DE1225167B - Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone - Google Patents
Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer SulfoneInfo
- Publication number
- DE1225167B DE1225167B DEC35532A DEC0035532A DE1225167B DE 1225167 B DE1225167 B DE 1225167B DE C35532 A DEC35532 A DE C35532A DE C0035532 A DEC0035532 A DE C0035532A DE 1225167 B DE1225167 B DE 1225167B
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- aliphatic
- organic
- reaction
- sulfones
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 125000001931 aliphatic group Chemical group 0.000 title claims description 4
- 125000003118 aryl group Chemical group 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 12
- 150000003568 thioethers Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000003462 sulfoxides Chemical class 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 benzoic peracid Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- QBAQOCDXTIIQOF-UHFFFAOYSA-N 1-chloro-2-hydroperoxy-2-methylpropane Chemical compound ClCC(C)(C)OO QBAQOCDXTIIQOF-UHFFFAOYSA-N 0.000 description 1
- QEEPPWQOVJWUBC-UHFFFAOYSA-N 1-hydroperoxycyclohexene Chemical compound OOC1=CCCCC1 QEEPPWQOVJWUBC-UHFFFAOYSA-N 0.000 description 1
- QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WKEZHBQACHILEC-UHFFFAOYSA-N molybdenum(3+) Chemical compound [Mo+3] WKEZHBQACHILEC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 1
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 1
- 229940041260 vanadyl sulfate Drugs 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC35532A DE1225167B (de) | 1965-04-07 | 1965-04-07 | Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone |
| US535728A US3449439A (en) | 1965-04-07 | 1966-03-21 | Process for the production of sulfones from sulfides and sulfoxides |
| FR54779A FR1471966A (fr) | 1965-04-07 | 1966-03-24 | Procédé de préparation de sulfones à partir de sulfures et de sulfoxydes |
| GB15232/66A GB1135636A (en) | 1965-04-07 | 1966-04-06 | Process for the production of sulphones from sulphides and sulphoxides |
| BE679240D BE679240A (forum.php) | 1965-04-07 | 1966-04-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC35532A DE1225167B (de) | 1965-04-07 | 1965-04-07 | Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1225167B true DE1225167B (de) | 1966-09-22 |
Family
ID=7021858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC35532A Pending DE1225167B (de) | 1965-04-07 | 1965-04-07 | Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3449439A (forum.php) |
| BE (1) | BE679240A (forum.php) |
| DE (1) | DE1225167B (forum.php) |
| GB (1) | GB1135636A (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446227A (en) * | 1993-09-07 | 1995-08-29 | Phillips Petroleum Company | Co-production of an alkenyl aromatic compound or precursor thereof and an oxygenated sulfur-containing compound |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4287366A (en) * | 1980-03-10 | 1981-09-01 | Mitsui Toatsu Chemicals, Inc. | Process for preparing bisphenol sulfone derivatives |
| DE3733504A1 (de) * | 1987-10-03 | 1989-04-13 | Hoechst Ag | Bis-oxethylsulfonylmethyl-aniline und verfahren zu ihrer herstellung |
| US5274139A (en) * | 1993-02-26 | 1993-12-28 | University Of Florida | Method for effective reaction between oxygen and organic substance utilizing regenerable hydroperioxide oxidant |
| FR2818547B1 (fr) * | 2000-12-22 | 2006-11-17 | Oreal | Nouveaux derives c-glycosides et utilisation |
| JP4881297B2 (ja) * | 2004-05-28 | 2012-02-22 | フォーエスシー アクチエンゲゼルシャフト | 新規のテトラヒドロピリドチオフェン |
| CN1960987A (zh) * | 2004-06-02 | 2007-05-09 | 奥坦纳医药公司 | 制备吡啶－2－基甲基亚磺酰基－1h－苯并咪唑类化合物的方法 |
| DE602005007220D1 (de) * | 2004-06-04 | 2008-07-10 | Nycomed Gmbh | Tetrahydropyridothiophenen zur verwendung in der behandlung von krebs |
| US20090209534A1 (en) * | 2004-06-11 | 2009-08-20 | Klaus Pekari | Novel compounds and use of tetrahydropyridopyridothiophenes |
| EP1758655A2 (en) * | 2004-06-11 | 2007-03-07 | Altana Pharma AG | Tetrahydropyridothiophenes for treating hyperproliferative disorders |
| CA2596202A1 (en) | 2005-02-09 | 2006-08-17 | Altana Pharma Ag | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| US20090252706A1 (en) * | 2005-02-11 | 2009-10-08 | Klaus Pekari | Tetrahydropyridothiophenes As Antripoliferative Agents For The Treatment Of Cancer |
| AU2006212179A1 (en) * | 2005-02-11 | 2006-08-17 | 4Sc Ag | Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer |
| WO2006125815A2 (en) * | 2005-05-25 | 2006-11-30 | Nycomed Gmbh | Tetrahydropyridothiophenes for use in the treatment of cancer |
| CA2609003A1 (en) * | 2005-05-25 | 2006-11-30 | Nycomed Gmbh | Tetrahydropyridothiophenes for use in the treatment of cancer |
| RU2291859C1 (ru) * | 2005-09-20 | 2007-01-20 | Виль Ришатович Нигматуллин | Способ окисления сульфидов нефти |
| ES2326110B1 (es) * | 2007-12-14 | 2010-07-05 | Universidad De Burgos | Procedimiento de oxidacion aerobica de un grupo sulfoxido a sulfona. |
| KR20160016897A (ko) * | 2013-05-29 | 2016-02-15 | 바스프 에스이 | 설폭사이드의 산화 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL106984C (forum.php) * | 1957-05-24 |
-
1965
- 1965-04-07 DE DEC35532A patent/DE1225167B/de active Pending
-
1966
- 1966-03-21 US US535728A patent/US3449439A/en not_active Expired - Lifetime
- 1966-04-06 GB GB15232/66A patent/GB1135636A/en not_active Expired
- 1966-04-07 BE BE679240D patent/BE679240A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446227A (en) * | 1993-09-07 | 1995-08-29 | Phillips Petroleum Company | Co-production of an alkenyl aromatic compound or precursor thereof and an oxygenated sulfur-containing compound |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1135636A (en) | 1968-12-04 |
| BE679240A (forum.php) | 1966-09-16 |
| US3449439A (en) | 1969-06-10 |
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