Abstract
Ionic liquids (ILs) as reaction media, and sonochemistry (US) as activation method, represent separately unconventional approaches to reaction chemistry that, in many cases, generate improvements in yield, rate and selectivity compared to traditional chemistry, or even induce a change in the mechanisms or expected products. Recently, these two technologies have been combined in a range of different applications, demonstrating very significant and occasionally surprising synergetic effects. In this book chapter, the advantages and limitations of the IL/US combination in different chemical applications are critically reviewed in order to understand how, and in which respects, it could become an essential tool of sustainable chemistry in the future. Fundamental aspects and practical considerations of the combination are discussed to better control and demonstrate the brought synergetic effects.
Similar content being viewed by others
References
Rogers RD, Seddon KR (2003) Science 302:792–793
Rogers RD, Seddon KR (2003) Ionic liquids as green solvents: progress and prospects. American Chemical Society, Washington, D.C.
Wasserscheid P, Welton T (2008) Ionic liquids in synthesis. Wiley-VCH, Weinheim
Hallett JP, Welton T (2011) Chem Rev 111:3508–3576
Cojocaru OA, Bica K, Gurau G, Narita A, McCrary PD, Shamshina JL, Barber PS, Rogers RD (2013) MedChemComm 4:559–563
Zhang P, Wu T, Han B (2014) Adv Mater 26:6810–6827
Ho TD, Zhang C, Hantao LW, Anderson JL (2014) Anal Chem 86:262–285
MacFarlane DR, Tachikawa N, Forsyth M, Pringle JM, Howlett PC, Elliot GD, Davis JH Jr, Watanabe M, Simon P, Austen Angell C (2014) Energy Environ Sci 7:232–250
Torriero AAJ (2015) Electrochemistry in Ionic Liquids, Springer International Publishing, p 738
Stanisz E, Werner J, Zgoła-Grześkowiak A (2014) TrAC Trends Anal Chem 61:64–66
Tadesse H, Luque R (2011) Energy Environ Sci 4:3913–3929
Holbrey JD, Seddon KR (1999) Clean Products and Processes. In: Matsunaga T (ed.), Vol. 1, Springer-Verlag, New York, p 223
Chatel G, Pereira JFB, Debbeti V, Wang H, Rogers RD (2014) Green Chem 16:2051–2083
Stark A, Behrend P, Braun O, Müller A, Ranke J, Ondruschka B, Jastorff B (2008) Green Chem 10:1152–1161
Chatel G, MacFarlane DR (2014) Chem Soc Rev 43:8132–8149
Namboodiri VV, Varma RS (2002) Org Lett 4:3161–3163
Lévêque J-M, Luche J-L, Pétrier C, Roux R, Bonrath W (2002) Green Chem 4:357–360
Zhao S, Zhao E, Shen P, Zhao M, Sun J (2008) Ultrason Sonochem 15:955–959
Cravotto G, Boffa L, Lévêque JM, Estager J, Draye M, Bonrath W (2007) Aust J Chem 60:946–950
Li W, Lin Q, Ma L (2010) Ultrason Sonochem 17:752–755
Varma RS (2006) J Chem 45B:2305–2312
Lévêque JM, Desset S, Suptil J, Fachinger C, Draye M, Bonrath W, Cravotto G (2006) Ultrason Sonochem 13:189–193
Cravotto G, Gaudino EC, Boffa L, Lévêque JM, Estager J, Bonrath W (2008) Molecules 13:149–156
Messali M, Almtiri MN, Abderrahman B, Salghi R, Aouad MR, Alshahateet SF, Ali AAS (2015) S Afr J Chem 68:219–225
Messali M (2014) Arabian J Chem 7:63–70
Messali M, Asiri MAM (2013) J Mater Environ Sci 4:770–785
Messali M, Aouad MR, Ali AAS, Rezki N, Ben Hadda T (2015) Med Chem Res 24:1387–1395
Messali M (2015) Molecules 20:14936–14949
Ameta G, Kumar Pathak A, Ameta C, Ameta R, Punjabi PB (2015) J Mol Liq 211:934–937
Zbancioc G, Mangalagiu II, Moldoveanu C (2015) Ultrason Sonochem 23:376–384
Varma RS (2003) Expeditious synthesis of ionic liquids using ultrasound and microwave irradiation, In: Rogers R D and Seddon K R (eds.) Vol. 856, Ionic liquids as green solvents, ACS Symposium Series, American Chemical Society: Washington, Chap. 7, p 82–92
Varma RS (2007) Green Chem Lett Rev 1:37–45
Lévêque JM, Estager J, Draye M, Cravotto G, Boffa L, Bonrath W (2007) Monatsh Chem 138:1103–1113
Deetlefs M, Seddon KR (2010) Green Chem 12:17–30
Oxley JD, Prozorov T, Suslick KS (2003) J Am Chem Soc 125:11138–11139
Chatel G, Pflieger R, Naffrechoux E, Nikitenko SI, Suptil J, Goux-Henry C, Kardos N, Andrioletti B, Draye M (2013) ACS Sustainable Chem Eng 1:137–143
Deshmukh RR, Rajagopal R, Srinivasan KV (2001) Chem Commun p 1544–1545
Rajagopal R, Srinivasan KV (2003) Ultrason Sonochem 10:41–43
Rajagopal R, Jarikote DV, Srinivasan KV (2002) Chem Commun p 616–617
Gholap AR, Venkatesan K, Daniel T, Lahoti RJ, Srinivasan KV (2004) Green Chem 6:147–150
Gholap AR, Venkatesan K, Daniel T, Lahoti RJ, Srinivasan KV (2003) Green Chem 5:693–696
Venkatesan K, Pujari SS, Lahoti RJ, Srinivasan KV (2008) Ultrason Sonochem 15:548–553
Gholap AR, Venkatesan K, Pasricha R, Daniel T, Lahoti RJ, Srinivasan KV (2005) J Org Chem 70:4869–4872
Yang HM, Hung YH, Tu CY (2014) J Taiwan Inst Chem Eng 45:1421–1427
Hua Q, Dabin L, Chunxu L (2011) Ultrason Sonochem 18:1035–1037
Chatel G, Goux-Henry C, Kardos N, Suptil J, Andrioletti B, Draye M (2012) Ultrason Sonochem 19:390–394
Chatel G, Goux-Henry C, Mirabaud A, Rossi T, Kardos N, Andrioletti B, Draye M (2012) J Catal 291:127–132
Mamaghani M, Pourranjbar M, Nia RH (2014) J Sulfur Chem 1:1–6
Wang J, Zong Y, Fu R, Niu Y, Yue G, Quan Z, Wang X, Pan Y (2014) Ultrason Sonochem 21:29–34
Li D, Zang H, Wu C, Yu N (2013) Ultrason Sonochem 20:1144–1148
Suresh, Sandhu JS (2013) Org Med Chem Lett 3:2–8
Qian H, Wang Y, Liu D (2013) Ind Eng Chem Res 52:13272–13275
Estager J, Lévêque JM, Turgis R, Draye M (2007) Tetrahedron Lett 5:755–759
Yinghuai Z, Bahnmueller S, Hosmane NS, Maguirey JA (2003) Chem Lett 32:730–731
Yinghuai Z, Bahnmueller S, Chibun C, Carpenter K, Hosmane NS, Maguire JA (2003) Tetrahedron Lett 44:5473–5476
Yinghuai Z (2004) J Phys Chem Solids 65:349–353
Wang X, Fulvio PF, Baker GA, Veith GM, Unocic RR, Mahurin SM, Chib M, Dai S (2010) Chem Commun 46:4487–4489
Shi JJ, Zhu JJ (2011) Electrochim Acta 56:6008–6013
Wu Y, Hao X, Yang J, Tian F, Jiang M (2006) Mat Lett 60:2764–2766
Behboudnia M, Habibi-Yangjeh A, Jafari-Tarzanag Y, Khodayari A (2008) J Cryst Growth 310:4544–4548
Goharshadi EK, Ding Y, Jorabchi MN, Nancarrow P (2009) Ultrason Sonochem 16:120–123
Barzegar M, Habibi-Yangjeh A, Behboudnia M (2009) J Phys Chem Solids 70:1353–1358
Salinas-Estevané P, Sanchez EM (2010) Mater Lett 64:2627–2630
Salinas-Estevané P, Sanchez EM (2010) Cryst Growth Des 10:3917–3924
Garcia-Gomez NA, De la Parra-Arcieniega SM, Garza-Tovar LL, Torres-Gonzalez LC, Sanchez EM (2014) J Alloys Compd 588:638–643
Taghvaei V, Habibi-Yangjeh A, Behboudnia M (2009) Powder Technol 195:63–67
Behboudnia M, Habibi-Yangjeh A, Jafari-Tarzanag Y, Khodayari A (2009) J Optoelectron Adv Mater 11:134–139
Behboudnia M, Habibi-Yangjeh A, Jafari-Tarzanag Y, Khodayari A (2008) Bull Korean Chem Soc 29:53–56
Behboudnia M, Habibi-Yangjeh A, Jafari-Tarzanag Y, Khodayari A (2010) J Phys Chem Solids 71:1393–1397
Alammar T, Birkner A, Shekhah O, Mudring AV (2010) Mater Chem Phys 120:109–113
Sang Shin U, Hong HK, Kim HW, Gong MS (2011) Bull Korean Chem Soc 32:1583–1586
Zhang S, Zhang Y, Wang Y, Liu S, Deng Y (2012) Phys Chem Chem Phys 14:5132–5138
McCrary PD, Beasley PA, Cojocaru OA, Schneider S, Hawkins TW, Perez JPL, McMahon BW, Pfeil M, Boatz JA, Anderson SL, Son SF, Rogers RD (2012) Chem Commun 48:4311–4313
Qian H, Ye ZW, Lv CX (2007) Lett Org Chem 4:482–485
Putz AM, Len A, Ianăşi C, Savii C, Almásy L (2016) Korean J Chem Eng 33:749–754
Yang C, Li F, Li T (2015) CrystEngComm 17:7676–7683
Zhu CZ, Guo SJ, Zhai ZY, Dong SJ (2010) Langmuir 26:7614–7618
Nalajala VS, Moholkar VS (2011) Ultrason Sonochem 18:345–355
Xiao W, Sun Z, Chen S, Zhang H, Zhao Y, Huang C, Liu Z (2012) RSC Adv 2:8189–8193
Mao BH, Liu CH, Gao X, Chang R, Liu Z, Wang SD (2013) Appl Surf Sci 283:1076–1079
Luska KL, Moores A (2012) Green Chem 14:1736–1742
Luska KL, Moores A (2012) ChemCatChem 4:1534–1546
Luska KL, Moores A (2011) Adv Synth Catal 353:3167–3177
Wittmar A, Ruiz-Abad D, Ulbricht M (2012) J Nanopart Res 14:651–661
Shafi KVPM, Ulman A, Dyal A, Yan X, Yang NL, Estournès C, Fournès L, Wattiaux A, White H, Rafailovich M (2002) Chem Mater 14:1778–1787
Bazureau JP, Draye M (2011) Ultrasound and Microwaves: Recent Advances in Organic Chemistry, Research Signpost
Suslick KS, Hammerton DA, Cline DE (1986) J Am Chem Soc 108:5641–5645
Jin Y, Wang P, Yin D, Liu J, Qin L, Yu N, Xie G, Li B (2007) Colloids Surf A 302:366–370
Kim KS, Demberelnyamba D, Lee H (2004) Langmuir 20:556–560
Yang C, Li F, Li T (2015) CrystEngComm 17:7676–7683
Poole CF, Poole SK (2010) J Chromatogr A 1217:2268–2286
Huddleston JG, Willauer HD, Swatloski RP, Visser AE, Rogers RD (1998) Chem Commun p 1765–1766
Sun X, Luo H, Dai S (2012) Chem Rev 112:2100–2128
Tan ZJ, Wang CY, Yang ZZ, Yi YJ, Wang HY, Zhou WL, Li FF (2015) Molecules 20:17929–17943
Liao J, Qu B, Liu D, Zheng N (2015) Ultrason Sonochem 27:110–116
Li C, Fu X, Huang Q, Luo F, You L (2015) Eur Food Res Technol 240:49–60
Cao X, Ye X, Lu Y, Yu Y, Mo W (2009) Anal Chim Acta 640:47–51
Zhou Q, Zhang X, Xiao J (2009) J Chromatogr A 1216:4361–4365
Abolhasani J, Amjadi M, Hassanzadeh J, Ghorbani-Kalhor E (2014) Anal Lett 47:1528–1540
He SW, Shen CY, Wei XQ, Jin MC, Cai MQ (2013) Adv Mater Res 726–731:74–80
Shamsipur M, Yazdanfar N, Ghambarian M (2016) Food Chem 204:289–297
Han D, Row KH (2011) J Sci Food Agric 91:2888–2892
Wu K, Zhang Q, Liu Q, Tang F, Long Y, Yao S (2009) J Sep Sci 32:4220–4226
Dong S, Hu Q, Yang Z, Liu R, Huang G, Huang T (2013) Microchem J 110:221–226
Gong A, Zhu X (2015) Talanta 131:603–608
Qin H, Zhou G, Peng G, Li J, Chen J (2015) Food Anal Methods 8:1673–1681
Sun Y, Li W, Wang J (2008) J Chromatogr B 879:975–980
Molaakbari E, Mostafavi A, Afzali D (2011) J Hazard Mater 185:647–652
Stanisz E, Werner J, Matusiewicz H (2013) Microchem J 110:28–35
Tuzen M, Pekiner OZ (2015) Food Chem 188:619–624
Parrilla Vazquez MM, Parrilla Vazquez P, Martinez Galera M, Garcia MDG, Ucles A (2013) J Chromatograph A 1291:19–21
Asensio-Ramos M, Hernandez-Borges J, Borges-Miquel TM, Rodriguez-Delgado MA (2011) J Chromatogr A 1218:4808–4816
Villagran C, Banks CE, Pitner WR, Hardacre C, Compton RG (2005) Ultrason Sonochem 12:423–428
Fuchigami T, Sunaga T, Ishii H, Atobe M (2002) In: Workentin M S, Maran F and Chiba K (eds.) Organic Electrochemistry, The electrochemical society: Pennington
Fuchigami T, Tajima T (2005) J Fluorine Chem 126:181–187
Feroci M, Orsini M, Inesi A (2009) Adv Synth Catal 35:2067–2070
Costa C, Doche ML, Hihn JY, Bisel I, Moisy P, Lévêque JM (2010) Ultrasonics 50:323–328
Compton RG, Hardcastle JL, Del Campo J (2003) In: Encyclopedia of electrochemistry (Ed. Bard Stratmann), Instrumentation and Electroanalytical Chemistry (Ed. P. Unwin), Vol. 3, Wiley-VCH, Weinheim
Xiao F, Mo Z, Zhao F, Zeng B (2008) Electrochem Commun 1:1740–1743
Xiao F, Zhao F, Mei D, Mo Z, Zeng B (2009) Biosens Bioelectron 24:3481–3486
Xiao F, Zhao F, Zhang Y, Guo G, Zeng B (2009) J Phys Chem C 113:849–855
Zhao F, Xiao F, Zeng B (2010) Electrochem Commun 12:168–171
He Y, Zheng J, Dong S (2012) Analyst 2012(137):4841–4848
He Y, Zheng J (2013) Anal Methods 5:767–772
Chatel G, De Oliveira Vigier K, Jérôme F (2014) ChemSusChem 7:2774–2787
Sun N, Rodriguez H, Rahman M, Rogers RD (2011) Chem Commun 47:1405–1421
Garcia A, Gonzalez Alriols M, Llano-Ponte R, Labidi J (2011) Bioresour Technol 102:6326–6330
Gogate PR, Abhijeet MK, Kabadi M (2009) Biochem Eng J 44:60–72
Rokhina EV, Lens P, Virkutyte J (2009) Trends Biotechnol 5:298–306
Mikkola JP, Kirilin A, Tuuf JC, Pranovich A, Holmbom B, Kustov LM, Murzin DY, Salmi T (2007) Green Chem 9:1229–1237
Sun N, Rahman M, Qin Y, Maxim ML, Rodriguez H, Rogers RD (2009) Green Chem 11:646–655
Maxim ML, Sun N, Wang H, Sterner JR, Haque A, Rogers RD (2012) Nanomater Energy 1:225–236
Cheng F, Wang H, Chatel G, Gurau G, Rogers RD (2014) Bioresour Technol 164:394–401
Ninomiya K, Kohori A, Tatsumi M, Osawa K, Endo T, Kakuchi R, Ogino C, Shimizu N, Takahashi K (2015) Bioresour Technol 176:169–174
Lan W, Liu C, Yue FX, Sun RC, Kennedy JF (2011) Carbohydr Polym 86:672–677
Liu L, Ju M, Li W, Hou Q (2013) Carbohydr Polym 98:412–420
Yang F, Li L, Li Q, Tan W, Liu W, Xian M (2010) Carbohydr Polym 81:311–316
Ho Ha S, Hiep NM, Koo YM (2010) Biotechnol Bioprocess Eng 15:126–130
Liu Z, Lu L (2011) Adv Mater Res 236–238:169–172
Lozano P, Bernal B, Recio I, Belleville MP (2012) Green Chem 14:2631–2637
Wang Y, Pan Y, Zhang Z, Sun R, Fang X, Yu D (2012) Process Biochem 47:976–982
Ninomiya K, Kamide K, Takahashi K, Shimizu N (2012) Bioresour Technol 103:259–265
Wang F, Chen ZG, Zhu HJ (2013) Biochem Eng J 79:25–28
Ninomiya K, Ohta A, Omote S, Ogino C, Takahashi K, Shimizu N (2013) Chem Eng J 215–216:811–818
Wang Y, Pan Y, Zhang Z, Sun R, Fang X, Yu D (2012) Process Biochem 47:976–982
Hernoux-Villière A, Lévêque JM, Kärkkäinen J, Papaiconomou N, Lajunen M, Lassi U (2014) Catal Today 223:11–17
Guo W, Li H, Ji G, Zhang G (2012) Bioresour Technol 125:332–334
Bi YG, Wu SS (2013) Adv Mat Res 791–793:196–199
Flannigan DJ, Hopkins SD, Suslick KS (2005) J Organomet Chem 690:3513–3517
Suslick KS, Hammerton DA, Cline RE (1986) J Am Chem Soc 108:5641–5642
Kanthale PM, Brotchie A, Grieser F, Ashokkumar M (2013) Ultrason Sonochem 20:47–51
Chatel G, Leclerc L, Naffrechoux E, Bas C, Kardos N, Goux-Henry C, Andrioletti B, Draye M (2012) J Chem Eng Data 57:3385–3390
Paulechka YU (2010) J Phys Chem Ref Data 39:033108
Rocha MAA, Coutinho JAP, Santos LMNBF (2014) J Chem Phys 141:134502
Stepnowski P, Zaleska A (2005) J Photochem Photobiol A 170:45–50
Jastorff B, Störmann R, Ranke J, Mölter M, Stock F, Oberheitmann B, Hoffman W, Hoffmann J, Nüchter M, Ondruschka B, Filser J (2003) Green Chem 5:136–142
Bubalo MC, Radosevic K, Redovnikovic IR, Halambek J, Srcek VG (2014) Ecotoxicol Environ Saf 99:1–12
Li X, Zhao J, Li Q, Wang L, Tsang SC (2007) Dalton Trans 1875–1880
Zhou H, Shen Y, Lv P, Wang J, Fan J (2013) Sep Purif Technol 104:208–213
Zhou H, Lv P, Shen Y, Wang J, Fan J (2013) Water Res 47:3514–3522
Lee SH, Nguyen HM, Koo YM, Koo SH, Ha SH (2008) Process Biochem 43:1009–1012
Wang J, Wang S, Li Z, Gua S, Wu X, Wu F (2015) J Mol Catal B Enzym 111:21–28
Li C, Lu Z, Zhao C, Yang L, Fu Y, Shi K, He X, Li Z, Zu Y (2015) J Sep Sci 38:291–300
Bubalo MC, Sabotin I, Radoš I, Valentinčič J, osiljkov T, Brnčić M (2013) Green Process Synth 2:579–590
Lévêque JM, Cravotto G (2006) CHIMIA Int J Chem 60:313–320
Author information
Authors and Affiliations
Corresponding author
Additional information
This article is part of the Topical Collection “Sonochemistry: From basic principles to innovative applications”; edited by Juan Carlos Colmenares Q., Gregory Chatel.
Rights and permissions
About this article
Cite this article
Chatel, G. Ultrasound in Combination with Ionic Liquids: Studied Applications and Perspectives. Top Curr Chem (Z) 374, 51 (2016). https://doi.org/10.1007/s41061-016-0055-x
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s41061-016-0055-x