ORIGINAL_ARTICLE
The possibility of a two-step oxidation of the surface of C20 fullerene by a single molecule of nitric (V) acid
< p>Oxidation of fullerenes, carbon nanotubes, and graphene, is one of the first proposed and successful approaches for further functionalization of these nano dimension carbon allotropes. Also, the C20 fullerene, as the smallest known carbon cage, is one of the most important species, in the future of nanotechnology. In this regard, the potential energy surface (PES) study suggests that reaction between nitric (V) acid and C20 fullerene, first leads to the production of a relatively meta-stable kinetically allowed intermediate via a [2+3] cycloaddition. After the intermediate is produced, it would subsequently be decomposed to a C20O open-shell fullerene and a HNO2molecule. Such oxidations were observed via the reaction between strong acids and some of the nano-sized carbon allotropes like carbon nanotube CNTs or spherical fullerenes. The results showed that the produced intermediate directly changes to the final product of oxidation, in a fast process.
https://www.chemrevlett.com/article_85535_06fb2ad9b3ec1405d88e8317a9bfbb9e.pdf
2019-02-01
2
6
nitric (V) acid
C20 fullerene
molecular mechanism
PES
reaction channels
Seyyed Amir
Siadati
chemistry_2021@yahoo.com
1
Department of Chemistry, Qaemshahr Branch, IslamicAzadUniversity, Qaemshahr, Iran
AUTHOR
Karolina
Kula
2
Institute of Organic Chemistry and Technology, Cracow University of Technology, Cracow, Poland
AUTHOR
Esmaiel
Babanezhad
3
Department of EnvironmentalHealth, Faculty of Health, Mazandaran University of Medical Sciences, Sari, Iran
AUTHOR
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b) S.A. Siadati, E. Vessally, A. Hosseinian, L. Edjlali,Possibility of sensing, adsorbing, and destructing the Tabun-2D-skeletal (Tabun nerve agent) by C20 fullerene and its boron and nitrogen doped derivatives, Syn. Met. 220 (2016) 606-611;
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c) S.A. Siadati, A Theoretical Study on the Possibility of Functionalization of C20 Fullerene via its Diels-Alder Reaction with 1, 3-Butadiene, Lett. Org. Chem.13 (2016) 2-6;
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d) S.A. Siadati, N. Navabeh, Investigation of the possibility of functionalization of C20 fullerene by benzene via Diels–Alder reaction, Physica E: Low-dimens. Syst. 84 (2016) 55-59.
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b) S.A. Siadati, A. Mirabi, Diels–Alder versus 1, 3-dipolar cycloaddition pathways in the reaction of C20 fullerene and 2-furan nitrile oxide, Prog. React. Kin. Mech. 40 (2015) 383-390;
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c) P. Pakravan, S.A. Siadati, The possibility of using C20 fullerene and graphene as semiconductor segments for detection, and destruction of cyanogen-chloride chemical agent, J Mol. Graph. Model. 75 (2017) 80-84.
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49
ORIGINAL_ARTICLE
Synthesis of bis coumarinyl methanes using of potassium 2-oxoimidazolidine-1,3-diide as a novel, efficient and reusable catalyst
At first, potassium 2-oxoimidazolidine-1,3-diide (POImD) was prepared of stirring a mixture of imidazolidin-2-one, KOH and H2O overnight. Then, Potassium 2-oxoimidazolidine-1,3-diide was used as a green, novel, fast, efficient and mild catalyst for the synthesis of bis coumarinyl methanes via a one-pot reaction of one equivalent of various aromatic aldehydes and two equivalents of 4-hydroxycoumarin at room temperature in aqueous media. All reactions are performed in the absence of organic solvent in high to excellent yield during short reaction time. The procedure was readily conducted and affords remarkable advantages such as simple work-up, green media and eco-friendly procedure. The catalyst was recovered and reused. Apart from the mild conditions of the process and its excellent results, the simplicity of product isolation and the possibility to recycle the catalyst offer a significant advantage. To the best of our knowledge this is the first report on synthesis of POImD. All of synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy and elemental analyses.
https://www.chemrevlett.com/article_85819_14373b6eaa87d1c6de6a9fd5ca2679e0.pdf
2019-02-01
7
12
10.22034/crl.2019.85819
Coumarin
Potassium 2-oxoimidazolidine-1
3-diide
Multicomponent reaction
4-Hydroxycoumarin
Mohammad
Nikpassand
1
aDepartment of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran
AUTHOR
Leila
Zare Fekri
2
bDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
AUTHOR
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[4] M. I. Choudhary, N. Fatima, K. M. Khan, S. Jalil, S. Iqbal and Atta-ur-Rahman, New biscoumarin derivatives-cytotoxicity and enzyme inhibitory activities. Bioorg. Med. Chem., 14 (2006) 8066-8072.
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[8] M. K. Mohammadi, S. J. Saghanezhad and N. Razzaghi-asl, Efficient and convenient oxidation of benzyl halides to carbonyl compounds with Sodium nitrate and Acetic acid by phase transfer catalysis in aqueous media. Bull. Chem. Soc. Ethiop., 31 (2017) 535-544.
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[12] M. Nikpassand, L. Zare Fekri, L. Karimian and M. Rassa, Synthesis of biscoumarin derivatives using nanoparticle Fe3O4 as an efficient reusable heterogeneous catalyst in aqueous media and their antimicrobial activity. Curr. Org. Synth., 12 (2015) 358-362.
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[13] M. Nikpassand, L. Zare Fekri and P. Farokhian, An efficient and green synthesis of novel benzoxazole under ultrasound irradiation. Ultrason. Sonochem., 28 (2016) 341-345.
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[14] L. Zare Fekri, M. Nikpassand and R. Maleki, 1, 4-Diazabicyclo [2.2. 2] octanium diacetate: As an effective, new and reusable catalyst for the synthesis of benzo [d] imidazole. J. Mol. Liq., 222 (2016) 77-81.
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[15] V. Padalkar, K. Phatangare, S. Takale, R. Pisal and A. Chaskar, Silica supported sodium hydrogen sulfate and Indion 190 resin: An efficient and heterogeneous catalysts for facile synthesis of bis-(4-hydroxycoumarin-3-yl) methanes. J. Saudi Chem. Soc., 19 (2015) 42-45.
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[18] M. A. Zolfigol, A. R. Mousavi-Zare and M. Zarei, Friedel–Crafts alkylation of 4-hydroxycoumarin catalyzed by sulfonic-acid-functionalized pyridinium chloride as a new ionic liquid. Comptes Rendus Chimie., 17 (2014) 1264-1267.
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21
ORIGINAL_ARTICLE
Crystal structure and luminescence properties of a new nanostructure lead(II) complex: a precursor for preparation of pure phase nanosized PbO
The reaction of 1,3-diphenylpropane-1,3-dione (HL) ligand with lead(II) nitrate under hydrothermal conditions led to the formation of a novel lead complex with singular structural features. The characterization of title complex was performed by spectroscopy methods such as 1H NMR, UV, and IR and elemental analyses (CHN) and crystal structure of prepared lead (II) complex was determined by single-crystal X-ray diffraction. The facile and productive sonochemical method was used to prepare nano-size particles of the title complex at room temperature. The prepared nano-size-complex was characterized by elemental analysis, scanning electron microscopy (SEM), IR spectroscopy and X-ray powder diffraction (XRD). The nano-size lead oxides that prepared by calcination of the nano-size complex and crystalline bulk complex showed the initial particle size of the precursor is influential on the particle size of the derived PbO nanoparticles. Optical property investigation of the PbO nanoparticles at room temperature showed that the size of PbO nanoparticles has an important role on their optical behavior.
https://www.chemrevlett.com/article_86194_06b9d218f2a53fff8f51461c39328d60.pdf
2019-02-01
13
20
10.22034/crl.2019.86194
: Coordination polymer
Nanosize lead complex
Photoluminescence
Lead(II) oxide
Ezzatollah
Najafi
1
Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
LEAD_AUTHOR
Farnaz
Behmagham
2
Department of Chemistry, Miandoab Branch, Islamic Azad University, Miandoab, Iran
AUTHOR
Niloofar
Shaabani
3
Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
AUTHOR
Nasrin
Shojaei
4
Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
AUTHOR
[1] L. Aboutorabi,; A. Morsali,; Structural transformations and solid-state reactivity involving nano lead(II) coordination polymers via thermal, mechanochemical and photochemical approaches. Coord. Chem. 310 (2016) 116-130.
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[26] S. Suckert; H. Terraschke; H. Reinsch; C. Näther, Synthesis, crystal structures, thermal, magnetic and luminescence properties of Mn(II) and Cd(II) thiocyanate coordination compounds with 4-(Boc-amino)pyridine as co-ligand. Inorg. Chim. Acta. 461 (2017) 290-297.
26
[27] A.V. Savchenkov; M.S. Grigoriev, P.A. Udivankin; D.V. Pushkin, L.B. Serezhkina, Maleate ions as ligands in crystal structures of coordination compounds, including two uranyl complexes. Polyhedron. 127 (2017) 331-336.
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[28] M. Sumesh; U.J. Alengaram, M.Z. Jumaat, K.H. Mo, M.F. Alnahhal, Incorporation of nano-materials in cement composite and geopolymer based paste and mortar –A review. Constr. Build. Mater. 148 (2017) 62-84.
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[29] P.B. Taunk, R. Das, D.P. Bisen, R.K. Tamrakar, Synthesis and characterization of pure and Zn doped lead hydroxide nano structure through chemical root method. Optik. Int. J. Light. Electron. Opt.127 (2016) 4995-5012.
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[30] Q. Zhou, J. Qian, C. Zhang, Three interesting coordination compounds based on metalloligand and alkaline-earth ions: Syntheses, structures, thermal behaviors and magnetic property. J. Mol. Struct. 1119 (2016) 340-345.
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[31] K.F. Zare, V. Safarifard, K.S. Karbalaei, A. Morsali, Ultrasound-assisted synthesis of nano-structured 3D zinc(II) metal–organic polymer: Precursor for the fabrication of ZnO nano-structure. Ultrason. Sonochem. 23 (2015) 238-245.
31
[32] L. Zhou, X. Zhang, Y. Chen, Facile synthesis of Al-fumarate metal–organic framework nano-flakes and their highly selective adsorption of volatile organic compounds. Mater. Lett. 197 (2017) 224-227.
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[33] P. Zielke, Y. Xu, S.B. Simonsen, P. Norby, R. Kiebach, Simulation, design and proof-of-concept of a two-stage continuous hydrothermal flow synthesis reactor for synthesis of functionalized nano-sized inorganic composite materials . J. Supercrit. Fluids. 117 (2016) 1-12.
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[34] L. Zhang, Y. Zhou, G. Shi, X. Sang, C. Ni, Preparations of hyperbranched polymer nano micelles and the pH/redox controlled drug release behaviors. Mater. Sci. Eng. C. 79 (2017) 116-122.
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[35] H. Zhou, M. Su, P.H. Lee, K. Shih, Synthesis of submicron lead oxide particles from the simulated spent lead paste for battery anodes. J. Alloys. Compd. 690 (2017) 101-107.
35
ORIGINAL_ARTICLE
An experimental study of the corrosion Process of metals in virtue of crude oils and the characteristics
Crude oils are dominant earth resources since composed with large number of hydrocarbons and some of trace compounds especially with corrosive compounds such as sulfur compounds, naphthenic acids and salts. In the current research the major scope was the investigations of the impact of such corrosive compounds on the corrosion of seven different types of ferrous metals in both qualitatively and quantitatively. According to the methodology such corrosive properties of two different types of selected crude oils were analyzed and the chemical compositions of seven different types of selected ferrous metals were detected by the standard methodologies and recommended instruments. The corrosion rates of such metals were determined by the relative weight loss method after certain immersion time periods in both crude oil samples while analyzing the corroded metal surfaces through a microscope. In addition that the decays of metallic elements from metals into crude oil samples were measured and the variations of the initial hardness of metals after the corrosion were measured by Vicker’s hardness tester. Basically there were observed the lower corrosion rates from stainless steels mainly with at least 12% of chromium and sufficient amount of nickel, higher progress of salts on the metallic corrosion at the normal temperatures while comparing with other corrosive compounds, formations of FeS, Fe2O3, corrosion cracks and cavities on the metal surfaces, decay of ferrous and copper from most metals while the immersion into crude oils and small and some insignificantly deductions of the initial hardness of metals.
https://www.chemrevlett.com/article_87897_76d6b92ac9efdc911791a3ae5813a3a1.pdf
2019-02-01
21
32
10.22034/crl.2019.87897
Crude oils
Corrosive composites
Ferrous metals
Decay
weight loss
Suresh
Aluvihara
sureshaluvihare@gmail.com
1
Department of Chemical and Process Engineering, University of Peradeniya, Sri Lanka
LEAD_AUTHOR
Jagath K.
Premachandra
2
Department of Chemical and Process Engineering, University of Moratuwa, Katubedda, Sri Lanka
AUTHOR
[1] O. P. Khana, Materials Science and Metallurgy, New Delhi: Dhanpet Rai and Sons publication, 2009.
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[2] T.A. Alsahhaf, A. Elkilani and M.A. Fahim, Fundamentals of Petroleum Refining, Amsterdam: Radarweg Press, 2010.
2
[3] W. D. Calister, An Introduction of Materials Science and Engineering, NewYork: John Wiley and Sons, Inc, 2003.
3
[4] M.E. Davis and R.J. Davis, Eds., Fundamentals of Chemical Reaction Engineering, New York: McGraw-Hill, 2003.
4
[5] R. Singh, Introduction to Basic Manufacturing Process and Engineering Workshop, New Delhi: New Age International Publication, 2006.
5
[6] W. Bolton, Eds., Engineering Materials Technology, London: B. H Newnes Limited, 1994.
6
[7] H. A. Ajimotokan, A. Y. Badmos and E. O. Emmanuel, Corrosion in Petroleum Pipelines. NY. Sci. J., 2 (2009) 36-40.
7
[8] J.G. Speight, Eds., The Chemistry and Technology of Petroleum, New York: Marcel Dekker, 1999.
8
[9] G. A. Afaf, Corrosion Treatment of High TAN Crude. PhD. Thesis, University of Khartoum, Khartoum, Sudan, 2007.
9
[10] G. C. Okpokwasili and K. O. Oparaodu, Comparison of Percentage Weight Loss and Corrosion Rate Trends in Different Metal Coupons from two Soil Environments. Int. J. Environ. Bioremediat. Biodegrad., 2 (2014) 243-249.
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[11] A.D. Usman and L.N. Okoro, Mild Steel Corrosion in Different Oil Types. Int. J. Sci. Res. Innov. Technol., 2 (2015) 9-13.
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[12] I. M. Ahmed, M. M. Elnour and M. T. Ibrahim, Study the Effects of Naphthenic Acid in Crude Oil Equipment Corrosion, J. Appl. Indust. Sci., 2 (2014) 255-260.
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[13] G. W. Luther and D. Rickard, Chemistry of Iron Sulfides. Chem. Rev., 107 (2007) 514-562.
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[14] H. Fang, S. Nesic, D. Young, Corrosion of Mild Steel in the Presence of Elemental Sulfur Int. Corros. Conference. Expo., (2008).
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[15] G. M. Bota, S. Nesic, D. Qu and H.A. Wolf, Naphthenic Acid Corrosion of Mild Steel in the Presence of Sulfide Scales Formed in Crude Oil Fractions at High Temperature, Int. Corros. Conference. Expo., (2010).
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[17] W.F. Smith, and J. Hashemi, Foundations of Material Science and Engineering, 4th Ed. New York: McGraw-Hill, 2006.
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[18] N. S. Hassan, The Effect of Different Operating Parameters on the Corrosion Rate of Carbon Steel in Petroleum Fractions. Eng. Technol. J., 31A (2013) 1182- 1193.
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[19] M. Schoell, Stable isotopes in petroleum research. In Advances in Petroleum Geochemistry, 1st Ed. J. Brooks and D. Welte. pp. 215-245. London: Academic Press, 1984.
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[21] M. Engel, and S. A. Macko, Organic Geochemistry: Principles and Applications, Plenum Press, NewYork, pp. 861, 1993.
21
ORIGINAL_ARTICLE
Kinetic study of adsorption methylene blue dye from aqueous solutions using activated carbon
In this article efficiency of activated carbon as a potent adsorbent of cationic dyes dyes present in waste water was studied in this research. Activated carbon (AC) from starch was used to adsorb methylene blue (MB) from an aqueous solution. Various parameters such as adsorbent concentration, temperature, initial dye concentration, contact time, and pH were investigated and the optimum parameters were determined based on the experimental outcomes. The extent of methylene blue removal increased with the increased in contact time, adsorbent mass, solution pH and amount of adsorbent used. Thermodynamic parameters like the Gibbs free energy (ΔG°), enthalpy (ΔH°), and entropy (ΔS°) were also determined and they showed that the adsorption process was feasible, spontaneous, and exothermic in the temperature range of 293–333 K. The experimental equilibrium data were analyzed using the isotherms of Langmuir, Freundlich, and Tempkin. Two simplified kinetic models including pseudo-first-order and pseudo-second-order equation were selected to follow the adsorption processes.
https://www.chemrevlett.com/article_87964_d5e18d4ec387268760439ee41f71dbfd.pdf
2019-02-01
33
39
10.22034/crl.2019.87964
Activated carbon
Methylene blue
Starch
Isotherm
Kinetics
Fatima Zahra
Benhachem
f.benhachem@yahoo.com
1
Department of Chemistry, institute of exact sciences, University Center Ahmed Zabana of Relizane. Algeria
AUTHOR
Tarik
Attar
att_tarik@yahoo.fr
2
Superior School of Applied Sciences of Tlemcen, Bel Horizon, Tlemcen, Algeria
LEAD_AUTHOR
Fouzia
Bouabdallah
fouziafifo2@gmail.com
3
Laboratory for the Application of Organic Electrolytes and Polyelectrolytes (LAEPO), Department of Chemistry, Faculty of Science, University of Tlemcen, Algeria
AUTHOR
[1] M. A. Hassaan, A. El Nemr, Health and Environmental Impacts of Dyes: Mini Review, American Journal of Environmental Science and Engineering., 1 (2017) 64-67
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[2] P. S. Kumar, S. Ramalingam, K. Sathishkumar, Removal of methylene blue dye from aqueous solution by activated carbon prepared from cashew nut shell as a new low-cost adsorbent, Korean J. Chem. Eng., 28 (2011)149-155.
2
[3] V. Vadivelan, K.V. Kumar. Equilibrium, kinetics, mechanism, and process design for the sorption of methylene blue onto rice husk, J. Colloid Interface Sci., 286 (2005) 90-100.
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[4] B. H. Hameed, A. T. M. Din, A. L. Ahmad, Adsorption of methylene blue onto bamboo-based activated carbon: kinetics and equilibrium studies, J. Hazard. Mater., 141 (2007) 819–825.
4
[5] S. Dhananasekaran, R. Palanivel, S. Pappu, Adsorption of Methylene Blue, Bromophenol Blue, and Coomassie Brilliant Blue by α-chitin nanoparticles, J. Adv. Res., 7 (2016) 113–124. [6] R. Subramaniam, S. Ponnusamy, Novel adsorbent from agricultural waste (cashew NUT shell) for methylene blue dye removal: Optimization by response surface methodology, Water Resources and Industry., 11, 64-70 (2015).
5
[7] V. KumarGupta, R. Kumar, A. Nayak, T. A.Saleh, M.A.Barakat, Adsorptive removal of dyes from aqueous solution onto carbon nanotubes: A review. Advances in Colloid and Interface Science, 193 (2013) 24-34.
6
[8] M.A. Khan, M.K. Uddin, R. Bushra, Synthesis and characterization of polyaniline Zr(IV) molybdophosphate for the adsorption of phenol from aqueous solution, Reac Kinet Mech Cat., 113 (2014) 499-517
7
[9] R. Ali Khan, S. Ikram, M. Kashif Uddin, Removal of Cr(VI) from aqueous solution on seeds of Artimisia absinthium (novel plant material), Desalination and Water Treatment., 54 (2015) 3358-3371.
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[10] M. Kashif Uddin. A review on the adsorption of heavy metals by clay minerals, with special focus on the past decade, Chemical Engineering Journal., 308 (2017) 438–462.
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[11] Y. D. Sintayehu, L. T. Lencha, Adsorption and Kinetic Optimization Study of Acetic Acid from Aqueous Solutions Using Activated Carbon Developed from Vernonia amygdalinaWood, American Journal of Physical Chemistry.5 (2016) 128-132.
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[12] A. Bhatnagar, W. Hogland, M. Marques, M. Sillanpää, An overview of the modification methods of activated carbon for its water treatment applications, The Chemical Engineering Journal., 219 (2013) 499–511.
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[13] R. Sanghi, B. Bhattacharya Review on decolorization of aqueous dye solutions by low cost adsorbents, Color Technol, 118 (2002) 256-269.
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[14] V. K. Garg, M. Amita, R. Kumar, R. Gupta, Basic dye (methylene blue) removal from simulated wastewater by adsorption using Indian rosewood sawdust: a timber industry waste. Dyes Pigments, 63 (2004) 243-250.
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[15] D. Mohan, A. Sarswat, Y. Sik Ok, C. U. Pittman, Organic and inorganic contaminants removal from water with biochar, a renewable, low cost and sustainable adsorbent – A critical review, Bioresource Technology., 160 (2014) 91–202.
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[16] D. Bergna, T. Varila, H. Romar, U. Lassi, Comparison of the Properties of Activated Carbons Produced in One-Stage and Two-Stage Processes, C, 4 (2018) 41-51.
15
[17] Y. Zhang, J. Zhao, Z. Jiang, D. Shan, Y. Lu, Biosorption of Fe(II) and Mn(II) Ions from Aqueous Solution by Rice Husk Ash, Biomed Res Int., 2014 (2014) 1-10.
16
[18] Rahman, M., Amin, S. M., & Alam, A. M. Removal of Methylene Blue from Waste Water Using Activated Carbon Prepared from Rice Husk, Dhaka University Journal of Science.,60 (2012) 185-189.
17
[19] S. Ghanbarnezhad, L. Sharifi , S. H. Mirhosseini, V. Khani, S. H. Zare, The Influence of Bentonite on the Removal of Methyl Violet Dye, International Journal of Advanced Science and Technology., 70 (2014) 47-54.
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[20] M. A. Rahman, T. Ahmed, I. N. Salehin, M. D. Hossain, Color removal from textile wastewater using date seed activated carbon, Bangladesh J. Sci. Ind. Res., 52 (2017)31-42.
19
[21] Y. Zaker, M. A. Hossain, Effect of Various Factors on the Adsorption of Methylene Blue on Silt Fractionated from Bijoypur Soil, Bangladesh. Int. Res. J. Environment Sci., 2 (2013) 1-7.
20
[22] I. Langmuir, The constitution and fundamental properties of solids and liquids, J. Am. Chem. Soc., 38 (1916) 2221-2295.
21
[23] T. W. Weber, R. K. Chakkravorti, Pore and solid diffusion models for fixedbed adsorbers, AIChE J., 20 (1974)228.
22
[24] K.Y. Foo, Preparation, characterization and evaluation of adsorptive properties of orange peel based activated carbon via microwave induced K2CO3 activation. Bioresour. Technol., 104 (2012) 679-686.
23
[25] P. K. Malik, Use of activated carbons prepared from sawdust and rice-husk for sorption of acid dyes: a case study of acid yellow 36, Dyes Pigm., 56 (2003) 239-249
24
[26] S. Veli, B. Alyüz, Adsorption of copper and zinc from aqueous solutions by using natural clay. Journal of Hazardous Materials., 149 (2007) 226–233.
25
[27] Y. V. S. Sai Krishna, G. Sandhya, R. Ravichandra Babu, Removal of heavy metals Pb(ii), Cd(ii) and Cu(ii) from waste waters using synthesized chromium doped nickel oxide nano particles. Bull. Chem. Soc. Ethiop., 32 (2018) 225-238.
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[28] B. Zhang, F. Li, T. Wu, D. Sun, Y. Li, Adsorption of p-nitrophenol from aqueous solutions using nanographite oxide. Colloids Surf A, Physicochem Eng Asp., 464 (2015) 78–88.
27
[29] L. Andrew, K.Y. Hsieh, Copper-based metal organic framework (MOF), HKUST-1, as an efcient adsorbent to remove p-nitrophenol from water, J Taiwan Inst Chem Eng., 50 (2015) 223–228.
28
ORIGINAL_ARTICLE
Synergetic effect of multi-site phase transfer catalysis system mediated free radical polymerization of acrylonitrile – a kinetic study
In this work, the kinetics and mechanism of free radical polymerization of acrylonitrile (AN) using potassium peroxydisulphate (PDS-K2S2O8) as a water soluble initiator in the presence of synthesized 4,4'-dihexadecyl-1,1'-bipyridine diiumdichloride (DHBPDDC) as multi-site phase-transfer catalyst (MPTC) has been investigated. The polymerization reaction were carried out under nitrogen atmosphere and unstirred condition at constant temperature 60+1°C in ethyl acetate/water biphasic medium. The effects of variation of monomer(AN), initiator(PDS) and catalyst(MPTC) solvent polarity and temperature on the rate of polymerisation (Rp) were ascertained. The order with respect to monomer(acrylonitrile) was found to be unity. The order with respect to initiator and catalyst was found to be 0.51, 0.48 respectively. However, an increase in the polarity of the solvent has slightly increased the rate of polymerization value (Rp). Based on the results obtained, a suitable kinetic mechanism scheme has been proposed to account for the experimental observations and its significance was discussed. The other thermodynamic parameters such as entropy of activation ((∆S#), enthalpy of activation (∆H#) and free energy of activation (∆G#) have been calculated.
https://www.chemrevlett.com/article_88617_9940502a961f1b7c5a1f154656c9fb0f.pdf
2019-02-01
40
47
10.22034/crl.2019.88617
Kinetics
MPTC
Free Radical polymerization
acrylonitrile
K2S2O8
Manickam
Sathiyaraj
manicsathya@gmail.com
1
PG & Research, Department of Chemistry, Pachaiyappa’s College, Chennai, Tamil Nadu, India
LEAD_AUTHOR
Perumal
Venkatesh
pvenkatesh175@gmail.com
2
PG & Research, Department of Chemistry, Pachaiyappa’s College, Chennai, Tamil Nadu, India
LEAD_AUTHOR
Venugopal
Rajendran
1967sssr@gmail.com
3
PG & Department of Chemistry, Pachaiyappa’s College for Men, Kanchipuram, Tamil Nadu, India - 631 501
AUTHOR
[1] Y. Sasson, R. Neumann (Eds.), Handbook of phase transfer catalysis, Blackie Academic & professional, London, 1997.
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[2] M. L. Wang, T. H. Tseng, phase-transfer catalytic reaction of dibromo-o-xylene and 1-butanol in two-phase solution, J. Mol. Catal. A: Chem. 179 (2002) 17-26.
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[3] C. M. Starks, C. L. Liotta, M. Halpern, Phase Transfer Catalysis, Fundamentals, Applications, and Industrial Perspectives, Chapman & Hall, New York, 1994.
3
[4] E. V. Dehmlow, S. S. Dehmlow, Phase Transfer Catalysis, VEB Chemie, Weinheim, Germany, 1983.
4
[5] P. Abimannan, V. Rajendran, Kinetic Study for the Synthesis of 1-nitro-4-(prop-2- ynyloxy) benzene in Solid-Liquid PTC Condition, Curr. Cataly. 5 (2016) 44-50.
5
[6] P. Abimannan, V. Rajendran, Phase transfer catalyzed reaction of disodium salt of 1,3-dihydroxybenzene with propargyl bromide in solid-liquid biphasic condition, Iran. Chem. Comm. 6 (2018) 55-61.
6
[7] M. Sathiyaraj, P.Venkatesh, Synthesis of spiro [cyclobutane-1,2'-indene]-1',3'-dione under a new multi-site phase-transfer catalyst combined with ultrasonication-a kinetic study, Asian. J. Green. Chem. 3 (2019) 53-69.
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[8] M. Brahmayya, M. L. Wang, Kinetic study for benzyloxylation of p-bromotoluene using phase transfer catalyst assisted by microwave irradiation, J. Taiwan. Inst. Chem. Eng. 000 (2016) 1–7
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[9] V. Selvaraj, V. Rajendran, Preparation of 1,3-bis(allyloxy)benzene under a New multi- site phase-transfer catalyst combined with ultrasonication – A kinetic study. Ultrasonics. Sonochem. 20 (2013)1236–1244.
9
[10] E. Murugan, G. Tamizharasu, New soluble multi-site phase transfer catalysts and their catalysis for dichlorocarbene addition to citronellal assisted by ultrasound—A kinetic study, J. Mol. Catal. A: Chem. 363 (2012) 81–89.
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[11] S. Kavitha, V. Rajendran, Polymerization of ethyl methacrylate under the influence of ultrasound assisted a new multi-site phase-transfer catalyst system – A kinetic study. Ultrasonics. Sonochem. 20 (2013) 329-337.
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[12] S. Savitha, M. J. Umapathy, Synthesis of new phase transfer catalyzed free radical polymerization of ethyl methacrylate: A kinetic study, J. App. Poly. Sci. 113 (2009) 637-643.
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[14] H. El-S. Ali, cycloalkylation reaction of fatty amines with a x- di haloalkanes .role of bis-quaternary ammonium salts as phase-transfer catalysts. Catal. Commun. 8 (2007) 855-860.
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[16] K. Harikumar, V. Rajendran, Ultrasound assisted the preparation of 1-butoxy-4-
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nitrobenzene under a new multi-site phase-transfer catalyst – Kinetic study. Ultrason.
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Sonochem. 21(2014) 208 – 215.
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[19] M. Vajjiravel, M. J. Umapathy, Phase transfer catalyst aided radical polymerization of n-butyl acrylate in two-phase system: a kinetic study, Int. J. Ind. Chem. 7 (2016) 441–448.
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[20] E. Murugan, G. Tamizharasu, Synthesis and Characterization of New Soluble Multisite Phase Transfer Catalysts and Their Catalysis in Free Radical Polymerization of Methyl Methacrylate Aided by Ultrasound—A Kinetic Study, J, Appl. Poly. Sci. 125 (2012) 263–273.
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[30] S. Kavitha, V. Rajendran, Polymerization of ethyl methacrylate under the influence of ultrasound assisted a new multi-site phase-transfer catalyst system – A kinetic study. Ultrasonics. Sonochem. 20 (2013) 329-337.
32
[31] M. Vajjiravel, M. J. Umapathy, Synthesis and characterization and application of a multi-site phase transfer catalyst in radical polymerization of n-butyl methacrulate – a kinetic study. J. Polymeric. Mater. 59 (2010) 647-662.
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42