- Alkylation of Phenol by 1-Dodecene and 1-Decanol. A Literature Correction
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A recent literature report that 1-dodecene reacts with phenol in the presence of sulfated zirconium oxide (superacid), or 1-dodecanol with phenol in the presence of H-Mordenite (zeolite), to afford mostly para-substituted alkylphenols has been shown to be incorrect.The product with zirconium is a mixture of ortho/para isomers (ca. 50-65/50-35), and not the exclusive para isomer as reported.The major product in the case of zeolite catalysis is the o-alkylphenol, with a high degree of end attachment, and not the predominantly claimed para isomers.The selectivity obtained with H-Mordenite during alkylation of phenol differs from the a lkylation of alkylbenzenes and anisole, and is best explained on the basis of a surface catalysis phenomenon.
- Campbell, Curt B.,Onopchenko, Anatoli,Santilli, Donald S.
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p. 3665 - 3669
(2007/10/02)
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- Equilibria for the isomerization of (secondary-alkyl)phenols and cyclohexylphenols
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Equilibria of a series of isomerizations and trans-alkylations of alkylphenols have been investigated in the liquid phase over a wide range of temperatures.Equilibria of isomerizations connected with the displacement of a substituent on a benzene nucleus were studied for secondary-butyl, -amyl, -hexyl, and cyclohexyl-phenols, and di-(secondary-butyl)phenols.Equilibria of positional isomerization connected with the displacement of an oxyphenyl radical in an alkyl chain were investigated for oxyphenyl-pentanes, -hexanes, -octanes, and -decanes.Trans-alkylation was investigated for di- and tri-(secondary-butyl)phenols.Values of ΔrH0m and ΔrS0m were found for all investigated reactions.An analysis was made of the thermodynamic quantities for the reactions.Enthalpies of formation of isopropylphenols (IPP) in the gaseous state were calculated.The values of ΔfH0m/(kJ * mol-1) were found at 298.15 K: o-IPP, -(175.3 +/- 2.4); p-IPP, -(175.3 +/- 2.4); m-IPP, -(175.3 +/-2.4); 2,4-di-IPP, -(254.1 +/- 2.8); 2,5-di-IPP, -(254.1 +/- 2.8); 2,6-di-IPP, -(254.1 +/- 2.8); 3,5-di-IPP, -(254.1 +/- 2.8); 2,4,6-tri-IPP, -(333.0 +/- 3.1).
- Nesterova, T. N.,Pimerzin, A. A.,Rozhnov, A. M.,Karlina, T. N.
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p. 385 - 396
(2007/10/02)
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