Synthesis and characterization of azidated Adenopus breviflorus benth seed oil

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 (EA...

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Bibliographic Details
Published in:Green chemistry letters and reviews 2020-04, Vol.13 (2), p.117-128
Main Authors: Akintayo Emmanuel, T., Akintayo Cecilia, O., Oluwaleye, I. O., Ajaja, O., Beuermann, S.
Format: Article
Language:English
Subjects:
Adenopus breviflorus benth oil
Ammonium chloride
azidation
Backbone
Biodegradability
Biodegradation
Catalysts
ionic liquid
Ionic liquids
Oils & fats
Petrochemicals
Sodium azide
Sodium azides
Triglycerides
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Summary: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.
ISSN:1751-8253
1751-7192
DOI:10.1080/17518253.2020.1737251