- Sulfonylbis(acylhydrazones) as anticholinesterase inhibitors: Synthesis, in vitro biological evaluation and computational studies
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This current research work is focused on the synthesis of sulfonyl-mediated hydrazones, its exploration as anticholinesterase inhibitors, in vitro biological evaluation, and computational studies. A series of 21 novel bis(acylhydrazones) (4a-u) have been synthesized in good to excellent yields using 4,4?-sulfonyldiphenol as the precursor. Characterization of the synthesized compounds was achieved via spectroscopic techniques i.e. UV, FT-IR, NMR (1H and 13C), and HRMS. In vitro anticholinesterase activity of these compounds was performed using acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) as cholinesterase enzymes. Among all the compounds tested, compounds 4 g and 4 h were found to be the most significant AChE inhibitions with IC50 values of 101.4 and 102.7 μM as compared to the standard cholinesterase inhibitor i.e., galantamine (IC50 = 104.5 μM). Additionally, compound 4 g was also found to be an excellent inhibitor of BChE with an IC50 value of 136.0 μM as compared to the standard galantamine (IC50 = 156.8 μM). Molecular docking of the most active compounds 4 g and 4 h also supported their potential to interact with cholinesterase enzymes. Further affirmation on the intermolecular stability of the docked complexes was achieved by molecular dynamics simulation for 100 ns with mean deviations ~2 ?. Residue level fluctuations analysis also interpreted the good stability of compounds interacting pocket residues. Lastly, binding free energy analysis was performed that decipher the intermolecular interactions that are dominated by both van der Waals and electrostatic energies. In short, both theoretical and experimental studies unveiled the compounds as potent blockers of cholinesterase enzymes.
- Ahmad, Manzoor,Ahmad, Sajjad,Akbar, Nazia,Al-Harrasi, Ahmed,Ali, Akbar,Ali, Mumtaz,Ibrahim, Muhamad,Khan, Ajmal,Latif, Abdul,Saadiq, Mohammad,Siddique, Abu Bakar,farooq, Umar
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- One-step hydroxylation of aryl and heteroaryl fluorides using mechanochemistry
-
Simple use of KOH allows the direct F to OH exchange of aromatic and heteroaromatic substrates under mechanochemical conditions. The reaction is performed in the absence of solvent with potassium hydroxide as OH source. As a result, this approach is both more atom economical and environmentally friendly than previously described methods for this transformation.
- Braje, Wilfried,Geneste, Hervé,Rodrigo, Eduardo,Walter, Magnus W.,Wiechert, Rainer
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supporting information
p. 1469 - 1473
(2022/03/07)
-
- Selective synthesis of sulfoxides and sulfonesviacontrollable oxidation of sulfides withN-fluorobenzenesulfonimide
-
A practical and mild method for the switchable synthesis of sulfoxides or sulfonesviaselective oxidation of sulfides using cheapN-fluorobenzenesulfonimide (NFSI) as the oxidant has been developed. These highly chemoselective transformations were simply achieved by varying the NFSI loading with H2O as the green solvent and oxygen source without any additives. The good functional group tolerance makes the strategy valuable.
- Cao, Zhong-Yan,Li, Xiaolong,Lu, Hao,Wang, Panpan,Wang, Shengqiang,Xu, Xiaobo,Yan, Leyu,Yang, A-Xiu
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supporting information
p. 8691 - 8695
(2021/10/22)
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- Macrocyclic sulfone derivatives: Synthesis, characterization, in vitro biological evaluation and molecular docking
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An artificial series of macrocycles based on 4,4′-sulfonyldiphenol intermediate was synthesized using a multistep procedure involving oxidation of bisphenol sulfide, etherification of phenolic hydroxyl groups, and final ring closure with different diamines. Different chemical species having aromatic, heteroaromatic, and aliphatic characters were incorporated into macrocyclic frameworks in the final step of ring closure. This simple and easily executable synthetic strategy was applied to synthesize 15 macrocycles (5a-o) in excellent yields. Characterization of the synthesized products was achieved through well-known modern spectroscopic techniques such as IR, NMR, and Mass. Macrocycles 5m and 5n were found to show significant AChE inhibition with IC50 values of 76.9 ± 0.24 and 71.2 ± 0.77 μM, respectively. Macrocycle 5n was also found to be an active inhibitor of butyrylcholinesterase (BChE) with IC50 score of 55.3 ± 0.54 μM. Among others, macrocycle 5l cyclized with o-phenylenediamine demonstrated moderate inhibition with IC50 value of 81.1 ± 0.54 μM. Increasing interest in studying interactions of macrocycles with different enzymatic targets compelled us to design and synthesize sulfone-based macrocycles that might prove as highly potent class of biologically active compounds.
- Ibrahim, Muhammad,Latif, Abdul,Ammara,Ali, Akbar,Ribeiro, Alany Ingrid,Farooq, Umar,Ullah, Farhat,Khan, Ajmal,Al-Harrasi, Ahmed,Ahmad, Manzoor,Ali, Mumtaz
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p. 562 - 574
(2020/12/25)
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- Preparation process of low-cost and environment-friendly bisphenol S
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The invention discloses a preparation process of bisphenol S with low cost and environmental protection. When the corrosion-resistant paint is sprayed into the interior of the reaction kettle, N atoms and O atoms of the reinforcing filler can interact with the metal ions to form a chelate. The acid resistance of the reaction kettle is higher, and the preparation cost is further reduced.
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-
Paragraph 0034-0038; 0046-0050; 0058-0062
(2021/11/26)
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- Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
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A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
- Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
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p. 2447 - 2458
(2020/04/15)
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- A biradical oxo-molybdenum complex containing semiquinone and: o -aminophenol benzoxazole-based ligands
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We report a new mononuclear molybdenum(iv) complex, MoOLBISLSQ, in which LSQ (2,4-di-tert-butyl o-semibenzoquinone ligand) has been prepared from the reaction of the o-iminosemibenzoquinone form of a tridentate non-innocent benzoxazole ligand, LBIS, and MoO2(acac)2. The complex was characterized by X-ray crystallography, elemental analysis, IR and UV-vis spectroscopy and magnetic susceptibility measurements. The crystal structure of MoOLBISLSQ revealed a distorted octahedral geometry around the metal centre, surrounded by one O and two N atoms of LBIS and two O atoms of LSQ. The effective magnetic moment (μeff) of MoOLBISLSQ decreased from 2.36 to 0.2 μB in the temperature range of 290 to 2 K, indicating a singlet ground state caused by antiferromagnetic coupling between the metal and ligand centred unpaired electrons. Also, the latter led to the EPR silence of the complex. Cyclic voltammetry (CV) studies indicate both ligand and metal-centered redox processes. MoOLBISLSQ was applied as a catalyst for the oxidative cleavage of cyclohexene to adipic acid and selective oxidation of sulfides to sulfones with aqueous hydrogen peroxide. This journal is
- Galindo, Agustín,Jagli?i?, Zvonko,Masoumpour, Marzieh Sadat,Nasibipour, Mina,Safaei, Elham,Wojtczak, Andrzej
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p. 40853 - 40866
(2020/11/23)
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- Sulfoxidation inside a hypercrosslinked microporous network nanotube catalyst
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In the present work, a kind of efficient heterogeneous catalyst was synthesized from amine-functionalized hypercrosslinked bottlebrush copolymers of microporous network nanotubes (amine-MNNs) and Na2WO4. The synthesized tungstate-supported microporous network nanotubes (TMNNs) catalyst was shown to be highly active in the selective H2O2 oxidation of sulfides to sulfoxides or sulfones under mild conditions due to the high specific surface area (800 m2 g-1) and firm structure of the nanotubes. The catalyst was found to be very stable and could be recycled at least 8 times without any significant loss of activity. These results present a new opportunity for the development of efficient green organic catalytic materials with high activity.
- Shi, Zhaocheng,Ying, Zhong,Yang, Liusai,Meng, Xiaoyan,Wu, Lidan,Yu, Leshu,Huang, Sen,Xiong, Linfeng
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supporting information
p. 1542 - 1547
(2020/02/06)
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- Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
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A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
- Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
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p. 3048 - 3055
(2019/03/21)
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- Palladium-catalyzed one-step synthesis of symmetrical diaryl sulfones from aryl halides and a sulfur dioxide surrogate
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A convenient method for the one-step synthesis of symmetrical diaryl sulfones from aryl halides has been developed. A keystone of the method is the use of K2S2O5, which can be easily and safely handled, as a sulfur dioxide surrogate. The palladium catalyst bearing P(t-Bu)3 as a ligand enables formation of the desired sulfones without significant formation of byproducts.
- Tanaka, Hiromichi,Konishi, Hideyuki,Manabe, Kei
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supporting information
p. 760 - 763
(2019/08/02)
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- Efficient molybdenum catalyzed chemoselective, solvent-free oxidation of sulfides to sulfones at room temperature
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An effcient and reusable molybdenum-based catalyst has been prepared by tethering dioxomolybdenumacetylacetonate complex, MoO2(acac)2, via postsynthesis modifcation of zeolite beta. The catalyst has been characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), scanning electron microscopy-energy dispersive X-ray analysis (SEM-EDX) and inductively coupled plasma (ICP). The catalyst exhibited very high activity for the selective oxidation of sulfdes to sulfones at room temperature. The catalyst can be recycled and reused four times without signifcant loss of activity.
- Hadigavabar, Ali Dadashi,Tabatabaeian, Khalil,Zanjanchi, Mohammad Ali,Mamaghani, Manouchehr
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p. 3829 - 3833
(2018/05/24)
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- Schiff base complex of Mo supported on iron oxide magnetic nanoparticles (Fe3O4) as recoverable nanocatalyst for the selective oxidation of sulfides
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In this work, a new tridentate Schiff base dioxo-molybdenum(VI) complex immobilized on silica-coated magnetic nanoparticles (MoO25CML–Fe3O4@SiO2) has been synthesized and characterized using different techniques such as FTIR, TGA, AAS, ICP–AES, XRD, VSM, EDX and SEM analyses. The catalytic activity of synthesized complex was examined in the oxidation of various sulfides in the presence of H2O2 as cheap, green and eco-friendly oxidant. This catalytic system provides high conversion and selectivity toward either sulfoxides or sulfones under different conditions. Also, the nanocatalyst could be easily separated and regenerated from reaction media by external magnet and could be reused for ten times without significant loss of the activity and selectivity.
- Aghajani, Milad,Monadi, Niaz
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p. 963 - 975
(2017/03/11)
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- Synthesis of bisphenol S dehydration control method
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The invention discloses a dehydration control method for synthesis of bisphenol S, which is implemented by calculating a theoretical amount of dehydrated water according to a synthetic reaction equation of the bisphenol S and the feeding molar ratio of phenols and sulfuric acid; and controlling the early stage of the reaction to be in a rapid dehydration state and the late stage of the reaction to be in a slow dehydration state, wherein preferably, in one third of the dehydration process, 75-85% of water is dehydrated, and in the rest two thirds of the dehydration process, 25-15% of water is further dehydrated. The purity of the bisphenol S after being refined is 99.5% or over, and the chromaticity is less than 20 (platinum-cobalt colorimetric method). By controlling the dehydration speed in the process of bisphenol S synthesis, the excessive oxidation of phenols and phenolsulfonic acid can be avoided, and the purity of bisphenol S in a crude product can be improved. A synthetic bisphenol S crude-product is shallow in appearance color and low in chromaticity; and the purity of the bisphenol S crude-product is relatively high, so that the bisphenol S crude-product is easily further decolored, refined and purified.
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Paragraph 0024-0027; 0028-0031; 0032-0035
(2017/08/25)
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- Thermal recording material
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A thermal recording material having both of excellent coloring property and storage stability with a low cost is provided. The thermal recording material contains a leuco dye and a developer in a coloring layer, and the developer contains 2,4′-dihydroxydiphenylsulfone and 4,4′-dihydroxydiphenylsulfone with a specific ratio, and the above-mentioned two kinds of the dihydroxydiphenylsulfones are made a material obtained by sequentially undergoing a separating step for heightening the weight ratio of a 2,4′ material from a dichlorodiphenylsulfone mixture containing the 2,4′ material and a 4,4′ material, a reaction step of hydrolyzing the mixture to obtain a dihydroxydiphenylsulfone mixture, and a post-treatment step of subjecting to decolorization and purification.
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Page/Page column 18
(2016/09/26)
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- (METH)ACRYLATE COMPOUND, OPTICAL COMPOSITION, MOLDED ARTICLE, AND OPTICAL ELEMENT
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An optical element including a molded article is provided, the molded article being prepared by molding a polymer prepared by polymerizing a (meth)acrylate compound represented at least by the following general formula (1): wherein a and b are each an integer of 1 or 2; X and Y are each —S— or —O—; R1 and R2 are each an alkyl group having 1 or 2 carbon atoms or a hydrogen atom; and Z1 and Z2 are each an alkyl group having 1 or 2 carbon atoms, having a substituent and represented by the following general formula (2): wherein m is selected from 0 and 1; W is a hydrogen atom or a methyl group; and V is selected from substituents represented by the following: *—O—CnH2n—O—**; *—S—CnH2n—S—**; and *—S—CnH2n—O—**, wherein * represents a bond with an alkyl group; ** represents a bond with a (meth)acryloyl group; n is selected from 2, 3 and 4; and at least one hydrogen atom of —CnH2n— is replaced by a methyl group.
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Page/Page column
(2015/07/02)
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- Method of increasing chlorine fastness
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The present invention relates to a method of increasing the chlorine fastness of dyed synthetic polyamide fiber materials, which comprises treating the fiber material after dyeing with an aqueous liquor comprising a thiourea/formaldehyde/bisphenol condensate or a thiourea/polyisocyanate adduct.
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Page/Page column
(2015/02/25)
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- Selective synthesis of sulfoxides and sulfones from sulfides using silica bromide as the heterogeneous promoter and hydrogen peroxide as the terminal oxidant
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Silica bromide as a heterogeneous promoter and reagent is prepared from the reaction of silica gel with PBr3as a non-hydroscopic, filterable, cheap, and stable yellowish powder that can be stored for months. The results show that silica bromide is a suitable and efficient promoter for the chemoselective oxidation of sulfides to the corresponding sulfoxides or sulfones in the presence of 30% H2O2in acetonitrile. The excellent yields, heterogeneous conditions, simplicity, compatibility with a variety of functionalities, and ease of isolation of the products make our procedure a practical alternative.
- Maleki, Behrooz,Hemmati, Saba,Sedrpoushan, Alireza,Ashrafi, Samaneh Sedigh,Veisi, Hojat
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p. 40505 - 40510
(2015/02/03)
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- Liquid-crystal aromatic polyesters containing azo and sulfone units
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Two novel aromatic polyesters containing azo and sulfone units were synthesized by poly-condensation of 4,4′-azobenzene-dicarbonyl chloride with dihydroxydiphenyl sulfones at low temperature. The synthesized polymers exhibited good solubility, inherent viscosity (reaches 1.05 dL g-1), high glass transition temperature (above 200 °C) and thermal stability (≤ 5 % weight loss at 348 °C), which were characterized by Fourier transform infrared spectroscopy. The liquid crystalline and photoisomerization properties were observed by polarizing optical microscope and an ultraviolet-visible spectrophotometer.
- Qiu, Ming Yan,Niu, Yong Sheng,Yu, You Zhu,Guo, Yu Hua
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p. 7759 - 7762
(2015/02/02)
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- Selectivity adjustment of SBA-15 based tungstate catalyst in oxidation of sulfides by incorporating a hydrophobic organic group inside the mesochannels
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A novel heterogeneous catalyst system comprising tungstate ions embedded into the hydrophobic mesochannels of SBA-15 was found to exhibit significant selectivity enhancement in oxidation of sulfides in water or water/CH 3CN using 30% H2O2. Our studies demonstrated that the presence of an n-octyl group in the interior of nanospaces of our catalyst system provides a hydrophobic/hydrophilic region in the mesochannels of the catalyst where the active tungstate species are located and in turn results in at least three distinct important features. First of all, the catalyst comprising the n-octyl group shows much better water tolerance than the catalysts not having hydrophobic organic moieties. Moreover, the nonproductive decomposition of H2O2 was significantly inhibited in the present catalyst system. The present catalyst system also offers an unprecedented selectivity changeover depending on the hydrophobic nature of the initial sulfides and/or the utilized solvent mixture. While high yields and excellent selectivities toward the corresponding sulfoxide were obtained in the oxidation of less hydrophobic sulfides in H2O as a reaction solvent, the selectivity pattern was shifted toward sulfones in the case of using more hydrophobic sulfides as substrates. On the other hand, in CH3CN/ H2O (1:1) as the reaction solvent, almost all of the studied sulfides were selectively oxidized to the corresponding sulfoxide in high yields. On the basis of several compelling observations, we have proposed a synergistic model to explain the origin of the observed selectivities. The catalyst was respectively recovered and reused in five and seven successive reaction runs in water and water/CH3CN, respectively, with only a slight decrease of reactivity.
- Karimi, Babak,Khorasani, Mojtaba
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p. 1657 - 1664
(2013/07/26)
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- Immobilization of MoO2Cl2 on polystyrene via different linkers and oxidation of sulfides in the presence of hydrogen peroxide
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Chloromethylated polystyrene was oxidized to aldehydic polystyrene and by reaction of this aldehydic polystyrene resin with furfuryl amine and 2-(amino methyl) pyridine, imine-bounded polystyrene resins 1a and 1b were obtained. Amine-bounded polystyrene resins 1c-1f were also prepared by direct reaction of chloromethylated polystyrene and amines. These functionalized polystyrene resins were used to immobilize MoO2Cl2 on polystyrene. These functionalized polystyrene resins were characterized with elemental analysis (CHN) and FT-IR spectrum. Polymersupported catalysts were characterized with FT-IR and neutron activation analysis (NAA). These catalysts were used in oxidation of methyl phenyl sulfide in the presence of H2O2 as oxidant and the results showed that these catalysts were highly active and selective. The reusability of these heterogeneous catalysts was also investigated and the results showed that the supported MoO2Cl 2 catalyst on polystyrene via imidazole liker was highly reusable as it was used 15 times in oxidation of methyl phenyl sulfide in the presence of environmental benign oxidant (H2O2) and solvent (H 2O) without any decrease in its activity. Then the catalytic activity of these supported catalysts was investigated in oxidation of some aliphatic and aromatic sulfides. Almost all of these supported molybdenum-based catalysts were highly active and selective in the conversion of these sulfides to their corresponding sulfoxides.
- Grivani,Gholampoor
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experimental part
p. 349 - 355
(2012/08/14)
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- PROCESS FOR THE PRODUCTION OF A SULFONE MONOMER
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The present invention provides an economic and environmentally friendly method for the preparation of polymer grade 4,4'-dichlorodiphenyl sulfone which is substantially free of 2,4' and 3,4'-isomers of dichlorodiphenyl sulfone with yield of over 90%, with substantially reduced reaction times without the use of impregnated catalysts. Further no toxic byproducts such as dimethyl pyrosulfate are formed thereby reducing the load on effluent treatment with the added advantage of substantially recycling the reactants and byproducts. Further the present invention discloses a process is disclosed in which isomeric mixture of 4,4'-, 3,4'-, and 2,4'-dichlorodiphenyl sulfone produced during the preparation of 4,4'-dichlorodiphenyl sulfone is converted to value added products such as diphenyl sulfone, 2,4'- dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfone and 2-aminodiphenyl sulfone.
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Page/Page column 36
(2011/06/25)
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- COLOR DEVELOPING COMPOSITION CONTAINING MOLECULAR COMPOUND, AND RECORDING MATERIAL
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Provided is a color-developing composition containing a molecular compound which has as a component compound a compound represented by formula (I) [wherein Y represents a C1-C12 hydrocarbon group which is chained or branched and saturated or unsaturated, or a C1-C8 hydrocarbon group which is chained or branched, saturated or unsaturated and has an ether or thioether bond; R1, R2, R3 and R4 each independently represent a C1-C6 alkyl group or C2-C6 alkenyl group; n, p, q and r each represents any integer of 0 to 4; and m represents any integer of 0 to 2]. Also provided is a recording material with a sufficient color-forming sensitivity, superior storage stability, and especially with an extremely little background fogging in a heat resistance test.
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- Green oxidations. Manganese(II) sulfate aided oxidations of organic compounds by potassium permanganate
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The oxidation of arenes and sulfides by potassium permanganate was accomplished in good yields under solvent free and heterogeneous conditions when manganese(II) sulfate is used as a solid support. After extraction of the organic products, the inorganic products can be reoxidized to permanganate. This result is important because it provides an approach to oxidation reactions that is, in theory, infinitely sustainable. Springer-Verlag 2007.
- Shaabani, Ahmad,Rahmati, Abbas,Sharifi, Masoumeh,Rad, Jafar Mogimi,Aghaaliakbari, Behnaz,Farhangi, Elham,Lee, Donald G.
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p. 649 - 651
(2008/02/07)
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- Separation of 2,4′- and 4,4′-dihydroxydiphenyl sulfones
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To develop a procedure for separating 2,4′- and 4,4′- dihydroxydiphenyl sulfones, their acidity and solubility in water were studied. Pleiades Publishing, Inc., 2006.
- Belyaev,Vershinin,Gromov,Kuznetsov
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p. 425 - 429
(2008/02/03)
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- Process for producing high-purity 4,4'-dihydroxydiphenyl sulfone
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The present invention provides a process for producing 4,4′-dihydroxydiphenylsulfone of very high purity. In particular, the present invention provides a process for producing 4,4′-dihydroxydiphenylsulfone of high purity comprising the steps of subjecting phenol in combination with a sulfonating agent or phenolsulfonic acid to a dehydration reaction in the presence of an aromatic nonpolar solvent while suspending the resulting dihydroxydiphenylsulfone therein, mixing the reaction suspension with a polar solvent to at least partially dissolve the dihydroxydiphenylsulfone, and precipitating 4,4′-dihydroxydiphenylsulfone.
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Page/Page column 5-6
(2008/06/13)
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- PROCESS FOR PRODUCING DIHYDROXYDIPHENYL SULFONE
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The present invention provides a process for producing dihydroxydiphenylsulfone wherein trihydroxytriphenylsulfone and coloring impurities are effectively removed without altering the isomeric composition of dihydroxydiphenylsulfone. In particular, the present invention provides a process for producing dihydroxydiphenylsulfone comprising the steps of dissolveing or suspending in an aqueous solvent crude dihydroxydiphenylsulfone containing trihydroxytriphenylsulfone, adjusting the pH to 5-7, optionally cooling, and separating the crystalline dihydroxydiphenylsulfone thus precipitated.
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Page/Page column 4
(2008/06/13)
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- PROCESS FOR PRODUCING 2,4'-DIHYDROXYDIPHENYL SULFONE
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A process for producing 2,4'-dihydroxydiphenylsulfone which comprises separating 4,4'-dihydroxydiphenylsulfone by crystallization from a mixture containing 4,4'-dihydroxydiphenylsulfone, 2,4'-dihydroxydiphenylsulfone, phenolsulfonic acid and phenol which is obtained by dehydration of phenol and sulfuric acid or phenolsulfonic acid to obtain a mixture having a content of 2,4'-dihydroxydiphenylsulfone greater than the content of 4,4'-dihydroxydiphenylsulfone, crystallizing 2,4'-dihydroxydiphenylsulfone by adjusting the composition of the solvent of the obtained mixture so that the ratio of the amounts by weight of phenol to water is 10:90 to 90:10, and separating 2,4'-dihydroxydiphenylsulfone by filtration; and a process as described above in which the filtrate obtained by the filtration is used as the raw material for the hydration.
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- PROCESS FOR PRODUCING 4,4-BISPHENOL SULFONE
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A process for producing 4,4'-bisphenol sulfone by reacting phenol with sulfuric acid, which includes conducting a dehydration reaction in a mixed solvent including an aliphatic saturated hydrocarbon having a boiling point of 175°C or higher and mesitylene, and finally distilling off the mesitylene from the reaction system, or includes conducting the reaction in a solvent including an aliphatic saturated hydrocarbon in a reaction vessel equipped with a fractionating device. Thus, 4,4'-bisphenol sulfone can be produced in high yield with a high operating efficiency. Also, provided is a process for easily producing 4,4'-bisphenol sulfone having a high purity which includes conducting the reaction in a solvent containing an aliphatic saturated hydrocarbon, subsequently adding a C1-3 alcohol to the reaction mixture, separating an alcohol layer, and recrystallizing the 4,4'-bisphenol sulfone from the alcohol layer.
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Page column 16
(2008/06/13)
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- PROCESS FOR PRODUCING MIXTURE OF DIHYDROXYDIPHENYLSULFONE ISOMERS
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The present invention provides a process for producing a mixture of dihydroxydiphenylsulfone isomers containing 2,4'-dihydroxydiphenylsulfone, the process comprising heating 4,4'-dihydroxydiphenylsulfone or a mixture of dihydroxydiphenylsulfone isomers containing at least 85 wt.% of 4,4'-dihydroxydiphenylsulfone in the presence of phenol and sulfuric or sulfonic acid.
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- PROCESS FOR PRODUCING MIXTURE OF DIHYDROXYDIPHENYLSULFONE ISOMERS
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The present invention provides a process for producing a mixture of 4,4'- and 2,4'-dihydroxydiphenylsulfones comprising heating trihydroxytriphenyldisulfone or a mixture of dihydroxydiphenylsulfone isomers containing trihydroxytriphenyldisulfone in the presence of phenol and an acid catalyst.
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- Method for producing 4-amino-5-chloro-1-phenyl pyridazinone-(6)
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In a process for preparing 4-amino-5-chloro-1-phenylpyridazin-6-one by reacting 4,5-dichloro-1-phenylpyridazin-6-one with aqueous ammonia in the presence of a catalyst, the catalyst used is soluble in the aqueous alkaline reaction medium but is essentially insoluble in the reaction medium which has been acidified after removal of the 4-amino-5-chloro-1-phenylpyridazin-6-one. The process of the present invention makes it possible for the catalyst to be recovered and reused in a simple manner.
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- Polymer electrolyte and process for producing the same
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A polymer electrolyte having, in a main chain, a structural unit represented by the following formula (1):-[Ar1-(SO2-N-(X+)-SO2-Ar2)m-SO2-N-(X+)-SO2-Ar1-O]- wherein Ar1 and Ar2 independently represent a divalent aromatic groups, m represents an integer of 0 to 3, and X+ represents an ion selected from hydrogen ion, an alkali metal ion and ammonium ion, which is excellent in proton conductivity, thermal resistance and strength. The polymer electrolyte is soluble in solvents and has excellent film forming property and recycling efficiency.
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- SLIME REMOVER AND SLIME PREVENTING/REMOVING AGENT
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A drainage slime remover capable of spreading a solution of a solid over slime generated wall surface portions, comprising a solid containing a microorganism growth retarding substance and a container which has a shape for permitting the installation thereof at the inlet or upper portion of a drain outlet and stores the solid characterized in that the container has drain flow-in holes having an opening capable of controlling a drain flow-in amount and provided in the upper surface or the upper side portion of the container and solution flow-out holes having an opening capable of controlling a flow-out amount of a solid solution and provided in the bottom or the lower side portion of the container or additionally in the side surface thereof, and a slime preventing/removing agent which can remove slime from portions such as kitchen sinks and bathroom drain outlets where slime is grown by metabolites such as miscellaneous germs and mildews and which can prevent the occurrence of slime safely and for an extended period of time.
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- Method for manufacturing bisphenol
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A method for manufacturing bisphenol by reacting phenols and ketones, characterized (1) in that an alkali metal compound and/or alkaline earth metal compound is added to bisphenol obtained by reacting a phenol and a ketone, and (2) in that the basicity of the bisphenol is adjusted so as to be equivalent to an amount of 1 × 10-8to 1 × 10-6moles of bisphenol as disodium salt with respect to 1 mole of bisphenol provides a bisphenol in which there is no residue of the organic catalysts ordinarily used in manufacturing bisphenol, so that byproducts are not produced during purification, allowing bisphenol with outstanding color tone, thermal resistance, etc., to be obtained.
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- Process for the purification of bisphenols and preparation of polycarbonates therefrom
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A phenol and a ketone are reacted to form bisphenol, and the liquid bisphenol obtained or a mixed solution of said solution and a phenol is filtered through a calcined metal filter to obtain bisphenol which makes it possible to efficiently obtain bisphenol which either does not contain fine particulate impurities or contains such impurities only in minute amounts, and a method for manufacturing polycarbonate using bisphenol obtained bythis method. The filtration grade of the calcined metal filter should be 1.0 μm or less. After filtering, the calcined metal filter can be backwashed or chemically washed and then reused. The bisphenol should preferably be bisphenol A.
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- A supramolecular carpet formed via self-assembly of bis(4,4′-dihydroxyphenyl) sulfone
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Bis(4,4′-dihydroxyphenyl) sulfone 1 exploits its tetrahedrally disposed complementary hydrogen bonding sites to generate a unique doubly interwoven molecular carpet architecture in the solid state.
- Davies, Caitlin,Langler, Richard F.,Sharma, C. V. Krishnamohan,Zaworotko, Michael J.
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p. 567 - 568
(2007/10/03)
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- Method of producing A 2,4'-dihydroxydiphenylsulfone
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High purity 2,4'-dihydroxydiphenylsulfones useful as developers for thermal recording paper can be produced efficiently and with high selectivity by reacting one or more phenols and sulfuric acid in the presence as of at least one of phosphonic acid, phosphinic acid and salts thereof, in the absence of a solvent or in the presence of an aromatic hydrocarbon solvent having a boiling point at atmospheric pressure of 130° to 200° C., and then purifying the thus-produced crude 2,4'-dihydroxydiphenylsulfones using a mixed solvent containing (1) 5 to 20 weight % of at least one lower aliphatic alcohol and 95 to 80 weight % of at least one aromatic hydrocarbon which does not contain halogen, (2) 10 to 40 weight % of at least one ketone and 90 to 60 weight % of at least one aromatic hydrocarbon which does not contain halogen or (3) 10 to 40 weight % of at least one ester of acetic acid and 90 to 60 weight % of at least one aromatic hydrocarbon which does not contain halogen.
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- Salicylic acid derivatives
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The heat-sensitive recording material disclosed comprises a colorless or pale colored dyestuff precursor, one or more salicylic acid derivative of the formula (1) or metal salt of the derivative and an aliphatic amide compound having 18?60 carbon atoms in molecular structure, and is excellent in thermal response and preservation stability of white portions and images. STR1 wherein X1 and X2 are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group or an aryl group, Y1 and Y2 are an oxygen atom or a sulfur atom, R1 is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group, and R2 is an alkyl group, an alkenyl group, an aralkyl group or an aryl group.
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- Clathrate composition including essential oils and method of using same
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A composition for killing harmful organisms, which contains a clathrate compound composed of one or more natural essential oils and/or derivatives thereof selected from the group consisting of the following substances (1) to (22) and a polymolecular host compound capable of including the natural essential oils and/or derivatives thereof: (1) hinoki oil; (2) 1,8-cineole; (3) l-α-terpineole; l-carbone; (5) l-menthone; (6) d-pulegone; (7) citronellal; (8) linelool oxide; (9) d,l-citronellol; (10) 3,3,5-trimethylcyclohexanol; (11) l-perillaldehyde; (12) l-carveol; (13) myrtenal; (14) peppermint oil; (15) eucalyptus oil; (16) cinnamic aldehyde; (17) α-bromo-cinnamic aldehyde; (18) salicylaldehyde; (19) benzaldehyde; (20) paraphenyl-propionaldehyde; (21) paratolualdehyde; and (22) l-menthol.
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- Preparation of bis(4-hydroxyphenyl)sulfone
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A process for the preparation of bis(4-hydroxyphenyl)sulfone by reacting phenol with sulfuric acid in the presence of a solvent at from 130° to 220° C. and in the presence or absence of a sulfonating assistant, wherein the bis(4-hydroxyphenyl)sulfone formed is selectively deposited on a nucleating surface during or after the reaction, and thus removed from the reaction medium.
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- Method for preparing aromatic bischloroformate compositions
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Bischloroformate oligomer compositions are prepared by passing phosgene into a heterogeneous aqueous-organic mixture containing at least one dihydroxyaromatic compound, with simultaneous introduction of a base at a rate to maintain a specific pH range and to produce a specific volume ratio of aqueous to organic phase. By this method, it is possible to employ a minimum amount of phosgene. The reaction may be conducted batchwise or continuously. The bischloroformate composition may be employed for the preparation of cyclic polycarbonate oligomers or linear polycarbonate, and linear polycarbonate formation may be integrated with bischloroformate composition formation in a batch or continuous process.
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- Bischoloroformate preparation method with phosgene removal and monochloroformate conversion
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Aqueous bischloroformates are prepared by the reaction of a dihydroxyaromatic compound (e.g., bisphenol A) with phosgene in a substantially inert organic liquid (e.g., methylene chloride) and in the presence of an aqueous alkali metal or alkaline earth metal base, at a pH below about 8. After all solid dihydroxyaromatic compound has been consumed, the pH is raised to a higher value in the range of about 7-12, preferably 9-11, and maintained in said range until a major proportion of the unreacted phosgene has been hydrolyzed. At the same time, any monochloroformate in the product may be converted to bischloroformate.
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- Cyclic monocarbonate bishaloformates
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Cyclic monocarbonate bischloroformates are prepared by the reaction of a carbonyl halide such as phosgene with a bridged substituted resorcinol or hydroquinone such as bis(2,4-dihydroxy-3-methylphenyl)methane or bis(2,5-dihydroxy-3,4,6-trimethylphenyl)methane in the presence of aqueous alkali metal hydroxide. The cyclic monocarbonate bischloroformates may be used for the preparation of linear or cyclic polycarbonates containing cyclic carbonate structural units, which may in turn be converted to crosslinked polycarbonates.
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- Process for preparing 4,4'-dihydroxydiphenyl sulfone having high purity
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The process of the present invention is a process for preparing 4,4'-dihydroxydiphenyl sulfone by subjecting phenol, and a sulfonating agent or phenolsulfonic acid to a dehydration reaction in the presence of a solvent, subsequently maintaining the reaction system at a temperature of between 100° to 200° C. and removing the solvent from the reaction system to cause the dehydration reaction to further proceed while allowing 4,4'-dihydroxydiphenyl sulfone to separate out and to subject dissolved 2,4'-dihydroxydiphenyl sulfone formed as a by-product to an isomerization reaction for converting the by-product to 4,4'-dihydroxydiphenyl sulfone, and eventually removing the solvent and the unreacted phenol from the system substantially entirely to complete the isomerization reaction, the process being characterized in that an aromatic sulfonic acid represented by the formula STR1 wherein X is a halogen atom, n is 0, 1 or 2, and m is 1 of 2 is caused to be present in the reaction system. 4,4'-Dihydroxydiphenyl sulfone can be produced by the process with a high purity and in a high yield.
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- Polyetherimide bisphenol compositions
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Polyetherimide bisphenols and bischloroformates are prepared by the reaction of dianhydrides or certain bisimides with aminophenols or mixtures thereof with diamines. They are useful as intermediates for the preparation of cyclic heterocarbonates, which may in turn be converted to linear copolycarbonates. The bisphenols can also be converted to salts which react with cyclic polycarbonate oligomers to form block copolyetherimidecarbonates.
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- Process for producing 4,4'-dihydroxydiphenylsulfone of high purity
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In a process for producing 4,4'-dihydroxydiphenylsulfone by reacting phenol with sulfuric acid in the presence of a solvent, an improvement which comprises using at least a member selected from the group consisting of chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene, diethylbenzene, xylene, decalin, tetralin and tetrachloroethane as the solvent and removing said solvent progressively and finally substantially completely from the mixture while maintaining the reaction mixture at a temperature of about 160° to about 200° C. to effect precipitation of 4,4'-dihydroxydiphenylsulfone and isomerization of 2,4'-dihydroxydiphenylsulfone to 4,4'-dihydroxydiphenylsulfone.
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- Color of maleic anhydride
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Discoloration of maleic anhydride is minimized by first passing the maleic anhydride in molten or dissolved form through a bed of cation exchange resin and then adding to the maleic anhydride a small amount of 3,3'-thiodipropionitrile.
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- Preparation of 4,4'-dihydroxydiphenylsulfones
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A phenol is reacted with sulphur trioxide in the presence of liquid hydrogen fluoride to form a 4,4'-dihydroxydiphenylsulphone. A molar excess of hydrogen fluoride and stoichiometric proportions of sulphur trioxide and phenol or a slight excess of sulphur trioxide over phenol are preferred.
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- Ethylenic silicon compounds and thermoplastic elastomers obtained therefrom
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The invention provides organosilicon compounds of the formula: STR1 in which: N IS 1, 2 OR 3; Each R, which may be identical or different, is a monovalent organic group which contains a carbon-carbon double bond and from 2 to 10 carbon atoms; Each R1, which may be identical or different, is a straight or branched alkyl radical optionally substituted by one or more halogen atoms or cyano groups; an aryl radical or an alkylaryl radical optionally substituted by one or more halogen atoms; R2 is a straight or branched divalent alkylene or alkylidene radical possessing up to 4 carbon atoms; X is a divalent radical consisting of, or containing, at least one hetero-atom selected from oxygen, sulphur and nitrogen atoms, the radical being attached to the radical R2 via a said hetero-atom; G is an organic radical of valency (m+ l) possess from 1 to 30 carbon atoms; m is 1, 2 or 3; And each Y, which may be identical or different, is a functional group selected from: --NO2, STR2 --COOM (where M represents a sodium, potassium or lithium atom); --COOR4 ; STR3 --COCl; --OH; --OR4 ; STR4 --SH; --SR4 ; STR5 --CONH2 ; --CSNH2 ; --CN; --CH2 --NH2 ; --CHO; STR6 --NCO; STR7 wherein R3 represents a hydrogen atom or a straight or branched alkyl radical possessing up to 6 carbon atoms and R4 represents an alkyl radical possessing up to 4 carbon atoms, with the proviso that two Y groups can together constitute an imide group STR8 wherein R5 represents a hydrogen atom or a straight or branched alkyl radical possessing up to 4 carbon atoms. These are useful intermediates in the preparation of disilanes and silicon polymers, in particular of polyethylenic silicon compounds which can be polymerized with an α, ω-dihydrogenopolysiloxane to give thermoplastic elastomers.
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- Process for selectively producing high-yield, high-purity 4,4-substituted diaryl sulfones
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4,4'-substituted diaryl sulfones of high yield and high purity are selectively formed by the oxidation of 4,4'-substituted diaryl sulfides and diaryl sulfoxides, respectively, employing an aqueous slurry, including a molybdic acid-peroxide-catalyzed oxidation system, the aqueous slurry being maintained at a pH of less than about one.
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