Removal Study of Hazardous Thiols Pollution by Tributylammonium Halochromates(VI) / Silica , (C4H9)3NH+[CrO3X]-, (X=F, Cl): as an Oxidizing Agent
محورهای موضوعی : Research paper
1 - Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
کلید واژه: thiol, Disulfide, Heterogeneous oxidants, Silica gel, Halochromates,
چکیده مقاله :
Oxidative coupling of thiols to the corresponding symmetrical disulfides were performed in the presence of silica gel supported tributylammonium fluorochromate(VI), (TriBAFC), and tributylammonium chlorochromate(VI), (TriBACC). Silica gel supported TriBAFC and TriBACC are versatile reagents for the effective and selective oxidation of organic substrates, in particular of thiol, under mild conditions. Disulfides are also key intermediates in a wide variety of organic synthetic routes .Considerable improvements are observed in the presence of the absorbent and making the work-up much more convenient. The nature of the solvent does not appear to be particularly critical. Hydrocarbons, benzene, ethers and chlorinated hydrocarbons are equally effective, the practical choice being oriented by the solubility of the products and the desired reaction temperature. The IR spectra of TriBAFC and TriBACC are similar to that of other fluoro and chlorochromates, TriBAFC and TriBACC are soluble in water, dimethylformamide, acetonitrile, acetone and dichloromethane; they are only sparingly soluble in benzene, carbon tetrachloride, chloroform and hexane.
Abbaspour, M., Javid, A. H., Jalilzadeh Yengjeh, R., Hassani, A. H., & Mostafavi, P. G. (2013). The biodegradation of methyl tert-butyl ether (MTBE) by indigenous Bacillus cereus strain RJ1 isolated from soil. Petroleum Science and Technology, 31(18), 1835-1841.
Ahari, S. M., Yangejeh, R. J., Mahvic, A. H., Shahamat, Y. D., & Takdastan, A. (2019). A new method for the removal of ammonium from drinking water using hybrid method of modified zeolites/catalytic ozonation. Desalin Water Treat, 170, 148-57.
Alishiri, A., Fataei, E., & Ranjbar Baranloo, H. (2020). The effects of nutrients and folic acid on the biological treatment of petrochemical wastewater. Journal of Advances in Environmental health research, 8(3), 201-209.
Ashutosh V J , Bhusare S , Baidossi M, Qafisheh N , Sasson Y, (2005) Oxidative coupling of thiols to disulfides using a solid anhydrous potassium phosphate catalyst. Tetrahedron Lett, 46(20): 3583-3585
Attri P, Gupta S, Kumar R,(2012) Green methodology for the preparation of disulfide. Green Chem Lett and Rev, 5(1): 33-42.
Babaei, A. A., Ghanbari, F., & Yengejeh, R. J. (2017). Simultaneous use of iron and copper anodes in photoelectro-Fenton process: concurrent removals of dye and cadmium. Water science and technology, 75(7), 1732-1742.
Bayati, F., Mohammadi, M. K., Yengejeh, R. J., & Babaei, A. A. (2021). Ag 2 O/GO/TiO 2 composite nanoparticles: synthesis, characterization, and optical studies. Journal of the Australian Ceramic Society, 57, 287-293.
Beidaghdar, M., Fataei, E., Khanizadeh, B., & Imani, A. A. (2022). Feasibility study of using UV/H2O2/O3 advanced oxidation in phenol removal from petrochemical wastewater. Journal of Applied Research in Water and Wastewater, 9(1), 40-45.
Capozzi G, Modena S,(1974) The Chemistry of the thiol Group, Wiley, New York, . p.785.
Elmi, R., Farshi, A., Nejaei, A., Ramazani, M. E., & Alaie, E. (2021). Treatment of spent caustic effluent of oil refinery with catalytic oxidation and optimization of relevant parameters using response surface methodology. Anthropogenic Pollution, 5(1), 112-127.
Farjam, M. H., Mohammadi, M. K., & Mehraki, A. (2014). Adsorption evaluation of food and industrial dyes on nano copper oxide. Journal of Chemical Reactivity and Synthesis, 4(1), 31-44.
Farsani, M. H., Yengejeh, R. J., Mirzahosseini, A. H., Monavari, M., Hassani, A. H., & Mengelizadeh, N. (2022). Effective leachate treatment by a pilot-scale submerged electro-membrane bioreactor. Environmental science and pollution research, 1-14.
Fekri, R., Mirbagheri, S. A., Fataei, E., Ebrahimzadeh-Rajaei, G., & Taghavi, L. (2021). Organic compound removal from textile wastewater by photocatalytic and sonocatalytic processes in the presence of copper oxide nanoparticles. Anthropogenic Pollution, 5(2), 93-103.
Fieser LF, Fieser M ,(1967-84) Reagents for Organic Synthesis, 1-11,Wiley, New York.
Firouzabadi H, Iranpoor N, Gorginpour F, Samadi A. (2015) Dithiooxamide as an effective sulfur surrogate for odorless high-yielding carbon-sulfur bond formation in Wet PEG200 as an eco-friendly, safe, and recoverable solvent. Eur. J. Org. Chem, 13: 2914-2920
Gashtasbi, F., Yengejeh, R. J., & Babaei, A. A. (2017). Adsorption of vancomycin antibiotic from aqueous solution using an activated carbon impregnated magnetite composite. Desalination and water treatment, 88, 286-297.
Ghammami S, Tajbakhsh M. (2005) Oxidative coupling of thiols to disulfides in solution and under microwave radiation with tripropylammonium chlorochromate.
J Sulf Chem , 26 ( 2): 145-153.
Ghammamy Sh, Eimanieh H, Mohammady M K. (2007) Cetyltrimethylammonium Bromochromate: A New and Efficient Oxidant for Organic Substrates . Synth Commun, 37: 601–607.
Ghammamy Sh, Mohammadi M K, Hassani Joshaghani A. (2008) Triethylamonium Halochromates /Silica gel: An Efficient Reagent For Oxidative Coupling of Thiols to Disulfides . Maced J Chem Chemi Eng, 27( 2) 117–122 .
Heidari Farsani, M., Jalilzadeh Yengejeh, R., Hajiseyed Mirzahosseini, A., Monavari, M., Hassani, A. H., & Mengelizadeh, N. (2021). Study of the performance of bench-scale electro-membranes bioreactor in leachate treatment. Advances in Environmental Technology, 7(3), 209-220.
Holbrook DL, (1996) Handbook of Petroleum Refining Processes, Chap. 11.3, R.A. Meyers (Ed.), McGraw Hill.
Hosseinpoor F, Golchoubian H.(2006) Mild and highly efficient transformation of thiols to symmetrical disulfides using urea–hydrogen peroxide catalyzed by a Mn(III)–salen complex. Catalysis Lett, 111( 3–4) :235-247.
Jalalzadeh, A., Rabieifar, H. R., Vosoughifar, H., Razmkhah, A., & Fataei, E. (2022). Investigation of daily waste load allocation in Zarrineh-rud river for environmental management of cold-water fish species. Anthropogenic Pollution, 6(1), 36-46.
Jalilzadeh Yengejeh, R., Pourjafarian, V., Afrous, A., Gholami, A., Maktabi, P., & Sharifi, R. (2017). Studying Bacillus cereus's ability to biodegrade crude oil in hot areas. Petroleum Science and Technology, 35(3), 287-291.
Jalilzadeh, Y. R., Sekhavatjou, M. S., Maktabi, P., ARBAB, S. N., Khadivi, S., & Pourjafarian, V. (2014). The biodegradation of crude oil by Bacillus subtilis isolated from contaminated soil in hot weather areas.
Jocelyn DC, (1992), Biochemistry of the Thiol Group. p. 1, Academic Press, New York.
Karbul, A., Mohammadi, M. K., Yengejeh, R. J., & Farrokhian, F. (2021). Synthesis and characterization of trimetallic Fe-Co-V/zeolite and Fe-Co-Mo/zeolite composite nanostructures. Materials Research, 24.
Karimipour, Z., Jalilzadeh Yengejeh, R., Haghighatzadeh, A., Mohammadi, M. K., & Mohammadi Rouzbehani, M. (2021). UV-Induced Photodegradation of 2, 4, 6-Trichlorophenol Using Ag–Fe 2 O 3–CeO 2 Photocatalysts. Journal of Inorganic and Organometallic Polymers and Materials, 31, 1143-1152.
Khajeh Hoseini, L., Jalilzadeh Yengejeh, R., Mohammadi Rouzbehani, M., & Sabzalipour, S. (2022). Health risk assessment of volatile organic compounds (VOCs) in a refinery in the southwest of Iran using SQRA method. Frontiers in Public Health, 10, 978354.
Khayatnezhad, M. & nasehi, F. (2021). Industrial pesticides and a methods assessment for the reduction of associated risks: a Review. Advancements in Life Sciences, 8, 202-210.
Kordestani, B., Takdastan, A., Jalilzadeh Yengejeh, R., & Neisi, A. K. (2020). Photo-Fenton oxidative of pharmaceutical wastewater containing meropenem and ceftriaxone antibiotics: influential factors, feasibility, and biodegradability studies. Toxin reviews, 39(3), 292-302.
Kumar V, Kaushik M P. (2008) Efficient Oxidative Coupling of Thiols into Disulfides Using N-tert-Butyl-N-chlorocyanamide. Bull. Chem. Soc. Jpn,81( 1)160–162.
Lam J, Bildose H, ChristenseLP n, Thomsen T, (1989) Chemical Constituents of Santolina chamaecyparissus. Acta Chem Scand Ser B, 43: 799-802 .
Leitao A, Costa C, Rodrigues A, (1987) Studies on the impregnation step of the Merox process. Chem. Eng. Sci , 42,1987 ( 2291-2299).
Liting Y, Shuding Li, Yingchao D, Shan Z, Heng L, Panke Z, Bingxin Y, (2017) Pr TEMPO-Catalyzed Aerobic Oxidative Coupling of Thiols for Metal-Free Formation of S−N/S−S Bonds. Asian j of org chem, 6(3): 265-268.
Masoumi, A., & Yengejeh, R. J. (2020). Study of chemical wastes in the Iranian petroleum industry and feasibility of hazardous waste disposal. Journal of Environmental Health Science and Engineering, 18(2), 1037-1044.
Mehrdoost, A., Yengejeh, R. J., Mohammadi, M. K., Haghighatzadeh, A., & Babaei, A. A. (2022). Adsorption removal and photocatalytic degradation of azithromycin from aqueous solution using PAC/Fe/Ag/Zn nanocomposite. Environmental Science and Pollution Research, 29(22), 33514-33527.
Nikpour, B., Jalilzadeh Yengejeh, R., Takdastan, A., Hassani, A. H., & Zazouli, M. A. (2020). The investigation of biological removal of nitrogen and phosphorous from domestic wastewater by inserting anaerobic/anoxic holding tank in the return sludge line of MLE-OSA modified system. Journal of environmental health science and engineering, 18, 1-10.
Nouri Dodaran, P., Fataei, E., & Khanizadeh, B. (2019). Study on photocatalytic and sonocatalytic activity of Bi2O3 synthesized by Sol-gel method in removing organic compounds of ardabil textile factory effluents. Journal of Water and Wastewater; Ab va Fazilab (in persian), 30(4), 67-77.
Oka M, Kozako R, Iida H,(2021) combination of a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions at room temperature. The the biomimetic flavin catalyst enables the transfer of electrons from the iodine forming the basis for a green oxidative synthesis of disulfides from thiols. Synlett, 32: 1227-1230.
Olivier, H. ., Emmanuel, U. ., & Gloria, H. . (2023). Weather influence on the performance of solar collector . International Journal of Sustainable Energy and Environmental Research, 12(1), 10–16. https://doi.org/10.18488/13.v12i1.3379
Orooji, N., Takdastan, A., Jalilzadeh Yengejeh, R., Jorfi, S., & Davami, A. H. (2022). Monitoring of 2, 4-dichlorophenoxyacetic acid concentration in Karun River and effluents of water treatment plants. Toxin Reviews, 41(3), 785-794.
Pillai, R. R., & Thomas, V. (2023). Plasma Surface Engineering of Natural and Sustainable Polymeric Derivatives and Their Potential Applications. Polymers, 15(2), 400.
Sadeghi, B., Shafaghatian, N., Alayi, R., El Haj Assad, M., Zishan, F., & Hosseinzadeh, H. (2022). Optimization of synchronized frequency and voltage control for a distributed generation system using the Black Widow Optimization algorithm. Clean Energy, 6(1), 105-118.
Sekhavati, E., & Yengejeh, R. J. (2021). Assessment optimization of safety and health risks using fuzzy TOPSIS technique (case study: construction sites in the South of Iran). Journal of Environmental Health and Sustainable Development.
Shokri, R., Yengejeh, R. J., Babaei, A. A., Derikvand, E., & Almasi, A. (2019). UV activation of hydrogen peroxide for removal of azithromycin antibiotic from aqueous solution: determination of optimum conditions by response surface methodology. Toxin Reviews.
Soleiman-Beigi M, Arzehgar Z. (2018) The reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 provides O-Ethyl-S-aryl carbonodithioates as intermediates, that can be converted into symmetrical diaryl disulfides, unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S-alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides. Synlett, 29: 986-992.
Sun, Q., Wang, L., Li, Y., Li, L., Li, S., & Zhu, G. (2023). Highly Efficient Removal of Mercury Ions from Aqueous Solutions by Thiol-Functionalized Graphene Oxide. Water, 15(14), 2529.
Tabari, M. R. R., Sabzalipour, S., Peyghambarzadeh, S. M., & Jalilzadeh, R. (2021). DISPERSION OF VOLATILE ORGANIC COMPOUNDS IN THE VICINITY OF PETROLEUM PRODUCTS STORAGE TANKS. Environmental Engineering & Management Journal (EEMJ), 20(7).
Talaei, Y., Micula, S., Hosseinzadeh, H., & Noeiaghdam, S. (2022). A novel algorithm to solve nonlinear fractional quadratic integral equations. AIMS Mathematics, 7(7), 13237-13257. doi:10.3934/math.2022730
Talla A, Driessen B, Straathof N J W, Milroy L G, Brunsveld L, Hessel V, Noël T. (2015) Metal-free photocatalytic aerobic oxidation of thiols to disulfides in batch and continuous-flow. Adv. Synth. Catal, 357: 2180- 2186.
Wang, S., Ma, J., Li, W., Khayatnezhad, M. & Rouyendegh, B. D. (2022). An optimal configuration for hybrid SOFC, gas turbine, and Proton Exchange Membrane Electrolyzer using a developed Aquila Optimizer. International Journal of Hydrogen Energy, 47, 8943-8955.
Yousefi, M., Rahmani, K., Jalilzadeh Yengejeh, R., & Goudarzi, G. (2021). Green synthesis of zero iron nanoparticles and its application in the degradation of Sulphacetamide by using of PS/nZVI process. International Journal of Environmental Analytical Chemistry, 1-14.
Yu-Jian H, Li Y, Zhao Z W, Fan T G, Sun B X, Wang X N , Li Y M. (2023) Oxidative Dehydrogenative Coupling of Thiols with Alkanes for the Synthesis of Sulfoxides, Org Lett, 25(3): 517-521
Zeinizadeh B,(2002) Oxidative Coupling of Thiols to Disulfides with Iodine in Wet Acetonitrile. J chem res: 564-566
Zeinizadeh B,Iranpoor N (2003) Oxidative Coupling of Thiols to Disulfides with Ti(IV) in the Presence of NaI under Air Atmosphere. J Chin chem soc, 50(4): 849-852.