CoFe2O4 nanoparticles: An efficient heterogeneous magnetically separable catalyst for “click” synthesis of arylidene barbituric acid derivatives at room temperature

CoFe2O4 nanoparticles: An efficient heterogeneous magnetically separable catalyst for “click” synthesis of arylidene barbituric acid derivatives at room temperature

Š‹‡•‡ ‘—”ƒŽ‘ˆƒ–ƒŽ›•‹•͵ͶȋʹͲͳ͵Ȍͳ͸ͻ͹Ȃͳ͹ͲͶ   availableatwww.sciencedirect.com  journalhomepage:www.elsevier.com/locate/chnjc...
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Š‹‡•‡ ‘—”ƒŽ‘ˆƒ–ƒŽ›•‹•͵ͶȋʹͲͳ͵Ȍͳ͸ͻ͹Ȃͳ͹ͲͶ 



availableatwww.sciencedirect.com



journalhomepage:www.elsevier.com/locate/chnjc





Article 

CoFe2O4nanoparticles:Anefficientheterogeneousmagnetically separablecatalystfor“click”synthesisofarylidenebarbituricacid derivativesatroomtemperature

ƒ•’”‡‡–ƒ—”ƒŒ’—–ȗǡ ƒ‰ƒ†‡‡’ƒ—” DepartmentofChemistry,Dr.B.R.AmbedkarNationalInstituteofTechnology,Jalandhar144011,India

         



Articlehistory: ‡…‡‹˜‡†ͻƒ›ʹͲͳ͵ ……‡’–‡†ͷ —‡ʹͲͳ͵ —„Ž‹•Š‡†ʹͲ‡’–‡„‡”ʹͲͳ͵ Keywords: ƒ‰‡–‹…ƒŽŽ›•‡’ƒ”ƒ„Ž‡…ƒ–ƒŽ›•– ”›Ž‹†‡‡„ƒ”„‹–—”‹…ƒ…‹††‡”‹˜ƒ–‹˜‡ “—‡‘—•‡–Šƒ‘Ž —’‡”’ƒ”ƒƒ‰‡–‹…‘ ‡ʹͶ    ƒ‘’ƒ”–‹…Ž‡ ‡–‡”‘‰‡‡‘—•…ƒ–ƒŽ›•–

       



…‘’”‡…‹’‹–ƒ–‹‘‡–Š‘†™ƒ•—•‡†–‘•›–Š‡•‹œ‡•—’‡”’ƒ”ƒƒ‰‡–‹…‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•™‹–ŠǦ ‘—– —•‹‰ ƒ› …ƒ’’‹‰ ƒ‰‡–•Ȁ•—”ˆƒ…–ƒ–•Ǥ Š‡ ’”‡’ƒ”‡† ƒ‘’ƒ”–‹…Ž‡• ™‡”‡ …Šƒ”ƒ…–‡”‹œ‡† —•‹‰ ‘—”‹‡” –”ƒ•ˆ‘” ‹ˆ”ƒ”‡† •’‡…–”‘•…‘’›ǡ •…ƒ‹‰ ‡Ž‡…–”‘ ‹…”‘•…‘’›ǡ –”ƒ•‹••‹‘ ‡Ž‡…–”‘ ‹…”‘•…‘’›ǡǦ”ƒ›†‹ˆˆ”ƒ…–‹‘ǡƒ˜‹„”ƒ–‹‰•ƒ’Ž‡ƒ‰‡–‘‡–‡”ȋȌǡʹƒ†•‘”’–‹‘ƒ†–Š‡”‘Ǧ ‰”ƒ˜‹‡–”‹…Ȁ†‹ˆˆ‡”‡–‹ƒŽ –Š‡”ƒŽ ƒƒŽ›•‹•Ȁ†‹ˆˆ‡”‡–‹ƒŽ –Š‡”ƒŽ ‰”ƒ˜‹‡–”› –‡…Š‹“—‡•Ǥ Š‡ •›–Š‡Ǧ •‹œ‡†•’‹‡Ž‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Šƒ†ƒƒ˜‡”ƒ‰‡•‹œ‡‘ˆʹȂͺ™‹–ŠƒŠ‹‰Š•—”ˆƒ…‡ƒ”‡ƒȋͳͶͲǤͻ ʹȀ‰ȌǤ Š‡ ˆ‹‡Ž†Ǧ†‡’‡†‡– ƒ‰‡–‹œƒ–‹‘ǡ †‡‘•–”ƒ–‡† „›  ƒ† •ƒ–—”ƒ–‹‘ ƒ‰‡–‹œƒ–‹‘ǡ ™ƒ•ˆ‘—†–‘„‡ͳǤ͹͹‡—Ȁ‰Ǥ‡ˆˆ‹…‹‡–‡–Š‘†™ƒ•—•‡†ˆ‘”–Š‡•›–Š‡•‹•‘ˆƒ”›Ž‹†‡‡„ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡• —•‹‰ ‘ ‡ʹͶ ƒ‰‡–‹… ƒ‘’ƒ”–‹…Ž‡• ƒ• ƒ ƒ‰‡–‹…ƒŽŽ› •‡’ƒ”ƒ„Ž‡ ƒ† ”‡—•ƒ„Ž‡ …ƒ–ƒŽ›•–‹ƒ“—‡‘—•‡–Šƒ‘ŽǤŠ‡ƒ––”ƒ…–‹˜‡ˆ‡ƒ–—”‡•‘ˆ–Š‹••›–Š‡–‹…’”‘–‘…‘Ž™‡”‡˜‡”›•Š‘”–”‡ƒ…Ǧ –‹‘–‹‡ǡŠ‹‰Š›‹‡Ž†•ǡŠ‹‰Š–—”‘˜‡”ˆ”‡“—‡…›ǡ•‹’Ž‡™‘”Ǧ—’’”‘…‡†—”‡ǡ‡…‘‘›ǡƒ…Ž‡ƒ”‡ƒ…Ǧ –‹‘‡–Š‘†‘Ž‘‰›ǡƒ†…Š‡‘•‡Ž‡…–‹˜‹–›ǡƒ•™‡ŽŽƒ•’”‘˜‹•‹‘‘ˆƒ‡…‘ˆ”‹‡†Ž›ƒ†‰”‡‡•›–Š‡•‹•Ǥ ̹ʹͲͳ͵ǡƒŽ‹ƒ •–‹–—–‡‘ˆŠ‡‹…ƒŽŠ›•‹…•ǡŠ‹‡•‡…ƒ†‡›‘ˆ…‹‡…‡•Ǥ —„Ž‹•Š‡†„›Ž•‡˜‹‡”ǤǤŽŽ”‹‰Š–•”‡•‡”˜‡†Ǥ

 1.  Introduction Š‡ ƒ‹ ‰‘ƒŽ ‹ –Š‡ ˆ‹‡Ž† ‘ˆ …ƒ–ƒŽ›•‹•ǡ ‹ –‡”• ‘ˆ ‰”‡‡ …Š‡‹•–”›ǡ ‹• –‘ †‡˜‡Ž‘’ ‡˜‹”‘‡–ƒŽŽ› „‡‹‰ǡ ’”ƒ…–‹…ƒŽǡ …Ž‡ƒǡ ‡…‘‘‹…ƒŽǡ ƒ† ‡ˆˆ‹…‹‡– ’”‘…‡••‡• ˆ‘” …ƒ–ƒŽ›•– •‡’ƒ”ƒǦ –‹‘ ƒ† ”‡…›…Ž‹‰ ȏͳȐǤ  ’‘••‹„Ž‡ ™ƒ› ‘ˆ ƒ…Š‹‡˜‹‰ –Š‹• ‹• –Š‡ —•‡ ‘ˆ ƒ‰‡–‹… …ƒ–ƒŽ›•– •›•–‡• ˆ‘” ˜ƒ”‹‘—• ‘”‰ƒ‹… –”ƒ•ˆ‘”Ǧ ƒ–‹‘•Ǥ  ƒ‰‡–‹… …ƒ–ƒŽ›•– •›•–‡ ’”‘˜‹†‡• ‘”‡ ‡ˆˆ‡…–‹˜‡ •‡’ƒ”ƒ–‹‘‘ˆ–Š‡…ƒ–ƒŽ›•––Šƒ†‘–”ƒ†‹–‹‘ƒŽˆ‹Ž–”ƒ–‹‘ƒ†…‡Ǧ –”‹ˆ—‰ƒ–‹‘‡–Š‘†•ƒ•‹–ƒ˜‘‹†•…ƒ–ƒŽ›•–Ž‘••ȏʹȐǤ —”–Š‡”‘”‡ǡ ƒ‰‡–‹… •‡’ƒ”ƒ–‹‘ ‹• ‡…‘‘‹…ƒŽǡ •‹’Ž‡ǡ ƒ† ’”‘‹•‹‰ ˆ‘” ‹†—•–”‹ƒŽƒ’’Ž‹…ƒ–‹‘ȏ͵ȂͷȐǤ ”‡…‡–›‡ƒ”•ǡƒ‰‡–‹…ƒ‘’ƒ”Ǧ –‹…Ž‡•Šƒ˜‡ƒ––”ƒ…–‡†™‘”Ž†™‹†‡ƒ––‡–‹‘ƒ•‡ˆˆ‹…‹‡–ǡ‡…‘‘Ǧ ‹…ƒŽǡ ‡˜‹”‘‡–ƒŽŽ› ˆ”‹‡†Ž›ǡ ƒ† ”‡…›…Žƒ„Ž‡ …ƒ–ƒŽ›•–• ȏ͸ȂͳͶȐǤ ƒ‰‡–‹…ƒ‘’ƒ”–‹…Ž‡•ƒ”‡ƒŽ•‘—•‡†ƒ•ƒŽ–‡”ƒ–‹˜‡•–‘…‘˜‡Ǧ

–‹‘ƒŽŠ‡–‡”‘‰‡‡‘—••—’’‘”–•Ǥ –Š‹•…‘–‡š–ǡƒ‰‡–‹…ˆ‡””‹–‡ ƒ‘’ƒ”–‹…Ž‡• •—…Š ƒ• …‘„ƒŽ– ˆ‡””‹–‡ ƒ‘’ƒ”–‹…Ž‡• Šƒ˜‡ „‡‡ —•‡† ƒ• ƒ‰‡–‹…ƒŽŽ› •‡’ƒ”ƒ„Ž‡ …ƒ–ƒŽ›•–• „‡…ƒ—•‡ –Š‡› Šƒ˜‡ Š‹‰Š–Š‡”ƒŽ•–ƒ„‹Ž‹–›ǡŽƒ”‰‡ƒ‰‡–‹…ƒ‹•‘–”‘’‹‡•ǡŠ‹‰Š•—”ˆƒ…‡ ƒ”‡ƒ•ǡ ‘†‡”ƒ–‡ •ƒ–—”ƒ–‹‘ ƒ‰‡–‹œƒ–‹‘•ǡ ƒ† …Š‡‹…ƒŽ •–ƒǦ „‹Ž‹–›ȏͳͷǡͳ͸ȐǢ–Š‡‹”…ƒ–ƒŽ›–‹…’”‘’‡”–‹‡•†‡’‡†‘–Š‡–‡–”ƒŠ‡Ǧ †”ƒŽ ƒ† ‘…–ƒŠ‡†”ƒŽ •‹–‡• ‘ˆ –Š‡ •’‹‡Ž •–”—…–—”‡ ‘ˆ ˆ‡””‹–‡ ƒǦ ‘’ƒ”–‹…Ž‡•Ǥ ƒ”‹‘—• ‡–Š‘†• Šƒ˜‡ „‡‡ ”‡’‘”–‡† ˆ‘” –Š‡ •›Ǧ –Š‡•‹• ‘ˆ …‘„ƒŽ– ˆ‡””‹–‡ ƒ‘’ƒ”–‹…Ž‡•ǡ •—…Š ƒ• •‘‘…Š‡‹…ƒŽ ȏͳ͹Ȑǡ ‹…”‘‡—Ž•‹‘ ȏͳͺȐǡ ‡…Šƒ‘…Š‡‹…ƒŽ ȏͳͻȐǡ ƒ† …‘Ǧ ’”‡…‹’‹–ƒ–‹‘ȏʹͲȂʹʹȐ‡–Š‘†•ǤŠ‡‘•–…‘‘Ž›—•‡† ƒ† ‡ˆˆ‡…–‹˜‡ ‡–Š‘† ‹• …‘’”‡…‹’‹–ƒ–‹‘ǡ ƒ• Ž‘™Ǧ–‡’‡”ƒ–—”‡ …‘Ǧ ’”‡…‹’‹–ƒ–‹‘’”‘˜‹†‡•Š‘‘‰‡‡‘—•ƒ†ˆ‹‡Ž›’‘™†‡”‡†ˆ‡”Ǧ ”‹–‡ ƒ‘’ƒ”–‹…Ž‡• ™‹–Š Š‹‰Š •—”ˆƒ…‡ ƒ”‡ƒ• ƒ† „‡––‡” …ƒ–ƒŽ›–‹… ƒ…–‹˜‹–›ȏʹ͵ȐǤ 

ȗ‘””‡•’‘†‹‰ƒ—–Š‘”Ǥ‡ŽǣΪͻͳǦͳͺͳǦʹ͸ͻͲ͵ͲͳǦͲʹš–ǣʹʹͲͺǢ ƒšǣΪͻͳǦͳͺͳǦʹ͸ͻͲ͵ʹͲǢǦƒ‹Žǣ”ƒŒ’—–Œ̷‹–ŒǤƒ…Ǥ‹  ǣͳͲǤͳͲͳ͸Ȁͳͺ͹ʹǦʹͲ͸͹ȋͳʹȌ͸Ͳ͸Ͷ͸ǦͻȁŠ––’ǣȀȀ™™™Ǥ•…‹‡…‡†‹”‡…–Ǥ…‘Ȁ•…‹‡…‡ȀŒ‘—”ƒŽȀͳͺ͹ʹʹͲ͸͹ȁŠ‹Ǥ Ǥƒ–ƒŽǤǡ‘ŽǤ͵Ͷǡ‘Ǥͻǡ‡’–‡„‡”ʹͲͳ͵ 



JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704

–Š‹••–—†›ǡ™‡†‡˜‡Ž‘’‡†ƒƒ‰‡–‹…ƒŽŽ›•‡’ƒ”ƒ„Ž‡ƒ‘Ǧ …ƒ–ƒŽ›•––Šƒ–‹••‹’Ž‡–‘’”‘†—…‡ǡ‰”‡‡ǡ‡ˆˆ‹…‹‡–ǡƒ†‹‡š’‡Ǧ •‹˜‡ƒ†‡šŠ‹„‹–•‡š…‡ŽŽ‡–…ƒ–ƒŽ›–‹…’‡”ˆ‘”ƒ…‡‹–Š‡•›–Š‡Ǧ •‹• ‘ˆ ƒ”›Ž‹†‡‡ „ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡•Ǥ Š‡ …ƒ–ƒŽ›•– ™ƒ• ‡ƒ•‹Ž› •‡’ƒ”ƒ–‡† ˆ”‘ –Š‡ ”‡ƒ…–‹‘ ‹š–—”‡ —•‹‰ ƒ ‡š–‡”ƒŽ ƒ‰‡– ƒ† ™ƒ• ”‡—•ƒ„Ž‡ ™‹–Š‘—– •‹‰‹ˆ‹…ƒ– Ž‘•• ‘ˆ …ƒ–ƒŽ›–‹… ƒ…–‹˜‹–›Ǥ ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡• ƒ”‡ ‘ˆ ‰”‡ƒ– ‹–‡”‡•– „‡…ƒ—•‡ ‘ˆ –Š‡‹”†‹˜‡”•‡„‹‘Ž‘‰‹…ƒŽƒ…–‹˜‹–›ǡ‡Ǥ‰Ǥǡƒ–‹„ƒ…–‡”‹ƒŽǡŠ›’‘–‡•‹˜‡ǡ ƒ‡•–Š‡–‹…ǡ ƒ–‹–—‘”ǡ ƒ† •‡†ƒ–‹˜‡ ‡ˆˆ‡…–• ȏʹͶȂʹ͸ȐǢ –Š‡› ƒ”‡ ƒŽ•‘—•‡†ƒ•‹–‡”‡†‹ƒ–‡•‹–Š‡•›–Š‡•‹•‘ˆ„‡œ›Ž„ƒ”„‹–—”‹… †‡”‹˜ƒ–‹˜‡• ȏʹ͹Ȑǡ Š‡–‡”‘…›…Ž‹… …‘’‘—†• ȏʹͺȐǡ ƒ† ‘šƒǦ †‡ƒœƒˆŽƒ˜‹‡• ȏʹͻȐǤ  ƒ††‹–‹‘ –‘ –Š‡•‡ ‹†• ‘ˆ ƒ’’Ž‹…ƒ–‹‘ǡ •‘‡‘ˆ–Š‡•‡†‡”‹˜ƒ–‹˜‡•Šƒ˜‡„‡‡‹˜‡•–‹‰ƒ–‡†ƒ•‘ǦŽ‹‡ƒ” ‘’–‹…ƒŽƒ–‡”‹ƒŽ•ȏ͵ͲȐƒ††›‡•ȏ͵ͳȐǤ Š‡•›–Š‡•‹•‘ˆƒ”›Ž‹†‡‡„ƒ”„‹–—”‹…ƒ…‹†•Šƒ•„‡‡…ƒ””‹‡† ‘—– „› …‘†‡•ƒ–‹‘ ‘ˆ ƒ”‘ƒ–‹… ƒŽ†‡Š›†‡• ™‹–Š „ƒ”„‹–—”‹… ƒ…‹†Ǥƒ”‹‘—•”‡ƒ‰‡–•Ȁ‡–Š‘†•Šƒ˜‡„‡‡”‡’‘”–‡†‹–Š‡Ž‹–Ǧ ‡”ƒ–—”‡ǡ ‡Ǥ‰Ǥǡ „ƒ•‹… ƒŽ—‹ƒ ȏ͵ʹȐǡ ‹ˆ”ƒ”‡† ȋ Ȍ ‹””ƒ†‹ƒ–‹‘ ȏ͵͵Ȑǡ ‹…”‘™ƒ˜‡ ‹””ƒ†‹ƒ–‹‘ ȏ͵ͶȐǡ  ʹ͵  ȏ͵ͷȐǡ ‹ ƒ‘’ƒ”–‹…Ž‡• ȏ͵͸Ȑǡ Ǧ’”‘Ž‹‡ȏ͵͹Ȑǡ‹Ž͵ȏ͵ͺȐǡ‡ͳ‰x”ͳǦxʹȏ͵ͻȐǡ‹‘‹…Ž‹“—‹†• ȏͶͲȐǡ ‹ʹȉͳʹ͵ȉʹͶ ʹ ȏͶͳȐǡ ƒ† –”‹‡–Š›Ž„‡œ›Ž ƒ‘‹— …ŠŽ‘”‹†‡ȋȌȏͶʹȐǤ ‘™‡˜‡”ǡ‘•–‘ˆ–Š‡’”‘–‘…‘Ž•Ȁ”‡ƒ‰‡–• •—ˆˆ‡”ˆ”‘•Š‘”–…‘‹‰••—…Šƒ•Ž‡‰–Š›”‡ƒ…–‹‘–‹‡ǡ‡š’‡Ǧ •‹˜‡Ȁ–‘š‹…Ȁ—ƒ˜ƒ‹Žƒ„Ž‡ ”‡ƒ‰‡–•ǡ Š‹‰ŠǦ–‡’‡”ƒ–—”‡ …‘†‹–‹‘•ǡ Šƒœƒ”†‘—• •‘Ž˜‡–•ǡ ˆ‘”ƒ–‹‘ ‘ˆ —†‡•‹”ƒ„Ž‡ ’”‘†—…–•ǡ Ž‘™ ›‹‡Ž†•ǡ ‘Ǧ”‡…›…Žƒ„‹Ž‹–›ǡ ƒ† †‹ˆˆ‹…—Ž– …ƒ–ƒŽ›•– •‡’ƒ”ƒ–‹‘Ǥ ‘ ‘˜‡”…‘‡–Š‡•‡†”ƒ™„ƒ…•ǡƒ†‹…‘–‹—ƒ–‹‘‘ˆ‘—”’”‡˜‹‘—• ™‘” ‘ ‰”‡‡ …ƒ–ƒŽ›•‹• ȏͶ͵Ȑ ƒ† ƒ‘ƒ–‡”‹ƒŽ• ȏͶͶǡͶͷȐǡ ™‡ —•‡†…‘„ƒŽ–ˆ‡””‹–‡ƒ•ƒŠ‡–‡”‘‰‡‡‘—•…ƒ–ƒŽ›–‹…•›•–‡Ǥ   –Š‹• ’ƒ’‡”ǡ ™‡ Š‹‰ŠŽ‹‰Š– ‘—” ™‘” ‘ –Š‡ •›–Š‡•‹• ‘ˆ ƒ‰‡–‹…ƒŽŽ› ”‡…‘˜‡”ƒ„Ž‡ •—’‡”’ƒ”ƒƒ‰‡–‹… …‘„ƒŽ– ˆ‡””‹–‡ ƒ‰‡–‹…ƒ‘’ƒ”–‹…Ž‡•‘ˆŠ‹‰Š•—”ˆƒ…‡ƒ”‡ƒƒ•ƒ…ƒ–ƒŽ›•–ǡƒ†ƒ •‹’Ž‡ǡ ‡ˆˆ‹…‹‡–ǡ ‰”‡‡ ’”‘–‘…‘Ž ˆ‘” –Š‡ •›–Š‡•‹• ‘ˆ ƒ”›Ž‹†‡‡ „ƒ”„‹–—”‹…ƒ…‹††‡”‹˜ƒ–‹˜‡•Ǥ 2.  Experimental  2.1.  Preparationofcobaltferritenanoparticles Š‡…‘„ƒŽ–ˆ‡””‹–‡ƒ‘’ƒ”–‹…Ž‡•™‡”‡•›–Š‡•‹œ‡†—•‹‰–Š‡ …Š‡‹…ƒŽ …‘’”‡…‹’‹–ƒ–‹‘–‡…Š‹“—‡ȏͶ͸Ȑǡ™‹–Š ‹‘”‘†‹ˆ‹…ƒǦ –‹‘•ǤŠ‡ ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡• ™‡”‡ ’”‡’ƒ”‡† „›…‘’”‡…‹’‹Ǧ –ƒ–‹‘‘ˆ ‡Ž͵ƒ†‘Žʹȉ͸ ʹ‹ƒ„ƒ•‹…•‘Ž—–‹‘—†‡”—Ž–”ƒǦ •‘‹…ƒ–‹‘Ǥ ‡Ž͵ȋͻǤ͵‘ŽȌƒ†‘Žʹȉ͸ ʹȋͶǤʹ‘ŽȌ™‡”‡ •‡’ƒ”ƒ–‡Ž›†‹••‘Ž˜‡†‹†‡‹‘‹œ‡†™ƒ–‡”ȋͷͲŽȌƒ†’Žƒ…‡†‹ ƒ—Ž–”ƒ•‘‹…ƒ–‘”Ǥƒ“—‡‘—••‘Ž—–‹‘‘ˆ ȋ͵‘ŽȀǡʹͷŽȌ ™ƒ•ƒ††‡†—†‡”—Ž–”ƒ•‘‹…ƒ–‹‘ƒ†–Š‡‹š–—”‡™ƒ••‘‹…ƒ–Ǧ ‡† ˆ‘” ͵Ͳ ‹Ǥ  „Žƒ… †‹•’‡”•‹‘ ™ƒ• ˆ‘”‡† †—”‹‰ •‘‹Ǧ …ƒ–‹‘ǡ ƒ† –Š‡ „Žƒ… ’”‡…‹’‹–ƒ–‡ ™ƒ• •‡’ƒ”ƒ–‡† ‘—– —•‹‰ ƒ ‡š–‡”ƒŽ ƒ‰‡–ǡ ™ƒ•Š‡† ™‹–Š Žƒ”‰‡ ƒ‘—–• ‘ˆ ‹ŽŽ‹’‘”‡ ™ƒǦ –‡”ǡƒ†–Š‡™ƒ•Š‡†™‹–Š‡–Šƒ‘ŽǤŠ‡’”‘†—…–™ƒ•–Š‡†”‹‡† ‹ƒ‘˜‡ƒ–ͳͲͲιˆ‘”ͳŠƒ†•–‘”‡†ˆ‘”ˆ—”–Š‡”—•‡Ǥ 2.2.  Characterizationofcobaltferritenanoparticles Š‡…”›•–ƒŽ•–”—…–—”‡‘ˆ–Š‡…‘„ƒŽ–ˆ‡””‹–‡ƒ‘’ƒ”–‹…Ž‡•™ƒ•

†‡–‡”‹‡† „› Ǧ”ƒ› †‹ˆˆ”ƒ…–‹‘ ȋȌ —•‹‰ ƒ ƒŽ›–‹…ƒŽ ȋȌǦ”ƒ›†‹ˆˆ”ƒ…–‘‡–‡”™‹–Š—K”ƒ†‹ƒ–‹‘ȋ  α ͲǤͳͷͶ Ȍǡ ‹ –Š‡ ʹ  ”ƒ‰‡ ʹͲιȂͺͲιǤ ‘—”‹‡” –”ƒ•ˆ‘”  ȋ Ǧ Ȍ •’‡…–”‘•…‘’› ™ƒ• …ƒ””‹‡† ‘—– ‹ –Š‡ ”ƒ‰‡ ͶͲͲȂͶͲͲͲ …Ϋͳ™‹–Šƒ‡”‹Ž‡”’‡…–”—Ǧ  ǡ—•‹‰”’‡ŽŽ‡–•Ǥ Š‡ ˆ‘”ƒ–‹‘ ‘ˆ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ™ƒ• …‘ˆ‹”‡† „› •…ƒ‹‰ ‡Ž‡…–”‘ ‹…”‘•…‘’›Ȁ‡‡”‰›Ǧ†‹•’‡”•‹˜‡ Ǧ”ƒ› •’‡…Ǧ –”‘•…‘’› ȋǦȌ ƒƒŽ›•‹•ǡ ™Š‹…Š ™ƒ• …ƒ””‹‡† ‘—– —•‹‰ ƒ

 Ǧ͸͸ͳͲǤŠ‡‘ ‡ʹͶ‘”’Š‘Ž‘‰›™ƒ••–—†‹‡†—•‹‰ –”ƒ•‹••‹‘ ‡Ž‡…–”‘ ‹…”‘•…‘’› ȋȌǤ Š‡ •ƒ’Ž‡ ™ƒ• ’”‡’ƒ”‡† „› ‡–Šƒ‘Ž †‹•’‡”•‹‘ ‘ˆ ƒ‘’ƒ”–‹…Ž‡•ǡ ™Š‹…Š ™‡”‡ †‡’‘•‹–‡†‘ƒ…ƒ”„‘Ǧ…‘ƒ–‡†—‰”‹†ǡƒ†ƒˆ–‡”†”›‹‰ǡƒƒŽ›•‹• ™ƒ•’‡”ˆ‘”‡†—•‹‰ƒ ‹–ƒ…Š‹͹ͷͲͲ‹•–”—‡–ǤŠ‡ƒ‰‡–Ǧ ‹…’”‘’‡”–‹‡•™‡”‡‡ƒ•—”‡†—•‹‰ƒ˜‹„”ƒ–‹‰•ƒ’Ž‡ƒ‰‡Ǧ –‘‡–‡”ȋǡ”‹…‡–‘’’Ž‹‡†‡•‡ƒ”…Š‘†‡ŽͳͷͷȌƒ–”‘‘ –‡’‡”ƒ–—”‡ ™‹–Šƒƒš‹— ƒ‰‡–‹… ˆ‹‡Ž† ”ƒ‰‡‘ˆ Ϊͳ  –‘ ΫͳǤ Š‡”‘‰”ƒ˜‹‡–”‹… ƒƒŽ›•‹• ȋ Ȍǡ †‹ˆˆ‡”‡–‹ƒŽ –Š‡”ƒŽ ƒƒŽ›•‹•ȋȌǡƒ††‹ˆˆ‡”‡–‹ƒŽ–Š‡”ƒŽ‰”ƒ˜‹‡–”›ȋ Ȍ™‡”‡ ’‡”ˆ‘”‡†‘–Š‡…ƒ–ƒŽ›•–—•‹‰ƒ͸ͲͲͲ Ȁ͸͵ͲͲ ‹•–”—‡– ‹ –Š‡ –‡’‡”ƒ–—”‡ ”ƒ‰‡ ͷͲΫ͹ͲͲ ι ƒ– ƒ Š‡ƒ–‹‰ ”ƒ–‡‘ˆͳͲιȀ‹‹ƒ–ƒ—†‡”ƒƒ‹”ƒ–‘•’Š‡”‡ǤŠ‡•’‡Ǧ …‹ˆ‹… •—”ˆƒ…‡ ƒ”‡ƒ ‘ˆ –Š‡ …ƒ–ƒŽ›•– ™ƒ• †‡–‡”‹‡† —•‹‰ ƒ —ƒ–ƒ…Š”‘‡ ǦͶͲͲͲ‡ ‹•–”—‡– ƒ– Ž‹“—‹†Ǧ‹–”‘‰‡ –‡’‡”ƒ–—”‡™‹–Š˜ƒ…——†‡‰ƒ••‹‰ƒ–ͳͳͲιˆ‘”͵ŠǤŠ‡•’‡Ǧ …‹ˆ‹…•—”ˆƒ…‡ƒ”‡ƒ™ƒ•‘„–ƒ‹‡†—•‹‰–Š‡‡“—ƒ–‹‘Ǥ 2.3.  Synthesisofarylidenebarbituricacidderivatives ŽŽ”‡ƒ…–‹‘•™‡”‡…ƒ””‹‡†‘—–—•‹‰”‡ƒ‰‡–Ǧ‰”ƒ†‡•‘Ž˜‡–• ƒ†–Š‡”‡ƒ‰‡–•™‡”‡’—”…Šƒ•‡†ˆ”‘ƒŽ‘…ƒŽ•—’’Ž‹‡”Ǥ  ͵ ‹ŽŽ‹’‘”‡ ƒ’’ƒ”ƒ–—• ™ƒ• —•‡† –‘ ’”‘˜‹†‡ †‡‹‘‹œ‡† ™ƒ–‡”Ǥ Ž–”ƒ•‘‹…ƒ–‹‘ ™ƒ• …ƒ””‹‡† ‘—– —•‹‰ ƒ ‘„ƒ Š‡‹‡ ͵ǤͷͳͲͲ ͳ—Ž–”ƒ•‘‹…ƒ–‘”Ǥ ƒ”„‹–—”‹… ƒ…‹† ȋͷ ‘ŽȌ ™ƒ• †‹••‘Ž˜‡† ‹ ƒ ™ƒ–‡”Ǧ‡–Šƒ‘Ž ‹š–—”‡ ȋͳǣͳǡ ͷ ŽȌǡ ˆ‘ŽŽ‘™‡† „› ƒ††‹–‹‘ ‘ˆ ƒ ƒ”‘ƒ–‹… ƒŽ†‡Ǧ Š›†‡ȋͷ‘ŽȌǤŠ‡‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡…ƒ–ƒŽ›•–ȋͷ‘ŽΨ‘” ͲǤͲͳͳ͹ ‰Ȍ ™ƒ• ƒ††‡† –‘ –Š‡ ”‡ƒ…–‹‘ ‹š–—”‡ ƒ† –Š‡ ‹š–—”‡ ™ƒ••–‹””‡†—–‹Ž…‘’Ž‡–‹‘‘ˆ–Š‡”‡ƒ…–‹‘Ǥˆ–‡”–Š‡”‡ƒ…–‹‘ ™ƒ• …‘’Ž‡–‡ǡ –Š‡ …ƒ–ƒŽ›•– ™ƒ• •‡’ƒ”ƒ–‡† —•‹‰ ƒ ƒ‰‡–‹… •‡’ƒ”ƒ–‘”ǡ™ƒ•Š‡†™‹–Š‡–Šƒ‘Žǡƒ†–Š‡†”‹‡†ƒ–͹Ͳιˆ‘”ͳŠǤ Š‡•‘Ž‹†…”—†‡’”‘†—…–™ƒ•™ƒ•Š‡†™‹–Š™ƒ–‡”ƒ††”‹‡†ǤŠ‡ ’”‘†—…–™ƒ•ˆ—”–Š‡”’—”‹ˆ‹‡†„›”‡…”›•–ƒŽŽ‹œƒ–‹‘ˆ”‘‡–Šƒ‘ŽǤ Š‡ •›–Š‡•‹œ‡† ƒ”›Ž‹†‡‡ „ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡• ™‡”‡ …Šƒ”ƒ…–‡”‹œ‡† —•‹‰ Ǧ  ƒ† ͳ  —…Ž‡ƒ” ƒ‰‡–‹… ”‡•‘ƒ…‡ ȋȌ •’‡…–”‘•…‘’‹‡•Ǥ ‡Ž–‹‰ ’‘‹–• ™‡”‡ ”‡…‘”†‡† —•‹‰ ƒ

ƒŽŽ‡ƒ’ ‹•–”—‡– ƒ† ƒ”‡ —…‘””‡…–‡†Ǥ ͳ Ǧ ȋͶͲͲ  œȌ•’‡…–”ƒ™‡”‡‘„–ƒ‹‡†™‹–Šƒ”—…‡”†˜ƒ…‡ͶͲͲ•’‡…Ǧ –”‘‡–‡” ȋŽ͵Ȍ —•‹‰ –‡–”ƒ‡–Š›Ž•‹Žƒ‡ ƒ• –Š‡ ‹–‡”ƒŽ •–ƒ†ƒ”†ǤŠ‡‡–”›—„‡”•”‡ˆ‡”–‘ƒ„Ž‡ʹǤ 3aǤ Ǥ’Ǥ ʹ͸ʹȂʹ͸Ͷ ιǤ Ǧ  ȋ”ǡ …ΫͳȌǣ ͵ʹͳͲǡ ͵Ͳͷͻǡ ͳ͹ͷͲǡ ͳ͸͹ͲǤͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͹ǤͶʹȂͺǤͳͳȋǡͷ ȌǡͺǤ͵͹ȋ•ǡ ͳ ȌǡͳͳǤʹͺȋ•ǡͳ ǡ ȌǡͳͳǤͶʹȋ•ǡͳ ǡ ȌǤͳ͵Ǧǣͳ͸͵Ǥͻǡͳ͸ʹǤʹ, ͳͷͷǤ͹ǡͳͷͳǡͳ͵͵Ǥͻǡͳ͵͵Ǥͷǡͳ͵ʹǤͻǡͳʹͻǡͳͳͻǤ m/zǣʹͳ͸Ǥ 3bǤǤ’Ǥʹͻ͸ȂʹͻͺιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͹Ǥ͵Ͳȋ†ǡ ͳ Ȍǡ͹Ǥʹ͸ȋ†ǡͳ Ȍǡ͹ǤͳͶȂ͹ǤʹͲȋ–ǡʹ ȌǡͺǤʹ͹ȋ•ǡͳ ȌǡͳͳǤʹͶȋ•ǡͳ ǡ  ȌǡͳͳǤͶͲȋ•ǡͳ ǡ ȌǤ m/zǣʹͷͲǤ 

JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704

3cǤǤ’ǤʹͷʹȂʹͷͶιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͹ǤͷͲȋ†ǡ ʹ ȌǡͺǤͲͳȋ†ǡʹ ȌǡͺǤʹͲȋ•ǡͳ ȌǡͳͳǤʹͲȋ•ǡͳ ǡ ȌǡͳͳǤ͵ͻȋ•ǡͳ ǡ  ȌǤ m/zǣʹͷͲǤ 3dǤǤ’Ǥʹͻ͹ȂʹͻͻιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͵Ǥͺͷȋ•ǡ ͵ Ȍǡ͹Ǥͳͺȋ†ǡʹ ȌǡͺǤͶͲȋ†ǡʹ ȌǡͺǤʹͲȋ•ǡͳ ȌǡͳͳǤͲ͹ȋ•ǡͳ ǡ Ȍǡ ͳͳǤͳͻȋ•ǡͳ ǡ ȌǤ m/zǣʹͶ͸Ǥ 3eǤǤ’Ǥε͵ʹͲιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͸ǤͺͷȂ͸Ǥͺ͹ ȋ†ǡʹ ȌǡͺǤʹͶȋ•ǡͳ ȌǡͺǤ͵ͳȂͺǤ͵͵ȋ†ǡʹ ȌǡͳͲǤ͸͸ȋ•ǡͳ ǡ ȌͳͳǤͳʹ ȋ•ǡͳ ǡ ȌǡͳͳǤʹͶȋ•ǡͳ ǡ ȌǤ m/zǣʹ͵ʹǤ 3fǤǤ’Ǥʹ͹͸ιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͵ǤͳͲȋ•ǡ͸ Ȍǡ ͸Ǥ͹ͻȋ†ǡʹ ȌǡͺǤͳʹȋ•ǡͳ ȌǡͺǤͶͲȋ†ǡʹ ȌǡͳͲǤ͹ȋ•ǡͳ ǡ ȌǡͳͳǤͲͷȋ•ǡ ͳ ǡ ȌǤ m/zǣʹͷͻǤ  3gǤ Ǥ’Ǥ ʹ͸͸Ȃʹ͸ͺ ιǤ ͳ Ǧ ȋͶͲͲ œ Ǧd͸ǡ Ȍǣ ͸ǤͷʹȂ͸Ǥͺʹȋǡʹ Ȍǡ͹ǤͺʹȂ͹ǤͳͲȋǡͷ ȌǡͺǤʹͲȋ†ǡͳ ȌǡͳͳǤʹͻȋ•ǡͳ ǡ  ȌǡͳͳǤͶ͹ȋ•ǡͳ ǡ ȌǤ m/zǣʹͶʹǤ 3hǤǤ’Ǥ͵ͲͲȂ͵ͲʹιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͸Ǥ͹ͷȋ†ǡ ͳ ȌǡͺǤͲͳȋ•ǡͳ ȌǡͺǤͳͳȋ•ǡͳ ȌǡͺǤͷʹȋ†ǡͳ ȌǡͳͳǤʹ͵ȋ•ǡͳ ǡ Ȍǡ ͳͳǤ͵ͳȋ•ǡͳ ǡ ȌǤ m/zǣʹͲ͸Ǥ 3iǤǤ’ǤʹͻͲȂʹͻʹιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣʹǤͷͲȋ†ǡ ͵ Ȍǡ͸ǤͶ͸ȋ†ǡͳ ȌǡͺǤͲͶȋ•ǡͳ ȌǡͺǤͷͳȋ†ǡͳ ȌǡͳͳǤͳʹȋ•ǡͳ ǡ Ȍǡ ͳͳǤʹͲȋ•ǡͳ ǡ ȌǤ m/zǣʹʹͳǤ 3jǤǤ’Ǥʹ͵ͺȂʹͶͳιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͹ǤͳͲȋ–ǡ ʹ ȌǡͺǤ͵Ͳȋ•ǡͳ ȌǡͺǤͷͲȋ††ǡͳ ȌǡͺǤͳͳȋ•ǡͳ ȌǡͳͳǤ͵ʹȋ•ǡͳ ǡ Ȍǡ ͳͳǤͶͶȋ•ǡͳ ǡ ȌǤ m/zǣʹ͸ͳǤ 3kǤǤ’Ǥε͵ͲͲιǤͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͵Ǥ͹͸ȋ•ǡ͵ Ȍǡ ͵Ǥͺͷȋ•ǡ͵ Ȍǡ͹Ǥ͵ȋ†ǡͳ Ȍǡ͹Ǥͺ͸ȋ††ǡͳ ȌǡͺǤʹͲȋ•ǡͳ ȌǡͺǤ͵ͷȋ†ǡͳ Ȍǡ ͳͳǤͲʹȋ•ǡͳ ǡ ȌǡͳͳǤͲͶȋ•ǡͳ ǡ ȌǤ m/zǣʹ͹͸Ǥ 3lǤǤ’Ǥͳ͸ʹȂͳ͸ͶιǤ ͳ ǦȋͶͲͲ œǦd͸ǡȌǣ͸Ǥ͸͹ȋ•ǡ ͳ ȌǡʹǤͲͷȋ•ǡ͵ Ȍǡ͹ǤͻʹȂ͹ǤͲͶȋǡͷ ȌǡͺǤͲͻȋ•ǡͳ ȌǡͳͳǤʹ͹ȋ•ǡͳ ǡ  ȌǡͳͳǤͶͶȋ•ǡͳ ǡ ȌǤ m/zǣʹͷ͸Ǥ 3mǤǤ’Ǥε͵ʹͲιǤ m/zǣʹͷͷǤ 3nǤǤ’Ǥ͵ͳͷȂ͵ͳͺιǤ ͳ ǦȋͶͲͲ œǦ†͸ǡȌǣ͵ǤͺͶȋ•ǡ ͸ Ȍǡ͹Ǥͻȋ•ǡͳ ȌǡͺǤͲͶȋ•ǡͳ ȌǡͺǤͷʹȋ•ǡͳ ȌǡͻǤ͹ȋ•ǡͳ ȌǡͳͳǤͲͺȋ•ǡ ͳ ǡ ȌǡͳͳǤʹͳȋ•ǡͳ ǡ ȌǤ m/zǣ͵͸͸Ǥ 3.  Resultsanddiscussion 3.1.  CharacterizationresultsofCoFe2O4nanoparticles Š‡ Ǧ  •’‡…–”ƒ ‘ˆ ‘ ‡ʹͶ •Š‘™‡† ’‡ƒ• ƒ– ͷͺ͸Ǥʹͷǡ ͳͲͷͶǤ͵Ͳǡͳ͵͵ͻǤ͹ͲǡͳͶͺͺǤ͵ͷǡͳ͸ʹ͸ǤͲ͹ǡƒ†͵͵͹ͲǤͻ͵…Ϋͳȋ ‹‰ǤͳȌǤ Š‡ ’‡ƒ ‘„•‡”˜‡† ƒ– ͷͺ͸Ǥʹͷ …Ϋͳ …‘””‡•’‘†• –‘ –Š‡ Ȃ –‡–”ƒŠ‡†”ƒŽ•‹–‡‘ˆ–Š‡•’‹‡Ž•–”—…–—”‡ǡƒ†–Š‹•’‡ƒ•Š‘™•–Š‡

1000

(511) (440) (400)

(200)

600 400 200 20

30

40

50

60

70

80

2T/( o ) Fig.2.’ƒ––‡”‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

„ƒ•‹…ƒ–—”‡‘ˆ–Š‡ƒ‘’ƒ”–‹…Ž‡•‘„–ƒ‹‡†ȏͶ͹ȐǤ Š‡  ’ƒ––‡” ‘ˆ –Š‡ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ‹• •Š‘™ ‹ ‹‰ǤʹǤŽŽ–Š‡†‹ˆˆ”ƒ…–‹‘’‡ƒ•ƒ†”‡Žƒ–‹˜‡‹–‡•‹–›ƒ–…Š–Š‡

 ȋ –‡”ƒ–‹‘ƒŽ ‡–‡” ˆ‘” ‹ˆˆ”ƒ…–‹‘ ƒ–ƒȌ   …ƒ”†• ͵Ǧͺ͸Ͷ ƒ† ʹʹǦͳͲͺ͸ ˜‡”› ™‡ŽŽ ȏͶͺǡͶͻȐǤ Š‹• ”‡˜‡ƒŽ‡† –Šƒ– –Š‡ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• Šƒ˜‡ …—„‹… •–”—…–—”‡Ǥ Š‡ ’‡ƒ „”‘ƒ†Ǧ ‡‹‰ ‹†‹…ƒ–‡• –Š‡ ƒ‘…”›•–ƒŽŽ‹‡ ƒ–—”‡ ‘ˆ –Š‡ •ƒ’Ž‡Ǥ Š‡ ƒ‘’ƒ”–‹…Ž‡…”›•–ƒŽŽ‹–‡•‹œ‡™ƒ•ƒŽ•‘†‡–‡”‹‡†ˆ”‘–Š‡ ’ƒ––‡”—•‹‰–Š‡‡„›‡Ǧ…Š‡””‡”ˆ‘”—ŽƒȏͷͲȐƒ†™ƒ•ˆ‘—† –‘ „‡ ʹǤͺ͹ ǡ ™Š‹…Š ‹• …‘•‹•–‡– ™‹–Š –Š‡ ’ƒ”–‹…Ž‡ •‹œ‡ ‘„Ǧ –ƒ‹‡†ˆ”‘ƒƒŽ›•‹•Ǥ  Š‡•–”—…–—”ƒŽ…‘’‘•‹–‹‘™ƒ•‡šƒ‹‡†„›ǡƒ••Š‘™ ‹ ‹‰Ǥ͵ǤŠ‡ƒƒŽ›•‹••Š‘™‡†–Š‡‡Ž‡‡–ƒŽ†‹•–”‹„—–‹‘‘ˆ ‘ ‡ʹͶƒ†–Š‡’”‡•‡…‡‘ˆ‘ƒ† ‡ǤŠ‡•—”ˆƒ…‡‘”’Š‘Ž‘Ǧ ‰› ™ƒ• †‡–‡”‹‡† —•‹‰  ƒƒŽ›•‹•ǡ ƒ† –Š‡ ƒƒŽ›•‹• •Š‘™‡† –Šƒ– –Š‡ ƒ‘’ƒ”–‹…Ž‡• Šƒ† ”‘—‰Š ”‘…› •—”ˆƒ…‡•ǡ ƒ• •Š‘™‹ ‹‰ǤͶǤ ™ƒ• ƒŽ•‘—•‡†–‘†‡–‡”‹‡–Š‡ •‹œ‡ƒ† •Šƒ’‡‘ˆ–Š‡ ƒ‘’ƒ”–‹…Ž‡•ǡ ƒ† –Š‡  ‹ƒ‰‡• ƒ”‡ •Š‘™ ‹ ‹‰Ǥ ͷǤ Š‡ ƒ˜‡”ƒ‰‡ƒ‘’ƒ”–‹…Ž‡•‹œ‡™ƒ•ˆ‘—†–‘„‡‹–Š‡”ƒ‰‡ʹȂͺǡ ™Š‹…Š‹•‹ƒ‰”‡‡‡–™‹–Š–Š‡ƒ˜‡”ƒ‰‡•‹œ‡‘„–ƒ‹‡†ˆ”‘–Š‡  ’ƒ––‡”Ǥ Š‡  ‹ƒ‰‡• •Š‘™‡† –Šƒ– –Š‡ ƒ‘’ƒ”–‹…Ž‡• ™‡”‡•’Š‡”‹…ƒŽǤ ‹‡Ž†Ǧ†‡’‡†‡– ƒ‰‡–‹… ‡ƒ•—”‡‡–• ™‡”‡ ’‡”ˆ‘”‡† ‘ –Š‡ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ƒ– ”‘‘ –‡’‡”ƒ–—”‡ǡ —•‹‰ ƒ

Co Fe O

70

Intensity

65 T (%)



(311)

800 Counts



60 55

Fe Co Fe

50 45

Co

4000 3600 3200 2800 2400 2000 1600 1200 800 400 Wavenumber (cm1) Fig.1. Ǧ •’‡…–”—‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

2

4

6 8 Energy (keV)

10

Fig.3.ƒƒŽ›•‹•‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

12



JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704

(a)

2.0 Ms = 1.77 emu/g Mr = 0.259 emu/g Hc = 527 Oe

Magnetisation (emu/g)

1.5 1.0 0.5 0.0 -0.5 -1.0 -1.5 -2.0 -10000

(b)

-5000

0 5000 Magnetic field (Oe)

10000

Fig.6. ‹‡Ž†Ǧ†‡’‡†‡–ƒ‰‡–‹œƒ–‹‘‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

 Fig.4.‹ƒ‰‡•‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

ǡ ‹ –Š‡ ”ƒ‰‡ ˆ”‘ Ϊͳ  –‘ Ϋͳ ǡ ƒ• •Š‘™ ‹ ‹‰Ǥ ͸Ǥ Š‡ •ƒ–—”ƒ–‹‘ƒ‰‡–‹œƒ–‹‘ȋM•Ȍǡ ”‡ƒ‡…‡ ȋM”Ȍǡƒ† …‘‡”…‹˜‹–› ȋH…Ȍ˜ƒŽ—‡•™‡”‡‘„–ƒ‹‡†ˆ”‘–Š‡Š›•–‡”‡•‹•Ž‘‘’ǤŠ‡M•™ƒ• ͳǤ͹͹‡—Ȁ‰ǡ…‘’ƒ”‡†™‹–Š–Š‡…‘””‡•’‘†‹‰„—Ž˜ƒŽ—‡‘ˆͺ͵ ‡—Ȁ‰ ȏͷͳȐǤ Š‡ H… ™ƒ• ͷʹ͹ ‡Ǣ M” ™ƒ• ˆ‘—† –‘ „‡ ͲǤʹͷͻ ‡—Ȁ‰ ƒ† –Š‡ •“—ƒ”‡‡•• ”ƒ–‹‘ ȋM”ȀM•Ȍ ™ƒ• ͲǤͳͶ͸Ǥ Š‡ †‡Ǧ …”‡ƒ•‡‹M•…‘’ƒ”‡†™‹–Š–Šƒ–‘ˆ–Š‡„—Žƒ–‡”‹ƒŽ‹•’”‹ƒ”Ǧ ‹Ž›…ƒ—•‡†„›–Š‡‡ˆˆ‡…–‘ˆ–Š‡•ƒŽŽ’ƒ”–‹…Ž‡•—”ˆƒ…‡ƒ”‡ƒǡ™Š‹…Š

(a)

„‡…‘‡• ’”‘‹‡– ƒ• –Š‡ ’ƒ”–‹…Ž‡ •‹œ‡ †‡…”‡ƒ•‡• ȏͷʹȐǤ Š‡ …—”˜‡•Š‘™•ƒŽ‘•–‘Š›•–‡”‡•‹•ƒ†‹•”‡˜‡”•‹„Ž‡ǤŠ‡•‹œ‡‘ˆ –Š‡ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ‹• „‡Ž‘™ –Š‡ •—’‡”’ƒ”ƒƒ‰‡–‹… …”‹–‹…ƒŽ •‹œ‡ǡ ƒ• …‘ϐ‹”‡† „›  ȋʹΫͺ ȌǤ Š‡ •›–Š‡•‹œ‡† ƒ‘’ƒ”–‹…Ž‡• –Š‡”‡ˆ‘”‡ •Š‘™ •—’‡”’ƒ”ƒƒ‰‡–‹… …Šƒ”ƒ…–‡”‹•Ǧ –‹…•Ǥ Š‡ •—”ˆƒ…‡ ƒ”‡ƒ ‹• ƒ ‹’‘”–ƒ– ’ƒ”ƒ‡–‡” ˆ‘” …ƒ–ƒŽ›•‹•Ǥ Š‡•—”ˆƒ…‡ƒ”‡ƒ‘ˆ–Š‡‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•™ƒ•†‡–‡”‹‡† —•‹‰–Š‡‡“—ƒ–‹‘ȏͷ͵Ȑǡƒ†™ƒ•ˆ‘—†–‘„‡ͳͶͲǤͻʹȀ‰ǡ …ƒŽ…—Žƒ–‡†ˆ”‘–Š‡’Ž‘–‹ ‹‰Ǥ͹Ǣ–Š‹•‹•—…ŠŠ‹‰Š‡”–Šƒ –Š‡•—”ˆƒ…‡ƒ”‡ƒ‘ˆ„—Ž…‘„ƒŽ–ˆ‡””‹–‡ȏͷͶȂͷ͸ȐǤŠ‡Š‹‰Š‡”•—”Ǧ ˆƒ…‡ƒ”‡ƒ‹•ƒƒ†˜ƒ–ƒ‰‡‹‹’”‘˜‹‰…ƒ–ƒŽ›–‹…’‡”ˆ‘”ƒ…‡Ǥ ‹ƒŽŽ›ǡ –Š‡ •–ƒ„‹Ž‹–› ‘ˆ –Š‡ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ™ƒ• †‡Ǧ –‡”‹‡†—•‹‰  Ǣ–Š‡ ”‡•—Ž–• ƒ”‡ •Š‘™‹ ‹‰ǤͺǤŠ‡  ’ƒ––‡”•Š‘™•–Šƒ–ƒ‹‹–‹ƒŽƒ••Ž‘••‘……—””‡†—’–‘ͳͷͲ郕 ƒ”‡•—Ž–‘ˆ‡˜ƒ’‘”ƒ–‹‘‘ˆƒ†•‘”„‡†™ƒ–‡”ƒ†–Š‡’”‡•‡…‡‘ˆ ˜‘Žƒ–‹Ž‡…‘’‘‡–•ǤŠ‡ˆ—”–Š‡”ƒ••Ž‘••‘„•‡”˜‡†„‡–™‡‡ ͳͷͲ郐†͵͸Ͳ鏃›„‡…ƒ—•‡†„›Ž‘••‘ˆ•–”—…–—”ƒŽ™ƒ–‡”‘” Š›†”‘š›Ž ‰”‘—’• ‘ –Š‡ •ƒ’Ž‡ •—”ˆƒ…‡Ǥ Š‡ ˆ‹ƒŽ †‡…‘’‘•‹Ǧ –‹‘ –‡’‡”ƒ–—”‡ ™ƒ• ƒ– ƒ”‘—† ͵͸ͳ ιǢ ‘ ˆ—”–Š‡” ƒ•• Ž‘•• ™ƒ•†‡–‡…–‡†—’–‘͹ͲͲιǡ™Š‹…Š•Š‘™‡†–Š‡–Š‡”ƒŽ•–ƒ„‹Ž‹–› ‘ˆ–Š‡…ƒ–ƒŽ›•–Ǥ™‘’‡ƒ•ǡ‘‡‡†‘–Š‡”‹…ƒ†–Š‡‘–Š‡”‡š‘Ǧ –Š‡”‹…ǡ™‡”‡‘„•‡”˜‡†‹–Š‡…‘””‡•’‘†‹‰’ƒ––‡”ǤŠ‡ ”ƒ–‡ ‘ˆ †‡…‘’‘•‹–‹‘ ’‡” ‹—–‡ ƒ– –Š‡ …‘””‡•’‘†‹‰   –‡’‡”ƒ–—”‡ ™ƒ• ƒŽ•‘ †‡–‡”‹‡†ǡ ƒ† –Š‹• •Š‘™‡† –Šƒ– ƒ– ͵ͷʹǤ͵ι–Š‡”ƒ–‡‘ˆ†‡…‘’‘•‹–‹‘™ƒ•‘Ž›ͳ͹ͻρ‰Ȁ‹ǡ™Š‹…Š ˆ—”–Š‡”•—’’‘”–•–Š‡–Š‡”ƒŽ•–ƒ„‹Ž‹–›‘ˆ–Š‡…ƒ–ƒŽ›•–Ǥ 8

100 nm 1/[W((p0/p)1)]

7

(b)

6

Slope = 24.44 Intercept = 0.273 C constant = 90.464 Correlation coefficient, r = 0.999975 Surface area = 140.9 m2/g

5 4 3 2 1

20 nm

0.05 

Fig.5.‹ƒ‰‡•‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

0.10

0.15

0.20

0.25

p/p0 Fig.7.’Ž‘–‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

0.30



JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704

10

20

Table1 ’–‹‹œƒ–‹‘‘ˆ”‡ƒ…–‹‘…‘†‹–‹‘•—•‹‰‘ ‡ʹͶƒ‘…ƒ–ƒŽ›•–Ǥ

100 8

O

10

O

95

NH

NH O

0

90

TGA DTA

-10

80

-20

75

352.3 oC 179.2 Pg/min

2 -30

70 DTG

0

65 0

100

200

300

400

500

600

Temperature (oC) Fig.8. ȀȀ ƒƒŽ›•‹•‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•Ǥ

3.2.  CatalyticapplicationofCoFe2O4nanoparticlesinsynthesis ofarylidenebarbituricacidderivatives ‘‹˜‡•–‹‰ƒ–‡–Š‡…ƒ–ƒŽ›–‹…ƒ…–‹˜‹–›‘ˆ–Š‡•›–Š‡•‹œ‡†…ƒ–ƒǦ Ž›•–ǡ –Š‡ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ™‡”‡ —•‡† ‹ –Š‡ •›–Š‡•‹• ‘ˆ ƒ”›Ž‹†‡‡„ƒ”„‹–—”‹…ƒ…‹††‡”‹˜ƒ–‹˜‡•Ǥ ‘•–—†›–Š‡‡ˆˆ‹…‹‡…›‘ˆ–Š‡‘ ‡ʹͶƒ‘…ƒ–ƒŽ›•–ǡ„‡œƒŽǦ †‡Š›†‡ ȋ1aȌ ƒ†„ƒ”„‹–—”‹…ƒ…‹†ȋ1bȌ ™‡”‡—•‡† ƒ•–Š‡‘†‡Ž •—„•–”ƒ–‡ȋƒ„Ž‡ͳȌǤŠ‡’”‘†—…–3a™ƒ•‘„–ƒ‹‡†‹ͶͲΨ›‹‡Ž† ‹ ͵ƒ–”‘‘–‡’‡”ƒ–—”‡ ™‹–Š ‘ ‡ʹͶȋͷ‘ŽΨȌƒ•–Š‡ …ƒ–ƒŽ›•– ȋƒ„Ž‡ ͳǡ ‡–”› ͳȌǤ Š‡ ›‹‡Ž† ‘ˆ 3a ‹…”‡ƒ•‡† –‘ ͻͶΨ —•‹‰ƒ™ƒ–‡”Ǧ‡–Šƒ‘ŽȋͳǣͳȌ‹š–—”‡ȋƒ„Ž‡ͳǡ‡–”›ͻȌǡ„—–‘–ŠǦ

NH

O

1a

85

O

CH

NH

TGA (%)

4

DTA (PV)

DTG (Pg/min)

CHO

6



3a

O

 ƒ–ƒŽ›•–ƒ‘—– ‘Ž˜‡– •‘Žƒ–‡† ȋ‘ŽΨȌ ›‹‡Ž†ȋΨȌ ͳ  ͷ  ͵ ͶͲ ʹ  ͷ –… Ͷͺ ͵  ͷ  ͷͲ ͸͹ Ͷ  ͷ ʹ ͷ  ͷ –  ͹ͻ ͺͷ ͸  ͷ ʹǣ– ȋͳǣ͵Ȍ ͺͻ ͹  ͷ ʹǣ– ȋͳǣʹȌ ͺ  ʹ ʹǣ– ȋͳǣͳȌ ͺͷ ͻͶ ͻ  ͷ ʹǣ– ȋͳǣͳȌ ͻͷ ͳͲ ͳͲ ʹǣ– ȋͳǣͳȌ ͳͳ ͳͷ ʹǣ– ȋͳǣͳȌ ͻͶ ͻʹ ͳʹ ʹͲ ʹǣ– ȋͳǣͳȌ ʹǣ– ȋͳǣͳȌ ͹Ͳ ͳ͵   ͷƒ ͳͶ Ȅ ʹǣ– ȋͳǣͳȌ ͷͲ ‡ƒ…–‹‘ …‘†‹–‹‘•ǣ 1a ȋͷ ‘ŽȌǡ 2a ȋͷ ‘ŽȌǡ …ƒ–ƒŽ›•– ȋͷ ‘ŽΨȌǡ •‘Ž˜‡–ȋͷŽȌǡ”‘‘–‡’‡”ƒ–—”‡Ǥ ƒ—Ž‘ ‡ʹͶǤ

2a

–”›

‡” •‘Ž˜‡–• †‹† ‘– ‰‹˜‡ „‡––‡” ”‡•—Ž–• ȋƒ„Ž‡ ͳǡ ‡–”‹‡• ͳȂͺȌǤ Š‹• ‹• „‡…ƒ—•‡ –Š‡ •‘Ž˜‡– ƒˆˆ‡…–• –Š‡ –”ƒ•‹–‹‘ •–ƒ–‡ǡ ƒ† ™Š‡’‘Žƒ”•—„•–”ƒ–‡•ƒ”‡—•‡†‹–Š‡•›–Š‡•‹•ǡ–Š‡–”ƒ•‹–‹‘ •–ƒ–‡ ‹• „‡––‡” •‘Ž˜ƒ–‡† ƒ† –Š‡ ”‡ƒ…–‹‘ ”ƒ–‡ ‹…”‡ƒ•‡•ǡ ™Š‹…Š ‹…”‡ƒ•‡•–Š‡’”‘†—…–›‹‡Ž†ȏͷ͹ǡͷͺȐǤ ‘’–‹‹œ‹‰–Š‡”‡ƒ…–‹‘ …‘†‹–‹‘•ǡ –Š‡ ƒ‘—– ‘ˆ …ƒ–ƒŽ›•– ™ƒ• –Š‡ ƒŒ‘” ˆƒ…–‘”Ǥ Š‡ ‘†‡Ž”‡ƒ…–‹‘™ƒ••–—†‹‡†—•‹‰ʹǡͷǡͳͲǡͳͷǡƒ†ʹͲ‘ŽΨ‘ˆ

Table2 ›–Š‡•‹•‘ˆ†‡”‹˜ƒ–‹˜‡•‘ˆƒ”›Ž‹†‡‡„ƒ”„‹–—”‹…ƒ…‹†ǡ3aȂ3nǡ‹–Š‡’”‡•‡…‡‘ˆ‘ ‡ʹͶƒ‘…ƒ–ƒŽ›•–Ǥ

O

O NH

NH O

Ar CHO

O

Ar CH

NH O 1a1n

NH O

2

3a3n



Ǥ’Ǥ ‹‡  •‘Žƒ–‡† –”› ” ”‘†—…–  ƒȋŠȂͳȌ ȋ‹Ȍ ›‹‡Ž†ȋΨȌ „•‡”˜‡† ͳ ͸ ͷ 3a Ͷ ͻͶ   ͳ͸͸͸Ǥ͹ ʹ͸ʹȂʹ͸Ͷ ʹ ͶǦŽ͸ Ͷ 3b ʹ ͻͳ   ͵͵͵͵Ǥ͵ ʹͻ͸Ȃʹͻͺ ͵ ʹǦŽ͸ Ͷ 3c ͷ ͺͻ ͳʹͷͲ ʹͷʹȂʹͷͶ 3d Ͷ ͺͺ   ͳ͸͸͸Ǥ͹ ʹͻ͹Ȃʹͻͻ Ͷ ͶǦ ͵͸ Ͷ ͷ ͶǦ ͸ Ͷ 3e ͷ ͺ͸ ͳʹͷͲ ε͵ʹͲ ͸ ͶǦȋ ͵Ȍʹ͸ Ͷ 3f ͵ ͻͲ ʹͲͲͲ ʹ͹͸ ͹ ͸ ͷ α  3g ʹ ͺ͹   ͵͵͵͵Ǥ͵ ʹ͸͸Ȃʹ͸ͺ ͺ —”›Ž 3h ͷ ͺͷ ͳʹͷͲ ͵ͲͲȂ͵Ͳʹ ͻ ͷǦ‡Ǧ —”›Ž 3i ͸ ͺ͸ ͳͲͲͲ ʹͻͲȂʹͻʹ 3j ͵ ͺͲ ʹͲͲͲ ʹ͵ͺȂʹͶͳ ͳͲ ͵Ǧʹ͸ Ͷ ͳͳ ͵ǡͶǦȋ ͵Ȍʹ͸ ͵ 3k ͵ ͺ͹ ʹͲͲͲ ε͵ͲͲ ͳʹ ȽǦ‡Ǧ͸ Ͷ α  3l ʹ ͺʹ   ͳ͸͸͸Ǥ͹ ͳ͸ʹȂͳ͸Ͷ ͳ͵ †‘Ž‡Ǧ͵Ǧ…ƒ”„‘š›ƒŽ†‡Š›†‡ 3m ͷ ͺʹ ͳʹͷͲ ε͵ʹͲ ͳͶ ›”‹‰ƒŽ†‡Š›†‡ 3n Ͷ ͺͺ   ͳ͸͸͸Ǥ͹ ͵ͳͷȂ͵ͳͺ ‡ƒ…–‹‘…‘†‹–‹‘•ǣƒŽ†‡Š›†‡ȋͷ‘ŽȌǡ„ƒ”„‹–—”‹…ƒ…‹†ȋͷ‘ŽȌǡ‘ ‡ʹͶȋͷ‘ŽΨȌǡ™ƒ–‡”Ǧ‡–Šƒ‘ŽȋͳǣͳȌͷŽǡ”‘‘–‡’‡”ƒ–—”‡Ǥ ƒ—”‘˜‡”ˆ”‡“—‡…›ȋ‘Ž‡•‘ˆ”‡ƒ…–ƒ–…‘˜‡”–‡†Ȁȋ‘Ž‡•‘ˆ…ƒ–ƒŽ›•–έ”‡ƒ…–‹‘–‹‡ȌȌǤ 

‡’‘”–‡† ʹ͸͵Ȃʹ͸ͷ ʹͻͺǤͷ ʹͷͶ ʹͻͺȂ͵ͲͲ Ȅ ʹ͹ͶȂʹ͹͸ ʹ͹Ͳ ʹͷ͹Ȃʹͷͻ Ȅ ʹͶͺȂʹͷͲ εʹͻͲ ʹʹͺȂʹʹͻ Ȅ Ȅ



JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704

CoFe2O4

O H

NH

H

NH

O H O

O

O H

O

Deprotonation

O

Aldol

O O

NH O NH

H

NH

OH

NH O

O

Magnet

H O

O

NH

(a)

H

NH

O H

NH

H

NH

OH

NH

O

(b)

NH

Fig. 9. ‹•’‡”•‹‘ ‘ˆ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ‹ ™ƒ–‡”Ǧ‡–Šƒ‘Ž ͳǣͳ ‹šǦ –—”‡ȋƒȌƒ†ƒ‰‡–‹…•‡’ƒ”ƒ–‹‘‘ˆ…ƒ–ƒŽ›•–ȋ„ȌǤ  

…ƒ–ƒŽ›•–Ǥˆ–Š‡•‡ǡͷ‘ŽΨ‘ˆ…ƒ–ƒŽ›•–™ƒ•ˆ‘—†–‘„‡–Š‡‘’–‹Ǧ —ƒ‘—–ˆ‘”–Š‡”‡ƒ…–‹‘ȋƒ„Ž‡ͳǡ‡–”›ͻȌǢ™Š‡–Š‡…ƒ–Ǧ ƒŽ›•–Ž‘ƒ†‹‰™ƒ•Ž‡••–Šƒͷ‘ŽΨǡ–Š‡›‹‡Ž††‡…”‡ƒ•‡†•‹‰‹ˆ‹Ǧ …ƒ–Ž› ȋƒ„Ž‡ ͳǡ ‡–”› ͺȌǡ „—– ‹…”‡ƒ•‹‰ –Š‡ …ƒ–ƒŽ›•– Ž‘ƒ†‹‰ ƒ„‘˜‡ ͷ ‘ŽΨ †‹† ‘– ‹’”‘˜‡ –Š‡ ›‹‡Ž† ȋƒ„Ž‡ ͳǡ ‡–”‹‡• ͳͲȂͳʹȌǤ  –Š‡ ƒ„•‡…‡ ‘ˆ –Š‡ …ƒ–ƒŽ›•–ǡ ‘Ž› ƒ –”ƒ…‡ ƒ‘—– ‘ˆ –Š‡ ’”‘†—…– ™ƒ• ‘„–ƒ‹‡† ȋƒ„Ž‡ ͳǡ –”› ͳͶȌǤ Š‡ ”‡ƒ…–‹‘ ™ƒ• …ƒ””‹‡†‘—–—•‹‰„—Ž‘ ‡ʹͶ„—––Š‡›‹‡Ž†™ƒ•‘Ž›͹ͲΨȋƒǦ „Ž‡ ͳǡ ‡–”› ͳ͵Ȍǡ …‘’ƒ”‡† ™‹–Š ͻͶΨ —•‹‰ –Š‡ ƒ‘…ƒ–ƒŽ›•– ȋƒ„Ž‡ͳǡ‡–”›ͻȌǤ †‡” –Š‡ ‘’–‹‹œ‡† ”‡ƒ…–‹‘ …‘†‹–‹‘•ǡ ƒ •‡”‹‡• ‘ˆ ƒŽ†‡Ǧ Š›†‡•™ƒ•‹˜‡•–‹‰ƒ–‡†–‘‡•–ƒ„Ž‹•Š–Š‡•…‘’‡ƒ†Ž‹‹–ƒ–‹‘•‘ˆ –Š‹••›–Š‡•‹•ȋƒ„Ž‡ʹȌǤŠ‡”‡ƒ…–‹‘™ƒ•‡š–‡†‡†—•‹‰˜ƒ”‹Ǧ ‘—•ƒŽ†‡Š›†‡•ǡƒ‡Ž›Š‡–‡”‘ƒ–‘ƒŽ†‡Š›†‡•ȋƒ„Ž‡ʹǡ‡–”‹‡• ͺǡͻƒ†ͳ͵Ȍǡ—•ƒ–—”ƒ–‡†ƒŽ†‡Š›†‡•ȋƒ„Ž‡ʹǡ‡–”‹‡•͹ƒ†ͳʹȌǡ ƒ†ƒŽ†‡Š›†‡•™‹–Š‡Ž‡…–”‘Ǧ™‹–Š†”ƒ™‹‰‘”‡Ž‡…–”‘Ǧ†‘ƒ–‹‰ •—„•–‹–—‡–•ƒ––Š‡orthoǡmetaǡƒ†para’‘•‹–‹‘•ǢƒŽŽ–Š‡•‡ ƒŽ†‡Š›†‡•‰ƒ˜‡–Š‡†‡•‹”‡†’”‘†—…–•‹‰‘‘†–‘‡š…‡ŽŽ‡–›‹‡Ž†• ȋƒ„Ž‡ʹǡ‡–”‹‡•ʹȂͳͶȌǤŠ‡”‡ƒ…–‹‘•™‡”‡…Ž‡ƒǡƒ†…‘’Ž‡Ǧ –‹‘ ‘ˆ –Š‡ ”‡ƒ…–‹‘ ™ƒ• ‘‹–‘”‡† „› ˆ‘”ƒ–‹‘ ‘ˆ ƒ …‘Ž‘”‡† ’”‘†—…–Ǥˆ–‡”–Š‡”‡ƒ…–‹‘™ƒ•…‘’Ž‡–‡ǡ–Š‡…ƒ–ƒŽ›•–™ƒ••‡’Ǧ ƒ”ƒ–‡†‘—–ˆ”‘–Š‡”‡ƒ…–‹‘‹š–—”‡—•‹‰ƒ‡š–‡”ƒŽƒ‰‡– ȋ ‹‰Ǥ ͻȌǤ Š‡ ’”‘†—…–• ™‡”‡ ’—”‹ˆ‹‡† „› ”‡…”›•–ƒŽŽ‹œƒ–‹‘ ƒ†

O

O Dehydration H2O

O

Scheme 1. ”‘’‘•‡† ‡…Šƒ‹• ˆ‘” •›–Š‡•‹• ‘ˆ ƒ”›Ž‹†‡‡ „ƒ”„‹–—”‹… ƒ…‹†3a—•‹‰‘ ‡ʹͶƒ‘…ƒ–ƒŽ›•–Ǥ

…Šƒ”ƒ…–‡”‹œ‡† —•‹‰ Ǧ  ƒ† ͳ Ǧ •’‡…–”‘•…‘’‹‡•Ǥ Š‡ ’”‘†—…–• ™‡”‡ ˆ‘”‡† ™‹–Š ‰‘‘† …Š‡‘•‡Ž‡…–‹˜‹–› ƒ† ‘ •‹†‡Ǧ’”‘†—…–ˆ‘”ƒ–‹‘™ƒ•‘„•‡”˜‡††—”‹‰–Š‡•›–Š‡•‹•ǤŠ‡ •›–Š‡–‹… ’”‘–‘…‘Ž Šƒ• ‰‘‘† –—”‘˜‡” ˆ”‡“—‡…‹‡• ȋͳͲͲͲȂͳ͸͸͸Ǥ͹ŠΫͳȌȋƒ„Ž‡ʹȌǤŠ‡‡™‹•„ƒ•‹…•‹–‡•‹–Š‡…‘„ƒŽ– ˆ‡””‹–‡ ƒ‘’ƒ”–‹…Ž‡• ƒ”‡ ”‡•’‘•‹„Ž‡ ˆ‘” –Š‡ ’”‡•‡– ‘”‰ƒ‹… –”ƒ•ˆ‘”ƒ–‹‘ǤŠ‡‡™‹•„ƒ•‹…•‹–‡•‘”‹‰‹ƒ–‡ˆ”‘‡Ž‡…–”‘• –”ƒ’’‡†‹‹–”‹•‹…†‡ˆ‡…–•ǡˆ”‘•—”ˆƒ…‡Š›†”‘š›Ž‰”‘—’•ȏͷͻȐǡ ‘”ˆ”‘…‘‘”†‹ƒ–‹˜‡Ž›—•ƒ–—”ƒ–‡†‘š‹†‡‹‘•ƒ••‘…‹ƒ–‡†™‹–Š ‡‹‰Š„‘”‹‰Š›†”‘š›Ž‰”‘—’•ȏ͸ͲȐǤ’”‘’‘•‡†‡…Šƒ‹•ˆ‘” –Š‡”‡ƒ…–‹‘‹•‰‹˜‡‹…Š‡‡ͳǤ ”›Ž‹†‡‡ „ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡• Šƒ˜‡ ’”‡˜‹‘—•Ž› „‡‡ •›–Š‡•‹œ‡† —•‹‰ ˜ƒ”‹‘—• ‡–Š‘†•ǡ „—– –Š‡•‡ ‡–Š‘†• ‡‹–Š‡” ‰ƒ˜‡Ž‘™›‹‡Ž†•‘”‹˜‘Ž˜‡†…‘’Ž‡š”‡ƒ…–‹‘…‘†‹–‹‘•ȋƒ„Ž‡ ͵ȌǤŠ‡’”‡•‡–‡–Š‘†‹•‡ˆˆ‹…‹‡–ƒ†–Š‡…ƒ–ƒŽ›•–—•‡†‹•ƒ ‡š…‡ŽŽ‡–…ƒ–ƒŽ›•–Ǥ 3.3.  Recoveryandreusabilityofcatalyst ‡ ƒ†˜ƒ–ƒ‰‡ ‘ˆ ‘ ‡ʹͶ ƒ‘’ƒ”–‹…Ž‡• ‹• –Š‡‹” ƒ„‹Ž‹–› –‘ ƒ…– ƒ• Š‡–‡”‘‰‡‡‘—• ”‡…›…Žƒ„Ž‡ ”‡ƒ…–‹‘ •›•–‡•Ǥ ˆ–‡” …‘Ǧ ’Ž‡–‹‘ ‘ˆ –Š‡ ”‡ƒ…–‹‘ „‡–™‡‡ „‡œƒŽ†‡Š›†‡ ƒ† „ƒ”„‹–—”‹… ƒ…‹†ǡ –Š‡ …ƒ–ƒŽ›•– ™ƒ• •‡’ƒ”ƒ–‡† “—ƒ–‹–ƒ–‹˜‡Ž› ȋε ͻ͹ΨȌ ˆ”‘ –Š‡ ”‡ƒ…–‹‘ ‹š–—”‡ —•‹‰ ƒ ƒ‰‡–‹… •‡’ƒ”ƒ–‘” ƒ† –Š‡

Table3 ›–Š‡•‹•‘ˆƒ”›Ž‹†‡‡„ƒ”„‹–—”‹…ƒ…‹††‡”‹˜ƒ–‹˜‡•‹’”‡•‡…‡‘ˆ†‹ˆˆ‡”‡–…ƒ–ƒŽ›•–•Ǥ

O

O

NH

NH R CHO

O NH O

‘Ǥ ͳ ʹ ͵ Ͷ ͷ ͸ ͹ ͺ ͻ ͳͲ ͳͳ ͳʹ

—„•–”ƒ–‡ȋǦ Ȍ ͸ ͷ  ͸ ͷ  ͸ ͷ  ͸ ͷ  ͵Ǧʹ͸ Ͷ  ͸ ͷ  †‘Ž‡Ǧ͵Ǧ…ƒ”„‘š›ƒŽ†‡Š›†‡ ͶǦŽ͸ Ͷ  ͶǦŽ͸ Ͷ  ͸ ͷ  ͸ ͷ  ͸ ͷ 

ƒ–ƒŽ›•– ‡ͳ‰x”ͳǦxʹ ‹ƒ‘’ƒ”–‹…Ž‡• ƒ•‹…ƒŽ—‹ƒ ‹ʹȉͳʹ͵ȉʹͶ ʹ  ʹ͵   ͶǦ…Ȁ…  Ǧ’”‘Ž‹‡ ‹Ž͵   …Žƒ› ƒŽ ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•

O

R CH NH O

 ‡ƒ…–‹‘…‘†‹–‹‘ ‘Ž˜‡–ˆ”‡‡ǡǡͶͷͲȀ͵‹ –Š›Ž‡‡‰Ž›…‘ŽǡͷͲ‘ȀͳͲȂͳͷ‹ ‘Ž˜‡–ˆ”‡‡ǡǡ͹ͲͲȀͷ‹ ƒ–‡”ǡ—Ž–”ƒ•‘—†ȀͳͲ‹

”‹†‹‰ȀͳͲ‹ ǡͷ͸ͲȀ͹‹ –Šƒ‘Žǡ͸Ͳ‘Ȁ͵ǤͷŠ ǤǤȀ͵Ͳ‹ ƒ–‡”ǡ͹Ͳ‘ȀʹŠ ǡͷ͸ͲȀ͹‹ ǡͷ͸ͲȀ͹‹ “Ǥ‡–Šƒ‘ŽȀǤǤȀͶ‹

‹‡Ž†ȋΨȌ ͻͲ ͻͳ ͻͲ ͸ͳ Ͷ͹ ͷʹ ͸Ͳ ͺͷ ͺͶ ͹Ͳ ͸ͺ ͻͶ

‡ˆǤ ȏ͵ͻȐ ȏ͵͸Ȑ ȏ͵ʹȐ ȏͶͳȐ ȏ͵ͷȐ ȏ͵ͷȐ ȏ͵͹Ȑ ȏ͵ͺȐ ȏͶʹȐ ȏ͵͵Ȑ ȏ͵͵Ȑ –Š‹•™‘”



JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704

Product yield Catalyst isolated

100

Yield (%)

96

ȏ͸Ȑ ƒ™ƒ—”ƒǡƒ–‘ǤChemCommunǡʹͲͲ͸ǣͶ͹ͳͺ ȏ͹Ȑ Šƒǡ ‹ŽŽǡ‰—›‡ ǡŠƒ‰ ǡ ‘‡•ǤAngewChem

IntEdǡʹͲͲ͸ǡͶͷǣʹʹͲͻ ȏͺȐ •…Š™ƒ†‡ ǡ ƒ‡ŽŽƒ ǡ ‘••„ƒ…Š ǡ ‡ŽŽ‡” ǡ ƒ‹‡” Ǥ Chem ȏͻȐ ȏͳͲȐ ȏͳͳȐ ȏͳʹȐ ȏͳ͵Ȑ ȏͳͶȐ

92 88 84

ȏͳͷȐ

1

2

3 4 Number of cycles

5

6

Fig.10.Š‡”‡…›…Žƒ„‹Ž‹–›‘ˆ‘ ‡ʹͶƒ‘’ƒ”–‹…Ž‡•ˆ‘”•›–Š‡•‹•‘ˆ3aǤ

™ƒ•Š‡†™‹–Š‡–Šƒ‘Žǡˆ‘ŽŽ‘™‡†„›†”›‹‰ƒ–͹Ͳιˆ‘”ͳŠǤŠ‡ ƒ‘’ƒ”–‹…Ž‡•™‡”‡”‡—•‡†•‹š–‹‡•ˆ‘”–Š‡•›–Š‡•‹•‘ˆƒ”›Ž‹Ǧ †‡‡ „ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡• ™‹–Š‘—– •‹‰‹ˆ‹…ƒ– Ž‘•• ‘ˆ ƒ…Ǧ –‹˜‹–›Ǥ Š‡ …ƒ–ƒŽ›–‹… ’‡”ˆ‘”ƒ…‡ ‘ˆ ‘ ‡ʹͶ ™ƒ• ˆ‘—† –‘ „‡ —ƒŽ–‡”‡†ȋ—’–‘•‹š…‘•‡…—–‹˜‡…›…Ž‡•ȌǤŠ‹•‡–Š‘†‹•’‘–‡Ǧ –‹ƒŽŽ›ƒ‹’‘”–ƒ–’”‘–‘…‘Žˆ‘”Žƒ”‰‡Ǧ•…ƒŽ‡•›–Š‡•‹•ǤŠ‡”‡…›Ǧ …Ž‹‰”‡•—Ž–•ƒ”‡•Š‘™‹ ‹‰ǤͳͲǤ 4.  Conclusions Š‡’”‡•‡–’”‘–‘…‘ŽŠ‹‰ŠŽ‹‰Š–•–Š‡—•‡‘ˆ‘ ‡ʹͶƒ‘’ƒ”Ǧ –‹…Ž‡• ƒ• ƒ ‰”‡‡ǡ ‹‡š’‡•‹˜‡ǡ ‡ˆˆ‹…‹‡–ǡ •‹’Ž‡ǡ ‘Ǧ–‘š‹…ǡ ƒ† ”‡…‘˜‡”ƒ„Ž‡ …ƒ–ƒŽ›•– ˆ‘” –Š‡ •›–Š‡•‹• ‘ˆ ƒ”›Ž‹†‡‡ „ƒ”„‹–—”‹… ƒ…‹† †‡”‹˜ƒ–‹˜‡•Ǥ Š‡ •›–Š‡•‹œ‡† •’‹‡ŽǦ•Šƒ’‡† ‘ ‡ʹͶ ƒǦ ‘’ƒ”–‹…Ž‡•Šƒ˜‡ƒ†˜ƒ–ƒ‰‡‘—•’”‘’‡”–‹‡••—…Šƒ•ƒ•ƒŽŽ’ƒ”Ǧ –‹…Ž‡ •‹œ‡ ȋʹȂͺ Ȍǡ Š‹‰Š •—”ˆƒ…‡ ƒ”‡ƒǡ ƒ† ƒ ƒ‰‡–‹… ƒ–—”‡ǡ ™Š‹…Šƒ‡–Š‡ƒ‡š…‡ŽŽ‡–…ƒ–ƒŽ›•–ˆ‘”–Š‡’”‡•‡–•›–Š‡–‹… ’”‘–‘…‘ŽǤ Š‡ ƒ––”ƒ…–‹˜‡ ˆ‡ƒ–—”‡• ‘ˆ –Š‹• •›–Š‡•‹• ƒ”‡ ƒ •Š‘”– ”‡ƒ…–‹‘ –‹‡ǡ Š‹‰Š –—”‘˜‡” ˆ”‡“—‡…›ǡ •‹’Ž‡ ™‘”Ǧ—’ ’”‘Ǧ …‡••ǡƒ…Ž‡ƒ”‡ƒ…–‹‘ǡ‘Ǧ–‘š‹…”‡ƒ‰‡–•ǡƒƒ“—‡‘—•‡†‹—ǡ ”‡…‘˜‡”›Ȁ”‡…›…Žƒ„‹Ž‹–› ‘ˆ –Š‡ …ƒ–ƒŽ›•–ǡ ‡…‘ˆ”‹‡†Ž› •›–Š‡•‹•ǡ ƒ†‡š…‡ŽŽ‡–›‹‡Ž†•‘ˆ’”‘†—…–•ǡƒ‹‰‹–ƒ‡š…‡ŽŽ‡–ƒŽ–‡”ƒǦ –‹˜‡–‘‘–Š‡””‡’‘”–‡†’”‘–‘…‘Ž•Ǥ Acknowledgments

ȏͳ͸Ȑ ȏͳ͹Ȑ ȏͳͺȐ ȏͳͻȐ ȏʹͲȐ ȏʹͳȐ ȏʹʹȐ ȏʹ͵Ȑ ȏʹͶȐ ȏʹͷȐ ȏʹ͸Ȑ ȏʹ͹Ȑ ȏʹͺȐ ȏʹͻȐ ȏ͵ͲȐ ȏ͵ͳȐ ȏ͵ʹȐ ȏ͵͵Ȑ

‡ ƒ”‡ –Šƒˆ—Ž –‘  ǡ ƒŒƒ„ ‹˜‡”•‹–› Šƒ†‹‰ƒ”Š ˆ‘” Ǧ ǡǡͳ Ǧǡƒ†ͳ͵Ǧǡ ‘’ƒ”ˆ‘”ƒ†ǡ   ‘‘”‡‡ˆ‘”ǡƒ† ƒ•Š‡†’—”ˆ‘”Ǥ‡‘ˆ –Š‡ ƒ—–Š‘”• ȋ ǤǤȌ ‹• –Šƒˆ—Ž –‘   ƒ†   ƒŽƒ†Šƒ” ˆ‘” ’”‘˜‹†‹‰–Š‡”‡•‡ƒ”…Šˆ‡ŽŽ‘™•Š‹’Ǥ

ȏ͵ͶȐ ȏ͵ͷȐ ȏ͵͸Ȑ ȏ͵͹Ȑ

References

ȏ͵ͻȐ

ȏͳȐ ƒ•–ƒ•  ǡ ƒ”‡”  Ǥ ”‡‡ Š‡‹•–”›ǣ Š‡‘”› ƒ† ”ƒ…–‹…‡Ǥ ȏʹȐ ȏ͵Ȑ ȏͶȐ ȏͷȐ

šˆ‘”†ǣšˆ‘”†‹˜‡”•‹–›ǡͳͻͻͺ

—‹ǡƒ”—™ƒ–‹ǡƒ‘”ƒƒǤOrgLettǡʹͲͲ͹ǡͻǣͳͶͳͻ — ǡ‡‰ ǤJAmChemSocǡʹͲͲʹǡͳʹͶǣͺʹͲͶ ƒ–Šƒ ǡ‹ŽŽ‹ƒ•ǤAccChemResǡʹͲͲͺǡͶͳǣͶͳͳ ƒ—”‡–ǡ ‘”‰‡ǡ‘”–ǡ‘…Šǡ‘„‹…ǡŽ•–ǡ—ŽŽ‡”Ǥ ChemRevǡʹͲͲͺǡͳͲͺǣʹͲ͸Ͷ



ȏ͵ͺȐ

ȏͶͲȐ ȏͶͳȐ ȏͶʹȐ ȏͶ͵Ȑ ȏͶͶȐ

CatChemǡʹͲͲͻǡͳǣͳͳͳ Šƒ‰ǡ‹ƒ ǤApplCatalAǡʹͲͲͻǡ͵͸͸ǣͳͶͳ

‹ŽŽǡ‘‰ǡ ‘‡•ǤCatalLettǡʹͲͲͻǡͳ͵ͳǣͶʹͷ ‹ ǡŠƒ‰ǡ ƒ ǡ ƒ‘ǡ‹ǤJMolCatalAǡʹͲͲͻǡʹͻͺǣ͵ͳ …ŠÚ–œǡ ƒ‰‡”ǡ‡‹•‡”ǤAdvFunctMaterǡʹͲͲͻǡͳͻǣʹͳͲͻ ‘Ž•Š‡––‹™ƒ”ǡƒ”ƒǤTetrahedronǡʹͲͳͲǡ͸͸ǣͳͲͻͳ ƒ‰ƒƒ–Š  ǡ Ž‘‡•‰‡• ǡ…Š¡ˆ‡” ǡ Ž‘”‹—• Ǥ Angew Chem IntEdǡʹͲͳͲǡͶͻǣ͹͹ͺ͸ ƒ–‘ —”–‡ŽŽ‹ ǡ —‘‰  ǡ —‡• ǡ ”‘‡••‹‰‡” ǡ ‘„‡Ž Ǥ J MagnMagnMaterǡʹͲͲͺǡ͵ʹͲǣ‡͵͵ͻ —”†‘… ǡ ‹‘• ǡ ƒ˜‹†•‘ǤIEEE Trans Magnǡͳͻͻʹǡ ʹͺǣ͵Ͳ͹ͺ Šƒˆ‹    ǡ ‡†ƒ‡ ǡ ”‘œ‘”‘˜ ǡ ƒŽ‘‰Š Ǥ Chem Materǡ ͳͻͻͺǡͳͲǣ͵ͶͶͷ ‹—ǡ‘†‹‘‡ ǡŠƒ‰ ǤPureApplChemǡʹͲͲͲǡ͹ʹǣ͵͹ ƒ‰ ǡŠƒ‰ǡƒ‰ǡ‹— ǤChemLettǡʹͲͲͶǡ͵͵ǣͺʹ͸ Ž••‘ǡƒŽƒœƒ”ǦŽ˜ƒ”‡œ ǡ ‡†‡“˜‹•–ǡ ‡††‡ǡ‹†Ǧ „‡”‰ ǡƒ˜ƒ‰‡ ǤChemMaterǡʹͲͲͷǡͳ͹ǣͷͳͲͻ Šƒ––ƒ…Šƒ”››ƒǡƒŽ˜‡–ƒ– ǡ Ž‡—”‹‡”ǡ —•ƒǡƒ……‹ƒ‰—‡””ƒ ǡƒ„‘—‰‹ǤChemCommunǡʹͲͲͷǣͶͺͳͺ — ǡ‡‰ ǡ‘„‹•‘ǡƒ‘—šǡ‹…‡ǡƒ‰ǡ‹ Ǥ JAmChemSocǡʹͲͲͶǡͳʹ͸ǣʹ͹͵ ‹Ž—ƒ”ǡŠ”‘–”‹  ǡ—Žƒ”‹ǡ‡•Š’ƒ†‡ǡƒ–‡Ǥ MaterLettǡͳͻͻ͸ǡʹ͹ǣʹͻ͵ ‘’›ƒ ǡ†œŠ‹„‡›ƒǡƒ”„‹›ƒ ǡ—ƒ•›ƒǤBiol ZhArmǡͳͻ͹͸ǡʹͻǣͺͲǢChemAbstrǡͳͻ͹͸ǡͺͷǣ͹ʹͲ͸ͺˆ  Šƒƒ„ƒ ǡ‘Š•‡ǡƒ”ǡƒŠƒ”ƒǤ SciPharmǡͳͻͺͶǣ ͷʹǢChemAbstrǡͳͻͺͶǡͳͲͳǣ͹ͷ͸͹͹ƒ

—”•‹…ǤJHeterocyclChemǡʹͲͲͳǡ͵ͺǣ͸ͷͷ ”ƒ‰‹ǡ —‹„ƒŽǡ‹••‘…“ ǡƒƒ”Ž‹ ǤSynthesisǡͳͻͺ͸ǡͳʹǣ ͳͲͶ͸ ‘Œƒ”•‹ ǡ‘”‘•œ ǡƒ”–‘  ǡƒŽ—…Š‘™•ƒ ǤAdvHeter ocyclChemǡͳͻͺͷǡ͵ͺǣʹʹͻ ‹‰—‡”‘ƒǦ‹ŽŽƒ”  ǡ”—œǡ —…‹ƒ†‘•ƒ–‘•Ǥ Synth Communǡ ͳͻͻʹǡʹʹǣͳͳͷͻ ‡†ƒ ǡ ƒ™ƒ„‡ ǡ ƒƒ‹ ǡ ƒ™ƒ•ƒ‹ Ǥ Chem Lettǡ ͳͻͺͻǡ ͳͺǣ ͳͺͲ͵ ‡œ‡†‡  ǡ ƒ’‘†‘‹…‘ ǡ „—‹ ǡ ‘••ƒ›‹ Ǥ Spectrochim ActaPartAǡʹͲͲͳǡͷ͹ǣͳͳͺ͵ ŠƒŽƒˆ‹Ǧ‡œŠƒ†ǡ ƒ•Š‡‹ǤIranJChemChemEngǡʹͲͲͳǡʹͲǣͻ Ž…‡””‡…ƒ ǡƒƒ„”‹ƒǡ‹”ƒ†ƒǡ””‘›‘ ǡƒƒ”‹œ ǡ‡Ž‰ƒ†‘ Ǥ SynthCommunǡʹͲͲͲǡ͵Ͳǣͳʹͻͷ ‡™ƒǡ‹‰ŠǤSynthCommunǡʹͲͲ͵ǡ͵͵ǣ͵Ͳͺͳ ‹ ǡƒ‹  ǡ‹—ǡ‹ǤSynthCommunǡʹͲͲ͸ǡ͵͸ǣ͹ͺͻ Š—”ƒƒ ǡ‹ŒǤCatalLettǡʹͲͳͲǡͳ͵ͺǣͳͲͶ

ƒ‹ǡŠ‹‹”‡††›ǡ‘Ž‹•‡––›ǤIntJChemTechResǡʹͲͳͳǡ͵ǣ ͺͳ͹  ŠƒǡŽ‹ǡ ƒ”‘‘“—‹ǡŠƒǡƒŠƒǡǡ‡”˜‡‡ǤJChem SocPakǡʹͲͲͻǡ͵ͳǣͺʹ͵ ƒ–Š‘†  ǡ ƒ„Š‹”‡  ǡ ”„ƒ†  ǡ ƒ†‡  Ǥ Bull Korean ChemSocǡʹͲͳͲǡ͵ͳǣ͵͵ͻ ƒ‰ǡƒ  ǡŠ‘—ǡƒ‰ ǡƒ‰ǡ ƒ‘ ǡ—‹ǤSynth CommunǡʹͲͲͷǡ͵ͷǣʹ͹ͷͻ ‹ ǡ—ǤAustJChemǡʹͲͲͻǡ͸ʹǣ͵ͷ͵ Š‹  ǡ Š‡ ǡ Š—‰  ǡ ƒ‰  ǡ —  Ǥ Chin Chem Lettǡ ʹͲͲ͵ǡͳͶǣͳʹͶʹ ƒŒ’—– ǡƒ—” ǤTetrahedronLettǡʹͲͳʹǡͷ͵ǣ͸Ͷ͸ Šƒ”ƒǡƒŒ’—– ǡƒ‹–Šǡƒ—”ǡŠƒ”ƒǤThinSolidFilmsǡ



JaspreetKaurRajputetal./ChineseJournalofCatalysis34(2013)1697–1704 

GraphicalAbstract Chin.J.Catal.ǡʹͲͳ͵ǡ͵Ͷǣͳ͸ͻ͹Ȃͳ͹ͲͶ   †‘‹ǣͳͲǤͳͲͳ͸Ȁͳͺ͹ʹǦʹͲ͸͹ȋͳʹȌ͸Ͳ͸Ͷ͸Ǧͻ CoFe2O4nanoparticles:Anefficientheterogeneousmagnetically  separablecatalystfor“click”synthesisofarylidenebarbituric  acidderivativesatroomtemperature

ƒ•’”‡‡–ƒ—”ƒŒ’—–ȗǡ ƒ‰ƒ†‡‡’ƒ—” Dr.B.R.AmbedkarNationalInstituteofTechnology,Jalandhar,India

CoFe2 O4

O



ArCHO

O

NH

+

NH

O NH

 ‡ˆˆ‹…‹‡– ’”‘–‘…‘Ž ˆ‘” –Š‡ Dz…Ž‹…dz •›–Š‡•‹• ‘ˆ ƒ”›Ž‹†‡‡ „ƒ”„‹–—”‹… ƒ…‹††‡”‹˜ƒ–‹˜‡•—•‹‰ƒŠ‡–‡”‘‰‡‡‘—•ƒ‰‡–‹…ƒŽŽ›•‡’ƒ”ƒ„Ž‡‘ ‡ʹͶ ƒ‘…ƒ–ƒŽ›•– ‹• ’”‡•‡–‡†Ǥ Š‡ •›–Š‡•‹• ‹• •‹’Ž‡ǡ …Ž‡ƒǡ ƒ† ‡…‘Ǧ ˆ”‹‡†Ž›Ǥ

O

O

ArCH NH

RT, 5 mol% R.T. 82% 94%

O





 ʹͲͳͲǡͷͳͻǣͳʹʹͶ ȏͶͷȐ Šƒ”ƒ ǡ Šƒ”ƒ ǡ ƒ‹–Š  ǡ ƒŒ’—– ǡ ƒ—” Ǥ Appl Surf Sciǡ

ʹͲͳͳǡʹͷ͹ǣͻ͸͸ͳ ȏͶ͸Ȑ ‘”‰‘Šƒ‹ ǡ ‡ƒ’ƒ–‹  ǡ ‹•Š”ƒ ǡ ƒ”ƒ  ǡ Š—ƒ Ǥ Na

noscaleǡʹͲͳͲǡʹǣʹʹͷͲ ȏͶ͹Ȑ ƒƒ—––› ǡ—‰—ƒǤApplCatalAǡʹͲͲͳǡʹͳͺǣ͵ͻ ȏͶͺȐ ƒ‘ǡ‹ ǤNanotechnologyǡʹͲͲͷǡͳ͸ǣͳͺͲ  ȏͶͻȐ ›‡‘ǡŠ—‰ǡƒ” ǡ‡‡ǡ‹ǡƒ” ǤJPhysChem

BǡʹͲͲʹǡͳͲ͸ǣ͸ͺ͵ͳ ȏͷͲȐ —ŽŽ‹–›  Ǥ Ž‡‡–• ‘ˆ Ǧƒ› ‹ˆˆ”ƒ…–‹‘Ǥ ‘†‘ǣ ††‹•‹‘ ‡•‡Ž›ǡͳͻͷͻǤʹ͸ͳ  ȏͷͳȐ ƒ•Šƒ†ǡ‘Šƒ‡†ǡ „”ƒŠ‹ǡ •ƒ‹Ž ǡ„†‡ŽǦƒŽ ǤAdvPowderTechnolǡʹͲͳʹǡʹ͵ǣ͵ͳͷ ȏͷʹȐ ƒ”–‹‡œ ǡ„”ƒ†‘”•ǡ ƒŽ…‡ŽŽ• ǡ‘—ƒ‡–ǡ ‘–›Ǥ PhysRev

LettǡͳͻͻͺǡͺͲǣͳͺͳ ȏͷ͵Ȑ ”‡‰ ǡ‹‰Ǥ†•‘”’–‹‘ǡ—”ˆƒ…‡”‡ƒǡƒ†‘”‘•‹–›Ǥ‡™

‘”ǣ…ƒ†‡‹…ǡͳͻͺʹ ȏͷͶȐ ‡ƒ’ƒ–‹ǡ‘”‰‘Šƒ‹ǡŠ—ƒǤJMolCatalAǡʹͲͳͳǡ͵͵ͻǣʹͶ ȏͷͷȐ ‹ƒ‘ ǡ ‡‰ ǡ —  ǡ ‹ƒ‰ ǡ Šƒ‘ Ǥ J Colloid Surf Aǡ ʹͲͲͺǡ

͵ͳ͵Ǧ͵ͳͶǣ͵ͳ ȏͷ͸Ȑ ‡ƒ’ƒ–‹  ǡ ‘› ǡ ‘”‰‘Šƒ‹ ǡ Š—ƒ Ǥ J Mol Catal Aǡ ʹͲͳʹǡ

͵ͷʹǣͳʹͺ ȏͷ͹Ȑ ƒ•…‘ ǡ –ƒ› ǡ ‡”ƒ†‡œǦŽ‘•‘  ǡ ˜ƒ Ž‹   ǡ

ƒ’–‡‹Œ ǤJCatalǡʹͲͲͻǡʹ͸ͳǣ͹ͷ ȏͷͺȐ ‘”ƒǡ „‘””ƒǡ‘†”‹‰—‡œ ǡƒ…Š‡œ ǤJCatalǡʹͲͲʹǡʹͳͳǣʹͲͺ ȏͷͻȐ ‡‰—”‘ǡ•—‹ǤJAdhesionSciTechnolǡͳͻͻͲǡͶǣ͵ͻ͵ ȏ͸ͲȐ ‘”†‹•…Š‹ ǡ †‘˜‹ƒ Ǥ J Chem Socǡ Faraday Trans Iǡ ͳͻ͹͸ǡ ͹ʹǣ

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