ES2899156T3 - Proceso para producir sulfóxido de 4,4`-diclorodifenilo - Google Patents
Proceso para producir sulfóxido de 4,4`-diclorodifenilo Download PDFInfo
- Publication number
- ES2899156T3 ES2899156T3 ES20702806T ES20702806T ES2899156T3 ES 2899156 T3 ES2899156 T3 ES 2899156T3 ES 20702806 T ES20702806 T ES 20702806T ES 20702806 T ES20702806 T ES 20702806T ES 2899156 T3 ES2899156 T3 ES 2899156T3
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- Spain
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- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 69
- 230000008569 process Effects 0.000 title claims abstract description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 116
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 101
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 98
- 239000002904 solvent Substances 0.000 claims abstract description 98
- 239000012074 organic phase Substances 0.000 claims abstract description 94
- 238000001816 cooling Methods 0.000 claims abstract description 87
- 239000007788 liquid Substances 0.000 claims abstract description 84
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 73
- 238000000926 separation method Methods 0.000 claims abstract description 53
- 239000000725 suspension Substances 0.000 claims abstract description 41
- 239000008346 aqueous phase Substances 0.000 claims abstract description 33
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 31
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 28
- 239000007787 solid Substances 0.000 claims abstract description 27
- KJGYFISADIZFEL-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfinylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)C1=CC=C(Cl)C=C1 KJGYFISADIZFEL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000002156 mixing Methods 0.000 claims abstract description 15
- 238000002425 crystallisation Methods 0.000 claims description 54
- 230000008025 crystallization Effects 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 238000004821 distillation Methods 0.000 claims description 34
- 238000001704 evaporation Methods 0.000 claims description 31
- 239000012452 mother liquor Substances 0.000 claims description 27
- 230000008020 evaporation Effects 0.000 claims description 26
- 238000009835 boiling Methods 0.000 claims description 17
- 239000010413 mother solution Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 3
- 239000011550 stock solution Substances 0.000 abstract description 25
- 238000005406 washing Methods 0.000 description 77
- 238000001914 filtration Methods 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000012065 filter cake Substances 0.000 description 55
- 238000006460 hydrolysis reaction Methods 0.000 description 43
- 230000007062 hydrolysis Effects 0.000 description 41
- 239000013078 crystal Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000012535 impurity Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000005191 phase separation Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- -1 diaryl sulfides Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000007345 electrophilic aromatic substitution reaction Methods 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QNCBCEFSWSBMHM-UHFFFAOYSA-N 1-chloro-2-(4-chlorophenyl)sulfinylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)C1=CC=CC=C1Cl QNCBCEFSWSBMHM-UHFFFAOYSA-N 0.000 description 2
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- JAYCNKDKIKZTAF-UHFFFAOYSA-N 1-chloro-2-(2-chlorophenyl)benzene Chemical group ClC1=CC=CC=C1C1=CC=CC=C1Cl JAYCNKDKIKZTAF-UHFFFAOYSA-N 0.000 description 1
- MJEPOVIWHVRBIT-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=C(Cl)C=C1 MJEPOVIWHVRBIT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 238000004483 ATR-FTIR spectroscopy Methods 0.000 description 1
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 1
- 229920007925 Ethylene chlorotrifluoroethylene (ECTFE) Polymers 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000002320 enamel (paints) Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920012287 polyphenylene sulfone Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- LIRMPIXWGWLNND-UHFFFAOYSA-N selenium oxydichloride Chemical compound Cl[Se](Cl)=O LIRMPIXWGWLNND-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962803045P | 2019-02-08 | 2019-02-08 | |
| EP19156196 | 2019-02-08 | ||
| PCT/EP2020/052970 WO2020161228A1 (en) | 2019-02-08 | 2020-02-06 | Process for producing 4,4`-dichlorodiphenyl sulfoxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2899156T3 true ES2899156T3 (es) | 2022-03-10 |
Family
ID=69400574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES20702806T Active ES2899156T3 (es) | 2019-02-08 | 2020-02-06 | Proceso para producir sulfóxido de 4,4`-diclorodifenilo |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US12168642B2 (https=) |
| EP (1) | EP3774726B1 (https=) |
| JP (1) | JP2022520199A (https=) |
| KR (1) | KR20210125493A (https=) |
| CN (1) | CN113474329B (https=) |
| ES (1) | ES2899156T3 (https=) |
| WO (1) | WO2020161228A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022520769A (ja) * | 2019-02-08 | 2022-04-01 | ビーエーエスエフ ソシエタス・ヨーロピア | ４，４’－ジクロロジフェニルスルホキシド結晶（ｃ）を含む結晶組成物（ｃｃ） |
| CN117326990B (zh) * | 2023-09-28 | 2025-09-19 | 山东产研高性能材料技术研究院有限公司 | 一种4,4’-二氯二苯亚砜的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5110459A (en) * | 1974-07-13 | 1976-01-27 | Kimura Kakoki Co Ltd | Bunshukukio jusuru shinkureikyakusochi |
| SU765262A1 (ru) * | 1977-12-30 | 1980-09-23 | Всесоюзный Научно-Исследовательский И Проектный Институт Мономеров | Способ получени 4,4 -дихлордифенилсульфона |
| DE3704932A1 (de) * | 1987-02-17 | 1988-09-01 | Basf Ag | Verfahren zur herstellung von 4,4'-dichlordiphenylsulfon |
| EP0943608A1 (en) * | 1998-03-20 | 1999-09-22 | Dsm N.V. | Process for the continuous purification of crude epsilon--caprolactam |
| JP3864563B2 (ja) * | 1998-06-11 | 2007-01-10 | 三井化学株式会社 | 高純度テレフタル酸の製造方法 |
| JP2003210942A (ja) * | 2002-01-25 | 2003-07-29 | Meiko:Kk | 有機塩素化合物の脱塩素化方法及び脱塩化装置 |
| CN102459621B (zh) * | 2009-06-05 | 2015-01-28 | 赢创德固赛有限公司 | 制备2-酮羧酸的方法 |
| CN102351757A (zh) | 2011-08-25 | 2012-02-15 | 吴江市北厍盛源纺织品助剂厂 | 采用亚砜氧化制备4.4–二氯二苯砜的方法 |
| CN102351756A (zh) | 2011-08-25 | 2012-02-15 | 吴江市北厍盛源纺织品助剂厂 | 改进的4.4–二氯二苯砜制备方法 |
| CN102351758A (zh) | 2011-08-25 | 2012-02-15 | 吴江市北厍盛源纺织品助剂厂 | 4.4–二氯二苯砜的新制备方法 |
| CN104402780B (zh) * | 2014-12-12 | 2016-04-27 | 山东凯盛新材料有限公司 | 4,4’-二氯二苯砜的合成工艺 |
| CN104557626A (zh) | 2014-12-12 | 2015-04-29 | 山东凯盛新材料有限公司 | 亚砜氧化法制备4,4′-二氯二苯砜的工艺 |
| CN108047101A (zh) | 2017-12-07 | 2018-05-18 | 九江中星医药化工有限公司 | 一种高效连续生产4,4-二氯二苯砜的合成工艺 |
| JP2022545831A (ja) * | 2019-08-27 | 2022-10-31 | ビーエーエスエフ ソシエタス・ヨーロピア | ４，４’－ジクロロジフェニルスルホンを製造するための方法 |
-
2020
- 2020-02-06 US US17/429,210 patent/US12168642B2/en active Active
- 2020-02-06 CN CN202080013163.7A patent/CN113474329B/zh not_active Expired - Fee Related
- 2020-02-06 WO PCT/EP2020/052970 patent/WO2020161228A1/en not_active Ceased
- 2020-02-06 EP EP20702806.9A patent/EP3774726B1/en active Active
- 2020-02-06 ES ES20702806T patent/ES2899156T3/es active Active
- 2020-02-06 KR KR1020217025083A patent/KR20210125493A/ko not_active Abandoned
- 2020-02-06 JP JP2021546723A patent/JP2022520199A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2022520199A (ja) | 2022-03-29 |
| CN113474329B (zh) | 2024-09-20 |
| US20220098147A1 (en) | 2022-03-31 |
| US12168642B2 (en) | 2024-12-17 |
| EP3774726A1 (en) | 2021-02-17 |
| CN113474329A (zh) | 2021-10-01 |
| KR20210125493A (ko) | 2021-10-18 |
| WO2020161228A1 (en) | 2020-08-13 |
| EP3774726B1 (en) | 2021-08-25 |
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