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Publication Information

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Title: Formaldehyde condensation products of model phenols for conifer bark tannins

Author: Hemingway, Richard W.; McGraw, Gerald W.;

Date: 1978

Source: Journal of Liquid Chromatography, Vol. 1(2): 163-179

Publication Series: Miscellaneous Publication

Description: Gel permeation chromatography of the condensation products of phenols and formaldehyde proved effective in understanding the reactions of condensed tannins with formaldehyde. Rates of condensation of phloroglucinols, resorcinols, catechols, (+)catechins, and (-)epicatechin were examined to determine if methylol-tannins from southern pine bark could be prepared as resin intermediates. The phloroglucinols (models for the A-ring of pine bark tannins) were so much more reactive than were the resorcinols (models for the a-ring of wattle tannins), that preparation of methylol-tannins from pine bark tannins seems unlikely even though this approach has been applied succesfully to synthesis of resins from wattle tannins. The methylol content of catechin-formaldehyde condensation products was very low. The catechol B-ring was unreactive under conditions in which condensations of pine bark tannins could be controlled. although there is much less steric hindrance of the a-ring of (-)epicatechin than of (+)catechin, differences in the rates of condensation of these isomers were nont detected. GPC and H-NMR spectra of (+)catechin condensation products showed that a dimer formed rapidly and that further condensation occurred more slowly.

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Hemingway, Richard W.; McGraw, Gerald W. 1978. Formaldehyde condensation products of model phenols for conifer bark tannins. Journal of Liquid Chromatography, Vol. 1(2): 163-179


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