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77-77-0Relevant articles and documents
Synthesis, Characterization, and Identification of New in Vitro Covalent DNA Adducts of Divinyl Sulfone, an Oxidative Metabolite of Sulfur Mustard
Lv, Shanshan,Zhang, Yajiao,Xu, Bin,Xu, Hua,Zhao, Yumei,Chen, Jia,Gao, Zhongcai,Wu, Jianfeng,Xie, Jianwei
, p. 1874 - 1882 (2017)
Divinyl sulfone (DVS) is an important oxidative metabolic product of sulfur mustard (SM) in vitro and in vivo. Although DVS is not a classical blister agent, its high reactivity and toxicity induced by vinyl groups can also cause blisters like SM upon contact with the skin, eyes, and respiratory organs. The purpose of this paper was to identify whether DVS could covalently bind to DNA bases to form new DNA adducts in cells in vitro. A series of adducts were synthesized and characterized using purine, nucleoside, or DNA, separately, as starting materials. The covalent site, pattern, and relative reactivity of adduct formation were identified and discussed in detail. The results showed that five high abundance site-specific DNA adducts, including two monoadducts and three cross-linked adducts, were obtained when DNA was used as a substrate. When HaCaT cells were exposed to 30 μM of DVS, four new DNA adducts containing monoadducts and cross-linked adducts were found and identified in cells, including N3-A monoadduct, N7-G monoadduct, N7G-N7G bis-adduct, and N3A-N7G cross-linked adduct. Among them, the abundance of N3-A monoadduct was 10 times higher than that of the other three adducts. DNA adduct formation with DVS showed significant differences from that observed with SM. The observation of these new DNA adduct in vitro cells revealed that DNA damage could be also induced by DVS.
A convenient synthesis of (E)-conjugated polyene sulfonyl derivatives with excellent stereospecificity
Yu, Chunyan,Lv, Zhongwen,Xu, Sheng,Zhang, Jun
supporting information, p. 3234 - 3237 (2018/07/25)
A highly selective synthesis of conjugated polyene sulfonyl derivatives is described via the elimination of disulfonyl chloride with readily accessible raw material dihaloalkane. The protocol offers a convenient way to form sulfonamides, sulfonates and even sulfones. Furthermore, this method was manipulated under mild condition with simple operation in high yield to afford only trans products.
Study on the Kinetics and Transformation Products of Sulfur Mustard Sulfoxide and Sulfur Mustard Sulfone in Various Reaction Media
Popiel, Stanis?aw,Nawa?a, Jakub,Dziedzic, Daniel,Gordon, Diana,Dawidziuk, Barbara
, p. 75 - 89 (2017/12/29)
Considering postulates of the Chemical Weapons Convention, this article is an attempt to improve the decontamination methods of mustard gas (HD) and studying its products of decontamination. It is widely known that mustard gas sulfoxide (HDO; O═S(CH2CH2Cl)2) and sulfone (HDO2; O2═S(CH2CH2Cl)2) undergo further transformations to another compounds, but so far kinetics of these processes have not yet been investigated neither carefully nor thoroughly. This study is focused on determination of kinetics and mechanisms of transformation of HD oxidation products. The primary objective of this study is to assess the impact of selected factors on the kinetics of the HCl elimination reaction and to determine the conditions in which cyclization reactions of divinyl sulfoxide and sulfone proceed. The HDO and HDO2 decay kinetics were monitored in an aqueous solution of the desired pH. The rate of HCl elimination from HDO and HDO2 is strongly dependent on pH. For example, with pH increasing from 9 to 12 the rate of HCl elimination from HDO increased over 1200 times. In solutions of pH 9, HDO loses hydrogen chloride at approximately 100 times slower compared to HDO2, and the difference is reduced with increasing pH. In pH 12 solutions, the rate of hydrogen chloride loss from HDO2 is only 20 times higher than the HCl loss from HDO. Divinyl sulfoxide and sulfone undergo a further transformation in a strongly alkaline environment, leading to cyclization and formation of 1,4-thioxane sulfoxide and sulfone, respectively. Elimination of HCl from HDO and HDO2 goes with a rapidly increasing rate with increasing pH if alkalinity of the reaction medium is relatively very high (the range of pH 9–12). Furthermore, the conversion of divinyl sulfone and sulfoxide to sulfoxide and sulfone thioxane, respectively, occurs at a measurable rate when the pH of the solution is in the range of 12–14.
Synthesis and characterization of PMoV/Fe3O4/g-C3N4 from melamine: An industrial green nanocatalyst for deep oxidative desulfurization
Rafiee, Ezzat,Khodayari, Maryam
, p. 458 - 468 (2017/04/04)
A facile approach to the preparation of a novel magnetically separable H5PMo10V2O40/Fe3O4/g-C3N4 (PMoV/Fe3O4/g-C3N4) nanocomposite by chemical impregnation is demonstrated. The prepared nanocomposite was characterized and its acidity was measured by potentiometric titration. PMoV/Fe3O4/g-C3N4 showed high catalytic activity in the selective oxidative desulfurization of sulfides to their corresponding sulfoxides or sulfones. The catalytic oxidation of a dibenzothiophene (DBT)-containing model oil and that of real oil were also studied under optimized conditions. In addition, the effects of various nitrogen compounds, as well as the use of one- and two-ring aromatic hydrocarbons as co-solvents, on the catalytic removal of sulfur from DBT were investigated. The catalyst was easily separated and could be recovered from the reaction mixture by using an external magnetic field. Additionally, the remaining reactants could be separated from the products by simple decantation if an appropriate solvent was chosen for the extraction. The advantages of this nanocatalyst are its high catalytic activity and reusability; it can be used at least four times without considerable loss of activity.
Selective oxidation of sulfurs and oxidation desulfurization of model oil by 12-tungstophosphoric acid on cobalt-ferrite nanoparticles as magnetically recoverable catalyst
Rafiee, Ezzat,Rahpeyma, Nasibeh
, p. 1342 - 1349 (2015/09/01)
Silica-coated CoFe2O4 nanoparticles were prepared and used as a support for the immobilization of 12-tungstophosphoric acid, to produce a new magnetically separable catalyst. This catalyst was characterized using X-ray diffraction, wavelength-dispersive X-ray spectroscopy, Fourier-transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, laser particle size analysis, and vibrating sample magnetometry. The catalyst showed high activity in the selective oxidation of thioethers and thiophenes to the corresponding sulfones under mild conditions. The catalytic activity of the nanocatalyst in the oxidative desulfurization of model oil was investigated. The effect of nitrogen-containing compounds on sulfur removal from the model oil was also evaluated. The catalyst showed high activity in the oxidative desulfurization of diesel. The catalyst can be readily isolated from the oxidation system using an external magnet and no obvious loss of activity was observed when the catalyst was reused in four consecutive runs.
Kinetic investigation on the highly efficient and selective oxidation of sulfides to sulfoxides and sulfones with t-BuOOH catalyzed by La2O3
Mandal, Mrinmay,Chakraborty, Debashis
, p. 12111 - 12122 (2015/02/19)
The selective oxidation of various sulfides to sulfoxides by a simple, efficient, and environmentally benign method is of prime focus. In this paper, we have explored a highly efficient protocol for the oxidation of alkyl aryl sulfides to sulfoxides with high selectivities catalyzed by La2O3 in the presence of 70% t-BuOOH solution (water). We obtained predominantly the monooxygenated product. The over oxidation of sulfides to sulfones was not observed under these conditions. The resulting products are obtained in good to excellent yields within a reasonable time without the use of ligands and other additives. The epoxidation of the double bond as well as allylic oxidation are not observed with allyl sulfides. Sulfones can be obtained quantitatively by altering the reaction conditions. The surface morphology and the catalyst reusability were verified by XRD, AFM and SEM techniques. The surface area of the La2O3 was measured using BET isotherms.
Highly selective and efficient oxidation of sulfide to sulfoxide catalyzed by platinum porphyrins
Alemohammad, Tahereh,Rayati, Saeed,Safari, Nasser
, p. 1279 - 1283 (2016/02/18)
Two platinum porphyrins, meso-tetramesitylporphyrinatoplatinum and meso-tetrakis(pentaflourophenyl) porphyrinatoplatinum, are explored for catalytic application in the selective oxidation of sulfide to sulfoxide by iodosylbenzene. The obtained overall turnover number of 90,000 in the oxidation of thioanisole in the presence of meso-tetrakis(pentaflourophenyl) porphyrinatoplatinum indicates the pronounced catalytic activity of the platinum porphyrins. Perfect selectivity toward sulfoxide or sulfone also was achieved via stoichiometric control of reactants.
Selective Oxidation of Sulfides Catalyzed by the Nanocluster Polyoxomolybdate (NH4)12[Mo36(NO)4O108(H2O)16]
Amini, Mojtaba,Naslhajian, Hadi,Farnia, S. Morteza F.,Holyska, Malgorzata
, p. 3873 - 3878 (2015/08/24)
The (NH4)12[Mo36(NO)4O108(H2O)16]·30.84H2O ({Mo36}) catalyst has been synthesized and successfully employed in the selective oxidation of various sulfides to sulfoxides with urea hydrogen peroxide as oxidant under mild reaction conditions with 84-99 % conversion and 58-99 % selectivity, with active functional groups such as the hydroxy group and C=C bonds tolerated in the oxidation. The {Mo36} catalyst showed high catalytic activity for a high substrate/catalyst ratio (up to 30000:1) and is recyclable.
Chemoselective oxidation of sulfides to sulfoxides with urea hydrogen peroxide (UHP) catalyzed by non-, partially and fully β-brominated meso-tetraphenylporphyrinatomanganese(III) acetate
Rayati, Saeed,Nejabat, Fatemeh,Zakavi, Saeed
, p. 82 - 86 (2014/01/06)
Selective oxidation of sulfides to sulfoxides with urea hydrogen peroxide in the presence of the manganese complex of non-, partially and fully brominated meso-tetraphenylporphyrin, (MnTPPBrx(OAc) (x = 0, 2, 4, 6 and 8)) is reported. Although, the maximum conversion was achieved in the case of MnTPPBr4(OAc), little difference was found between the catalytic activity of MnTPP(OAc), MnTPPBr2(OAc) and MnTPPBr4(OAc). MnTPPBr8(OAc) showed an unusually very low catalytic efficiency compared to the other manganese porphyrins. The presence of small amounts of acetic acid was shown to have significant effect on the total conversion and the oxidative stability of the catalyst.
Organic-inorganic polyoxometalate based salts as thermoregulated phase-separable catalysts for selective oxidation of thioethers and thiophenes and deep desulfurization of model fuels
Rafiee, Ezzat,Eavani, Sara
, p. 18 - 27 (2013/10/22)
Synthesis of various organic-inorganic polyoxometalate based salts composed of sulfonated pyridinum cations and the Keggin tungstophosphate anion (PW 12O403-) and their subsequent application in the oxidation of methyl phenyl sulfide with hydrogen peroxide in aqueous media was reported. Special attention was paid to the temperature-dependent solubility of the salts as a function of the organic cation in water. Cyclic voltammetry was further used for the investigation of the redox behavior of these catalysts. Based on these properties, a novel thermoregulated phase-separable catalyst was introduced and successfully used for the selective oxidation of thioethers and thiophenes to the corresponding sulfoxides or sulfones. Catalytic oxidation of the sulfur-containing model oil (methyl phenyl sulfide, dibenzothiophene and thiophene) was also studied under optimized conditions. In both cases, excellent conversion and selectivity were obtained in relatively short reaction times. This novel catalyst showed the characteristic of homogeneous reaction at ambient temperatures and phase-separation at lower temperatures. By simple decantation, the catalyst could be easily separated from the products upon cooling of the reaction mixture and could be reused several times with high recycling efficiency.