Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/formation-mechanism-of-the-first-carbon-carbon-bond-and-the-first-j4SIjeHpsD
References (30)
-
P. Tian, Yingxu Wei, M. Ye, Zhongmin Liu (2015)
Methanol to Olefins (MTO): From Fundamentals to CommercializationACS Catalysis, 5
-
E. Munson, A. Kheir, N. Lazo, J. Haw (1992)
In situ solid-state NMR study of methanol-to-gasoline chemistry in zeolite HZSM-5The Journal of Physical Chemistry, 96
-
S. Müller, Yue Liu, M. Vishnuvarthan, Xianyong Sun, A. Veen, G. Haller, M. Sanchez-Sanchez, J. Lercher (2015)
Coke formation and deactivation pathways on H-ZSM-5 in the conversion of methanol to olefinsJournal of Catalysis, 325
-
N. Tajima, T. Tsuneda, and Toyama, K. Hirao (1998)
A New Mechanism for the First Carbon−Carbon Bond Formation in the MTG Process: A Theoretical StudyJournal of the American Chemical Society, 120
-
A. Stepanov, M. Luzgin, V. Romannikov, V. Sidelnikov, K. Zamaraev (1996)
Formation of Carboxylic Acids from Alcohols and Olefins in Zeolite H-ZSM-5 under Mild Conditions via Trapping of Alkyl Carbenium Ions with Carbon Monoxide: Anin Situ13C Solid State NMR StudyJournal of Catalysis, 164
-
Yuchuan Fu, Haiyan Zhu, Jianyi Shen (2005)
Thermal decomposition of dimethoxymethane and dimethyl carbonate catalyzed by solid acids and basesThermochimica Acta, 434
-
Patricia Cheung, A. Bhan, G. Sunley, E. Iglesia (2006)
Selective carbonylation of dimethyl ether to methyl acetate catalyzed by acidic zeolites.Angewandte Chemie, 45 10
-
Xianyong Sun, S. Mueller, Yue Liu, Hui Shi, G. Haller, M. Sanchez-Sanchez, A. Veen, J. Lercher (2014)
On reaction pathways in the conversion of methanol to hydrocarbons on HZSM-5Journal of Catalysis, 317
-
G. Hutchings, P. Johnston, Darren Lee, Craig Williams (1993)
Acetone conversion to isobutene in high selectivity using zeolite β catalystCatalysis Letters, 21
-
G. Hutchings, F. Gottschalk, R. Hunter (1987)
Comments on "kinetic model for methanol conversion to olefins" with respect to methane formation at low conversionIndustrial & Engineering Chemistry Research, 26
-
E. Munson, N. Lazo, Meg Moellenhoff, J. Haw (1991)
Carbon monoxide is neither an intermediate nor a catalyst in MTG chemistry on zeolite HZSM-5Journal of the American Chemical Society, 113
-
A. Stepanov, M. Luzgin, V. Romannikov, K. Zamaraev (1995)
NMR OBSERVATION OF THE KOCH REACTION IN ZEOLITE H-ZSM-5 UNDER MILD CONDITIONSJournal of the American Chemical Society, 117
-
A. Comas‐Vives, Maxence Valla, C. Copéret, P. Sautet (2015)
Cooperativity between Al Sites Promotes Hydrogen Transfer and Carbon–Carbon Bond Formation upon Dimethyl Ether Activation on AluminaACS Central Science, 1
-
M. Bjørgen, S. Svelle, F. Joensen, J. Nerlov, S. Kolboe, F. Bonino, Luisa Palumbo, S. Bordiga, U. Olsbye (2007)
Conversion of methanol to hydrocarbons over zeolite H-ZSM-5 : On the origin of the olefinic speciesJournal of Catalysis, 249
-
M. Wu, W. Kaeding (1984)
Conversion of methanol to hydrocarbons: II. Reaction paths for olefin formation over HZSM-5 zeolite catalystJournal of Catalysis, 88
-
Tu Pham, T. Sooknoi, S. Crossley, D. Resasco (2013)
Ketonization of Carboxylic Acids: Mechanisms, Catalysts, and Implications for Biomass ConversionACS Catalysis, 3
-
S. Ilias, A. Bhan (2013)
Mechanism of the Catalytic Conversion of Methanol to HydrocarbonsACS Catalysis, 3
-
M. Boronat, Cristina Martínez-Sánchez, D. Law, A. Corma (2008)
Enzyme-like specificity in zeolites: a unique site position in mordenite for selective carbonylation of methanol and dimethyl ether with CO.Journal of the American Chemical Society, 130 48
-
Patricia Cheung, A. Bhan, G. Sunley, D. Law, E. Iglesia (2007)
Site requirements and elementary steps in dimethyl ether carbonylation catalyzed by acidic zeolitesJournal of Catalysis, 245
-
Michael Anderson, J. Klinowski (1989)
Direct observation of shape selectivity in zeolite ZSM-5 by magic-angle-spinning NMRNature, 339
-
M. Stöcker (1999)
Methanol-to-hydrocarbons: catalytic materials and their behavior 1 Dedicated to my wife Wencke OphauMicroporous and Mesoporous Materials
-
G. Hutchings, R. Hunter, P. Johnston, L. vanRensburg (1993)
Methanol conversion to hydrocarbons over zeolite H-ZSM-5: Investigation of the role of CO and ketene in the formation of the initial C-C bondJournal of Catalysis, 142
-
J. Nováková, L. Kubelková, Z. Dolejšek (1987)
Primary reaction steps in the methanol-to-olefin transformation on zeolitesJournal of Catalysis, 108
-
David Lesthaeghe, V. Speybroeck, G. Marin, M. Waroquier (2006)
Understanding the failure of direct C-C coupling in the zeolite-catalyzed methanol-to-olefin process.Angewandte Chemie, 45 11
-
Weiguo Song, D. Marcus, H. Fu, J. Ehresmann, J. Haw (2002)
An oft-studied reaction that may never have been: direct catalytic conversion of methanol or dimethyl ether to hydrocarbons on the solid acids HZSM-5 or HSAPO-34.Journal of the American Chemical Society, 124 15
-
R. Dessau (1986)
On the H-ZSM-5 catalyzed formation of ethylene from methanol or higher olefinsJournal of Catalysis, 99
-
M. Boronat, C. Martínez, A. Corma (2011)
Mechanistic differences between methanol and dimethyl ether carbonylation in side pockets and large channels of mordenite.Physical chemistry chemical physics : PCCP, 13 7
-
N. Govind, J. Andzelm, Kurt Reindel, G. Fitzgerald (2002)
Zeolite-Catalyzed Hydrocarbon Formation from Methanol: Density Functional SimulationsInternational Journal of Molecular Sciences, 3
-
T. Mole, G. Bett, D. Seddon (1983)
Conversion of methanol to hydrocarbons over ZSM-5 zeolite: An examination of the role of aromatic hydrocarbons using 13carbon- and deuterium-labeled feedsJournal of Catalysis, 84
-
S. Blaszkowski, V. Santen (1997)
Theoretical study of C-C bond formation in the methanol to gasoline processJournal of the American Chemical Society, 119
- Publisher
- Wiley
- Copyright
- © 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 1433-7851
- eISSN
- 1521-3773
- DOI
- 10.1002/anie.201511678
- pmid
- 27037603
- Publisher site
- See Article on Publisher Site
Abstract
The elementary reactions leading to the formation of the first carbon–carbon bond during early stages of the zeolite‐catalyzed methanol conversion into hydrocarbons were identified by combining kinetics, spectroscopy, and DFT calculations. The first intermediates containing a C−C bond are acetic acid and methyl acetate, which are formed through carbonylation of methanol or dimethyl ether even in presence of water. A series of acid‐catalyzed reactions including acetylation, decarboxylation, aldol condensation, and cracking convert those intermediates into a mixture of surface bounded hydrocarbons, the hydrocarbon pool, as well as into the first olefin leaving the catalyst. This carbonylation based mechanism has an energy barrier of 80 kJ mol−1 for the formation of the first C−C bond, in line with a broad range of experiments, and significantly lower than the barriers associated with earlier proposed mechanisms.
Journal
Angewandte Chemie International Edition – Wiley
Published: May 4, 2016
Keywords: ; ; ; ;