Epichlorohydrin coupling reactions with wood

Abstract

Properties of wood can be improved by reacting chemicals with hydroxyl groups of wood cell wall polymers. To achieve this improvement in wood properties, bioactive compounds containing hydroxyl groups, such as pentachlorophenol, 3,5-dimethyl phenol, and 2-naphthol, can be reacted with epichlorohydrin to give corresponding glycidyl ethers. The new epoxide formed during this reaction can be used to bond bioactive compounds to wood. This bonding may result in improved wood properties. The objective of this study was to develop a simple procedure for synthesizing glycidyl ethers. The alcohol was reacted with epichlorohydrin and a catalyst and monitored by thin-layer chromatography. Shortwave ultraviolet light was used to detect spots. Resulting products were analyzed for carbon, hydrogen, and in one case, chlorine. Reaction of pentachlorophenol with epichlorohydrin formed only one enantiomeric glycidyl ether, whereas reaction of 3,5-dimethyl phenol with epichlorohydrin led to two enantiomeric glycidyl ethers in a 1 to 3 ratio. Reaction of 2-naphthol with epichlorohydrin also led to two enantoimeric glycidyl ethers in equal amounts. In future research, these glycidyl ethers will be reacted with wood, and their toxicity to wood-destroying fungi in bonded form will be determined.

DOI: 10.1007/BF00195285

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Cite this paper

@article{Rowell2004EpichlorohydrinCR, title={Epichlorohydrin coupling reactions with wood}, author={Roger M. Rowell and Gen Chun Chen}, journal={Wood Science and Technology}, year={2004}, volume={28}, pages={371-376} }