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.

摘要

使用文献中报道的方法对植物种子油的叠氮化进行了重新研究，以重新检查在最终叠氮化的油中是否保留了对维持植物油产品的生物降解性至关重要的三酰基甘油主链。使用NH ₄ Cl作为催化剂，使NaN ₃与环氧化的短株腺病毒（EADBO）反应（方法A），得到酸解产物和含有三酰基甘油骨架的产物混合物。与NaN的EADBO的反应₃使用离子性液体，1-甲基咪唑鎓四氟硼酸盐（[HMIM] BF在水中₄ ^- ），作为催化剂（方法B），生成仅包含三酰基甘油骨架上的产物，同时用NaN的EADBO的反应的产物₃ 在DMF中，使用[HMIM] BF ₄ ^-催化剂（方法C），得到产量最高，但不包含任何三酰基甘油骨架。因此，方法B最适合于其叠合产品的环境友好性。现在通常可以使用方法B从植物油源中制备通常由石化产品制备的叠氮化合物，所述方法B用于制备可生物降解的邻位羟基甘油三酸酯，这在表面活性剂工业中非常通用。