DE2145725A1 - Verfahren zur Herstellung von Hydroxyarylthioäthern - Google Patents
Verfahren zur Herstellung von HydroxyarylthioäthernInfo
- Publication number
- DE2145725A1 DE2145725A1 DE19712145725 DE2145725A DE2145725A1 DE 2145725 A1 DE2145725 A1 DE 2145725A1 DE 19712145725 DE19712145725 DE 19712145725 DE 2145725 A DE2145725 A DE 2145725A DE 2145725 A1 DE2145725 A1 DE 2145725A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- sulfuric acid
- bisulfate
- formula
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 36
- -1 hydroxyaryl thioethers Chemical class 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 105
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000011541 reaction mixture Substances 0.000 claims description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- SFHKWYNBSBPMJE-UHFFFAOYSA-N chlorosulfanium hydrogen sulfate Chemical compound Cl[SH2+].OS([O-])(=O)=O SFHKWYNBSBPMJE-UHFFFAOYSA-N 0.000 claims description 17
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 16
- 229910017604 nitric acid Inorganic materials 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 31
- 238000006396 nitration reaction Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- VKZOVEZYVBWVAQ-UHFFFAOYSA-N hydrogen sulfate;phenylsulfanium Chemical compound OS([O-])(=O)=O.[SH2+]C1=CC=CC=C1 VKZOVEZYVBWVAQ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007789 gas Substances 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000003568 thioethers Chemical class 0.000 description 8
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- YALHCTUQSQRCSX-UHFFFAOYSA-N sulfane sulfuric acid Chemical compound S.OS(O)(=O)=O YALHCTUQSQRCSX-UHFFFAOYSA-N 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- KCENUYRNJCYPGI-UHFFFAOYSA-N hydrogen sulfate (4-hydroxy-3,5-dinitrophenyl)-dimethylsulfanium Chemical compound S([O-])(O)(=O)=O.OC1=C(C=C(C=C1[N+](=O)[O-])[S+](C)C)[N+](=O)[O-] KCENUYRNJCYPGI-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GYXGGOGKDIRPKH-UHFFFAOYSA-N OS([O-])(=O)=O.C[S+](C)C1=CC=C(O)C=C1 Chemical compound OS([O-])(=O)=O.C[S+](C)C1=CC=C(O)C=C1 GYXGGOGKDIRPKH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-O phenylsulfanium Chemical compound [SH2+]C1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-O 0.000 description 1
- OQFZBPZJXAVCAB-UHFFFAOYSA-N phenylsulfanium sulfate Chemical compound S(=O)(=O)([O-])[O-].C1(=CC=CC=C1)[SH2+].C1(=CC=CC=C1)[SH2+] OQFZBPZJXAVCAB-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7216370A | 1970-09-14 | 1970-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2145725A1 true DE2145725A1 (de) | 1972-03-16 |
Family
ID=22105982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712145725 Withdrawn DE2145725A1 (de) | 1970-09-14 | 1971-09-13 | Verfahren zur Herstellung von Hydroxyarylthioäthern |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3732317A (enExample) |
| JP (1) | JPS5652016B1 (enExample) |
| AU (1) | AU463624B2 (enExample) |
| CA (1) | CA981694A (enExample) |
| CH (1) | CH572907A5 (enExample) |
| DE (1) | DE2145725A1 (enExample) |
| FR (1) | FR2107600A5 (enExample) |
| GB (1) | GB1351957A (enExample) |
| IT (1) | IT938815B (enExample) |
| NL (1) | NL173396C (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2644591A1 (de) * | 1976-10-02 | 1978-04-06 | Bayer Ag | Verfahren zur herstellung von arylsulfoniumsalzen |
-
1970
- 1970-09-14 US US00072163A patent/US3732317A/en not_active Expired - Lifetime
-
1971
- 1971-09-13 GB GB4248371A patent/GB1351957A/en not_active Expired
- 1971-09-13 IT IT28571/71A patent/IT938815B/it active
- 1971-09-13 CA CA122,696A patent/CA981694A/en not_active Expired
- 1971-09-13 AU AU33407/71A patent/AU463624B2/en not_active Expired
- 1971-09-13 FR FR7132918A patent/FR2107600A5/fr not_active Expired
- 1971-09-13 DE DE19712145725 patent/DE2145725A1/de not_active Withdrawn
- 1971-09-13 NL NLAANVRAGE7112537,A patent/NL173396C/xx not_active IP Right Cessation
- 1971-09-13 CH CH1337871A patent/CH572907A5/xx not_active IP Right Cessation
- 1971-09-13 JP JP7046671A patent/JPS5652016B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5652016B1 (enExample) | 1981-12-09 |
| FR2107600A5 (enExample) | 1972-05-05 |
| CA981694A (en) | 1976-01-13 |
| NL7112537A (enExample) | 1972-03-16 |
| IT938815B (it) | 1973-02-10 |
| CH572907A5 (enExample) | 1976-02-27 |
| NL173396B (nl) | 1983-08-16 |
| AU3340771A (en) | 1973-03-22 |
| US3732317A (en) | 1973-05-08 |
| GB1351957A (en) | 1974-05-15 |
| NL173396C (nl) | 1984-01-16 |
| AU463624B2 (en) | 1975-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0294685B1 (de) | Verfahren zur Herstellung von Chinolinen | |
| DE69636402T2 (de) | Reagenz und Verfahren zur Synthese von organischen oxysulfierten und fluorinierten Derivaten | |
| CH624665A5 (enExample) | ||
| DE2620791A1 (de) | Verfahren zur herstellung von diaryl- oder heteroarylverbindungen | |
| DE2145725A1 (de) | Verfahren zur Herstellung von Hydroxyarylthioäthern | |
| DE69508864T2 (de) | Verfahren zur Herstellung von Pikrinsaüre | |
| DE2922688C2 (de) | Verfahren zur Nitrosierung von Phenolen zu Benzochinonoximen | |
| DE2105473B2 (enExample) | ||
| DE69707008T2 (de) | Synthese von jodpropargylcarbamat in wässriger lösung | |
| DE2839053A1 (de) | Verfahren zur herstellung von p-hydroxybenzaldehyd | |
| DE69413803T2 (de) | Verfahren zur herstellung von diazomethanderivaten | |
| DE1810164A1 (de) | Hydrazinderivate und Verfahren zur Herstellung derselben | |
| DE2519315C2 (de) | Verfahren zur Herstellung von 3-Trichlormethyl-5-chlor-1,2,4-thiadiazol | |
| DE1275540B (de) | Verfahren zur Herstellung von Hydroxyarylsulfoniumchloriden | |
| EP1110939B1 (de) | Verfahren zur Herstellung von Poly(fluoralkyl)-acetophenonen | |
| EP0003774A1 (de) | Verfahren zur Nitrierung von aromatischen Sulfonsäuren | |
| AT239243B (de) | Verfahren zur Herstellung von 2, 3-Dicyan-1, 4-dithia-anthrahydrochinon und -anthrachinon | |
| DE3802372A1 (de) | Neue fluorbenzophenone und fluorbenzoesaeurefluorphenylester sowie verfahren zu ihrer herstellung | |
| CH624668A5 (enExample) | ||
| DE2147610A1 (de) | 2,6 Dimtro aniline | |
| CH443349A (de) | Verfahren zur Herstellung von 2,3-Dicyan-1,4-dithia-anthrachinon | |
| DE804572C (de) | Verfahren zur Herstellung von Sulfensaeurehalogeniden | |
| DE3519864A1 (de) | Verfahren zur herstellung von o- und p-nitrobenzaldehyd | |
| DE2231157A1 (de) | Verfahren zur nitrierung von phenolverbindungen | |
| DE1543781C3 (de) | Verfahren zur Herstellung von Alkylarylaminen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |