Abstract
Taking into account the current issues of global warming and climate change resulting from the massive chemical wastes that go to the environment, the need of the hour is development of sustainable chemical processes. One of the major wastes that go to the environment from industries is solvents that are non-recyclable. This chapter focuses on ionic liquids as a greener alternate to the organic solvents in the synthesis of organic compounds. The chapter also highlights some reactions that have been reported as greener as they have adopted ionic liquids in the reaction media and catalysis. Industries have already started applying ionic liquids in different reactions, but the environment certainly needs more to be done.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Aggarwal A, Lancaster NL, Sethi AR, Welton T. The role of hydrogen bonding in controlling the selectivity of Diels–Alder reactions in room-temperature ionic liquids. Green Chem. 2002;4:517–20. https://doi.org/10.1039/B206472C.
Anastas P, Eghbali N. Green chemistry:principle and practice. Chem Soc Rev. 2010;39:301–12. https://doi.org/10.1039/B918763B.
Beckman EJ. Supercritical and near-critical CO2 in green chemical synthesis and processing. J Supercrit Fluids. 2004;28(2–3):121–91. https://doi.org/10.1016/S0896-8446(03)00029-9.
Bellina F, Chiappe C. The Heck reaction in ionic liquids: progress and challenges. Molecules. 2010;15(4):2211–45. https://doi.org/10.3390/molecules15042211.
Breno KL, Ahmed TJ, Pluth MD, Balzarek C, Tyler DR. Organometallic chemistry in aqueous solution: reactions catalyzed by water-soluble molybdocenes. Coord Chem Rev. 2006;250(9–10):1141–51. https://doi.org/10.1016/j.ccr.2005.12.001.
Casalnuovo AL, Calabrese JC. Palladium-catalyzed alkylations in aqueous media. J Am Chem Soc. 1990;112(11):4324–30. https://doi.org/10.1021/ja00167a032.
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 Engl. 1996;34(23–24):2698–700. https://doi.org/10.1002/anie.199526981.
Contesini FJ, Carvalho PDO. Esterification of (RS)-ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids. Tetrahedron Asymmetry. 2006;17(14):2069–73. https://doi.org/10.1016/j.tetasy.2006.07.020.
Curzons AD, Constable DC, Cunningham VL. Solvent selection guide: a guide to the integration of environmental, health and safety criteria into the selection of solvents. Clean Prod Process. 1999;1:82–90.
Earle MJ, McCormac PB, Seddon KR. Diels–Alder reactions in ionic liquids. A safe recyclable alternative to lithium perchlorate–diethyl ether mixtures. Green Chem. 1999;1:23–5. https://doi.org/10.1039/A808052F.
Earle MJ, McCormac PB, Seddon KR. The first high yield green route to a pharmaceutical in a room temperature ionic liquid. Green Chem. 2000;2(6):261–2. https://doi.org/10.1039/B006612P.
Grieco PA, Brandes EB, McCann S, Clark JD. Water as a solvent for the Claisen rearrangement: practical implications for synthetic organic chemistry. Org Chem. 1989;54(25):5849–51. https://doi.org/10.1021/jo00286a010.
Handy ST, Zhang X. Organic synthesis in ionic liquids: the Stille coupling. Org Lett. 2001;3(2):233–6. https://doi.org/10.1021/ol0068849.
Hou Q, Zhen M, Li W, Liu L, Liu J, Zhang S, et al. Efficient catalytic conversion of glucose into 5-hydroxymethylfurfural by aluminum oxide in ionic liquid. Appl Catal B Environ. 2019;353:1–10. https://doi.org/10.1016/j.apcatb.2019.04.003.
Jaeger DA, Tucker CE. Diels-Alder reactions in ethylammonium nitrate, a low-melting fused salt. Tetrahedron Lett. 1989;30(14):1785–8. https://doi.org/10.1016/S0040-4039(00)99579-0.
Kaufmann DE, Nouroozian M, Henze H. Molten salts as an efficient medium for palladium catalyzed C-C coupling reactions. Synlett. 1996;11:1091–2. https://doi.org/10.1055/s-1996-5658.
Khatik GL, Kumar R, Chakraborti AK. Catalyst-free conjugated addition of thiols to α,β-unsaturated carbonyl compounds in water. Org Lett. 2006;8(11):2433–6. https://doi.org/10.1021/ol060846t.
Kim DW, Song CE, Chi CY. Significantly enhanced reactivities of the nucleophilic substitution reactions in ionic liquid. J Organomet Chem. 2003;68(11):4281–5. https://doi.org/10.1021/jo034109b.
Klijn JE, Engberts JBFN. Fast reactions “on water”. Nature. 2005;435:46–7. https://doi.org/10.1038/435746a.
Kolb HC, Finn MG, Sharpless KB. Click chemistry: diverse chemical function from a few good reactions. Angew Chem. 2001;40(11):2001–21.
Kumar V, Malhotra SV. Synthesis of nucleoside-based antiviral drugs in ionic liquids. Bioorg Med Chem Lett. 2008;18(20):640–2. https://doi.org/10.1016/j.bmcl.2008.08.090.
Kurata A, Kitamura Y, Irie S, Takemoto S, Akai Y, Hirota Y, et al. Enzymatic synthesis of caffeic acid phenethyl ester analogues in ionic liquid. J Biotechnol. 2010a;148(2–3):133–8. https://doi.org/10.1016/j.jbiotec.2010.05.007.
Li CJ, Trost BM. Green chemistry for chemical synthesis. PNAS. 2008;105(36):13197–202. https://doi.org/10.1073/pnas.0804348105.
Trost BM. The atom economy—a search for synthetic efficiency. Science. 1991;254(5037):1471–7. https://doi.org/10.1126/science.1962206.
Ritleng V, Sirlin C, Pfeffer M. Ru-, Rh-, and Pd-catalyzed C−C bond formation involving C−H activation and addition on unsaturated substrates: reactions and mechanistic aspects. Chem Rev. 2002;102:1731–69. https://doi.org/10.1021/cr0104330.
Wong CH. Enzymatic catalysts in organic synthesis. Science. 1989;244(4909):1145–52. https://doi.org/10.1126/science.265805.
Sheldon RA. Green solvents for sustainable organic synthesis: state of the art. Green Chem. 2005;7:267–78. https://doi.org/10.1039/B418069K.
Rideout DC, Breslow R. Hydrophobic acceleration of Diels-Alder reactions. J Am Chem Soc. 1980;102:7816–7. https://doi.org/10.1021/ja00546a0.
Ros TD, Prato M, Novello F, Maggini M, Banf E. Easy access to water-soluble fullerene derivatives via 1,3-dipolar cycloadditions of Azomethine Ylides to C60. J Org Chem. 1996;61(25):9070–2. https://doi.org/10.1021/jo961522t.
Li CJ, Chen L. Organic chemistry in water. Chem Soc Rev. 2006;35:68–82. https://doi.org/10.1039/B507207G.
Peach J, Beilstein EJ. Supercritical carbon dioxide: a solvent like no other. J Organomet Chem. 2014;10:1878–95. https://doi.org/10.3762/bjoc.10.196.
Welton T. Ionic liquids: a brief history. Biophys Rev. 2018;10(3):691–706.
Wasserscheid P, Welton T. Ionic liquids in synthesis. Weinheim: Wiley-VCH; 2002.
Zhao H, Malhotra SV. Applications of ionic liquids in organic synthesis. Adrichimica Acta. 2002;35(3):75–83.
Sheldon R. Catalytic reactions in ionic liquids. Chem Commun. 2001:2399–407. https://doi.org/10.1039/B107270F.
Steines S, Wasserscheid P, Drießen-Hölscher B. An ionic liquid as catalyst medium for stereoselective hydrogenations of sorbic acid with ruthenium complexes. Angew Chem. 2000;342(4):348–54. https://doi.org/10.1002/(SICI)1521-3897(200004)342:4%3C348::AID-PRAC348%3E3.0.CO;2-6.
Song CE, Roh EJ. Practical method to recycle a chiral (salen)Mn epoxidation catalyst by using an ionic liquid. Chem Commun. 2000;10:837–8. https://doi.org/10.1039/B001403F.
Parshall GW. Catalysis in molten salt media. J Am Chem Soc. 1972;94(25):8716–9. https://doi.org/10.1021/ja00780a013.
Wang P, Chen X, Wang DL, Li YQ, Liu Y. Efficient and recyclable Rh-catalytic system with involvement of phosphine-functionalized phosphonium-based ionic liquids for tandem hydroformylation-acetalization. Green Energy Environ. 2017;2:419–27. https://doi.org/10.1016/j.gee.2017.01.003.
Prechtl MHG, Scholten JD, Dupont J. Carbon-carbon cross coupling reactions in ionic liquids catalysed by palladium metal nanoparticles. Molecules. 2010;15(5):3441–61. https://doi.org/10.3390/molecules15053441.
Mathews CJ, Smith PJ, Welton T. Palladium catalysed Suzuki cross-coupling reactions in ambient temperature ionic liquids. Chem Commun. 2000:249–1250. https://doi.org/10.1039/B002755N.
Sirieix J, Oßberger M, Betzemeier B, Knochel P. Palladium catalyzed cross-couplings of organozincs in ionic liquids. Synlett. 2000;11:1613–5.
Silva MS, Suarez PAZ, de Souza RF, Dupont J. Selective linear dimerization of 1,3-butadiene by palladium compounds immobilized into 1-n-butyl-3-methyl imidazolium ionic liquids. Polym Bull. 1998;40(4–5):401–5. https://doi.org/10.1007/s002890050.
She HY, Judeh ZMA, Ching CB, Xia QH. Comparative studies on alkylation of phenol with tert-butyl alcohol in the presence of liquid or solid acid catalysts in ionic liquids. J Mol Catal A Chem. 2004;212(1–2):301–8. https://doi.org/10.1016/j.molcata.2003.11.007.
Taheri A, Lai B, Cheng C, Gu Y. Brønsted acid ionic liquid-catalyzed reductive Friedel-Crafts alkylation of indoles and cyclic ketones without using external reductant. Green Chem. 2015;17(2):812–6. https://doi.org/10.1039/C4GC01299B.
Tran PH, Duus F, Le TN. Friedel–crafts acylation using bismuth triflate in [BMI][PF6]. Tetrahedron Lett. 2012;53(2):222–4. https://doi.org/10.1016/j.tetlet.2011.11.022.
Nara SJ, Harjani JR, Salunkhe MM. Friedel-crafts sulfonylation in 1-butyl-3-methylimidazolium chloroaluminate ionic liquids. J Organomet Chem. 2001;66(25):8616–20. https://doi.org/10.1021/jo016126b.
Lozano P, Diego T, Guegan PJ, Vaultier M, Iborra JL. Stabilization of α-chymotrypsin by ionic liquids in transesterification reactions. Biotechnol Bioeng. 2001;75(5):563–9. https://doi.org/10.1002/bit.10089.
Plechkovaa NV, Seddon KR. Applications of ionic liquids in the chemical industry. Chem Soc Rev. 2008;37:123–50. https://doi.org/10.1039/B006677J.
Monnier JR, Muehlbauer PJ Selective monoepoxidation of olefins. US Pat 4,897,498. 1990
Saleh YR Preparation of aromatic aldehydes from alkylaromatics and carbon monoxide in the presence of acidic ionic liquids. World Pat 15594. 2000
Siódmiak T, Marsza MP, Proszowska A. Ionic liquids: a new strategy in pharmaceutical synthesis. Mini-Rev Org Chem. 2012;9(2):203–8. https://doi.org/10.2174/157019312800604698.
Kurata A, Kitamura Y, Irie S, Takemoto S, Akai Y, Hirota Y, et al. Enzymatic synthesis of caffeic acid phenethyl ester analogues in ionic liquid. J Biotechnol. 2010b;148(2–3):133–8. https://doi.org/10.1016/j.jbiotec.2010.05.007.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2020 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Ahmed, A. (2020). Sustainable Organic Synthesis in Ionic Liquids. In: Inamuddin, Asiri, A. (eds) Applications of Nanotechnology for Green Synthesis. Nanotechnology in the Life Sciences. Springer, Cham. https://doi.org/10.1007/978-3-030-44176-0_1
Download citation
DOI: https://doi.org/10.1007/978-3-030-44176-0_1
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-44175-3
Online ISBN: 978-3-030-44176-0
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)