ChemSusChem

Cover image for Vol. 4 Issue 8

August 22, 2011

Volume 4, Issue 8

Pages 985–1175

  1. Cover Picture

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    4. News
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    1. Cover Picture: Remarkable Impact of Water on the Discharge Performance of a Silicon–Air Battery (ChemSusChem 8/2011) (page 985)

      Gil Cohn, Prof. Digby D. Macdonald and Prof. Yair Ein-Eli

      Version of Record online: 22 AUG 2011 | DOI: 10.1002/cssc.201190032

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      The power of water: The cover picture illustrates the remarkable impact of the addition of water to ionic-liquid-based electrolyte on the discharge performance of Si–air batteries. The maximum cell discharge capacity is obtained with the addition of a few drops of water, where the cell capacity is substantially increased, compared to the cell capacity obtained with a pure ionic liquid electrolyte. This improvement is attributed to a shift in the reaction zone, leading to a formation of SiO2 in the bulk electrolyte, instead of solely being formed at the air electrode in a pure electrolyte. In a Full Paper by Cohn et al. on p. 1124, it is shown that water molecules play a major role in the battery discharge process of Si–air batteries, and thus, greatly affect the efficiency of the cell. This finding may have tremendous practical implications, because of the difficulty and cost of removing residual water from ionic liquids being used as battery electrolytes.

  2. Graphical Abstract

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  3. News

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    4. News
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  4. Reviews

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    1. Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural (pages 1002–1016)

      Dr. Reetta Karinen, Kati Vilonen and Prof. Dr. Marita Niemelä

      Version of Record online: 4 JUL 2011 | DOI: 10.1002/cssc.201000375

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      Biomass is no longer only a raw material for traditional mechanical or chemical conversion, but also a feedstock for biorefineries. Furfural and hydroxymethylfurfural are important biorefinery building blocks. The efficient synthesis of them, consistent with the principles of green chemistry, could rely on active and stable water-tolerant solid acid catalysts. This Review describes recent progress in this area.

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      Renewable Chemicals: Dehydroxylation of Glycerol and Polyols (pages 1017–1034)

      Jeroen ten Dam and Dr. Ulf Hanefeld

      Version of Record online: 22 AUG 2011 | DOI: 10.1002/cssc.201100162

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      Glycerol and polyols from biomass need to be de-functionalized in order to be a feedstock for the chemical industry. A fundamentally different approach to chemistry thus becomes necessary, since the traditionally employed oil-based chemicals normally lack functionality. A new chemical toolbox needs to be designed to guarantee the demands of future generations.

  5. Minireview

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    1. Reduction Reactions in Green Solvents: Water, Supercritical Carbon Dioxide, and Ionic Liquids (pages 1035–1048)

      Dr. Luis Álvarez de Cienfuegos, Dr. Rafael Robles, Dr. Delia Miguel, Dr. José Justicia and Dr. Juan M. Cuerva

      Version of Record online: 8 AUG 2011 | DOI: 10.1002/cssc.201100134

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      Solving problems: Reduction reactions are important chemical transformations, widely used on both the laboratory and industrial scale. Thus, the importance of these chemical transformations necessitates research towards alternative, greener solvent systems, to reduce any negative impact on the environment. This Minireview is focused on three alternatives for conducting reduction reactions: water, supercritical carbon dioxide, and ionic liquids.

  6. Communications

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    1. 3-Deoxy-glucosone is an Intermediate in the Formation of Furfurals from D-Glucose. (pages 1049–1051)

      Dr. Harishchandra Jadhav, Dr. Christian Marcus Pedersen, Prof. Theis Sølling and Prof. Mikael Bols

      Version of Record online: 29 JUN 2011 | DOI: 10.1002/cssc.201100249

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      The acid-catalyzed dehydration of glucose to hydroxymethylfurfural (6) can occur via two possible mechanisms. 3-deoxy-D-erythro-hex-2-ulose (3) is found to be an intermediate in the formation of 6 from glucose (1). This finding implies that elimination of the glucose 3-OH group is the important step, rather than isomerization of the carbonyl group.

    2. α,ω-Functionalized C19 Monomers (pages 1052–1054)

      Guido Walther, Dr. Jens Deutsch, Dr. Andreas Martin, Dr. Franz-Erich Baumann, Dirk Fridag, Dr. Robert Franke and Dr. Angela Köckritz

      Version of Record online: 7 JUN 2011 | DOI: 10.1002/cssc.201100187

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      High-oleic sunflower oil, a renewable resource, is efficiently incorporated into a sustainable and green chemical process: the synthesis of α,ω-functionalized C19 monomers. These monomers, derived from dimethyl 1,19-nonadecanedioate as a novel platform chemical, may find use as feedstock materials for the polymer industry.

    3. Conversion of Ethanol into Polyolefin Building Blocks: Reaction Pathways on Nickel Ion-loaded Mesoporous Silica (pages 1055–1058)

      Prof. Masakazu Iwamoto, Dr. Kouji Kasai and Dr. Teruki Haishi

      Version of Record online: 20 JUN 2011 | DOI: 10.1002/cssc.201100168

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      Ethanol to olefins: Very fast, selective, and stable formation of ethene, propene, and butenes from ethanol is achieved on Ni-MCM-41 at 573–723 K, without deactivation. Two reaction pathways via diethyl ether and acetaldehyde are suggested. The results are relevant for the possible use of bioethanol as a renewable material for the production of plastics.

    4. Transesterification to Biodiesel with Superhydrophobic Porous Solid Base Catalysts (pages 1059–1062)

      Dr. Fujian Liu, Dr. Wei Li, Dr. Qi Sun, Dr. Longfeng Zhu, Dr. Xiangju Meng, Prof. Yi-Hang Guo and Prof. Feng-Shou Xiao

      Version of Record online: 30 MAY 2011 | DOI: 10.1002/cssc.201100166

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      Super combo: Superhydrophobic and porous solid bases are synthesized by co-polymerization of divinylbenzene (DVB) and 1-vinylimidazolate (VI). The materials show higher activities towards the transesterification of tripalmitin with methanol than conventional bases and VI mono-/polymer. Their performance is attributed to the synergy of superhydrophobicity combined with active VI sites. These catalysts also remain very active upon recycling.

    5. Noncovalent Interactions of Metalloporphyrins with Polyamidoamine Dendrimers Give Rise to Efficient Catalytic Systems for H2O2 Oxidation of Trichlorophenol in Water (pages 1063–1067)

      Dr. Qizhi Ren, Zhongsheng Hou, Ying Wang, Hong Zhang and Dr. Shiping Yang

      Version of Record online: 12 JUL 2011 | DOI: 10.1002/cssc.201100108

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      A noncovalent FeTPPS/dendrimer system is an efficient and stable catalyst for the oxidation of trichlorophenol in water with H2O2. A very high total turnover number is obtained and no obvious blenching is observed. The catalytic system can be recycled several times with a only slight decrease of the catalytic activity, underlining the robustness of the catalyst.

    6. A Synthetic Metabolic Pathway for Production of the Platform Chemical Isobutyric Acid (pages 1068–1070)

      Prof. Kechun Zhang, Adam P. Woodruff, Mingyong Xiong, Jun Zhou and Yogesh K. Dhande

      Version of Record online: 8 JUL 2011 | DOI: 10.1002/cssc.201100045

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      Go green: Isobutyric acid is a high-volume industrial chemical produced from non-sustainable petroleum feedstocks and toxic materials. A synthetic metabolic pathway is constructed in E. coli to enable the biosynthesis of this compound from glucose, a renewable carbon source. The biosynthetic approach is an attractive option from both an economical and environmental point of view.

    7. Selective Hydrogenation of Trans,Trans-Muconic Acid to Adipic Acid over a Titania-Supported Rhenium Catalyst (pages 1071–1073)

      Dr. Xiaoyan She, Heather M. Brown, Prof. Dr. Xiao Zhang, Prof. Dr. Birgitte K. Ahring and Prof. Dr. Yong Wang

      Version of Record online: 17 JUN 2011 | DOI: 10.1002/cssc.201100020

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      Metal oxide-supported rhenium catalysts are highly active and selective for the hydrogenation of trans,trans-muconic acid to adipic acid. High yields to adipic acid are achieved (ca. 88 %) over Re/TiO2 catalyst at 210 °C after 5 h, using methanol as solvent. The selectivity of the rhenium-catalyzed hydrogenation of muconic acid to adipic acid may be further enhanced by using acetone or larger alcohols as solvent in comparison to methanol.

    8. Biobutanol Separation with the Metal–Organic Framework ZIF-8 (pages 1074–1077)

      Julien Cousin Saint Remi, Tom Rémy, Vincent Van Hunskerken, Stijn van de Perre, Tim Duerinck, Dr. Michael Maes, Prof. Dr. Dirk De Vos, Dr. Elena Gobechiya, Prof. Dr. Christine E. A. Kirschhock, Prof. Dr. Gino V. Baron and Prof. Dr. Joeri F. M. Denayer

      Version of Record online: 8 JUL 2011 | DOI: 10.1002/cssc.201100261

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      Keep ′em separated: Bioalcohols are alternatives to petroleum-based chemicals. Particularly biobutanol is an interesting compound, with properties superior to bioethanol. It is difficult, however, to separate biobutanol from the mixtures produced by the fermentation of biomass. This Communication describes a zeolitic imidazolate framework suitable for the separation of biobutanol from fermentation broths by adsorption.

    9. Production of Biofuels from Cellulose and Corn Stover Using Alkylphenol Solvents (pages 1078–1081)

      Dr. David Martin Alonso, Dr. Stephanie G. Wettstein, Dr. Jesse Q. Bond, Prof. Thatcher W. Root and Prof. James A. Dumesic

      Version of Record online: 30 JUN 2011 | DOI: 10.1002/cssc.201100256

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      Alkylphenol solvents allow a more effective production of biofuels from corn stover by enabling selective extraction and hydrogenation of levulinic acid to γ-valerolactone, and by increasing the final concentration of GVL through successive extraction/hydrogenation steps. The versatility of alkylphenol solvents may lead to their use in other biomass conversion processes utilizing mineral acids for biomass deconstruction.

    10. An Inorganic Iodine-Catalyzed Oxidative System for the Synthesis of Benzimidazoles Using Hydrogen Peroxide under Ambient Conditions (pages 1082–1086)

      Chenjie Zhu and Prof. Yunyang Wei

      Version of Record online: 18 AUG 2011 | DOI: 10.1002/cssc.201100228

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      A simple and efficient catalytic oxidative system for the synthesis of benzimidazole derivatives with H2O2 in the presence of catalytic amounts of Bu4NI is developed. The formation of highly reactive iodine (III) intermediate [Bu4N]+[IO2] is detected by ESI–MS for the first time, and a possible mechanism for the oxidation is proposed.

    11. A Li–Liquid Cathode Battery Based on a Hybrid Electrolyte (pages 1087–1090)

      Dr. Yarong Wang, Dr. Yonggang Wang and Prof. Haoshen Zhou

      Version of Record online: 22 AUG 2011 | DOI: 10.1002/cssc.201100201

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      Thirsty battery: We introduce a Li–liquid cathode battery which employs an inexpensive aqueous solution of the Fe3+/Fe2+ redox couple as both cathode and electrolyte. The liquid cathode can be recovered through electric or chemical “charging” after discharge of the battery and, depending on the targeted utilization, can be switched to be operated in either a static or a flow mode.

    12. Mild and Cost-Effective One-Pot Synthesis of Pure Single-Crystalline β-Ag0.33V2O5 Nanowires for Rechargeable Li-ion Batteries (pages 1091–1094)

      Dr. Wen Hu, Prof. Dr. Xin-bo Zhang, Dr. Yong-liang Cheng, Dr. Chao-yong Wu, Dr. Feng Cao and Dr. Li-min Wang

      Version of Record online: 29 JUL 2011 | DOI: 10.1002/cssc.201100124

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      Crunch time! Or? Pure, single-crystalline β-Ag0.33V2O5 nanowires are prepared to serve as electrode materials in lithium-ion batteries. In contrast to stoichiometric counterparts, the structure of the β-Ag0.33V2O5 nanowires is retrievable upon repeated lithium-ion displacement/intercalation reactions. The proposed strategy to stabilize the crystal structure of electrode materials based on a displacement/intercalation mechanism shows promise for application in rechargeable lithium-ion batteries.

    13. Direct Oxidation of Methane to Hydrogen Peroxide and Organic Oxygenates in a Double Dielectric Plasma Reactor (pages 1095–1098)

      Dr. Juncheng Zhou, Yue Xu, Xu Zhou, Junsong Gong, Prof. Yanhua Yin, Prof. Hanyong Zheng and Prof. Hongchen Guo

      Version of Record online: 20 JUN 2011 | DOI: 10.1002/cssc.201100093

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      Seeing double: The synthesis of hydrogen peroxide, an environmentally benign oxidizing agent, from methane in a plasma reactor is investigated. The selectivity of the methane oxidation can be shifted away from H2O and COx towards high yields of H2O2 and organic oxygenates by changing the structure of plasma reactor, from using a single dielectric to using a double one (see figure).

  7. Full Papers

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    1. In Situ X-Ray Spectromicroscopy Investigation of the Material Stability of SOFC Metal Interconnects in Operating Electrochemical Cells (pages 1099–1103)

      Prof. Benedetto Bozzini, Dr. Elisabetta Tondo, Dr. Mauro Prasciolu, Dr. Matteo Amati, Dr. Majid Kazemian Abyaneh, Dr. Luca Gregoratti and Dr. Maya Kiskinova

      Version of Record online: 21 JUN 2011 | DOI: 10.1002/cssc.201100140

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      Back to basics: In situ scanning photoelectron microscopy study of electrochemically induced processes, occurring in a model SOFC Cr/Ni/YSZ/Ni/Cr system (see figure), reveals the effect of reaction temperature and applied potentials on the lateral distribution of Cr and Ni across the cell and on the evolution of the chemical state of the cell constituents.

    2. Telomerisation of 1,3-Butadiene with 1,4:3,6-Dianhydrohexitols: An Atom-Economic and Selective Synthesis of Amphiphilic Monoethers from Agro-Based Diols (pages 1104–1111)

      Jonathan Lai, Sandra Bigot, Dr. Mathieu Sauthier, Dr. Valérie Molinier, Dr. Isabelle Suisse, Prof.  Yves Castanet, Prof.  Jean-Marie Aubry and Prof.  André Mortreux

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/cssc.201100135

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      Selective synthesis: The telomerisation of 1,3-butadiene with a Pd/TPPTS catalytic system in water or an organic solvent is used for the synthesis of C8 ethers from agro-based diols, 1,4:3,6-dianhydrohexitols. Under water/oil biphasic reaction conditions in the presence of inorganic bases as promoters improve the conversion rates in the selective synthesis of monoethers.

    3. Cobalt Monolayer Islands on Ag(111) for ORR Catalysis (pages 1112–1117)

      Dr. Francesca Loglio, Dr. Elisa Lastraioli, Dr. Claudio Bianchini, Prof. Claudio Fontanesi, Dr. Massimo Innocenti, Dr. Alessandro Lavacchi, Dr. Francesco Vizza and Prof. Maria Luisa Foresti

      Version of Record online: 3 JUN 2011 | DOI: 10.1002/cssc.201100092

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      Robinson quest: Cobalt islands are achieved by using templates obtained by selective desorption of 3-mercaptopropionic acid from a binary self-assembled monolayer formed with DDT on Ag(111). Cobalt can be deposited on silver by using surface limited redox replacement: A ZnUPD layer previously electrodeposited in the holes of SAMs is replaced by the more noble metal Co. The catalytic effect on the oxygen reduction reaction depends on the Co/Ag ratio.

    4. Ionic Liquid Catalysed Synthesis of β-Hydroxy Ketones (pages 1118–1123)

      Dr. Sanjib Kumar Karmee and Dr. Ulf Hanefeld

      Version of Record online: 29 JUN 2011 | DOI: 10.1002/cssc.201100083

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      Edible accelerant: By utilising the food derivative choline hydroxide as a catalyst, a range of aldehydes can be selectively converted into their corresponding β-hydroxy ketones (see picture). In this solvent-free reaction, the elimination of water can be suppressed and the desired β-hydroxy ketones are obtained under very mild conditions.

    5. Remarkable Impact of Water on the Discharge Performance of a Silicon–Air Battery (pages 1124–1129)

      Gil Cohn, Prof. Digby D. Macdonald and Prof. Yair Ein-Eli

      Version of Record online: 15 JUL 2011 | DOI: 10.1002/cssc.201100169

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      Changing the chemical reaction zone: The addition of water to an ionic liquid electrolyte is found to be responsible for shifting the silica formation reaction zone from the carbonaceous air electrode into the bulk electrolyte. This process improves the cell capacity by 40 %. Other effects of water addition are also discussed.

    6. Efficient Synthetic Protocols in Glycerol under Heterogeneous Catalysis (pages 1130–1134)

      Prof. Giancarlo Cravotto, Laura Orio, Dr. Emanuela Calcio Gaudino, Dr. Katia Martina, Prof. Dorith Tavor and Prof. Adi Wolfson

      Version of Record online: 18 AUG 2011 | DOI: 10.1002/cssc.201100106

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      Sweet success: The properties of glycerol as a reaction medium are improved by ultrasound and/or microwave irradiation. Transfer hydrogenation, palladium-catalyzed Suzuki couplings, and Barbier reactions are investigated under classic and non-conventional conditions. Glycerol proves to be a greener, inexpensive, and safer alternative to classic volatile organic solvents.

    7. Synthesis of Soybean Oil-Based Thiol Oligomers (pages 1135–1142)

      Jennifer F. Wu, Shashi Fernando, Dimuthu Weerasinghe, Dr. Zhigang Chen and Prof. Dean C. Webster 

      Version of Record online: 25 MAY 2011 | DOI: 10.1002/cssc.201100071

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      Glorious soybeans: The thermal, free radical initiated thiol–ene reaction between thiols and vegetable oil generates high molecular weight, oil-based, and multi-functional thiols.

    8. Glycerol Hydrogenolysis Promoted by Supported Palladium Catalysts (pages 1143–1150)

      Prof. Maria Grazia Musolino, Dr. Luciano Antonio Scarpino, Dr. Francesco Mauriello and Prof. Rosario Pietropaolo

      Version of Record online: 28 JUN 2011 | DOI: 10.1002/cssc.201100063

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      All that glycerols is not gold: Glycerol hydrogenolysis, with high conversion and selectivity, promoted by supported palladium substrates in isopropanol and dioxane at low H2 pressure is reported for the first time.

    9. Ethanol Dehydration to Ethylene in a Stratified Autothermal Millisecond Reactor (pages 1151–1156)

      Michael J. Skinner, Edward L. Michor, Prof. Wei Fan, Prof. Michael Tsapatsis, Prof. Aditya Bhan and Prof. Lanny D. Schmidt

      Version of Record online: 10 AUG 2011 | DOI: 10.1002/cssc.201100026

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      Successful oxygen removal: Noble metals can be successfully paired with zeolites in a stratified autothermal reactor to remove oxygen from biomass model compounds. The stratified reactor with an upstream oxidation zone containing Pt-coated Al2O3 beads and a downstream dehydration zone consisting of H-ZSM-5 zeolite sheets deposited on Al2O3 monoliths, decomposes and deoxygenates ethanol (see figure).

    10. Reformer and Membrane Modules for Methane Conversion: Experimental Assessment and Perspectives of an Innovative Architecture (pages 1157–1165)

      Dr. Marcello De Falco, Annarita Salladini and Gaetano Iaquaniello

      Version of Record online: 8 AUG 2011 | DOI: 10.1002/cssc.201100009

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      Above the RMM: Reformer and palladium-based membrane modules are the basis for a two-step test plant with an H2 capacity of 20 Nm3 h−1, designed and constructed to investigate the potential of such a design at an industrial level. Experimental data gathered over 1000 h of testing is examined and processed in order to optimize the overall architecture.

    11. A Study of the Acid-Catalyzed Hydrolysis of Cellulose Dissolved in Ionic Liquids and the Factors Influencing the Dehydration of Glucose and the Formation of Humins (pages 1166–1173)

      Sean J. Dee and Prof. Alexis T. Bell

      Version of Record online: 2 AUG 2011 | DOI: 10.1002/cssc.201000426

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      Attractive qualities: An investigation into the hydrolysis of dissolved microcrystalline cellulose in ionic liquids catalyzed by mineral acids is described. Experimental observations are related to proposed mechanisms for the formation of glucose, 5-hydroxymethylfurfural, and humins (see scheme).

  8. Preview

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
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    5. Reviews
    6. Minireview
    7. Communications
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    1. You have free access to this content
      Preview: ChemSusChem 9/2011 (page 1175)

      Version of Record online: 22 AUG 2011 | DOI: 10.1002/cssc.201190031

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