%0 Journal Article
%T Synthesis of Azidohydrin from Hura crepitans Seed Oil: A Renewable Resource for Oleochemical Industry and Sustainable Development
%A Adewale Adewuyi
%A Andrea G£¿pfert
%A Thomas Wolff
%A B. V. S. K. Rao
%A R. B. N. Prasad
%J ISRN Organic Chemistry
%D 2012
%R 10.5402/2012/873046
%X The replacement of petrochemicals by oleochemical feedstocks in many industrial and domestic applications has resulted in an increase in demand for biobased products and as such recognizing and increasing the benefits of using renewable materials. In line with this, the oil extracted from the seed of Hura crepitans was characterized by an iodine value of £¿g Iodine/100£¿g and a saponification number of £¿mg£¿KOH/g with the dominant fatty acid being C18:2 ( %). The epoxidised fatty acid methyl esters prepared from the oil were used to synthesise the azidohydrin with a yield of 91.20%. The progress of the reaction was monitored and confirmed using FTIR and NMR. This showed the seed oil of Hura crepitans as a renewable resource that can be used to make valuable industrial and domestic products. 1. Introduction Vicinal azidoalcohols are precursors of aminoalcohols, which are well known as ¦Â-blockers and present in various natural products and different bioactive compounds; vicinal azidoalcohols not only constitute components of biologically active natural products but also serve as essential intermediates in the synthesis of amino sugar [1¨C3], carboxylic nucleosides [4], lactams [5], oxazolines, and aminoalcohols [6]. Ring-opening reactions of epoxides with nucleophiles are very useful approach in organic synthesis for the preparation of functionalized oxygenated compounds. Epoxides are versatile intermediates in organic synthesis, and their reactions with a variety of reagents such as electrophiles, nucleophiles, acids, bases, reducing agents, and some oxidizing agents are widely studied [7]. The reaction with nucleophiles such as oxygen compounds [8¨C10], nitrogen compounds (amine and derivatives of amines, azide, nitrate, and isocyanate), halides, and various carbon nucleophiles [11, 12] has been performed in both organic and aqueous solvents. Oleochemicals are chemicals derived from plant and animal fats. They are analogous to petrochemicals derived from petroleum. The formation of basic oleochemical substances like fatty acids, fatty acid methyl esters (FAMEs), fatty alcohols, fatty amines, and glycerols is by various chemical and enzymatic reactions. In the last decade, the oleochemical industry has been growing steadily due to increased global demand for more environment-friendly products. This is because of oleochemicals¡¯ attractive traits such as being derived from renewable resources, nontoxic, and readily biodegradable. Oils and fats of plant and animal origin offer possibilities of providing industries with a wealth of reaction products which will be
%U http://www.hindawi.com/journals/isrn.organic.chemistry/2012/873046/