ChemSusChem

Cover image for Vol. 6 Issue 9

Special Issue: CatchBio

September 2013

Volume 6, Issue 9

Pages 1557–1778

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Reviews
    7. Minireview
    8. Essay
    9. Communications
    10. Full Papers
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      Cover Picture: Recalcitrance of Nature: Chemocatalysis for the Production of Biomass-Based Building Blocks (ChemSusChem 9/2013) (page 1557)

      Prof. Dr. Bert M. Weckhuysen 

      Article first published online: 3 SEP 2013 | DOI: 10.1002/cssc.201300884

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      The cover image of this Special Issue of ChemSusChem shows the philosophy behind ”CatchBio“, a public–private research consortium in the Netherlands dedicated to state-of-the-art chemistry within the field of chemocatalytic biomass conversion. Its three-stage approach involves obtaining fundamental insight in the chemistry needed to handle biomass in chemical reactors, thereby generating leads. The most promising leads are then selected by industry based on technological and socio-economic criteria. More about this methodology and the papers in this special issue can be found in the Editorial by guest editor Bert Weckhuysen on page 1559.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Reviews
    7. Minireview
    8. Essay
    9. Communications
    10. Full Papers
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      Recalcitrance of Nature: Chemocatalysis for the Production of Biomass-Based Building Blocks (pages 1559–1563)

      Prof. Dr. Bert M. Weckhuysen 

      Article first published online: 14 SEP 2013 | DOI: 10.1002/cssc.201300602

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      Catch me if you can: Since its early days catalysis science and technology has shaped our society and provided us with the means and goods to enjoy a more prosperous life. Chemocatalytic conversion is a key enabler for the efficient utilization of biomass, an important factor in this new era of sustainability. This Special Issue of ChemSusChem is dedicated to state-of-the-art chemistry within the field, specifically focusing on the joint research efforts in The Netherlands within the public–private research consortium CatchBio.

  3. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Reviews
    7. Minireview
    8. Essay
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      Graphical Abstract: ChemSusChem 9/2013 (pages 1564–1570)

      Article first published online: 14 SEP 2013 | DOI: 10.1002/cssc.201390033

  4. News

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Reviews
    7. Minireview
    8. Essay
    9. Communications
    10. Full Papers
  5. Reviews

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Reviews
    7. Minireview
    8. Essay
    9. Communications
    10. Full Papers
    1. Reaction Pathways for the Deoxygenation of Vegetable Oils and Related Model Compounds (pages 1576–1594)

      Robert W. Gosselink, Stefan A. W. Hollak, Shu-Wei Chang, Dr. Jacco van Haveren, Prof. Dr. Krijn P. de Jong, Dr. Johannes H. Bitter and Dr. Daan S. van Es

      Article first published online: 1 AUG 2013 | DOI: 10.1002/cssc.201300370

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      Deoxygenation—yes or no? The deoxygenation of vegetable oil-based feeds is mostly studied using model compounds. Reactions in the presence and absence of H2 show possible deoxygenation pathways and intermediates for the different model compounds. By studying the influence of the type of catalyst, reaction atmosphere, feedstock, and its degree of unsaturation on the deoxygenation pathways we conclude on the suitability of model compounds for the deoxygenation of vegetable oil-based feeds.

    2. Chemocatalytic Conversion of Ethanol into Butadiene and Other Bulk Chemicals (pages 1595–1614)

      Carlo Angelici, Prof. Bert M. Weckhuysen and Dr. Pieter C. A. Bruijnincx

      Article first published online: 23 MAY 2013 | DOI: 10.1002/cssc.201300214

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      Fuel for thought: The dedicated production of 1,3-butadiene from bioethanol is expected to be an effective solution to its current substantial price increase. The Lebedev process for ethanol-to-butadiene conversion is reviewed in detail. The Review also extends to other commodity chemicals that are produced from ethanol and are involved as intermediates or byproducts in the bio-based butadiene production process.

  6. Minireview

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    7. Minireview
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    1. Organophosphorus Catalysis to Bypass Phosphine Oxide Waste (pages 1615–1624)

      Dr. Henri A. van Kalkeren, Dr. Floris L. van Delft and Prof. Dr. Floris P. J. T. Rutjes

      Article first published online: 3 SEP 2013 | DOI: 10.1002/cssc.201300368

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      Waste not wanted: In the past decade, several methods have emerged that address the formation of phosphine oxide waste products resulting from well-known organic transformations such as Wittig, Appel, and Mitsunobu reactions. This Minireview outlines the two distinct strategies and the underpinning research. The potential of the emerging field of organophosphorus catalysis is highlighted and new developments that may stimulate further research are described.

  7. Essay

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    7. Minireview
    8. Essay
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    10. Full Papers
    1. Economic Feasibility of the Sugar Beet-to-Ethylene Value Chain (pages 1625–1630)

      Jeroen Althoff, Kees Biesheuvel, Ad De Kok, Dr. Henk Pelt, Dr. Matthijs Ruitenbeek, Ger Spork, Jan Tange and Ronald Wevers

      Article first published online: 28 AUG 2013 | DOI: 10.1002/cssc.201300478

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      The cost of sugar: The economic value of sugar produced from regional crops is evaluated in depth by modeling various business models. The analysis of the sugar-to-ethylene value chain demonstrates that the value of sugar is too high in the current global market environment to consider it as a starting material for ethylene.

  8. Communications

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    3. Editorial
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    5. News
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    7. Minireview
    8. Essay
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    10. Full Papers
    1. Synthesis of Renewable Fine-Chemical Building Blocks by Reductive Coupling between Furfural Derivatives and Terpenes (pages 1631–1635)

      Céline M. Nicklaus, Prof. Adriaan J. Minnaard, Prof. Ben L. Feringa and Prof. Johannes G. de Vries

      Article first published online: 15 JUL 2013 | DOI: 10.1002/cssc.201300179

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      Sugar and Spice…: The use of renewable resources to produce fine chemicals is an underdeveloped area. A waste-free technology will be necessary to further convert platform chemicals, readily available from biomass. We show that furfurals, which can be obtained from C5 sugars, can be coupled with terpenes in up to 95 % yield through ruthenium-catalyzed reductive couplings developed by Krische et al.

    2. Efficient Formation of Benzylic Quaternary Centers via Palladium Catalysis (pages 1636–1639)

      Dr. Aditya L. Gottumukkala, Jasmin Suljagic, Dr. Kiran Matcha, Prof. Dr. Johannes G. de Vries and Prof. Dr. Adriaan J. Minnaard

      Article first published online: 2 JUL 2013 | DOI: 10.1002/cssc.201300276

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      Four′s a crowd: An efficient protocol for the formation of benzylic quaternary centers via arylation of enones using a catalyst made from Pd(O2CCF3)2 and 2,2′-bipyridine is developed. For cyclic substrates, catalyst loadings as low as 1 mol % Pd are enough to afford excellent yields (>90 %) using a variety of arylboronic acids. In case of acyclic substrates, the addition of KSbF6 was found to improve conversions and yields.

    3. Waste Not, Want Not: Mild and Selective Catalytic Oxidation of Uronic Acids (pages 1640–1645)

      Frits van der Klis, Dr. Augustinus E. Frissen, Dr. Jacco van Haveren and Dr. Daan S. van Es

      Article first published online: 12 AUG 2013 | DOI: 10.1002/cssc.201300367

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      And isn′t it uronic: A mild, highly efficient and selective catalytic oxidation of pectin-derived uronic acids to the corresponding aldaric acids is reported. Fast, quantitative conversions (>99 %) of the starting materials are achieved with high selectivity (>97 %) at room temperature, using supported gold catalysts and air as oxidizing agent.

    4. Towards Liquid Fuels from Biosyngas: Effect of Zeolite Structure in Hierarchical-Zeolite-Supported Cobalt Catalysts (pages 1646–1650)

      Sina Sartipi, Margje Alberts, Mark J. Meijerink, Tobias C. Keller, Prof. Javier Pérez-Ramírez, Dr. Jorge Gascon and Prof. Freek Kapteijn

      Article first published online: 13 JUN 2013 | DOI: 10.1002/cssc.201300339

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      Wax on, wax off: Bifunctional cobalt-based catalysts on zeolite supports are applied for the valorization of biosyngas through Fischer-Tropsch chemistry. By using these catalysts, waxes can be hydrocracked to shorter-chain hydrocarbons, increasing the selectivity towards the C5–C11 (gasoline) fraction. The zeolite topology and the amount and strength of acid sites are key parameters to maximize the performance of these bifunctional catalysts, steering Fischer-Tropsch product selectivity towards liquid hydrocarbons.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Graphical Abstract
    5. News
    6. Reviews
    7. Minireview
    8. Essay
    9. Communications
    10. Full Papers
    1. Valorization of Humin-Based Byproducts from Biomass Processing—A Route to Sustainable Hydrogen (pages 1651–1658)

      Thi Minh Chau Hoang, Prof Dr. Leon Lefferts and Prof. Dr. K. Seshan

      Article first published online: 12 AUG 2013 | DOI: 10.1002/cssc.201300446

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      Humin to hydrogen: Humin is the major waste byproducts of sugar conversion (dehydration of glucose) and has a high carbon content. Using this waste byproduct, sustainable hydrogen or syngas can be obtained through catalytic steam reforming. The influence of the gasification conditions is investigated, for example, temperature and alkali-based catalyst, with the aim for valorization of humin through catalytic gasification.

    2. Electrocatalytic Hydrogenation of 5-Hydroxymethylfurfural in the Absence and Presence of Glucose (pages 1659–1667)

      Youngkook Kwon, Dr. Ed de Jong, Saeed Raoufmoghaddam and Prof. Marc T. M. Koper

      Article first published online: 15 JUL 2013 | DOI: 10.1002/cssc.201300443

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      A clean sweep: The hydrogenation of HMF in neutral media has been studied on a wide range of solid metal electrodes both in the absence and in the presence of glucose. From HMF hydrogenation, three groups of catalysts show affinities towards (1) DHMF, (2) DHMF and other products, depending on applied potentials, and (3) other products. HMF hydrogenation is shown to be preferred to glucose hydrogenation on all metals.

    3. Functionalized Carbon Nanofibers as Solid-Acid Catalysts for Transesterification (pages 1668–1672)

      Dr. Daniel R. Stellwagen, Frits van der Klis, Dr. Daan S. van Es, Prof. Dr. Krijn P. de Jong and Dr. Johannes H. Bitter

      Article first published online: 31 JUL 2013 | DOI: 10.1002/cssc.201300372

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      Acids and carbons: Carbon nanofibers were functionalized with aryl sulfonic acid groups by in situ diazonium coupling. The material is an efficient catalyst for the transesterification of triolein and methanol, outperforming conventional sulfonated carbons. Correlation of catalytic performance and number of active sites indicates that the acidic groups introduced by the diazonium coupling method show increased activity and accessibility to the triglyceride substrate.

    4. Catalytic Deoxydehydration of Diols to Olefins by using a Bulky Cyclopentadiene-based Trioxorhenium Catalyst (pages 1673–1680)

      Suresh Raju, Dr. Johann T. B. H. Jastrzebski, Dr. Martin Lutz and Prof. Dr. Robertus J. M. Klein Gebbink

      Article first published online: 10 JUL 2013 | DOI: 10.1002/cssc.201300364

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      In the bulk of it: Bulky 1,2,4-tri(tert-butyl)cyclopentadienyl trioxorhenium was studied as a catalyst for the deoxydehydration of different vicinal diols. Under optimised conditions, a variety of vicinal diols were converted into olefins in good to excellent yields, and with minimal olefin isomerisation. Biomass-derived polyols were also converted into their corresponding olefinic products.

    5. Dehydration of Different Ketoses and Aldoses to 5-Hydroxymethylfurfural (pages 1681–1687)

      Robert-Jan van Putten, Jenny N. M. Soetedjo, Dr. Evgeny A. Pidko, Dr. Jan C. van der Waal, Prof. Dr. Emiel J. M. Hensen, Dr. Ed de Jong and Prof. Dr. Hero J. Heeres

      Article first published online: 23 AUG 2013 | DOI: 10.1002/cssc.201300345

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      Ketose dries out: Hexose dehydration to 5-hydroxymethylfurfural is studied using different ketoses and aldoses. The reactivity of the different ketoses is found to be a function of the hydroxyl group orientation at the C3 and C4 positions. The results point to a dehydration mechanism involving cyclic intermediates. For aldoses, no influence of the hydroxyl group orientation is observed, indicating a different rate-determining step.

    6. The Mechanism of Glucose Isomerization to Fructose over Sn-BEA Zeolite: A Periodic Density Functional Theory Study (pages 1688–1696)

      Dr. Gang Yang, Dr. Evgeny A. Pidko and Prof. Dr. Emiel J. M. Hensen

      Article first published online: 13 AUG 2013 | DOI: 10.1002/cssc.201300342

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      Hitting the sweet spot: Catalytic isomerization of glucose to fructose necessitates the presence of large lattice defects containing a Lewis acidic SnOH center and an adjacent extended silanol nest, as shown by a periodic density functional theory study. The multiple-point interaction between the sugar molecule and such a reactive center inside micropores of the zeolite Sn-BEA directs the chemical transformations.

    7. Glucose Dehydration to 5-Hydroxymethylfurfural in a Biphasic System over Solid Acid Foams (pages 1697–1707)

      Dr. Vitaly V. Ordomsky, Dr. John van der Schaaf, Prof. Dr. Jaap C. Schouten and Dr. T. Alexander Nijhuis

      Article first published online: 24 APR 2013 | DOI: 10.1002/cssc.201300017

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      Cat-Al-ytically coated: The preparation of a solid acid foam based on zirconium phosphate (ZrPO) coating on aluminum foam is described. The catalytic properties are evaluated in the dehydration of glucose to 5-hydroxymethylfurfural in a biphasic rotating foam reactor (see picture). The silylation procedure leads to a higher selectivity, and a more intensive contact of the foam with aqueous and organic phases leads to an increase of selectivity and stability.

    8. Hydrogen Production through Aqueous-Phase Reforming of Ethylene Glycol in a Washcoated Microchannel (pages 1708–1716)

      M. Fernanda Neira D'Angelo, Dr. Vitaly Ordomsky, Violeta Paunovic, Dr. John van der Schaaf, Prof. Dr. Jaap C. Schouten and Dr. T. Alexander Nijhuis

      Article first published online: 16 APR 2013 | DOI: 10.1002/cssc.201200974

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      Left out to dry: Aqueous-phase reforming (APR) of biocarbohydrates is conducted for the first time in a catalytically stable washcoated microchannel in which multiphase hydrogen removal enhances the hydrogen efficiency. The microchannel presents higher conversion of ethylene glycol and higher selectivity to hydrogen than a fixed-bed reactor. The use of microreactor technology for APR allows for a great reduction in the reformer size, which is promising for distributed hydrogen production.

    9. Towards Stable Catalysts for Aqueous Phase Conversion of Ethylene Glycol for Renewable Hydrogen (pages 1717–1723)

      Kamila Koichumanova, Anna Kaisa K. Vikla, Dr. Dennis J. M. de Vlieger, Prof. Dr. K. Seshan, Dr. Barbara L. Mojet and Prof. Dr. Leon Lefferts

      Article first published online: 10 SEP 2013 | DOI: 10.1002/cssc.201300445

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      Transformation for high activity: Aqueous-phase reforming (APR) of ethylene glycol over alumina-supported Pt catalysts is reported. On heating and at high pressures, the alumina support transforms to AlO(OH) (boehmite). This phase transformation is studied in situ by using attenuated total reflectance IR spectroscopy. Pt/AlO(OH) shows excellent stability at APR conditions and allows efficient production of hydrogen. It is assumed that the high concentration of OH species on boehmite make it a promising support for catalysts.

    10. Early-Stage Comparative Sustainability Assessment of New Bio-based Processes (pages 1724–1736)

      Akshay D. Patel, Koen Meesters, Herman den Uil, Dr. Ed de Jong, Prof. Ernst Worrell and Dr. Martin K. Patel

      Article first published online: 14 SEP 2013 | DOI: 10.1002/cssc.201300168

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      Sustainability goes Dutch! An early-stage sustainability assessment framework is used to evaluate eight new bio-based process alternatives under development within the CatchBio research consortium in the Netherlands. Criteria include economics, environmental impact, hazards, and techno-economic and life cycle assessments. The results of this multi-criteria assessment framework can act as a support for R&D decision making.

    11. Ligand Effects on the Hydrogenation of Biomass-Inspired Substrates with Bifunctional Ru, Ir, and Rh Complexes (pages 1737–1744)

      Eveline Jansen, Linda S. Jongbloed, Dr. Dorette S. Tromp, Dr. Martin Lutz, Prof. Dr. Bas de Bruin and Prof. Dr. Cornelis J. Elsevier

      Article first published online: 14 SEP 2013 | DOI: 10.1002/cssc.201300363

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      Adding value to biomass: The influence of structural variations of N-heterocyclic carbene–amine motif in half-sandwich Ru, Ir, and Rh complexes on the hydrogenation of biomass-inspired substrates is reported. Through this study insight is gained for the future rational design of hydrogenation catalysts for the conversion of biomass into useful/added-value compounds.

    12. Formation, Molecular Structure, and Morphology of Humins in Biomass Conversion: Influence of Feedstock and Processing Conditions (pages 1745–1758)

      Ilona van Zandvoort, Yuehu Wang, Carolus B. Rasrendra, Dr. Ernst R. H. van Eck, Dr. Pieter C. A. Bruijnincx, Prof. Dr. Hero J. Heeres and Prof. Dr. Bert M. Weckhuysen

      Article first published online: 8 JUL 2013 | DOI: 10.1002/cssc.201300332

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      Under scrutiny: Humin byproducts formed during the acid-catalyzed dehydration of sugars are analyzed with multiple techniques to reveal a furan-rich network formed via hydroxymethylfurfural (see picture). Within this network, the aliphatic linkages and oxygen functionalities strongly depend on the feedstock. A representative model for the molecular structure of humins is proposed.

    13. Chemo- and Regioselective Homogeneous Rhodium-Catalyzed Hydroamidomethylation of Terminal Alkenes to N-Alkylamides (pages 1759–1773)

      Saeed Raoufmoghaddam, Prof. Dr. Eite Drent and Prof. Dr. Elisabeth Bouwman

      Article first published online: 5 SEP 2013 | DOI: 10.1002/cssc.201300484

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      Taking control: A rhodium/xantphos homogeneous catalyst system has been developed for direct chemo- and regioselective mono-N-alkylation of primary amides with 1-alkenes and syngas through the new catalytic hydroamidomethylation reaction (see picture).

    14. Manganese-Catalyzed Selective Oxidation of Aliphatic C[BOND]H groups and Secondary Alcohols to Ketones with Hydrogen Peroxide (pages 1774–1778)

      Jia Jia Dong, Duenpen Unjaroen, Francesco Mecozzi, Dr. Emma C. Harvey, Dr. Pattama Saisaha, Dr. Dirk Pijper, Dr. Johannes W. de Boer, Dr. Paul Alsters, Prof. Dr. Ben L. Feringa and Prof. Dr. Wesley R. Browne

      Article first published online: 5 SEP 2013 | DOI: 10.1002/cssc.201300378

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      Manganeasy! MnII, picolinic acid, and butanedione make a smart mix for oxidation of secondary alcohols and alkanes and especially benzylic groups to ketones at room temperature with near stoichiometric amounts of hydrogen peroxide, low catalyst loadings, and high turn-over numbers.

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