Ionic liquids and supercritical carbon dioxide: green and alternative reaction media for chemical processes

References

Abro R, Abdeltawab AA, Al-Deyab SS, Yu GR, Qazi AB, Gao SR, Chen XC. A review of extractive desulfurization of fuel oils using ionic liquids. RSC Adv 2014; 4: 35302–35317.10.1039/C4RA03478CSearch in Google Scholar

Adsul MG, Terwadkar AP, Varma AJ, Gokhale DV. Cellulases from Penicillium janthinellum mutants: solid-state production and their stability in ionic liquids. BioResources 2009; 4: 1670–1681.10.15376/biores.4.4.1670-1681Search in Google Scholar

Akien GR, Poliakoff M. A critical look at reactions in class I and II gas-expanded liquids using CO₂ and other gases. Green Chem 2009; 11: 1083–1100.10.1039/b904097hSearch in Google Scholar

Alonso L, Arce A, Francisco M, Rodriguez O, Soto A. Gasoline desulfurization using extraction with [C8mim][BF₄] ionic liquid. AIChE J 2007; 53: 3108–3115.10.1002/aic.11337Search in Google Scholar

Alonso L, Arce A, Francisco M, Soto A. Extraction ability of nitrogen-containing compounds involved in the desulfurization of fuels by using ionic liquids. J Chem Eng Data 2010; 55: 3262–3267.10.1021/je100075mSearch in Google Scholar

Amandi R, Licence P, Ross SK, Aaltonen O, Poliakoff M. Friedel-crafts alkylation of anisole in supercritical carbon dioxide: a comparative study of catalysts. Org Process Res Dev 2005; 9: 451–456.10.1021/op050044ySearch in Google Scholar

Ansari IA, Gree R. Tempo-catalyzed aerobic oxidation of alcohols to aldehydes and ketones in ionic liquid [Bmim][PF₆]. Org Lett 2002; 4: 1507–1509.10.1021/ol025721cSearch in Google Scholar

Berthold H, Schotten T, Hönig H. Transfer hydrogenation in ionic liquids under microwave irradiation. Synthesis-Stuttgart 2002; 1607–1610.10.1055/s-2002-33349Search in Google Scholar

Bhanage BM, Ikushima Y, Shirai M, Arai M. Heck reactions using water-soluble metal complexes in supercritical carbon dioxide. Tetrahedron Lett 1999; 40: 6427–6430.10.1016/S0040-4039(99)01197-1Search in Google Scholar

Birnbaum ER, Le Lacheur RM, Horton AC, Tumas W. Metalloporphyrin-catalyzed homogeneous oxidation in supercritical carbon dioxide. J Mol Catal A-Chem 1999; 139: 11–24.10.1016/S1381-1169(98)00172-1Search in Google Scholar

Brown RA, Pollet P, McKoon E, Eckert CA, Liotta CL, Jessop PG. Asymmetric hydrogenation and catalyst recycling using ionic liquid and supercritical carbon dioxide. J Am Chem Soc 2001; 123: 1254–1255.10.1021/ja005718tSearch in Google Scholar PubMed

Bui TLT, Korth W, Jess A. Influence of acidity of modified chloroaluminate based ionic liquid catalysts on alkylation of iso-butene with butene-2. Catal Commun 2012; 25: 118–124.10.1016/j.catcom.2012.03.018Search in Google Scholar

Cantone S, Hanefeld U, Basso A. Biocatalysis in non-conventional media-ionic liquids, supercritical fluids and the gas. Green Chem 2007; 9: 954–971.10.1039/b618893aSearch in Google Scholar

Cao RM, Xin JY, Zhang Z, Liu Z, Lu XM, Ren BZ, Zhang SJ. Efficient conversion of α-angelica lactone into γ-valerolactone with ionic liquids at room temperature. ACS Sustain Chem Eng 2014; 2: 902–909.10.1021/sc4005185Search in Google Scholar

Chateauneuf JE, Nie K. An investigation of a friedel-crafts alkylation reaction in homogeneous supercritical CO₂ and under subcritical and splitphase reaction conditions. Adv Environ Res 2000; 4: 307–312.10.1016/S1093-0191(00)00030-7Search in Google Scholar

Chauvin Y, Gaillard JF, Quang DV, Andrews JW. IFP dimersol process for dimerization of C₃ and C₄ olefinic cuts. Chem Ind 1974; 45: 375–378.Search in Google Scholar

Chauvin Y, Mussmann L, Olivier H. A novel class of versatile solvents for two-phase catalysis: hydrogenation, isomerization, and hydroformylation of alkenes catalyzed by rhodium complexes in liquid 1,3-dialkylimidazolium salts. Angew Chem Int Ed 1996; 34: 2698–2700.10.1002/anie.199526981Search in Google Scholar

Chen WP, Xu LJ, Xiao JL. Palladium-catalyzed synthesis of aqueous, fluorous, and supercritical CO₂-soluble phosphines. Org Lett 2000; 2: 2675–2677.10.1021/ol006203+Search in Google Scholar PubMed

Chen XC, Guan YW, Abdeltawab AA, Al-Deyab SS, Yuan XL, Wang CY, Yu GR. Using functional acidic ionic liquids as both extractant and catalyst in oxidative desulfurization of diesel fuel: an investigation of real feedstock. Fuel 2015; 146: 6–12.10.1016/j.fuel.2014.12.091Search in Google Scholar

Cheng XY, Li KF, Wang QJ, Wang CY, Ying TK. Oxidation of alcohols to aldehydes and ketones using selenium ionic liquid. Chin Chem Lett 2012; 23: 801–804.10.1016/j.cclet.2012.05.019Search in Google Scholar

Cheng Q, Xu SQ, Wang X, Guo CL. Ionic liquid-coated nickel phosphide catalysts for selective hydrodesulfurization. Chem Eng Technol 2013; 36: 228–232.10.1002/ceat.201200423Search in Google Scholar

Chhikara BS, Chandra R, Tandon V. Oxidation of alcohols with hydrogen peroxide catalyzed by a new imidazolium ion based phosphotungstate complex in ionic liquid. J Catal 2005; 230: 436–439.10.1016/j.jcat.2004.12.022Search in Google Scholar

Cole-Hamilton DJ. Homogeneous catalysis – new approaches to catalyst separation, recovery, and recycling. Science 2003; 299: 1702–1706.10.1126/science.1081881Search in Google Scholar PubMed

Conte V, Floris B, Galloni P, Mirruzzo V, Scarso A, Sordi D, Strukul G. The Pt(II)-catalyzed baeyer-villiger oxidation of cyclohexanone with H₂O₂ in ionic liquids. Green Chem 2005; 7: 262–266.10.1039/b416923aSearch in Google Scholar

Cui P, Zhao GY, Ren HL, Huang J, Zhang SJ. Ionic liquid enhanced alkylation of iso-butane and 1-butene. Catal Today 2013; 200: 30–35.10.1016/j.cattod.2012.06.008Search in Google Scholar

Dai F, Muhammad Y, Gong X, Li CS, Li ZX, Zhang SJ. Low-temperature and low-pressure fuel hydrodesulfurization by solid catalyst coupling with ionic liquids. Fuel 2014; 134: 74–80.10.1016/j.fuel.2014.05.027Search in Google Scholar

Dawodu FA, Ayodele OO, Xin JY, Zhang SJ, Yan DX. Effective conversion of non-edible oil with high free fatty acid into biodiesel by sulphonated carbon catalyst. Appl Energ 2014a; 114: 819–826.10.1016/j.apenergy.2013.10.004Search in Google Scholar

Dawodu FA, Ayodele OO, Xin JY, Zhang SJ. Dimethyl carbonate mediated production of biodiesel at different reaction temperatures. Renew Energ 2014b; 68: 581–587.10.1016/j.renene.2014.02.036Search in Google Scholar

De Diego T, Lozano P, Abad MA, Steffensky K, Vaultier M, Iborra JL. On the nature of ionic liquids and their effects on lipases that catalyze ester synthesis. J Biotechnol 2009; 140: 234–241.10.1016/j.jbiotec.2009.01.012Search in Google Scholar PubMed

De Diego T, Manjón A, Lozano P, Iborra JL. A recyclable enzymatic biodiesel production process in ionic liquids. Bioresour Technol 2011; 102: 6336–6339.10.1016/j.biortech.2011.02.071Search in Google Scholar PubMed

De Los Ríos AP, Hernández-Fernández FJ, Martínez FA, Rubio M, Víllora G. The effect of ionic liquid media on activity, selectivity and stability of Candida antarctica lipase B in transesterification reactions. Biocatal Biotransform 2007; 25: 151–156.10.1080/10242420701379213Search in Google Scholar

Deive FJ, Ruivo D, Rodrigues JV, Gomes CM, Sanromán MA, Rebelo LPN, Esperança JMSS, Rodríguez A. On the hunt for truly biocompatible ionic liquids for lipase-catalyzed reactions. RSC Adv 2015; 5: 3386–3389.10.1039/C4RA15021JSearch in Google Scholar

Dupont J, Fonseca GS, Umpierre AP, Fichtner PFP, Teixeira SR. Transition-metal nanoparticles in imidazolium ionic liquids: recyclable catalysts for biphasic hydrogenation reactions. J Am Chem Soc 2002; 124: 4228–4229.10.1021/ja025818uSearch in Google Scholar

Erkey C, Diz EL, Suss-Fink G, Dong X. Hydroformylation of ethylene in supercritical carbon dioxide using Ru₃(CO)₁₂ as a catalyst precursor. Catal Commun 2002; 3: 213–219.10.1016/S1566-7367(02)00093-6Search in Google Scholar

Fan MM, Yang J, Jiang PP, Zhang PB, Li SS. Synthesis of novel dicationic basic ionic liquids and its catalytic activities for biodiesel production. RSC Adv 2013; 3: 752–756.10.1039/C2RA22233GSearch in Google Scholar

Favre F, Olivier-Bourbigou H, Commereuc D, Saussine L. Hydroformylation of 1-hexene with rhodium in non-aqueous ionic liquids: how to design the solvent and the ligand to the reaction. Chem Commun 2001; 1360–1361.10.1039/b104155jSearch in Google Scholar

Fonseca GS, Scholten JD, Dupont J. Iridium nanoparticles prepared in ionic liquids: an efficient catalytic system for the hydrogenation of ketones. Synlett 2004; 9: 1525–1528.10.1002/chin.200446047Search in Google Scholar

Fráter T, Gubicza L, Szöllősy Á, Bakos J. Enantioselective hydrogenation in ionic liquids: recyclability of the [Rh(COD)(DIPAMP)]BF₄ catalyst in [Bmim][BF₄]. Inorg Chim Acta 2006; 359: 2756–2759.10.1016/j.ica.2005.10.020Search in Google Scholar

Freemantle M. Stressed polymers change color. Chem Eng News 2003; 81: 10.10.1021/cen-v081n051.p010aSearch in Google Scholar

Garcia S, Lourenco NMT, Lousa D, Sequeira AF, Mimoso P, Cabral JMS, Afonso CAM, Barreiros S. A comparative study of biocatalysis in non-conventional solvents: ionic liquids, supercritical fluids and organic media. Green Chem 2004; 6: 466–470.10.1039/B405614KSearch in Google Scholar

Geldbach TJ, Dyson PJ. A versatile ruthenium precursor for biphasic catalysis and its application in ionic liquid biphasic transfer hydrogenation: conventional vs task-specific catalysts. J Am Chem Soc 2004; 126: 8114–8115.10.1021/ja048886kSearch in Google Scholar PubMed

Ginosar DM, Thompson DN, Coates K, Zalewski DJ, Fox RV. Method for reactivating solid catalysts used in alkylation reactions, US Patent 6579821 B1, 2003.Search in Google Scholar

Ginosar DM, Thompson DN, Burch KC. Recovery of alkylation activity in deactivated USY catalyst using supercritical fluids: a comparison of light hydrocarbons. Appl Catal A-Gen 2004; 262: 223–231.10.1016/j.apcata.2003.11.030Search in Google Scholar

Gläser R, Weitkamp J. Supercritical carbon dioxide as a reaction medium for the zeolite-catalyzed alkylation of naphthalene. Ind Eng Chem Res 2003; 42: 6294–6302.10.1021/ie000153vSearch in Google Scholar

Gok Y, Alici B, Cetinkaya E, Ozdemir I, Ozeroglu O. Ionic liquids as solvent for efficient esterification of carboxylic acids with alkyl halides. Turk J Chem 2010; 34: 187–191.10.3906/kim-0904-39Search in Google Scholar

Guernik S, Wolfson A, Herskowitz M, Greenspoon N, Geresh S. A novel system consisting of Rh-DuPHOS and ionic liquid for asymmetric hydrogenations. Chem Commun (Camb) 2001; 2314–2315.10.1039/b107292gSearch in Google Scholar

Habulin M, Primožič M, Knez Ž. Application of ionic liquids in biocatalysis. In: Kokorin A, editor. Ionic liquids: applications and perspectives. InTech. 2011; 461–480.10.5772/15354Search in Google Scholar

Hamill NA, Hardacre C, McMath SEJ. In situ XAFS investigation of palladium species present during the heck reaction in room temperature ionic liquids. Green Chem 2002; 4: 139–142.10.1039/b109844fSearch in Google Scholar

Han X, Poliakoff M. Continuous reactions in supercritical carbon dioxide: problems, solutions and possible ways forward. Chem Soc Rev 2012; 41: 1428–1436.10.1039/c2cs15314aSearch in Google Scholar

Handy ST, Zhang X. Organic synthesis in ionic liquids: the stille coupling. Org Lett 2001; 3: 233–236.10.1021/ol0068849Search in Google Scholar

Hitzler MG, Smail FR, Ross SK, Poliakoff M. Friedel-crafts alkylation in supercritical fluids: continuous, selective and clean. Chem Commun 1998; 359–360.10.1039/a707149cSearch in Google Scholar

Hoff A, Jost C, Prodi-Schwab A, Schmidt FG, Weyershausen B. Ionic liquids: new designer compounds for more efficient chemistry. Elem Degussa Sci Newsl 2004; 9: 10–15.Search in Google Scholar

Hong F, Guo X, Zhang S, Han SF, Yang G, Jonsson LJ. Bacterial cellulose production from cotton-based waste textiles: enzymatic saccharification enhanced by ionic liquid pretreatment. Bioresour Technol 2012; 104: 503–508.10.1016/j.biortech.2011.11.028Search in Google Scholar

Hope K, Stern D, Twomey D. Method for manufacturing ionic liquid catalysts. US Patent 6984605 B2, 2006.10.1016/S1351-4180(06)71591-4Search in Google Scholar

Hou ZS, Han BX, Gao L, Jiang T, Liu ZM, Chang YH, Zhang XG, He J. Wacker oxidation of 1-hexene in 1-N-butyl-3-methylimidazolium hexafluorophosphate ([Bmim][PF₆]), supercritical (sc)CO₂, and scCO₂/[Bmim][PF₆] mixed solvent. N J Chem 2002; 26: 1246–1248.10.1039/b201997cSearch in Google Scholar

Howarth J. Oxidation of aromatic aldehydes in the ionic liquid [Bmim][PF₆]. Tetrahedron Lett 2000; 41: 6627–6629.10.1016/S0040-4039(00)01037-6Search in Google Scholar

Howarth J, James P, Dai J. An exploration of the catalytic sakurai reaction in the moisture stable ionic liquids [Bmim][PF₆] and [Bmim]BF₄. J Mol Catal A-Chem 2004; 214: 143–146.10.1016/j.molcata.2003.09.036Search in Google Scholar

Hu AG, Ngo HL, Lin WB. Remarkable 4,4′-substituent effects on binap: highly enantioselective Ru catalysts for asymmetric hydrogenation of ß-aryl ketoesters and their immobilization in room-temperature ionic liquids. Angew Chem Int Ed 2004; 43: 2501–2504.10.1002/anie.200353415Search in Google Scholar PubMed

Huang J, Jiang T, Han B, Gao H, Chang Y, Zhao G, Wu W. Hydrogenation of olefins using ligand-stabilized palladium nanoparticles in an ionic liquid. Chem Commun 2003; 1654–1655.10.1039/b302750cSearch in Google Scholar

Huang Q, Zhao GY, Zhang SJ, Yang FF. Improved catalytic lifetime of H₂SO₄ for isobutane alkylation with trace amount of ionic liquids buffer. Ind Eng Chem Res 2015; 54: 1464–1469.10.1021/ie504163hSearch in Google Scholar

Itoh T, Akasaki E, Kudo K, Shirakami S. Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: reaction of enzyme anchored to the solvent. Chem Lett 2001; 30: 262–263.10.1246/cl.2001.262Search in Google Scholar

Jain N, Kumar A, Chauhan S, Chauhan SMS. Chemical and biochemical transformations in ionic liquids. Tetrahedron 2005; 61: 1015–1060.10.1016/j.tet.2004.10.070Search in Google Scholar

Jessop PG, Stanley RR, Brown RA, Eckert CA, Liotta CL, Ngo TT, Pollet P. Neoteric solvents for asymmetric hydrogenation: supercritical fluids, ionic liquids, and expanded ionic liquids. Green Chem 2003; 5: 123–128.10.1039/b211894gSearch in Google Scholar

Jia LQ, Jiang HF, Li JH. Palladium(II)-catalyzed oxidation of acrylate esters to acetals in supercritical carbon dioxide. Chem Commun 1999; 985–986.10.1039/a901935iSearch in Google Scholar

Jin X, Xu XF, Zhao K. Amino acid- and imidazolium-tagged chiral pyrrolidinodiphosphine ligands and their applications in catalytic asymmetric hydrogenations in ionic liquid systems. Tetrahedron-Asymmetr 2012; 23: 1058–1067.10.1016/j.tetasy.2012.07.008Search in Google Scholar

Jutz F, Andanson J-M, Baiker A. Ionic liquids and dense carbon dioxide: a beneficial biphasic system for catalysis. Chem Rev 2011; 111: 322–353.10.1021/cr100194qSearch in Google Scholar

Kamiya N, Matsushita Y, Hanaki M, Nakashima K, Narita M, Goto M, Takahashi H. Enzymatic in situ saccharification of cellulose in aqueous-ionic liquid media. Biotechnol Lett 2008; 30: 1037–1040.10.1007/s10529-008-9638-0Search in Google Scholar

Kapucu N, Güvenç A, Mehmetoğlu Ü, Çalimli A. Reactive extraction of organic acids by supercritical CO₂. Rev Chem Eng 1999; 15: 233–244.10.1515/REVCE.1999.15.4.233Search in Google Scholar

Kawasaki I, Tsunoda K, Tsuji T, Yamaguchi T, Shibuta H, Uchida N, Yamashita M, Ohta S. A recyclable catalyst for asymmetric transfer hydrogenation with a formic acid-triethylamine mixture in ionic liquid. Chem Commun (Camb) 2005; 28: 2134–2136.10.1039/B500320BSearch in Google Scholar

Keim W, Vogt D, Waffenschmidt H, Wasserscheid P. New method to recycle homogeneous catalysts from monophasic reaction mixtures by using an ionic liquid exemplified for the Rh-catalysed hydroformylation of methyl-3-pentenoate. J Catal 1999; 186: 481–484.10.1006/jcat.1999.2569Search in Google Scholar

Keskin S, Kayrak-Talay D, Akman U, Hortaçsu Ö. A review of ionic liquids towards supercritical fluid applications. J Supercrit Fluids 2007; 43: 150–180.10.1016/j.supflu.2007.05.013Search in Google Scholar

Kerton FM, Marriott R. Alternative solvents for green chemistry. Cambridge, UK: Royal Society of Chemistry, 2009.10.1039/9781847559524Search in Google Scholar

Kiełbasiński P, Albrycht M, Łuczak J, Mikołajczyk M. Enzymatic reactions in ionic liquids: lipase-catalysed kinetic resolution of racemic, P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides. Tetrahedron-Asymmetr 2002; 13: 735–738.10.1016/S0957-4166(02)00167-2Search in Google Scholar

Kim YJ, Lee YM, Lee HM, Park OO. Processabilities and mechanical-properties of the biodegradable LDPE modified starch blends. Korean J Chem Eng 1994; 11: 172–177.10.1007/BF02697462Search in Google Scholar

Komoto I, Kobayashi S. Lewis acid catalysis in supercritical carbon dioxide: use of poly(ethylene glycol) derivatives and perfluoroalkylbenzenes as surfactant molecules which enable efficient catalysis in scCO₂. J Org Chem 2004; 69: 680–688.10.1021/jo0353177Search in Google Scholar PubMed

Kotlewska AJ, van Rantwijk F, Sheldon RA, Arends IWCE. Epoxidation and baeyer-villiger oxidation using hydrogen peroxide and a lipase dissolved in ionic liquids. Green Chem 2011; 13: 2154–2160.10.1039/c1gc15255fSearch in Google Scholar

Kumar A, Pawar SS. Catalyzing Henry reactions in chloroaluminate ionic liquids. J Mol Catal A-Chem 2005; 235: 244–248.10.1016/j.molcata.2005.04.010Search in Google Scholar

Kuo T-W, Tan C-S. Alkylation of toluene with propylene in supercritical carbon dioxide over chemical liquid deposition HZSM-5 pellets. Ind Eng Chem Res 2001; 40: 4724–4730.10.1021/ie0104868Search in Google Scholar

Lai JQ, Hu ZL, Wang PW, Yang Z. Enzymatic production of microalgal biodiesel in ionic liquid [Bmim][PF₆]. Fuel 2012; 95: 329–333.10.1016/j.fuel.2011.11.001Search in Google Scholar

Lau RM, van Rantwijk F, Seddon KR, Sheldon RA. Lipase-catalyzed reactions in ionic liquids. Org Lett 2000; 2: 4189–4191.10.1021/ol006732dSearch in Google Scholar PubMed

Lee AF, Bennett JA, Manayil JC, Wilson K. Heterogeneous catalysis for sustainable biodiesel production via esterification and transesterification. Chem Soc Rev 2014; 43: 7887–7916.10.1039/C4CS00189CSearch in Google Scholar

Leitner W. Reactions in supercritical carbon dioxide (scCO2). In: Knochel P, editor. Modern solvents in organic synthesis. Berlin: Springer Berlin Heidelberg Press, 1999: 107–132.10.1007/3-540-48664-X_5Search in Google Scholar

Leitner W. Supercritical carbon dioxide as a green reaction medium for catalysis. Acc Chem Res 2002; 35: 746–756.10.1021/ar010070qSearch in Google Scholar PubMed

Li CZ, Wang Q, Zhao ZK. Acid in ionic liquid: an efficient system for hydrolysis of lignocellulose. Green Chem 2008; 10: 177–182.10.1039/B711512ASearch in Google Scholar

Li KX, Chen L, Yan ZC, Wang HL. Application of pyridinium ionic liquid as a recyclable catalyst for acid-catalyzed transesterification of jatropha oil. Catal Lett 2010; 139: 151–156.10.1007/s10562-010-0409-xSearch in Google Scholar

Li LL, Feng W, Pan KH. Immobilization of lipase on amino-cyclodextrin functionalized carbon nanotubes for enzymatic catalysis at the ionic liquid-organic solvent interface. Colloids Surf B 2013; 102: 124–129.10.1016/j.colsurfb.2012.07.050Search in Google Scholar PubMed

Liang JH, Ren XQ, Wang JT, Li ZJ. Preparation of biodiesel by transesterification from cottonseed oil using the basic dication ionic liquids as catalysts. J Fuel Chem Technol 2010; 38: 275–280.10.1016/S1872-5813(10)60033-3Search in Google Scholar

Liu F, Abrams MB, Baker RT, Tumas W. Phase-separable catalysis using room temperature ionic liquids and supercritical carbon dioxide. Chem Commun 2001; 433–434.10.1039/b009701mSearch in Google Scholar

Liu ZC, Xu CM, Huang C. Method for manufacturing alkylate oil with composite ionic liquid used as catalyst. US Patent 7285698, 2003.Search in Google Scholar

Liu ZC, Zhang R, Xu CM, Xia RG. Ionic liquid alkylation process produces high-quality gasoline. Oil Gas J 2006; 104: 52–56.Search in Google Scholar

Liu ZC, Meng XH, Zhang R, Xu CM, Dong H, Hu YF. Reaction performance of isobutane alkylation catalyzed by a composite ionic liquid at a short contact time. AIChE J 2014; 60: 2244–2253.10.1002/aic.14394Search in Google Scholar

Loeker F, Leitner W. Steel-promoted oxidation of olefins in supercritical carbon dioxide using dioxygen in the presence of aldehydes. Chem Eur J 2000; 6: 2011–2015.10.1002/1521-3765(20000602)6:11<2011::AID-CHEM2011>3.0.CO;2-LSearch in Google Scholar

Long T, Deng YF, Gan SC, Chen J. Application of choline chloride·xZnCl₂ ionic liquids for preparation of biodiesel. Chin J Chem Eng 2010; 18: 322–327.10.1016/S1004-9541(08)60359-6Search in Google Scholar

Lozano P, De Diego T, Carrié D, Vaultier M, Iborra JL. Continuous green biocatalytic processes using ionic liquids and supercritical carbon dioxide. Chem Commun 2002; 692–693.10.1039/b200055eSearch in Google Scholar

Lozano P, De Diego T, Gmouh S, Vaultier M, Iborra JL. Criteria to design green enzymatic processes in ionic liquid/supercritical carbon dioxide systems. Biotechnol Progr 2004; 20: 661–669.10.1021/bp0342497Search in Google Scholar

Lozano P, De Diego T, Sauer T, Vaultier M, Gmouh S, Iborra JL. On the importance of the supporting Candida antarctica lipase B in material for activity of immobilized ionic liquid/hexane and ionic liquid/supercritical carbon dioxide biphasic media. J Supercrit Fluid 2007; 40: 93–100.10.1016/j.supflu.2006.03.025Search in Google Scholar

MacLeod S, Rosso RJ. Hydrogenation of low molecular weight polymers in ionic liquids and the effects of added salt. Adv Synth Catal 2003; 345: 568–571.10.1002/adsc.200202203Search in Google Scholar

Mathews CJ, Smith PJ, Welton T. Novel palladium imidazole catalysts for Suzuki cross-coupling reactions. J Mol Catal A-Chem 2003; 206: 77–82.10.1016/S1381-1169(03)00447-3Search in Google Scholar

Matsuda T, Harada T, Nakamura K. Organic synthesis using enzymes in supercritical carbon dioxide, Green Chem 2004a; 6: 440–444.10.1039/b404564pSearch in Google Scholar

Matsuda T, Watanabe K, Harada T, Nakamura K. Enzymatic reactions in supercritical CO₂: carboxylation, asymmetric reduction and esterification. Catal Today 2004b; 96: 103–111.10.1016/j.cattod.2004.06.111Search in Google Scholar

McHugh MA, Krukonis V. Supercritical fluids extraction: principles and practice. Stoneham, MA: Butterworth-Heinemann, 1994.10.1016/B978-0-08-051817-6.50014-XSearch in Google Scholar

Mikami K, editor. Green reaction media in organic synthesis. Oxford: Blackwell, 2005.10.1002/9780470988770Search in Google Scholar

Mjalli FS, Ahmed OU, Al-Wahaibi T, Al-Wahaibi Y, AlNashef IM. Deep oxidative desulfurization of liquid fuels. Rev Chem Eng 2014; 30: 337–378.10.1515/revce-2014-0001Search in Google Scholar

Mochizuki Y, Sugawara K. Removal of organic sulfur from hydrocarbon resources using ionic liquids. Energ Fuel 2008; 22: 3303–3307.10.1021/ef800400kSearch in Google Scholar

Mohile SS, Potdar MK, Salunkhe MM. An alternative route to syntheses of aryl keto acids in a chloroaluminate ionic liquid. J Chem Res 2003; 2003: 650–651.10.3184/030823403322655969Search in Google Scholar

Mori T, Okahata Y. Effective biocatalytic transgalactosylation in a supercritical fluid using a lipid-coated enzyme. Chem Commun 1998; 20: 2215–2216.10.1039/a806168hSearch in Google Scholar

Morita DK, Pesiri DR, David SA, Glaze WH, Tumas W. Palladium-catalyzed cross-coupling reactions in supercritical carbon dioxide. Chem Commun 1998; 1397–1398.10.1039/a802621aSearch in Google Scholar

Nagesha GK, Manohar B, Sankar KU. Enzymatic esterification of free fatty acids of hydrolyzed soy deodorizer distillate in supercritical carbon dioxide. J Supercrit Fluid 2004; 32: 137–145.10.1016/j.supflu.2004.02.001Search in Google Scholar

Naik PU, Nara SJ, Harjani JR, Salunkhe MM. An ionic liquid mediated friedel-crafts addition of arenes to isothiocyanates. Can J Chem 2003; 81: 1057–1060.10.1139/v03-152Search in Google Scholar

Nara SJ, Harjani JR, Salunkhe MM. Lipase-catalysed transesterification in ionic liquids and organic solvents: a comparative study. Tetrahedron Lett 2002; 43: 2979–2982.10.1016/S0040-4039(02)00420-3Search in Google Scholar

Neto BAD, Alves MB, Lapis AA, Nachtigall FM, Eberlin MN, Dupont J, Suarez PA. 1-N-butyl-3-methylimidazolium tetrachloro-Indate (BMI·InCl₄) as a media for the synthesis of biodiesel from vegetable oils. J Catal 2007; 249: 154–161.10.1016/j.jcat.2007.04.015Search in Google Scholar

Ngo HL, Hu AG, Lin WB. Highly enantioselective catalytic asymmetric hydrogenation of β-keto esters in room temperature ionic liquids. Chem Commun (Camb) 2003; 1912–1913.10.1039/B302637JSearch in Google Scholar PubMed

Ngo HL, Hu AG, Lin WB. Catalytic asymmetric hydrogenation of aromatic ketones in room temperature ionic liquids. Tetrahedron Lett 2005; 46: 595–597.10.1016/j.tetlet.2004.11.150Search in Google Scholar

Nolen SA, Lu J, Brown JS, Pollet P, Eason BC, Griffith KN, Gläser R, Bush D, Lamb DR, Liotta CL, Eckert CA. Olefin epoxidations using supercritical carbon dioxide and hydrogen peroxide without added metallic catalysts or peroxy acids. Ind Eng Chem Res 2002; 41: 316–323.10.1021/ie0100378Search in Google Scholar

Olivier-Bourbigou H, Magna L, Morvan D. Ionic liquids and catalysis: recent progress from knowledge to applications. Appl Catal A-Gen 2010; 373: 1–56.10.1016/j.apcata.2009.10.008Search in Google Scholar

Pârvulescu VI, Hardacre C. Catalysis in ionic liquids. Chem Rev 2007; 107: 2615–2665.10.1021/cr050948hSearch in Google Scholar PubMed

Pasta P, Mazzola G, Carrea G, Riva S. Subtilisin-catalyzed trans-esterification in supercritical carbon-dioxide. Biotechnol Lett 1989; 11: 643–648.10.1007/BF01025275Search in Google Scholar

Planeta J, Karasek P, Roth M. Distribution of sulfur-containing aromatics between [Hmim][Tf₂N] and supercritical CO₂: a case study for deep desulfurization of oil refinery streams by extraction with ionic liquids. Green Chem 2006; 8: 70–77.10.1039/B511778JSearch in Google Scholar

Plechkova NV, Seddon KR. Applications of ionic liquids in the chemical industry. Chem Soc Rev 2008; 37: 123–150.10.1039/B006677JSearch in Google Scholar

Pöhlmann F, Schilder L, Korth W, Jess A. Liquid phase isobutane/2-butene alkylation promoted by hydrogen chloride using Lewis acidic ionic liquids. Chempluschem 2013; 78: 570–577.10.1002/cplu.201300035Search in Google Scholar

Qureshi ZS, Deshmukh KM, Bhanage BM. Application of ionic liquids in organic synthesis and catalysis. Clean Tech Environ Policy 2014; 16: 1487–1513.10.1007/s10098-013-0660-0Search in Google Scholar

Reetz MT, Wiesenhöfer W, Franciò G, Leitner W. Biocatalysis in ionic liquids: batchwise and continuous flow processes using supercritical carbon dioxide as the mobile phase. Chem Commun (Camb) 2002; 992–993.10.1039/b202322aSearch in Google Scholar PubMed

Rodríguez-Cabo B, Rédriguez H, Rodil E, Arce A, Soto A. Extractive and oxidative-extractive desulfurization of fuels with ionic liquids. Fuel 2014; 117: 882–889.10.1016/j.fuel.2013.10.012Search in Google Scholar

Rogers R, Seddon K, Volkov S. Green industrial applications of ionic liquids. Norwell, MA: Kluwer Academic, 2003.10.1007/978-94-010-0127-4Search in Google Scholar

Rong MZ, Wang J, Shen YP, Han JY. Catalytic oxidation of alcohols by a novel manganese Schiff base ligand derived from salicylaldehyd and 1-phenylalanine in ionic liquids. Catal Commun 2012; 20: 51–53.10.1016/j.catcom.2011.11.035Search in Google Scholar

Sakthivel A, Nakamura R, Komura K, Sugi Y. Esterification of glycerol by lauric acid over aluminum and zirconium containing mesoporous molecular sieves in supercritical carbon dioxide medium. J Supercrit Fluid 2007; 42: 219–225.10.1016/j.supflu.2007.03.012Search in Google Scholar

Schofer SH, Kaftzik N, Wasserscheid P, Kragl U. Enzyme catalysis in ionic liquids: lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chem Commun 2001; 5: 425–426.10.1039/b009389kSearch in Google Scholar

Seddon KR, Stark A. Selective catalytic oxidation of benzyl alcohol and alkylbenzenes in ionic liquids. Green Chem 2002; 4: 119–123.10.1039/b111160bSearch in Google Scholar

Sellin MF, Cole-Hamilton DJ. Hydroformylation reactions in supercritical carbon dioxide using insoluble metal complexes. J Chem Soc Dalton Trans 2000; 1681–1683.10.1039/b001317jSearch in Google Scholar

Shezad N, Oakes RS, Clifford AA, Rayner CM. Use of fluorinated palladium sources for efficient Pd-catalysed coupling reactions in supercritical carbon dioxide. Tetrahedron Lett 1999; 40: 2221–2224.10.1016/S0040-4039(99)00176-8Search in Google Scholar

Shi CY, Zhao YL, Xin JY, Wang JQ, Lu XM, Zhang XP, Zhang SJ. Effects of cations and anions of ionic liquids on the production of 5-hydroxymethylfurfural from fructose. Chem Commun 2012; 48: 4103–4105.10.1039/c2cc30357dSearch in Google Scholar

Shiriyazdanov RR. Regeneration of zeolite-containing catalysts of alkylation of isobutane with the butane-butene faction in supercritical carbon dioxide. Russ J Phys Chem B 2011; 5: 1080–1083.10.1134/S1990793111070086Search in Google Scholar

Silveira ET, Umpierre AP, Rossi LM, Machado G, Morais J, Soares GV, Baumvol IJR, Teixeira SR, Fichtner PFP, Dupont J. The partial hydrogenation of benzene to cyclohexene by nanoscale ruthenium catalysts in imidazolium ionic liquids. Chem Eur J 2004; 10: 3734–3740.10.1002/chem.200305765Search in Google Scholar

Singhvi MS, Adsul MG, Gokhale DV. Comparative production of cellulases by mutants of Penicillium janthinellum NCIM 1171 and its application in hydrolysis of avicel and cellulose. Bioresour Technol 2011; 102: 6569–6572.10.1016/j.biortech.2011.01.014Search in Google Scholar

Sovová H, Stateva RP. Supercritical fluid extraction from vegetable materials. Rev Chem Eng 2011; 27: 79–156.10.1515/REVCE.2011.002Search in Google Scholar

Srivastava S, Madras G, Modak J. Esterification of myristic acid in supercritical carbon dioxide. J Supercrit Fluid 2003; 27: 55–64.10.1016/S0896-8446(02)00191-2Search in Google Scholar

Su WK, Wu CL, Su H. Ytterbium(III) trifluoromethanesulfonate catalysed friedel-crafts acylation of 1-methylpyrrole in ionic liquid. J Chem Res 2005; 2005: 67–68.10.3184/0308234053431130Search in Google Scholar

Suarez PAZ, Dullius JEL, Einloft S, De Souza RF, Dupont J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes. Polyhedron 1996; 15: 1217–1219.10.1016/0277-5387(95)00365-7Search in Google Scholar

Suarez PAZ, Dullius JEL, Einloft S, de Souza RF, Dupont J. Two-phase catalytic hydrogenation of olefins by Ru(Ii) and Co(Ii) complexes dissolved in 1-N-butyl-3-methylimidazolium tetrafluoroborate ionic liquid. Inorg Chim Acta 1997; 255: 207–209.10.1016/S0020-1693(96)05363-7Search in Google Scholar

Sun YK, Landau RN, Wang J, LeBlond C, Blackmond DG. A re-examination of pressure effects on enantioselectivity in asymmetric catalytic hydrogenation. J Am Chem Soc 1996; 118: 1348–1353.10.1021/ja952988gSearch in Google Scholar

Thompson DN, Ginosar DM, Coates K. Supercritical fluid regeneration of deactivated solid alkylation catalyst [abstract]. Am Chem Soc 2001; 222: U466.Search in Google Scholar

Tiltscher H, Hofmann H. Trends in high-pressure chemical-reaction engineering. Chem Eng Sci 1987; 42: 959–977.10.1016/0009-2509(87)80053-2Search in Google Scholar

Tominaga KI, Sasaki Y. Hydroformylation with carbon dioxide using ionic liquid media. Stud Surf Sci Catal 2004; 153: 227–232.10.1016/S0167-2991(04)80253-2Search in Google Scholar

Turner MB, Spear SK, Huddleston JG, Holbrey JD, Rogers RD. Ionic liquid salt-induced inactivation and unfolding of cellulase from Trichodermareesei. Green Chem 2003; 5: 443–447.10.1039/b302570eSearch in Google Scholar

Varma MN, Madras G. Synthesis of biodiesel from castor oil and linseed oil in supercritical fluids. Ind Eng Chem Res 2007; 46: 1–6.10.1021/ie0607043Search in Google Scholar

Vidya P, Chadha A. The role of different anions in ionic liquids on pseudomonas cepacia lipase catalyzed transesterification and hydrolysis. J Mol Catal B-Enzym 2009; 57: 145–148.10.1016/j.molcatb.2008.08.007Search in Google Scholar

Villarroya S, Zhou JX, Thurecht KJ, Howdle SM. Synthesis of graft copolymers by the combination of ATRP and enzymatic ROP in scCO₂. Macromol 2006; 39: 9080–9086.10.1021/ma061068nSearch in Google Scholar

Wang ZY, Jiang HF, Qi CR, Wang YG, Dong YS, Liu HL. PS-BQ: an efficient polymer-supported cocatalyst for the Wacker reaction in supercritical carbon dioxide. Green Chem 2005; 7: 582–585.10.1039/b505515fSearch in Google Scholar

Wang RH, Twamley B, Shreeve JM. A highly Efficient, recyclable catalyst for C-C coupling reactions in ionic liquids: pyrazolyl-functionalized N-heterocyclic carbene complex of palladium(II). J Org Chem 2006; 71: 426–429.10.1021/jo052098bSearch in Google Scholar PubMed

Wang JB, Qin RX, Fu HY, Chen J, Feng J, Chen H, Lia XJ. Asymmetric hydrogenation of α,β-unsaturated ketones catalyzed by Ru-TPPTS-(S,S)-DPENDS complex in ionic liquids. Tetrahedron-Asymmetr 2007a; 18: 847–851.10.1016/j.tetasy.2007.03.021Search in Google Scholar

Wang JQ, Cai F, Wang E, He LN. Supercritical carbon dioxide and poly(ethylene glycol): an environmentally benign biphasic solvent system for aerobic oxidation of styrene. Green Chem 2007b; 9: 882–887.10.1039/b701875dSearch in Google Scholar

Wei M, Musie GT, Busch DH, Subramaniam B. CO₂-expanded solvents: unique and versatile media for performing homogeneous catalytic oxidations. J Am Chem Soc 2002; 124: 2513–2517.10.1021/ja0114411Search in Google Scholar PubMed

Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev 1999; 99: 2071–2083.10.1021/cr980032tSearch in Google Scholar PubMed

Williams DBG, Ajam M, Ranwell A. Highly selective metathesis of 1-octene in ionic liquids. Organometallics 2006; 25: 3088–3090.10.1021/om051089qSearch in Google Scholar

Wimmer Z, Zarevúcka M. A review on the effects of supercritical carbon dioxide on enzyme activity. Int J Mol Sci 2010; 11: 233–253.10.3390/ijms11010233Search in Google Scholar PubMed PubMed Central

Wu ZW, Li Z, Wu GM, Wang LL, Lu SQ, Wang L, Wan H, Guan GF. Brønsted acidic ionic liquid modified magnetic nanoparticle: an efficient and green catalyst for biodiesel production. Ind Eng Chem Res 2014; 53: 3040–3046.10.1021/ie4040016Search in Google Scholar

Xie XF, Liotta CL, Eckert CA. CO₂-protected amine formation from nitrile and imine hydrogenation in gas-expanded liquids. Ind Eng Chem Res 2004; 43: 7907–7911.10.1021/ie0498201Search in Google Scholar

Xie WL, Hu LB, Yang XL. Basic ionic liquid supported on mesoporous SBA-15 silica as an efficient heterogeneous catalyst for biodiesel production. Ind Eng Chem Res 2015; 54: 1505–1512.10.1021/ie5045007Search in Google Scholar

Xin JY, Zhang SJ, Yan DX, Ayodele O, Lu XM, Wang JJ. Formation of C-C bonds for the production of bio-alkanes under mild conditions. Green Chem 2014; 16: 3589–3595.10.1039/C4GC00501ESearch in Google Scholar

Xin JY, Yan DX, Ayodele O, Zhang Z, Lu XM, Zhang SJ. Conversion of biomass derived valerolactone into high octane number gasoline with an ionic liquid. Green Chem 2015; 17: 1065–1070.10.1039/C4GC01792GSearch in Google Scholar

Xing XQ, Zhao GY, Cui JZ, Zhang SJ. Isobutane alkylation using acidic ionic liquid catalysts. Catal Commun 2012; 26: 68–71.10.1016/j.catcom.2012.04.022Search in Google Scholar

Xiong W, Lin Q, Ma H, Zheng H, Chen H, Li X. Asymmetric hydrogenation of aromatic ketones in ionic-liquid media catalyzed by Ru-TPPTS-(1S,2S)-DPENDS complexes. Tetrahedron-Asymmetr 2005; 16: 1959–1962.10.1016/j.tetasy.2005.03.037Search in Google Scholar

Xu Y, Wang Y, Zeng Y, Jiang J, Jin Z. A novel thermoregulated ionic liquid and organic biphasic system with Rh nanoparticles for olefin hydroformylation. Catal Lett 2012; 142: 914–919.10.1007/s10562-012-0841-1Search in Google Scholar

Yadav JS, Subba RBV, Shubashree S, Sadashiv K, Naidu JJ. Ionic liquids-promoted multi-component reaction: green approach for highly substituted 2-aminofuran derivatives. Synthesis-Stuttgart 2004a; 2376–2380.10.1055/s-2004-831181Search in Google Scholar

Yadav JS, Reddy BVS, Eeshwaraiah B, Gupta MK. Bi(OTf)₃/[Bmim]BF₄ as novel and reusable catalytic system for the synthesis of furan, pyrrole and thiophene derivatives. Tetrahedron Lett 2004b; 45: 5873–5876.10.1002/chin.200444118Search in Google Scholar

Yang Y, Fan H, Song J, Meng Q, Zhou H, Wu L, Yang G, Han B. Free radical reaction promoted by ionic liquid: a route for metal-free oxidation depolymerization of lignin model compound and lignin. Chem Commun 2015; 51: 4028–4031.10.1039/C4CC10394GSearch in Google Scholar

Yasmin T, Jiang T, Han BX, Zhang JC, Ma XM. Transesterification reaction catalysed by novozym 435 in supercritical carbon dioxide. J Mol Catal B-Enzym 2006; 41: 27–31.10.1016/j.molcatb.2006.04.001Search in Google Scholar

Yonker CR, Linehan JC. A high-pressure NMR investigation of reaction chemistries in a simple salt hydrate. J Supercrit Fluids 2004; 29: 257–263.10.1016/S0896-8446(03)00089-5Search in Google Scholar

Zeng Y, Wang Y, Xu Y, Song Y, Zhao J, Jiang J, Jin Z. Rh nanoparticles catalyzed hydroformylation of olefins in a thermoregulated ionic liquid/organic biphasic system. Chin J Catal 2012; 33: 402–406.10.1016/S1872-2067(11)60371-9Search in Google Scholar

Zhang JC, Wang HB, Liu HT, Cao WL. Hydroformylation of propylene in supercritical CO₂+H₂O and supercritical propylene+H₂O. J Mol Catal A-Chem 2006; 260: 95–99.10.1016/j.molcata.2006.07.001Search in Google Scholar

Zhang L, Xian M, He YC, Li LZ, Yang JM, Yu ST, Xu X. A Brønsted acidic ionic liquid as an efficient and environmentally benign catalyst for biodiesel synthesis from free fatty acids and alcohols. Bioresour Technol 2009a; 100: 4368–4373.10.1016/j.biortech.2009.04.012Search in Google Scholar PubMed

Zhang SJ, Xu CM, Lu XM, Zhou Q. Ionic liquid and green chemistry. China: Science Press, 2009b: 294–325.Search in Google Scholar

Zhang KP, Lai JQ, Huang ZL, Yang Z. Penicillium expansum lipase-catalyzed production of biodiesel in ionic liquids. Bioresour Technol 2011; 102: 2767–2772.10.1016/j.biortech.2010.11.057Search in Google Scholar PubMed

Zhang SJ, Sun J, Zhang XC, Xin JY, Miao QQ, Wang JJ. Ionic liquid-based green processes for energy production. Chem Soc Rev 2014; 43: 7838–7869.10.1039/C3CS60409HSearch in Google Scholar PubMed

Zhao HB, Holladay JE, Brown H, Zhang ZC. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 2007; 316: 1597–1600.10.1126/science.1141199Search in Google Scholar PubMed

Zhao H, Jones CL, Cowins JV. Lipase dissolution and stabilization in ether-functionalized ionic liquids. Green Chem 2009; 11: 1128–1138.10.1039/b905388cSearch in Google Scholar

Zhao YF, Yu B, Yang ZZ, Zhang HY, Hao LD, Gao X, Liu ZM. A protic ionic liquid catalyzes CO₂ conversion at atmospheric pressure and room temperature: synthesis of quinazoline-2,4(1H,3H)-diones. Angew Chem Int Ed 2014; 53: 5922–5925.10.1002/anie.201400521Search in Google Scholar PubMed

Zhen B, Li HS, Jiao QZ, Li Y, Wu Q, Zhang YP. SiW₁₂O₄₀-based ionic liquid catalysts: catalytic esterification of oleic acid for biodiesel production. Ind Eng Chem Res 2012; 51: 10374–10380.10.1021/ie301453cSearch in Google Scholar