De-t-butylation of phenols catalysed by bulk and supported heteropoly acid
作者： I.V. Kozhevnikov , M.N. Timofeeva
DOI: 10.1016/0304-5102(92)80120-6
关键词: Acid strength 、 Kinetics 、 Catalysis 、 Phenols 、 Chemistry 、 Medicinal chemistry 、 Heterogeneous catalysis 、 Heteropoly acid 、 Stereochemistry 、 Turnover number 、 Electrophilic aromatic substitution
摘要: Abstract Kinetics and mechanism of the liquid-phase reaction, 2,6-di-t-butyl-4-methylphenol (DBMP) + ArH → 2-t-butyl-4-methylphenol ArBut, in presence bulk SiO2-supported heteropoly acid H3PW12O40 (PW) as a heterogeneous catalyst have been studied (ArH = PhH, PhMe, PhBut, o-xylene, m-xylene, [DBMP]/[ArH] 1 22 mol mol−1, 5–25 °C). Under these conditions no isobutene is formed. The reaction was found to be first order with respect both DBMP catalyst. rate depends on nature way that typical electrophilic aromatic substitution. activation energies are 29 ± 3 19 2 kcal mol−1 for PW 25% PW/SiO2, respectively. activity surface protons PW/SiO2 (turnover number) increases monotonically their strength increasing total loading, reaching maximum PW. discussed.
elsevier.com
sci-hub.se 参考文章(13)
Makoto Misono, Naohiro Nojiri, Recent progress in catalytic technology in japan Applied Catalysis. ,vol. 64, pp. 1- 30 ,(1990) , 10.1016/S0166-9834(00)81550-X
V.M. Mastikhin, S.M. Kulikov, A.V. Nosov, I.V. Kozhevnikov, I.L. Mudrakovsky, M.N. Timofeeva, 1H and 31P MAS NMR studies of solid heteropolyacids and H3PW12O40 supported on SiO2 Journal of Molecular Catalysis. ,vol. 60, pp. 65- 70 ,(1990) , 10.1016/0304-5102(90)85068-S
I. V. Kozhevnikov, S. M. Kulikov, M. N. Timofeeva, A. P. Krysin, T. F. Titova, Transalkylation of phenols over heteropoly acids Reaction Kinetics & Catalysis Letters. ,vol. 45, pp. 257- 263 ,(1991) , 10.1007/BF02070436
Y IZUMI, Catalysis by heterogeneous supported heteropoly acid Journal of Catalysis. ,vol. 84, pp. 402- 409 ,(1983) , 10.1016/0021-9517(83)90011-8
F. R. J. Willemse, E. C. Kooyman, H. B. van Lamoen, D. de Vos, J. Wolters, Trans‐substitution and equilibration of phenols. Part IV. The influence of various catalysts on the trans‐tert‐butylation reaction of phenols; mechanistic aspects Recueil des Travaux Chimiques des Pays-Bas. ,vol. 102, pp. 206- 209 ,(2010) , 10.1002/RECL.19831020403
Reiji Ohtsuka, Yoshio Morioka, Jun-ichi Kobayashi, Studies of the Acidity and Ionic Conductivity of Silica-Supported Heteropoly Compounds. I. The Dehydration oft-Butyl Alcohol over Heteropoly Compound Catalysts Bulletin of the Chemical Society of Japan. ,vol. 62, pp. 3195- 3201 ,(1989) , 10.1246/BCSJ.62.3195
I V Kozhevnikov, Advances in Catalysis by Heteropolyacids Russian Chemical Reviews. ,vol. 56, pp. 811- 825 ,(1987) , 10.1070/RC1987V056N09ABEH003304
George A. Olah, G. K. Surya Prakash, Pradeep S. Iyer, Masashi Tashiro, Takehiko Yamato, Catalysis by solid superacids. 21. Nafion-H catalyzed de-tert-butylation of aromatic compounds Journal of Organic Chemistry. ,vol. 52, pp. 1881- 1884 ,(1987) , 10.1021/JO00385A048
T OKUHARA, Catalysis by heteropoly compounds. VI. The role of the bulk acid sites in catalytic reactions over NaxH3 $minus; xPW12O40*1 Journal of Catalysis. ,vol. 83, pp. 121- 130 ,(1983) , 10.1016/0021-9517(83)90035-0
I. V. Kozhevnikov, A. I. Tsyganok, M. N. Timofeeva, S. M. Kulikov, V. N. Sidelnikov, ALKYLATION OF P-SUBSTITUTED PHENOLS BY HETEROPOLY ACIDS Reaction Kinetics and Catalysis Letters. ,vol. 46, pp. 17- 23 ,(1992) , 10.1007/BF02096672