Microwave Heating as a Tool for Sustainable Chemistry Sustainability: Contributions through Science and Technology Series Editor: Michael C Cann, Ph.D Professor of Chemistry and Co-Director of Environmental Science University of Scranton, Pennsylvania Preface to the Series Sustainability is rapidly moving from the wings to center stage Overconsumption of nonrenewable and renewable resources, as well as the concomitant production of waste has brought the world to a crossroads Green chemistry, along with other green sciences technologies, must play a leading role in bringing about a sustainable society The Sustainability: Contributions through Science and Technology series focuses on the role science can play in developing technologies that lessen our environmental impact This highly interdisciplinary series discusses significant and timely topics ranging from energy research to the implementation of sustainable technologies Our intention is for scientists from a variety of disciplines to provide contributions that recognize how the development of green technologies affects the triple bottom line (society, economic, and environment) The series will be of interest to academics, researchers, professionals, business leaders, policy makers, and students, as well as individuals who want to know the basics of the science and technology of sustainability Michael C Cann Published Titles Green Chemistry for Environmental Sustainability Edited by Sanjay Kumar Sharma, Ackmez Mudhoo, 2010 Microwave Heating as a Tool for Sustainable Chemistry Edited by Nicholas E Leadbeater, 2010 Sustainability: Contributions through Science and Technology Series Editor: Michael C Cann Edited by Nicholas E Leadbeater Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business Cover image created by Nicholas E Leadbeater and Sarah Louise Upjohn CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2011 by 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http://www.crcpress.com Contents Series Preface vii Preface .ix Contributors .xi Chapter Microwave Heating as a Tool for Sustainable Chemistry: An Introduction Jason R Schmink and Nicholas E Leadbeater Chapter Microwave Heating as a Tool for Organic Synthesis 25 Robert A Stockland, Jr Chapter Microwave Heating as a Tool for Sustainable Polymer Chemistry 53 Mauro Iannelli Chapter Microwave Heating as a Tool for Drug Discovery 73 Ping Cao and Nicholas E Leadbeater Chapter Microwave Heating as a Tool for Process Chemistry 105 Jonathan D Moseley Chapter Microwave Heating as a Tool for the Undergraduate Organic Chemistry Laboratory 149 Cynthia B McGowan and Nicholas E Leadbeater Chapter Microwave Heating as a Tool for Inorganic and Organometallic Synthesis 175 Gregory L Powell Chapter Microwave Heating as a Tool for Materials Chemistry 207 Steven L Suib and Nicholas E Leadbeater v vi Contents Chapter Microwave Heating as a Tool for the Biosciences 231 Grace S Vanier Index 271 Series Preface Sustainability is rapidly moving from the wings to center stage Overconsumption of nonrenewable and renewable resources, as well as the concomitant production of waste has brought the world to a crossroads Green chemistry, along with other green sciences and technologies, must play a leading role in bringing about a sustainable society The Sustainability: Contributions through Science and Technology series focuses on the role science can play in developing technologies that lessen our environmental impact This highly interdisciplinary series discusses significant and timely topics ranging from energy research to the implementation of sustainable technologies Our intention is for scientists from a variety of disciplines to provide contributions that recognize how the development of green technologies affects the triple bottom line (society, economy, and environment) The series will be of interest to academics, researchers, professionals, business leaders, policy makers, and students, as well as individuals who want to know the basics of the science and technology of sustainability Michael C Cann Scranton, Pennsylvania vii Preface After arriving home hungry following a long day in the laboratory or the office, we all know that the fastest way to heat up last night’s leftovers is to use a microwave oven Since Percy Spencer first noticed that candy bars melt when close to radar sets, thus leading to the development of the first domestic microwave oven in 1947, the technology is now pretty much in every home Dow Chemical Company filed a patent in 1969 in which they documented carrying out chemical reactions using microwave energy, and it was in 1986 that the first reports appeared in the scientific literature showing that microwave heating can be used in organic chemistry Since these early days, the use of microwave heating as a tool in preparative chemistry has transitioned from a curiosity to mainstream, both in industrial and academic settings Perhaps the main driving force behind this is the short reaction times that are often possible when using microwave heating Alongside this, chemists have found that product yields can improve The development of scientific microwave apparatus has been instrumental (quite literally) in the advance of the field There is now a range of equipment available for performing chemistry on milligrams as well as kilograms of material Advantages over domestic microwave ovens include accurate measurement of parameters such as temperature and pressure as well as, most importantly, safety Household microwaves are great for heating food but are not designed for synthetic chemistry, as many of us who started out working with them found out firsthand Alongside the development of microwave heating for preparative chemistry has come the somewhat controversial topic of “microwave effects.” In an attempt to rationalize the short reaction times and different product distributions observed when using microwave as opposed to “conventional heating,” a range of theories has been suggested, some of which, if true, would require rewriting the laws of science When comparisons are made under strictly identical conditions, the general observation is that, be it in a microwave or an oil bath, heating is just that—heating However, the operational ease with which reactions can be performed makes microwave heating a very valuable addition to any preparative chemistry laboratory No longer you have to work in high boiling point solvents with messy oil baths and lengthy reaction times in order to obtain high yields of your target molecule This book will showcase the application of microwave heating in a number of areas of preparative chemistry, a theme running through it being sustainability Looking at the online resource, Wikipedia, sustainability is defined as “the capacity to endure.” Within the chemistry community, sustainability is becoming front-andcenter as evidenced by the fact that at the end of 2009 two of the largest chemical societies, the American Chemical Society (ACS) and the Royal Society of Chemistry (RSC), agreed to collaborate to promote chemistry’s role in a sustainable world In addition, the topic for the Spring 2010 ACS National Meeting was “Chemistry for a Sustainable World.” So how then can microwave heating be used as a tool for sustainable chemistry? There are some clear-cut examples shown in this book: microwave heating for making biodegradable polymers and efficient battery materials, for ix 278 Z Zeolites, A, 218, β, 221, Manganese oxide, 218, 219, mixed-metal, 218, silicalite, 221, Y, 217, 221 Index