ChemSusChem

Cover image for Vol. 3 Issue 11

November 22, 2010

Volume 3, Issue 11

Pages 1209–1315

  1. Cover Picture

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    4. News
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    1. Cover Picture: Synthesis of Furfural from Xylose and Xylan (ChemSusChem 11/2010) (page 1209)

      Dr. Joseph B. Binder, Jacqueline J. Blank, Anthony V. Cefali and Prof. Ronald T. Raines

      Version of Record online: 16 NOV 2010 | DOI: 10.1002/cssc.201090043

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      The cover picture is from the Communication by Binder et al. on p. 1268. Xylan, a polymer of xylose, is a primary component of birch and other hardwoods. The authors report on the one-step conversion of xylan into furfural, a commodity chemical. Their process, which uses mild conditions, offers an advantageous route from pentosans to renewable fuels and chemicals.

  2. Graphical Abstract

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    3. Graphical Abstract
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  3. News

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  4. Minireview

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    1. Lignin as Renewable Raw Material (pages 1227–1235)

      Prof. Francisco García Calvo-Flores and Prof. José A. Dobado

      Version of Record online: 13 SEP 2010 | DOI: 10.1002/cssc.201000157

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      Join my network of LignIn! Lignin is by far the most abundant substance based on aromatic moieties in nature, and the largest contributor to soil organic matter. For value-added applications of lignin to be improved, medium- and long-term conversion technologies must be developed, especially for the preparation of low-molecular-weight compounds as an alternative to the petrochemical industry.

  5. Highlight

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    1. Synthetic Glycolysis (pages 1237–1240)

      Prof. Raul F. Lobo

      Version of Record online: 20 SEP 2010 | DOI: 10.1002/cssc.201000186

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      Dealing in numbers: Recently, two groups separately reported what amounts to a synthetic version of glycolysis. The sum of these two reactions is equivalent to what is accomplished in living organisms by glycolysis in terms of the redistribution of oxidation states of the carbon, and is an important step in reproducing using chemical routes that living organisms accomplish daily.

  6. Communications

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    1. Nanoporous Nickel Spheres as Highly Active Catalyst for Hydrogen Generation from Ammonia Borane (pages 1241–1244)

      Chang-Yan Cao, Chao-Qiu Chen, Wei Li, Prof. Wei-Guo Song and Prof. Wei Cai

      Version of Record online: 28 OCT 2010 | DOI: 10.1002/cssc.201000229

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      Primal sphere: Nanoporous nickel spheres are prepared by an ethylene glycol-mediated process. The spheres have a large surface area, can be dispersed in water easily, and show a high catalytic activity towards the hydrolytic dehydrogenation of ammonia borane at room temperature.

    2. High Conductivity Perfluorosulfonic Acid Nanofiber Composite Fuel-Cell Membranes (pages 1245–1248)

      Dr. Jonghyun Choi, Dr. Ryszard Wycisk, Dr. Wenjing Zhang, Prof. Peter N. Pintauro, Dr. Kyung Min Lee and Prof. Patrick T. Mather

      Version of Record online: 8 OCT 2010 | DOI: 10.1002/cssc.201000220

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      Membranes are fabricated as a three-dimensional network of interconnected proton-conducting ionomer nanofibers that are embedded in an inert polymer matrix. The inert polymer controls water swelling of the nanofibers, thus permitting the fibers to have an ion-exchange capacity much greater than that which is practical in a homogeneous membrane. Such a high ion-exchange capacity membrane is needed for proton conduction in a hydrogen/air fuel cell that operates at high temperature and low humidity conditions.

    3. Lewis-Acidic Polyoxometalates as Reusable Catalysts for the Synthesis of Glucuronic Acid Esters under Microwave Irradiation (pages 1249–1252)

      Dr. Michael Bosco, Dr. Stéphanie Rat, Nathalie Dupré, Prof. Bernold Hasenknopf, Dr. Emmanuel Lacôte, Prof. Max Malacria, Dr. Pauline Rémy, Prof. Jose Kovensky, Prof. Serge Thorimbert and Dr. Anne Wadouachi

      Version of Record online: 4 NOV 2010 | DOI: 10.1002/cssc.201000218

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      Chemoselective microwave-assisted transesterification of 6,1-lactone derived from glucuronic acid is catalyzed by reusable Dawson-type polyoxometalates. These catalysts allow the formation of pseudo-disaccharides from easily available precursors. This permits the expeditious assembly of promising building blocks from precursors obtained from biomass, with easy recycling of the catalyst.

    4. Redox-Responsive Switching in Bacterial Respiratory Pathways Involving Extracellular Electron Transfer (pages 1253–1256)

      Dr. Huan Liu, Shoichi Matsuda, Dr. Souichiro Kato, Prof. Kazuhito Hashimoto and Dr. Shuji Nakanishi

      Version of Record online: 8 OCT 2010 | DOI: 10.1002/cssc.201000213

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      Go with the flow:Shewanella is capable of transferring respiratory electrons to solid-state metal-oxides through physical contact (direct pathway) or by using electron shuttles (indirect pathway). We reveal, by using an electrochemical approach, that these pathways are switched depending on the redox state of the cytochromes.

    5. The Effect of Imidazolium Ionic Liquid on the Dehydration of Fructose to 5-Hydroxymethylfurfural, and a Room Temperature Catalytic System (pages 1257–1259)

      Linke Lai and Dr. Yugen Zhang

      Version of Record online: 1 SEP 2010 | DOI: 10.1002/cssc.201000201

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      The catalytic dehydration of fructose into 5-hydroxymethylfurfural is conducted in an HCl–imidazolium ionic liquid (catalyst–solvent) system, in ambient conditions. High yields and excellent recyclability make the system a promising choice for fructose dehydration. DFT calculations suggest that the solvent “switches” the dehydration from thermodynamically unfavorable into a thermodynamically favorable reaction.

    6. Spinel LiCo0.7Mn1.3O4 Nanowire Clusters as Electrode Materials (pages 1260–1263)

      Sanghan Lee, Sookyung Jeong and Prof. Jaephil Cho

      Version of Record online: 29 OCT 2010 | DOI: 10.1002/cssc.201000190

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      Knowledge cluster: Spinel LiCo0.7Mn1.3O4 nanowire clusters, with each nanowire having a diameter of ca. 100 nm, result from a hydrothermal reaction between LiOH and Co0.35Mn0.65O2, obtained from K-birnessite at 150 °C. The nanowires demonstrate a good cycling stability and rate capability (improved by more than 50 %, compared to the bulk counterpart) in spite of their higher electrode density (3.4 g mL−1) over a wide voltage range, between 4.7 V and 2 V.

    7. Ionic-Liquid-Stabilized Rhodium Nanoparticles for Citral Cyclodehydration (pages 1264–1267)

      Xian-Yang Quek, Dr. Yejun Guan, Prof. Rutger A. van Santen and Prof. Emiel J. M. Hensen

      Version of Record online: 30 AUG 2010 | DOI: 10.1002/cssc.201000188

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      Smells nice, too: The cyclodehydration of citral is achieved by using rhodium nanoparticles dispersed in an imidazolium-based ionic liquid. p-Cymene, p-α-dimethylstyrene, and limonene are obtained with selectivity greater than 75 %. The interaction between the imidazolium cations and the metal nanoparticles results in an acidic catalyst, which plays a similar function as a mineral acid but has a one order of magnitude higher activity.

    8. Synthesis of Furfural from Xylose and Xylan (pages 1268–1272)

      Dr. Joseph B. Binder, Jacqueline J. Blank, Anthony V. Cefali and Prof. Ronald T. Raines

      Version of Record online: 10 SEP 2010 | DOI: 10.1002/cssc.201000181

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      Furans from pentoses: Pentose-derived furfural is a commodity chemical produced from lignocellulose. A new route to furfural from renewable carbohydrates uses chromium catalysts under mild conditions to avail a chemical mechanism distinct from the usual acid catalysis. Applicable to both xylose and xylan, this new method offers an advantageous route to biomass-derived chemicals.

    9. Facile Single-Step Conversion of Macroalgal Polymeric Carbohydrates into Biofuels (pages 1273–1275)

      Bora Kim, Jaewon Jeong, Dr. Seunghan Shin, Dr. Dohoon Lee, Dr. Sangyong Kim, Hyo-Jin Yoon and Dr. Jin Ku Cho

      Version of Record online: 22 OCT 2010 | DOI: 10.1002/cssc.201000192

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      Red macroalgae-derived agar is a renewable and sustainable resource. For the synthesis of HMF under solid Brønsted acid conditions, agar shows a unique reaction pattern and affords higher yields than land plant-based polymeric carbohydrates. Agar can be directly converted into next-generation biofuels by one-pot reactions and readily isolated by using a general workup procedure, which is crucial for a large-scale process.

    10. N-Methylephedrium Salts as Chiral Surfactants for Asymmetric Hydrogenation in Neat Water with Rhodium(0) Nanocatalysts (pages 1276–1279)

      Elodie Guyonnet Bilé, Dr. Audrey Denicourt-Nowicki, Rita Sassine, Patricia Beaunier, Franck Launay and Prof. Alain Roucoux

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/cssc.201000206

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      A new family of chiral surfactants derived from N-methylephedrine possessing different counter-ions (Br, equation image, (S)-(−)-lactate) is easily prepared and used as efficient protective agents of rhodium(0) nanoparticles. The resulting, well-characterized materials prove to be active catalysts in the hydrogenation of ethylpyruvate in neat water, with modest enantiomeric excesses.

    11. A Green and Highly Selective Oxidation of Alcohols by Fluorous Silica Gel-Supported Gold Nanoparticles in Aqueous H2O2 under Base-Free Conditions (pages 1280–1284)

      Liang Wang, Prof. Wen-bin Yi and Prof. Chun Cai

      Version of Record online: 9 SEP 2010 | DOI: 10.1002/cssc.201000170

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      Highly efficient and selective oxidation of alcohols is achieved in aqueous H2O2 using supported gold nanoparticles as catalyst. In addition, the catalyst can be readily recovered by a simple work-up and reused several times without significant loss of activity.

    12. Rapid Determination of Lignin Content via Direct Dissolution and 1H NMR Analysis of Plant Cell Walls (pages 1285–1289)

      Dr. Nan Jiang, Dr. Yunqiao Pu and Prof. Arthur J. Ragauskas

      Version of Record online: 30 SEP 2010 | DOI: 10.1002/cssc.201000120

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      A rapid and efficient process for the measurement of lignin content in the plant cell walls is reported. The described method can be used to analyze ball- or Wiley-milled samples at a microscale via direct dissolution and 1H NMR analysis of biomass using perdeuterated pyridinium chloride/[D6]DMSO bisolvent system.

  7. Full Papers

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    1. Improving Sustainability in Ene–Yne Cross-Metathesis for Transformation of Unsaturated Fatty Esters (pages 1291–1297)

      Virginie Le Ravalec, Antoine Dupé, Dr. Cédric Fischmeister and Dr. Christian Bruneau

      Version of Record online: 24 SEP 2010 | DOI: 10.1002/cssc.201000212

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      Environmentally ene–yne: A ruthenium-catalyzed ene–yne cross-metathesis reaction is performed with stoichiometric amounts of terminal olefins and alkynes. The alkyne is added to the reaction mixture continuously. The protocol allows ene–yne cross-metathesis reaction to be carried out with long-chain terminal olefins and with internal olefins after shortening by ethenolysis in dimethyl carbonate as solvent.

    2. Hydrolysis of Cellulose by Using Catalytic Amounts of FeCl2 in Ionic Liquids (pages 1298–1303)

      Dr. Furong Tao , Dr. Huanling Song and Prof. Lingjun Chou

      Version of Record online: 8 OCT 2010 | DOI: 10.1002/cssc.201000184

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      The use of FeCl2 as catalyst in an ionic liquid, 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate (IL-1), is found to be effective for the hydrolysis of microcrystalline cellulose (MCC). The conversion reaches >84 %, and yields of 5-hydroxymethylfurfural (HMF) and furfural of 34 % and 19 %, respectively, are achieved; small amounts of levulinic acid and total reducing sugars are also generated.

    3. Acid-Catalyzed Dehydration of Fructose and Inulin with Glycerol or Glycerol Carbonate as Renewably Sourced Co-Solvent (pages 1304–1309)

      Maud Benoit, Yoan Brissonnet, Dr. Erwan Guélou, Dr. Karine De Oliveira Vigier, Dr. Joël Barrault and Dr. François Jérôme

      Version of Record online: 30 SEP 2010 | DOI: 10.1002/cssc.201000162

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      Super subs: The amount of the ionic liquid [BMIM]Cl required for the acid-catalyzed dehydration of fructose and inulin into HMF, over Amberlyst 70 resin as solid acid catalyst, can be reduced by substituting it (up to 90 wt %) with large amounts of glycerol or glycerol carbonate; cheap co-solvents from renewable sources.

  8. Preview

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    2. Cover Picture
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    7. Communications
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      Preview: ChemSusChem 12/2010 (page 1315)

      Version of Record online: 16 NOV 2010 | DOI: 10.1002/cssc.201090046

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