Method B. These extents of azidation may be ascribed to presence or absence of steric hindrance due to presence or absence of the triglyceride structure.

Synthesis and Properties of Azidated Adenopus breviflorus benth seed oil

256th National Meeting (2018)

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