DE10018580A1 - Semikontinuierliches Verfahren zur Herstellung von 4,4'-Dihydroxydiphenylsulfon - Google Patents
Semikontinuierliches Verfahren zur Herstellung von 4,4'-DihydroxydiphenylsulfonInfo
- Publication number
- DE10018580A1 DE10018580A1 DE10018580A DE10018580A DE10018580A1 DE 10018580 A1 DE10018580 A1 DE 10018580A1 DE 10018580 A DE10018580 A DE 10018580A DE 10018580 A DE10018580 A DE 10018580A DE 10018580 A1 DE10018580 A1 DE 10018580A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- phenol
- product
- crude product
- net
- 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.)
- Withdrawn
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 56
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 54
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 12
- 239000012043 crude product Substances 0.000 title claims abstract description 12
- 239000000725 suspension Substances 0.000 title claims abstract description 8
- 238000010924 continuous production Methods 0.000 title claims abstract description 7
- 239000000047 product Substances 0.000 claims abstract description 26
- 239000002699 waste material Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 238000001953 recrystallisation Methods 0.000 claims description 6
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229940044654 phenolsulfonic acid Drugs 0.000 claims description 5
- 150000003457 sulfones Chemical class 0.000 claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 238000004064 recycling Methods 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000012452 mother liquor Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006317 isomerization reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- -1 2,4'-dihydroxydiphenyl sulfone Chemical class 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000694408 Isomeris Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000004886 process control Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LROZSPADHSXFJA-UHFFFAOYSA-N 2-(4-hydroxyphenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=CC=C1O LROZSPADHSXFJA-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011083 clear filtration Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10018580A DE10018580A1 (de) | 2000-04-14 | 2000-04-14 | Semikontinuierliches Verfahren zur Herstellung von 4,4'-Dihydroxydiphenylsulfon |
| EP01927904A EP1272462B1 (de) | 2000-04-14 | 2001-04-10 | Semikontinuierliches verfahren zur herstellung von 4,4'-dihydroxydiphenylsulfon |
| JP2001576765A JP4637438B2 (ja) | 2000-04-14 | 2001-04-10 | ４，４’−ジヒドロキシジフェニルスルホンの半連続的製造法 |
| US10/257,328 US6700020B2 (en) | 2000-04-14 | 2001-04-10 | Semi-continuous method for producing 4,4'-dihydroxydiphenyl sulfone |
| DE50108671T DE50108671D1 (de) | 2000-04-14 | 2001-04-10 | Semikontinuierliches verfahren zur herstellung von 4,4'-dihydroxydiphenylsulfon |
| AU54801/01A AU5480101A (en) | 2000-04-14 | 2001-04-10 | Semi-continuous method for producing 4,4'-dihydroxydiphenylsulfone |
| PCT/EP2001/004081 WO2001079163A1 (de) | 2000-04-14 | 2001-04-10 | Semikontinuierliches verfahren zur herstellung von 4,4'-dihydroxydiphenylsulfon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10018580A DE10018580A1 (de) | 2000-04-14 | 2000-04-14 | Semikontinuierliches Verfahren zur Herstellung von 4,4'-Dihydroxydiphenylsulfon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10018580A1 true DE10018580A1 (de) | 2001-10-25 |
Family
ID=7638782
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10018580A Withdrawn DE10018580A1 (de) | 2000-04-14 | 2000-04-14 | Semikontinuierliches Verfahren zur Herstellung von 4,4'-Dihydroxydiphenylsulfon |
| DE50108671T Expired - Lifetime DE50108671D1 (de) | 2000-04-14 | 2001-04-10 | Semikontinuierliches verfahren zur herstellung von 4,4'-dihydroxydiphenylsulfon |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50108671T Expired - Lifetime DE50108671D1 (de) | 2000-04-14 | 2001-04-10 | Semikontinuierliches verfahren zur herstellung von 4,4'-dihydroxydiphenylsulfon |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6700020B2 (https=) |
| EP (1) | EP1272462B1 (https=) |
| JP (1) | JP4637438B2 (https=) |
| AU (1) | AU5480101A (https=) |
| DE (2) | DE10018580A1 (https=) |
| WO (1) | WO2001079163A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1498412B1 (en) * | 2002-04-25 | 2014-06-25 | Konishi Chemical Ind. Co., Ltd. | Process for producing dihydroxydiphenyl sulfone |
| JP4496381B2 (ja) * | 2002-09-25 | 2010-07-07 | 小西化学工業株式会社 | 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 |
| KR101354910B1 (ko) * | 2005-04-07 | 2014-01-22 | 에이.와이.와이.티. 테크놀로지컬 어플리케이션즈 앤드 데이타 업데이트 리미티드 | 무기 풀러렌-유사 나노입자의 제조 공정 및 제조장치 |
| CN113480457B (zh) * | 2021-07-23 | 2022-04-15 | 涉县津东经贸有限责任公司 | 一种高纯度双酚s的生产方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297766A (en) | 1961-10-02 | 1967-01-10 | Dow Chemical Co | Semi-continuous process for preparing 4, 4'-sulfonyldiphenol |
| EP0220004B1 (en) | 1985-10-04 | 1990-04-11 | Amoco Corporation | Process for synthesizing 4,4'-dihydroxydiphenyl sulfone |
| ATE48595T1 (de) * | 1985-10-04 | 1989-12-15 | Amoco Corp | Verfahren zur rueckgewinnung von 4,4'dihydroxydiphenylsulfonaus einer isomermischung. |
| GB8801611D0 (en) * | 1988-01-25 | 1988-02-24 | Ici Plc | Preparation of 4 4'-dihydroxydiphenyl sulphone |
| DE3928704A1 (de) * | 1989-08-30 | 1991-03-07 | Hoechst Ag | Verfahren zur herstellung von 4,4' -dihydroxydiphenylsulfon |
| JPH0791261B2 (ja) * | 1989-09-14 | 1995-10-04 | 小西化学工業株式会社 | ４，４′―ジヒドロキシジフェニルスルホンの製造法 |
| JPH082861B2 (ja) * | 1989-12-29 | 1996-01-17 | 小西化学工業株式会社 | 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 |
| WO1992002493A1 (en) | 1990-08-06 | 1992-02-20 | Aristech Chemical Corporation | Preparation of relatively pure p, p-bisphenol s |
| JP2641023B2 (ja) * | 1993-07-16 | 1997-08-13 | 日華化学株式会社 | ４，４’−ジヒドロキシジフェニルスルホンの精製方法 |
-
2000
- 2000-04-14 DE DE10018580A patent/DE10018580A1/de not_active Withdrawn
-
2001
- 2001-04-10 DE DE50108671T patent/DE50108671D1/de not_active Expired - Lifetime
- 2001-04-10 JP JP2001576765A patent/JP4637438B2/ja not_active Expired - Lifetime
- 2001-04-10 US US10/257,328 patent/US6700020B2/en not_active Expired - Lifetime
- 2001-04-10 WO PCT/EP2001/004081 patent/WO2001079163A1/de not_active Ceased
- 2001-04-10 AU AU54801/01A patent/AU5480101A/en not_active Abandoned
- 2001-04-10 EP EP01927904A patent/EP1272462B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4637438B2 (ja) | 2011-02-23 |
| US20030149308A1 (en) | 2003-08-07 |
| WO2001079163A1 (de) | 2001-10-25 |
| EP1272462B1 (de) | 2006-01-11 |
| US6700020B2 (en) | 2004-03-02 |
| JP2003531137A (ja) | 2003-10-21 |
| DE50108671D1 (de) | 2006-04-06 |
| EP1272462A1 (de) | 2003-01-08 |
| AU5480101A (en) | 2001-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |