Formation of Cyclic Oligomers from <I>p</I>-<I>t</I>-Butylphenol and Formaldehyde

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  • NAKAMOTO Yoshiaki
    Department of Industrial Chemistry, Faculty of Technology, Kanazawa University
  • ISHIDA Shin-ichiro
    Department of Industrial Chemistry, Faculty of Technology, Kanazawa University

Bibliographic Information

Other Title
  • <I>p</I>-<I>t</I>-ブチルフェノール・ホルムアルデヒド系環状オリゴマーの生成反応

Description

The KOH catalyzed reactions of p-t-butylphenol (BP) with paraformaldehyde in xylene have investigated in detail under various reaction conditions. Three kinds of cyclic oligomers were formed together with linear oligomers, and these could be identified to be cyclic octamer and hexamer linked only by methylene linkages and cyclic tetramer which was composed of three methylene linkages and one dimethylene ether linkage, respectively.<BR>The yield and distribution of the oligomers in the product depended on the amount of KOH remarkably. The yield of cyclic oligomers was maximum and the main product was octamer when the molar ratio of KOH to BP is equal to 0.2, and decrease of the ratio resulted in the increase of proportion of tetramer in product.<BR>When the molar ratio is above 0.5, only linear oligomer was obtained. 2, 6-Bis (hydroxymethyl) -4-t-butylphenol and BP-linear oligomer were treated with KOH in xylene to give the same cyclic oligomers.<BR>The cyclization was found to occur in nonpolar solvents such as xylene, toluene and heptane. The mechanism of formation of cyclic oligomers are also discussed.

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