活性白土の触媒作用に関する研究 (第6報) : 高級モノアルキルフェノールの合成におけるo-, m-, p-異性体の生成比について
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In this paper the author studied on the composition of o-, m- and p-isomers of higher alkylphenols prepared by the reaction of phenol with some kinds of alcohols and an olefin, nonene, in the presence of Japanese acid clay. The reaction conditions were as follows; mol ratio of phenol to alcohol or olefin, 1.5/1.0; the quantity of clay added, 10% by weight for total amount of phenol and alcohol ; reaction time, 1.01.5 hr; reaction temp., 110180°C. Quantitative analysis of isomers was carried out by infrared method, neglecting the quantity of <I>m</I>-isomers. <BR>Under these conditions diallkyl phenols were scarcely formed. In some cases very small amount of <I>m</I>-isomer was formed but the main products were the mixtures of <I>o</I>- and <I>p</I>-mono-alkylphenols. In alkylatation of phenol with alochols of C<SUB>6</SUB> to C<SUB>12</SUB>, almost equal amounts of <I>o</I>-alkylphenol and <I>p</I>-isomer were formed, even in the alkylation of phenols with tert-alkyl group. In the order from cyclohexy-lalcohol to cetylalcohol, the formation of <I>p</I>-isomer increased except that in the case of benzyl alcohol <I>o</I>-isomer was predominant; with nonene, in comparison with alcohols, <I>p</I>-isomer was formed predo-minantly. <BR>The yields and the <I>o</I>-/<I>p</I>- ratios of produced mono-alkylphenols were as follows; 2-ethylbutylalcohol (55%, 1.0/1.3), 2-ethylhexylalcohol (52%, 1.0/1.4), <I>n</I>-octylalcohol (70%, 1.0/1.2), <I>n</I>-decylalcohol (69%, 1.0/1.1), <I>n</I>-dodecylalcohol (69%, 1.0/1.2), <I>n</I>-cetylalcohol (83%, 1.0/4.3), cyclohexylalcohol (49%, 1.0/1.8), benzylalcohol (78%, 1.5/1.0), nonene (80%, 1.0/10; 90%, 1.0/6.7 in case of mol ratio of phenol to nonene being 4.0; and 70%, 1.0/5.7, using sulfuric acid as a catalyst at 5860°C). <BR>Two samples of nonionic detergent prepared from ethylene oxide and two kinds of nonylphenols, one prepared and the other bought on the market, showed no difference in the interfacial tention of aq. solution and some other properties, despite some difference of the composition (the former contained 13% of <I>o</I>-isomer, and the lattter only 3.0%).
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