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Coby Clarke, Wei-Chien Tu, Oliver Levers, Andreas Bröhl, J. Hallett (2018)
Green and Sustainable Solvents in Chemical Processes.Chemical reviews, 118 2
Liam Mistry, Kopano Mapesa, Thomas Bousfield, Jason Camp (2017)
Synthesis of ureas in the bio-alternative solvent CyreneGreen Chemistry, 19
J. Camp, Jay Dunsford, Edward Cannons, William Restorick, A. Gadzhieva, M. Fay, R. Smith (2014)
Glucose-Derived Palladium(0) Nanoparticles as in Situ-Formed Catalysts for Suzuki–Miyaura Cross-Coupling Reactions in IsopropanolACS Sustainable Chemistry & Engineering, 2
M. Abraham (1969)
Solvent effects on the free energies of the reactants and transition states in the Menschutkin reaction of trimethylamine with alkyl halidesJournal of The Chemical Society D: Chemical Communications
Lipeng Wu, Takahiko Moteki, A. Gokhale, D. Flaherty, F. Toste (2016)
Production of Fuels and Chemicals from Biomass: Condensation Reactions and BeyondChem, 1
C. Alder, J. Hayler, R. Henderson, A. Redman, Lena Shukla, Leanna Shuster, H. Sneddon (2016)
Updating and further expanding GSK's solvent sustainability guideGreen Chemistry, 18
Long Zhou, Yann Lie, H. Briers, Jiajun Fan, J. Remón, Josefina Nyström, V. Budarin, D. Macquarrie, C. McElroy (2018)
Natural Product Recovery from Bilberry (Vaccinium myrtillus L.) Presscake via Microwave HydrolysisACS Sustainable Chemistry & Engineering
G. Huber, S. Iborra, A. Corma (2006)
Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering.Chemical reviews, 106 9
Siddarth Krishna, D. McClelland, Quinn Rashke, J. Dumesic, G. Huber (2017)
Hydrogenation of levoglucosenone to renewable chemicalsGreen Chemistry, 19
B. Lipshutz, F. Gallou, Sachin Handa (2016)
Evolution of Solvents in Organic ChemistryACS Sustainable Chemistry & Engineering, 4
H. Kawamoto, S. Saito, Wataru Hatanaka, S. Saka (2007)
Catalytic pyrolysis of cellulose in sulfolane with some acidic catalystsJournal of Wood Science, 53
Madhu Kaushik, A. Li, R. Hudson, M. Masnadi, Chao‐Jun Li, Audrey Moores (2016)
Reversing aggregation: direct synthesis of nanocatalysts from bulk metal. Cellulose nanocrystals as active support to access efficient hydrogenation silver nanocatalystsGreen Chemistry, 18
Z. Witczak, R. Bielski, D. Mencer (2017)
Concise and Efficient Synthesis of E-stereoisomers of exo-cyclic Carbohydrate Enones. Aldol Condensation of Dihydrolevoglucosenone with Five-membered Aromatic Aldehydes1 Part 1.Tetrahedron Letters, 58
Jason Camp, Jay Dunsford, Oliver Dacosta, R. Blundell, James Adams, Joshua Britton, Robert Smith, Thomas Bousfield, Michael Fay (2016)
Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous mediaRSC Advances, 6
Fiona McGonagle, H. Sneddon, C. Jamieson, A. Watson (2014)
Molar efficiency : a useful metric to gauge relative reaction efficiency in discovery medicinal chemistryACS Sustainable Chemistry & Engineering, 2
Shinji Kudo, Nozomi Goto, J. Sperry, K. Norinaga, J. Hayashi (2017)
Production of Levoglucosenone and Dihydrolevoglucosenone by Catalytic Reforming of Volatiles from Cellulose Pyrolysis Using Supported Ionic Liquid PhaseACS Sustainable Chemistry & Engineering, 5
X. Sui, Z. Wang, Bing Liao, Ying Zhang, Q. Guo (2012)
Preparation of levoglucosenone through sulfuric acid promoted pyrolysis of bagasse at low temperature.Bioresource technology, 103 1
G. Dobele, G. Rossinskaja, G. Telysheva, D. Meier, O. Faix (1999)
Cellulose dehydration and depolymerization reactions during pyrolysis in the presence of phosphoric acidJournal of Analytical and Applied Pyrolysis, 49
Kirsty Wilson, J. Murray, C. Jamieson, A. Watson (2018)
Cyrene as a bio-based solvent for HATU mediated amide coupling.Organic & biomolecular chemistry, 16 16
Paul Murray, F. Bellany, L. Benhamou, Dejan-Krešimir Bučar, A. Tabor, T. Sheppard (2016)
The application of design of experiments (DoE) reaction optimisation and solvent selection in the development of new synthetic chemistry.Organic & biomolecular chemistry, 14 8
A. Alhifthi, B. Harris, L. Goerigk, J. White, Spencer Williams (2017)
Structure-reactivity correlations of the abnormal Beckmann reaction of dihydrolevoglucosenone oxime.Organic & biomolecular chemistry, 15 47
A. Tagirov, I. Biktagirov, Y. Galimova, L. Faizullina, S. Salikhov, F. Valeev (2015)
Opening of the 1,6-anhydro bridge with selective reduction of the acetal moiety in levoglucosenone and its derivativesRussian Journal of Organic Chemistry, 51
Jinfeng Zhang, G. White, Michaela Ryan, A. Hunt, Michael Katz (2016)
Dihydrolevoglucosenone (Cyrene) As a Green Alternative to N,N-Dimethylformamide (DMF) in MOF SynthesisACS Sustainable Chemistry & Engineering, 4
C. Cirtiu, Alexandre Dunlop-Brière, Audrey Moores (2011)
Cellulose nanocrystallites as an efficient support for nanoparticles of palladium: application for catalytic hydrogenation and Heck coupling under mild conditionsGreen Chemistry, 13
Ana Pacheco, James Sherwood, Anna Zhenova, C. McElroy, A. Hunt, H. Parker, T. Farmer, A. Constantinou, M. bruyn, A. Whitwood, W. Raverty, J. Clark (2016)
Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives.ChemSusChem, 9 24
Shinji Kudo, Zhenwei Zhou, K. Norinaga, J. Hayashi (2011)
Efficient levoglucosenone production by catalytic pyrolysis of cellulose mixed with ionic liquidGreen Chemistry, 13
Siddarth Krishna, Kefeng Huang, K. Barnett, Jiayue He, C. Maravelias, J. Dumesic, G. Huber, M. Bruyn, B. Weckhuysen (2018)
Oxygenated commodity chemicals from chemo‐catalytic conversion of biomass derived heterocyclesAiche Journal, 64
Danilo Malferrari, N. Armenise, S. Decesari, P. Galletti, E. Tagliavini (2015)
Surfactants from Itaconic Acid: Physicochemical Properties and Assessment of the Synthetic StrategiesACS Sustainable Chemistry & Engineering, 3
Guillaume Bonneau, A. Peru, A. Flourat, F. Allais (2018)
Organic solvent- and catalyst-free Baeyer–Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene®): a sustainable route to (S)-γ-hydroxymethyl-α,β-butenolide and (S)-γ-hydroxymethyl-γ-butyrolactoneGreen Chemistry, 20
M. Miura, H. Kaga, Takashi Yoshida, K. Ando (2001)
Microwave pyrolysis of cellulosic materials for the production of anhydrosugarsJournal of Wood Science, 47
E. Ledingham, Kieran Stockton, B. Greatrex (2017)
Efficient Synthesis of an Indinavir Precursor from Biomass-Derived (–)-LevoglucosenoneAustralian Journal of Chemistry, 70
F. Shafizadeh, R. Furneaux, T. Stevenson (1979)
Some reactions of levoglucosenoneCarbohydrate Research, 71
F. Eiden, Felix Denk, G. Höfner (1994)
ZNS‐wirksame Pyrane: Amin‐ und arylsubstituierte DioxabicyclooctaneArchiv der Pharmazie, 327
N. Brun, P. Hesemann, D. Esposito (2017)
Expanding the biomass derived chemical spaceChemical Science, 8
Kirsty Wilson, J. Murray, C. Jamieson, A. Watson (2017)
Cyrene as a Bio-Based Solvent for the Suzuki–Miyaura Cross-CouplingSynlett, 29
M. Bruyn, Jiajun Fan, V. Budarin, D. Macquarrie, L. Gomez, Rachael Simister, T. Farmer, W. Raverty, S. McQueen-Mason, J. Clark (2016)
A new perspective in bio-refining: levoglucosenone and cleaner lignin from waste biorefinery hydrolysis lignin by selective conversion of residual saccharidesEnergy and Environmental Science, 9
Bradley Reid, S. Reed (2016)
Improved methods for evaluating the environmental impact of nanoparticle synthesis†.Green chemistry : an international journal and green chemistry resource : GC, 18 15
I. Tsypysheva, F. Valeev, E. Vasil’eva, L. Spirikhin, G. Tolstikov (2000)
Stereochemical differentiation in the reactions of organometallic reagents with levoglucosenone and some of its dihydro derivativesRussian Chemical Bulletin, 49
A. Tagirov, Y. Galimova, L. Faizullina, L. Spirikhin, S. Salikhov, F. Valeev (2017)
Cross-aldol reactions of levoglucosenone and its derivatives with cyclohex-1-en-1-ol ethersRussian Journal of Organic Chemistry, 53
S. Abate, P. Lanzafame, S. Perathoner, G. Centi (2015)
New Sustainable Model of Biorefineries: Biofactories and Challenges of Integrating Bio- and Solar Refineries.ChemSusChem, 8 17
D. Constable, P. Dunn, J. Hayler, G. Humphrey, J. Leazer, R. Linderman, K. Lorenz, J. Manley, B. Pearlman, A. Wells, A. Zaks, Tony Zhang (2007)
Key green chemistry research areas—a perspective from pharmaceutical manufacturersGreen Chemistry, 9
S. Kyne, J. Camp (2017)
Use of Monosaccharides in Metal-Catalyzed Coupling ReactionsACS Sustainable Chemistry & Engineering, 5
Saimeng Jin, Fergal Byrne, C. McElroy, James Sherwood, J. Clark, A. Hunt (2017)
Challenges in the development of bio-based solvents: a case study on methyl(2,2-dimethyl-1,3-dioxolan-4-yl)methyl carbonate as an alternative aprotic solvent.Faraday discussions, 202
V. Brel, A. Samet, L. Konyushkin, A. Stash, V. Belsky, V. Semenov (2015)
Levoglucosenone-derived precursors for the stereoselective synthesis of methylene-expanded analogues of C-nucleosidesMendeleev Communications, 25
Ariel Sarotti, R. Spanevello, A. Suarez (2007)
An efficient microwave-assisted green transformation of cellulose into levoglucosenone. Advantages of the use of an experimental design approachGreen Chemistry, 9
H. Salavagione, James Sherwood, M. Bruyn, V. Budarin, G. Ellis, J. Clark, P. Shuttleworth (2017)
Identification of High Performance Solvents for the Sustainable Processing of GrapheneGreen Chemistry, 19
A. Lanctôt, T. Attard, James Sherwood, C. McElroy, A. Hunt (2016)
Synthesis of cholesterol-reducing sterol esters by enzymatic catalysis in bio-based solvents or solvent-freeRSC Advances, 6
Giulia Paggiola, A. Hunt, C. McElroy, James Sherwood, J. Clark (2014)
Biocatalysis in bio-derived solvents: an improved approach for medium optimisationGreen Chemistry, 16
Fergal Byrne, Saimeng Jin, Giulia Paggiola, Tabitha Petchey, J. Clark, T. Farmer, A. Hunt, C. McElroy, James Sherwood (2016)
Tools and techniques for solvent selection: green solvent selection guidesSustainable Chemical Processes, 4
D. Rasina, Aurora Lombi, S. Santoro, F. Ferlin, L. Vaccaro (2016)
Searching for novel reusable biomass-derived solvents: furfuryl alcohol/water azeotrope as a medium for waste-minimised copper-catalysed azide–alkyne cycloadditionGreen Chemistry, 18
Y. Halpern, R. Riffer, A. Broido (1973)
Levoglucosenone (1,6-anhydro-3,4-dideoxy-.DELTA.3-.beta.-D-pyranosen-2-one). Major product of the acid-catalyzed pyrolysis of cellulose and related carbohydratesJournal of Organic Chemistry, 38
M. Tobiszewski, J. Namieśnik, F. Pena-Pereira (2017)
Environmental risk-based ranking of solvents using the combination of a multimedia model and multi-criteria decision analysisGreen Chemistry, 19
A. Samet, M. Niyazymbetov, V. Semenov, A. Laikhter, Dennis Evans (1996)
Comparative Studies of Cathodically-Promoted and Base-Catalyzed Michael Addition Reactions of Levoglucosenone.The Journal of organic chemistry, 61 25
F. Pena-Pereira, A. Kloskowski, J. Namieśnik (2015)
Perspectives on the replacement of harmful organic solvents in analytical methodologies: a framework toward the implementation of a generation of eco-friendly alternativesGreen Chemistry, 17
Denis Prat, Andy Wells, J. Hayler, H. Sneddon, C. McElroy, Sarah Abou-Shehada, P. Dunn (2016)
CHEM21 selection guide of classical- and less classical-solventsGreen Chemistry, 18
N. Agrawal, S. Bahekar, P. Sarode, Sanjio Zade, H. Chandak (2015)
L-Proline nitrate: a recyclable and green catalyst for the synthesis of highly functionalized piperidinesRSC Advances, 5
Steven Craythorne, K. Anderson, F. Lorenzini, Christina McCausland, Emily Smith, P. Licence, A. Marr, P. Marr (2009)
The co-entrapment of a homogeneous catalyst and an ionic liquid by a sol-gel method: recyclable ionogel hydrogenation catalysts.Chemistry, 15 29
A. Corma, S. Iborra, A. Velty (2007)
Chemical routes for the transformation of biomass into chemicals.Chemical reviews, 107 6
Wenbiao Wu, Ke-qiang Qiu (2014)
Vacuum co-pyrolysis of Chinese fir sawdust and waste printed circuit boards. Part I: Influence of mass ratio of reactantsJournal of Analytical and Applied Pyrolysis, 105
M. Jung, M. Kiankarimi (1998)
Synthesis of Methylene-Expanded 2‘,3‘-DideoxyribonucleosidesJournal of Organic Chemistry, 63
S. Lawrenson, M. North, Fanny Peigneguy, A. Routledge (2017)
Greener solvents for solid-phase synthesisGreen Chemistry, 19
Zhi-bo Zhang, Q. Lu, Xiao-ning Ye, Ti-peng Wang, Xianhua Wang, C. Dong (2015)
Selective Production of Levoglucosenone from Catalytic Fast Pyrolysis of Biomass Mechanically Mixed with Solid Phosphoric Acid CatalystsBioEnergy Research, 8
F. Shafizadeh, Peter Chin (1977)
Preparation of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and some derivatives thereofCarbohydrate Research, 58
Kirsty Wilson, A. Kennedy, J. Murray, B. Greatrex, C. Jamieson, A. Watson (2016)
Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulationBeilstein Journal of Organic Chemistry, 12
Hai Phuong, Levente Cseri, G. Whitehead, Arthur Garforth, P. Budd, G. Szekely (2017)
Environmentally benign and diastereoselective synthesis of 2,4,5-trisubstituted-2-imidazolinesRSC Advances, 7
Marian Bryan, Louis Diorazio, Zhongbo Fei, K. Fraunhoffer, John Hayler, Matthew Hickey, S. Hughes, Mark McLaws, Paul Richardson, Gheorghe‐Doru Roiban, Markus Schober, Austin Smith, Alan Steven, Timothy White, Stijn Wuyts, Jingjun Yin (2018)
Green Chemistry Articles of Interest to the Pharmaceutical IndustryOrganic Process Research & Development
Siddarth Krishna, Theodore Walker, J. Dumesic, G. Huber (2017)
Kinetics of Levoglucosenone Isomerization.ChemSusChem, 10 1
Fei Cao, Thomas Schwartz, D. McClelland, Siddarth Krishna, J. Dumesic, G. Huber (2015)
Dehydration of cellulose to levoglucosenone using polar aprotic solventsEnergy and Environmental Science, 8
Huiyan Zhang, Meng Xin, Chao Liu, Yao Wang, R. Xiao (2017)
Selective low-temperature pyrolysis of microcrystalline cellulose to produce levoglucosan and levoglucosenone in a fixed bed reactorFuel Processing Technology, 167
Desi Gharib, Shaun Gietman, F. Malherbe, S. Moulton (2017)
High yield, solid exfoliation and liquid dispersion of graphite driven by a donor-acceptor interactionCarbon, 123
Denis Prat, J. Hayler, Andy Wells (2014)
A survey of solvent selection guidesGreen Chemistry, 16
Xinde Wang, Shuai Leng, Jiaqi Bai, Hu Zhou, Xing Zhong, G. Zhuang, Jianguo Wang (2015)
Role of pretreatment with acid and base on the distribution of the products obtained via lignocellulosic biomass pyrolysisRSC Advances, 5
James Sherwood, M. bruyn, A. Constantinou, Laurianne Moity, C. McElroy, T. Farmer, Tony Duncan, W. Raverty, A. Hunt, J. Clark (2014)
Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents.Chemical communications, 50 68
Andree Iemhoff, James Sherwood, C. McElroy, A. Hunt (2018)
Towards sustainable kinetic resolution, a combination of bio-catalysis, flow chemistry and bio-based solventsGreen Chemistry, 20
M. Sathish, S. Silambarasan, B. Madhan, J. Rao (2016)
Exploration of GSK'S solvent selection guide in leather industry: a CSIR-CLRI tool for sustainable leather manufacturingGreen Chemistry, 18
The development of green solvents is one of the key tenets of Green Chemistry as solvents account for the majority of waste stemming from the production of the chemicals on which we have all come to rely. An important class of solvents is the dipolar aprotics, which include N,N‐dimethylformamide (DMF) and N‐methyl‐2‐pyrrolidone (NMP). In addition to being derived from non‐renewable resources, these solvents are also under increased regulatory pressures that will limit their industrial applications. This Concept concerns the bio‐available solvent Cyrene (dihydrolevoglucosenone) as a potential replacement for toxic dipolar aprotic solvents. An emphasis is placed on examining the strengths and weaknesses of Cyrene as a solvent and is accomplished by looking at the synthesis, derivatization, and application in synthetic protocols of Cyrene. With respect to the Twelve Principles of Green Chemistry, this Concept describes a bio‐available solvent that should have a disruptive effect on the use of traditional industrial dipolar aprotic solvents.
ChemSusChem - Chemistry and Sustainability, Energy & Materials – Wiley
Published: Sep 21, 2019
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