Handbook on applications of ultrasound sonochemistry for sustainability

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Handbook on applications of ultrasound sonochemistry for sustainability

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Handbook on Applications of UltrAsoUnd Sonochemistry for Sustainability EditEd by dong CHen | sAnjAy K sHArmA | ACKmez mUdHoo Handbook on Applications of UltrAsoUnd Sonochemistry for Sustainability Handbook on Applications of UltrAsoUnd Sonochemistry for Sustainability EditEd by dong CHen | sAnjAy K sHArmA | ACKmez mUdHoo Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business MATLAB® is a trademark of The MathWorks, Inc and is used with permission The MathWorks does not warrant the accuracy of the text or exercises in this book This book’s use or discussion of MATLAB® software or related products does not constitute endorsement or sponsorship by The MathWorks of a particular pedagogical approach or particular use of the MATLAB® software CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2012 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S Government works Version Date: 20110520 International Standard Book Number-13: 978-1-4398-4207-2 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint Except as permitted under U.S Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including 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Vishwambhar Dayal Sharma Sanjay K Sharma For Yana, Teena, Assad, mum and dad Ackmez Mudhoo Contents Foreword�������������������������������������������������������������������������������������������������������������������������������������������xi Preface������������������������������������������������������������������������������������������������������������������������������������������� xiii Acknowledgments���������������������������������������������������������������������������������������������������������������������������� xv Editors��������������������������������������������������������������������������������������������������������������������������������������������xvii Contributors������������������������������������������������������������������������������������������������������������������������������������xix Chapter Emerging Ubiquity of Green Chemistry in Engineering and Technology Pavel Pazdera Chapter Introduction to Sonochemistry: A Historical and Conceptual Overview 23 Giancarlo Cravotto and Pedro Cintas Chapter Aspects of Ultrasound and Materials Science 41 Andrew Cobley, Timothy J Mason, Larisa Paniwnyk, and Veronica Saez Chapter Ultrasound-Assisted Particle Engineering 75 Anant Paradkar and Ravindra Dhumal Chapter Applications of Sonochemistry in Pharmaceutical Sciences 97 Robina Farooq Chapter Ultrasound-Assisted Synthesis of Nanomaterials 105 Siamak Dadras, Mohammad Javad Torkamany, and Jamshid Sabbaghzadeh Chapter Ultrasound for Fruit and Vegetable Quality Evaluation 129 Amos Mizrach Chapter Ultrasound in Food Technology 163 Taner Baysal and Aslihan Demirdoven Chapter Use of Ultrasound in Coordination and Organometallic Chemistry 183 Boris Ildusovich Kharisov, Oxana Vasilievna Kharissova, and Ubaldo Ortiz-Méndez Chapter 10 Ultrasound in Synthetic Applications and Organic Chemistry 213 Murlidhar S Shingare and Bapurao B Shingate vii viii Contents Chapter 11 Ultrasound in Synthetic Applications and Organic Chemistry 263 Rodrigo Cella Chapter 12 Ultrasound Applications in Synthetic Organic Chemistry 281 Mohammad Majid Mojtahedi and Mohammad Saeed Abaee Chapter 13 Ultrasound-Assisted Anaerobic Digestion of Sludge 323 Ackmez Mudhoo and Sanjay K Sharma Chapter 14 Ultrasound Application in Analyses of Organic Pollutants in Environment 345 Senar Ozcan, Ali Tor, and Mehmet Emin Aydin Chapter 15 Applications of Ultrasound in Water and Wastewater Treatment 373 Dong Chen Chapter 16 Ultrasound and Sonochemistry in the Treatment of Contaminated Soils by Persistent Organic Pollutants 407 Reena Amatya Shrestha, Ackmez Mudhoo, Thuy-Duong Pham, and Mika Sillanpää Chapter 17 Role of Heterogeneous Catalysis in the Sonocatalytic Degradation of Organic Pollutants in Wastewater 419 Juan A Melero, Fernando Martínez, Raul Molina, and Yolanda Segura Chapter 18 Degradation of Organic Pollutants Using Ultrasound 447 Kandasamy Thangavadivel, Mallavarapu Megharaj, Ackmez Mudhoo, and Ravi Naidu Chapter 19 Applications of Ultrasound to Polymer Synthesis 475 Boon Mian Teo, Franz Grieser, and Muthupandian Ashokkumar Chapter 20 Mechanistic Aspects of Ultrasound-Enhanced Physical and Chemical Processes 501 Vijayanand S Moholkar, Thirugnanasambandam Sivasankar, and Venkata Swamy Nalajala Chapter 21 Ultrasound-Assisted Industrial Synthesis and Processes 535 Cezar Augusto Bizzi, Edson Irineu Müller, Érico Marlon de Moraes Flores, Fábio Andrei Duarte, Mauro Korn, Matheus Augusto Gonỗalves Nunes, Paolade Azevedo Mello, and Valderi Luiz Dressler ix Contents Chapter 22 Development of Sonochemical Reactor 581 Keiji Yasuda and Shinobu Koda Chapter 23 Ultrasound for Better Reactor Design: How Chemical Engineering Tools Can Help Sonoreactor Characterization and Scale-Up 599 Jean-Yves Hihn, Marie-Laure Doche, Audrey Mandroyan, Loic Hallez, and Bruno G Pollet Chapter 24 Sonoelectrochemistry: From Theory to Applications 623 Bruno G Pollet and Jean-Yves Hihn Chapter 25 Combined Ultrasound–Microwave Technologies 659 Pedro Cintas, Giancarlo Cravotto, and Antonio Canals Chapter 26 Integrating Ultrasound with Other Green Technologies: Toward Sustainable Chemistry 675 Julien Estager 691 Integrating Ultrasound with Other Green Technologies Hot water HPLC pumps Out In Stainless steel holder Capillary microreactor T-type connector Coil heat exchanger 28 kHz 60 W FIGURE 26.6  Scheme of micro-sonoreactor (Reproduced from Chem Eng Process., 48, Aljbour, S., Yamada, H., and Tagawa, T., Ultrasound-assisted phase transfer catalysis in a capillary microreactor, 1167–1172, Copyright (2009), with permission from Elsevier.) heterogeneous catalysis This field is too large to be comprehensively described in this chapter, but a recent article using an enzyme as a catalyst is particularly interesting (Lee et al., 2008) The authors investigated the transesterification of sugar in a lipase-catalyzed synthesis in 1-butyl-3-methylimi­ dazolium triflate Using ultrasound improved the enzyme activity without degrading it, leading to very interesting results Enzymatic chemistry is interesting from the green chemistry viewpoint, because enzymes are generally extremely efficient and selective catalysts, and operate under very mild conditions, obviously close to the biological ones Even if some other examples are available in the literature, such as the resolution of racemic 1,2-azidoalcohols using lipase Amaro PS (Brenelli and Fernandes, 2003), or the biodegradation of distillery wastewater using an enzyme cellulase (Sangave and Pandit, 2006), the enzymatic sonochemistry remains quite limited but full of potential Another possibility to reach Green sonochemistry is probably the design and characterization of new sonoreactors A great effort has been made for scaling-up sonochemical protocols, and some recent publications describe the design of micro-sonoreactors in which mass transfer is particularly efficient (Costa et al., 2008) The use of microreactors usually implies better yields; thanks to very efficient mass transfer and lower energy consumption due to good heat transfer It is therefore very interesting not only for green chemistry, but also for process intensification as such This methodology has been recently investigated by Aljbour et al (2009) for the liquid–liquid phase transfer reaction between benzyl chloride and sodium sulfide A capillary microreactor immersed in a sonic bath was used in this case, as illustrated in Figure 26.6 (Aljbour et al., 2009) CONCLUSION: THE NEXT STEP The main objective of this chapter was to prove that there is an immense potential for sonochemistry within the green chemistry field As the various phenomena induced by cavitation are well established and accepted by the scientific community, sonochemists have a great goal ahead—to work toward a more sustainable development of chemistry As it has been demonstrated in this chapter, a lot of the tools already exist and can be found in patents or open-literature, and probably more are still to be invented However, this challenging field is not as simple as it may seem, requiring different scientists, from sonochemists to physicists, to work together to achieve further progress For example, who would have thought of introducing an ultrasonic horn into a microwave reactor, in the times when all of the horns were made of metal? Moreover, the biggest challenge of all is maybe 692 Handbook on Applications of Ultrasound: Sonochemistry for Sustainability for chemical engineers who will have to work on the scale-up of these new methodologies, as green chemistry has to offer COST EFFECTIVE and INDUSTRIALLY APPLICABLE solutions, if we not want it to stay confined within the research laboratories As it has been shown comprehensively in this book, there are various industrial syntheses and processes involving ultrasound Green sonochemistry has to follow the same path to make a step further, as it was demonstrated very recently in the case of combined microwave–ultrasound (Leonelly and Mason, 2010) ACKNOWLEDGMENTS The author would like to thank Kenneth R Seddon for his support, and also Malgorzata SwadzbaKwasny and Markus Fanselow from the QUILL Research Centre, Belfast, for their kind help and constructive comments REFERENCES Adewuyi, Y.G 2001 Sonochemistry: Environmental science and engineering applications 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Tetrahedron Asymmetry, 14: 1255–1259 Breslow, R 2007 A fifty-year perspective on chemistry in water In Organic Reactions in Water, Lindstroem U.M (Ed.), pp 1–28, Oxford, U.K.: Blackwell Publishing Ltd Brundtland, C.G 1987 Our Common Future, The World Commission on Environmental Development, Oxford: Oxford University Press Chtourou, M., Abdelhédi, R., Frikha, M.H., and Trabelski, M 2010 Solvent free synthesis of 1,3-diaryl-2-­ propenones catalyzed by commercial acid-clays under ultrasound irradiation Ultrasonics Sonochemistry, 17: 246–249 Cintas, P and Luche, J.L 1999 Green chemistry, Green Chemistry, 1: 115–125 Costa, C., Hihn, J.Y., Rebetez, M., Doche, M.L., Bisel, I., and Moisy, P 2008 Transport-limited current and microsonoreactor characterization at low frequencies in the presence of water, acetonitrile and ­imidazolium-based ionic liquids Physical Chemistry and Chemical Physics, 10: 2149–2158 Cravotto, G., Boffa, L., Mantegna, S., Perega, P., Avogadro, M., and Cintas, P 2008 Improved extraction of vegetable oils under high-intensity ultrasound and/or microwaves Ultrasonics Sonochemistry, 15: 898–902 Integrating Ultrasound with Other Green Technologies 693 Cravotto, G., Beggiato, B., Penani, A et al 2005a High-intensity ultrasound and microwave, alone or combined, promote Pd/C-catalyzed aryl-aryl couplings Tetrahedron Letters, 46: 2267–2271 Cravotto, G and Cintas, P 2007 The combined use of microwave and ultrasound: Improved tools in process chemistry and organic synthesis Chemical European Journal, 13: 1902–1909 Cravotto, G., Palmisano, G., Tollari, S., Nano, G.M., and Penoni, A 2005b The Suzuki homocoupling under high-intensity ultrasound Ultrasonics Sonochemistry, 12: 91–94 Del Campo, F., Neudeck, A., Compton, R., Marken, F., Bull, S., and Davies, S 2001 Sonoelectrochemistry at platinum and boron-doped diamond electrodes: Achieving ‘fast mass transport’ for ‘slow diffusers’ Journal of Electroanalytical Chemistry, 507: 144–151 Deshmukh, R.R., Rajagopal, R., and Srinivasan, K.V 2001 Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids Chemical Communications, 17: 1544–1545 Dhas, N.A and Suslick, K.S 2005 Sonochemical preparation of hollow nanospheres and hollow nanocrystals Journal of American Chemical Society, 127: 2368–2369 Diez-Barra, F., De la Hoz, A., Diaz-Ortiz, A., and Prieto, R 1992 Ultrasound and phase-transfer catalysis without solvent in elimination reactions: Synthesis of cyclic ketene acetals Synletters, 11: 893–894 Enokida, Y., Abd El-Fatah, S., and Wai, C.M 2002 Ultrasound-enhanced dissolution of UO2 in supercritical CO2-soluble extractant for dissolution of uranium dioxide Industrial Engineering and Chemical Research, 41: 2282–2286 Estager, J., Lévêque, J.M., Cravotto, G., Boffa, L., Bonrath, W., and Draye, M 2007a One-pot and solventless synthesis of ionic liquids under ultrasonic irradiation Synletters, 13: 2065–2068 Estager, J., Lévêque, J.M., Turgis, R., and Draye, M 2007b Neat benzoin condensation in recyclable roomtemperature ionic liquids under ultrasonic activation Tetrahedron Letters, 48: 755–759 Filgueiras, A.V., Capelo, J.L., Lavilla I., and Bendicho, C 2000 Comparison of ultrasound-assisted extraction and microwave-assisted digestion for determination of magnesium, manganese and zinc in plant samples by flame atomic absorption spectrometry Talanta, 53: 433–441 Flanningan, D.J., Hopkins, S.D., and Suslick, K.S 2005 Sonochemistry and sonoluminescence in ionic liquids, molten salts, and concentrated electrolyte solutions Journal of Organometallic Chemistry, 690: 3513–3517 Fukushima, T and Aida, T 2007 Ionic liquids for soft functional materials with carbon nanotubes Chemical European Journal, 13: 5048–5058 Gedye, R., Smith, F., Westaway, K., Ali, H., Baldisera, L., Laberge, L., and Roussel, J 1986 The use of microwave ovens for rapid organic synthesis Tetrahedron Letters, 27: 279–282 Gholap, A.R., Venkatesan, K., Daniel, T., Lahoti, R.J., and Srinivasan, K.V 2003 Ultrasound promoted acetylation of alcohols in room temperature ionic liquid under ambient conditions Green Chemistry, 5: 693–696 Gholap, A.R., Venkatesan, K., Daniel, T., Lahoti, R.J., and Srinivasan, K.V 2004 Ionic liquid promoted novel and efficient one pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones at ambient temperature under ultrasound irradiation Green Chemistry, 6: 147–150 Goharshadi, E.K., Ding, Y., Jorabchi, M.N., and Nancarrow, P 2009 Ultrasound-assisted green synthesis of nanocrystalline ZnO in the ionic liquid [hmim][NTf2] Ultrasonics Sonochemistry, 16: 120–123 Gutierrez-Sanchez, C., Calvino-Castilda, V., Perez-Mayoral, E et al 2009 Coumarins preparation by Pechmann under ultrasound irradiation Synthesis of Hymecromone as insecticide intermediate Catalysis Letters, 182: 318–322 Hamdaoui, O and Naffrechoux, E 2008 Sonochemical and photosonochemical degradation of 4-chlorophenol in aqueous media Ultrasonics Sonochemistry, 15: 981–987 Hao, H., Chen, Y., Wu, M., Wang, H., Yin, Y., and Lü, Z 2004 Sonochemistry of degrading p-chlorophenol in water by high frequency ultrasound Ultrasonics Sonochemistry, 11: 43–46 Harada, H 2001 Sonophotocatalytic decomposition of water using TiO2 photocatalyst Ultrasonics Sonochemistry, 8: 55–58 Heravi, M.R.P 2009 An efficient synthesis of quinolines derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation via tandel addition/annulations reaction of O-aminoaryl ketones with alpha-methylene ketones Ultrasonics Sonochemistry, 16: 361–366 Hu, A.J., Zhao, S.V., Liang, H., Qiu, T.Q., and Chen, G 2007 Ultrasound assisted supercritical fluid extraction of oil and coixenolide from adley seed Ultrasonics Sonochemistry, 14: 219–224 Inazu, K., Nagata, Y., and Maeda, Y 1993 Decomposition of chlorinated hydrocarbons in aqueous solution by ultrasonic irradiation Chemical Letters, 57–60 694 Handbook on Applications of Ultrasound: Sonochemistry for Sustainability Ince, N.H., Tezcanli, G., Belen, R.K., and Apikyan, I.G 2001 Ultrasound as a catalyzer of aqueous ­reaction systems: The state of the art and environmental applications Applied Catalysis B: Environment, 29: 167–176 Jessop, P and Leitner, W 1999 Chemical Synthesis Using Supercritical Fluids, Weinheim, Germany: Wiley-VCH Jiang, Y., Pétrier, C., and Waite, D 2006 Sonolysis of 4-chlorophenol in aqueous solution: Effects of substrate concentration, aqueous temperature and ultrasonic frequency Ultrasonics Sonochemistry, 13: 415–422 Lee, S.H., Nguyen, H.M., Koo, Y.M., and Ha, S.H 2008 Ultrasound-enhanced lipase activity in the synthesis of sugar ester using ionic liquids Process Biochemistry, 43: 1009–1012 Leonelly, C and Mason, T.J., 2010 Microwave and ultrasonic processing: Now a realistic option for industry Chemical Engineering and Process, 49: 885–900 Lévêque, J.M., Estager, J., Draye, M., Cravotto, G., Boffa, L., and Bonrath, W 2007 Synthesis of ionic liquids using non conventional activation methods An overview Monatshefte für Chemie, 138: 1103–1113 Li, X., Zhao, J., Li, Q., Wang, L., and Tsang, S.C 2007 Ultrasonic chemical oxidative degradations of 1,3-dialkyimidazolium ionic liquids and their mechanistric elucidations Dalton Transactions, 19: 1875–1880 Loupy, A 2006 Microwave in Organic Synthesis, 2nd edn., Weinheim, Germany: Wiley-VCH Luche, J.L 1993 Sonochemistry from experiments to theoretical considerations In Advances in Sonochemistry, Mason T.J (Ed.), pp 85–124, London, U.K.: JAI Press Luche, J.L 1998 Synthetic Organic Sonochemistry, New York: Plenum Press Maeda, M and Amemiya, H 1995 Chemical effects under simultaneous irradiation by microwaves and ultrasound New Journal of Chemistry, 19: 1023–1028 Makosza, M 1975 Two-phase reactions in the chemistry of carbanions and halocarbenes-useful tool in organic synthesis Pure and Applied Chemistry, 43: 439–462 Makosza, M 2000 Phase-transfer catalyst A general green methodology in organic synthesis Pure and Applied Chemistry, 72: 1399–1403 Memarian, H.R and Abdoli-Senejani, M 2008 Ultrasound-assisted photochemical oxidation of unsymmetrically substituted 1,4-dihydropyridines Ultrasonics Sonochemistry, 15: 110–114 Mikkola, J.P., Kirilin, A., Tuuf, J.C et al 2007 Ultrasound enhancement of cellulose processing in ionic ­liquids: From dissolution towards functionalization Green Chemistry, 9: 1229–1237 Mojtahedi, M.M., Javadpour, M., and Abaee, M.S 2008 Convenient ultrasound synthesis of substituted pyrazolones under solvent-free conditions Ultrasonics Sonochemistry, 15: 228–232 Park, I.B., Son, Y., Song, I.S., Kim, J., and Khim, J 2008 Remediation of diesel-contaminated soil using supercritical carbon dioxide and ultrasound Japanese Journal of Applied Physics, 47: 4314–4316 Peng, Y and Song, G 2003 Combined microwave and ultrasound accelerated Knoevenagel-Doebner reaction in aqueous media: A green route to 3-aryl acrylic acids, Green Chemistry, 5: 704–706 Peng, Y., Zhong, W., and Song, G 2005 Efficient and mild room temperature reduction of benzophenones under ultrasound irradiation Ultrasonics Sonochemistry, 12: 169–172 Perreux, L and Loupy, A 2002 Nonthermal effects of microwave in organic synthesis In Microwave in Organic Synthesis, Loupy, A (Ed.), pp 61–114, Weinheim, Germany: Wiley-VCH Peters, D 2001 Sonolytic degradation of volatile pollutants in natural groundwater: Conclusions from a model study Ultrasonics Sonochemistry, 8: 221–226 Pétrier, C., Lamy, M.F., Francony, A et al 1994 Sonochemical degradation of phenol in dilute aqueous solutions: Comparison of the reaction rates at 20 and 487 kHz Journal of Physical Chemistry, 98: 10514–10520 Plechkova, N.V and Seddon, K.R 2008 Applications of ionic liquids in the chemical industry Chemical Society Reviews, 37: 123–150 Puri, S., Kaur, B., Parmar, A., and Kumar, H 2009 Ultrasound-promoted greener synthesis of 2H-chromen-2-ones catalyzed by copper perchlorate in solventless media Ultrasonics Sonochemistry, 16: 705–707 Ragaini, V and Bianchi, C.L 1998 Sonochemical catalytic reactions In Synthetic Organic Sonochemistry, Luche, J.L (Ed.), pp 235–261, New York: Plenum Press Rajagopal, R., Jarikote, D.V., and Srinivasan, K.V 2002 Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions Chemical Communications, 616–617 Ranu, R.C and Mandal, T 2006 Indium(I) iodide as a radical initiator : Intramolecular cyclization of functionalized bromo-alkynes to substituted tetrahydrofurans Tetrahedron Letters, 47: 2859–2861 Integrating Ultrasound with Other Green Technologies 695 Reddy, E.P., Daydov, L., and Smirniotis, P 2003 TiO2-loaded zeolites and mesoporous materials in the sonophotocatalytic decomposition of aqueous organic pollutants: The role of the support Applied Catalysis B: Environment, 42: 1–11 Riera, E., Golas, Y., Blanco, A., Gallego, J.A., Blasco, M., and Mulet, A 2004 Mass transfer enhancement in supercritical fluids extraction by means of power ultrasound Ultrasonics Sonochemistry, 11: 241–244 Rodriguez, I., Llompart, M.P., and Cela, R 2000 Solid-phase extraction of phenols Journal of Chromatography, 885: 291–304 Sangave, P.C and Pandit, A.B 2006 Ultrasound and enzyme assisted biodegradation of distillery waste water Journal of Environmental Management, 80: 36–46 Schmitt, F.O., Johnson, C.H., and Olson, A.R 1928 Oxidations promoted by ultrasonic radiation Journal of American Chemical Society, 51: 370–375 Serpone, N., Terzian, R., Colarusso, P., Minero, C., Pelizetti, E., and Hidaka, H 1992 Sonochemical oxidation of phenol and three of its intermediate products in aqueous media: Pyrocatechol, hydroquinone, and benzoquinone Kinetic and mechanistic aspects Research on Chemical Intermediates, 18: 183–202 Sheldon, R.A 1994 Consider the environmental quotient CHEMTECH, 24: 38–47 Sheldon, R.A 2008 E factors, green chemistry and catalysis: An odyssey Chemical Communications, 29: 3352–3365 Sheldon, R.A., Arends, I.W.C.E., and Hanefeld, U 2007 Green Chemistry and Catalysis, Weinheim, Germany: Wiley-VCH Stock, N.L., Peller, J., Vinodgopal, K., and Kamat, P.V 2000 Combinative sonolysis and photocatalysis for textile dye degradation Environmental Science and Technology, 34: 1747–1750 Strauss, C.R and Varma, R.S 2006 Microwaves in green and sustainable chemistry Topics in Current Chemistry, 266: 199–231 Suslick, K.S., Hammerton, D.A., and Cline, R.E Jr 1990 Sonochemical hot spot Journal of American Chemical Society, 108: 5641–5642 Tanchoux, N and Leitner, W 2002 Supercritical carbon dioxide as an environmentally benign reaction medium for chemical syntheses In Handbook of Green Chemistry and Technologies, Clark, J., and Macquarrie, D (Eds.), pp 482–501, Oxford, U.K.: Blackwell Science Ltd Tang, S.Y., Bourne, R.A., Smith, R.L., and Poliakoff, M 2008 The 24 principles of green engineering and green chemistry: “Improvements productively” Green Chemistry, 7: 268–269 Toda, F., Tanaka, K., and Iwata, J 1989 Oxidative coupling reactions of phenols with iron(III) chloride in the solid state Journal of Organic Chemistry, 54: 3007–3009 Toma, S., Gaplovsky, A., and Luche, J.L 2001 The effect of ultrasound on photochemical reactions Ultrasonics Sonochemistry, 8: 201–207 Toukoniity, B., Mikkola, J.P., Murzin, D.Y., and Salmi, T 2008 Utilization of electromagnetic and acoustic irradiation in enhancing heterogeneous catalytic reactions Trends in Chemical Engineering, 11: 1–37 Toy, M.S and Stringham, R.S 1984 Ultrasonic photolysis of methyl disulfide and hexafluorobutadiene Journal of Fluorine Chemistry, 25: 213–218 Trofimov, T.I., Samsonov, M.D., Lee, S.C., Smart, N.G., and Wai, C.M 2001 Ultrasound enhancement of dissolution kinetics of uranium oxides in supercritical carbon dioxide Journal of Chemical Technology and Biotechnology, 76: 1223–1226 Trost, B.M 1991 The atom economy: A search for synthetic efficiency Science, 254: 1471–1477 Tucker, J.L 2010 Green chemistry: Cresting a summit towards sustainability Organic Process Research and Development, 14: 328–331 Venkatesan, K., Pujari, S.S., Lahoti, R.J., and Srinivasan, K.V 2008 An efficient synthesis of 1,8-dioxo-­ octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation Ultrasonics Sonochemistry, 15: 548–553 Wadhawan, J., Del Campo, F., Compton, R et al 2001 Emulsion electrosynthesis in the presence of power ultrasound Biphasic Kolbe coupling processes at platinum and boron-doped diamond electrodes Journal of Electroanalytical Chemistry, 507: 135–143 Wang, S.X., Li, Z.Y., Zhang, J.C., and Li, J.T 2008 The solvent-free synthesis of 1,4-dihydropyridines under ultrasound irradiation without catalyst Ultrasonics Sonochemistry, 15: 677–680 Wasserscheid, P and Welton, T 2008 Ionic Liquids in Synthesis, 2nd edn., Weinheim, Germany: Wiley-VCH Woods, R and Loomis, A 1927 The physical and biological effects of high frequency sound waves of great intensity Philosophia Magazine, 4: 414–436 696 Handbook on Applications of Ultrasound: Sonochemistry for Sustainability Yang, J.M., Ji, S.J., Gu, D.G., Shen, Z.L., and Wang, S.Y 2005 Ultrasound-irradiated addition of ferrocenylenones under solvent-free and catalyst-free conditions at room temperature Journal of Organometallic Chemistry, 690: 2989–2995 Zhang, Z.H., Li, J.J., and Li, T.S 2008 Ultrasound-assisted synthesis of pyrroles catalyzed in zirconium chloride in solvent-free conditions Ultrasonics Sonochemistry, 15: 673–676 Zhou, Y 2005 Recent advances in ionic liquids for synthesis of inorganic nanomaterials Current Nanoscience, 1: 35–42 Zhu, J., Liu, S., Palchnik, O., Koltypin, Y., and Gedanken, A 2000 A novel sonochemical method for the preparation of nanophasic sulfides: Synthesis of HgS and PbS nanoparticles Journal of Solid State Chemistry, 153: 342–348 Zosel, K US Patent Application No 784,744, May 19, 1977 101 102 103 104 105 106 Human hearing (10 Hz–18 kHz) Power ultrasound (20–100 kHz: cleaning and sonochemistry) Extended range: 100 kHz–1 MHz High frequency (1–10 MHz: medical diagnosis; analysis) FIGURE 2.1  Sound frequencies (scale in Hz) Ultrasound horn M M H2O (vap) H + OH Cavitation bubble Monomer droplets Implosion M Radical entry Surfactant M Polymerization FIGURE 19.4  Diagram of the proposed sonochemical miniemulsion polymerization pathway The ultrasound from the horn tip produces cavitation bubbles that upon collapse generate the conditions that lead to primary radical formation and emulsification of the monomer Monomeric radicals are mainly formed at the surface of the cavitation bubbles and subsequently enter into monomer droplets producing latex particles High shear Hydrophobic nanomaterials dispersed in monomer phase Addition of water and surfactant Polymerization Surfactant stabilized monomer droplets containing encapsulated nanomaterials Surfactant stabilized polymer particles containing encapsulated nanomaterials FIGURE 19.7  Schematic diagram of the procedure for the encapsulation of hydrophobic nanomaterials and the 1:1 copy of monomer droplets to latex particles by the sonochemically driven miniemulsion polymerization pathway FIGURE 23.3  Laser visualization at 20 kHz (From Ultrason Sonochem., 11, Viennet, R., Ligier, V., Hihn, J.-Y., Bereiziat, D., Nika, P., and Doche, M.-L., Visualisation and electrochemical determination of the actives zones in an ultrasonic reactor using 20 and 500 kHz frequencies, 125–129, Copyright (2004), with permission from Elsevier.) FIGURE 23.4  Horizontal cutting close to the transducer (From Ultrason Sonochem., 11, Viennet, R., Ligier, V., Hihn, J.-Y., Bereiziat, D., Nika, P., and Doche, M.-L., Visualisation and electrochemical determination of the actives zones in an ultrasonic reactor using 20 and 500 kHz frequencies, 125–129, Copyright (2004), with permission from Elsevier.) FIGURE 23.5  Vertical light sheet in the entire reactor volume (From Ultrason Sonochem., 11, Viennet, R., Ligier, V., Hihn, J.-Y., Bereiziat, D., Nika, P., and Doche, M.-L., Visualisation and electrochemical determination of the actives zones in an ultrasonic reactor using 20 and 500 kHz frequencies, 125–129, Copyright (2004), with permission from Elsevier.) (a) (b) FIGURE 23.6  (a) Visualization in the entire reactor volume; (b) radial distribution close to the transducer (From Ultrason Sonochem., 11, Viennet, R., Ligier, V., Hihn, J.-Y., Bereiziat, D., Nika, P., and Doche, M.-L., Visualisation and electrochemical determination of the actives zones in an ultrasonic reactor using 20 and 500 kHz frequencies, 125–129, Copyright (2004), with permission from Elsevier.) FIGURE 23.7  Details close to the water/air interface at high frequency (From Ultrason Sonochem., 11, Viennet, R., Ligier, V., Hihn, J.-Y., Bereiziat, D., Nika, P., and Doche, M.-L., Visualisation and electrochemical determination of the actives zones in an ultrasonic reactor using 20 and 500 kHz frequencies, 125–129, Copyright (2004), with permission from Elsevier.) Vy Shadow Vx Electrode Vy Shadow Electrode Vy Vx Electrode-tip gap = 30 mm Electrode-tip gap = 10 mm FIGURE 23.8  Laser visualization of ultrasonic actives zones in electrode presence Electrode Vy Vx Equivalent fluid velocity Ueq (m s–1) FIGURE 23.18  Equivalent fluid velocity—coordinate system Electrode Vy d Vx FIGURE 23.19  Determination of the “equivalent flow” in the zone close to the transducer FIGURE 23.21  Fluorescent tracers (From Ultrason Sonochem., 16, Mandroyan, A., Doche, M.-L., Hihn, J.-Y., Viennet, R., Bailly, Y., and Simonin, L., Modification of the ultrasound induced activity by the presence of an electrode in a sono-reactor working at two low frequencies (20 and 40 kHz) Part II: Mapping flow velocities by particle image velocimetry (PIV), 97–104, Copyright (2009b), with permission from Elsevier.) General Chemistry Handbook on Applications of UltrAsoUnd Sonochemistry for Sustainability Ultrasonic irradiation and the associated sonochemical and sonophysical effects are complementary techniques for driving more efficient chemical reactions and yields Sonochemistry—the chemical effects and applications of ultrasonic waves—and sustainable (green) chemistry both aim to use less hazardous chemicals and solvents, reduce energy consumption, and increase product selectivity A comprehensive collection of knowledge, Handbook on Applications of Ultrasound covers the most relevant aspects linked to and linking green chemistry practices to environmental sustainability through the uses and applications of ultrasound-mediated and ultrasound-assisted biological, biochemical, chemical, and physical processes Chapters are presented in the areas of: • Medical applications • drug and gene delivery • Nanotechnology • Food technology • Synthetic applications and organic chemistry • Anaerobic digestion • Environmental contaminants degradation • Polymer chemistry • industrial syntheses and processes • Reactor design • Electrochemical systems • Combined ultrasound− microwave technologies While the concepts of sonochemistry have been known for more than 80 years, in-depth understanding of this phenomenon continues to evolve Through a review of the current status of chemical and physical science and engineering in developing more environmentally friendly and less toxic synthetic processes, this book highlights many existing applications and enormous potential of ultrasound technology to upgrade present industrial, agricultural, and environmental processes K11960 an informa business w w w c r c p r e s s c o m 6000 Broken Sound Parkway, NW Suite 300, Boca Raton, FL 33487 711 Third Avenue New York, NY 10017 Park Square, Milton Park Abingdon, Oxon OX14 4RN, UK w w w c r c p r e s s c o m .. .Handbook on Applications of UltrAsoUnd Sonochemistry for Sustainability Handbook on Applications of UltrAsoUnd Sonochemistry for Sustainability EditEd by dong CHen | sAnjAy... situations or states which are non-sustainable It stands to reason Handbook on Applications of Ultrasound: Sonochemistry for Sustainability that the LCA for a paper copy of the The Times and for. .. this handbook provides a robust pool of knowledge on the green applications of sonochemistry We also feel it provides up-to-date information on some selected fields of applied research of ultrasound

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