JPH01113362A - ビス‐オキシエチルスルホニルメチル‐アニリン及びその製法 - Google Patents
ビス‐オキシエチルスルホニルメチル‐アニリン及びその製法Info
- Publication number
- JPH01113362A JPH01113362A JP63242650A JP24265088A JPH01113362A JP H01113362 A JPH01113362 A JP H01113362A JP 63242650 A JP63242650 A JP 63242650A JP 24265088 A JP24265088 A JP 24265088A JP H01113362 A JPH01113362 A JP H01113362A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- bis
- formulas
- chains
- oxyethylsulfonylmethyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims abstract description 12
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims abstract description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011230 binding agent Substances 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
- -1 tungsten (VI) compound Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 claims description 4
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims description 4
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000985 reactive dye Substances 0.000 abstract description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract description 2
- 125000006839 xylylene group Chemical group 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- OGINYETXPCHSPB-UHFFFAOYSA-N 1-nitro-2-(sulfonylmethyl)benzene Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C=S(=O)=O OGINYETXPCHSPB-UHFFFAOYSA-N 0.000 abstract 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- ALOFYNWIXJYYGX-UHFFFAOYSA-N sulfonylmethylbenzene Chemical compound O=S(=O)=CC1=CC=CC=C1 ALOFYNWIXJYYGX-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000006396 nitration reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000005352 clarification Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- GRJWOKACBGZOKT-UHFFFAOYSA-N 1,3-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC(CCl)=C1 GRJWOKACBGZOKT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- TVFFHYVZRRVAGJ-UHFFFAOYSA-N 1,3-bis(chloromethyl)-2-methyl-5-nitrobenzene Chemical compound CC1=C(CCl)C=C([N+]([O-])=O)C=C1CCl TVFFHYVZRRVAGJ-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- 101100178313 Aedes aegypti HP-I gene Proteins 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 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
- SHIYKHFFMRDJJC-UHFFFAOYSA-L [Na+].[Na+].[O-]O[O-] Chemical compound [Na+].[Na+].[O-]O[O-] SHIYKHFFMRDJJC-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3733504.9 | 1987-10-03 | ||
| DE19873733504 DE3733504A1 (de) | 1987-10-03 | 1987-10-03 | Bis-oxethylsulfonylmethyl-aniline und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01113362A true JPH01113362A (ja) | 1989-05-02 |
Family
ID=6337576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63242650A Pending JPH01113362A (ja) | 1987-10-03 | 1988-09-29 | ビス‐オキシエチルスルホニルメチル‐アニリン及びその製法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4960940A (en, 2012) |
| EP (1) | EP0310944B1 (en, 2012) |
| JP (1) | JPH01113362A (en, 2012) |
| KR (1) | KR890006580A (en, 2012) |
| DE (2) | DE3733504A1 (en, 2012) |
| IN (1) | IN171542B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0414637A1 (de) * | 1989-08-23 | 1991-02-27 | Ciba-Geigy Ag | Verfahren zur Herstellung von aromatischen Aminen |
| US5166441A (en) * | 1990-12-12 | 1992-11-24 | Neurosearch A/S | Astaxanthin intermediates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB931595A (en) * | 1959-12-08 | 1963-07-17 | Gen Aniline & Film Corp | Aminobenzyl sulfonylethanol compounds |
| US3201434A (en) * | 1960-11-25 | 1965-08-17 | Stevens & Co Inc J P | Di(beta ethylsulfonyl) salts |
| US3330855A (en) * | 1962-09-11 | 1967-07-11 | Nat Distillers Chem Corp | alpha, alpha'-bis(lauryl beta-thiopropionate)-p-xylene |
| DE1225167B (de) * | 1965-04-07 | 1966-09-22 | Huels Chemische Werke Ag | Verfahren zur Herstellung aliphatischer, aromatischer oder gemischt aliphatisch-aromatischer Sulfone |
| US4612394A (en) * | 1982-04-06 | 1986-09-16 | Sumitomo Chemical Company, Limited | Process for producing aminophenyl-β-hydroxyethylsulfone |
| DE3314565A1 (de) * | 1983-04-22 | 1984-10-25 | Wella Ag, 6100 Darmstadt | 1-methylsulfonymethoxy-2,4-diaminobenzol, verfahren zu dessen herstellung und diese verbindung enthaltende haarfaerbemittel |
| DE3423933A1 (de) * | 1984-06-29 | 1986-01-09 | Wella Ag, 6100 Darmstadt | 2-alkylsufonyl-1,4-diaminobenzole, verfahren zu ihrer herstellung sowie oxidationshaarfaerbemittel mit einem gehalt an diesen verbindungen |
| DE3441274A1 (de) * | 1984-11-12 | 1986-05-15 | Hoechst Ag, 6230 Frankfurt | Monocyclische bis-oxethylsulfonyl-benzole und verfahren zu ihrer herstellung |
-
1987
- 1987-10-03 DE DE19873733504 patent/DE3733504A1/de not_active Withdrawn
-
1988
- 1988-09-22 IN IN791/CAL/88A patent/IN171542B/en unknown
- 1988-09-29 EP EP88116094A patent/EP0310944B1/de not_active Expired - Lifetime
- 1988-09-29 US US07/251,469 patent/US4960940A/en not_active Expired - Fee Related
- 1988-09-29 JP JP63242650A patent/JPH01113362A/ja active Pending
- 1988-09-29 DE DE8888116094T patent/DE3877487D1/de not_active Expired - Fee Related
- 1988-09-30 KR KR1019880012731A patent/KR890006580A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0310944A3 (en) | 1990-01-10 |
| DE3877487D1 (de) | 1993-02-25 |
| US4960940A (en) | 1990-10-02 |
| DE3733504A1 (de) | 1989-04-13 |
| KR890006580A (ko) | 1989-06-14 |
| EP0310944A2 (de) | 1989-04-12 |
| EP0310944B1 (de) | 1993-01-13 |
| IN171542B (en, 2012) | 1992-11-14 |
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