Experimentally Designed of PVC/NiAl2O3/AlF3 Nanocomposite by Sol-Gel Method
Subject Areas : composite materialsElinaz Ahmadian 1 , Maryam Kargar Razi 2 , Babak Sadeghi 3 , Mahbobeh Nakhaei 4
1 - Department of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, IRAN
2 - Department of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran
3 - Department of Chemistry, Islamic Azad University, Tonekabon Branch, Tonekabon, Iran
4 - Department of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, IRAN
Keywords: Nano Catalytic activity, Nano-Size, Morphology, Sol-gel, TEM,
Abstract :
In this study, we have synthesized nano Aluminum Fluoride (nAF) nanoparticles by the sol-gel method and studied the nano-sized morphology of crystals. In the other section, the PVC/NiAl2O3/AlF3 (nPNA) nanocomposite was successfully prepared and characterized by FT-IR, and HRTEM techniques. FTIR peaks of the PVC and nPNA have been shown spherical shape of PVC and also spherical shapes nanoparticles of nPNA loaded on PVC. A solvothermal method has been successfully introduced and applied for catalyst efficiency. This nanocomposite was used for the removal of Congo red dye. For this purpose, the morphology and the structure of crystals have been changed by modification on precursor gel. Meanwhile, precursor gel preparation and the interaction on the nano-sized area have been studied. This study exhibited that PVC/NiAl2O3/AlF3 (nPNA) nanocomposite is an effective catalyst for the synthesis of some organic derivatives. The results show that the as-prepared nanocomposite is an efficient catalyst and that PVC/NiAl2O4/AlF3 nanocomposite can be used in the next-generation of some organic reactions and faster production of various materials.
[1] Turner, M. E., Trentler, T. J., and Colvin, V. L., Thin Films of Macroporous Metal Oxides, Adv. Mater., Vol. 13, 2001, pp. 180-183.
[2] Aguado, J., Serrano, D. P., Escola, J. M., Garagorri, E., and Fernandez, J. A., Catalytic Cracking of a Polyolefin Mixture Over Different Acid Solid Catalysts, Polym. Degrad. Stabil., Vol. 69, 2000, pp. 11-16.
[3] Gronchi, P., Kaddouri, A., Centola, P., and Del Rosso, R., Synthesis of Nickel Supported Catalysts for Hydrogen Production by Sol-Gel Method, J. Sol-Gel Sci. Tech., Vol. 26, 2003, pp. 843-846.
[4] L. Khelifi, L., Ghorbel, A., Effect of Preparation Conditions on the Stability of Pt/Al2O3 Catalysts in Methane Combustion, J. Sol-Gel Sci Tech., Vol. 19, 2000, pp. 643-646.
[5] Meixner, H., Lampe, U., Gerblinger, J., and Fleische, M., Chemosensors for Motor Management Systems of The Future, Fresenius J. Anal. Chem., Vol. 348, 1994, pp. 536-541.
[6] Bennett, R. A., McCavish, N. D., Non-Stoichiometric Oxide Surfaces and Ultra-Thin Films: Characterisation of TiO2, Topics in Catalysis. Vol. 36, 2005, pp. 11-19.
[7] Chemistry of Advanced Materials: An Overview, Wiely-VCH, Inc, Canada, 1998, Chapt. 9, Molecular Precursor Routes to Inorganic Solids, pp. 389–448.
[8] Righini, G. C., Pelli, S., Nonlinear Properties of Semiconductor-Doped Silica Solgel Films, J. Sol-Gel Sci. Tech., Vol. 8, 1997, pp. 991–997.
[9] Maryani, E., Abdullah, M., Dayamanti, H., and Septawendar, R., Effect of Ultrasonic Irradiation on The Characteristic of γ-Al2O3 Nanorods Synthesized from Nitrate Salt-Starch Precursors Trough a Facile Precipitation Method, J. Ceram. Soc. Japan., Vol. 124, 2016, pp. 1205-1210.
[10] Amirsalari, Farjami, S., Effect of pH and Calcinations Temperature on Structural and Optical Properties of Alumina Nanoparticles, J. Superlatt. Microstruct. Vol. 82, 2015, pp. 507-524.
[11] Da-Ros, S., Barbosa-Coutinho, E., Schwaab, M., Calsavara, V., and Fernandes-Machado, N. R. C., Modeling the Effects of Calcination Conditions on The Physical and Chemical Properties of Transition Alumina Catalysts, J. Mater. Character., Vol. 80, 2013, pp. 50-61.
[12] Tayseir Mohammed, E., Saikat, M., Some Studies on The Surface Modification of Sol-Gel Derived Hydrophilic Silica Nanoparticles, Int. J. Nano Dimens., Vol. 8, 2017, pp. 97-106.
[13] Maity, S. K., Ancheyta, J., and Rana, M. S., Support Effects on Hydroprocessing of Maya Heavy Crude, J. Energy and Fuel., Vol. 19, 2005, pp. 343-347.
[14] Fernandez., V. C., Ramrez, J., Alejandre, A. G., Sanchez-Minero, F., Cuevas-Garcıa, R., and Torres-Mancera, P., Synthesis, Characterization and Evaluation of NiMo/SiO2–Al2O3 Catalysts Prepared by the pH-Swing Method, J. Catal. Today., Vol. 130, 2008, pp. 337–344.
[15] Dao Quan, H., Yang, H., Tamura, M., and Sekiya., A., SbF5/PAF—a Novel Fluorinating Reagent in Preparing Fluorine Compounds, J. Fluorine Chem., Vol. 125, 2004, pp. 1169-1172.
[16] Sekiya, dao Quan, H., Tamura, M., Gao, R. X., and Murata, J., Sol-Gel Synthesis and Catalytic Properties of PVC/NiAl2O3/AlF3 Nanocomposite", J. Fluorine Chem., Vol. 112, 2001, pp. 145-148.
[17] Dao Quan, H., Tamura, M., Takagi, T., and Sekiya, A., Fluorination of N-Dodecane Adsorbed on Porous Aluminium Fluoride by Gaseous Fluorine, J. Fluorine Chem., Vol. 99, 1999, pp. 167-170.
[18] Krespan, C. G., Dixon, D. A., Fluoroolefin Condensation Catalyzed by Aluminum Chlorofluoride, J. Fluorine Chem., Vol. 77, 1996, pp. 117-126.
[19] Sadjadi, M. A. S., Sadeghi, B., Meskinfam, M., Zare, K., and Azizian, J., Synthesis and Characterization of Ag/PVA Nanorods By Chemical Reduction Method, Physica E: Low-Dimensional Systems and Nanostructures, Vol. 40, 2008, pp. 3183-3186.
[20] Sadeghi, B., Sadjadi, M. A. S., and Vahdati, R. A. R., Nanoplates Controlled Synthesis and Catalytic Activities of Silver Nanocrystals, Superlattices and Microstructures, Vol. 46, 2009, pp. 858-863.
[21] Sadeghi, B., Jamali, M., Kia, Sh., Amini Nia, A., and Ghafari., S., Synthesis and Characterization of Silver Nanoparticles for Antibacterial Activity, Int. J. Nano Dimens., Vol. 1, 2010, pp. 119-124.
[22] Sadeghi, B., Garmaroudi, F. S., Hashemi, M., Nezhad, H. R., Nasrollahi, A., Ardalan, S., and Ardalan, S., Comparison of the Anti-Bacterial Activity on The Nanosilver Shapes: Nanoparticles, Nanorods and Nanoplates, Adv. Powder Technol., Vol. 23, 2012, pp. 22-26.
[23] Sadeghi, B., Pourahmad, A., Synthesis of Silver/Poly (Diallyl Dimethyl Ammonium Chloride) Hybride Nanocomposite, Adv. Powder Tech., Vol. 22, 2012, pp. 669-673.
[24] Sadeghi, B., Ghammamy, Sh., Gholipour, Z., and Amini Nia, A., Gold/Hydroxypropyl Cellulose Hybrid Nanocomposite Constructed with More Complete Coverage of Gold Nano-Shell, Mic & Nano Lett., Vol. 6, 2011, pp. 209-213.
[25] Sadeghi, B., Preparation of ZnO/Ag Nanocomposite and Coating on Polymers for Anti-Infection Biomaterial Application, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy., Vol. 118, 2014, pp. 787-792.
[26] Sadeghi, B., Controlled Growth and Characterization Ag/ZnO Nanotetrapods for Humidity Sensing, Comb. Chem. & High throughput Screening., Vol. 21, 2018, pp. 1-6.
[27] Sadeghi, B., Meskinfam, M., A Direct Comparison of Nanosilver Particles and Nanosilver Plates for The Oxidation of Ascorbic Acid, Spectrochim. Acta Part A: Molec. Biomolec. Spectros., Vol. 97, 2012, pp. 326-328.
[28] Vahdat, S. M., Ghafouri Raz, Sh., and Baghery, S., Application of nano SnO2 as a Green and Recyclable Catalyst for The Synthesis of 2-aryl or Alkylbenzoxazole Derivatives Under Ambient Temperature, J. Chem. Sci., Vol. 126, 2014, pp. 579-585.
[29] Vahdat, S. M., Chekin, F., Hatami, M., Khavarpour, M., Baghery, S., and Roshan-Kouhi, Z., Synthesis of Polyhydroquinoline Derivatives Via a Four-Compone, Chin. J. Catal., Vol. 34, 2013, pp. 758-763.
[30] Zolfigol, M. A., Baghery, S., Moosavi-Zare, A. R., Vahdat, S. M., Alinezhad, H., and Norouzi, M., Design of 1-Methylimidazolium Tricyanomethanide as The First Nanostructured Molten Salt and Its Catalytic Application in The Condensation Reaction of Various Aromatic Aldehydes, Amides And β-Naphthol Compared with Tin Dioxide Nanoparticles, RSC Adv., Vol. 5, 2015, pp. 45027-45037.
[31] Liu, Ch., Li, J., Liew, K., Zhu, J., and Bin Nordin, M. R., An Environmentally Friendly Method for The Synthesis of Nano-Alumina with Controllable Morphologies, J. RSC Adv., Vol. 2, 2015, pp. 8352–8358.
[32] Wuy, Y. S., Ma, J., Hu, F., and Li, M. C., Synthesis and Characterization of Mesoporous Alumina Via a Reverse Precipitation Method, J. Mater. Sci. Technol., Vol. 28, 2011, pp. 572-576.
[33] Sun, X., Li, J., Zhang, F., Qin, X., Xiu, Zh., and H. Ru, H., Synthesis of Nanocrystalline γ-Al2O3 Powders from Nanometric Ammonium Aluminum Carbonate Hydroxide, J. Am. Ceram. Soc., Vol. 86, 2003, pp. 1321-1325.
[34] Xiuhong, M., Linhai, D., Xiaohua, X., Qiang, W., and Haiyan, W., Synthesis of Macro Mesostructured γ-Al2O3 with Large Pore Volume and High Surface Area by A Facile Secondary Reforming Method, J. China Petrol. Process. Petrochem. Technol., Vol. 16, 2014, pp. 20-28.
[35] Zhu, Zh., Sun, H., Liu, H., and Yang, D., PEG-Direct Hydrothermal Synthesis of Alumina Nanorods with Mesoporous Structure via AACH Nanorod Precursors, J. Mater. Sci., Vol. 45, 2010, pp. 46-54.
[36] Gerrard, D. L., Maddams, W. F., The Resonance Raman Spectrum of Degraded Poly (Vinyl Chloride), 2. γ-Irradiated Samples, Macromolecules, Vol. 10, 1977, pp. 1221-1224.
[37] Ganesan, D., Samikanno, A., Muthaiah, Ch., and Ramasamy, K. M., Synthesis and Characterization of CdS Nanoparticle Anchored Silica-Titania Mixed Oxide Mesoporous Particles: Efficient Photocatalyst for Discoloration of Textile Effluent, Int. J. Nano Dimens., Vol. 10, 2019, pp. 272-280.
[38] Rajesh Krishnan, G., Sreeraj, M. K., and Sreekumar, K., Modification of Poly (Vinyl Chloride) With Pendant Metal Complex for Catalytic Applications, C. R. Chimie., Vol. 16, 2013, pp. 736-741.
[39] Huang, G., He, E., Wang, Z., Fan, H., Shangguan, J., Croiset, E., and Chen, Z., Synthesis and Characterization ofγ Fe2O3for H2S Removal at Low Temperature, Ind. Eng. Chem. Res., Vol. 54, 2015, pp. 8469-8478.
[40] Mehdizadeh, R., Saghatforoush, L. A., and Sanati, S., Solvothermal Synthesis and Characterization of α-Fe2O3 Nanodiscs and Mn3O4 Nanoparticles with 1,10-Phenanthroline, Superlatt. Microstruct., Vol. 52, 2012, pp. 92-98.
[41] Rajput, J, K., Kaur, G., CoFe2O4 Nanoparticles: An Efficient Heterogeneous Magnetically Separable Catalyst For “Click” Synthesis of Arylidene Barbituric Acid Derivatives at Room Temperature, Chin. J. Catal., Vol. 34, 2013, pp. 1697-1704.
[42] Schafer, H., Milow, B., and Ratke, L., Synthesis of Inorganic Aerogels Via Rapid Gelation Using Chloride Precursors, RSC Adv., Vol. 3, 2013, pp. 15263-15272.
[43] Khan, K. M., Ali, M., Farooqui, T. A., Khan, M., Taha, M., and Perveen, S., An Improved Method for The Synthesis of 5-Arylidene Barbiturates Using BiCl3, J. Chem. Soc. Pak., Vol. 31, 2009, pp. 823-828.
[44] Alcerreca, G., Sanabria, R., Miranda, R., Arroyo, G., Tamariz, J., and Delgado, F., Preparation of Benzylidene Barbituric Acids Promoted by Infrared Irradiation in Absence of Solvent, Synth. Commun., Vol. 30, 2000, pp. 1295-1301.
[45] Quinonero, D., Ferontera, A., Benzen, An Unexpected Binding Unit in Anion-π Recognition: The Critical Role of CH/π Interactions, Sci. Vol. 4, 2022, pp. 32-36.
[46] Katarzyna, O., Katarzyna, M. S., Marlena, G., Oskar, K., Mateusz, Z. B., Piotr, G., Michał, L., Rosław, G., and Agnieszka, W., Influence of Hydrogen Bonds and π–π Interactions on the Fluorescence of Crystalline (N-Alkylpyridyl) enamino-pyrrolo [2,3-b] Quinoxalin-2-One Derivatives, Crys. Growth Des., Vol. 22, 2022, pp. 1571-1582.
Int. J. Advanced Design and Manufacturing Technology, 2023, Vol. 16, No. 4, pp. 79-85
DOI: 10.30486/ADMT.2023.873774 ISSN: 2252-0406 https://admt.isfahan.iau.ir
Experimentally Designed of PVC/NiAl2O3/AlF3 Nanocomposite by Sol-Gel Method
Elinaz Ahmadian, Maryam Kargar Razi *
Department of Chemistry, Islamic Azad University,
North Tehran Branch, Tehran, Iran
Email: elina2964@yahoo.com, mkargarrazi@yahoo.com
*Corresponding author
Babak Sadeghi
Department of Chemistry, Islamic Azad University,
Tonekabon Branch, Tonekabon, Iran
Email: bsadeghi1177@gmail.com
Mahbobeh Nakhaei
Department of Chemistry, Islamic Azad University,
North Tehran Branch, Tehran, Iran
Email: mnakhaeia@gmail.com
Received: 24 September 2023, Revised: 28 November 2023, Accepted: 30 November 2023
Abstract: In this study, we have synthesized nano Aluminum Fluoride (nAF) nanoparticles by the sol-gel method and studied the nano-sized morphology of crystals. In the other section, the PVC/NiAl2O3/AlF3 (nPNA) nanocomposite was successfully prepared and characterized by FT-IR, and HRTEM techniques. FTIR peaks of the PVC and nPNA have been shown spherical shape of PVC and also spherical shapes nanoparticles of nPNA loaded on PVC. A solvothermal method has been successfully introduced and applied for catalyst efficiency. This nanocomposite was used for the removal of Congo red dye. For this purpose, the morphology and the structure of crystals have been changed by modification on precursor gel. Meanwhile, precursor gel preparation and the interaction on the nano-sized area have been studied. This study exhibited that PVC/NiAl2O3/AlF3 (nPNA) nanocomposite is an effective catalyst for the synthesis of some organic derivatives. The results show that the as-prepared nanocomposite is an efficient catalyst and that PVC/NiAl2O4/AlF3 nanocomposite can be used in the next-generation of some organic reactions and faster production of various materials.
Keywords: Nano Catalytic activity, Nano-Size, Morphology, Sol-gel, TEM
Biographical notes: Maryam Kargar Razi received her Postdoc in Inorganic Chemistry and Glass University of Friedrich Schiller University in Germany, and PhD in Inorganic Chemistry University of IAU Science and Research Branch in 2000. She is currently an Assistant Professor at the Department of Chemistry, North Tehran University, and Tehran, Iran. Babak Sadeghi is Associate Professor of Inorganic Chemistry at the University of Tonekabon, Iran. He received her PhD in Inorganic Chemistry from IAU Science and Research Branch, Iran in 2004. His current research focuses on the Synthesis of Nano Materials. Elinaz Ahmadian is PhD student at the Department of Chemistry, North Tehran University, and Tehran, Iran. Mahbobeh Nakhaei is Assistant Professor at the Department of Chemistry, North Tehran University, and Tehran, Iran.
Synthesis of the sol-gel method has been so widely developed that nano-metal oxides, either pure or organic-inorganic hybrid materials, are applied and available now [1-8]. One of the most common applications of Al2O3 and nAlF3 (and their derivatives) is as a catalyst support. Many physical properties of the catalyst support, such as temperature, pH, aging time, raw materials and preparation technique, have a major impact on the performance of the catalyst in sol-gel processes [9-11]. Ono et al. [12] were the first to report this procedure and they managed to study the effectiveness of the pH and number of pH-swing frequencies on the Aluminium Oxide formation. Maity et al. [13] prepared the catalyst supported by alumina via various techniques, such as pH-swing, and determined that this method improved the pore size distribution (PSD). [14].
Aluminum fluoride has a number of current and potential applications as an additive to the molten electrolyte of the aluminum production cell in order to lower the melting point and increase the electrical conductivity. Moreover, among metal fluoride catalysts and catalyst supports for halogen exchange reactions, AlF3 is one of the most important catalysts [15-18]. We have recently developed a reduction method of converting Ag nanospheres into nanorods [19], nanoplates [20], their antibacterial activity [21-22], an improved and easy synthetic route for silver nanoparticles in poly (diallyldimethylammonium chloride) (PDDA) [23], synthesis of Gold/HPC hybrid nanocomposite [24], preparation of Ag/ZnO nanocomposite [25-26] and comparison nanosilver particles and nanosilver plates for the oxidation of ascorbic acid [27].
As part of our efforts to investigate the usefulness of nanocomposite catalysts for the synthesis of organic and heterocyclic compounds [28-30], we report an efficient process for the synthesis of arylidende barbituric acid derivatives from the cyclo-condensation reaction between barbituric acid, various aldehydes by using 1 mol% ammonia mediated at room temperature. In the present paper, nPNA composite was successfully prepared (from nAF) and then, catalytic activity of nPNA has been considered in the synthesis of two organic derivatives.
2 EXPERIMENTAL
2.1. Characterization
Transmission electron microscopy (TEM, Model Hitachi 4500-M) was used to study morphology and particle size. It was performed using Bruker AXS diffractometer D8 ADVANCE with Cu-Kα radiation in the range 2θ=10º–80º. FT-IR spectra of the samples were done using a spectrometer (Model Perkin–Elmer) in the wavelength range 400-4000 cm-1.
2.2. Materials and Methods
Baribituric acid (BBA) and various aldehydes were purchased from Aldrich company and used as received without further purification. Solution pH ranged between 7 and 10. The resulting gel nAF was kept at 50 ºC for 20 h. Then, obtained gel were filtered and rinsed with a NH3.
2.3. Catalytic Activity
The catalytic activity of the PVC/NiAl2O4/AlF3 (nPNA) was shown as below optimization procedure. BBA, nPNA, and methanolic solution of various benzaldehydes were added to hot water and stirred until the color precipitate of the products has been prepared. The precipitate of solid was filtered. A solvothermal method has been successfully introduced and applied for catalyst efficiency. The ABBA derivatives have been characterized by FT-IR spectroscopy.
2.4. Result and Discussion
During the preparation, the chemical reactions (reaction 1) that occurred are highlighted as changes in the various crystalline phases observed in the XRD pattern. It can therefore be said that Nano Aluminum fluoride (nAF) was utilized in this sample as precipitant [15-16].
alkaline regions
Al (CH3COO)3 + Al2O2F4 + 5HF 3nanoAlF3 + 3 CH3COOH + H2 + O2 (NH3 Solvent) (1)
In glass reactor (nAF)
Fig. 2 HR TEM images of the nAlF3 sample.
Figure 1 (a, b) represents the HRTEM direct image of nAlF3 sample. The size of the particle is spherical in shape and has a size in the range of 10-18 nm which was a good similarity to the size obtained in the optical model. TEM images were prepared to determine the produced nanoparticles' size, morphology, and uniformity. The results showed the production of hexagonal nAlF3 nanoparticles, and it matches the XRD patterns.
The FTIR spectrum of nAlF3 is shown in “Fig. 2”. In this sample, there is not broad absorption bands at 3300-3500 cm-1 associated with O-H stretching of adsorbed water. The sharp peak at 1645 cm-1 belongs to the bending vibration of H-OH in (a small amount of water) H2O molecules. The band at 1075 cm-1 is related to symmetrical Al-F bending modes. The adsorption peak at 1635 cm-1 belongs to the bending vibration of O-H group in the adsorbed water [31-35].
Fig. 2 FTIR spectrum of the nano AlF3.
PVC/NiAl2O4/AlF3 (nPNA) nanocomposite was prepared using the reaction of PVC, AlCl3, and NiCl2 in the presence of NaOH. The chemical structure of PVC and PVC/NiAl2O4/AlF3 was studied by FT-IR spectroscopy and the results are presented in “Fig. 3”.
Fig. 3 FT-IR spectra of: (a): PVC, and (b): PVC/NiAl2O4/AlF3 composite.
The absorption bands in the infrared spectrum of polyvinyl chloride at 503, and 650 cm-1 are assigned to the amorphous absorption band of C–Cl stretching, and C–Cl crystalline absorption band, respectively. The υ(C–C) stretching vibrations band has been showed around 845. The bands at 1100 and 1175 cm-1 correspond to perpendicular chain stretch and parallel chain stretch [36]. The absorption band at 1359 cm-1 corresponds to CH2 wag and the other band at
1430 cm-1 is due to the bending mode of CH2. The absorption band at 1631 cm-1 is assigned to the carbon=carbon double bond stretching vibration for conjugated bonds, or either aromatic or aliphatic or both. The band at 1724 cm-1 is probably from the carbonyl stretching vibration. The wideband at 2925 cm-1 corresponds to the CH2 asymmetric stretching mode, the peak broadening is due to the intermolecular and intra-molecular hydrogen bonds [37]. However, the small shift in 650, 845, and 1724 cm-1 band positions confirmed the formation of PVC/NiAl2O4/AlF3 nanocomposite in the PVC polymer matrix. The peaks at 689, 614, and 427 cm-1 concerning Metal-O (Al-O and Ni-O) stretching [38-40].
2.5. Catalytic Activity of Arylidene Barbituric Acid Derivatives
The color of barbituric acid is white, while the color of FCG-1 (R=COOH) is pale-brown and FCG-2 (R=NH2) is orange. The melting point of FCG-1 is about 293 ºC and is more than the melting point of FCG-2 (223 ºC), due to the COOH group that causes increasing hydrogen bond strength in FCG-2.
“Table 1” shows the conditions for the synthesis of ABBA, under various derivatives. The yield of the products is very low in acetonitrile, dichloromethane and is a medium in methanol and water, while the yield increased to ≥ 97% using a water-methanol (l: 1 v/v) mixture. Preparation of FCG-2 (40 sec) is faster than FCG-1 (210 sec) because NH2 is an electron donor while COOH is an electron acceptor. The results presented in this article are a continuation of previous works [41]. For example, the yield and time for the preparation of FCG-2 (entry 2 in “Table 1”) are higher than this compound prepared by Rajput and Kaur [41]. By increasing the catalyst, the yield of FCG-1 and FCG-2 increased from 82 to 92 and 90 to 97%. Also, by changing the solvent from methanol to methanol-water, the yield of FCG-1 and FCG-2 increased. In the absence of the PVC/NiAl2O4/AlF3, only a trace (< 50%) of FCG-1 and FCG-2 was obtained which is in agreement with previous reports [42]. This reaction has been monitored by the formation of colored precipitate product and is simple, and clean. The purified compounds have been recrystallized and characterized by FT-IR and UV-vis spectroscopies. Until now, there have been many reports on the preparation of arylidene barbituric acid by various catalysts [41], [43-46].
Table 1 Optimization of the preparation of arylidene barbituric acid derivatives
Entry | R | Time (min) | Yield (%) | Catalyst amount (g) | Solvent |
|
| Arylidene | Barbituric | Acid Derivatives |
|
1 | COOH | 4 | 92 | 0.03 | Methanol-Water (1: 1) |
2 | NH2 | 1 | 97 | 0.03 | Methanol-Water (1: 1) |
3 | COOH | 6 | 82 | 0.02 | Methanol-Water (1: 1) |
4 | NH2 | 2 | 90 | 0.02 | Methanol-Water (1: 1) |
5 | COOH | 17 | 80 | 0.03 | Methanol |
6 | NH2 | 6 | 89 | 0.03 | Methanol |
7 | COOH | 27 | 77 | 0.02 | Methanol |
8 | NH2 | 9 | 80 | 0.02 | Methanol |
3 Conclusions
In conclusion, a multi-step precipitation method with the sol-gel technique was implemented. The TEM images and FT-IR spectroscopy indicated that the prepared nAlF3 had low crystallinity and images showed that particle size is nanometer scale. Using the TEM images, the crystal size of the sample was 19.5 nm. The FT-IR spectroscopy confirmed the formation of nAlF3 and PVC/NiAl2O4/AlF3 nanocomposite in PVC polymer matrix. nPNA has been prepared and used as a new catalyst for the preparation of ABBA. The result confirmed that the nPNA composite is a good catalyst. This catalyst produces the FCG-1 and FCG-2 compounds in a very short time and with high yields. FTIR peaks of the PVC and nPNA have been shown spherical shape of PVC and also spherical shapes of nanoparticles of nPNA loaded on PVC. The main information from this study can be fixed or altered to optimize responses at more levels for future studies. These results show that PVC/NiAl2O4/AlF3 nanocomposite can be used in next-generation of some organic reactions and faster production of various materials.
4 ACKNOWLEDGMENTS
The financial and encouragement support was provided by the Research vice Presidency of North Tehran & Tonekabon Branch, Islamic Azad University, and Executive Director of Iran-Nanotechnology Organization (Govt. of Iran).
5 CONFLICTS OF INTEREST
The authors declare that there are no conflicts of interest regarding the publication of this manuscript.
REFERENCES
[1] Turner, M. E., Trentler, T. J., and Colvin, V. L., Thin Films of Macroporous Metal Oxides, Adv. Mater., Vol. 13, 2001, pp. 180-183.
[2] Aguado, J., Serrano, D. P., Escola, J. M., Garagorri, E., and Fernandez, J. A., Catalytic Cracking of a Polyolefin Mixture Over Different Acid Solid Catalysts, Polym. Degrad. Stabil., Vol. 69, 2000, pp. 11-16.
[3] Gronchi, P., Kaddouri, A., Centola, P., and Del Rosso, R., Synthesis of Nickel Supported Catalysts for Hydrogen Production by Sol-Gel Method, J. Sol-Gel Sci. Tech., Vol. 26, 2003, pp. 843-846.
[4] L. Khelifi, L., Ghorbel, A., Effect of Preparation Conditions on the Stability of Pt/Al2O3 Catalysts in Methane Combustion, J. Sol-Gel Sci Tech., Vol. 19, 2000, pp. 643-646.
[5] Meixner, H., Lampe, U., Gerblinger, J., and Fleische, M., Chemosensors for Motor Management Systems of The Future, Fresenius J. Anal. Chem., Vol. 348, 1994, pp. 536-541.
[6] Bennett, R. A., McCavish, N. D., Non-Stoichiometric Oxide Surfaces and Ultra-Thin Films: Characterisation of TiO2, Topics in Catalysis. Vol. 36, 2005, pp. 11-19.
[7] Chemistry of Advanced Materials: An Overview, Wiely-VCH, Inc, Canada, 1998, Chapt. 9, Molecular Precursor Routes to Inorganic Solids, pp. 389–448.
[8] Righini, G. C., Pelli, S., Nonlinear Properties of Semiconductor-Doped Silica Solgel Films, J. Sol-Gel Sci. Tech., Vol. 8, 1997, pp. 991–997.
[9] Maryani, E., Abdullah, M., Dayamanti, H., and Septawendar, R., Effect of Ultrasonic Irradiation on The Characteristic of γ-Al2O3 Nanorods Synthesized from Nitrate Salt-Starch Precursors Trough a Facile Precipitation Method, J. Ceram. Soc. Japan., Vol. 124, 2016, pp. 1205-1210.
[10] Amirsalari, Farjami, S., Effect of pH and Calcinations Temperature on Structural and Optical Properties of Alumina Nanoparticles, J. Superlatt. Microstruct. Vol. 82, 2015, pp. 507-524.
[11] Da-Ros, S., Barbosa-Coutinho, E., Schwaab, M., Calsavara, V., and Fernandes-Machado, N. R. C., Modeling the Effects of Calcination Conditions on The Physical and Chemical Properties of Transition Alumina Catalysts, J. Mater. Character., Vol. 80, 2013, pp. 50-61.
[12] Tayseir Mohammed, E., Saikat, M., Some Studies on The Surface Modification of Sol-Gel Derived Hydrophilic Silica Nanoparticles, Int. J. Nano Dimens., Vol. 8, 2017, pp. 97-106.
[13] Maity, S. K., Ancheyta, J., and Rana, M. S., Support Effects on Hydroprocessing of Maya Heavy Crude, J. Energy and Fuel., Vol. 19, 2005, pp. 343-347.
[14] Fernandez., V. C., Ramrez, J., Alejandre, A. G., Sanchez-Minero, F., Cuevas-Garcıa, R., and Torres-Mancera, P., Synthesis, Characterization and Evaluation of NiMo/SiO2–Al2O3 Catalysts Prepared by the pH-Swing Method, J. Catal. Today., Vol. 130, 2008, pp. 337–344.
[15] Dao Quan, H., Yang, H., Tamura, M., and Sekiya., A., SbF5/PAF—a Novel Fluorinating Reagent in Preparing Fluorine Compounds, J. Fluorine Chem., Vol. 125, 2004, pp. 1169-1172.
[16] Sekiya, dao Quan, H., Tamura, M., Gao, R. X., and Murata, J., Sol-Gel Synthesis and Catalytic Properties of PVC/NiAl2O3/AlF3 Nanocomposite", J. Fluorine Chem., Vol. 112, 2001, pp. 145-148.
[17] Dao Quan, H., Tamura, M., Takagi, T., and Sekiya, A., Fluorination of N-Dodecane Adsorbed on Porous Aluminium Fluoride by Gaseous Fluorine, J. Fluorine Chem., Vol. 99, 1999, pp. 167-170.
[18] Krespan, C. G., Dixon, D. A., Fluoroolefin Condensation Catalyzed by Aluminum Chlorofluoride, J. Fluorine Chem., Vol. 77, 1996, pp. 117-126.
[19] Sadjadi, M. A. S., Sadeghi, B., Meskinfam, M., Zare, K., and Azizian, J., Synthesis and Characterization of Ag/PVA Nanorods By Chemical Reduction Method, Physica E: Low-Dimensional Systems and Nanostructures, Vol. 40, 2008, pp. 3183-3186.
[20] Sadeghi, B., Sadjadi, M. A. S., and Vahdati, R. A. R., Nanoplates Controlled Synthesis and Catalytic Activities of Silver Nanocrystals, Superlattices and Microstructures, Vol. 46, 2009, pp. 858-863.
[21] Sadeghi, B., Jamali, M., Kia, Sh., Amini Nia, A., and Ghafari., S., Synthesis and Characterization of Silver Nanoparticles for Antibacterial Activity, Int. J. Nano Dimens., Vol. 1, 2010, pp. 119-124.
[22] Sadeghi, B., Garmaroudi, F. S., Hashemi, M., Nezhad, H. R., Nasrollahi, A., Ardalan, S., and Ardalan, S., Comparison of the Anti-Bacterial Activity on The Nanosilver Shapes: Nanoparticles, Nanorods and Nanoplates, Adv. Powder Technol., Vol. 23, 2012, pp. 22-26.
[23] Sadeghi, B., Pourahmad, A., Synthesis of Silver/Poly (Diallyl Dimethyl Ammonium Chloride) Hybride Nanocomposite, Adv. Powder Tech., Vol. 22, 2012, pp. 669-673.
[24] Sadeghi, B., Ghammamy, Sh., Gholipour, Z., and Amini Nia, A., Gold/Hydroxypropyl Cellulose Hybrid Nanocomposite Constructed with More Complete Coverage of Gold Nano-Shell, Mic & Nano Lett., Vol. 6, 2011, pp. 209-213.
[25] Sadeghi, B., Preparation of ZnO/Ag Nanocomposite and Coating on Polymers for Anti-Infection Biomaterial Application, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy., Vol. 118, 2014, pp. 787-792.
[26] Sadeghi, B., Controlled Growth and Characterization Ag/ZnO Nanotetrapods for Humidity Sensing, Comb. Chem. & High throughput Screening., Vol. 21, 2018, pp. 1-6.
[27] Sadeghi, B., Meskinfam, M., A Direct Comparison of Nanosilver Particles and Nanosilver Plates for The Oxidation of Ascorbic Acid, Spectrochim. Acta Part A: Molec. Biomolec. Spectros., Vol. 97, 2012, pp. 326-328.
[28] Vahdat, S. M., Ghafouri Raz, Sh., and Baghery, S., Application of nano SnO2 as a Green and Recyclable Catalyst for The Synthesis of 2-aryl or Alkylbenzoxazole Derivatives Under Ambient Temperature, J. Chem. Sci., Vol. 126, 2014, pp. 579-585.
[29] Vahdat, S. M., Chekin, F., Hatami, M., Khavarpour, M., Baghery, S., and Roshan-Kouhi, Z., Synthesis of Polyhydroquinoline Derivatives Via a Four-Compone, Chin. J. Catal., Vol. 34, 2013, pp. 758-763.
[30] Zolfigol, M. A., Baghery, S., Moosavi-Zare, A. R., Vahdat, S. M., Alinezhad, H., and Norouzi, M., Design of 1-Methylimidazolium Tricyanomethanide as The First Nanostructured Molten Salt and Its Catalytic Application in The Condensation Reaction of Various Aromatic Aldehydes, Amides And β-Naphthol Compared with Tin Dioxide Nanoparticles, RSC Adv., Vol. 5, 2015, pp. 45027-45037.
[31] Liu, Ch., Li, J., Liew, K., Zhu, J., and Bin Nordin, M. R., An Environmentally Friendly Method for The Synthesis of Nano-Alumina with Controllable Morphologies, J. RSC Adv., Vol. 2, 2015, pp. 8352–8358.
[32] Wuy, Y. S., Ma, J., Hu, F., and Li, M. C., Synthesis and Characterization of Mesoporous Alumina Via a Reverse Precipitation Method, J. Mater. Sci. Technol., Vol. 28, 2011, pp. 572-576.
[33] Sun, X., Li, J., Zhang, F., Qin, X., Xiu, Zh., and H. Ru, H., Synthesis of Nanocrystalline γ-Al2O3 Powders from Nanometric Ammonium Aluminum Carbonate Hydroxide, J. Am. Ceram. Soc., Vol. 86, 2003, pp. 1321-1325.
[34] Xiuhong, M., Linhai, D., Xiaohua, X., Qiang, W., and Haiyan, W., Synthesis of Macro Mesostructured γ-Al2O3 with Large Pore Volume and High Surface Area by A Facile Secondary Reforming Method, J. China Petrol. Process. Petrochem. Technol., Vol. 16, 2014, pp. 20-28.
[35] Zhu, Zh., Sun, H., Liu, H., and Yang, D., PEG-Direct Hydrothermal Synthesis of Alumina Nanorods with Mesoporous Structure via AACH Nanorod Precursors, J. Mater. Sci., Vol. 45, 2010, pp. 46-54.
[36] Gerrard, D. L., Maddams, W. F., The Resonance Raman Spectrum of Degraded Poly (Vinyl Chloride), 2. γ-Irradiated Samples, Macromolecules, Vol. 10, 1977, pp. 1221-1224.
[37] Ganesan, D., Samikanno, A., Muthaiah, Ch., and Ramasamy, K. M., Synthesis and Characterization of CdS Nanoparticle Anchored Silica-Titania Mixed Oxide Mesoporous Particles: Efficient Photocatalyst for Discoloration of Textile Effluent, Int. J. Nano Dimens., Vol. 10, 2019, pp. 272-280.
[38] Rajesh Krishnan, G., Sreeraj, M. K., and Sreekumar, K., Modification of Poly (Vinyl Chloride) With Pendant Metal Complex for Catalytic Applications, C. R. Chimie., Vol. 16, 2013, pp. 736-741.
[39] Huang, G., He, E., Wang, Z., Fan, H., Shangguan, J., Croiset, E., and Chen, Z., Synthesis and Characterization ofγ‑Fe2O3for H2S Removal at Low Temperature, Ind. Eng. Chem. Res., Vol. 54, 2015, pp. 8469-8478.
[40] Mehdizadeh, R., Saghatforoush, L. A., and Sanati, S., Solvothermal Synthesis and Characterization of α-Fe2O3 Nanodiscs and Mn3O4 Nanoparticles with 1,10-Phenanthroline, Superlatt. Microstruct., Vol. 52, 2012, pp. 92-98.
[41] Rajput, J, K., Kaur, G., CoFe2O4 Nanoparticles: An Efficient Heterogeneous Magnetically Separable Catalyst For “Click” Synthesis of Arylidene Barbituric Acid Derivatives at Room Temperature, Chin. J. Catal., Vol. 34, 2013, pp. 1697-1704.
[42] Schafer, H., Milow, B., and Ratke, L., Synthesis of Inorganic Aerogels Via Rapid Gelation Using Chloride Precursors, RSC Adv., Vol. 3, 2013, pp. 15263-15272.
[43] Khan, K. M., Ali, M., Farooqui, T. A., Khan, M., Taha, M., and Perveen, S., An Improved Method for The Synthesis of 5-Arylidene Barbiturates Using BiCl3, J. Chem. Soc. Pak., Vol. 31, 2009, pp. 823-828.
[44] Alcerreca, G., Sanabria, R., Miranda, R., Arroyo, G., Tamariz, J., and Delgado, F., Preparation of Benzylidene Barbituric Acids Promoted by Infrared Irradiation in Absence of Solvent, Synth. Commun., Vol. 30, 2000, pp. 1295-1301.
[45] Quinonero, D., Ferontera, A., Benzen, An Unexpected Binding Unit in Anion-π Recognition: The Critical Role of CH/π Interactions, Sci. Vol. 4, 2022, pp. 32-36.
[46] Katarzyna, O., Katarzyna, M. S., Marlena, G., Oskar, K., Mateusz, Z. B., Piotr, G., Michał, L., Rosław, G., and Agnieszka, W., Influence of Hydrogen Bonds and π–π Interactions on the Fluorescence of Crystalline (N-Alkylpyridyl) enamino-pyrrolo [2,3-b] Quinoxalin-2-One Derivatives, Crys. Growth Des., Vol. 22, 2022, pp. 1571-1582.
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