SSoonnoocchheemmiiccaall aanndd MMeecchhaannoocchheemmiiccaall AApppplliiccaattiioonnss iinn Organic Synthesis HHoovviigg KKoouuyyoouummddjjiiaann Wednesday, March 17, 2010 EEnneerrggyy ssoouurrcceess ooff cchheemmiiccaall rreeaaccttiioonnss MMiiccrroowwaavveess PPrreessssuurree HHeeaatt EElleeccttrriicciittyy https://www.kintera.com/accounttempfiles/account105257/images/heat_thermometer.jpg 2 http://www.mdpi.org/ecsoc/ecsoc‐6/Papers/E001/E001_files/208_files/Micro.gif http://wpcontent.answers.com/wikipedia/commons/thumb/3/39/ElectrochemCell.png/250px‐ElectrochemCell.png http://www.americanairworks.com/images/dial_a_pressure.gif UUllttrraassoouunndd:: AAlltteerrnnaattiivvee ssoouurrccee ooff eenneerrggyy • Nanomaterials • SSonoellecttrochhemiisttry • OOrrggaanniicc ssyynntthheessiiss • Glassware cleaning UUllttrraassoouunndd bbaatthhss http://www.bransonic.com/pdf/Bransonic%20Brochure.pdf 3 OOuuttlliinnee • Ultrasound (US) – DDeeffiinniittiioonn aanndd bbaacckkggrroouunndd • Cavitation phenomenon – Characteristics and influencing factors • A sample of sonochemical reactions in organic synthesis – Kornblum‐Russell reaction – HHeetteerroo‐MMiicchhaaeell rreeaaccttiioonn – Preparation of Grignard reagent – Suzuki coupling • Cavitation induced mechanochemistry – Cleavage of azo‐linkages – Reconfigguration of atroppisomers – Electrocyclic opening of benzocyclobutene 4 OOuuttlliinnee • Ultrasound (US) – DDeeffiinniittiioonn aanndd bbaacckkggrroouunndd • Cavitation phenomenon – Characteristics and influencing factors • A sample of sonochemical reactions in organic synthesis – Kornblum‐Russell reaction – HHeetteerroo‐MMiicchhaaeell rreeaaccttiioonn – Preparation of Grignard reagent – Suzuki coupling • Cavitation induced mechanochemistry – Cleavage of azo‐linkages – Reconfigguration of atroppisomers – Electrocyclic opening of benzocyclobutene 5 EElleeccttrroommaaggnneettiicc aanndd ssoouunndd ssppeeccttrruumm RRaaddiioo MMiiccrroowwaavveess IInnffrraarreedd UUllttrraavviioolleett XX‐‐rraayyss GGaammmmaa 33GGHHzz 33TTHHzz 443300TTHHzz 775500TTHHzz 330000PPHHzz 3300EEHHzz EEaarrtthhqquuaakkee mmoonniittoorriinngg HHuummaann ssppeeeecchh SSOONNAARR MMeeddiiccaall ddiiaaggnnoossiiss Low bass notes Animals Sonochemistry IInnffrraassoouunndd AAccoouussttiicc UUllttrraassoouunndd 20Hz 20KHz 2MHz 200MHz 6 DDeeffiinniittiioonn ooff ssoonnoocchheemmiissttrryy Sonochemistryy: A branch of chemical research dealingg with the chemical effects and applications of ultrasonic waves, that is, sound with frequencies above 20 kHz tthhatt lliie bbeyondd tthhe upper lliimiitt off hhuman hheariing. Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press, New York, 1998, pp. 1–19 7 BBeesstt kknnoowwnn uusseess ooff uullttrraassoouunndd • Target detection using SONAR ((SSOOuunndd NNAAvviiggaattiioonn aanndd RRaannggiinngg)) • Medical apppplications: – Medicalsonography (ultrasonography) – Acoustic targeted drug delivery – CClleeaanniinngg tteeeetthh iinn ddeennttaall hhyyggiieennee • Industrial Applications: – Ultrasonic testing (non‐destructive) – Ultrasonic cleaning http://www.personal.psu.edu/users/k/g/kgc5007/Project%203%20Active%20Sonar.gif http://www.advanceusa.org/blog/content/binary/Ultrasound%202.jpg 8 http://media.noria.com/sites/archive_images/Backup_200411_Tech‐Ultrasound1.jpg Ultrasound instruments for organic chhemiistry Cup‐horn sonicator Probe sonicator $$11,220000‐$$11,660000 $$22,330000‐$$55,000000 http://www.nano‐lab.com/ultrasonic‐probe‐dispersion‐equipment.html 9 UUllttrraassoouunndd rreeaaccttoorrss iinn pprroocceessss cchheemmiissttrryy UUIIPP1166000000 reactor Ultrasonic reactor http://www.hielscher.com/image/7xuip1000hd_flowcell_p0500.jpg 10 http://www.hielscher.com/image/uip1000_uip16000_p0500.jpg
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