Journal Article10.1016/J.APCATA.2005.03.001
Alkylation of phenol with cyclohexene over solid acids: Insight in selectivity of O- versus C-alkylation
Ganapati D. Yadav,Parveen Kumar +1 more
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TL;DR: In this paper, the selectivity of various acid catalysts such as sulphated zirconia, sulphonic acid treated hexagonal mesoporous silica (SO 3 -HMS), 20% dodecatungstophospheric acid (DTP) supported on K-10 clay, 20% cesium salt of DTP (Cs 2.5 H 0.5 PW 12 O 40 ), and 20% DTP/HMS was studied to improve selectivity to cyclohexyl phenyl ether.
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Abstract: Alkylation of phenol with cyclohexene with acid catalysts leads to the formation of both O- and C-alkylated products, which are all useful in a variety of industries. The O-alkylated product cyclohexyl phenyl ether is a valuable perfume and can also serve as a precursor to diphenyl ether, a very important bulk chemical. The efficacy of various acid catalysts such as sulphated zirconia, sulphonic acid treated hexagonal mesoporous silica (SO 3 -HMS), 20% (w/w) dodecatungstophospheric acid (DTP) supported on K-10 clay, 20% (w/w) cesium salt of DTP (Cs 2.5 H 0.5 PW 12 O 40 ) supported on K-10 clay (Cs-DTP/K-10) and 20% (w/w) DTP/HMS was studied to improve the selectivity to cyclohexyl phenyl ether. A mixture of 2-cyclohexylphenol, 4-cyclohexylphenol and cyclohexyl phenyl ether was obtained with different selectivities. However, 20% (w/w) DTP/K-10 clay was the most active and selective catalyst for O-alkylation in the range of 45–70 °C at atmospheric pressure. The selectivity to O- versus C-alkylation is strongly dependent on temperature, and at lower temperatures, the selectivity to cyclohexyl phenyl ether increases. The best operating temperature is 60 °C. A mathematical model is built to interpret the kinetic data and develop a mechanism.
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Citations
Selective catalytic hydroalkylation and deoxygenation of substituted phenols to bicycloalkanes
TL;DR: In this article, the HBEA-supported Pd catalyst optimally balances the competing rates of metal catalyzed hydrogenation as well as of solid acid-catalyzed dehydration and carbon-carbon coupling to combine hydrodeoxygenation and dimerization of phenol derivatives to C-12-C-18 bicycloalkanes.
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Solvent-determined mechanistic pathways in zeolite-H-BEA-catalysed phenol alkylation
Yuanshuai Liu,Eszter Baráth,Hui Shi,Jianzhi Hu,Donald M. Camaioni,Johannes A. Lercher,Johannes A. Lercher +6 more
- 29 Jan 2018
TL;DR: In this article, a mechanistic study reveals that the course of the reaction can be dramatically altered by changing the polarity of the solvent, which affects the nature of surface species and the pathway for the generation of the alkylating electrophile.
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Novel mesoporous solid superacids for selective C-alkylation of m-cresol with tert-butanol
TL;DR: In this article, alkylation of m-cresol was studied with tert-butyl alcohol (TBA) using sulphated zirconia and three superacidic catalysts, namely, UDCaT-4, 5 and 6.
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Tuning the acid–metal balance in Pd/ and Pt/zeolite catalysts for the hydroalkylation of m-cresol
TL;DR: In this paper, the liquid-phase hydroalkylation of m-cresol catalyzed by zeolite catalysts doped with noble metals was investigated at 473k and 5200kPa of H 2.
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Catalytic applications of mesoporous silica-based materials
Rafael Luque,Alina M. Balu,Juan M. Campelo,Maria Dolores Gracia,Elia Losada,Antonio Pineda,Antonio A. Romero,Juan Carlos Serrano-Ruiz +7 more
TL;DR: In this article, an overview on the utilization of mesoporous materials in heterogeneous catalysis, with special emphasis on acid and redox catalysed processes, is provided, where the authors aim to provide an overview of the application of meso-materials in various areas including adsorption, separation, drug delivery, sensing and catalysis.
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References
Novelties of eclectically engineered sulfated zirconia and carbon molecular sieve catalysts in cyclisation of citronellal to isopulegol
Ganapati D. Yadav,Jayesh J. Nair +1 more
TL;DR: Sulfated zirconia (S-ZrO2) is a well-known solid superacid catalyst used in various reactions of commercial importance such as isomerization, alkylation and acylation, nitration, etc as mentioned in this paper.
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Kinetics and Mechanism of Selective Monoacylation of Mesitylene
TL;DR: In this paper, the authors used K-10 montomorillonite clay-based heteropolyacids such as dodecatungstophosphoric acid (DTP) and DTS for monoacylation.
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Selectivity engineering in the nitration of chlorobenzene using eclectically engineered sulfated zirconia and carbon molecular sieve catalysts
Ganapati D. Yadav,Jayesh J. Nair +1 more
TL;DR: In this paper, the p : o ratio in chlorobenzene nitration was found to be very high with eclectically engineered sulfated zirconia and carbon molecular sieve catalyst.
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Deactivation of ion-exchange resin catalysts. Part I: Alkylation of o-xylene with styrene
A.B. Dixit,Ganapati D. Yadav +1 more
TL;DR: In this article, the pore structure data of the virgin and deactivated catalyst were analyzed by using various techniques such as mercury porosimetry, BET surface area and SEM.
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