Ball Milling Towards Green Synthesis Applications, Projects, Challenges 1 0 0 P F 0- 8 9 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: d g | 9. c.or 07:1bs.rs 2014 23:http://pu 1/n 1o n 26/2014 d oer eb dm nloaove wN Do26 n o d e h s bli u P View Online RSC Green Chemistry Editor-in-Chief: Professor James Clark, Department of Chemistry, University of York, UK 1 0 0 P F 0- Series Editors: 8 19 Professor George A Kraus, Department of Chemistry, Iowa State University, 2 26 Ames, Iowa, USA 8 17 ProfessorAndrzejStankiewicz,DelftUniversityofTechnology,TheNetherlands 8 97 Professor Peter Siedl, Federal University of Rio de Janeiro, Brazil 9/ 3 Professor Yuan Kou, Peking University, China 0 1 0. 1 oi: Titles in the Series: d g | 1: The Future of Glycerol: New Uses of a Versatile Raw Material 9. c.or 2: Alternative Solvents for Green Chemistry 07:1bs.rs 3: Eco-Friendly Synthesis of Fine Chemicals 2014 23:http://pu 45:: SCuhsetmaiincaabllReeSaocltuiotinosnasnfdorPMroocdeesrsnesEucnodneormFileosw Conditions 1/n 6: Radical Reactions in Aqueous Media 1o d on 26/er 2014 78:: ATqhueeFouutsurMeiocrfoGwlaycveerColh:e2mndisEtrdyition eb 9: Transportation Biofuels: Novel Pathways for the Production of Ethanol, dm nloaove Biogas and Biodiesel Dow26 N 10: Alternatives to Conventional Food Processing n 11: Green Trends in Insect Control o d 12: A Handbook of Applied Biopolymer Technology: Synthesis, Degradation e h s and Applications bli u 13: Challenges in Green Analytical Chemistry P 14: Advanced Oil Crop Biorefineries 15: Enantioselective Homogeneous Supported Catalysis 16: Natural Polymers Volume 1: Composites 17: Natural Polymers Volume 2: Nanocomposites 18: Integrated Forest Biorefineries 19: Sustainable Preparation of Metal Nanoparticles: Methods and Applications 20: Alternative Solvents for Green Chemistry: 2nd Edition 21: Natural Product Extraction: Principles and Applications 22: Element Recovery and Sustainability 23: Green Materials for Sustainable Water Remediation and Treatment 24: The Economic Utilisation of Food Co-Products 25:BiomassforSustainableApplications:PollutionRemediationandEnergy 26: From C-H to C-C Bonds: Cross-Dehydrogenative-Coupling 27: Renewable Resources for Biorefineries View Online 28: Transition Metal Catalysis in Aerobic Alcohol Oxidation 29: Green Materials from Plant Oils 30: Polyhydroxyalkanoates (PHAs) Based Blends, Composites and Nanocomposites 1 0 31:BallMillingTowardsGreenSynthesis:Applications,Projects,Challenges 0 P F 0- 8 9 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: d g | 9. c.or 07:1bs.rs 2014 23:http://pu 1/n 1o n 26/2014 d oer eb dm nloaove wN Do26 n o d e h s bli u P How to obtain future titles on publication: Astandingorderplanisavailableforthisseries.Astandingorderwillbring delivery of each new volume immediately on publication. For further information please contact: BookSalesDepartment,RoyalSocietyofChemistry,ThomasGrahamHouse, Science Park, Milton Road, Cambridge, CB4 0WF, UK Telephone: þ44 (0)1223 420066, Fax: þ44 (0)1223 420247 Email: [email protected] Visit our website at www.rsc.org/books View Online 1 0 0 P F 0- 8 9 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: d g | 9. c.or 07:1bs.rs 2014 23:http://pu 1/n 1o n 26/2014 d oer eb dm nloaove wN Do26 n o d e h s bli u P View Online Ball Milling Towards Green Synthesis 1 0 Applications, Projects, Challenges 0 P F 0- 8 9 1 2 6 2 8 7 1 8 7 Edited by 9 9/ 3 0 1 0. Brindaban Ranu 1 oi: University of Jadavpur, Jadavpur, Kolkata, India d g | Email: [email protected] 9. c.or 07:1bs.rs Achim Stolle 2014 23:http://pu UEmniavielr:saitcyhiomf.Jsetnoall,eJ@enuan,i-Gjeenrma.adney 1/n 1o n 26/2014 d oer eb dm nloaove wN Do26 n o d e h s bli u P View Online 1 0 0 P F 0- 8 9 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: d g | 9. c.or 07:1bs.rs RSCGreenChemistryNo.31 2014 23:http://pu PPrDinFteIISSBBNN::997788--11--8748927632--914958--00 11/on ISSN:1757-7039 d on 26/er 2014 AcataloguerecordforthisbookisavailablefromtheBritishLibrary eb dm nloaove rTheRoyalSocietyofChemistry2015 wN Do26 Allrightsreserved n o d Apartfromfairdealingforthepurposesofresearchfornon-commercialpurposesorfor e h s privatestudy,criticismorreview,aspermittedundertheCopyright,DesignsandPatents ubli Act1988andtheCopyrightandRelatedRightsRegulations2003,thispublicationmaynot P bereproduced,storedortransmitted,inanyformorbyanymeans,withouttheprior permissioninwritingofTheRoyalSocietyofChemistryorthecopyrightowner,orinthe caseofreproductioninaccordancewiththetermsoflicencesissuedbytheCopyright LicensingAgencyintheUK,orinaccordancewiththetermsofthelicencesissuedbythe appropriateReproductionRightsOrganizationoutsidetheUK.Enquiriesconcerning reproductionoutsidethetermsstatedhereshouldbesenttoTheRoyalSocietyof Chemistryattheaddressprintedonthispage. TheRSCisnotresponsibleforindividualopinionsexpressedinthiswork. Theauthorshavesoughttolocateownersofallreproducedmaterialnotintheirown possessionandtrustthatnocopyrightshavebeeninadvertentlyinfringed. PublishedbyTheRoyalSocietyofChemistry, ThomasGrahamHouse,SciencePark,MiltonRoad, CambridgeCB40WF,UK RegisteredCharityNumber207890 Forfurtherinformationseeourwebsiteatwww.rsc.org 7 0 0 P F 0- 8 9 Foreword 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: Ball milling creates stress on substances. Solids break, and the resulting d g | particles are modified in shape and size. Defects are induced and surface 6. c.or areas enlarged. Consequently, ball milling is highly relevant for various 08:0bs.rs technological fields including mineral processing, materials engineering, 2014 23:http://pu aimsneducshbeaidonmifcoaarlssatrdepeaagtrmrtaicedlnaettishoinazes. Iornethdmeuroctseitffoonefc.tsHsuoacshwewavpeelprl,.liOcthanteiotehnnesemrtghoyeleimncudillulaicnregldepvbreoyl,ctefhosesr 1/n n 26/12014 o epxraomdupcltes, wthitehaarrltaenrgedempernotpserotfiecsh.eTmheicaplotsetnruticatluroefsscuacnhcmheacnhgaenloecahdeimngictaol d oer approaches and the implications in utilizing them in modern organic syn- eb dm wnloaNove tbhoeoskisedariteednibcyelSytoilllluesatnradteRdanbuy.tMheaneyxcoefltlehnetdcisocnutsrisbeudtiroenacsticoonllseacrteedsoilnvetnhte- Do26 free leading to ecological and economical advantages over existing tech- n o nologiesprovidingthesameproducts.Furtherbenefitsarerecognizedwhen d he comparingtheenergyefficiencyofballmillingwithotheractivationmodes. s bli Apparently, ball milling can be applied in a number of bond-forming pro- u P cesses, and various standard organic transformations (such as oxidations, reductions, and peptide formations) benefit from the use of this mechano- chemical technique. Both low-molecular-weight compounds as well as polymers undergo specific chemical modifications in ball mills. Surprising observations have been made in both metal-catalyzed and organocatalytic C–C-bondformationsincludingasymmetricversionsthereof.Liquid-assisted grinding and kneading have proven advantageous for the preparation of co- ordination compounds. Being aware of the technological and process para- metersisessentialforachievingoptimalresultsinsynthetictransformations performed in ball mills. Although mechanochemical activations have already been utilized for a longtime,theadvantagesofapplyingballmillsintargetedorganicsynthesis RSCGreenChemistryNo.31 BallMillingTowardsGreenSynthesis:Applications,Projects,Challenges EditedbyBrindabanRanuandAchimStolle rTheRoyalSocietyofChemistry2015 PublishedbytheRoyalSocietyofChemistry,www.rsc.org vii View Online viii Foreword haslargelyremainedunrecognizeduntilrecently.Thegrowingawarenessof environmental implications of chemical processes and the search for greener solutions have led to a change, and today ball milling results are morepresentinthecommunity thanever.Gainingadeeperunderstanding 7 0 of the underlying mechanistic principles leading to mechanochemical acti- 0 P F vations and finding new reaction pathways resulting in products inacces- 0- 8 sible by other means will further expand the synthetic ball milling 9 1 2 opportunities. 6 2 8 This book will initiate new thought processes and promote the imple- 7 1 8 mentation of ball milling as a modern synthetic technique in existing lab 7 9 9/ structures. Experts in academia and industry as well as interested new- 3 10 comers will benefit from the timely presentations collected by Stolle and 0. 1 Ranu, and I congratulate both editors and authors for their stimulating oi: d contributions. g | 08:06. bs.rsc.or AachCeanr,stGeenrmBoalnmy 2014 23:http://pu 1/n 1o n 26/2014 d oer eb dm nloaove wN Do26 n o d e h s bli u P 9 0 0 P F 0- 8 9 Preface 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: During the last few years ball milling has emerged as a powerful tool in d g | effectingvariouschemicalreactionsinarelativelygreenwaybyreducingthe 9. c.or amount of solvent and operating at close to ambient temperature by appli- 08:1bs.rs cation ofmechanical energy.However,comparedto other alternative forms 2014 23:http://pu oacosfmeanpseayrnrgatythisveuetcilcyhtsaomsoamlltliocnrauomwwabidveeerasonefcdgtriuoolnutrpaossf.ocTuhhneudms,,ibstahtslelamonbidjleliacntcgitvieivsiotsyftiitlshlinlsiombtoiftoaemkdiitsloiatoar 1/n n 26/12014 o ctrraenastefoarmgaetnioernaslaamwaornegneasllssoefcttihoeniomfproeratdaenrcseinocflubdalilngmsiltluindgenitns,ctheeamchiecrasl d oer and researchers. This book, entitled Ball Milling Towards Green Synthesis: eb dm wnloaNove Aapppplliiccaattiioonns,oPfrbojaelcltsm, iCllhinagllefnogresv,acrioovuesrschtheemcicuarlretnratndsefovremloaptmioennstssuinchthaes Do26 carbon–carbon and carbon–heteroatom bond formation, oxidation– n o reduction, organocatalytic reaction, dehydrogenative coupling, synthesis of d he peptide, polymeric materials, etc. highlighting its green aspects, scope and s bli future prospects. This book also includes a chapter describing its origin, u P technological background and challenges. We gratefully acknowledge the co-operation from all those eminent and activescientistswhocontributedchapterstothisbookandthesupportand guidance from the staff at the Royal Society of Chemistry. Wehopethisbookwillbeabletoprovidebasicinformationregardingball millinganditsapplicationinchemicalsynthesisandthuswillbeusefultoa widesectionofchemistsincludingstudentsandresearchersassociatedwith academy and industry. Brindaban C. Ranu Achim Stolle RSCGreenChemistryNo.31 BallMillingTowardsGreenSynthesis:Applications,Projects,Challenges EditedbyBrindabanRanuandAchimStolle rTheRoyalSocietyofChemistry2015 PublishedbytheRoyalSocietyofChemistry,www.rsc.org ix View Online 9 0 0 P F 0- 8 9 1 2 6 2 8 7 1 8 7 9 9/ 3 0 1 0. 1 oi: d g | 9. c.or 08:1bs.rs 2014 23:http://pu 1/n 1o n 26/2014 d oer eb dm nloaove wN Do26 n o d e h s bli u P