ChemSusChem

Cover image for Vol. 5 Issue 2

Special Issue: Flow Chemistry

February 13, 2012

Volume 5, Issue 2

Pages 213–439

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Review
    8. Minireview
    9. Communications
    10. Full Papers
    11. Review
    12. Communications
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      Cover Picture: Practical Synthesis of Photochromic Diarylethenes in Integrated Flow Microreactor Systems (ChemSusChem 2/2012) (page 213)

      Tatsuro Asai, Atsushi Takata, Dr. Aiichiro Nagaki and Prof. Dr. Jun-ichi Yoshida

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201290004

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      The synthesis of photochromic diarylethenes involves generating heteroaryllithium compounds by a halogen–lithium exchange reaction of heteroaryl halides, and subsequent reaction with octafluorocyclopentene. In a conventional batch macroreactor the reaction should be carried out at temperatures of −78 °C or lower, because heteroaryllithium compounds are often unstable and decompose at higher temperatures. The front cover features research by Jun-ichi Yoshida et al. (page 339), who report a practical method for the synthesis of photochromic diarylethenes by using integrated flow microreactor systems. Reactions can be conducted without using cryogenic conditions by virtue of effective temperature and residence-time control. Moreover, the synthesis of unsymmetrical diarylethenes, which is difficult to achieve using conventional batch macro systems, is accomplished.

  2. Inside Cover

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    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Review
    8. Minireview
    9. Communications
    10. Full Papers
    11. Review
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    1. Inside Cover: Ultrasound and Microstructures—A Promising Combination? (ChemSusChem 2/2012) (page 214)

      Dr.  S. Hübner, S. Kressirer, Dr.  D. Kralisch, Dr.  C. Bludszuweit-Philipp, K. Lukow, I. Jänich, A. Schilling, Dr.  H. Hieronymus, Dr.  C. Liebner and Dr. K. Jähnisch

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201290005

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      The combination of ultrasound and microstructures can increase interfacial areas between immiscible phases and thus enhance multiphase reactions. On page 279, Hübner and Jähnisch et al. report on the design, testing and evaluation of a modular setup for a continuous ultrasound supported liquid/liquid two-phase process in microstructured devices. Ultrasonication is effected indirectly via pressurized water as transmission medium for an improved energy input.

  3. Editorial

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    4. Editorial
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      Flow Chemistry: Enabling Technology in Drug Discovery and Process Research (pages 215–216)

      Prof. Thomas Wirth

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201200061

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      Editorial: Flow chemistry has now found its way into research and development, not only in academic institutions, but also in industry. This special issue of ChemSusChem is dedicated to flow chemistry, and the contributions showcase the diverse state-of-the-art of flow methodology in chemistry and the potential it certainly holds for future developments.

  4. Graphical Abstract

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      Graphical Abstract: ChemSusChem 2/2012 (pages 218–226)

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201290006

  5. News

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  6. Review

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    1. Recent Changes in Patenting Behavior in Microprocess Technology and its Possible Use for Gas–Liquid Reactions and the Oxidation of Glucose (pages 232–245)

      Ivana Dencic, Prof. Dr. Volker Hessel, Dr. Mart H. J. M. de Croon, Prof. Dr. Jan Meuldijk, Christianus W. J. van der Doelen and Kasper Koch

      Article first published online: 25 JAN 2012 | DOI: 10.1002/cssc.201100389

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      It got patential flow: Patenting behavior in microprocess technology has been changed during the last five years. The importance of multiphase reactions in chemical and pharmaceutical industry is shown by an increased number of device and process patents in this field. However, reviewed patents indicate that dealing with solid catalyst and flow control are still challenging tasks.

  7. Minireview

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    1. Application of Metal-Based Reagents and Catalysts in Microstructured Flow Devices (pages 247–255)

      Dr. Tamilselvi Chinnusamy, Dr. Salprima Yudha S , Dr. Markus Hager, Dr. Peter Kreitmeier and Prof. Dr. Oliver Reiser

      Article first published online: 24 JAN 2012 | DOI: 10.1002/cssc.201100444

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      Down and up: Downscaling reaction vessels and moving to a continuous flow approach have not only advanced many reactions with respect to efficiency and safety, but also offer a reliable solution for upscaling chemical transformations. Examples in this Minireview demonstrate the use of sensitive metal-based reagents, substrates, and catalysts at extreme temperatures.

  8. Communications

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    1. Ritter Reactions in Flow (pages 257–260)

      Logan Audiger, Kevin Watts, Simon C. Elmore, Dr. Richard I. Robinson and Prof. Thomas Wirth

      Article first published online: 1 DEC 2011 | DOI: 10.1002/cssc.201100372

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      Flow me a Ritter: Ritter reactions are performed in a simple microreactor setup using tert-butylacetate as versatile carbocation source. The protocol avoids the handling of large amounts of hot concentrated sulfuric acid as low concentrations are optimal for rapid access tert-butyl- or diphenylmethyl-protected amides.

    2. Organocatalyzed Epoxidation of Alkenes in Continuous Flow using a Multi-Jet Oscillating Disk Reactor (pages 261–265)

      Dr. Raffaele Spaccini, Dr. Lucia Liguori, Dr. Carlo Punta and Prof. Dr. Hans-René Bjørsvik

      Article first published online: 12 OCT 2011 | DOI: 10.1002/cssc.201100262

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      The times are changing: A batch process, the Minisci epoxidation, is transformed into a continuous-flow protocol for the selective aerobic radical epoxidation of alkenes. The use of a novel reactor type allows to considerably shorten reactor residence times. Experimental results suggest that two different reaction mechanisms exist for the oxidation: one for the batch conditions and a different one for flow synthesis protocol.

    3. Highly Efficient 1,4-Addition of Aldehydes to Nitroolefins: Organocatalysis in Continuous Flow by Solid-Supported Peptidic Catalysts (pages 266–269)

      Sándor B. Ötvös, Dr. István M. Mándity and Prof. Dr. Ferenc Fülöp

      Article first published online: 1 FEB 2012 | DOI: 10.1002/cssc.201100332

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      Michael's peptides: A simple and efficient continuous flow technique has been developed for the organocatalytic Michael reactions using solid-supported peptidic catalysts, readily synthesized and immobilized in one single step. Synthetically useful chiral γ-nitroaldehydes have been obtained in excellent yields and stereoselectivities within short reaction times, while catalyst reusability, the ease of product isolation, and facile scale-up enhances the efficacy of the technique.

    4. Room-Temperature, Acid-Catalyzed [2+2] Cycloadditions: Suppression of Side Reactions by using a Flow Microreactor System (pages 270–273)

      Kei Kurahashi, Prof. Yoshiji Takemoto and Prof. Kiyosei Takasu

      Article first published online: 27 OCT 2011 | DOI: 10.1002/cssc.201100373

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      Added value: The [2+2] cycloaddition of silyl enol ethers with α,β-unsaturated esters, catalyzed by the superstrong acid triflic imide (Tf2NH), at room temperature in a flow microreactor system is reported. The micororeactor method achieves the [2+2] cycloaddition of unstable silyl enol ethers and acrylates, which is unsuccessful in batch reactors, even at room temperature.

    5. The Oxygen-Mediated Synthesis of 1,3-Butadiynes in Continuous Flow: Using Teflon AF-2400 to Effect Gas/Liquid Contact (pages 274–277)

      Trine P. Petersen, Dr. Anastasios Polyzos , Dr. Matthew O'Brien, Dr. Trond Ulven, Dr. Ian R. Baxendale and Prof. Steven V. Ley

      Article first published online: 21 SEP 2011 | DOI: 10.1002/cssc.201100339

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      The gas is always greener: A continuous flow Glaser–Hay coupling reaction system, mediated by molecular oxygen, is developed based on a tube-in-tube gas/liquid reactor/injector. The system uses a semi-permeable Teflon AF-2400 membrane to effect rapid gas/liquid contact in flow, affording homogeneous solutions of oxygen. Measurements of out-gassing downstream of the back-pressure regulator indicate the onset of saturation is reached after about 16 seconds.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Review
    8. Minireview
    9. Communications
    10. Full Papers
    11. Review
    12. Communications
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    1. Ultrasound and Microstructures—A Promising Combination? (pages 279–288)

      Dr.  S. Hübner, S. Kressirer, Dr.  D. Kralisch, Dr.  C. Bludszuweit-Philipp, K. Lukow, I. Jänich, A. Schilling, Dr.  H. Hieronymus, Dr.  C. Liebner and Dr. K. Jähnisch

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201100369

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      A promising combination indeed: The combination of ultrasound and microstructures can increase interfacial areas between immiscible phases and thus enhance multiphase reactions. We report on the design, testing and evaluation of a novel modular setup for a continuous ultrasound-supported liquid/liquid two-phase process in microstructured devices. Ultrasonication is effected indirectly through pressurized water as transmission medium for an improved energy input.

    2. Prilezhaev Dihydroxylation of Olefins in a Continuous Flow Process (pages 289–292)

      Bas A. M. W. van den Broek, René Becker, Florian Kössl, Mariëlle M. E. Delville, Pieter J. Nieuwland, Kaspar Koch and Prof. Dr. Floris P. J. T. Rutjes

      Article first published online: 1 DEC 2011 | DOI: 10.1002/cssc.201100342

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      Olefins go with the flow: Prilezhaev dihydroxylation can be performed on a large scale in continuous flow microreactor systems in the oxidation of terminal and internal olefins. Major drivers for a continuous flow process include better control, improved safety, and a faster overall process, leading to a significantly higher throughput.

    3. Development of Polymeric Palladium-Nanoparticle Membrane-Installed Microflow Devices and their Application in Hydrodehalogenation (pages 293–299)

      Dr. Yoichi M. A. Yamada, Dr. Toshihiro Watanabe, Aya Ohno and Prof. Dr. Yasuhiro Uozumi

      Article first published online: 13 JAN 2012 | DOI: 10.1002/cssc.201100418

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      Streamlined nanoparticles: We developed a variety of polymeric Pd nanoparticle membrane-installed microflow devices. Instantaneous hydrodehalogenation of aryl halides can be achieved at short residence times and moderate temperatures using a safe, nonexplosive aqueous sodium formate to quantitatively afford the corresponding hydrodehalogenated products. PCB and PBB can also be fully decomposed under similar conditions to give a biphenyl.

    4. Transfer of the Epoxidation of Soybean Oil from Batch to Flow Chemistry Guided by Cost and Environmental Issues (pages 300–311)

      Dr. Dana Kralisch, Ina Streckmann, Dr. Denise Ott, Ulich Krtschil, Prof. Dr. Elio Santacesaria, Prof. Dr. Martino Di Serio, Vincenzo Russo, Lucrezia De Carlo, Dr. Walter Linhart, Engelbert Christian, Bruno Cortese, Dr. Mart H. J. M. de Croon and Prof. Dr. Volker Hessel

      Article first published online: 27 JAN 2012 | DOI: 10.1002/cssc.201100445

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      Transfer window: A holistic concept for sustainable process development through process intensification due to microprocess technology in combination with novel process windows is presented. Process modeling and simulation linked with simplified cost and lifecycle assessment provide valuable information to guide the ongoing design of a continuously running pilot-process for the epoxidation of soybean oil (see picture).

    5. Sequential Continuous Flow Processes for the Oxidation of Amines and Azides by using HOF⋅MeCN (pages 312–319)

      Christopher B. McPake, Dr. Christopher B. Murray and Prof. Graham Sandford

      Article first published online: 13 DEC 2011 | DOI: 10.1002/cssc.201100423

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      Oxidation in flow: The oxidation of amines and azides to the corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas–liquid/liquid–liquid continuous flow procedures are reported.

    6. A Solid-Supported Organocatalyst for Continuous-Flow Enantioselective Aldol Reactions (pages 320–325)

      Dr. Carles Ayats, Andrea H. Henseler and Prof. Dr. Miquel A. Pericàs

      Article first published online: 2 JAN 2012 | DOI: 10.1002/cssc.201100570

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      Go with the flow! A novel 4-(1-triazolyl)proline immobilized onto 8 % DVB-PS catalyzes highly stereoselective aldol reactions under continuous flow conditions with very low catalyst loading (TON up to 61). Up to four different enantiomerically pure aldol products can be sequentially produced in gram amounts with the same catalyst sample.

    7. TEMPO-Mediated Electrooxidation of Primary and Secondary Alcohols in a Microfluidic Electrolytic Cell (pages 326–331)

      Dr. Joseph T. Hill-Cousins, Dr. Jekaterina Kuleshova, Robert A. Green, Dr. Peter R. Birkin, Prof. Derek Pletcher, Toby J. Underwood, Dr. Stuart G. Leach and Prof. Richard C. D. Brown

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201100601

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      TEMPO and no salt in sight: A general procedure for the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-mediated electrooxidation of primary and secondary alcohols modified for application in a microfluidic electrolytic cell is described. The reaction is performed at ambient temperature in buffered aqueous tBuOH without additional electrolyte.

    8. Solid-Supported Gallium Triflate: An Efficient Catalyst for the Three-Component Ketonic Strecker Reaction (pages 332–338)

      Dr. Charlotte Wiles and Dr. Paul Watts

      Article first published online: 8 DEC 2011 | DOI: 10.1002/cssc.201100370

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      Trifle gallium supporters: A solid supported gallium triflate derivative is synthesized and screened for activity towards the ketonic Strecker reaction. The target α-aminonitriles are obtained in higher yield and purity compared to reactions reported in literature, for which the analogous homogeneous catalyst is used.

    9. Practical Synthesis of Photochromic Diarylethenes in Integrated Flow Microreactor Systems (pages 339–350)

      Tatsuro Asai, Atsushi Takata, Dr. Aiichiro Nagaki and Prof. Dr. Jun-ichi Yoshida

      Article first published online: 8 NOV 2011 | DOI: 10.1002/cssc.201100376

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      Too successful to be cool: An effective method for the synthesis of photochromic diarylethenes has been developed by using integrated flow microreactor systems. Reactions can be conducted without the need for cryogenic conditions by using these systems (see picture). The synthesis of unsymmetrical diarylethenes, which is difficult to achieve by using conventional macro batch systems, has also been accomplished.

  10. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Review
    8. Minireview
    9. Communications
    10. Full Papers
    11. Review
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    1. Homogeneous Photocatalytic Reactions with Organometallic and Coordination Compounds—Perspectives for Sustainable Chemistry (pages 352–371)

      Dr. Norbert Hoffmann

      Article first published online: 27 JAN 2012 | DOI: 10.1002/cssc.201100286

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      Solar powered: Photochemical conditions significantly alter the outcome of chemical reactions. Consequently, the scope of catalytic transformations with organometallic and coordination compounds is also considerably enlarged. This article provides a short overview on such reactions and their application to organic synthesis. The review also indicates synergistic effects of photochemistry and catalysis with perspectives for a sustainable chemistry.

  11. Communications

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    4. Editorial
    5. Graphical Abstract
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    7. Review
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    1. Hybrid Technologies for an Enhanced Carbon Recycling Based on the Enzymatic Reduction of CO2 to Methanol in Water: Chemical and Photochemical NADH Regeneration (pages 373–378)

      Prof. Angela Dibenedetto, Paolo Stufano, Dr. Wojciech Macyk, Tomasz Baran, Prof. Carlo Fragale, Prof. Mirco Costa and Prof. Michele Aresta

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201100484

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      Rocking chair enzyme: Chemical reducing agents (sodium dithionite) or bioglycerol (as H and e-donor under irradiation in the presence of ZnS-A as photocatalyst) are able to back-convert NADP+ into NADPH, which is used as e-donor in the enzymatic reduction of CO2 into CH3OH. In doing so, the molar ratio CH3OH/CO2 has been increased (without recycling of NADP+) using the photocatalyst.

    2. Flexible and Platinum-Free Dye-Sensitized Solar Cells with Conducting-Polymer-Coated Graphene Counter Electrodes (pages 379–382)

      Kun Seok Lee, Youngbin Lee, Prof. Jun Young Lee, Prof. Jong-Hyun Ahn and Prof. Jong Hyeok Park

      Article first published online: 13 JAN 2012 | DOI: 10.1002/cssc.201100430

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      Always wear a coat: On a plastic substrate graphene is coated with a conducting polymer (PEDOT), resulting in a flexible composite film. The film is used as counter electrode in dye-sensitized solar cells (DSSCs) instead of platinum/transparent conducting oxides (TCOs). The performance of the TCO- and platinum-free counter electrode rivals that of convenential DSSCs.

    3. Conversion of Hemicellulose to Furfural and Levulinic Acid using Biphasic Reactors with Alkylphenol Solvents (pages 383–387)

      Elif I. Gürbüz, Dr. Stephanie G. Wettstein and Prof. James A. Dumesic

      Article first published online: 24 JAN 2012 | DOI: 10.1002/cssc.201100608

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      Plans with plants: The hemicellulose fraction of lignocellulosic biomass is converted to furfural and levulinic acid using biphasic reactors with alkylphenol solvents that selectively partition furanic compounds from acidic aqueous solutions. The furfural and levulinic acid products are valuable compounds for a variety of chemical applications, and they serve as precursors for the synthesis of liquid transportation fuels.

    4. Design of Cellulose Dissolving Ionic Liquids Inspired by Nature (pages 388–391)

      Kazutaka Ohira, Dr. Yoshikazu Abe, Dr. Motoi Kawatsura, Kazuhiko Suzuki, Dr. Masahiro Mizuno, Prof. Dr. Yoshihiko Amano and Prof. Dr. Toshiyuki Itoh

      Article first published online: 19 JAN 2012 | DOI: 10.1002/cssc.201100427

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      Stimulating the hunger of enzymes: The design of an ionic liquid that has the ability to dissolve cellulose has been attempted from the viewpoint of a cellulase. N,N-diethyl-N-(2-methoxyethyl)-N-methylammonium alanine ([N221ME][Ala]) is a good solvent for cellulose. Dissolution in [N221ME][Ala] converts the crystalline structure of cellulose from Type I to II, which is known to be a form easily digested by cellulases.

    5. Highly Proton-Selective Biopolymer Layer-Coated Ion-Exchange Membrane for Direct Methanol Fuel Cells (pages 392–395)

      Dr. Sanna Kotrappanavar Nataraj, Dr. Chen-Hao Wang, Hsin-Chih Huang, He-Yun Du, Sea-Fu Wang, Ying-Chu Chen, Prof. Li-Chyong Chen and Dr. Kuei-Hsien Chen

      Article first published online: 3 FEB 2012 | DOI: 10.1002/cssc.201100366

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      Peels of an onion: New composite proton exchange membranes prepared through layer-by-layer coating of a biopolymer has shown superior methanol barrier properties, while maintaining a high affinity to proton transfer same time. The highly selective skin layer in the composite system significantly increases the fuel utilization efficiency in direct methanol fuel cells (DMFCs).

    6. Amine Synthesis through Mild Catalytic Hydrosilylation of Imines using Polymethylhydroxysiloxane and [RuCl2(arene)]2 Catalysts (pages 396–399)

      Bin Li, Dr. Jean-Baptiste Sortais, Prof. Dr. Christophe Darcel and Prof. Dr. Pierre H. Dixneuf

      Article first published online: 3 FEB 2012 | DOI: 10.1002/cssc.201100585

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      Tolerate silicone! The stable [RuCl2(p-cymene]2 complex is an efficient catalyst for the direct chemoselective hydrosilylation of functionalized aldimines and ketimines into amines, using polymethylhydroxysiloxane as an inexpensive, stable, and safe hydrosilane source. The catalysis operates in ethanol, under air at room temperature, and tolerates the ketone ester and alkene functionality.

    7. Hollow Carbon Nanospheres with a High Rate Capability for Lithium-Based Batteries (pages 400–403)

      Dr. Kun Tang, Dr. Robin J. White, Xiaoke Mu, Dr. Maria-Magdalena Titirici, Prof.Dr. Peter A. van Aken and Prof.Dr. Joachim Maier

      Article first published online: 19 JAN 2012 | DOI: 10.1002/cssc.201100609

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      Higher spheres: Hollow carbon nanospheres are prepared from glucose through a facile, sustainable hydrothermal method. Their morphology provides fast electron and lithium ion transport, which is reflected in a superior rate capability (100 mAh g−1 at 50 C) and good cycle stability. Nevertheless, these results provide direct evidence that not only lithium-ion insertion/extraction to the carbon layers occurs, but also that a surface reaction contributes to the high rate performance.

  12. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Review
    8. Minireview
    9. Communications
    10. Full Papers
    11. Review
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    1. Synthesis of Furfural from Xylose, Xylan, and Biomass Using AlCl3⋅6 H2O in Biphasic Media via Xylose Isomerization to Xylulose (pages 405–410)

      Yu Yang, Prof. Chang-Wei Hu and Prof. Mahdi M. Abu-Omar

      Article first published online: 7 FEB 2012 | DOI: 10.1002/cssc.201100688

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      Aluminum in microwaves: AlCl36 H2O successively hydrolyzes biomass hemicellulose to xylose, isomerizes xylose to xylulose, and dehydrates xylulose to furfural under microwave heating at 160 °C with yields in the range of 38–64 %, depending on the biomass feedstock. The use of a biphasic medium allows the recycling of AlCl36 H2O (which remains in the aqueous phase) for multiple cycles without loss of activity or selectivity (see figure).

    2. Application of the Sol–Gel Technique to Develop Synthetic Calcium-Based Sorbents with Excellent Carbon Dioxide Capture Characteristics (pages 411–418)

      Marcin Broda, Dr. Agnieszka M. Kierzkowska and Prof. Christoph R. Müller

      Article first published online: 1 FEB 2012 | DOI: 10.1002/cssc.201100468

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      Catch your breath: We report the development of synthetic calcium-based CO2 sorbents using a sol–gel technique. We are able to synthesize a nanostructured material that possesses a high surface area and pore volume and shows excellent CO2 capture characteristics over many cycles (see picture).

    3. New Biobased High Functionality Polyols and Their Use in Polyurethane Coatings (pages 419–429)

      Xiao Pan and Prof. Dean C. Webster

      Article first published online: 23 JAN 2012 | DOI: 10.1002/cssc.201100415

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      Sweet resins: Sucrose soyate-based polyols are made from sucrose esters of soybean oil through epoxidation and epoxide ring-opening reactions (see picture). These new biobased high functionality polyols are biomacromolecules with an innovative structural concept: well-defined compact structure, rigid sucrose core, and high hydroxyl group functionality.

    4. Solid Acid-Catalyzed Cellulose Hydrolysis Monitored by In Situ ATR-IR Spectroscopy (pages 430–437)

      Dr. Joseph Zakzeski, Dr. Ruud J. H. Grisel, Arjan T. Smit and Prof. Dr. Bert M. Weckhuysen

      Article first published online: 7 FEB 2012 | DOI: 10.1002/cssc.201100631

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      Vibrating acids: The solid acid-catalyzed hydrolysis of cellulose has been studied by using in situ ATR-IR spectroscopy. It is possible to monitor the formation and consumption of important products and intermediates by their distinctive vibrational characteristics under the reaction conditions.

  13. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Review
    8. Minireview
    9. Communications
    10. Full Papers
    11. Review
    12. Communications
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    1. You have free access to this content
      Preview: ChemSusChem 3/2012 (page 439)

      Article first published online: 15 FEB 2012 | DOI: 10.1002/cssc.201290008

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