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[ CAS No. 3085-42-5 ]

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Chemical Structure| 3085-42-5
Chemical Structure| 3085-42-5
Structure of 3085-42-5 * Storage: {[proInfo.prStorage]}

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Product Details of [ 3085-42-5 ]

CAS No. :3085-42-5 MDL No. :MFCD00000618
Formula : C12H8Cl2OS Boiling Point : 406.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :271.16 g/mol Pubchem ID :18329
Synonyms :

Safety of [ 3085-42-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3085-42-5 ]

  • Downstream synthetic route of [ 3085-42-5 ]

[ 3085-42-5 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 3085-42-5 ]
  • [ 5181-10-2 ]
YieldReaction ConditionsOperation in experiment
94% With silica bromide; In dichloromethane; at 20℃; for 0.116667h;Inert atmosphere; General procedure: In a typical procedure, diphenyl sulfoxide (2.2 g, 0.01 mol) and brominated silica (18.18 g, 40 mmole Br/g silica) are mixed in an aprotic solvent, e.g. dichloromethane (2 mL) or carbon tetrachloride, at room temperature with exclusion of atmospheric moisture, for 5 min. Diphenyl sulfide is isolated in pure state by simple filtration and evaporation of the solvent (1.84, 99%).
94% In 25 ml of the reaction tube for vacuum, nitrogen three times, placed at 0 ,Under the protection of nitrogen, 4,4-dichlorodiphenylsulfoxide was added(135.5 mg, 1.0 eq)And re-distilled dichloromethane DCM (3 mL, 0.17 M),Then oxalyl chloride (63 muL, 1.5 eq.) Was added and after reaction for 30 minutes, triethylene diamine DABCO (112.2 mg, 2.0 eq.) Was added.After five minutes, the reaction process was tracked by thin layer chromatography,The developing agent was a petroleum ether / ethyl acetate volume ratio of 40/1, the reaction was monitored,The reaction mass was concentrated by vacuum and separated by column chromatography to give a white solid in a yield of 94%.
93% With tantalum pentachloride; sodium iodide; In acetonitrile; at 20℃; for 0.0833333h; General procedure: In a 10 mL round-bottom flask, to a solution of diphenylsulfoxide (202 mg, 1.0mmol) in CH3CN (4 mL), tantalum (IV) chloride (179 mg, 0.5 mmol) and sodium iodide (300 mg, 2.0 mmol) were added at room temperature. The mixture turned dark brown almost immediately and the progress of the reaction was followed by TLC. After completion of the reaction (3 min), the reaction mixture was diluted with water and then extracted with ethyl acetate. The combined organic extracts were washed successively with 10% aq Na2S2O3 and H2O. The organic layer was separated and dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified through silicagel column chromatography (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95%).
92% With hafnium tetrachloride; zinc; In acetonitrile; at 20℃; for 2.5h; General procedure: Diphenylsulfoxide (101 mg, 0.5 mmol) and hafnium(IV) chloride (320 mg, 1.0 mmol) were mixed in CH3CN (5 mL) and zinc powder (131 mg, 2.0 mmol) was then added to this solution. The whole mixture was stirred for 3 h at room temperature and the progress of the reaction was followed by TLC. On completion, the solvent was removed under reduced pressure and the residue was extracted successively with ethyl acetate, washed with water and brine. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography on a silica gel (hexane:ethyl acetate = 2:1) to afford diphenylsulfide (88 mg, 95%). All of the products were identified by comparison of their spectroscopic data with authentic samples.[34]
92% With indium; tantalum pentachloride; In acetonitrile; at 20℃; for 1h;Sonication; General procedure: Indium powder (229 mg, 2.0 mmol) and tantalum(V) chloride(358mg, 1.0mmol)weremixed inCH3CN(5 mL). The resultingmixture was sonicated for 0.5 h to produce a solution of the lowvalenttantalum-indium complex. Diphenyl sulfoxide (101 mg,0.5 mmol) was then added to this solution and the reactionmixturewas stirred for 3.0 h at room temperature. The progressof the reaction was followed by TLC. On completion, the solventwas removed under reduced pressure and the residue wasextracted successively with ethyl acetate, washed with water andbrine. The organic layerwas separated and dried over anhydrousNa2SO4. The crude product was purified by column chromatographyon silica gel (hexane:ethyl acetate=2:1) to afford diphenylsulfide (86mg, 92%). All of the productswere identified by comparisonof their spectroscopic data with authentic samples.
87% With [ReOCl3(PPh3)2]; In chloroform; for 17h;Reflux; General procedure: To a solution of ReOCl3(PPh3)2 (10.0 mol %) in CHCl3 (3 mL) was added the sulfoxide (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Table 1, Table 2 and Table 3) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford sulfides and sulfones, which are all known compounds.
87% With sodium iodide; at 20℃; for 4h;Green chemistry; General procedure: To a solution of a sulfoxide (1 mmol) in PEG-200 (1 ml), silica sulfuric acid (374 mg, equal to 2.2 mmol H+) and NaI (2.2 mmol) were added. The mixture was stirred magnetically at room temperature and the progress of the reaction was monitored by TLC or GC until the starting sulfoxide was completely consumed. The reaction mixture was then neutralized using NaOH solution (0.5 M, 1 ml), and subsequently the enough well-powdered Na2S2O3 · 5H2O was added to mixture with stirring to react with iodine. The mixture was then extracted with EtOAc (5 × 1 ml). The organic layers were decanted, combined, dried over Na2SO4, filtered and concentrated. The crude product was further purified by silica gel chromatography using n-hexane as eluent to provide the desired product in excellent yields.
80% With triethylsilane; tris(pentafluorophenyl)borate; In neat (no solvent); at 100℃; for 8h;Glovebox; Inert atmosphere; General procedure: In a glovebox, an oven-dried 1-mL screw-capped sealed tube with a magnetic stir bar was charged with B(C6F5)3 (10 mol%), Et3SiH (10 equiv), and the indicated oxidized sulfur compound (0.20 mmol). The tube was sealed properly and transferred to an oil bath preheated at100 C. After 8 h, the reaction was cooled to r.t. and passed through asmall plug of silica gel using Et2O. The crude material was collected ina glass vial and subjected to GLC analysis to determine the conversion with respect to starting material. The ethereal solution was dried (Na2SO4) and filtered, and the solvent was removed under reduced pressure. The mixture was then subjected to high vacuum at 70 C until the unreacted hydrosilane was removed from the system. If needed, the residue was purified further by flash column chromatography (silica gel, cyclohexane/Et2O 9:1) to afford the desired sulfides.
> 99%Chromat. With isopropyl alcohol; In toluene; at 110℃; for 1h;Inert atmosphere; Green chemistry; General procedure: RuNP/HAP (0.05 g: Ru 0.025 mmol) and iso-propanol (0.5 mL) were added to a solution of diphenylsulfoxide in toluene (0.1 M, 0.5 mmol). The mixture was stirred at 110 oC for 1 h. The yields of the products were determined by GC using naphthalene as an internal standard.
With thionyl chloride; triphenylphosphine; In tetrahydrofuran; at 20℃; for 5.5h; General procedure: Typical Procedure for Diaryl Sulfide. To a solution ofSOCl2 (1.5 mmol) in dry THF (10 mL) was added drop-wise aryl magnesium halide (3.0 mmol in THF or Et2O) at0 C. The resulting solution was stirred for 2 h at a slowrising from 0 C to room temperature. To the reaction mix-ture were added dropwise a solution of PPh3 (3.0 mmol) in dry THF (2 mL) via cannula and subsequently additionalSOCl2 (3.0 mmol) at room temperature. The resulting solu-tion was stirred until the sulfoxide intermediate was con-sumed completely by TLC (thin layer chromatography)monitoring at room temperature and quenched withH2O. The reaction mixture was extracted with Et2O andH2O. The organic layer was separated, dried over Na2SO4,and concentrated. The residue was subjected to columnchromatography with only hexanes or hexanes-EtOAc(30:1 - 20:1) as eluent to afford the corresponding sulfide.
> 40%Chromat. With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In toluene; at 80℃; for 4h;Inert atmosphere; General procedure: To a magnetically stirred solution of aryl sulfoxide (0.18 M; 50 mg, ca. 2.5 mmol) in toluene (ca. 1.5 mL) kept under inert atmosphere, tris(trimethylsilyl)silane (2 equiv) and AIBN (0.2 equiv) were consecutively added and the reaction mixture was warmed up at 80 C. The reaction was monitored by gas chromatography, after calibration of the equipment using the reference compounds. The consumption of the starting material was evidenced by GC together with the formation of the sulfide product, and quantitatively evaluated by the calibration curves of commercially available compounds.
With MoO3#dotPt; hydrogen; In toluene; at 20℃; under 760.051 Torr; for 4h;Irradiation; General procedure: 50 mg of Pt / MoO 3 (200) obtained in Production Example 1,Put in a container made of Pyrex (registered trademark)Preliminary reduction was carried out for 30 minutes under 1 atm hydrogen flow (20 mL / min). After preliminary reduction,0.2 mmol of diphenyl sulfoxide (substrate)0.1 mmol of biphenyl (internal standard substance)10 ml of toluene (solvent) was added, and under hydrogen flow (10 mL / min) at room temperature,The mixture was allowed to react for 7 hours in the dark while stirring. After the reaction,The catalyst was removed from the reaction solution using a membrane filter,After purification by column chromatography and recrystallization,37 mg of diphenyl sulfide was obtained. Diphenyl sulfide was obtained in the same manner as in Example 1 except that the sulfoxide deoxidation reaction was conducted under irradiation with visible light (> 420 nm).A 500 W mercury-xenon lamp (SUPER BRIGHT 500, XEF-501 S) manufactured by Mitsunaga Electric Works Co., Ltd. was used as a visible light irradiation device.The results of the conversion of the sulfide obtained in the reactions of Example 1 and Example 2 are shown in FIG. 7.In Example 1 reacted in the dark, it took 7 hours and in Example 2 reacted under visible light irradiation it took 3 hours,Diphenyl sulfide could be obtained with a conversion of 99% or more.In Example 1, since the conversion was 67% when the reaction time was 3 hours, it was revealed that about 2 times the reaction rate was obtained under irradiation with visible light. Example 4 The corresponding sulfide was obtained in the same manner as in Examples 1 and 2 except that 4-chlorophenyl sulfoxide was used as a substrate in place of diphenyl sulfoxide.

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  • 3
  • [ 3085-42-5 ]
  • bis-(4-chloro-3-nitro-phenyl)-sulfoxide [ No CAS ]
  • 4
  • [ 24824-20-2 ]
  • [ 3085-42-5 ]
  • 5
  • [ 108-90-7 ]
  • [ 3085-42-5 ]
YieldReaction ConditionsOperation in experiment
71% With aluminum (III) chloride; thionyl chloride; at 25℃; General procedure: The reactions were conducted in the fume hood at 25 Cand 70 C, respectively, with the molar ratio of PhX:SOCl2:AlCl3 being 2:1:1 and usage of SOCl2 approximately 10 mmol. For eachreaction, granular AlCl3 was added piecewise to the PhX-SOCl2 mixture (X=CH3 or Cl) in a large test tube (~ 80 mL) as follows: First, one piece of AlCl3 was added and gas (HCl) bubbles started to form immediately. The piece of AlCl3 was crushed using a stirring rod. When most of the piece of AlCl3 had dissolved and bubbling occurredvery slowly, another piece of AlCl3 was added. All the AlCl3 granules were eventually added into the PhX-SOCl2 mixture piece-by-piece. The solution was initially light green and it turned dark green as the reaction went to completion, indicated by ceasing of bubbling after all the AlCl3 had been added. Then iced water (40 mL) was poured into thereaction mixture and the green colour disappeared. This was followed by addition of diethyl ether (20 mL). All the contents were transferredinto a separating funnel and shaken well to assure the organic productbeing fully extracted into the ether phase. The ether and water phaseswere separated. The water phase was extracted by diethyl ether (20 mL) again. Then all the ether solutions were combined and dried by anhydrous sodium sulfate. The dried ether solution was filtered off and left in the fume hood. Eventually, all the diethyl ether solvent evaporated, giving the final reaction product. The product was thencharacterised by GC-MS, and the results are shown in Table 1.
98%Chromat. With aluminum (III) chloride; thionyl chloride; at 0℃; for 2h; General procedure: Approach 1: The reactions were conducted in the fumehood at0C with the molar ratio of PhCl : SOCl2 : MCl3 being 1:1:1and usage of SOCl2 approximately 10 mmol [PhCl (1.13 g,10.0 mmol), SOCl2 (1.19 g, 10.0 mmol), and AlCl3 (1.33 g,10.0 mmol) or FeCl3 (1.62 g, 10.0 mmol)]. For each reaction,SOCl2 was added dropwise to the PhCl-MCl3 (M = Fe or Al)mixture in a large test tube (80 mL) with constant stirring (Forthe AlCl3-catalyzed reaction, SOCl2 was added after the granular AlCl3 had been mostly crushed). The reaction took placequickly, indicated by bubbling (formation of HCl) as above.After all the SOCl2 was added, the reaction went to completion(in about 2 h), indicated by the cessation of bubbling. Then icedwater (40 mL) was poured into the reaction mixture. This wasfollowed by the addition of diethyl ether (20 mL). All the contents were transferred into a separatory funnel and shaken well to ensure that the organic product had been fully extracted intothe ether phase. The ether and water phases were separated. Thewater phase was extracted by diethyl ether (20 mL) again. Thenall the ether solutions were combined and dried by anhydroussodium sulfate. The dried ether solution was fltered o and leftin the fumehood. Eventually, all the diethyl ether solvent evaporated, giving the fnal reaction product. The product was thencharacterized by GC-MS, and the results are shown in Table 1(Entry 1).
With aluminum (III) chloride; thionyl chloride; tetrabutylammomium bromide; at 25℃; for 2h; (1) chlorobenzene and thionyl chloride are subjected to a Friedel-Craft reaction under the action of a catalyst to obtain 4,4'-dichlorodiphenyl sulfoxide, and the amount of the catalyst is 10% of the total mass of thionyl chloride and chlorobenzene.The reaction temperature of Fuke is 25 C for 2 h, and the molar ratio of thionyl chloride to chlorobenzene is 1:4.The catalyst was anhydrous aluminum trichloride and tetrabutylammonium bromide mixed in a mass ratio of 3:1.
With aluminum (III) chloride; thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride; at 10 - 100℃; for 4h; (1) performing a Friedel-Craft reaction of thionyl chloride and chlorobenzene under the action of a catalyst,The reaction temperature of the Friedel-Crafts is 30 C for 1 h, and the molar ratio of thionyl chloride to chlorobenzene is 1:4.The catalyst is anhydrous aluminum trichloride and benzyl triethyl ammonium chloride in a mass ratio of 3:1;(2) After the end of the mixed reaction, the temperature was lowered to 10 C for 1 h, and then heated to 100 C for 2 h.Then cooling, crystal precipitation, filtration to obtain 4,4'-dichlorodiphenyl sulfoxide;

  • 6
  • [ 106-39-8 ]
  • [ 3085-42-5 ]
  • [ 125428-43-5 ]
  • 7
  • [ 115-20-8 ]
  • [ 3085-42-5 ]
  • C12H8Cl2OS*C2H3Cl3O [ No CAS ]
  • 8
  • [ 75-80-9 ]
  • [ 3085-42-5 ]
  • C12H8Cl2OS*C2H3Br3O [ No CAS ]
  • 9
  • [ 5181-10-2 ]
  • [ 3085-42-5 ]
  • [ 80-07-9 ]
  • 10
  • [ 1016-82-6 ]
  • [ 945-51-7 ]
  • [ 3085-42-5 ]
  • 11
  • [ 3085-42-5 ]
  • [ 78718-15-7 ]
  • [ 83373-39-1 ]
  • 12
  • [ 3085-42-5 ]
  • [ 5181-10-2 ]
  • [ 80-07-9 ]
YieldReaction ConditionsOperation in experiment
33%; 65% With [ReOCl3(PPh3)2]; In ethanol; for 18h;Reflux; General procedure: To a solution of ReOCl3(PPh3)2 (10.0 mol %) in CHCl3 (3 mL) was added the sulfoxide (1.0 mmol). The reaction mixture was heated at reflux temperature under air atmosphere (the reaction times are indicated in the Table 1, Table 2 and Table 3) and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was evaporated and purified by silica gel column chromatography with n-hexane to afford sulfides and sulfones, which are all known compounds.
  • 13
  • [ 3085-42-5 ]
  • [ 80-07-9 ]
YieldReaction ConditionsOperation in experiment
99.3% With dihydrogen peroxide; acetic acid; at 80℃; for 2h; (2) Dissolve <strong>[3085-42-5]4,4'-dichlorodiphenyl sulfoxide</strong> with glacial acetic acid, and add 30% hydrogen peroxide to carry out oxidation reaction. The oxidation reaction temperature is 80 C for 2 h.Obtaining crude 4,4'-dichlorodiphenyl sulfone;(3) The crude 4,4'-dichlorodiphenyl sulfone is dissolved in glacial acetic acid, and hydrogen peroxide is added for oxidation reaction. The concentration of hydrogen peroxide used is 30%, 30% hydrogen peroxide and crude 4,4'-dichlorodiphenyl sulfone. The mass ratio is 1:6,The oxidation reaction temperature is 60 C, the time is 0.5 h, and finallyObtain 4,4'-dichlorodiphenyl sulfone.The prepared 4,4'-dichlorodiphenyl sulfone has a purity of 99.7%.The refined yield was 99.3%.
96.2% With N-(n-butyl)tridemorph phosphotungstate; dihydrogen peroxide; In benzene; at 90℃; for 2h;Catalytic behavior; 27 g (about 0.1 mol) of <strong>[3085-42-5]bis(4-chlorophenyl)sulfoxide</strong> was dissolved in 50 ml of benzene, catalyst A 2.8 g was added and 30 ml of 50% hydrogen peroxide was added dropwise at 90 C. The reaction was stirred for 120 minutes, then the mixture was allowed to cool to room temperature, separated and filtered to recover the catalyst. Next, the upper layer organic layer was concentrated, separated and dried to give bis(4-chlorophenyl)sulfone 27.6 g, recovery solvent, product yield was 96.2%.
96.8% With sulfuric acid; dihydrogen peroxide; acetic acid; at 80℃; for 1.66667h; Take <strong>[3085-42-5]4,4'-dichlorodiphenylsulfoxide</strong> 27.12 g (0.1 mol) was dissolved in 30 mL of dichloropropane and 5 mL of glacial acetic acid6.0% of catalyst sulfuric acid with a mass fraction of 50%, and 10 mL of 40% hydrogen peroxide was added dropwise at 80 C, stirring reaction 100Min, and then allowed to stand for cooling to room temperature. The solid was separated by filtration. The solid was washed with a small amount of water. The filtrate was separated and the organic layerThe solvent was separated and the crystals were separated, the solid was combined and dried to give 27.8 g of 4,4'-dichlorodiphenylsulfone, the product yield was 96.8%The melting point of 147-149 C, the chromatographic content of 99.8%. The upper layer of sulfuric acid, acetic acid aqueous solution, recycling to be used the next time.
93.33% With sulfuric acid; dihydrogen peroxide; acetic acid; at 80℃; for 1.5h; To a 250 mL four-necked flask equipped with a stirrer, a thermometer, and a condenser tube at 25C,Add 5.3g glacial acetic acid, 5g hydrogen peroxide (mass fraction 30%),0.5g concentrated sulfuric acid,The reaction was stirred for 12 h at ? 25 C and transferred as an oxidant to the balance feeder for use.At 80C,With a balanced feeder,Blender,In a 250 mL four-necked flask with a thermometer and a condenser tube,Add 10g<strong>[3085-42-5]4,4'-dichlorodiphenyl sulfoxide</strong>,After 17g acetic acid,The oxidant was added dropwise from the balancer (complete within 0.5 h).Then continue to react 1h,At the end of the reaction, cool down to below 5C.filter,washing,Dry 4,4'-dichlorodiphenylsulfone crude product 10.37 g,3.7% weight gainThe crude product yield was 97.95%.Melting range 146148C,Recrystallization from ethanol gives white crystals,The recrystallization yield was 93.33%.
Example 5: Oxidation of 4,4'-Dichlorodiphenylsulfoxide (DCDPSO) with H202 by use of a TiMWW obtained according to Example 1 In a glass autoclave cooled with ice, 1.0 g of the TiMWW obtained according to Example 1 (1.4) were introduced, followed by the addition of a separately prepared solution of 60 g 1-methyl-2- pyrolidone and 5.0 g DCDPSO (commercially available from Sigma-Aldrich, CAS 3085-42-5). This corresponds to about 1.5 weight-% TiMWW catalyst relative to the total amount of the obtained suspension. After the addition of the reactants the autoclave was closed and flushed with nitrogen. The suspension was stirred with a magnetic stirrer at 700 rpm and the autoclave was heated to 70 C. When the autoclave temperature reached the reaction temperature of 70 C, 10 g of an aqueous hydrogen peroxide solution (35 weight-% in water) was pumped into autoclave. After the addition of hydrogen peroxide the reaction mixture was continuously stirred for 5 hours. Subsequently, the autoclave was opened and the catalyst was removed by filtration and the reaction mixture was analyzed by GC and GC-MS. The conversion rates of DCDPSO and the selectivity for DCDPS (4,4'-Dichlorodiphenylsulfone) in % obtained for Example 5 are summarized in Table 1 below. The conversion and selectivity were calculated according to the formulas indicated below Table 1 based on a GC analysis. A 30 m CP Sil 8 column with an internal diameter of 0.25 mm ID was used for analysis.
With dihydrogen peroxide; acetic acid; at 80℃; for 1h; (3) Then dissolve it in glacial acetic acid, add hydrogen peroxide to carry out oxidation reaction, the oxidation reaction temperature is 80 C, the oxidation time is 1 h, after the reaction is completed, the temperature is cooled and filtered, and filtered.4,4'-dichlorodiphenyl sulfone is obtained; the catalyst used is a mixture of anhydrous aluminum trichloride and benzyl triethyl ammonium chloride.The prepared 4,4'-dichlorodiphenyl sulfone had a purity of 99.8% and a refined yield of 92.8%.

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[11]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1986,vol. 25,p. 678 - 680
[12]Journal of the Indian Chemical Society,1992,vol. 69,p. 819 - 821
[13]Journal of Organic Chemistry,1993,vol. 58,p. 5055 - 5059
[14]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 250 - 252
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[16]Tetrahedron,2001,vol. 57,p. 1369 - 1374
[17]Journal of Chemical Research, Miniprint,2000,p. 1118 - 1133
[18]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2005,vol. 44,p. 71 - 75
[19]Journal of the Indian Chemical Society,2007,vol. 84,p. 679 - 682
[20]Patent: WO2014/191475,2014,A1 .Location in patent: Page/Page column 34-35
[21]Patent: CN109851537,2019,A .Location in patent: Paragraph 0017; 0020; 0021; 0022; 0025; 0026
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