CH628607A5 - Process for preparing chloroanthraquinones - Google Patents
Process for preparing chloroanthraquinones Download PDFInfo
- Publication number
- CH628607A5 CH628607A5 CH1460277A CH1460277A CH628607A5 CH 628607 A5 CH628607 A5 CH 628607A5 CH 1460277 A CH1460277 A CH 1460277A CH 1460277 A CH1460277 A CH 1460277A CH 628607 A5 CH628607 A5 CH 628607A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorine
- nitroanthraquinone
- reaction
- dinitroanthraquinone
- melt
- Prior art date
Links
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 54
- 239000000460 chlorine Substances 0.000 claims description 54
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 33
- 239000000155 melt Substances 0.000 claims description 24
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 claims description 6
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- -1 methoxy, ethoxy, isopropoxy Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FAVDZWIRBSMLOV-UHFFFAOYSA-N 1,7-dinitroanthracene-9,10-dione Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 FAVDZWIRBSMLOV-UHFFFAOYSA-N 0.000 description 2
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 2
- QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 2
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 1
- QCRQDGXGTSBWFK-UHFFFAOYSA-N 1-methoxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2OC QCRQDGXGTSBWFK-UHFFFAOYSA-N 0.000 description 1
- XFLONXIGNOXKCG-UHFFFAOYSA-N 2,7-dinitroanthracene-9,10-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 XFLONXIGNOXKCG-UHFFFAOYSA-N 0.000 description 1
- QWVMIYZXMZSUIZ-UHFFFAOYSA-N 2-methyl-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C)C([N+]([O-])=O)=C2 QWVMIYZXMZSUIZ-UHFFFAOYSA-N 0.000 description 1
- WSEZCFGGGXRVHA-UHFFFAOYSA-N 6-chloro-1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] WSEZCFGGGXRVHA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BHBIPLOIWQSVID-UHFFFAOYSA-N thiohypofluorous acid Chemical compound SF BHBIPLOIWQSVID-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2654650A DE2654650C3 (de) | 1976-12-02 | 1976-12-02 | Verfahren zur kontinuierlichen Herstellung von Chloranthrachinonen |
| DE2749416A DE2749416C2 (de) | 1977-11-04 | 1977-11-04 | Verfahren zur Herstellung von Chloranthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH628607A5 true CH628607A5 (en) | 1982-03-15 |
Family
ID=25771210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1460277A CH628607A5 (en) | 1976-12-02 | 1977-11-29 | Process for preparing chloroanthraquinones |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5377049A (enExample) |
| CH (1) | CH628607A5 (enExample) |
| FR (1) | FR2372790A1 (enExample) |
| GB (1) | GB1551585A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH653666A5 (de) * | 1983-06-23 | 1986-01-15 | Ciba Geigy Ag | Verfahren zur herstellung von bromanthrachinonen. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1969044A (en) * | 1931-04-14 | 1934-08-07 | Ici Ltd | Dyestuff of the anthraquinone series and process of preparing the same |
| GB1457220A (en) * | 1974-11-02 | 1976-12-01 | Bayer Ag | Process for the preparation of halogenoanthraquinones |
| DE2452014C3 (de) * | 1974-11-02 | 1979-06-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Halogenanthrachinonen |
| GB1492137A (en) * | 1974-12-07 | 1977-11-16 | Bayer Ag | Process for concentrating halogenoanthraquinones |
-
1977
- 1977-11-29 CH CH1460277A patent/CH628607A5/de not_active IP Right Cessation
- 1977-11-29 GB GB4961877A patent/GB1551585A/en not_active Expired
- 1977-12-01 JP JP14336677A patent/JPS5377049A/ja active Pending
- 1977-12-02 FR FR7736402A patent/FR2372790A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1551585A (en) | 1979-08-30 |
| JPS5377049A (en) | 1978-07-08 |
| FR2372790B1 (enExample) | 1982-10-29 |
| FR2372790A1 (fr) | 1978-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |