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Pure Appl. Chem., 2001, Vol. 73, No. 7, pp. 1117-1124

http://dx.doi.org/10.1351/pac200173071117

New developments in dimethyl carbonate chemistry

Pietro Tundo

Dipartimento di Scienze Ambientali, Università Ca' Foscari Dorsoduro 2137 ­ 30123 Venezia, Italy

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  • Wu Xiaomin, Kang Min, Yin Yanlong, Wang Feng, Zhao Ning, Xiao Fukui, Wei Wei, Sun Yuhan: Synthesis of dimethyl carbonate by urea alcoholysis over Zn/Al bi-functional catalysts. Applied Catalysis A: General 2014, 473, 13. <http://dx.doi.org/10.1016/j.apcata.2013.12.034>
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  • Wang Lei, Han Xiaolong, Li Jiding, Zheng Dongju, Qin Lin: Modified MCM-41 silica spheres filled polydimethylsiloxane membrane for dimethylcarbonate/methanol separation via pervaporation. J. Appl. Polym. Sci. 2013, 127, 4662. <http://dx.doi.org/10.1002/app.38046>
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  • Zhang Cheng, Lu Bin, Wang Xiaoguang, Zhao Jingxiang, Cai Qinghai: Selective synthesis of dimethyl carbonate from urea and methanol over Fe2O3/HMCM-49. Catal Sci Technol 2012, 2, 305. <http://dx.doi.org/10.1039/c1cy00216c>
  • Wang Jin-Quan, Sun Jian, Cheng Wei-Guo, Shi Chun-Yan, Dong Kun, Zhang Xiang-Ping, Zhang Suo-Jiang: Synthesis of dimethyl carbonate catalyzed by carboxylic functionalized imidazolium salt via transesterification reaction. Catal Sci Technol 2012, 2, 600. <http://dx.doi.org/10.1039/c1cy00342a>
  • Righi Giuliana, Bovicelli Paolo, Barontini Maurizio, Tirotta Ilaria: Dimethyl carbonate in the regio- and stereocontrolled opening of three-membered heterocyclic rings. Green Chem 2012, 14, 495. <http://dx.doi.org/10.1039/c2gc16241e>
  • Shang Jianpeng, Liu Shimin, Ma Xiangyuan, Lu Liujin, Deng Youquan: A new route of CO2 catalytic activation: syntheses of N-substituted carbamates from dialkyl carbonates and polyureas. Green Chem. 2012, 14, 2899. <http://dx.doi.org/10.1039/c2gc36043h>
  • Glasnov Toma N., Holbrey John D., Kappe C. Oliver, Seddon Kenneth R., Yan Ting: Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions. Green Chem. 2012, 14, 3071. <http://dx.doi.org/10.1039/c2gc36226k>
  • Eta Valerie, Mäki-Arvela Päivi, Salminen Eero, Salmi Tapio, Murzin Dmitry Yu., Mikkola Jyri-Pekka: The Effect of Alkoxide Ionic Liquids on the Synthesis of Dimethyl Carbonate from CO2 and Methanol over ZrO2–MgO. Catal Let 2011, 141, 1254. <http://dx.doi.org/10.1007/s10562-011-0666-3>
  • Arteconi Alessia, Mazzarini Alessandro, Nicola Giovanni: Emissions from Ethers and Organic Carbonate Fuel Additives: A Review. Water Air & Soil Pollut 2011, 221, 405. <http://dx.doi.org/10.1007/s11270-011-0804-y>
  • Song Jinliang, Zhang Binbin, Jiang Tao, Yang Guanying, Han Buxing: Synthesis of cyclic carbonates and dimethyl carbonate using CO2 as a building block catalyzed by MOF-5/KI and MOF-5/KI/K2CO3 . Front Chem China 2011, 6, 21. <http://dx.doi.org/10.1007/s11458-011-0225-x>
  • Eta Valerie, Mäki-Arvela Päivi, Wärnå Johan, Salmi Tapio, Mikkola Jyri-Pekka, Murzin Dmitry Yu.: Kinetics of dimethyl carbonate synthesis from methanol and carbon dioxide over ZrO2–MgO catalyst in the presence of butylene oxide as additive. CATAL A GENERAL 2011. <http://dx.doi.org/10.1016/j.apcata.2011.07.004>
  • Wang Lei, Han Xiaolong, Li Jiding, Zhan Xia, Chen Jian: Hydrophobic nano-silica/polydimethylsiloxane membrane for dimethylcarbonate–methanol separation via pervaporation. Chem Eng J 2011, 171, 1035. <http://dx.doi.org/10.1016/j.cej.2011.04.058>
  • Gao Yangyan, Peng Weicai, Zhao Ning, Wei Wei, Sun Yuhan: A DFT study on the reaction mechanism for dimethyl carbonate synthesis from methyl carbamate and methanol. Journal of Molecular Catalysis A 2011, 351, 29. <http://dx.doi.org/10.1016/j.molcata.2011.09.006>
  • Oelkers Benjamin, Sundermeyer Jörg: Pentaalkylmethylguanidinium methylcarbonates – versatile precursors for the preparation of halide-free and metal-free guanidinium-based ILs. Green Chem 2011, 13, 608. <http://dx.doi.org/10.1039/c0gc00698j>
  • Sun Jian, Shi Chun-Yan, Cheng Wei-Guo, Zhang Xiang-Ping, Zhang Suo-Jiang, Wang Jin-Quan: Synthesis of dimethyl carbonate from CO2 and ethylene oxide catalyzed by K2CO3-based binary salts in the presence of H2O. Green Chem 2011, 13, 3213. <http://dx.doi.org/10.1039/c1gc15812k>
  • Xie Jian-Gang, Quan Jing, Li Shu-Bai, Zheng Yan, Zhu Li-Min: SH-Methylation of SH-Containing Heterocycles with Dimethyl Carbonate via Phase-Transfer Catalytic Reaction. Synthetic Communications 2011, 41, 871. <http://dx.doi.org/10.1080/00397911003707048>
  • Wang Lei, Han Xiaolong, Li Jiding, Zhan Xia, Chen Jian: Separation of Azeotropic Dimethylcarbonate/Methanol Mixtures by Pervaporation: Sorption and Diffusion Behaviors in the Pure and Nano Silica Filled PDMS Membranes. Sep Sci Technol 2011, 46, 1396. <http://dx.doi.org/10.1080/01496395.2011.571227>
  • Andraos John: A green metrics assessment of phosgene and phosgene-free syntheses of industrially important commodity chemicals. PureAppl Chem 2011, 1. <http://dx.doi.org/10.1351/PAC-CON-11-06-12>
  • Pyo Sang-Hyun, Persson Per, Mollaahmad M. Amin, Sörensen Kent, Lundmark Stefan, Hatti-Kaul Rajni: Cyclic carbonates as monomers for phosgene- and isocyanate-free polyurethanes and polycarbonates*. PureAppl Chem 2011, 1. <http://dx.doi.org/10.1351/PAC-CON-11-06-14>
  • Dhakshinamoorthy Amarajothi, Sharmila Alagarsamy, Pitchumani Kasi: Layered Double Hydroxide-Supported L-Methionine-Catalyzed Chemoselective O-Methylation of Phenols and Esterification of Carboxylic Acids with Dimethyl Carbonate: A “Green” Protocol. Chem Eur J 2010, 16, 1128. <http://dx.doi.org/10.1002/chem.200902626>
  • Patil Yogesh P., Tambade Pawan J., Jagtap Sachin R., Bhanage Bhalchandra M.: Carbon dioxide: a renewable feedstock for the synthesis of fine and bulk chemicals. Front Chem Eng China 2010, 4, 213. <http://dx.doi.org/10.1007/s11705-009-0227-0>
  • Wang Dengfeng, Zhang Xuelan, Gao Yangyan, Xiao Fukui, Wei Wei, Sun Yuhan: Synthesis of dimethyl carbonate from methyl carbamate and methanol over lanthanum compounds. Fuel Proc Techn 2010, 91, 1081. <http://dx.doi.org/10.1016/j.fuproc.2010.03.017>
  • Xie Jiangang, Wu Chengyao, Christopher Branford White, Quan Jing, Zhu Limin: Ionic Liquids—Promoted S-Methylation of Thiols Utilizing Dimethyl Carbonate. Phosphorus Sulfur Silicon Relat Elem 2010, 186, 31. <http://dx.doi.org/10.1080/10426501003776939>
  • Samuilov A. Ya., Balabanova F. B., Kamalov T. A., Samuilov Ya. D., Konovalov A. I.: Quantum-Chemical Study on Reactions of Isocyanates with Linear Methanol Associates: III.* Reaction of Methyl Isocyanate with Linear Methanol Associates. Russ J Org Chem 2010, 46, 1452. <http://dx.doi.org/10.1134/S1070428010100027>
  • Juárez Raquel, Corma Avelino, García Hermenegildo: Towards a Phosgene-Free Synthesis of Aryl Isocyanates: Alcoholysis of N-phenylurea to N-phenyl-O-methyl Carbamate Promoted by Basic Metal Oxide Nanoparticles and Organocatalysts. Top Catal 2009, 52, 1688. <http://dx.doi.org/10.1007/s11244-009-9303-4>
  • Jagtap Sachin R., Bhor Malhari D., Bhanage Bhalchandra M.: Synthesis of dimethyl carbonate via transesterification of ethylene carbonate with methanol using poly-4-vinyl pyridine as a novel base catalyst. Catal Commun 2008, 9, 1928. <http://dx.doi.org/10.1016/j.catcom.2008.03.029>
  • Semak Vladislav, Boháč Andrej, Sališová Marta, Addová Gabriela, Danko Peter: Preparation of α-methyl-γ-butyrolactone: Mechanism of its formation and utilization in 2-methyl-1-tetralone synthesis. Chem Pap 2008, 62, 275. <http://dx.doi.org/10.2478/s11696-008-0023-1>
  • Abimanyu Haznan, Kim Chang Soo, Ahn Byoung Sung, Yoo Kye Sang: Synthesis of dimethyl carbonate by transesterification with various MgO–CeO2 mixed oxide catalysts. Catal Lett 2007, 118, 30. <http://dx.doi.org/10.1007/s10562-007-9091-z>
  • Wang Q. -S., Sun J. -H., Chu G. -Q., Yao X. -L., Chen C. -H.: Effect of LiPF6 on the thermal behaviors of four organic solvents for lithium ion batteries. J Therm Anal Calorim 2007, 89, 245. <http://dx.doi.org/10.1007/s10973-006-7534-1>
  • Fabbri Daniele, Baravelli Valentina, Chiavari Giuseppe, Prati Silvia, Finessi Emanuela: The influence of nanopowder metal oxides on the methylating activity of dimethyl carbonate in analytical pyrolysis. J Anal App Pyrol 2007, 79, 2. <http://dx.doi.org/10.1016/j.jaap.2006.11.004>
  • Wang Luying, Li Jiding, Lin Yangzheng, Chen Cuixian: Separation of dimethyl carbonate/methanol mixtures by pervaporation with poly(acrylic acid)/poly(vinyl alcohol) blend membranes. J Membr Sci 2007, 305, 238. <http://dx.doi.org/10.1016/j.memsci.2007.08.008>
  • Bernini Roberta, Mincione Enrico, Barontini Maurizio, Crisante Fernanda, Fabrizi Giancarlo, Gambacorta Augusto: Dimethyl carbonate: an environmentally friendly solvent for hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3, MTO) catalytic oxidations. Tetrahedron 2007, 63, 6895. <http://dx.doi.org/10.1016/j.tet.2007.04.039>
  • Bernini Roberta, Mincione Enrico, Crisante Fernanda, Barontini Maurizio, Fabrizi Giancarlo, Gentili Patrizia: Chemoselective and efficient carbomethoxylation of the alcoholic chain of phenols by dimethyl carbonate (DMC). Tetrahetron Lett 2007, 48, 7000. <http://dx.doi.org/10.1016/j.tetlet.2007.07.109>
  • Tian Jie-Sheng, Miao Cheng-Xia, Wang Jin-Quan, Cai Fei, Du Ya, Zhao Yuan, He Liang-Nian: Efficient synthesis of dimethyl carbonate from methanol, propylene oxide and CO2 catalyzed by recyclable inorganic base/phosphonium halide-functionalized polyethylene glycol. Green Chem 2007, 9, 566. <http://dx.doi.org/10.1039/b614259a>
  • Wang Qingsong, Sun Jinhua, Yao Xiaolin, Chen Chunhua: C80 Calorimeter Studies of the Thermal Behavior of LiPF6 Solutions. J Solution Chem 2006, 35, 179. <http://dx.doi.org/10.1007/s10953-006-9377-6>
  • Tian Jie-Sheng, Wang Jin-Quan, Chen Jian-Yu, Fan Jian-Guo, Cai Fei, He Liang-Nian: One-pot synthesis of dimethyl carbonate catalyzed by n-Bu4NBr/n-Bu3N from methanol, epoxides, and supercritical CO2. CATAL A GENERAL 2006, 301, 215. <http://dx.doi.org/10.1016/j.apcata.2005.12.002>
  • Wang Hui, Wang Mouhua, Zhang Wenyu, Zhao Ning, Wei Wei, Sun Yuhan: Synthesis of dimethyl carbonate from propylene carbonate and methanol using CaO–ZrO2 solid solutions as highly stable catalysts. Catal Today 2006, 115, 107. <http://dx.doi.org/10.1016/j.cattod.2006.02.031>
  • Wang Hui, Wang Mouhua, Liu Shuigang, Zhao Ning, Wei Wei, Sun Yuhan: Influence of preparation methods on the structure and performance of CaO–ZrO2 catalyst for the synthesis of dimethyl carbonate via transesterification. Journal of Molecular Catalysis A 2006, 258, 308. <http://dx.doi.org/10.1016/j.molcata.2006.05.050>
  • Ballivet-Tkatchenko Danielle, Chermette Henry, Plasseraud Laurent, Walter Olaf: Insertion reaction of carbon dioxide into Sn?OR bond. Synthesis, structure and DFT calculations of di- and tetranuclear isopropylcarbonato tin(iv) complexes. Dalton Trans 2006, 5167. <http://dx.doi.org/10.1039/b610812a>
  • Wang Hui, Wang Mouhua, Zhao Ning, Wei Wei, Sun Yuhan: CaO–ZrO2 Solid Solution: A Highly Stable Catalyst for the Synthesis of Dimethyl Carbonate from Propylene Carbonate and Methanol. Catal Lett 2005, 105, 253. <http://dx.doi.org/10.1007/s10562-005-8699-0>
  • Urieta José S., Mainar Ana M., Terrado Eva M., Pardo Juan I.: Solubilities of Nonpolar Gases in Dimethyl Carbonate and Diethyl Carbonate. J Chemical & Engineering Data 2005, 50, 512. <http://dx.doi.org/10.1021/je0496894>
  • Ouk Samedy, Thiébaud Sophie, Borredon Elisabeth, Chabaud Bernard: N‐Methylation of Nitrogen‐Containing Heterocycles with Dimethyl Carbonate. Synth Common 2005, 35, 3021. <http://dx.doi.org/10.1080/00397910500278578>
  • Lugo Luis, Comuñas María JP, López Enriqueta R, García Josefa, Fernández Josefa: Pressure and temperature dependence of the excess thermodynamic properties of binary dimethyl carbonate + n-octane mixtures. Can J Chem 2003, 81, 840. <http://dx.doi.org/10.1139/v03-090>