CA1060008A - Process for the preparation of halogenoanthraquinones - Google Patents
Process for the preparation of halogenoanthraquinonesInfo
- Publication number
- CA1060008A CA1060008A CA238,759A CA238759A CA1060008A CA 1060008 A CA1060008 A CA 1060008A CA 238759 A CA238759 A CA 238759A CA 1060008 A CA1060008 A CA 1060008A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- chlorine
- nitroanthraquinones
- mixture
- melt
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 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 abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003085 diluting agent Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- 239000000155 melt Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class 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 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 claims description 2
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229940060038 chlorine Drugs 0.000 claims 7
- 235000017168 chlorine Nutrition 0.000 claims 7
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- NGQRAAQPTFAOQG-UHFFFAOYSA-N 1-chloro-2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NGQRAAQPTFAOQG-UHFFFAOYSA-N 0.000 description 1
- XXUOKOYLVBHBCG-UHFFFAOYSA-N 1-hydroxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O XXUOKOYLVBHBCG-UHFFFAOYSA-N 0.000 description 1
- PMOCDYOEOUEPAN-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)O)=CC=C3C(=O)C2=C1 PMOCDYOEOUEPAN-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
- KBVOCALKCZCXKK-UHFFFAOYSA-N 4,5-dichloro-1-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] KBVOCALKCZCXKK-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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- BMNDJWSIKZECMH-UHFFFAOYSA-N nitrosyl bromide Chemical compound BrN=O BMNDJWSIKZECMH-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2452014A DE2452014C3 (de) | 1974-11-02 | 1974-11-02 | Verfahren zur Herstellung von Halogenanthrachinonen |
| DE19742455587 DE2455587A1 (de) | 1974-11-23 | 1974-11-23 | Verfahren zur herstellung von halogenanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1060008A true CA1060008A (en) | 1979-08-07 |
Family
ID=25767917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,759A Expired CA1060008A (en) | 1974-11-02 | 1975-10-31 | Process for the preparation of halogenoanthraquinones |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4006171A (enExample) |
| JP (1) | JPS5168558A (enExample) |
| BR (1) | BR7507177A (enExample) |
| CA (1) | CA1060008A (enExample) |
| CH (1) | CH619681A5 (enExample) |
| DD (1) | DD122962A5 (enExample) |
| DK (1) | DK492275A (enExample) |
| ES (1) | ES442261A1 (enExample) |
| FR (1) | FR2289479A1 (enExample) |
| GB (1) | GB1457220A (enExample) |
| IE (1) | IE41925B1 (enExample) |
| IT (1) | IT1056163B (enExample) |
| LU (1) | LU73693A1 (enExample) |
| NL (1) | NL7512736A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2522177A1 (de) * | 1975-05-17 | 1976-11-25 | Bayer Ag | Verfahren zur herstellung von chloranthrachinonen aus nitroanthrachinonen |
| GB1551585A (en) * | 1976-12-02 | 1979-08-30 | Bayer Ag | Process for the preparation of chloroanthraquinones |
| US4206130A (en) * | 1977-05-10 | 1980-06-03 | Bayer Aktiengesellschaft | Process for the preparation of 1,5-dichloroanthraquinone |
| CH653666A5 (de) * | 1983-06-23 | 1986-01-15 | Ciba Geigy Ag | Verfahren zur herstellung von bromanthrachinonen. |
| JPS60117807A (ja) * | 1983-11-29 | 1985-06-25 | Matsushita Electric Ind Co Ltd | 表面波フィルタの帯域調整方法 |
| CN101863752A (zh) * | 2010-06-30 | 2010-10-20 | 合肥工业大学 | 一种氯气直接氯化合成1-氯蒽醌的方法 |
-
1975
- 1975-10-13 GB GB4182175A patent/GB1457220A/en not_active Expired
- 1975-10-24 US US05/625,725 patent/US4006171A/en not_active Expired - Lifetime
- 1975-10-28 CH CH1394775A patent/CH619681A5/de not_active IP Right Cessation
- 1975-10-30 JP JP50129957A patent/JPS5168558A/ja active Pending
- 1975-10-30 NL NL7512736A patent/NL7512736A/xx unknown
- 1975-10-31 DK DK492275A patent/DK492275A/da unknown
- 1975-10-31 CA CA238,759A patent/CA1060008A/en not_active Expired
- 1975-10-31 ES ES442261A patent/ES442261A1/es not_active Expired
- 1975-10-31 IE IE2373/75A patent/IE41925B1/en unknown
- 1975-10-31 FR FR7533474A patent/FR2289479A1/fr active Granted
- 1975-10-31 DD DD189183A patent/DD122962A5/xx unknown
- 1975-10-31 BR BR7507177*A patent/BR7507177A/pt unknown
- 1975-10-31 LU LU73693A patent/LU73693A1/xx unknown
- 1975-10-31 IT IT52020/75A patent/IT1056163B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5168558A (en) | 1976-06-14 |
| FR2289479A1 (fr) | 1976-05-28 |
| LU73693A1 (enExample) | 1976-08-13 |
| BR7507177A (pt) | 1976-08-03 |
| IE41925L (en) | 1976-05-02 |
| DK492275A (da) | 1976-05-03 |
| GB1457220A (en) | 1976-12-01 |
| FR2289479B1 (enExample) | 1979-01-05 |
| US4006171A (en) | 1977-02-01 |
| NL7512736A (nl) | 1976-05-04 |
| DD122962A5 (de) | 1976-11-12 |
| IT1056163B (it) | 1982-01-30 |
| CH619681A5 (enExample) | 1980-10-15 |
| IE41925B1 (en) | 1980-04-23 |
| ES442261A1 (es) | 1977-07-01 |
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