KR20210126007A - 4,4'-디클로로디페닐 술폭시드의 수득 방법 - Google Patents
4,4'-디클로로디페닐 술폭시드의 수득 방법 Download PDFInfo
- Publication number
- KR20210126007A KR20210126007A KR1020217024742A KR20217024742A KR20210126007A KR 20210126007 A KR20210126007 A KR 20210126007A KR 1020217024742 A KR1020217024742 A KR 1020217024742A KR 20217024742 A KR20217024742 A KR 20217024742A KR 20210126007 A KR20210126007 A KR 20210126007A
- Authority
- KR
- South Korea
- Prior art keywords
- range
- dcdpso
- cooling
- solvent
- pressure
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 57
- 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 title claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 127
- 238000001816 cooling Methods 0.000 claims abstract description 94
- 239000000203 mixture Substances 0.000 claims abstract description 87
- 239000002904 solvent Substances 0.000 claims abstract description 76
- 239000012452 mother liquor Substances 0.000 claims abstract description 61
- 230000008569 process Effects 0.000 claims abstract description 43
- 239000000725 suspension Substances 0.000 claims abstract description 39
- 238000000926 separation method Methods 0.000 claims abstract description 37
- 239000007787 solid Substances 0.000 claims abstract description 22
- 238000004064 recycling Methods 0.000 claims abstract description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 72
- 238000002425 crystallisation Methods 0.000 claims description 62
- 230000008025 crystallization Effects 0.000 claims description 62
- 238000001704 evaporation Methods 0.000 claims description 29
- 238000004821 distillation Methods 0.000 claims description 27
- 230000008020 evaporation Effects 0.000 claims description 24
- 238000009835 boiling Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 76
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 60
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 41
- 230000007062 hydrolysis Effects 0.000 description 32
- 238000006460 hydrolysis reaction Methods 0.000 description 32
- 238000001914 filtration Methods 0.000 description 31
- 238000005406 washing Methods 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 26
- 239000007795 chemical reaction product Substances 0.000 description 25
- 239000013078 crystal Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- 238000002156 mixing Methods 0.000 description 11
- 238000005191 phase separation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 8
- 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 7
- 239000012065 filter cake Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 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 4
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000007345 electrophilic aromatic substitution reaction Methods 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 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
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000376 reactant Substances 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
- 239000000126 substance Substances 0.000 description 2
- 238000005496 tempering Methods 0.000 description 2
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 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
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- -1 diaryl sulfides Chemical class 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
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002917 insecticide 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
- 238000002955 isolation Methods 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000178 monomer Substances 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
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000021715 photosynthesis, light harvesting Effects 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920012287 polyphenylene sulfone Polymers 0.000 description 1
- 239000011148 porous material Substances 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
- 230000000717 retained effect Effects 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
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19156178.6 | 2019-02-08 | ||
| EP19156178 | 2019-02-08 | ||
| PCT/EP2020/052968 WO2020161226A1 (en) | 2019-02-08 | 2020-02-06 | A process for obtaining 4,4'-dichlorodiphenyl sulfoxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20210126007A true KR20210126007A (ko) | 2021-10-19 |
Family
ID=65365845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020217024742A Abandoned KR20210126007A (ko) | 2019-02-08 | 2020-02-06 | 4,4'-디클로로디페닐 술폭시드의 수득 방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20220135522A1 (https=) |
| EP (1) | EP3921303A1 (https=) |
| JP (1) | JP2022520200A (https=) |
| KR (1) | KR20210126007A (https=) |
| CN (1) | CN113454061A (https=) |
| WO (1) | WO2020161226A1 (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） |
| WO2021037682A1 (en) * | 2019-08-27 | 2021-03-04 | Basf Se | A process for purifying crude 4,4'-dichlorodiphenyl sulfone |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618582A (en) * | 1948-11-01 | 1952-11-18 | Union Oil Co | Pest control |
| SU765262A1 (ru) | 1977-12-30 | 1980-09-23 | Всесоюзный Научно-Исследовательский И Проектный Институт Мономеров | Способ получени 4,4 -дихлордифенилсульфона |
| RU2158257C1 (ru) * | 1999-12-10 | 2000-10-27 | Институт элементоорганических соединений им. А.Н. Несмеянова РАН | Способ получения 4,4'-дихлордифенилсульфоксида |
| RU2159764C1 (ru) * | 1999-12-10 | 2000-11-27 | Институт элементоорганических соединений им. А.Н. Несмеянова РАН | Способ получения 4,4'-дихлордифенилсульфоксида |
| WO2004029020A1 (ja) * | 2002-09-25 | 2004-04-08 | Konishi Chemical Ind. Co., Ltd. | 高純度4,4'−ジヒドロキシジフェニルスルホンの製造方法 |
| 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 |
| 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 |
| 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 |
-
2020
- 2020-02-06 KR KR1020217024742A patent/KR20210126007A/ko not_active Abandoned
- 2020-02-06 CN CN202080012853.0A patent/CN113454061A/zh active Pending
- 2020-02-06 US US17/429,028 patent/US20220135522A1/en not_active Abandoned
- 2020-02-06 JP JP2021546724A patent/JP2022520200A/ja not_active Withdrawn
- 2020-02-06 EP EP20702659.2A patent/EP3921303A1/en not_active Withdrawn
- 2020-02-06 WO PCT/EP2020/052968 patent/WO2020161226A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20220135522A1 (en) | 2022-05-05 |
| EP3921303A1 (en) | 2021-12-15 |
| JP2022520200A (ja) | 2022-03-29 |
| CN113454061A (zh) | 2021-09-28 |
| WO2020161226A1 (en) | 2020-08-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20210804 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1902 | Submission of document of abandonment before decision of registration |