Nontraditional Activation Methods in Green and Sustainable Applications: Microwaves; Ultrasounds; Photo-, Electro- and Mechanochemistry and High ... (Advances in Green and Sustainable Chemistry) PDF
Preview Nontraditional Activation Methods in Green and Sustainable Applications: Microwaves; Ultrasounds; Photo-, Electro- and Mechanochemistry and High ... (Advances in Green and Sustainable Chemistry)
NONTRADITIONAL ACTIVATION METHODS IN GREEN AND SUSTAINABLE APPLICATIONS Advances in Green and Sustainable Chemistry NONTRADITIONAL ACTIVATION METHODS IN GREEN AND SUSTAINABLE APPLICATIONS Microwaves; Ultrasounds; Photo-, Electro- and Mechanochemistry and High Hydrostatic Pressure Series Editor (cid:1) € € BELA TOROK Professor, University of Massachusetts Boston, Boston, MA, United States € CHRISTIAN SCHAFER Lecturer, University of Massachusetts Boston, Boston, MA, United States Elsevier Radarweg29,POBox211,1000AEAmsterdam,Netherlands TheBoulevard,LangfordLane,Kidlington,OxfordOX51GB,UnitedKingdom 50HampshireStreet,5thFloor,Cambridge,MA02139,UnitedStates ©2021ElsevierInc.Allrightsreserved. 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Practitionersandresearchersmustalwaysrelyontheirownexperienceandknowledgeinevaluating andusinganyinformation,methods,compounds,orexperimentsdescribedherein.Inusingsuch informationormethodstheyshouldbemindfuloftheirownsafetyandthesafetyofothers,including partiesforwhomtheyhaveaprofessionalresponsibility. Tothefullestextentofthelaw,neitherthePublishernortheauthors,contributors,oreditors,assume anyliabilityforanyinjuryand/ordamagetopersonsorpropertyasamatterofproductsliability, negligenceorotherwise,orfromanyuseoroperationofanymethods,products,instructions,orideas containedinthematerialherein. LibraryofCongressCataloging-in-PublicationData AcatalogrecordforthisbookisavailablefromtheLibraryofCongress BritishLibraryCataloguing-in-PublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary ISBN:978-0-12-819009-8 ForinformationonallElsevierpublications visitourwebsiteathttps://www.elsevier.com/books-and-journals Publisher:SusanDennis AcquisitionsEditor:AnnekaHess EditorialProjectManager:LenaSparks ProductionProjectManager:DebasishGhosh CoverDesigner:AlanStudholme TypesetbySPiGlobal,India Contributors RicardoBelloso DepartmentofChemistry,GeorgiaSouthernUniversity,Statesboro,GA,UnitedStates ClarenceCharnay ICGM,UnivMontpellier,CNRS,ENSCM,Montpellier,France PedroCintas DepartmentofOrganicandInorganicChemistry,FacultyofSciencesandIACYS-GreenChemistry andSustainableDevelopmentUnit,UniversityofExtremadura,Badajoz,Spain EvelinaColacino ICGM,UnivMontpellier,CNRS,ENSCM,Montpellier,France GiancarloCravotto DepartmentofDrugScienceandTechnology,andNIS-CentreforNanostructuredInterfacesandSurfaces, UniversityofTurin,Turin,Italy FrancescoDelogu DipartimentodiIngegneriaMeccanica,Chimica,edeiMateriali,Universita`degliStudidiCagliari,Cagliari, Italy FranziskaEmmerling BAMFederalInstituteforMaterialsResearchandTesting,Berlin,Germany SatoshiFujii DepartmentofInformationandCommunicationSystemEngineering,OkinawaCollege,Okinawa,Japan AharonGedanken DepartmentofChemistry,BarIlanUniversity,RamatGan,Israel AllenGordon DepartmentofChemistryandBiochemistry,GeorgiaSouthernUniversity,Statesboro,GA,UnitedStates NorbertHoffmann CNRS,Universit(cid:1)edeReimsChampagne-Ardenne,ICMR,EquipedePhotochimie,UFRSciences, Reims,France Istva´nJablonkai MTATTKLendu¨letFunctionalOrganicMaterialsResearchGroup,InstituteofOrganicChemistry,Research CentreforNaturalSciences,Budapest,Hungary AnkeKabelitz BAMFederalInstituteforMaterialsResearchandTesting,Berlin,Germany AttilaKunfi MTATTKLendu¨letFunctionalOrganicMaterialsResearchGroup,InstituteofOrganicChemistry,Research CentreforNaturalSciences,Budapest,Hungary ShainazLandge DepartmentofChemistryandBiochemistry,GeorgiaSouthernUniversity,Statesboro,GA,UnitedStates CorentinLefebvre CNRS,Universit(cid:1)edeReimsChampagne-Ardenne,ICMR,EquipedePhotochimie,UFRSciences, Reims,France xi xii Contributors Ga´borLondon MTATTKLendu¨letFunctionalOrganicMaterialsResearchGroup,InstituteofOrganicChemistry,Research CentreforNaturalSciences,Budapest,Hungary KatiaMartina DepartmentofDrugScienceandTechnology,andNIS-CentreforNanostructuredInterfacesandSurfaces, UniversityofTurin,Turin,Italy AdamA.L.Michalchuk BAMFederalInstituteforMaterialsResearchandTesting,Berlin,Germany ManishaMishra DepartmentofChemistry,UniversityofMassachusettsBoston,Boston,MA,UnitedStates TaraMooney DepartmentofChemistry,UniversityofMassachusettsBoston,Boston,MA,UnitedStates MariaJesusMoran DepartmentofDrugScienceandTechnology,andNIS-CentreforNanostructuredInterfacesandSurfaces, UniversityofTurin,Turin,Italy BilalNi¸sancı DepartmentofChemistry,FacultyofScience,Atatu€rkUniversity,Erzurum,Turkey Istva´nPa´linko´ UniversityofSzeged,Szeged,Hungary AndreaPorcheddu DipartimentodiScienzeChimicheeGeologiche,Universita`degliStudidiCagliari,CittadellaUniversitaria, Monserrato,CA,Italy IndraNeelPulidindi DepartmentofChemistry,BarIlanUniversity,RamatGan,Israel Da-HuiQu KeyLaboratoryforAdvancedMaterials,SchoolofChemistryandMolecularEngineering,EastChina UniversityofScienceandTechnology,Shanghai,China ChristianSch€afer DepartmentofChemistry,UniversityofMassachusettsBoston,Boston,MA,UnitedStates AbidShaikh DepartmentofChemistry,GeorgiaSouthernUniversity,Statesboro,GA,UnitedStates Pa´lSipos UniversityofSzeged,Szeged,Hungary Ma´rtonSzabados UniversityofSzeged,Szeged,Hungary B(cid:1)elaTo€ro€k DepartmentofChemistry,UniversityofMassachusettsBoston,Boston,MA,UnitedStates ShuntaroTsubaki SchoolofMaterialsandChemicalTechnology,TokyoInstituteofTechnology,Yokohama,Japan Ga´borVarga UniversityofSzeged,Szeged,Hungary Contributors xiii YujiWada InstituteofInnovationResearch,TokyoInstituteofTechnology,Yokohama;MicrowaveChemicalCo.Ltd., TechnoAlliance3F,Suita,Osaka,Japan KazutakaYamamoto HeadofLaboratory,FoodProcessEngineering,DivisionofFoodProcessingandDistribution,FoodResearch Institute,NationalAgricultureandFoodResearchOrganization,Tsukuba,Ibaraki,Japan CHAPTER ONE Application of nontraditional activation methods in green and sustainable chemistry: Microwaves, ultrasounds, electro-, photo-, and mechanochemistry, and high hydrostatic pressure Christian Sch€afer and Be(cid:2)la To€ro€k DepartmentofChemistry,UniversityofMassachusettsBoston,Boston,MA,UnitedStates 1 Introduction Many discoveries made in chemistry in the 20th century enabled strong developments in the preparation of a broad range of products. The developingchemicalindustrywasmostlybasedonpetroleumresourcesthat provided a steady flow of raw materials. The continuous development of new fields such as medicinal chemistry, polymers and plastics, agrochemi- cals, and the likes resulted in booming industrial production. Although the new products had a largely positive impact on the society as a whole, several unintended issues began to appear. These included industrial disas- ters, drug side effects, and the damage caused to Earth’s protective ozone layer among many others. These incidents made the society realize the potential harmful effects of large-scale production and the associated waste producedbyit,someproductsthemselves,andtheinabilityoftheseproducts todecomposeattheendoftheirlifecycle.Inaddition,theextensiveuseof fossil fuels for energy production and petroleum derivatives for industrial feedstockresultedinissuesthatcanfurtherthreatentheplanet’secosystem. While there have been corrective measures implemented along the way in theformsofgovernmentregulations,aconcentratedeffortinthelate1990s resultedinthebirthoftheGreenChemistrymovement1toaddressthefun- damentalnatureoftheproblems.Infact,thecurrenteffortsoftenappearto bejointventuresbygovernment,academia,andindustrysuggestingamuch NontraditionalActivationMethodsinGreenandSustainableApplications ©2021ElsevierInc. 1 https://doi.org/10.1016/B978-0-12-819009-8.00016-5 Allrightsreserved. 2 ChristianSch€aferandB(cid:2)elaTo€ro€k more effective tackling of the problems than when these entities were activelyworkingagainsteachotherdelayingthedevelopmentofactualsolu- tions. This ongoing partnership ensures the continuous expansion and advancement of environmentally friendly processes and products,2–4 and green chemistry and environmental science made steady developments in the general science education as well.5–7 There are many ways chemistry cancontributetotheseadvances,replacingoldoutdatedchemicalprocesses with ones having less environmental impact, traditional petroleum based rawmaterialswithsustainableones,ornotoriouslystableconventionalplas- tics and other chemicals with biodegradable alternatives. Thisintroductorychapterandtheentirebookfocusonaspecialtoolset that is a great contributor to the development of green synthetic methods; the so-called nontraditional activation methods that use alternative energy forms to conventional convective heating to initiate chemical reactions. A large majority of chemical reactions require activation energy in order to occur. Traditionally this energy was introduced to a reaction as heat mostlyviaconvectiveheatingusinganexternalheatsource.Althougheffec- tive,convectiveheatingisslowandessentiallydependentonheatdiffusion (mixing)inthesystem.Anotherproblemisthatthetemperatureofthewall ofthereactionvesseliscommonly10–20°Chigherthanthatinthecenterof the liquid, often causing side reactions or decomposition on or around the surfaceofthewall.Toalleviatetheseissues,severalnontraditionalactivation methods have been developed. Although different in nature, the common featureofthesemethodsisthattheyarebasedonthedirectenergytransferin the reaction mixture. In this chapter, we will only attempt to describe the basic features of these methods, such as microwave- and ultrasonic irradia- tion,photo-,electro-andmechanochemistryandhighhydrostaticpressure withafewrepresentativeexamples,whichwillbefollowedbystate-of-the- art specific applications in the upcoming chapters. 2 Microwave-assisted organic synthesis Thefirstobservationsofthemicrowaveheatingeffectoccurredinthe 1940s when the magnetron, now the common microwave source, was appliedduringthedevelopmentoftheRADAR.Followingupontheorig- inal discovery the application of microwave ovens in the food and airline industry began in the 1950s.8 Although the first synthetic application in 19699 largely went unnoticed, the independent publication of microwave-activated synthetic applications by two teams, Gedye et al.10 Applicationofnontraditionalactivationmethods 3 and Giguere et al.11 initiated an exponential development of microwave- assisted synthesis. Since then microwave-assisted organic synthesis (MAOS) has become a household name in laboratories, with thousands ofpaperspublishedinthisarea.Thecontemporarymicrowaveinstruments and reactors provide the essential elements that are required in synthetic chemistry, such as temperature control, reliability, reproducibility, and in special cases, scalability. The theories of how microwaves interact with materialshavebeenasubjectofasometimesintensedebate12–14andnumer- ousreports,andreviews.15–17Here,weonlyfocusonthebasicinformation related to this issue. Thefrequencyrangeformicrowaveradiationisbetween1and300GHz appearing in the relatively low energy region of the electromagnetic spec- trum.Microwavespossesslowerenergythaninfraredirradiation,buthigher than radio waves. Given their limited energy, microwave irradiation is not able to excite electron transitions, break chemical bonds, or even activate changes within individual molecules such as vibration. The rotational motion of molecules is the physical phenomenon that microwave energy can excite to generate internal heat formation. This entails that the micro- waveeffectislimited toliquids andsolids.Although,gaseous materialscan absorbmicrowaves,duetothelimitedinteractionbetweenthemoleculesit doesnotgenerateheat,ratherresultsinsharppeaksinafingerprintfashion, which is the foundation of microwave spectroscopy. In more dense mate- rials, the rotating molecules will collide with each other, and due to the restricted movement, dielectric polarization will occur, which is the major source of microwave heating. Particularly two features, the dielectric con- stant (ε0) and dielectric loss (ε00), and their ratio, the so-called loss tangent delta (tgδ¼ε00/ε0) are important to determine how a certain compound or material is able to convert the microwave irradiation to heat. Materials of significant dipole moments (polar solvents, salts, ionic liquids, certain metal oxides, etc.) are the best media for microwave-assisted chemistry. Nonpolar materials (hydrocarbons and most plastics) are weak microwave absorbers(orcompletelytransparent)andthusdonotgenerateinternalheat formation. Although the application of microwave irradiation as an activation method carries multiple benefits, the major advantages are rapid reactions, and therefore significantly reduced reaction times. This could be quitesig- nificant; in our experience for example, the condensation of trifluoroacetophenones with a variety of benzylamines require 168h (1week!)heatingat130°C,whilethesamereactionheatedbymicrowaves
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