A critical look at reactions in class I and II gas-expanded liquids using CO2 and other gases

This short review aims to give a summary of the publications on reactions in class I and II gas-expanded liquids (GXLs) (those with organic or aqueous liquid components), and to draw conclusions from the trends in the current literature.

[1]  C. Eckert,et al.  CO2-Protected Amine Formation from Nitrile and Imine Hydrogenation in Gas-Expanded Liquids , 2004 .

[2]  C. Eckert,et al.  Probing the cybotactic region in gas-expanded liquids (GXLs). , 2006, Accounts of chemical research.

[3]  J. Levec,et al.  Hydrogen solubility in CO2-expanded 2-propanol and in propane-expanded 2-propanol determined by an acoustic sensor , 2007 .

[4]  U. R. Pillai,et al.  Selective hydrogenation of maleic anhydride to gamma-butyrolactone over Pd/Al2O3 catalyst using supercritical CO2 as solvent. , 2002, Chemical communications.

[5]  J. Grunwaldt,et al.  Continuous catalytic oxidation of solid alcohols in supercritical CO2: A parametric and spectroscopic study of the transformation of cinnamyl alcohol over Pd/Al2O3 , 2006 .

[6]  C. Wai,et al.  pH-Defining Equilibrium between Water and Supercritical CO2. Influence on SFE of Organics and Metal Chelates , 1995 .

[7]  M. Shirai,et al.  Low temperature hydrogenation of 1- and 2-phenylethanols with noble metal catalysts in supercritical carbon dioxide , 2006 .

[8]  F. Boury,et al.  Formation and rheological properties of the supercritical CO2-water pure interface. , 2005, The journal of physical chemistry. B.

[9]  Franklin M. Orr,et al.  Diffusion of CO2 at Reservoir Conditions: Models and Measurements , 1988 .

[10]  W. Leitner.  The coordination chemistry of carbon dioxide and its relevance for catalysis: a critical survey , 1996 .

[11]  Ross R. Weikel,et al.  Reversible in situ acid formation for β-pinene hydrolysis using CO2 expanded liquid and hot water , 2004 .

[12]  C. Eckert,et al.  Solvent Effects on the Kinetics of a Diels−Alder Reaction in Gas-Expanded Liquids , 2008 .

[13]  Phillip E. Savage,et al.  Recent advances in acid- and base-catalyzed organic synthesis in high-temperature liquid water , 2004 .

[14]  D. Prajapati,et al.  Recent advances in the application of supercritical fluids for carbon–carbon bond formation in organic synthesis , 2004 .

[15]  K. Kuczera,et al.  Prediction of phase equilibria and transport properties in carbon-dioxide expanded solvents by molecular simulation , 2007 .

[16]  Masahiro Sato,et al.  An exceptionally rapid and selective hydrogenation of 2-cyclohexen-1-one in supercritical carbon dioxide. , 2009, Chemical communications.

[17]  C. Eckert,et al.  Neoteric solvents for asymmetric hydrogenation: supercritical fluids, ionic liquids, and expanded ionic liquids , 2003 .

[18]  C. Eckert,et al.  Bubble and Dew Point Measurements of the Ternary System Carbon Dioxide + Methanol + Hydrogen at 313.2 K , 2005 .

[19]  Huanfeng Jiang,et al.  An Efficient and Eco-friendly Process for the Conversion of Carbon Dioxide into Oxazolones and Oxazolidinones under Supercritical Conditions , 2008 .

[20]  Alessandra Basso,et al.  Biocatalysis in non-conventional media—ionic liquids, supercritical fluids and the gas phase , 2007 .

[21]  C. Eckert,et al.  Olefin Epoxidations Using Supercritical Carbon Dioxide and Hydrogen Peroxide without Added Metallic Catalysts or Peroxy Acids , 2002 .

[22]  W. Tumas,et al.  Enhanced catalyst reactivity and separations using water/carbon dioxide emulsions [5] , 1999 .

[23]  Jianping Yin,et al.  Solubility of hydrogen in toluene for the ternary system H2+CO2+toluene from 305 to 343 K and 1.2 to 10.5 MPa , 2006 .

[24]  Zhimin Liu,et al.  Critical points and phase behavior of toluene-CO2 and toluene-H2-CO2 mixture in CO2-rich region , 2000 .

[25]  M. Shirai,et al.  Enhancement of Glycerol Conversion to Acetol in High-temperature Liquid Water by High-pressure Carbon Dioxide , 2008 .

[26]  Ross R. Weikel,et al.  Self-neutralizing in situ acid catalysis for single-pot synthesis of iodobenzene and methyl yellow in CO2-expanded methanol , 2007 .

[27]  D. Ferri,et al.  Supercritical carbon dioxide: an inert solvent for catalytic hydrogenation? , 2005, The journal of physical chemistry. B.

[28]  J. Grunwaldt,et al.  Continuous catalytic "one-pot" multi-step synthesis of 2-ethylhexanal from crotonaldehyde. , 2007, Chemical communications.

[29]  A. Milewska,et al.  Biphasic hydrogenation of α-pinene in high-pressure carbon dioxide , 2005 .

[30]  M. Stadtherr,et al.  Enhanced Solubility of Oxygen and Carbon Monoxide in CO2-Expanded Liquids , 2006 .

[31]  A. Baiker,et al.  Palladium-catalysed dehydrogenation of 1-phenylethanol in dense carbon dioxide , 2005 .

[32]  P. Canu,et al.  Kinetic experiments and modeling of a three-phase catalytic hydrogenation reaction in supercritical CO2 , 1999 .

[33]  Wesch,et al.  Measurement of the Mass Transfer into Single Drops in the System of Water/Supercritical Carbon Dioxide. , 2000, Journal of colloid and interface science.

[34]  J. Grunwaldt,et al.  IR spectroscopy and phase behavior studies of the catalytic synthesis of propylene carbonate: Expanded liquid versus supercritical fluid , 2006 .

[35]  M. Duduković,et al.  Mass transfer effects during homogeneous 1-octene hydroformylation in CO2-expanded solvent: Modeling and experiments , 2007 .

[36]  D. H. Busch,et al.  CO(2)-expanded solvents: unique and versatile media for performing homogeneous catalytic oxidations. , 2002, Journal of the American Chemical Society.

[37]  Y. Ikushima,et al.  Completely selective hydrogenation of trans-cinnamaldehyde to cinnamyl alcohol promoted by a Ru–Pt bimetallic catalyst supported on MCM-48 in supercritical carbon dioxide , 2003 .

[38]  N. Foster,et al.  Viscosity measurements on saturated gas expanded liquid systems—Acetone and carbon dioxide , 2008 .

[39]  C. Eckert,et al.  Sustainable Reactions in Tunable Solvents , 2004 .

[40]  Takeshi Sako,et al.  Synthesis of dimethyl carbonate from carbon dioxide: catalysis and mechanism , 2000 .

[41]  A. Baiker,et al.  Continuous Enantioselective Hydrogenation of Ethyl Pyruvate in “Supercritical” Ethane: Relation between Phase Behavior and Catalytic Performance , 2001 .

[42]  H. Vogel,et al.  Heterogeneous Catalysis in Supercritical Media: 1. Carbon Dioxide , 2008 .

[43]  Andrew I. Cooper,et al.  Polymer synthesis and processing using supercritical carbon dioxide , 2000 .

[44]  E. Schlünder,et al.  The effect of concentration on the liquid phase diffusivities in the binary systems carbon dioxide-oleic acid, carbon dioxide-methyl myristate and carbon dioxide-methyl palmitate at high pressures , 1996 .

[45]  J. Grunwaldt,et al.  Selective oxidation of benzyl alcohol to benzaldehyde in “supercritical” carbon dioxide , 2004 .

[46]  Walter Leitner,et al.  Supercritical carbon dioxide as a green reaction medium for catalysis. , 2002, Accounts of chemical research.

[47]  S. Karmee,et al.  Technical aspects of biocatalysis in non‐CO2‐based supercritical fluids , 2008, Biotechnology journal.

[48]  R. He,et al.  Synthesis of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture in the presence of bifunctional catalyst , 2002 .

[49]  F. Lucien,et al.  Catalytic chain transfer polymerisation of CO2-expanded methyl methacrylate , 2006 .

[50]  G. Brunner,et al.  Phase equilibrium-driven selective hydrogenation of limonene in high-pressure carbon dioxide , 2007 .

[51]  M. Mazzotti,et al.  Vapor−Liquid Mass Transfer during Gas Antisolvent Recrystallization: Modeling and Experiments , 2003 .

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[53]  P. Jessop.  Homogeneous catalysis using supercritical fluids : Recent trends and systems studied , 2006 .

[54]  Eric J. Beckman,et al.  Supercritical and near-critical CO2 in green chemical synthesis and processing , 2004 .

[55]  M. Poliakoff,et al.  Selective catalytic hydrogenation of organic compounds in supercritical fluids as a continuous process , 1998 .

[56]  Haiyang Cheng,et al.  Hydrogenation of o-chloronitrobenzene to o-chloroaniline over Pd/C in supercritical carbon dioxide , 2008 .

[57]  M. N. Ponte,et al.  The influence of phase behavior on reactions at supercritical conditions : The hydrogenation of α-pinene , 2001 .

[58]  F. Dehghani,et al.  Synthesis, Purification, and Micronization of Pharmaceuticals Using the Gas Antisolvent Technique , 2000 .

[59]  David Hinks,et al.  Synthesis of N,N‐diethyl‐N‐{4‐[(E)‐(4‐nitrophenyl)diazenyl]phenyl}amine via in situ diazotisation and coupling in supercritical carbon dioxide , 2002 .

[60]  R. Oakes,et al.  The use of supercritical fluids in synthetic organic chemistry , 2001 .

[61]  H. Ghaziaskar,et al.  Continuous synthesis of glycerol acetates in supercritical carbon dioxide using Amberlyst 15 , 2009 .

[62]  P. Tontiwachwuthikul,et al.  Dynamic interfacial tension method for measuring gas diffusion coefficient and interface mass transfer coefficient in a liquid , 2006 .

[63]  A. Chatterjee,et al.  Pd-catalyzed completely selective hydrogenation of conjugated and isolated CC of citral (3,7-dimethyl-2, 6-octadienal) in supercritical carbon dioxide , 2004 .

[64]  V. A. Grinberg,et al.  Electrocarboxylation of α,ω-dihaloperfluoroalkanes and of perfluoroalkylhalides in a near-critical and supercritical CO2-methanol medium , 1998 .

[65]  D. Vos,et al.  Green synthesis of carbamates from CO2, amines and alcohols , 2008 .

[66]  W. Leitner,et al.  Highly efficient enantioselective catalysis in supercritical carbon dioxide using the perfluoroalkyl-substituted ligand (R,S)-3-H2F6-BINAPHOS , 2001 .

[67]  W. Leitner,et al.  Inverted supercritical carbon dioxide/aqueous biphasic media for rhodium-catalyzed hydrogenation reactions. , 2007, Chemistry.

[68]  H. Teng,et al.  Mass transfer of CO2 through liquid CO2–water interface , 1998 .

[69]  Chung-Sung Tan,et al.  Measurement of diffusion coefficients of p-chloronitrobenzene in CO2-expanded methanol , 2008 .

[70]  V. A. Grinberg,et al.  Electrocarboxylation of 1,4-dibromobut-2-ene in a CO2-DMF liquid mixture , 1997 .

[71]  P. Licence,et al.  Friedel−Crafts Alkylation of Anisole in Supercritical Carbon Dioxide: A Comparative Study of Catalysts , 2005 .

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[74]  J. Iborra,et al.  Enzymatic Catalysis in Ionic Liquids and Supercritical Carbon Dioxide Biphasic Systems , 2009 .

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[76]  P. Jessop.  Homogeneously-catalyzed syntheses in supercritical fluids , 1998 .

[77]  B. Subramaniam,et al.  1-Butene + Isobutane Reactions on Solid Acid Catalysts in Dense CO2-Based Reaction Media: Experiments and Modeling , 2004 .

[78]  Ross R. Weikel,et al.  Self-neutralizing in situ Acid Catalysts from CO2 , 2006 .

[79]  Zeljko Knez,et al.  High Pressure Process Technology—Quo Vadis? , 2004 .

[80]  U. R. Pillai,et al.  Hydrogenation of 4-Oxoisophorone over a Pd/Al2O3 Catalyst under Supercritical CO2 Medium , 2003 .

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[84]  T. Ikariya,et al.  Supercritical fluids as reaction media for molecular catalysis , 2000 .

[85]  W. Leitner,et al.  Gaining pH-control in water/carbon dioxide biphasic systems , 2007 .

[86]  B. Han,et al.  Precipitation polymerization of methyl methacrylate in tetrahydrofuran with compressed CO2 as antisolvent , 2003 .

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[88]  J. Grunwaldt,et al.  Benzyl alcohol oxidation in supercritical carbon dioxide: spectroscopic insight into phase behaviour and reaction mechanism. , 2005, Physical chemistry chemical physics : PCCP.

[89]  A. Baiker,et al.  Hydrogenation of citral over Pd/alumina: comparison of supercritical CO2 and conventional solvents in continuous and batch reactors , 2004 .

[90]  D. Young,et al.  Maleic anhydride hydrogenation over Pd/Al2O3 catalyst under supercritical CO2 medium , 2003 .

[91]  M. Arai,et al.  Recyclability of water-soluble ruthenium–phosphine complex catalysts in multiphase selective hydrogenation of cinnamaldehyde using toluene and pressurized carbon dioxide , 2006 .

[92]  M. Maroncelli,et al.  Solvation and solvatochromism in CO2-expanded liquids. 2. Experiment-simulation comparisons of preferential solvation in three prototypical mixtures. , 2007, The journal of physical chemistry. B.

[93]  A. Baiker,et al.  Continuous oxidation of benzyl alcohol in “supercritical” carbon dioxide , 2001 .

[94]  Hong Jin,et al.  Homogeneous catalytic hydroformylation of 1-octene in CO2-expanded solvent media , 2004 .

[95]  R. Smith,et al.  Proton concentration of supercritical water and high-concentrated carbon dioxide mixture using UV-vis spectroscopy , 2007 .

[96]  Zhimin Liu,et al.  Pressure Tuning of Reaction Equilibrium of Esterification of Acetic Acid with Ethanol in Compressed CO2 , 2001 .

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[101]  Zhimin Liu,et al.  Polymerization of styrene in solutions with compressed carbon dioxide as antisolvent , 2001 .

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[114]  B. Han,et al.  Enhancing reaction rate of transesterification of glycerol monostearate and methanol by CO(2). , 2007, The journal of physical chemistry. A.

[115]  M. Shirai,et al.  Stereoselective hydrogenation of tert-butylphenols over charcoal-supported rhodium catalyst in supercritical carbon dioxide solvent , 2007 .

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[119]  M. Shirai,et al.  Enhancement of cyclic ether formation from polyalcohol compounds in high temperature liquid water by high pressure carbon dioxide , 2009 .

[120]  M. J. Cocero,et al.  Micronization processes with supercritical fluids: fundamentals and mechanisms. , 2008, Advanced drug delivery reviews.

[121]  M. Abraham,et al.  Hydroformylation of 1-hexene in supercritical carbon dioxide using a heterogeneous rhodium catalyst. 3. Evaluation of solvent effects , 2002 .

[122]  M. Poliakoff,et al.  The Continuous Acid-Catalyzed Dehydration of Alcohols in Supercritical Fluids: A New Approach to the Cleaner Synthesis of Acetals, Ketals, and Ethers with High Selectivity , 1999 .

[123]  D. C. Conrad,et al.  Phase equilibria and thermophysical properties of carbon dioxide-expanded fluorinated solvents , 2003 .

[124]  Bin Xu,et al.  Diffusion of water in liquid and supercritical carbon dioxide: An NMR study , 2003 .

[125]  Sandro Campestrini and Umberto Tonellato.  Selective Catalytic Oxidations in Supercritical Carbon Dioxide , 2005 .

[126]  B. Han,et al.  Influence of Compressed Carbon Dioxide on the Oxidation of Cyclohexane with Hydrogen Peroxide in Acetic Acid , 2006 .

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[128]  M. Muldoon,et al.  "Solventless" continuous flow homogeneous hydroformylation of 1-octene. , 2007, Dalton transactions.

[129]  C. Eckert,et al.  CO2-Catalyzed Acetal Formation in CO2-Expanded Methanol and Ethylene Glycol , 2004 .

[130]  Anlian Zhu,et al.  Effect of pressure on the selectivity for the esterification of ethylene glycol with propionic acid in supercritical CO2. , 2007, The journal of physical chemistry. B.

[131]  B. Subramaniam,et al.  Autoxidation of 2,6-di-tert-butylphenol with cobalt Schiff base catalysts by oxygen in CO2-expanded liquids , 2004 .

[132]  R. Smith,et al.  Temperature dependence of dielectric spectra of carbon dioxide and methanol mixtures at high-pressures , 2002 .

[133]  Kent A. Pennybaker,et al.  Economic and Environmental Impact Analyses of Catalytic Olefin Hydroformylation in CO2-Expanded Liquid (CXL) Media , 2007 .

[134]  Chung-Sung Tan,et al.  Hydrogenation of p-chloronitrobenzene by Ni-B nanocatalyst in CO2-expanded methanol , 2007 .

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[137]  J. Grunwaldt,et al.  Palladium Supported on an Acidic Resin : A Unique Bifunctional Catalyst for the Continuous Catalytic Hydrogenation of Organic Compounds in Supercritical Carbon Dioxide , 2008 .

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