Sonication method synergism with rare earth based nanocatalyst:preparation of NiFe_(2–x)Eu_xO_4 nanostructures and its catalytic applications for the synthesis of benzimidazoles,benzoxazoles,and benzothiazoles under ultrasonic irradiation
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摘要
A simple and practical ultrasonically synthetic strategy for the preparation of rare-earth based catalyst, nanostructured NiFe_(2–x)Eu_xO_4 was developed. The structure of NiFe_(2–x)Eu_xO_4 was characterized by various analyses such as X-ray diffraction(XRD), scanning electron microscopy(SEM) and fourier transform infrared spectroscopy(FT-IR). The catalytic performance of NiFe_(2–x)Eu_xO_4 was evaluated for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles under ultrasonic irradiation. All reactions were completed in short times and all products were obtained in good to excellent yields in presence of the rare-earth based catalyst. Besides, NiFe_(2–x)Eu_xO_4 could be recovered for 6 times without noticeably decreasing the catalytic activity.
A simple and practical ultrasonically synthetic strategy for the preparation of rare-earth based catalyst, nanostructured NiFe_(2–x)Eu_xO_4 was developed. The structure of NiFe_(2–x)Eu_xO_4 was characterized by various analyses such as X-ray diffraction(XRD), scanning electron microscopy(SEM) and fourier transform infrared spectroscopy(FT-IR). The catalytic performance of NiFe_(2–x)Eu_xO_4 was evaluated for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles under ultrasonic irradiation. All reactions were completed in short times and all products were obtained in good to excellent yields in presence of the rare-earth based catalyst. Besides, NiFe_(2–x)Eu_xO_4 could be recovered for 6 times without noticeably decreasing the catalytic activity.
A simple and practical ultrasonically synthetic strategy for the preparation of rare-earth based catalyst, nanostructured NiFe_(2–x)Eu_xO_4 was developed. The structure of NiFe_(2–x)Eu_xO_4 was characterized by various analyses such as X-ray diffraction(XRD), scanning electron microscopy(SEM) and fourier transform infrared spectroscopy(FT-IR). The catalytic performance of NiFe_(2–x)Eu_xO_4 was evaluated for the synthesis of benzimidazoles, benzoxazoles and benzothiazoles under ultrasonic irradiation. All reactions were completed in short times and all products were obtained in good to excellent yields in presence of the rare-earth based catalyst. Besides, NiFe_(2–x)Eu_xO_4 could be recovered for 6 times without noticeably decreasing the catalytic activity.
引文
[1]Rahimi-Nasrabadi M,Pourmortazavi S M,Ganjali M R.Facile synthesis optimization and structure characterization of zinc tungstate nanoparticles.Mater.Manuf.Processes,2015,30:34.
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[3]Rahimi-Nasarabadi M,Ahmadi F,Hamdi S,Eslami N,Didehban K,Ganjali Ganjali M R.Preparation of nanosized chromium carbonate and chromium oxide green pigment through direct carbonation and precursor thermal decomposition.J.Mol.Liq.,2016,216:814.
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[6]Anastas P,Eghbali N.Green chemistry:principles and practice.Chem.Soc.Rev.,2010,39:301.
[7]Cravotto G,Cintas P.Power ultrasound in organic synthesis:moving cavitational chemistry from academia to innovative and large-scale applications.Chem.Soc.Rev.,2006,35:180.
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[9]Naghizadeh-Alamdari S,Habibi-Yangjeh A,Pirhashemi M.One-pot ultrasonic-assisted method for preparation of Ag/Ag Cl sensitized Zn O nanostructures as visible-light-driven photocatalysts.Solid State Sci.,2015,40:111.
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[19]Teimouri A,Chermahini A N,Salavati H,Ghorbanian L.An efficient and one-pot synthesis of benzimidazoles,benzoxazoles,benzothiazoles and quinoxalines catalyzed via nano-solid acid catalysts.J.Mol.Catal.A:Chem.,2013,373:38.
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[21]Bala M,Verma P K,Sharma D,Kumar N,Singh B.Highly efficient water-mediated approach to access benzazoles:metal catalyst and base-free synthesis of2-substituted benzimidazoles,benzoxazoles,and benzothiazoles.Mol.Divers,2015,19:263.
[22]Shelkar R,Sarode S,Nagarkar J.Nano ceria catalyzed synthesis of substituted benzimidazole,benzothiazole,and benzoxazole in aqueous media.Tetrahedron Lett.,2013,54:6986.
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[25]Raju B,Nguyen N,Holland G W.Solution-phase parallel synthesis of substituted benzimidazoles.J.Comb.Chem.,2002,4:320.
[26]Chen F,Shen C J,Yang D.A simple protocol for the synthesis of 2-arylbenzoxazoles by oxidation with o-iodoxybenzoic acid(IBX)and its application in the synthesis of arylbenzoxazole-containing amino acids.Tetrahedron Lett.,2011,52:2128.
[27]Leng W N,Zhou Y M,Xu Q H,Liu J Z.Synthesis and characterization of nonlinear optical side-chain polyimides containing the benzothiazole chromophores.Macromolecules,2001,34:4774.
[28]Hutchinson I,Jennings S A,Vishnuvajjala B R,Westwell A D,Stevens M F G.Antitumor benzothiazoles.16.1Synthesis and pharmaceutical properties of antitumor2-(4-aminophenyl)benzothiazole amino acid prodrugs.J.Med.Chem.,2002,45:744.
[29]Xu H X,Zeigera Brad W,Suslick Kenneth S.Sonochemical synthesis of nanomaterials.Chem.Soc.Rev.,2013,42:2555.
[30]Rahimi-Nasrabadi M,Rostami M,Ahmadi F,Fallah Shojaie A,Delavar Rafiee M.Synthesis and characterization of Zn Fe2-xYbxO4-graphene nanocomposites by sol-gel method.J.Mater.Sci.Mater.Electron.,2016,27:11940.
[31]Rahimi-Nasrabadi M,Behpour M,Sobhani-Nasab A,Rangraz Jeddy M.Nanocrystalline Ce-doped copper ferrite:synthesis,characterization,and its photocatalyst application.J.Mater.Sci.Mater.Electron,2016,27:11691.
[32]Gholinejad M,Karimi B,Mansouri F.Synthesis and characterization of magnetic copper ferrite nanoparticles and their catalytic performance in one-pot odorless carbon-sulfur bond formation reactions.J.Mol.Catal.A:Chem.,2014,386:20.
[33]Maleki B,Eshghi H,Khojastehnezhad A,Tayebee R,Ashrafi S S,Kahoo G E,Moeinpour F.Silica coated magnetic Ni Fe2O4 nanoparticle supported phosphomolybdic acid;synthesis,preparation and its application as a heterogeneous and recyclable catalyst for the one-pot synthesis of tri-and tetra-substituted imidazoles under solvent free conditions.RSC Adv.,2015,5:64850.
[34]Liu W J,Ke Tiana,Jiang H.One-pot synthesis of NiNi Fe2O4/carbon nanofiber composites from biomass for selective hydrogenation of aromatic nitro compounds.Green Chem.,2015,17:821.
[35]Gong M,Dai H.A mini review of Ni Fe-based materials as highly active oxygen evolution reaction electrocatalysts.Nano Res.,2015,8:23.
[36]Rahimi-Nasrabadi M,Pourmortazavi S M,Aghazadeh M,Ganjali M R,Sadeghpour K M,Novrouzi P.Samarium carbonate and samarium oxide:synthesis,characterization and eluation of the photo-catalytic behavior.J.Mater.Sci.Mater.Electron.,2017,28:5574.
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[38]Ji B F,Tian C A,Zhang Q Z,Ji D D,Yang J,Xie J S,Si JY.Magnetic properties of samarium and gadolinium codoping Mn-Zn ferrites obtained by sol-gel auto-combustion method.J.Rare Earths,2016,34:1017.
[39]Wang W H,Li W,Guo R T,Chen Q L,Wang Q S,Pan WG,Hy G X.A Ce Fe Ox catalyst for catalytic oxidation of NO to NO2.J.Rare Earths,2016,34:876.
[40]Liu S,Wu X D,Weng D,Ran R.Ceria-based catalysts for soot oxidation:a review.J.Rare Earths,2015,33:567.
[41]Pourmortazavi S M,Rahimi-Nasrabadi M,Fazli Y,Mohammad-Zadeh M.Taguchi method assisted optimization of electrochemical synthesis and structural characterization of copper tungstate nanoparticles.Int.J.Refract.Met.Hard Mater.,2015,51:29.
[42]Rahimi-Nasrabadi M,Behpour M,Sobhani-Nasab A,Hosseinpour-Mashkani S M.Zn Fe2-xLaxO4 nanostructure:synthesis,characterization,and its magnetic properties.J.Mater.Sci.Mater.Electron.,2015,26:9776.
[43]Pourmortazavi S M,Zaree A,Mirsadeghi S.Taguchi approach-assisted optimization of spraying in non-solvent process for preparation of potassium perchlorate nanoparticles.J.Sol-Gel Sci.Technol.,2015,76:510.
[44]Rahimi-Nasrabadi M,Pourmortazavi M,Davoudi-Dehaghani A A,Hajimirsadeghi S S,Zahedi M M.Synthesis and characterization of copper oxadate and copper oxide nanoparticles by statistically optimized controlled precipitation and calcination.Cryst.Eng.Comm.,2013,15:4077.
[45]Shamsipur M,Pourmortazavi S M,Roushani M,Kohsari I,Hajimirsadeghi S S.Novel approach for electrochemical preparation of sulfur nanoparticles.Microchim.Acta,2011,173:445.
[46]Rahimi-Nasrabadi M,Pourmortazavi S M,KhalilianShalamzari M,Hajimirsadeghi S S,Zahedi M M.Optimization of synthesis procedure and structure characterization of manganese tungstate nanoplates.Open Chem.,2013,11:1393.
[47]Rahimi-Nasrabadi M,Pourmortazavi S M,KhalilianShalamzari M.Facile chemical synthesis and structure characterization of copper molybdate nanoparticles.J.Mol.Struct.,2015,1083:229.
[48]Pourmortazavi S M,Taghdiri M,Makari V,Rahimi-Nasrabadi M.Procedure optimization for green synthesis of silver nanoparticles by aqueous extract of Eucalyptus oleosa.Spectrochim.Acta A:Mol.Biomol.Spectrosc.,2015,136:1249.
[49]Pourmortazavi S M,Rahimi-Nasrabadi M,Hajimirsadeghi S S.Applying the taguchi robust design to optimization of the experimental conditions for synthesis of lead chromate nanorods.J.Dispersion Sci.Technol.,2012,33:254.
[50]Pourmortazavi S M,Rahimi-Nasrabadi M,KhalilianShalamzari M,Ghaeni H R,Hajimirsadeghi S S.Facile chemical synthesis and characterization of copper tungstate nanoparticles,J.Inorganic Organomet.Polym.Mater.,2014,24:333.
[51]Pourmortazavi S M,Taghdiri M,Samimi N,RahimiNasrabadi M.Eggshell bioactive membrane assisted synthesis of barium tungstate nanoparticles.Mater.Lett.,2014,121:5.
[52]Gedanken A.Using sonochemistry for the fabrication of nanomaterials.Ultrason.Sonochem.,2004,11:47.
[53]Bang J H,Suslick K S.Applications of ultrasound to the synthesis of nanostructured materials.Adv.Mater.,2010,22:1039.
[54]Hassan T A,Rangari V K,Rana R K,Jeelani S.Sonochemical effect on size reduction of Ca CO3 nanoparticles derived from waste eggshells.Ultrason.Sonochem.,2013,20:1308.
[55]Wang X K,Wei Y C,Wang J G,Guo W L,Wang C.The kinetics and mechanism of ultrasonic degradation of p-nitrophenol in aqueous solution with CCl4 enhancement.Ultrason.Sonochem.,2012,19:32.
[56]Nagargoje D,Mandhane P,Shingote S,Badadhe P,Gill C.Ultrasound assisted one pot synthesis of imidazole derivatives using diethyl bromophosphate as an oxidant.Ultrason.Sonochem.,2012,19:94.
[2]Pourmortazavi S M,Hajimirsadeghi S S,Rahimi-Nasrabadi M.Taguchi robust design to optimize synthesis of lead oxalate nano-disks.Mater.Sci.Semicond.Process.,2013,16:131.
[3]Rahimi-Nasarabadi M,Ahmadi F,Hamdi S,Eslami N,Didehban K,Ganjali Ganjali M R.Preparation of nanosized chromium carbonate and chromium oxide green pigment through direct carbonation and precursor thermal decomposition.J.Mol.Liq.,2016,216:814.
[4]Adib K,Rahimi-Nasrabadi M,Rezvani Z,Pourmortazavi S M,Ahmadi F,Naderi H R,Ganjali M R.Facile chemical synthesis of cobalt tungstates nanoparticles as high performance supercapacitor.J.Mater.Sci.Mater.Electron.,2016,27:4541.
[5]Sheldon R A.Fundamentals of green chemistry:efficiency in reaction design.Chem.Soc.Rev.,2012,41:1437.
[6]Anastas P,Eghbali N.Green chemistry:principles and practice.Chem.Soc.Rev.,2010,39:301.
[7]Cravotto G,Cintas P.Power ultrasound in organic synthesis:moving cavitational chemistry from academia to innovative and large-scale applications.Chem.Soc.Rev.,2006,35:180.
[8]Naghizadeh-Alamdari S,Habibi-Yangjeh A.Sonochemical preparation of Ag Br-Zn O nanocomposites in water using one-pot method as highly efficient photocatalyst under visible light.J.Iran.Chem.Soc.,2015,12:1961.
[9]Naghizadeh-Alamdari S,Habibi-Yangjeh A,Pirhashemi M.One-pot ultrasonic-assisted method for preparation of Ag/Ag Cl sensitized Zn O nanostructures as visible-light-driven photocatalysts.Solid State Sci.,2015,40:111.
[10]Shahidzadeh M,Shabihi P,Pourmortazavi S M.Sonochemical preparation of copper(II)chromite nanocatalysts and particle size optimization via taguchi method.J.Inorganic Organomet.Polym.Mater.,2015,25:986.
[11]Naderi H R,Ganjali M R,Dezfuli A S,Norouzi P.Sonochemical preparation of a ytterbium oxide/reduced graphene oxide nanocomposite for supercapacitors with enhanced capacitive performance.RSC Advances,2016,6:51211.
[12]Dezfuli A S,Ganjali M R,Norouzi P,Faridbod F.Facile sonochemical synthesis and electrochemical investigation of ceria/graphene nanocomposites.J.Mater.Chem.B,2015,3:2362.
[13]Li J T,Wang S X,Chen G F,Li T S.Some applications of ultrasound irradiation in organic synthesis.Curr.Org.Synth.,2005,2:415.
[14]Roushani M,Shamsipur M,Pourmortazavi S M.Amprometric detection of Glycine,L-Serine,and L-Alanine using glassy carbon electrode modified by Ni O nanoparticles.J.Appl.Electrochem.,2012,42:1005.
[15]Cella R,Stefani H A.Ultrasound in heterocycles chemistry.Tetrahedron,2009,65:2619.
[16]Mc Kee M L,Kerwin S M.Synthesis,metal ion binding,and biological evaluation of new anticancer2-(2′-hydroxyphenyl)benzoxazole analogs of UK-1.Bioorg.Med.Chem.,2008,16:1775.
[17]Siddiqui N,Rana A,Khan S A,Bhat M A,Haque S E.Synthesis of benzothiazolesemicarbazones as novel anticonvulsants-the role of hydrophobic domain.Bioorg.Med.Chem.Lett.,2007,17:4178.
[18]Huang S T,Hsei I J,Chen C.Synthesis and anticancer evaluation of bis(benzimidazoles),bis(benzoxazoles),and benzothiazoles.Bioorg.Med.Chem.,2006,14:6106.
[19]Teimouri A,Chermahini A N,Salavati H,Ghorbanian L.An efficient and one-pot synthesis of benzimidazoles,benzoxazoles,benzothiazoles and quinoxalines catalyzed via nano-solid acid catalysts.J.Mol.Catal.A:Chem.,2013,373:38.
[20]Inamdar S M,More V K,Mandal S K.Cu O nano-particles supported on silica,a new catalyst for facile synthesis of benzimidazoles,benzothiazoles andbenzoxazoles.Tetrahedron.Lett.,2013,54:579.
[21]Bala M,Verma P K,Sharma D,Kumar N,Singh B.Highly efficient water-mediated approach to access benzazoles:metal catalyst and base-free synthesis of2-substituted benzimidazoles,benzoxazoles,and benzothiazoles.Mol.Divers,2015,19:263.
[22]Shelkar R,Sarode S,Nagarkar J.Nano ceria catalyzed synthesis of substituted benzimidazole,benzothiazole,and benzoxazole in aqueous media.Tetrahedron Lett.,2013,54:6986.
[23]Girardet J L,Townsend L B.Synthesis ofβ-l-Lyxofuranosyl benzimidazoles by an unexpected intramolecular displacement reaction.J.Org.Chem.,1999,64:4169.
[24]Tumelty D,Cao K,Holmes C P.Traceless solid-phase synthesis of substituted benzimidazoles via a base-cleavable linker.Org.Lett.,2001,3:83.
[25]Raju B,Nguyen N,Holland G W.Solution-phase parallel synthesis of substituted benzimidazoles.J.Comb.Chem.,2002,4:320.
[26]Chen F,Shen C J,Yang D.A simple protocol for the synthesis of 2-arylbenzoxazoles by oxidation with o-iodoxybenzoic acid(IBX)and its application in the synthesis of arylbenzoxazole-containing amino acids.Tetrahedron Lett.,2011,52:2128.
[27]Leng W N,Zhou Y M,Xu Q H,Liu J Z.Synthesis and characterization of nonlinear optical side-chain polyimides containing the benzothiazole chromophores.Macromolecules,2001,34:4774.
[28]Hutchinson I,Jennings S A,Vishnuvajjala B R,Westwell A D,Stevens M F G.Antitumor benzothiazoles.16.1Synthesis and pharmaceutical properties of antitumor2-(4-aminophenyl)benzothiazole amino acid prodrugs.J.Med.Chem.,2002,45:744.
[29]Xu H X,Zeigera Brad W,Suslick Kenneth S.Sonochemical synthesis of nanomaterials.Chem.Soc.Rev.,2013,42:2555.
[30]Rahimi-Nasrabadi M,Rostami M,Ahmadi F,Fallah Shojaie A,Delavar Rafiee M.Synthesis and characterization of Zn Fe2-xYbxO4-graphene nanocomposites by sol-gel method.J.Mater.Sci.Mater.Electron.,2016,27:11940.
[31]Rahimi-Nasrabadi M,Behpour M,Sobhani-Nasab A,Rangraz Jeddy M.Nanocrystalline Ce-doped copper ferrite:synthesis,characterization,and its photocatalyst application.J.Mater.Sci.Mater.Electron,2016,27:11691.
[32]Gholinejad M,Karimi B,Mansouri F.Synthesis and characterization of magnetic copper ferrite nanoparticles and their catalytic performance in one-pot odorless carbon-sulfur bond formation reactions.J.Mol.Catal.A:Chem.,2014,386:20.
[33]Maleki B,Eshghi H,Khojastehnezhad A,Tayebee R,Ashrafi S S,Kahoo G E,Moeinpour F.Silica coated magnetic Ni Fe2O4 nanoparticle supported phosphomolybdic acid;synthesis,preparation and its application as a heterogeneous and recyclable catalyst for the one-pot synthesis of tri-and tetra-substituted imidazoles under solvent free conditions.RSC Adv.,2015,5:64850.
[34]Liu W J,Ke Tiana,Jiang H.One-pot synthesis of NiNi Fe2O4/carbon nanofiber composites from biomass for selective hydrogenation of aromatic nitro compounds.Green Chem.,2015,17:821.
[35]Gong M,Dai H.A mini review of Ni Fe-based materials as highly active oxygen evolution reaction electrocatalysts.Nano Res.,2015,8:23.
[36]Rahimi-Nasrabadi M,Pourmortazavi S M,Aghazadeh M,Ganjali M R,Sadeghpour K M,Novrouzi P.Samarium carbonate and samarium oxide:synthesis,characterization and eluation of the photo-catalytic behavior.J.Mater.Sci.Mater.Electron.,2017,28:5574.
[37]Roesky P W.Molecular Catalysis of Rare-Earth Elements.Vol.137.Berlin:Springer Science&Business Media,2010.
[38]Ji B F,Tian C A,Zhang Q Z,Ji D D,Yang J,Xie J S,Si JY.Magnetic properties of samarium and gadolinium codoping Mn-Zn ferrites obtained by sol-gel auto-combustion method.J.Rare Earths,2016,34:1017.
[39]Wang W H,Li W,Guo R T,Chen Q L,Wang Q S,Pan WG,Hy G X.A Ce Fe Ox catalyst for catalytic oxidation of NO to NO2.J.Rare Earths,2016,34:876.
[40]Liu S,Wu X D,Weng D,Ran R.Ceria-based catalysts for soot oxidation:a review.J.Rare Earths,2015,33:567.
[41]Pourmortazavi S M,Rahimi-Nasrabadi M,Fazli Y,Mohammad-Zadeh M.Taguchi method assisted optimization of electrochemical synthesis and structural characterization of copper tungstate nanoparticles.Int.J.Refract.Met.Hard Mater.,2015,51:29.
[42]Rahimi-Nasrabadi M,Behpour M,Sobhani-Nasab A,Hosseinpour-Mashkani S M.Zn Fe2-xLaxO4 nanostructure:synthesis,characterization,and its magnetic properties.J.Mater.Sci.Mater.Electron.,2015,26:9776.
[43]Pourmortazavi S M,Zaree A,Mirsadeghi S.Taguchi approach-assisted optimization of spraying in non-solvent process for preparation of potassium perchlorate nanoparticles.J.Sol-Gel Sci.Technol.,2015,76:510.
[44]Rahimi-Nasrabadi M,Pourmortazavi M,Davoudi-Dehaghani A A,Hajimirsadeghi S S,Zahedi M M.Synthesis and characterization of copper oxadate and copper oxide nanoparticles by statistically optimized controlled precipitation and calcination.Cryst.Eng.Comm.,2013,15:4077.
[45]Shamsipur M,Pourmortazavi S M,Roushani M,Kohsari I,Hajimirsadeghi S S.Novel approach for electrochemical preparation of sulfur nanoparticles.Microchim.Acta,2011,173:445.
[46]Rahimi-Nasrabadi M,Pourmortazavi S M,KhalilianShalamzari M,Hajimirsadeghi S S,Zahedi M M.Optimization of synthesis procedure and structure characterization of manganese tungstate nanoplates.Open Chem.,2013,11:1393.
[47]Rahimi-Nasrabadi M,Pourmortazavi S M,KhalilianShalamzari M.Facile chemical synthesis and structure characterization of copper molybdate nanoparticles.J.Mol.Struct.,2015,1083:229.
[48]Pourmortazavi S M,Taghdiri M,Makari V,Rahimi-Nasrabadi M.Procedure optimization for green synthesis of silver nanoparticles by aqueous extract of Eucalyptus oleosa.Spectrochim.Acta A:Mol.Biomol.Spectrosc.,2015,136:1249.
[49]Pourmortazavi S M,Rahimi-Nasrabadi M,Hajimirsadeghi S S.Applying the taguchi robust design to optimization of the experimental conditions for synthesis of lead chromate nanorods.J.Dispersion Sci.Technol.,2012,33:254.
[50]Pourmortazavi S M,Rahimi-Nasrabadi M,KhalilianShalamzari M,Ghaeni H R,Hajimirsadeghi S S.Facile chemical synthesis and characterization of copper tungstate nanoparticles,J.Inorganic Organomet.Polym.Mater.,2014,24:333.
[51]Pourmortazavi S M,Taghdiri M,Samimi N,RahimiNasrabadi M.Eggshell bioactive membrane assisted synthesis of barium tungstate nanoparticles.Mater.Lett.,2014,121:5.
[52]Gedanken A.Using sonochemistry for the fabrication of nanomaterials.Ultrason.Sonochem.,2004,11:47.
[53]Bang J H,Suslick K S.Applications of ultrasound to the synthesis of nanostructured materials.Adv.Mater.,2010,22:1039.
[54]Hassan T A,Rangari V K,Rana R K,Jeelani S.Sonochemical effect on size reduction of Ca CO3 nanoparticles derived from waste eggshells.Ultrason.Sonochem.,2013,20:1308.
[55]Wang X K,Wei Y C,Wang J G,Guo W L,Wang C.The kinetics and mechanism of ultrasonic degradation of p-nitrophenol in aqueous solution with CCl4 enhancement.Ultrason.Sonochem.,2012,19:32.
[56]Nagargoje D,Mandhane P,Shingote S,Badadhe P,Gill C.Ultrasound assisted one pot synthesis of imidazole derivatives using diethyl bromophosphate as an oxidant.Ultrason.Sonochem.,2012,19:94.