Graduate Thesis Or Dissertation

 

The separation and purification of the fatty and hydroxy fatty acids of white fir bark wax Public Deposited

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  • This investigation was undertaken to develop a procedure by which the fatty acids could be separated from the hydroxy fatty acids of bark waxes. The specific hexane-insoluble, benzene-soluble wax used in this research was obtained from the bark of white fir, Abias concolor, (Lindl. and Gord.). The acids were removed from the other components of the wax by a process of saponification, then acidification, followed by extraction with benzene, then hexane. These crystals were resaponified, extracted with hot benzene, and then acidified. This procedure resulted in two crude free acid fractions, I and II. Then separately, fractions I and II were subjected to a purification procedure which was designed to yield pure acids. This procedure consisted first of forming the methyl esters of the crude free acid mixture and crystallizing them from hexane. These methyl ester fractions were then saponi-fled and again crystallized from hexane. Some of the resulting acid fractions were then combined on the basis of simolar melting points. These fractions were then subjected to an acetylation procedure which would attach an acetate grouping to any hydroxyl groups which were present. In this way the hydroxy acids could be separated from the fatty acids by the relative solubility of the acetates and acids in hexane. In this solvent the acetates were the more coluble components. These acetate and acid fractions were then saponified using a quantitative procedure, so that the approximate molecular weight of the fraction could be obtained. At this point after recrystallization from hexane, the fraction was considered to be pure. However, a gas-liquid chromatography analysis showed that the samples were not pure but contained up to 30% of contaminating acids. But despite this fact, the major acid was separated and had the following properties: melting point 37.5- 89°C., methyl ester melting point 70-74°C., apparently no hydroxyl group present, and the approximate molecular weight of the methyl ester 345.3. This acid was obtained from the crude free acid fraction I. One other acid from this same fraction showed these definite properties: melting point 88.5- 90°C., methyl ester melting point 71-72 °C., acetate melting point 72- 74°C., and approximate molecular weight of the acetate 400. There were other acids obtained from this Fraction I, but they were present in small quantities and were not completely characterized.
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