Ethanolysis products from Douglas fir Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/dv13zw53w

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  • Douglas fir bark fines which contained 74.8 percent of Klason lignin and 70.2 percent of one percent sodium hydroxide solubility and decayed Douglas fir wood which contained 53.9 percent of Klason lignin were subjected to ethanolysis. A slight modification of the Hibbert's ethanolysis procedure was used. The monomeric compounds present in the reaction products were then examined. Two fractions of ethyl ether soluble oil were obtained from both bark and wood samples, which were mixtures of monomeric compounds produced by the ethanolysis reaction. One, which was designated "PE" fraction, was obtained by an ether extraction of a tar-like water insoluble substance of the ethanolysis products, and the other one designated "LE" fraction was obtained by the ether extraction of a water solution of the water soluble ethanolysis product. Two dimensional paper partition chromatography of these ether soluble oils demonstrated the presence of 12 compounds in the bark "PE" fraction, four compounds in the bark "LE" fraction and nine compounds in the wood "LE" fraction. The wood "PE" fraction gave the same chromatogram as the wood "LE". In the wood "LE", the typical Hibbert's monomers, 1-ethoxy-1-guaiacyl-2-propanone, 2-ethoxy-1-guaiacyl-lpropanone, guaiacyl-acetone, vanilloyl-acetyle, vanillin, and vanillic acid were identified. Ethyl ferulate was isolated from the bark "PE", which was the only C₆-C₃, phenyl propane type compound obtained from the ethanolysis of the bark fines sample. Ethyl protocatechuate, protocatechuic acid, and vanillic acid were isolated from the bark "PE" and "LE". Ethyl vanillate was isolated from the bark "LE". Identification of the esters was confirmed by comparison with authentic samples prepared by synthesis. From these results, it was concluded that the major monomeric compounds which were produced by the ethanolysis reaction of the bark fines were ferulic acid, protocatechuic acid, and vanillic acid. This indicates that the building units of the bark phenolic acid molecule are different from those in the lignin from wood.
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