ChemSusChem

Cover image for Vol. 5 Issue 4

April 2012

Volume 5, Issue 4

Pages 601–799

  1. Cover Picture

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      Cover Picture: Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid (ChemSusChem 4/2012) (page 601)

      Dr. Yuki Tobimatsu, Dr. Sasikumar Elumalai, Dr. John H. Grabber, Christy L. Davidson, Prof. Dr. Xuejun Pan and Prof. Dr. John Ralph

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cssc.201290013

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      Easier biomass processing may be realized by inducing plants to produce easilycleavable ester linkages in the backbone of the lignin polymer, for example, by introducing hydroxycinnamate conjugates into the lignification monomer stream. This reduces the recalcitrance of the lignin polymer, allowing it to be readily depolymerized away from the polysaccharides by anticipated biomass processing; saccharification to simple sugars can therefore be achieved with lower energy inputs. The cover image features research by Tobimatsu et al. (Page 676) who report in vitro lignification using a prospective strategic lignin monomer replacement, rosmarinic acid. Rosmarinic acid is a dominant hydroxycinnamate found in many species of the Lamiaceae plant family, such as rosemary (Rosmarinus officinalis), and successfully integrates into the lignin producing a polymer that is readily cleaved under mild conditions, validating this concept. (Picture courtesy of Robin Davies, UW-Madison, Dept. Biochemistry.)

  2. Inside Cover

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    1. Inside Cover: Immobilised Lipase on Structured Supports Containing Covalently Attached Ionic Liquids for the Continuous Synthesis of Biodiesel in scCO2 (ChemSusChem 4/2012) (page 602)

      Prof. Pedro Lozano, Prof. Eduardo García-Verdugo, Juana M. Bernal, Diana F. Izquierdo, Prof.  M. Isabel Burguete, Prof. Gregorio Sánchez-Gómez and Prof. Santiago V. Luis

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cssc.201290014

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      The inside cover picture shows a continuous reactor, containing immobilized lipase onto a polymeric matrix with covalently attached ionic liquid phase (SILLPs), to synthesize biodiesel in supercritical CO2 from vegetable oil and methanol. In their paper on page 790, Lozano and co-workers describe the preparation and extraordinary performance of different nanostructured supports applied to immobilize Candida antarctica lipase B (CALB). The suitability of these immobilized lipase derivatives to carry out the synthesis of biodiesel by methanolysis of triolein in supercritical CO2 was excellent, leading up to 95% biodiesel yields with high operational stability.

  3. Graphical Abstract

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    1. Graphical Abstract: ChemSusChem 4/2012 (pages 603–611)

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cssc.201290015

  4. News

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    1. Spotlights on our sister journals: ChemSusChem 4/2012 (pages 614–616)

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cssc.201290016

  5. Communications

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    1. Electrochemical Synthesis of Adiponitrile from the Renewable Raw Material Glutamic Acid (pages 617–620)

      Jian-Jun Dai, Yao-Bing Huang, Chi Fang, Prof. Qing-Xiang Guo and Prof. Yao Fu

      Article first published online: 22 MAR 2012 | DOI: 10.1002/cssc.201100776

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      Current affairs: Adiponitrile, used to produce nylon 6.6, is prepared from the renewable compound glutamic acid by an electrochemical route, involving electro-oxidative decarboxylation and Kolbe coupling reactions. The new route is an example of the use of glutamic acid as a versatile substrate in the transformation of biomass into chemicals. Also, it highlights the use of electrochemical methods in biomass conversion.

    2. Highly Efficient Heterogeneous Gold-catalyzed Direct Synthesis of Tertiary and Secondary Amines from Alcohols and Urea (pages 621–624)

      Lin He, Yue Qian, Ran-Sheng Ding, Dr. Yong-Mei Liu, Prof. Dr. He-Yong He, Prof. Kang-Nian Fan and Prof. Dr. Yong Cao

      Article first published online: 13 MAR 2012 | DOI: 10.1002/cssc.201100581

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      Urea, the white gold: The efficient synthesis of tertiary and secondary amines is achieved by heterogeneous gold-catalyzed direct amination of stoichiometric alcohols with urea in good to excellent yields. Via a hydrogen autotransfer pathway, the reactions of primary alcohols with urea give tertiary amines exclusively, while secondary alcohols selectively afford secondary amines.

    3. Synthesis of Functional Acetylene Derivatives from Calcium Carbide (pages 625–628)

      Zhewang Lin, Dingyi Yu, Yin Ngai Sum and Dr. Yugen Zhang

      Article first published online: 29 FEB 2012 | DOI: 10.1002/cssc.201100649

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      AHA Erlebnis: CaC2, used to produce acetylene until several decades ago, is re-emerging as a cheap, sustainable resource synthesized from coal and lignocellulosic biomass. We report efficient catalytic protocols for the synthesis of functional acetylene derivatives from CaC2 through aldehyde, alkyne, and amine (AAA) as well as alkyne, haloalkane, and amine (AHA) couplings, and in addition demonstrate its use in click and Sonogashira chemistry, showing that calcium carbide is a sustainable and cost-efficient carbon source.

    4. Production of Biohydrogen by Aqueous Phase Reforming of Polyols over Platinum Catalysts Supported on Three-Dimensionally Bimodal Mesoporous Carbon (pages 629–633)

      Dr. Hyun Ju Park, Ho-Dong Kim, Dr. Tae-Wan Kim, Dr. Kwang-Eun Jeong, Dr. Ho-Jeong Chae, Dr. Soon-Yong Jeong, Dr. Young-Min Chung, Prof. Young-Kwon Park and Dr. Chul-Ung Kim

      Article first published online: 13 MAR 2012 | DOI: 10.1002/cssc.201100606

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      Now in 3D! Three-dimensionally bimodal carbons (3D-BMC) with mesopores of tunable size (controlled through the polymerization of the carbon precursor) are synthesized. After loading with platinum, the catalysts are used in aqueous phase reforming of polyols, and show superior performance in terms of carbon conversion, hydrogen yield, selectivity, and hydrogen production rate compared to platinum catalysts supported on activated carbon or two-dimensional CMK-3.

    5. Reduction of CO2 to CO at Low Overpotential in Neutral Aqueous Solution by a Ni(cyclam) Complex Attached to Poly(allylamine) (pages 634–636)

      Dr. Duraisamy Saravanakumar, Dr. Jieun Song, Nayoung Jung, Harishchandra Jirimali and Prof. Dr. Woonsup Shin

      Article first published online: 12 MAR 2012 | DOI: 10.1002/cssc.201100481

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      Less is more: Nickel cyclam complexes are known as efficient catalysts for the electrochemical reduction of CO2 to CO, despite having overvoltages of more than 0.6 V. Incorporating [Ni(cyclam)]2+ into poly(allylamine) through axial coordination of pyridine enables the electrochemical reduction of CO2 to CO near the thermodynamic potential of −0.78 V (vs. Ag/AgCl) at pH 8 with a current efficiency of 90 %.

    6. Mesoporous Nitrogen-Rich Carbon Materials as Catalysts for the Oxygen Reduction Reaction in Alkaline Solution (pages 637–641)

      Dr. Tharamani C. Nagaiah, Dr. Ankur Bordoloi, Dr. Miguel D. Sánchez , Prof. Dr. Martin Muhler and Prof. Dr. Wolfgang Schuhmann

      Article first published online: 16 MAR 2012 | DOI: 10.1002/cssc.201100284

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      ORR MNC, FTW! Mesoporous nitrogen-rich carbon (MNC) materials are synthesized by using polymer-loaded SBA-15 pyrolyzed at different temperatures. The activity and stability of the catalysts in the oxygen reduction reaction (ORR) are investigated by using cyclic voltammetry and rotating-disk electrode measurements. The MNC material pyrolyzed at 800 °C exhibits a high electrocatalytic activity towards the ORR in alkaline medium.

    7. A Green Chemistry of Graphene: Photochemical Reduction towards Monolayer Graphene Sheets and the Role of Water Adlayers (pages 642–646)

      Dr. Xin-Hao Li, Prof. Dr. Jie-Sheng Chen, Prof. Dr. Xinchen Wang, Dr. Manfred E. Schuster, Prof. Dr. Robert Schlögl and Prof. Dr. Markus Antonietti

      Article first published online: 13 MAR 2012 | DOI: 10.1002/cssc.201100467

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      Clean sheets: Stable aqueous dispersions of graphene sheets (GSs) are obtained by exposing graphene oxide to irradiation with light at room temperature, without using any chemical additives. The photochemical reduction method is sustainable and scalable, repairs a majority of defects in the graphene layers, and can be used to fine-tune surface functional groups. Interestingly, the aqueous GS dispersions are stable without any added surfactant. The existence of a water layer that is strongly bound to GS is evidenced.

    8. Metal-Free Nitrogen-Containing Carbon Nanotubes Prepared from Triazole and Tetrazole Derivatives Show High Electrocatalytic Activity towards the Oxygen Reduction Reaction in Alkaline Media (pages 647–651)

      Dr. Adina Morozan, Pascale Jégou, Dr. Mathieu Pinault, Dr. Stéphane Campidelli, Dr. Bruno Jousselme and Dr. Serge Palacin

      Article first published online: 2 MAR 2012 | DOI: 10.1002/cssc.201100675

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      High-performance oxygen reduction reaction (ORR) catalysts based on metal-free nitrogen-containing precursors and carbon nanotubes are reported. The investigated systems allow the evaluation of the effect of nitrogen-containing groups towards ORR and the results show that the catalysts are compatible with the conditions encountered in alkaline fuel cells, exhibiting good catalytic activity and stability compared with conventional Pt/C electrocatalyst.

    9. Synthesis of Cyclic Carbonates: Catalysis by an Iron-Based Composite and the Role of Hydrogen Bonding at the Solid/Liquid Interface (pages 652–655)

      Jin Qu, Dr. Chang-Yan Cao, Zhi-Feng Dou, Hua Liu, Yu Yu, Ping Li and Prof. Wei-Guo Song

      Article first published online: 22 MAR 2012 | DOI: 10.1002/cssc.201100839

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      Say it with flowers: Flower-like Fe3O4@Fe(OH)3 composite catalysts show good activity and stability in the synthesis of cyclic carbonates from epoxides and CO2. The role of hydrogen bonding between the surface hydroxyl groups of the solid and the epoxides at the solid/liquid interface is proposed as a key factor in activating the epoxide and stabilizing the ring-opened carbonate intermediates.

    10. An Intermolecular Heterobimetallic system for Photocatalytic Water Reduction (pages 656–660)

      Sven Hansen, Dr. Marcus Klahn, Dr. Torsten Beweries and Prof. Dr. Uwe Rosenthal

      Article first published online: 15 MAR 2012 | DOI: 10.1002/cssc.201100794

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      Teamwork: A new intermolecular heterobimetallic system for photocatalytic water reduction, consisting of a photosensitizer of the type [Ru(bpy)2(L)](PF6)2 (L=bidentate ligand), a dichloro palladium complex PdCl2(L) serving as the water reduction catalyst, and triethyl amine as electron donor, is presented. Variations of the ligand as well as of the palladium source results in a significant improvement of the performance of the catalyst system.

    11. Chemo-enzymatic Assembly of Clickable Cellulose Surfaces via Multivalent Polysaccharides (pages 661–665)

      Dr. Chunlin Xu, Dr. Oliver Spadiut, Dr. Ana Catarina Araújo, Dr. Azadeh Nakhai and Prof. Harry Brumer

      Article first published online: 15 MAR 2012 | DOI: 10.1002/cssc.201100522

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      The chemist′s guide to the galactosyl unit: A chemo-enzymatic process is developed for the multivalent functionalization of cellulose surfaces via regioselective oxidation of heteropolysaccharides with galactose 6-oxidase. Reductive amination, surface sorption, and click chemistry enable the assembly of (bio)chemically active cellulose surfaces for applications ranging from functional biocomposites to in vitro diagnostics.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
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    1. Depolymerization and Hydrodeoxygenation of Switchgrass Lignin with Formic Acid (pages 667–675)

      Weiyin Xu, Dr. Stephen J. Miller, Prof. Pradeep K. Agrawal and Prof. Christopher W. Jones

      Article first published online: 21 MAR 2012 | DOI: 10.1002/cssc.201100695

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      Cutting up grass: The effective liquid phase depolymerization and hydrodeoxygenation of switchgrass lignin in a batch reactor using formic acid as a combined hydrogen source and acid source, with and without Pt catalyst, is described. The depolymerization process is followed by using a range of techniques. The properties of products can be tailored by varying the reaction time.

    2. Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid (pages 676–686)

      Dr. Yuki Tobimatsu, Dr. Sasikumar Elumalai, Dr. John H. Grabber, Christy L. Davidson, Prof. Dr. Xuejun Pan and Prof. Dr. John Ralph

      Article first published online: 22 FEB 2012 | DOI: 10.1002/cssc.201100573

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      How sweet is this: Easier biomass processing can be achieved by introducing labile ester bonds into the lignin backbone through lignification with hydroxycinnamates such as rosmarinic acid, allowing the polymer to be readily depolymerized through anticipated biomass processing; biomass delignification and polysaccharide saccharification can therefore be achieved with lower energy inputs.

    3. Resin-Derived Hierarchical Porous Carbon Spheres with High Catalytic Performance in the Oxidative Dehydrogenation of Ethylbenzene (pages 687–693)

      Dr. Lifeng Wang , Dr. Juan J. Delgado , Dr. Benjamin Frank , Zhe Zhang, Zhichao Shan, Prof.Dr. Dang Sheng Su  and Prof. Dr. Feng-Shou Xiao

      Article first published online: 29 FEB 2012 | DOI: 10.1002/cssc.201100363

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      Bead it! A high-performance catalyst for the oxidative dehydrogenation of ethylbenzene to styrene is prepared from a commercial anion exchange resin via hard templating and carbonization to conserve the dedicated pore structure.

    4. Use of Industrial Waste for the Manufacturing of Sustainable Building Materials (pages 694–699)

      Rafael Sugrañez, Dr. Manuel Cruz-Yusta, Dr. Isabel Mármol, Dr. Francisco Martín, Dr. Julián Morales and Dr. Luis Sánchez

      Article first published online: 17 FEB 2012 | DOI: 10.1002/cssc.201100552

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      Concrete values: In this study, we develop a new and interesting way of valorizing granite waste (GW) by using it as a supplementary material in cement-based mortars, which are among the most widely used products in building and civil engineering works. The physico-chemical and mineralogical characteristics of GW, and the physical and mechanical properties of the new formulated mortars, are studied. The valorized waste and the new mortar exhibit ability in the photodegradation of organic dye.

    5. Synthesis of Nitrogen-Rich Mesoporous Carbon Nitride with Tunable Pores, Band Gaps and Nitrogen Content from a Single Aminoguanidine Precursor (pages 700–708)

      Siddulu N. Talapaneni, Gurudas P. Mane, Ajayan Mano, Dr. Chokkalingam Anand, Dr. Dattatray S. Dhawale, Prof. Toshiyuki Mori and Prof. Ajayan Vinu

      Article first published online: 2 MAR 2012 | DOI: 10.1002/cssc.201100626

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      Tune in, see the pores: We report on the synthesis of N-rich mesoporous carbon nitrides (CNs) with tunable pore diameters, N content, and band gaps through hard templating using a single aminoguanidine molecule as a CN precursor, which shows a much higher activity for Friedel–Crafts acylation of benzene with hexanoyl chloride as compared to other CNs with and without a mesoporous structure. We expect that these materials may be used in photoelectrochemical applications.

    6. Controlling Size, Amount, and Crystalline Structure of Nanoparticles Deposited on Graphenes for Highly Efficient Energy Conversion and Storage (pages 709–715)

      Bong Gill Choi and Prof. Dr. Ho Seok Park

      Article first published online: 22 MAR 2012 | DOI: 10.1002/cssc.201100565

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      Have a GO at nanoparticles: Various nanoparticles, including Pt, Au, Pd, Ru, and crystalline RuO2, are synthesized in situ and directly deposited on graphene sheets functionalized with ionic liquids. The size, amount, and crystalline structure of the nanoparticles can be controlled to prepare high performance electrocatalysts (for example, for methanol oxidation) and pseudocapacitive materials for energy conversion and storage, respectively.

    7. Ionically Tagged Iron Complex-Catalyzed Epoxidation of Olefins in Imidazolium-Based Ionic Liquids (pages 716–726)

      Marcelo R. dos Santos, Julia R. Diniz, Aline M. Arouca, Alexandre F. Gomes, Prof. Dr. Fabio C. Gozzo, Prof. Dr. Silvia M. Tamborim, Prof. Dr. Alexandre L. Parize, Prof. Dr. Paulo A. Z. Suarez and Prof. Dr. Brenno A. D. Neto

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cssc.201100453

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      Steely tags: The synthesis, characterization and efficient application of a new ionically tagged iron catalyst in the oxidation (epoxidation) of C[DOUBLE BOND]C double bonds using air (or H2O2) as the oxidizing agent is described. A mechanism for the oxidation reaction is proposed. Recycling the catalyst at least ten times can be achieved with no loss of activity.

    8. Carbon-Supported Molybdenum Carbide Catalysts for the Conversion of Vegetable Oils (pages 727–733)

      Dr. Junxing Han, Dr. Jinzhao Duan, Dr. Ping Chen, Prof. Hui Lou, Prof. Xiaoming Zheng and Dr. Haiping Hong

      Article first published online: 28 FEB 2012 | DOI: 10.1002/cssc.201100476

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      Regulated support: Ordered mesoporous carbon-supported molybdenum carbide catalysts are prepared in one pot. By changing the amount of Mo precursor from less than 2 % to over 5 %, molybdenum carbide structures are easily regulated from Mo2C to MoC. Compared with Mo2C, MoC exhibits a high product selectivity and excellent resistance to leaching when converting vegetable oils into diesel-like hydrocarbons (see picture).

    9. Benign Catalysis with Iron: Unique Selectivity in Catalytic Isomerization Reactions of Olefins (pages 734–739)

      Dr. Reiko Jennerjahn, Dr. Ralf Jackstell, Dr. Irene Piras, Prof. Dr. Robert Franke, Dr. Haijun Jiao, Dr. Matthias Bauer and Prof. Matthias Beller

      Article first published online: 12 MAR 2012 | DOI: 10.1002/cssc.201100404

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      Stop—Further reaction not allowed! We present a general and selective hydrido triiron carbonyl cluster-catalyzed mono-isomerization of olefins, which allows for the selective generation of 2-olefins, whereby classic acidic catalysts give mixtures of various internal olefins. The proposed reaction mechanism is supported by in situ NMR studies, DFT calculations, and EXAFS measurements.

    10. Adsorption and Separation of Light Gases on an Amino-Functionalized Metal–Organic Framework: An Adsorption and In Situ XRD Study (pages 740–750)

      Sarah Couck, Dr. Elena Gobechiya, Prof. Christine E. A. Kirschhock, Pablo Serra-Crespo, Jana Juan-Alcañiz, Alberto Martinez Joaristi, Dr. Eli Stavitski, Dr. Jorge Gascon, Prof. Dr. Freek Kapteijn, Prof. Dr. Gino V. Baron and Prof. Dr. Joeri F. M. Denayer

      Article first published online: 29 FEB 2012 | DOI: 10.1002/cssc.201100378

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      Breathing CO2: Efficient adsorption of CO2 in the initially very narrow pores of a metal–organic framework while other light gases are nearly excluded is reported. This leads to large CO2 separation potentials, which is demonstrated by breakthrough experiments. The breathing properties of the material are demonstrated by means of in situ XRD patterns measured during the adsorption of CO2 and CH4.

    11. A One-Pot Method for the Selective Conversion of Hemicellulose from Crop Waste into C5 Sugars and Furfural by Using Solid Acid Catalysts (pages 751–761)

      Ramakanta Sahu and Dr. Paresh Laxmikant Dhepe

      Article first published online: 12 MAR 2012 | DOI: 10.1002/cssc.201100448

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      Chewing the cud! Selective conversion of hemicellulose from crop waste (containing cellulose, hemicellulose, and lignin) into xylose + arabinose or furfural can be achieved over solid acid catalysts in aqueous or biphasic media, respectively (see picture). Yields are high and good mass balances (taking into account arabinose, xylose, and oligomers) have been determined. A detailed catalyst characterization study is presented.

    12. A Method for Screening the Potential of MOFs as CO2 Adsorbents in Pressure Swing Adsorption Processes (pages 762–776)

      Dr. Gerhard D. Pirngruber, Dr. Lomig Hamon, Dr. Sandrine Bourrelly, Dr. Philip L. Llewellyn, Dr. Estelle Lenoir, Dr. Vincent Guillerm, Dr. Christian Serre and Dr. Thomas Devic

      Article first published online: 21 MAR 2012 | DOI: 10.1002/cssc.201100716

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      Looking for the needle: Based on a huge body of single-component and mixture adsorption data, we present a methodology for screening the performance of MOFs in pressure swing adsorption (PSA). The investigated MOFs are well placed in a preliminary ranking of performance in a PSA process for the separation of CO2 from synthesis gas and biogas, in comparison with the reference adsorbents activated carbons and zeolites.

    13. Development of New Hydrogenations of Imines and Benign Reductive Hydroaminations: Zinc Triflate as a Catalyst (pages 777–782)

      Svenja Werkmeister, Steffen Fleischer, Dr. Shaolin Zhou, Dr. Kathrin Junge and Prof. Matthias Beller

      Article first published online: 9 FEB 2012 | DOI: 10.1002/cssc.201100633

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      It's a triflate with zinc: The hydrogenation of imines and the reductive hydro- amination of alkynes with hydrogen and amines have been achieved by applying zinc triflate as a catalyst. This methodology is a convenient alternative to the use of precious metal-based catalysts and expensive silanes and Hantzsch ester dihydropyridines.

    14. The First Molecular Level Monitoring of Carbohydrate Conversion to 5-Hydroxymethylfurfural in Ionic Liquids. B2O3—An Efficient Dual-Function Metal-Free Promoter for Environmentally Benign Applications (pages 783–789)

      Elena A. Khokhlova, Dr. Vadim V. Kachala and Prof. Dr. Valentine P. Ananikov

      Article first published online: 22 FEB 2012 | DOI: 10.1002/cssc.201100670

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      Attend to formation and separation: A new NMR procedure has been developed to investigate molecular structures and chemical reactions directly in ionic liquids. The mechanism of the conversion of carbohydrates to 5-hydroxymethylfurfural (5-HMF) is studied at the molecular level with the detection of anomers and intermediate species. The study highlights the need for more attention to be paid to the 5-HMF separation and humin formation steps.

    15. Immobilised Lipase on Structured Supports Containing Covalently Attached Ionic Liquids for the Continuous Synthesis of Biodiesel in scCO2 (pages 790–798)

      Prof. Pedro Lozano, Prof. Eduardo García-Verdugo, Juana M. Bernal, Diana F. Izquierdo, Prof.  M. Isabel Burguete, Prof. Gregorio Sánchez-Gómez and Prof. Santiago V. Luis

      Article first published online: 1 MAR 2012 | DOI: 10.1002/cssc.201100692

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      Enzyme catalysis goes critical:Candida antarctica lipase B has been immobilised on different polymeric matrices containing a covalently attached ionic liquid phase. A continuous biocatalytic process for biodiesel synthesis has been successfully carried out in supercritical CO2 for 45 operational cycles with excellent enzyme activity and stability. Appropriate selection of the IL results in a clear improvement of the efficiency for the biotransformation.

  7. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Graphical Abstract
    5. News
    6. Communications
    7. Full Papers
    8. Preview
    1. You have free access to this content
      Preview: ChemSusChem 5/2012 (page 799)

      Article first published online: 30 MAR 2012 | DOI: 10.1002/cssc.201290017

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