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
Reaction pathways in the liquid phase alkylation of biomass‐derived phenolic compounds
TL;DR: In this article, the alkylation of m-cresol with isopropanol and HY zeolite was studied in a liquid phase system and the experimental results were fitted with two conventional surface kinetic models, Langmuir-Hinshelwood and Eley-Rideal, from which adsorption and rate constants were estimated.
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Reactions of Phenol, Water, Acetic Acid, Methanol, and 2-Hydroxymethylfuran with Olefins as Models for Bio-oil Upgrading
TL;DR: In this article, liquid phase reactions of 1-octene with phenol in the presence of water, acetic acid, methanol, and 2-hydroxymethylfuran, respectively, were carried out over acid catalysts for bio-oil upgrading, including 30 wt % acidic salt Cs2.5H0.5PW12O40 supported on K-10 clay.
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Sulfonic acid resin-catalyzed addition of phenols, carboxylic acids, and water to olefins: Model reactions for catalytic upgrading of bio-oil.
TL;DR: Adding 1-butanol to phenol/water/1-octene, gave emulsion-like mixtures which improved phenol conversion and olefin hydration, and were more stable in the presence of water than Amberlyst15 and were successfully recycled.
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Alkylation of lignin-derived aromatic oxygenates with cyclic alcohols on acidic zeolites
Yuanshuai Liu,Guanhua Cheng,Eszter Baráth,Hui Shi,Hui Shi,Johannes A. Lercher,Johannes A. Lercher +6 more
TL;DR: In this paper, the authors show that for the alkylation of phenols and cyclic alcohols in apolar liquids, the alcohol concentration should be kept low to avoid the formation of unreactive surface dimers and mitigate their inhibitory effects on olefin adsorption and protonation.
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Starbon® acids in alkylation and acetylation reactions: Effect of the Brönsted-Lewis acidity
TL;DR: In this paper, various Starbon® supported solid acids were prepared and investigated in two test reactions, namely the acetylation of 5-acetyl-methylsalicylate and the alkylation of phenol with cyclohexene.
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Ganapati D. Yadav,Jayesh J. Nair +1 more
TL;DR: In this article, the chemistry and engineering aspects of sulfated zirconia catalyst and its modified forms are discussed, and the surface properties of these catalysts can be further modified in conjunction with noble or transition metals as promoters as well as with carbon molecular sieves.
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Esterification of maleic acid with ethanol over cation-exchange resin catalysts
Ganapati D. Yadav,M.B Thathagar +1 more
TL;DR: In this paper, the efficacy of several heterogeneous catalysts, such as Indion-170, Amberlyst-36, Amberleyst-15, Amberlite IRA 120, 20% DTP/K-10 (dodecatungstophosphoric acid supported on K-10 clay) in the esterification of maleic acid with ethanol at reflux was evaluated.
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Preparation of a novel catalyst UDCaT-5: enhancement in activity of acid-treated zirconia—effect of treatment with chlorosulfonic acid vis-à-vis sulfuric acid
TL;DR: UDCaT-5 as discussed by the authors is a zirconia-based catalyst with high sulfur content (9%w/w) but preservation of the tetragonal phase of ZrO2 was synthesized for the first time, by using chlorosulfonic acid as a new source for sulfate ions.
144
Synthesis of bisphenol-A: comparison of efficacy of ion exchange resin catalysts vis-à-vis heteropolyacid supported on clay and kinetic modelling
Ganapati D. Yadav,N. Kirthivasan +1 more
TL;DR: In this article, the use of a novel catalyst based on heteropolyacid supported on clay, particularly dodecatungstophosphoric acid (DTP) supported on K-10 clay, was reported.
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