The pi bond could swing so that the hydrogen atom becomes attached to the left-hand carbon. EXPLAINING THE INDUSTRIAL ALKYLATION OF BENZENE. Elena Khlebnikova, Elena Ivashkina, Irena Dolganova. Journal of Molecular Catalysis A: Chemical. The effect of reaction temperature, benzene/propene molar ratio and weight hourly space velocity (WHSV) upon the conversion of propene and the selectivity of cumene are reported. EXPERIMENTAL The procedure for the synthesis of a Ni/y-A1203 catalyst has been described in a previous paper [ 2 ] . When the propene reacts with the HCl, there are two different ways that the initial stage of the addition reaction could happen. Please contact your library or account administrator. redistribute this material, requesters must process their own requests via the RightsLink permission Mathematical Modeling of Liquid-Phase Alkylation of Benzene with Ethylene Considering the Process Unsteadiness.
It has been shown that H-Beta zeolite (Si/Al ratio=10) is a very active catalyst for this reaction with propene, but it leads also to fast oligomerization even at lower reaction temperatures. You’ve supercharged your research process with ACS and Mendeley! This article is cited by y-A1203 was macerated with nickel salt solution, then dried and calcined to … 9 publications. http://pubs.acs.org/page/copyright/permissions.html. As a result, the reaction will be across the double bond in the propenyl group. Although these mechanisms weren't actually required by the syllabus, in the past one UK Exam Board (NEAB - now part of AQA) frequently asked guided questions about them. Alkylation of benzene with propene has been investigated on a series of H-Beta zeolites with different Si/Al ratio: 10, 35 and 66, using different techniques such as FTIR, 13C NMR and catalytic testing. Mechanistic Investigations of Liquid-phase Direct Alkylation of Benzene with n-Heptane Using Proton-exchanged Montmorillonite Catalysts. One of the aluminium-chlorine bonds breaks and both electrons from it are used to join to the hydrogen. Chemical Engineering and Processing - Process Intensification. In each case, you can only really be sure of that structure if … 13C NMR experiments have demonstrated for the first time that the reaction of alkylation is already complete at −80°C on these catalysts. University of Liverpool, Department of Chemistry, Liverpool L69 7ZD, U.K. Elena Ivashkina, Elena Khlebnikova, Irena Dolganova, Igor Dolganov. Rather, the proton transfer to the 2-butene produces a carbocation, which is attacked by the benzene, resulting in alkylation of the benzene ring. Junfen Li,, Zhangfeng Qin,, Guofu Wang,, Mei Dong, and. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting The present work reveals that the alkylation of benzene by propene occurs via an Eley–Rideal type mechanism. The next bit adds another layer of difficulty. Critical Properties of the Reacting Mixture in the Esterification of Acetic Acid with Ethanol. Tuoping Hu,, Zhangfeng Qin,, Guofu Wang,, Xianglin Hou, and. Shuai Guo, Yushan Wu, Tao Jin, Hongtao Wang, Chenglong Dong, Jianli Zhang, Mingyue Ding. Xing Cui Guo, Zhang Feng Qin, Guo Fu Wang, Jian Guo Wang. reaction of ethene with hydrogen halides, addition of hydrogen halides to unsymmetrical alkenes.
Journal of Molecular Catalysis A: Chemical, https://doi.org/10.1016/S1381-1169(99)00357-X. The critical properties of both binary and ternary mixtures (benzene + propene, benzene + cumene, cumene + propene, and benzene + propene + cumene) involved in the alkylation of benzene with propene were measured by using a high-pressure view cell with visual observation. Your Mendeley pairing has expired.
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.5b01102. Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Critical Temperatures and Pressures of the Reacting Mixture in the Acylation of Anisole with Acetic Anhydride. system.
Dealuminated H-Beta zeolites are less active but lead to less aromatic by-products (especially n-propylbenzene) and the deactivation due to the coke formation is reduced. Find more information about Crossref citation counts. Tel. Moreover, the critical properties of the ternary mixture were determined with the compositions representing the reaction proceeding extent of alkylation, with the initial mole ratios of benzene to propene being 3, 4, 5, and 6, respectively. Get article recommendations from ACS based on references in your Mendeley library. The problem with more complicated alkenes like propene is that you have to be careful about the structure of the product. The alkylation of benzene with propene to produce cumene over HBeta zeolites was carried out near supercritical conditions, where the reaction conditions were determined with considering the changes in the critical properties of reacting mixture along with the reaction extent.
As the CH3CH2+ ion approaches the delocalised electrons in the benzene, those electrons are strongly attracted towards the positive charge. If you are going to replace a hydrogen atom in a benzene ring by CH3CH2, then the electrophile must be the ion CH3CH2+. Industrial & Engineering Chemistry Research. Alternatively, the pi bond electrons could move the other way and form a secondary carbocation. from the ACS website, either in whole or in part, in either machine-readable form or any other form Jared M. Clark, Heidi M. Pilath, Ashutosh Mittal, William E. Michener, David J. Robichaud, and David K. Johnson . Benzene alkylation with ethylene: The way to increase the process efficiency.
We need to show it there because it has to be removed in the second stage. Two electrons from the delocalised system are used to form a new bond with the positive carbon atom. To whom correspondence should be addressed. Box 165, Taiyuan, Shanxi 030001, People's Republic of China.
The secondary carbocation (with the positive charge on the centre carbon atom) is the more stable, and so that forms more readily.
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