Diethyl carbonate synthesis by ethanolysis of urea using Ce-Zn oxide catalysts

Fuel Processing Technology - Tập 161 - Trang 116-124 - 2017
Kartikeya Shukla1, Vimal Chandra Srivastava1
1Department of Chemical Engineering, Indian Institute of Technology Roorkee, Roorkee, 247667, Uttarakhand, India

Tài liệu tham khảo

Pacheco, 1997, Review of dimethyl carbonate (DMC) manufacture and its characteristics as a fuel additive, Energy Fuel, 11, 2, 10.1021/ef9600974 Bruno, 2009, Composition-explicit distillation curves for mixtures of diesel fuel with dimethyl carbonate and diethyl carbonate, Energy Fuel, 23, 3989, 10.1021/ef900215v Bruno, 2011, Comparison of diesel fuel oxygenate additives to the composition-explicit distillation curve method. Part 1: Linear compounds with one to three oxygens, Energy Fuel, 25, 2493, 10.1021/ef2003415 Udayakumar, 2004, Para-selective ethylation of phenol with diethyl carbonate over mesoporous Al-MCM-41 molecular sieves, Appl. Catal. A-Gen., 272, 267, 10.1016/j.apcata.2004.05.051 Poizot, 2000, Nano-sized transition-metal oxides as negative-electrode materials for lithium-ion batteries, Nature, 407, 496, 10.1038/35035045 Wang, 2014, Highly efficient synthesis of diethyl carbonate via one-pot reaction from carbon dioxide, epoxides and ethanol over KI-based binary catalyst system, Appl. Catal. A-Gen., 471, 19, 10.1016/j.apcata.2013.11.031 Hou, 2014, High-yield synthesis of dimethyl carbonate from the direct alcoholysis of urea in supercritical methanol, Chem. Eng. J., 236, 415, 10.1016/j.cej.2013.09.024 Wang, 2007, Synthesis of diethyl carbonate by catalytic alcoholysis of urea, Fuel Process. Technol., 88, 807, 10.1016/j.fuproc.2007.04.003 Wang, 2015, Transition metal-modified mesoporous Mg-Al mixed oxides: stable base catalysts for the synthesis of diethyl carbonate from ethyl carbamate and ethanol, Appl. Catal. A-Gen., 505, 478, 10.1016/j.apcata.2015.04.034 Briggs, 2009, An investigation of carbon-supported CuCl2/PdCl2 catalysts for diethyl carbonate synthesis, Appl. Catal. A-Gen., 366, 71, 10.1016/j.apcata.2009.06.032 Zielinska-Nadolska, 2006, Zeolite and other heterogeneous catalysts for the transesterification reaction of dimethyl carbonate with ethanol, Catal. Today, 114, 226, 10.1016/j.cattod.2006.01.001 Qiu, 2010, Characterization of KF/γ-Al2O3 catalyst for the synthesis of diethyl carbonate by transesterification of ethylene carbonate, Catal. Lett., 137, 232, 10.1007/s10562-010-0354-8 Qiu, 2012, Synthesis of diethyl carbonate by the combined process of transesterification with distillation, Energy Fuel, 26, 1254, 10.1021/ef201732w Kumar, 2016, Dimethyl carbonate synthesis from carbon dioxide using ceria–zirconia catalysts prepared using a templating method: characterization, parametric optimization and chemical equilibrium modeling, RSC Adv., 6, 110235, 10.1039/C6RA22643D Shukla, 2016, Diethyl carbonate: critical review of synthesis routes, catalysts used and engineering aspects, RSC Adv., 6, 32624, 10.1039/C6RA02518H Shukla, 2017, Synthesis of organic carbonates from alcoholysis of urea: a review, Catal. Rev., 59, 1, 10.1080/01614940.2016.1263088 Itoh, 2003, Synthesis of dimethyl carbonate by vapor phase oxidative carbonylation of methanol, Green Chem., 5, 558, 10.1039/B304618B Wang, 2006, Synthesis of dimethyl carbonate from urea and methanol over solid base catalysts, Catal. Commun., 7, 6, 10.1016/j.catcom.2005.08.003 Zhang, 2010, Kinetics studies of dimethyl carbonate synthesis from urea and methanol over ZnO catalyst, Korean J. Chem. Eng., 27, 1744, 10.1007/s11814-010-0306-4 Wang, 2010, Synthesis of dimethyl carbonate from methyl carbamate and methanol over lanthanum compounds, Fuel Process. Technol., 91, 1081, 10.1016/j.fuproc.2010.03.017 Hao, 2009, Gas phase decarbonylation of diethyl oxalate to diethyl carbonate over alkali-containing catalyst, J. Mol. Catal. A-Chem., 306, 130, 10.1016/j.molcata.2009.02.038 Zhang, 2012, Experimental and kinetic studies on a homogeneous system for diethyl carbonate synthesis by transesterification, Chem. Eng. Technol., 35, 693, 10.1002/ceat.201100276 Wang, 2012, Synthesis of dimethyl carbonate from methyl carbamate and methanol using a fixed-bed reactor, Chem. Eng. Technol., 35, 2183, 10.1002/ceat.201200217 Wu, 2014, Dimethyl carbonate synthesis over ZnO–CaO bi-functional catalysts, Catal. Commun., 46, 46, 10.1016/j.catcom.2013.10.040 Lin, 2004, Kinetics studies for the synthesis of dimethyl carbonate from urea and methanol, Chem. Eng. J., 103, 21, 10.1016/j.cej.2004.07.003 Sun, 2005, Synthesis of dimethyl carbonate from urea and methanol using polyphosphoric acid as catalyst, J. Mol. Catal. A-Chem., 239, 82, 10.1016/j.molcata.2005.06.001 Wang, 2006, Reactive rectifying for producing dimethyl carbonate, Chem. Eng. J., 122, 15, 10.1016/j.cej.2006.05.001 Yang, 2006, Synthesis of dimethyl carbonate from urea and methanol catalyzed by the metallic compounds at atmospheric pressure, Catal. Commun., 7, 472, 10.1016/j.catcom.2006.01.009 Zhao, 2004, Synthesis of propylene carbonate from urea and 1, 2-propylene glycol over a zinc acetate catalyst, Ind. Eng. Chem. Res., 43, 4038, 10.1021/ie049948i Wang, 2010, Synthesis of dimethyl carbonate from methyl carbamate and methanol catalyzed by mixed oxides from hydrotalcite-like compounds, J. Phys. Chem. Solids, 71, 427, 10.1016/j.jpcs.2009.12.005 Wang, 2010, Zn/Fe mixed oxide: heterogeneous catalyst for the synthesis of dimethyl carbonate from methyl carbamate and methanol, Catal. Commun., 11, 430, 10.1016/j.catcom.2009.11.016 Zhao, 2011, Pseudo-homogenous kinetics model for the synthesis of dimethyl carbonate from urea and methanol with heterogeneous catalyst, Adv. Mat.Res., 233, 481 Zhao, 2012, Reaction mechanism and kinetics of dimethyl carbonate synthesis from methyl carbamate and methanol, Ind. Eng. Chem. Res., 51, 16580, 10.1021/ie302245n Wang, 2015, Catalytic alcoholysis of urea to diethyl carbonate over calcined Mg–Zn–Al hydrotalcite, RSC Adv., 5, 19534, 10.1039/C4RA15897K Ryu, 2002, Process and catalyst for making dialkyl carbonates, U.S. Patent, 6 Saleh, 1998, Process for the preparation of dialkyltin dialkoxide from alkyl carbamate and alcohol, U.S. Patent, 5 Xin, 2014, Synthesis of diethyl carbonate from urea and ethanol over lanthanum oxide as a heterogeneous basic catalyst, Fuel Process. Technol., 126, 453, 10.1016/j.fuproc.2014.05.029 Wu, 2014, Synthesis of dimethyl carbonate by urea alcoholysis over Zn/Al bi-functional catalysts, Appl. Catal. A-Gen., 473, 13, 10.1016/j.apcata.2013.12.034 Wang, 2007, High-yield synthesis of dimethyl carbonate from urea and methanol using a catalytic distillation process, Ind. Eng. Chem. Res., 46, 2683, 10.1021/ie061101u Singha, 2016, Synthesis of highly coke resistant Ni nanoparticles supported MgO/ZnO catalyst for reforming of methane with carbon dioxide, Appl. Catal. B-Environ., 191, 165, 10.1016/j.apcatb.2016.03.029 Enjamuri, 2016, Nobel metal free, oxidant free, solvent free catalytic transformation of alcohol to aldehyde over ZnO-CeO2 mixed oxide catalyst, Appl. Catal. A-Gen., 523, 21, 10.1016/j.apcata.2016.05.003 Wang, 2005, Synthesis of dimethyl carbonate from urea and methanol over ZnO, Ind. Eng. Chem. Res., 44, 7596, 10.1021/ie0504553 Wang, 2007, Measurement of concentration profiles over ZnO–Cr2O3/CeO2–ZrO2 monolithic catalyst in oxidative steam reforming of methanol, Fuel Process. Technol., 88, 65, 10.1016/j.fuproc.2006.08.007 Shukla, 2016, Catalytic oxidation of aromatic amines to azoxy compounds over a Cu–CeO2 catalyst using H2O2 as an oxidant, RSC Adv., 6, 22812, 10.1039/C5RA25699B Mandal, 2013, Sm-CeO2 supported gold nanoparticle catalyst for benzyl alcohol oxidation using molecular O2, Appl. Catal. A-Gen., 452, 94, 10.1016/j.apcata.2012.11.030 He, 2006, Preparation of CeO2/ZnO nanostructured microspheres and their catalytic properties, Powder Technol., 166, 72, 10.1016/j.powtec.2006.05.013 Bhanage, 2003, Synthesis of dimethyl carbonate from CO2 and ethylene oxide catalyzed by K2CO3-based binary salts in the presence of H2O, Green Chem., 5, 429, 10.1039/b304182d Cannas, 2004, New synthesis of ferrite–silica nanocomposites by a sol–gel auto-combustion, J. Nanopart. Res., 6, 223, 10.1023/B:NANO.0000034679.22546.d7 Kakihana, 1999, Spectroscopic characterization of precursors used in the Pechini-type polymerizable complex processing of barium titanate, Chem. Mater., 11, 438, 10.1021/cm9806681 Anedda, 2008, A two-stage citric acid–sol/gel synthesis of ZnO/SiO2 nanocomposites: study of precursors and final products, J. Nanopart. Res., 10, 107, 10.1007/s11051-007-9235-5 Abdullah, 2012, Chelating agents role on thermal characteristics and phase formation of modified cerate-zirconate via sol-gel synthesis route, Int. J. Electrochem. Sci., 7, 9401, 10.1016/S1452-3981(23)16206-7 Zak, 2011, X-ray analysis of ZnO nanoparticles by Williamson–Hall and size–strain plot methods, Solid State Sci., 13, 251, 10.1016/j.solidstatesciences.2010.11.024 Zhou, 2013, Effects of the structure of Ce-Cu catalysts on the catalytic combustion of toluene in air, Ceram. Int., 39, 3677, 10.1016/j.ceramint.2012.10.199 Brunauer, 1940, On a theory of the van der Waals adsorption of gases, Am. Chem. Soc., 62, 1723, 10.1021/ja01864a025 Kumar, 2013, Structural and optical characterization of ZnO nanoparticles synthesized by microemulsion route, Int. Lett. Chem. Phys. Astronom., 14, 26, 10.18052/www.scipress.com/ILCPA.19.26 Mishra, 2006, Promoting effect of ceria on the physicochemical and catalytic properties of CeO2–ZnO composite oxide catalysts, J. Mol. Catal. A-Chem., 243, 204, 10.1016/j.molcata.2005.07.048 Zhang, 2007, Formation and thermal decomposition of cerium-organic precursor for nanocrystalline cerium oxide powder synthesis, J. Dispers. Sci. Technol., 28, 1053, 10.1080/01932690701524091 Du, 2003, Structural and optical properties of nanophase zinc oxide, Appl. Phys. A Mater. Sci. Process., 76, 171, 10.1007/s003390201404 Lindstrom, 2008 Benson, 1958, Additivity rules for the estimation of molecular properties. Thermodynamic properties, J. Chem. Phys., 29, 546, 10.1063/1.1744539 Belson, 1982, Preparation and properties of isocyanic acid, Chem. Soc. Rev., 11, 41, 10.1039/cs9821100041