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Nardelli",slug:"pedro-h.j.-nardelli"}]},{id:"12896",title:"Design and Analysis of a Multi-Level Location Information Based Routing Scheme for Mobile Ad Hoc Networks",slug:"design-and-analysis-of-a-multi-level-location-information-based-routing-scheme-for-mobile-ad-hoc-net",signatures:"Koushik Majumder, Sudhabindu Ray and Subir Kumar Sarkar",authors:[{id:"13742",title:"Dr.",name:"Koushik",middleName:null,surname:"Majumder",fullName:"Koushik Majumder",slug:"koushik-majumder"},{id:"13832",title:"Prof.",name:"Subir",middleName:null,surname:"Kumar Sarkar",fullName:"Subir Kumar Sarkar",slug:"subir-kumar-sarkar"},{id:"23706",title:"Dr.",name:"Sudhabindu",middleName:null,surname:"Ray",fullName:"Sudhabindu Ray",slug:"sudhabindu-ray"}]},{id:"12897",title:"Power Control in Ad Hoc Networks",slug:"power-control-in-ad-hoc-networks",signatures:"Muhammad Mazhar Abbas and Hasan Mahmood",authors:[{id:"13775",title:"Dr.",name:"Hasan",middleName:null,surname:"Mahmood",fullName:"Hasan Mahmood",slug:"hasan-mahmood"},{id:"14396",title:"Mr.",name:"Muhammad Mazhar",middleName:null,surname:"Abbas",fullName:"Muhammad Mazhar Abbas",slug:"muhammad-mazhar-abbas"}]}]}],publishedBooks:[{type:"book",id:"8086",title:"Wireless Sensor Networks",subtitle:"Design, Deployment and Applications",isOpenForSubmission:!1,hash:"1dd4efd7e9d6964d97acdfb61c669f14",slug:"wireless-sensor-networks-design-deployment-and-applications",bookSignature:"Siva S. 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Sierra",coverURL:"https://cdn.intechopen.com/books/images_new/913.jpg",editedByType:"Edited by",editors:[{id:"72042",title:"Dr.",name:"Roberto",surname:"Hincapie",slug:"roberto-hincapie",fullName:"Roberto Hincapie"}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"3341",title:"Sustainable Radio Frequency Identification Solutions",subtitle:null,isOpenForSubmission:!1,hash:"2adaeecfea5c7ebc03b4bb7764c3bdd3",slug:"sustainable-radio-frequency-identification-solutions",bookSignature:"Cristina Turcu",coverURL:"https://cdn.intechopen.com/books/images_new/3341.jpg",editedByType:"Edited by",editors:[{id:"9302",title:"Dr.",name:"Cristina",surname:"Turcu",slug:"cristina-turcu",fullName:"Cristina Turcu"}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"3406",title:"Selected Topics in WiMAX",subtitle:null,isOpenForSubmission:!1,hash:"a50705a81f7e17efa43d2639d47e3b15",slug:"selected-topics-in-wimax",bookSignature:"Gianni Pasolini",coverURL:"https://cdn.intechopen.com/books/images_new/3406.jpg",editedByType:"Edited by",editors:[{id:"79639",title:"Dr.",name:"Gianni",surname:"Pasolini",slug:"gianni-pasolini",fullName:"Gianni Pasolini"}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}},{type:"book",id:"5914",title:"Optical Fiber and Wireless Communications",subtitle:null,isOpenForSubmission:!1,hash:"d85edb2cf7e2780dc8f029a0f4021520",slug:"optical-fiber-and-wireless-communications",bookSignature:"Rastislav Roka",coverURL:"https://cdn.intechopen.com/books/images_new/5914.jpg",editedByType:"Edited by",editors:[{id:"112777",title:"Dr.",name:"Rastislav",surname:"Róka",slug:"rastislav-roka",fullName:"Rastislav Róka"}],equalEditorOne:null,equalEditorTwo:null,equalEditorThree:null,productType:{id:"1",chapterContentType:"chapter",authoredCaption:"Edited by"}}],publishedBooksByAuthor:[]},onlineFirst:{chapter:{type:"chapter",id:"65953",title:"Eco-Friendly and Facile Synthesis of Substituted Imidazoles via Nano Zirconia Catalyzed One-Pot Multicomponent Reaction of Isatin Derivatives with Ammonium Acetate and Substituted Aromatic Aldehydes under Solvent Free Conditions",doi:"10.5772/intechopen.82720",slug:"eco-friendly-and-facile-synthesis-of-substituted-imidazoles-via-nano-zirconia-catalyzed-one-pot-mult",body:'\nImidazole is a “1, 3-diazole” and is classified as an alkaloid. Imidazole (1) refers to the parent compound, whereas imidazoles are a class of heterocycles with similar ring structure, but varying substituents. This ring system is present in important biological building blocks, such as histidine (2), and the related hormone histamine (3). Imidazole can serve as a base and as a weak acid. Many drugs contain an imidazole ring, such as antifungal drugs and Nitroimidazole (4) [1, 2, 3, 4, 5].
Imidazole derivatives are mostly used as organic resources [6, 7] and it also plays important roles in various types of biological activities [8, 9]. This multitalented applicability of Imidazole draws attention towards the importance of access to efficient synthetic routes to well-designed and highly substituted imidazole derivatives.
\nDue to their impressive significance, various synthetic routes have been designed. Substituted imidazoles are generally prepared by microwave irradiated one pot three-component cyclocondensation of a 1, 2-diketone, α-hydroxy ketone or α-ketomonoxime with an aldehyde and ammonium acetate [10, 11, 12, 13], ionic liquids [14, 15], refluxing in acetic acid [16], silica sulfuric acid [17, 18], Yb(OTf)3 [19], Yb(OPf)3 [20], iodine [21], Zr(acac)4 [22], InCl3·3H2O [23], heteropolyacid [24], sodium bisulfate [25], potassium aluminum sulfate (alum) [26], ceric ammonium nitrate (CAN) [27], (NH4)6 Mo7O24·4H2O [28], zeolite HY/silica gel [29], ZrCl4 [30], polymer-supported ZnCl2 [31] and L-proline [32]. Moreover, they have also been prepared by the addition of substituted amino alcohol to a thioamide and subsequent oxidation with PDC or by the reaction of aryl nitriles and α,α-dilithioarylnitromethanes or by multistep syntheses.
Due to their potential utility, majority of these synthetic routes experience one or more severe disadvantages, such as difficult and intricate work-up and purification, huge amounts of waste materials, strongly acidic conditions, occurrence of side reactions, low yields, high temperature, long reaction time and the use of expensive reagents. Hence, there is a great demand of a highly efficient protocol with mild reaction conditions to synthesize substituted imidazoles.
\nIn recent times, metal nanoparticles are used as heterogeneous catalysts in organic synthesis mainly because they achieve the objectives of green and sustainable chemistry. Recently Scientists have done a lot of work to synthesize precise metal nanoparticles. The new path is the coherent design and synthesis of very active and selective nanocatalysts by controlling the structure and composition of the active nanoparticles among all of them. The easiness of separation, recovery, and reuse of these NPs further enhance their attractiveness as green and sustainable catalysts [3, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45].
\nRecently, nano zirconia (ZrO2) has attracted considerable attention due to their wide applicability as a heterogeneous catalyst [46, 47, 48, 49, 50, 51]. The catalytic activities and selectivities of nano zirconia are highly affected by their crystal phase (monoclinic and tetragonal) [52, 53, 54]. ZrO2 nanoparticle catalyst is a cheap, moisture stable, safe, reusable, and commercially available white powder is of big curiosity to many researchers. It has been revealed from the literature that numerous parallel applications of nano zirconia, as an effective catalyst in green/sustainable synthetic chemistry, have already been reported [55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67].
\nIn view of the above and as a part of our research group to synthesize the biologically active compounds [68, 69, 70, 71, 72], it was thought worthwhile to synthesize some novel imidazoles fused with indole nucleus of biocidal interest because the combination of two or more different heterocyclic compounds in a single molecule frequently increases the biocidal profile amazingly. With the aim of getting targeted products, i.e., substituted imidazole a greener “NOSE” (nanoparticles-catalyzed organic synthesis enhancement) approach has been designed under solvent-free conditions.
\nImidazole derivatives
Nano ZrO2 catalyzed synthesis of imidazole derivatives.
To optimize the reaction conditions, several parameters were tested. The catalytic efficiency of the ZrO2 NPs was highly influenced by their amount (mol%). Therefore, a model reaction of isatin with ammonium acetate and benzaldehyde using different amounts of ZrO2 NPs was carried out (Table 1). It has been observed that there is a notable impact of the catalyst on the yield of product and in the absence of catalyst only poor yield was obtained after 120 min (Entry 1, Table 1). It was found that product yield is increased with increasing catalyst concentration. Only 5 mol% of catalyst was required to provide 60% yield in 60 min (Entry 2, Table 1). The best yield of 88% was obtained with 15 mol% of ZrO2 NPs (Entry 5, Table 1). However, the reaction rate and product yield were not improved by further increase of catalyst concentration (>15 mol%) (Entry 6, Table 1).
\nEntry | \nZrO2 mol% | \nTime (min.) | \n%Yield | \n
---|---|---|---|
1 | \n0 | \n120 | \n23 | \n
2 | \n5 | \n60 | \n60 | \n
3 | \n10 | \n45 | \n75 | \n
4 | \n12 | \n35 | \n82 | \n
6 | \n20 | \n30 | \n88 | \n
Effect of catalyst amount (mol%) on yield of the product
Note: Bold values represent optimized reaction condition.
To optimize the molar proportion of the reactant, the model reaction was carried out using different molar proportions of reactants (Table 2). A scrutiny of the table clearly shows that the best result was obtained using isatin, ammonium acetate, benzaldehyde in the molar proportion 1.0:5.0:1.0 at 110°C under solvent free conditions (Entry 5, Table 2).
\nEntry | \nMolar ratio of reactants | \n%Yield | \n
---|---|---|
\n | Isatin:ammoniumacetate:benzaldehyde | \n\n |
1 | \n1.0:1.0:1.0 | \nTrace amount | \n
2 | \n1.0:2.0:1.0 | \n35 | \n
3 | \n1.0:3.0:1.0 | \n52 | \n
4 | \n1.0:4.0:1.0 | \n78 | \n
6 | \n1.0:6.0:1.0 | \n87 | \n
7 | \n1.0:5.0:1.2 | \n87 | \n
8 | \n1.2:5.0:1.0 | \n86 | \n
Effect of molar ratio of substrates on the yield of the product
Note: Bold values represent optimized reaction condition.
To see the effect of temperature, the model reaction was examined under different temperatures. Obviously, reaction rate and product yield both were increased with enhancing temperature from 50 to 110°C. This study shows that the 110°C was favorable temperature for the multicomponent reaction of isatin with ammonium acetate and benzaldehyde (Table 3).
\nEntry | \nTemp. °C | \nTime | \n% Yield | \n
---|---|---|---|
1 | \nrt | \n- | \nNo reaction | \n
2 | \n50 | \n10 h | \nTrace amount | \n
3 | \n60 | \n6 h | \n65 | \n
4 | \n70 | \n4 h | \n70 | \n
5 | \n80 | \n1.5 h | \n78 | \n
6 | \n90 | \n55 min | \n84 | \n
7 | \n100 | \n45 min | \n86 | \n
9 | \n120 | \n30 min | \n88 | \n
Effect of temperature on the yield of the product
Note: Bold values represent optimized reaction condition.
Screening of solvent showed that solvent had a remarkable impact on the yield of product. It was observed that polar solvent provided better yield than nonpolar solvent, but excellent yield was obtained without solvent in smaller time. This may be due to the competitive adsorption of the solvent with the substrate molecule on the catalyst surface; hence reaction under solvent-free conditions gives excellent yield in short reaction time (Entry 5, Table 4). Another reason is that the eutectic mixture having uniform distribution of the reactants brings the reacting species in close proximity to react in solvent free condition than in the presence of solvent (Entry 1–4, Table 4).
\nEntry | \nSolvents | \nTime | \n%Yield | \n
---|---|---|---|
1 | \nEthanol | \n10 h | \n68 | \n
2 | \nAcetonitrile | \n10 h | \n59 | \n
3 | \nXylene | \n13 h | \n55 | \n
4 | \nTolune | \n18 h | \n52 | \n
Effect of solvents on the yield of the product
Note: Bold values represent optimized reaction condition.
Under the optimized set of reaction conditions, the effect of type of ZrO2 (nano or bulk) was also examined using model reaction(Table 5). This important parameter was studied by using four concentrations 5, 10, 12 and 15 mol% of ZrO2. These data proved that particle size and surface area would be an important factor for the catalytic efficiency of the ZrO2 NPs.
\nType of ZrO2 | \nMol% | \n% Yield | \n
---|---|---|
ZrO2 (Bulk) | \n5 | \n42 | \n
Surface area: 6.95m2/g | \n10 | \n51 | \n
Average particle size: 2 μm | \n12 | \n56 | \n
\n | 15 | \n66 | \n
ZrO2 (Nano) | \n5 | \n59 | \n
Surface area: 44.70 m2/g | \n10 | \n72 | \n
Average particle size: 20 nm | \n12 | \n84 | \n
\n | 15 | \n88 | \n
Effect of type of ZrO2 (bulk & nano) on the yield of the product
Reaction condition: Isatin, ammonium acetate & benzaldehyde (1.0, 5.0, 1.0) were stirred at 110°C to produce solid product.
The efficiency of the catalytic activity of the ZrO2 NPs with several other catalysts was compared and is summarized in Table 6. The result indicates that ZrO2 NPs was the best catalyst in terms of mol%, reaction time and percentage yield (Table 6).
\nType of catalyst | \nMol% | \nTime (min.) | \n% Yield | \n
---|---|---|---|
Bentonite clay | \n20 | \n60 | \n55 | \n
K-10 clay | \n20 | \n60 | \n58 | \n
PTSA | \n40 | \n75 | \n45 | \n
NH4Cl | \n30 | \n75 | \n44 | \n
EDTA | \n40 | \n75 | \n40 | \n
Iodine | \n30 | \n60 | \n53 | \n
Yb(OTf)3 | \n25 | \n60 | \n51 | \n
TiO2 (Nano) | \n20 | \n30 | \n80 | \n
Effect of different catalysts on the yield of the product
Note: Bold values represent optimized reaction condition.
Under the optimized reaction condition, the scope of this methodology was extended to the reaction of different isatin with a wide range of aromatic aldehydes. The findings reveal that the proposed methodology is equally applicable for the presence of both electron donating as well as electron withdrawing groups at the 5-position of isatin moiety (Table 7).
\nSynthesis of substituted imidazoles (4a–s).
The model reaction was carried out to examine the reusability of the catalyst, After each reaction, catalyst was recovered by filtration, washed, air-dried and reused directly for the next time up to run no. 10.The results showed that there is no obvious loss in product yield in subsequent reuse which proves the reusability and recyclability of ZrO2 NPs (Table 8).
\nEntry | \nNumber of cycle | \n%Yield | \n
---|---|---|
1 | \n- | \n88 | \n
2 | \n1 | \n88b | \n
3 | \n2 | \n87b | \n
4 | \n3 | \n86b | \n
5 | \n4 | \n83b | \n
6 | \n5 | \n80b | \n
7 | \n6 | \n80b,c | \n
8 | \n7 | \n80b | \n
9 | \n8 | \n78b | \n
10 | \n9 | \n75b | \n
11 | \n10 | \n76b,c | \n
Reusability and recyclability of ZrO2 NPs catalysta.
Reaction condition: Isatin, ammonium acetate, benzaldehydes (1.0:5.0:1.0) and ZrO2 NPs (15 mol%) were stirred at 110°C to produce solid product.
The catalyst was washed and dried at 80–90°C for 12 h.
ZrO2 NPs were calcinated at 600°C for 3 h.
The following mechanism was proposed for the formation of substituted imidazoles catalyzed by the ZrO2 NPs is given in Scheme 2. The reaction proceeds via the diamine intermediate [X]. Condensation of diamine with isatin derivatives followed by dehydration, and then rearrangement through the imino intermediate [Y] yielded the desired product.
\nProposed mechanism for the formation of substituted imidazoles 4a–s.
ZrO2 NPs were prepared and characterized by FTIR, XRD, SEM and TEM analysis. The BET surface area analyzer was used to calculate the specific surface area of synthesized ZrO2 NPs.
\nThe molecular nature of the synthesized material was identified by the FT-IR spectrum of the ZrO2 sample. The FT-IR spectrum of ZrO2 NPs depends on the nature of the material, preparative procedures used, solid-state structure, and so forth. In FT-IR, a strong absorption peak at about 500 cm−1 region is due to the Zr–O vibration, which confirm the formation of ZrO2 structure while the peak at 751 cm−1 is due to stretching vibrations of Zr–O–Zr, prominent peak at 1340 cm−1 represents O–H bonding, peak at 1622 cm−1 perhaps owing to the adsorbed moisture and peaks at about 2855–2922 cm−1 region is due to stretching of O–H groups.
\nThe broad peaks with high intensity in XRD pattern of ZrO2 NPs indicates that the sample was highly crystalline. The peaks observed at 2θ = 24.2 (011), 28.2 (−111), 31.4 (111), 35.0 (020), 40.5 (−112), 45.0 (211), and 55.4 (−311) are characteristics peaks of monoclinic zirconia (JCPDS card no. 37–1484) while diffraction peak observed at 2θ = 30.3 (101), 50.3 (212) and 60.2 (211) are due to tetragonal zirconia (JCPDS card no. 79-1769). The broadening of peaks shows the smaller particle size of ZrO2 NPs
XRD spectra of ZrO2 NPs.
Morphological studies were done with the help of SEM and TEM analysis of 600°C calcinated ZrO2 NPs sample that are shown in Figures 2 and 3, respectively. SEM analysis shows that NPs are non-homogenous and agglomerated and it also indicates the spherical nature and nano size (nm regime) of the ZrO2 nanoparticles but size could be finely decided from TEM. For the purpose, TEM of sample has been shown in Figure 3.
\nSEM image of ZrO2 NPs.
TEM image of ZrO2 NPs.
As it is clear from TEM micrograph of sample, some agglomeration of the NPs, has been seen due to presence of different m- and t-phases in the sample. It was also observed that the sizes of the particles are of the order 20 nm along with agglomeration.
\nBET surface area analyzer was used to calculate the surface area of synthesized ZrO2 NPs by nitrogen absorption which was found to be 44. 70 m2/g.
\n0.075 M solution of ZrOCl2.8H2O was prepared and then precipitated with NH4OH (25%) with continuous stirring on a magnetic stirrer till the PH raises in the range of 10–10.5.This resulted in the formation of precipitate of zirconium hydroxide. The precipitate was filtered and washed with double distilled water until traces of chloride ion were completely removed from the filtrate. Complete removal of chloride ion from filtrate was checked by titrating it with AgNO3 solution using potassium chromate as indicator. Now, the precipitate was dried in oven at 80–90°C for 24 h and calcinated at 600°C for 3 h in order to formation of white nano zirconia powder.
\nTo a mixture of isatin derivatives
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownsolid,
Brownish whitesolid,
ZrO2 nanoparticles have been synthesized and a novel synthetic route has been developed for the multicomponent reaction of isatin derivatives with ammonium acetate and substituted aromatic aldehydes using ZrO2 nanoparticles under solvent-free conditions. The yields of the products obtained were up to 93% at 110°C. The advantage of the proposed method is its facile reaction conditions; the product can be isolated very easily without the use of column chromatography and the catalyst can be recycled. The simplicity of the presented protocol makes it an interesting alternative to other approaches. The obtained catalyst is expected to contribute to the development of environmentally benign methods and forms a part of nanomaterial chemistry.
\nNMR spectra of compound
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His studies in robotics lead him not only to a PhD degree but also inspired him to co-found and build the International Journal of Advanced Robotic Systems - world's first Open Access journal in the field of robotics.",institutionString:null,institution:{name:"TU Wien",country:{name:"Austria"}}},{id:"441",title:"Ph.D.",name:"Jaekyu",middleName:null,surname:"Park",slug:"jaekyu-park",fullName:"Jaekyu Park",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/441/images/1881_n.jpg",biography:null,institutionString:null,institution:{name:"LG Corporation (South Korea)",country:{name:"Korea, South"}}},{id:"465",title:"Dr.",name:"Christian",middleName:null,surname:"Martens",slug:"christian-martens",fullName:"Christian Martens",position:null,profilePictureURL:"//cdnintech.com/web/frontend/www/assets/author.svg",biography:null,institutionString:null,institution:{name:"Rheinmetall (Germany)",country:{name:"Germany"}}},{id:"479",title:"Dr.",name:"Valentina",middleName:null,surname:"Colla",slug:"valentina-colla",fullName:"Valentina Colla",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/479/images/358_n.jpg",biography:null,institutionString:null,institution:{name:"Sant'Anna School of Advanced Studies",country:{name:"Italy"}}},{id:"494",title:"PhD",name:"Loris",middleName:null,surname:"Nanni",slug:"loris-nanni",fullName:"Loris Nanni",position:null,profilePictureURL:"https://mts.intechopen.com/storage/users/494/images/system/494.jpg",biography:"Loris Nanni received his Master Degree cum laude on June-2002 from the University of Bologna, and the April 26th 2006 he received his Ph.D. in Computer Engineering at DEIS, University of Bologna. 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From 1985 to 1986, he was a Research Fellow in the Research Institute for Electronic Equipment, ZZU AD, Plovdiv, Bulgaria. In 1986, he joined the Department of Control Systems, Technical University of Sofia at the Plovdiv campus, where he is presently a Full Professor. He has held long-term visiting Professor/Scholar positions at various institutions in South Korea, Turkey, Mexico, Greece, Belgium, UK, and Germany. And he has coauthored one book and authored or coauthored more than 80 research papers in conference proceedings and journals. 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After finishing his P. hD degree in 1992, he served in the Industry as a Scientific Officer and continued his academic career as a visiting scholar for a number of educational institutions. In 1996 he joined National University of Science & Technology Pakistan (NUST) as an Associate Professor; NUST is one of the top few universities in Pakistan. In 1999 he joined an International Company Lineo Inc, Canada as Manager Compiler Group, where he headed the group for developing Compiler Tool Chain and Porting of Operating Systems for the BLACKfin processor. The processor development was a joint venture by Intel and Analog Devices. In 2002 Lineo Inc., was taken over by another company, so he joined Aalborg University Denmark as an Assistant Professor.\nProfessor Akbar has truly a multi-disciplined career and he continued his legacy and making progress in many areas of his interests both in teaching and research. 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The cubic equations of state (CEOS) such as Van der Waals, Redlich-Kwong, Soave, and Peng-Robinson are simple models that have been widely used in the oil industry. This chapter expressed literature for EOS that varies from simple expressions to multiple constant and convoluted types of equations. Many attempts have been made to describe the thermodynamic behavior of fluids to predict their physical properties at given conditions. So, several forms of the equation of state have been presented to the oil industry in order to calculate reservoir fluid properties. The heat exchanger is important in wildly fields as in aerospace, petrochemical industry, refrigeration, and other fields. 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