Water as the Green Solvent in Organic Synthesis
Kartick Chandra Majhi, Paramita Karfa, Sunil Kumar, Rashmi Madhuri
The rising environmental awareness of the chemical society has forced researchers to find an alternative non-polluting medium and procedure for all kind of chemical synthesis. Use of safe and less toxic chemicals as the solvent is one of the most important criteria among the “green chemistry” principles. From a very long time, solvents are being used in large quantity in the chemical and pharmaceutical productions. Nature and properties of solvents are important parameters, which suggest the impact of the chemical industry on the environment as well as on all the other living systems. The purpose of using “green solvents” is to reduce or eliminate the toxic or lethal effects of chemicals on the environment. The continuous increase in the requirement of a more sustainable approach in synthesis procedures leads to an emerging interest in the use of water as a solvent. Use of water as a solvent in chemical synthesis is one of the best options in green chemistry, to minimize the release of harmful chemicals in the environment. Using water as a solvent, reactions can be performed under mild experiment conditions and the catalysts can be reused, which decrease the overall cost of the product. In this chapter, the importance of water as a green solvent and its involvement in various chemical and organic synthesis processes are described. Here, the main focus has been on the role of water in recent processes of (organic, nanomaterials and organometallic compounds) and polymerization processes. In all the discussed processes, water has been used as a safe, less harmful, cost-effective and environmentally friendly option as a solvent.
Keywords
Green Chemistry, Green Solvent, Organic Synthesis, Nanomaterial Synthesis, Organometallic Compound Synthesis, Polymerization
Published online 8/20/2019, 20 pages
Citation: Kartick Chandra Majhi, Paramita Karfa, Sunil Kumar, Rashmi Madhuri, Water as the Green Solvent in Organic Synthesis, Materials Research Foundations, Vol. 54, pp 182-201, 2019
DOI: https://doi.org/10.21741/9781644900314-8
Part of the book on Industrial Applications of Green Solvents
References
[1] H. Kari, M.L. Riekkola, Water as the first choice green solvent, in: F.P. Pereira, M. Tobiszewski (Eds.), The application of green solvents in separation processes, Elsevier, 2017, pp. 19-55. https://doi.org/10.1016/b978-0-12-805297-6.00002-4
[2] S.M. Olivier, C.J. Li, Green chemistry oriented organic synthesis in water, Chem. Soc. Rev. 41 (2012) 1415-1427. https://doi.org/10.1039/c1cs15222j
[3] P. Pamela, E.A. Davey, E.E.U. Benavides, C.A. Eckert, C.L. Liotta, Solvents for sustainable chemical processes, Green Chem. 16 (2014) 1034-1055. https://doi.org/10.1039/c3gc42302f
[4] P. Loic, M.Z. Ozel, S. Perino, J. Wajsman, F. Chemat, Water as green solvent for extraction of natural products, in: F. Chemat, J. Strube (Eds.), Green extraction of natural products, Wiley, Weinheim, 2015, pp. 237-264. https://doi.org/10.1002/9783527676828.ch7
[5] L. Andre, J. Auge, Water as solvent in organic synthesis, in: Knochel, Paul (Eds.), Modern solvents in organic synthesis, Springer, Berlin, Heidelberg, 1999pp. 1-39.
[6] T.P. Anastas, J.C. Warner, Green chemistry: theory and practice. Oxford [England]; New York: Oxford University Press 1998.
[7] C. Christian, U. Fischer, K. Hungerbuhler, What is a green solvent? A comprehensive framework for the environmental assessment of solvents, Green Chem. 9 (2007) 927-934. https://doi.org/10.1039/b617536h
[8] W. Blokzijl, J.B.F.N. Engberts, Hydrophobic effects. Opinions and facts, Angew. Chem. Int. Ed. 32 (1993) 1545-1579. https://doi.org/10.1002/anie.199315451
[9] J.L. Finney, Water? What’s so special about it? Phil.Trans. Biol. Sci. 359 (2004) 1145-1165.
[10] N. George, H.A. Scheraga, Structure of water and hydrophobic bonding in proteins. I. A model for the thermodynamic properties of liquid water, J. Chem. Phys. 36 (2004) 3382-3400.
[11] N. Galamba, Water’s structure around hydrophobic solutes and the iceberg model, The J. Phys. Chem. B 117 (2013) 2153-2159. https://doi.org/10.1021/jp310649n
[12] S.A. Rice, G.S. Mark, A random network model for water, J. Phys. Chem. 85 (1981) 1108-1119.
[13] R.R. Peters, E.A. Klavetter, A continuum model for water movement in an unsaturated fractured rock mass, Water Resour. Res. 24 (1988) 416-430. https://doi.org/10.1029/wr024i003p00416
[14] S.H. Eugene, J. Teixeira, Interpretation of the unusual behavior of H2O and D2O at low temperatures: tests of a percolation model, J. Chem. Phys. 73 (2008) 3404-3422.
[15] L. Lei, Q.X. Guo, Isokinetic relationship, isoequilibrium relationship, and enthalpy-entropy compensation, Chem. Rev. 101 (2001) 673-696. https://doi.org/10.1021/cr990416z
[16] K.R. Gallagher, K.A. Sharp, A new angle on heat capacity changes in hydrophobic solvation, J. Am. Chem. Soc. 125 (2003) 9853-9860. https://doi.org/10.1021/ja029796n
[17] W. Kauzmann, Thermodynamics of unfolding, Nature, 325 (1987) 763-764.
[18] M. Siskin, A.R. Katritzky, Reactivity of organic compounds in superheated water: General background, Chem. Rev. 101 (2001) 825-836. https://doi.org/10.1021/cr000088z
[19] D.C. Rideout, R. Breslow, Hydrophobic acceleration of Diels-Alder reactions, J. Am. Chem. Soc. 102 (1980) 7816-7817. https://doi.org/10.1021/ja00546a048
[20] N. Rieber, J. Alberts, J.A. Lipsky, D.M. Lemal, DELTA 1-1, 2-Diazetines, J. Am. Chem. Soc. 91 (1969) 5668-5669. https://doi.org/10.1021/ja01048a056
[21] L. Yu, D. Chen, P.G. Wang, Aqueous aza Diels-Alder reactions catalyzed by lanthanide (III) trifluoromethanesulfonates. Tetrahedron Lett. 25 (1996) 2169-2172. https://doi.org/10.1016/0040-4039(96)00222-5
[22] F.M. Silva, J.J. Jones, Organic reaction in water. Part 31: diastereoselectivity in Michael additions of thiophenol to nitroolefins in aqueous media. J. Braz. Chem. Soc. 12 (2001) 135-137. https://doi.org/10.1590/s0103-50532001000200002
[23] Y. Mori, J. Kobayashi, K. Manabe, S. Kobayashi, Use of boron enolates in water. The first boron enolate-mediated diastereoselective aldol reactions using catalytic boron sources. Tetrahedron 58 (2002) 8263-8268. https://doi.org/10.1016/s0040-4020(02)00976-6
[24] G. Brahmachari, Room temperature one-pot green synthesis of coumarin-3 carboxylic acids in water: a practical method for the large-scale synthesis. ACS Sustainable Chem. Eng. 27 (2015) 2350-2358. https://doi.org/10.1021/acssuschemeng.5b00826
[25] P.B. Khoza, M.J. Moloto, L. Sikhwivhilu, The effect of solvents, acetone, water, and ethanol, on the morphological and optical properties of ZnO nanoparticles prepared by microwave, Journal of Nanotechnology (2012). https://doi.org/10.1155/2012/195106
[26] J.V. Swetha, H. Parse, B. Kakade, A. Geetha Morphology-dependent facile synthesis of manganese oxide nanostructures for oxygen reduction reaction, Solid State Ionics, 15 (2018) 1-7. https://doi.org/10.1016/j.ssi.2018.11.002
[27] A. Nikitin, M. Khramtsov, A. Garanina, P. Mogilnikov, N. Sviridenkova, I. Shchetinin, A. Savchenko, M Abakumov, A. Majouga, Synthesis of iron oxide nanorods for enhanced magnetic hyperthermia. J. Magn. Magn. Mater. 469 (2019) 443-449. https://doi.org/10.1016/j.jmmm.2018.09.014
[28] D. Vengust, M. Podlogar, A. Mrzel, M. Vilfan, Rapid reaction of Mo2N nanowires with Pb2+ ions in water and its use for production of PbMoO4 nanoparticles, Mater. Chem. Phys. 15 (2019) 20-5. https://doi.org/10.1016/j.matchemphys.2019.01.018
[29] S. Moussa, A.R. Siamaki, B.F. Gupton, M.S. El-Shall, Pd-partially reduced graphene oxide catalysts (Pd/PRGO): laser synthesis of Pd nanoparticles supported on PRGO nanosheets for carbon-carbon cross-coupling reactions, ACS Catal. 2 (2012) 145-154. https://doi.org/10.1021/cs200497e
[30] J. Ahmed, Y. Mao, Delafossite CuAlO2 nanoparticles with electrocatalytic activity toward oxygen and hydrogen evolution reactions, in: J.L. Liu, S. Bashir (Eds.)Nanomaterials for Sustainable Energy, ACS Symposium Series; American Chemical Society, Kingsville, 2015 pp. 57-72. https://doi.org/10.1021/bk-2015-1213.ch004
[31] R.K. Sahu, S.S. Hiremath, Synthesis of aluminium nanoparticles in a water/polyethylene glycol mixed solvent using μ-EDM, In IOP Conference Series: Materials Science and Engineering 225 (2017) 012257. https://doi.org/10.1088/1757-899x/225/1/012257
[32] M. Chauhan, K.P. Reddy, C.S. Gopinath, S. Deka, Copper cobalt sulphide nanosheets realizing a promising electrocatalytic oxygen evolution reaction, ACS Catal. 7 (2017) 5871-5879. https://doi.org/10.1021/acscatal.7b01831
[33] K. Ojha, S. Saha, S. Banerjee, A. K. Ganguli, Efficient electrocatalytic hydrogen evolution from MoS2-functionalized Mo2N nanostructures. ACS Appl. Mater. Interfaces 9 (2017) 19455-19461. https://doi.org/10.1021/acsami.6b10717
[34] K. Ojha, S. Saha, B. Kumar, K.S. Hazra, A. K. Ganguli, Controlling the morphology and efficiency of nanostructured molybdenum nitride electrocatalysts for the hydrogen evolution reaction, ChemCatChem, 8 (2016)1218-1225. https://doi.org/10.1002/cctc.201501341
[35] Hu, Y. Feng, J. Nai, D. Zhao, Y. Hu, X.W. Lou, Construction of hierarchical Ni-Co-P hollow nano bricks with oriented nanosheets for efficient overall water splitting, Energy Environ. Sci. 4 (2018) 872-880. https://doi.org/10.1039/c8ee00076j
[36] M. Taei, E. Havakeshian, F. Hasheminasab, A gold nano dendrite-decorated layered double hydroxide as a bifunctional electrocatalyst for hydrogen and oxygen evolution reactions in alkaline media, RSC Adv. 74 (2017) 47049-47055. https://doi.org/10.1039/c7ra05625g
[37] H. Sun, Y. Zhao, K. Molhave, M. Zhang, J. Zhang, Simultaneous modulation of surface composition, oxygen vacancies and assembly in hierarchical Co3O4mesoporous nanostructures for lithium storage and electrocatalytic oxygen evolution, Nanoscale 38 (2017) 14431-14441. https://doi.org/10.1039/c7nr03810k
[38] X. Xu, R. Ray, Y, Gu, H.J. Ploehn, L. Gearheart, K. Raker, W.A. Scrivens, Electrophoretic analysis and purification of fluorescent single-walled carbon nanotube fragments, J. Am. Chem. Soc. 126 (2004) 12736-12737. https://doi.org/10.1021/ja040082h
[39] L. Li, R. Zhang, C. Lu, J. Sun, L. Wang, B. Qu, T. Li, Y. Liu, S. Li, In situ synthesis of NIR-light emitting carbon dots derived from spinach for bio imaging applications, J. Mater. Chem. B 5 (2017) 7328-34. https://doi.org/10.1039/c7tb00634a
[40] A. Yanagisawa, H. Inoue, M. Morodome, H. Yamamoto, Highly chemoselective allylation of carbonyl compounds with tetraallyltin in acidic aqueous media, J. Am. Chem. Soc. 115 (1993) 10356-10357. https://doi.org/10.1021/ja00075a060
[41] L.J. Chao, The greening of a fundamental reaction: metal‐mediated reactions in water, in: P.T. Anastas, L.G. Heine, T.C. Williamson, (Eds.), Green Chemical Syntheses and Processes, ACS Symposium Series; American Chemical Society, Washington, 2001, pp. 74-86. https://doi.org/10.1021/bk-2000-0767.ch007
[42] S. Venkatraman, C.J. Li, Carbon-carbon bond formation via Palladium catalyzed reductive coupling in air,Org. Lett. 7 (1999) 1133-1135. https://doi.org/10.1021/ol9909740
[43] A.K. Yadav, M.J. Barandiaran, J.C. de la Cal, Synthesis of water-borne polymer nanoparticles in a continuous microreactor, Chem. Eng. J. 198 (2012) 191-200. https://doi.org/10.1016/j.cej.2012.05.091
[44] I. Chaduc, M. Lansalot, F.D. Agosto, B. Charleux, RAFT polymerization of methacrylic acid in water, Macromolecules, 45 (2012) 1241-1247. https://doi.org/10.1021/ma2023815
