Ionic liquids as an enabling tool to integrate reaction and separation processes

Green Chemistry - Tập 21 Số 24 - Trang 6527-6544
Rocío Villa1,2,3,4, Elena Álvarez1,2,3,4, Raúl Porcar5,6,7,3,8, Eduardo García‐Verdugo5,6,7,3,8, Santiago V. Luis5,6,7,3,8, Pedro Lozano1,2,3,4
1Departamento de Bioquímica y Biología Molecular “B” e Inmunología. Facultad de Química. Campus de Excelencia Internacional Mare Nostrum
2Murcia
3Spain
4Universidad de Murcia
5Campus del Riu Sec
6Castellón
7Departamento de Química Inorgánica y Orgánica
8Universidad Jaume I

Tóm tắt

This tutorial review highlights representative examples of ionic liquid (IL)-based (bio)catalytic systems integrating reaction and separation, as a tool for the development of sustainable chemical processes (e.g.IL/scCO2biphasic reactors, membrane reactors, nanodrop systems, microfluidic devices, supported IL phases, sponge-like ILs,etc.).

Từ khóa


Tài liệu tham khảo

P. T. Anastas and J. C.Warner , Green Chemistry: Theory and Practice , Oxford University Press , New York , 1998

Anastas, 2003, Environ. Sci. Technol., 37, 94A, 10.1021/es032373g

Erythropel, 2018, Green Chem., 20, 1929, 10.1039/C8GC00482J

Scholten, 2012, ACS Catal., 2, 184, 10.1021/cs200525e

Dhakshinamoorthy, 2018, Green Chem., 20, 86, 10.1039/C7GC02260C

Sheldon, 2018, Chem. Rev., 118, 801, 10.1021/acs.chemrev.7b00203

be, 2015, Chem. Commun., 51, 17361, 10.1039/C5CC07600E

Anastas, 2019, Trends Chem., 1, 145, 10.1016/j.trechm.2019.03.007

Jimenez-Gonzalez, 2019, Curr. Opin. Green Sustainable Chem., 18, 66, 10.1016/j.cogsc.2019.02.004

Keim, 2003, Green Chem., 5, 105, 10.1039/b300138p

Constable, 2007, Green Chem., 9, 411, 10.1039/B703488C

Seyler, 2006, Ind. Eng. Chem. Res., 45, 7700, 10.1021/ie060525l

Clarke, 2018, Chem. Rev., 118, 747, 10.1021/acs.chemrev.7b00571

Lozano, 2010, Green Chem., 12, 555, 10.1039/b919088k

Li, 2012, Chem. Soc. Rev., 41, 1413, 10.1039/c1cs90064a

Sheldon, 2019, Curr. Opin. Green Sustainable Chem., 18, 13, 10.1016/j.cogsc.2018.11.006

Abou-Shehada, 2016, Chem. Eng. Process., 99, 88, 10.1016/j.cep.2015.07.005

Capello, 2007, Green Chem., 9, 927, 10.1039/b617536h

S. Mayadevi , in Industrial Catalysis and Separations: Innovations for Process Intensification , ed. K. V. Raghavan and B. M. Reddy , Apple Acad. Press Inc , Oakville , 2015 , pp. 219–246

Brunner, 2009, J. Supercrit. Fluids, 47, 373, 10.1016/j.supflu.2008.09.002

Slater, 2016, J. Environ. Sci. Health, Part A: Toxic/Hazard. Subst. Environ. Eng., 51, 487, 10.1080/10934529.2015.1128719

Alonso, 2013, Green Chem., 15, 584, 10.1039/c3gc37065h

Camp, 2018, ChemSusChem, 11, 3048, 10.1002/cssc.201801420

Pollet, 2014, Green Chem., 16, 1034, 10.1039/C3GC42302F

Hallett, 2011, Chem. Rev., 111, 3508, 10.1021/cr1003248

Dupont, 2002, Chem. Rev., 102, 3667, 10.1021/cr010338r

Welton, 2004, Coord. Chem. Rev., 248, 2459, 10.1016/j.ccr.2004.04.015

Chiappe, 2005, J. Phys. Org. Chem., 18, 275, 10.1002/poc.863

D. R. MacFarlane , M.Kar and J. M.Pringle , Fundamentals of Ionic Liquids: From Chemistry to Applications , Wiley-VCH, Verlag , Weinheim , 2017

Zhang, 2008, Environ. Sci. Technol., 42, 1724, 10.1021/es0713983

Cevasco, 2014, Green Chem., 16, 2375, 10.1039/c3gc42096e

Gonçalves, 2019, J. Cleaner Prod., 217, 844, 10.1016/j.jclepro.2019.01.133

de Maria, 2008, Angew. Chem., Int. Ed., 47, 6960, 10.1002/anie.200703305

Javed, 2018, J. Mol. Liq., 271, 403, 10.1016/j.molliq.2018.09.005

Ohno, 2019, Bull. Chem. Soc. Jpn., 92, 852, 10.1246/bcsj.20180401

Gomes, 2019, Chem. Soc. Rev., 48, 4317, 10.1039/C9CS00016J

P. Lozano , Sustainable Catalysis in Ionic Liquids , CRC Press , New York , 2018

Baker, 2004, Chem. Commun., 940, 10.1039/b401304m

De Diego, 2004, Biotechnol. Bioeng., 88, 916, 10.1002/bit.20330

De Diego, 2005, Biomacromolecules, 6, 1457, 10.1021/bm049259q

Zhou, 2018, RSC Adv., 8, 32832, 10.1039/C8RA06384B

Gubicza, 2003, Green Chem., 5, 236, 10.1039/b211342m

Yao, 2018, Chem. Eng. Sci., 189, 340, 10.1016/j.ces.2018.06.007

Blanchard, 1999, Nature, 399, 28, 10.1038/19887

Blanchard, 2001, J. Phys. Chem. B, 105, 2437, 10.1021/jp003309d

Lozano, 2010, Green Chem., 12, 1803, 10.1039/c0gc00076k

Garcia-Verdugo, 2015, Green Chem., 17, 2693, 10.1039/C4GC02388A

Lozano, 2015, Green Chem., 17, 3706, 10.1039/C5GC00894H

Altava, 2018, Chem. Soc. Rev., 47, 2722, 10.1039/C7CS00734E

Farmer, 2002, Green Chem., 4, 97, 10.1039/b109851a

Itoh, 2002, Chem. Lett., 154, 10.1246/cl.2002.154

Passos, 2016, Sci. Rep., 20276, 10.1038/srep20276

Silva, 2017, Chem. Commun., 53, 7298, 10.1039/C7CC02294H

Fukumoto, 2007, Angew. Chem., Int. Ed., 46, 1852, 10.1002/anie.200604402

Ferreira, 2018, Green Chem., 20, 1218, 10.1039/C7GC03880A

Pera-Titus, 2015, Angew. Chem., Int. Ed., 54, 2006, 10.1002/anie.201402069

Yang, 2017, Front. Pharmacol., 8, 287, 10.3389/fphar.2017.00287

Yang, 2015, J. Am. Chem. Soc., 137, 1362, 10.1021/ja512337z

Crossley, 2010, Science, 327, 68, 10.1126/science.1180769

Zapata, 2012, Top. Catal., 55, 38, 10.1007/s11244-012-9768-4

Faria, 2010, Adv. Synth. Catal., 352, 2359, 10.1002/adsc.201000479

Zhang, 2017, J. Am. Chem. Soc., 139, 17387, 10.1021/jacs.7b07731

Meng, 2019, Green Chem., 21, 627, 10.1039/C8GC03585G

Zhang, 2019, J. Am. Chem. Soc., 141, 5220, 10.1021/jacs.8b11860

Gao, 2006, Green Chem., 8, 43, 10.1039/B510902G

Zeng, 2015, Bioprocess Biosyst. Eng., 38, 939, 10.1007/s00449-014-1339-6

Keskin, 2007, J. Supercrit. Fluids, 43, 150, 10.1016/j.supflu.2007.05.013

Blanchard, 2001, J. Phys. Chem. B, 105, 2437, 10.1021/jp003309d

Liu, 2016, Rev. Chem. Eng., 32, 587, 10.1515/revce-2015-0078

Jutz, 2011, Chem. Rev., 111, 322, 10.1021/cr100194q

Szyling, 2018, ACS Sustainable Chem. Eng., 6, 10980, 10.1021/acssuschemeng.8b02388

Shi, 2016, ACS Sustainable Chem. Eng., 4, 557, 10.1021/acssuschemeng.5b00889

Hiraga, 2018, J. Supercrit. Fluids, 134, 12, 10.1016/j.supflu.2017.12.022

Peris, 2019, ChemSusChem, 12, 1684, 10.1002/cssc.201900107

Medina-Gonzalez, 2014, ACS Sustainable Chem. Eng., 2, 2623, 10.1021/sc5004314

J. Walkowiak , G.Francio and W.Leitner , in Applied Homogeneous Catalysis with Organometallic Compounds , ed. B. Cornils , W. A. Herrrmann , M. Beller and R. Paciello , Wiley-VCH Verlag , Weinheim , 3rd edn, 2017 , ch. 20, pp. 1221–1258

Leitner, 2002, Acc. Chem. Res., 35, 746, 10.1021/ar010070q

Van Doorslaer, 2010, Dalton Trans., 39, 8377, 10.1039/c001285h

R. Fehrmann , A.Riisager and M.Haumann , Supported Ionic Liquids: Fundamentals and Applications , Wiley-VCH Verlag , Weinheim , 2014

Zhang, 2017, Chem. Rev., 117, 6755, 10.1021/acs.chemrev.6b00509

Riisager, 2003, J. Catal., 219, 452, 10.1016/S0021-9517(03)00223-9

Riisager, 2003, Catal. Lett., 90, 149, 10.1023/B:CATL.0000004109.46005.be

Haumann, 2007, Adv. Synth. Catal., 349, 425, 10.1002/adsc.200600413

Marinkovic, 2019, Ind. Eng. Chem. Res., 58, 2409, 10.1021/acs.iecr.8b04010

Gelesky, 2007, Dalton Trans., 5549, 10.1039/b708111a

Ruta, 2007, J. Catal., 247, 269, 10.1016/j.jcat.2007.02.012

Brunig, 2018, ACS Catal., 8, 1048, 10.1021/acscatal.7b04149

Hintermair, 2010, ChemCatChem, 2, 150, 10.1002/cctc.200900261

Riisager, 2006, Chem. Commun., 994, 10.1039/b516314e

Werner, 2009, Phys. Chem. Chem. Phys., 11, 10817, 10.1039/b912688k

Kukawka, 2019, ACS Sustainable Chem. Eng., 7, 4699, 10.1021/acssuschemeng.8b04357

Francio, 2015, Philos. Trans. R. Soc., A, 373, 20150005, 10.1098/rsta.2015.0005

M. Haumann and P.Wasserscheid , in Applied Homogeneous Catalysis with Organometallic Compounds , ed. B. Cornils , W. A. Herrrmann , M. Beller and R. Paciello , Wiley-VCH Verlag , Weinheim , 3rd edn, 2017 , ch. 14, pp. 999–1068

Lozano, 2002, Chem. Commun., 692, 10.1039/b200055e

Reetz, 2002, Chem. Commun., 992, 10.1039/b202322a

Itoh, 2017, Chem. Rev., 117, 10567, 10.1021/acs.chemrev.7b00158

Lozano, 2009, Green Chem., 11, 538, 10.1039/b821623a

Abai, 2015, Dalton Trans., 44, 8617, 10.1039/C4DT03273J

https://corporate.evonik.com/en/Pages/article.aspx?articleId=106423

Xu, 2015, Green Chem., 17, 108, 10.1039/C4GC01754D

http://english.ipe.cas.cn/ic/ic/201905/t20190519_209890.html

Zhang, 2014, Adv. Mater., 26, 6810, 10.1002/adma.201305448

Qian, 2017, Chem. Soc. Rev., 46, 1124, 10.1039/C6CS00620E

Eftelchari, 2017, Eur. Polym. J., 90, 245, 10.1016/j.eurpolymj.2017.03.033

Campisciano, 2017, Chem. Rec., 17, 918, 10.1002/tcr.201700005

Xin, 2014, Chem. Soc. Rev., 43, 7171, 10.1039/C4CS00172A

Valkenberg, 2002, Green Chem., 4, 88, 10.1039/b107946h

Burguete, 2007, Chem. Commun., 3086, 10.1039/B704611A

Chiappe, 2011, J. Phys. Chem. B, 115, 9653, 10.1021/jp2045788

S. Montolio , B.Altava , E.Garcia-Verdugo and S. V.Luis , in Green Synthetic Processes and Procedures , ed. R. Ballini , RSC Green Chemistry Series , Cambridge , 2019 , ch. 13, pp. 289–318

Xu, 2018, Prog. Polym. Sci., 79, 121, 10.1016/j.progpolymsci.2017.11.005

Giacalone, 2016, ChemCatChem, 8, 664, 10.1002/cctc.201501086

Zhang, 2015, Chem. Sci., 6, 3684, 10.1039/C5SC01374G

Sans, 2011, Chem. – Eur. J., 17, 1894, 10.1002/chem.201001873

Castro-Grijalba, 2017, RSC Adv., 7, 42979, 10.1039/C7RA07947H

Garcia-Bernabe, 2016, Electrochim. Acta, 213, 887, 10.1016/j.electacta.2016.08.018

Altava, 2015, Polymer, 72, 69, 10.1016/j.polymer.2015.07.009

Gruttadauria, 2011, Adv. Synth. Catal., 353, 2119, 10.1002/adsc.201100186

Agrigento, 2014, Catal. Sci. Technol., 4, 1598, 10.1039/C3CY01000G

Martin, 2014, Green Chem., 16, 1639, 10.1039/c3gc42238k

Wang, 2017, RSC Adv., 7, 2836, 10.1039/C6RA26780G

Lozano, 2007, Adv. Synth. Catal., 349, 1077, 10.1002/adsc.200600554

Izquierdo, 2013, RSC Adv., 3, 13123, 10.1039/c3ra42467g

Lozano, 2012, ChemSusChem, 5, 790, 10.1002/cssc.201100692

Lozano, 2010, Green Chem., 12, 1803, 10.1039/c0gc00076k

Porcar, 2018, React. Chem. Eng., 3, 572, 10.1039/C8RE00097B

Peris, 2019, ChemCatChem, 7, 1955, 10.1002/cctc.201900086

Scholten, 2012, ACS Catal., 2, 184, 10.1021/cs200525e

Luska, 2015, Green Chem., 17, 3195, 10.1039/C5GC00231A

Mudhoo, 2018, Biochem. Eng. J., 138, 141, 10.1016/j.bej.2018.07.018

Chacon, 2019, ChemCatChem, 11, 333, 10.1002/cctc.201801363

Umpierre, 2005, Adv. Synth. Catal., 347, 1404, 10.1002/adsc.200404313

Fonseca, 2004, Synlett, 1525

He, 2015, Phys. Chem. Chem. Phys., 17, 18238, 10.1039/C5CP01620G

Burguete, 2011, Phys. Chem. Chem. Phys., 13, 14831, 10.1039/c1cp20970a

Restrepo, 2015, ACS Catal., 5, 4743, 10.1021/acscatal.5b01129

Restrepo, 2015, Catal. Today, 255, 97, 10.1016/j.cattod.2014.12.023

Dani, 2016, J. Phys. Chem. C, 120, 1683, 10.1021/acs.jpcc.5b11137

Burguete, 2010, J. Catal., 269, 150, 10.1016/j.jcat.2009.11.002

Karbass, 2006, Chem. Commun., 29, 3095, 10.1039/b603224a

Luska, 2016, ACS Sustainable Chem. Eng., 4, 6186, 10.1021/acssuschemeng.6b01779

Offner-Marko, 2018, Angew. Chem., Int. Ed., 57, 12721, 10.1002/anie.201806638

Sans, 2010, Adv. Synth. Catal., 352, 3013, 10.1002/adsc.201000528

Belafi-Bako, 2002, Desalination, 149, 267, 10.1016/S0011-9164(02)00781-6

Izak, 2018, ChemPlusChem, 83, 7, 10.1002/cplu.201700293

Yan, 2019, Sep. Purif. Technol., 222, 230, 10.1016/j.seppur.2019.03.103

Wang, 2016, Green Energy Environ., 1, 43, 10.1016/j.gee.2016.05.002

Rynkowska, 2018, Rev. Chem. Eng., 34, 341, 10.1515/revce-2016-0054

Kim, 2017, Energy Procedia, 114, 17, 10.1016/j.egypro.2017.03.1141

Bednar, 2016, Chem. Eng. J., 303, 621, 10.1016/j.cej.2016.05.148

Gu, 2015, J. Membr. Sci., 492, 331, 10.1016/j.memsci.2015.05.051

Zhang, 2019, J. Membr. Sci., 584, 268, 10.1016/j.memsci.2019.05.006

Li, 2018, Prog. Polym. Sci., 87, 1, 10.1016/j.progpolymsci.2018.06.009

Jiang, 2017, Ind. Eng. Chem. Res., 56, 11817, 10.1021/acs.iecr.7b03063

Cao, 2017, Sci. Rep., 7, 3101, 10.1038/s41598-017-03265-z

Montolio, 2017, J. Mater. Chem. A, 5, 9733, 10.1039/C7TA02447A

Porcar, 2018, Chem. Commun., 54, 2385, 10.1039/C8CC00371H

Shi, 2019, Chem. Eng. J., 361, 635, 10.1016/j.cej.2018.12.104

Elvira, 2013, Nat. Chem., 5, 905, 10.1038/nchem.1753

Yao, 2018, Chem. Eng. Sci., 189, 340, 10.1016/j.ces.2018.06.007

Suryawanshi, 2018, Chem. Eng. Sci., 189, 431, 10.1016/j.ces.2018.03.026

Kumar, 2012, Green Process. Synth., 79

Zhao, 2013, Green Chem., 15, 446, 10.1039/C2GC36612F

Rahman, 2006, Chem. Commun., 2236, 10.1039/b600970k

Wang, 2013, Bioresour. Technol., 149, 367, 10.1016/j.biortech.2013.09.098

Wang, 2016, J. Chem. Technol. Biotechnol., 91, 555, 10.1002/jctb.4703

Horii, 2007, J. Am. Chem. Soc., 129, 11692, 10.1021/ja075180s

Ryu, 2008, Synlett, 151, 10.1055/s-2007-1000884

Liu, 2004, Org. Process Res. Dev., 8, 447, 10.1021/op034200h

Bai, 2017, J. Flow Chem., 7, 52, 10.1556/1846.2017.00002

Kluson, 2017, Chem. Eng. Process., 115, 39, 10.1016/j.cep.2017.02.002

Kukawka, 2016, RSC Adv., 6, 61860, 10.1039/C6RA08278E

Jankowska-Wajda, 2018, New J. Chem., 42, 5229, 10.1039/C7NJ04396A

Keil, 2018, Rev. Chem. Eng., 34, 135, 10.1515/revce-2017-0085

Karande, 2016, Org. Process Res. Dev., 20, 361, 10.1021/acs.oprd.5b00352

Novak, 2013, Green Process. Synth., 2, 561, 10.1515/gps-2013-0082

Pohar, 2009, Lab Chip, 9, 3385, 10.1039/b915151f

Novak, 2012, Sep. Purif. Technol., 97, 172, 10.1016/j.seppur.2012.01.033

Gong, 2015, Bioresour. Technol., 193, 498, 10.1016/j.biortech.2015.06.143

Qiao, 2017, Chem. Rev., 117, 6881, 10.1021/acs.chemrev.6b00652

Lv, 2016, J. Mol. Catal. A: Chem., 415, 89, 10.1016/j.molcata.2016.01.015

Chen, 2013, Appl. Catal., B, 138, 161, 10.1016/j.apcatb.2013.02.028

Zhu, 2013, Chem. – Eur. J., 19, 2059, 10.1002/chem.201202707

Chen, 2014, Catal. Commun., 47, 18, 10.1016/j.catcom.2014.01.003

Mecerreyes, 2011, Prog. Polym. Sci., 36, 1629, 10.1016/j.progpolymsci.2011.05.007

Montolio, 2014, Chem. Commun., 50, 10683, 10.1039/C4CC03140G

Karjalainen, 2014, Polym. Chem., 5, 1437, 10.1039/C3PY01364B

Lozano, 2011, Fuel, 90, 3461, 10.1016/j.fuel.2011.06.008

Lozano, 2012, Green Chem., 14, 3026, 10.1039/c2gc36081k

Lozano, 2013, Energy Environ. Sci., 6, 1328, 10.1039/c3ee24429f

Bonhote, 1996, Inorg. Chem., 35, 1168, 10.1021/ic951325x

Lozano, 2014, Curr. Green Chem., 1, 145, 10.2174/2213346101666131113201434

Alvarez, 2019, ACS Sustainable Chem. Eng., 7, 13307, 10.1021/acssuschemeng.9b02537

Lozano, 2010, ChemSusChem, 3, 1359, 10.1002/cssc.201000244

Lozano, 2016, ACS Sustainable Chem. Eng., 4, 6125, 10.1021/acssuschemeng.6b01570

Lozano, 2019, Catal. Today, 10.1016/j.cattod.2019.01.073

Huang, 2019, Chem. Rev., 119, 4357, 10.1021/acs.chemrev.8b00672