Synthesis and characterization of azidated Adenopus breviflorus benth seed oil

• Published in: Green chemistry letters and reviews Vol. 13; no. 2; pp. 117 - 128
• Main Authors: Akintayo Emmanuel, T., Akintayo Cecilia, O., Oluwaleye, I. O., Ajaja, O., Beuermann, S.
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis 02.04.2020; Taylor & Francis Ltd; Taylor & Francis Group
• Subjects: Adenopus breviflorus benth oil; Ammonium chloride; azidation; Backbone; Biodegradability; Biodegradation; Catalysts; ionic liquid; Ionic liquids; Oils & fats; Petrochemicals; Sodium azide; Sodium azides; Triglycerides
• ISSN: 1751-8253; 1751-7192
• DOI: 10.1080/17518253.2020.1737251

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 NaN 3 with epoxidized Adenopus breviflorus oil (EADBO) using NH 4 Cl as catalyst (Method A), gave acidolysis products and mixture of products containing triacylglycerol backbone. Reaction of EADBO with NaN 3 in water using an ionic liquid, 1-methyl imidazolium tetrafluoroborate ([Hmim]BF 4 − ), as catalyst (Method B), generated a product containing only triacylglycerol backbone while product of reaction of EADBO with NaN 3 in DMF, using [Hmim]BF 4 − 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.