DE2206960B2 - Verfahren zur herstellung von dinitroanthrachinon-freiem 1-nitroanthrachinon - Google Patents
Verfahren zur herstellung von dinitroanthrachinon-freiem 1-nitroanthrachinonInfo
- Publication number
- DE2206960B2 DE2206960B2 DE19722206960 DE2206960A DE2206960B2 DE 2206960 B2 DE2206960 B2 DE 2206960B2 DE 19722206960 DE19722206960 DE 19722206960 DE 2206960 A DE2206960 A DE 2206960A DE 2206960 B2 DE2206960 B2 DE 2206960B2
- Authority
- DE
- Germany
- Prior art keywords
- sulfite
- parts
- weight
- nitroanthraquinone
- anthraquinone
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title 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 16
- 150000004056 anthraquinones Chemical class 0.000 claims description 16
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 16
- 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 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 10
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 8
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 235000010265 sodium sulphite Nutrition 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 5
- 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 4
- 238000000746 purification Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 239000004285 Potassium sulphite Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 claims 1
- 235000019252 potassium sulphite Nutrition 0.000 claims 1
- 239000012264 purified product Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 229940001482 sodium sulfite Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- -1 alkali metal sulfite Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 238000011083 clear filtration Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
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 |
|---|---|---|---|
| CH225171A CH554308A (de) | 1971-02-16 | 1971-02-16 | Verfahren zur herstellung von dinitroanthrachinon-freiem 1-nitroanthrachinon. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2206960A1 DE2206960A1 (de) | 1972-08-31 |
| DE2206960B2 true DE2206960B2 (de) | 1976-05-06 |
Family
ID=4229395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722206960 Granted DE2206960B2 (de) | 1971-02-16 | 1972-02-14 | Verfahren zur herstellung von dinitroanthrachinon-freiem 1-nitroanthrachinon |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3798244A (enExample) |
| JP (1) | JPS5432010B1 (enExample) |
| CH (1) | CH554308A (enExample) |
| DE (1) | DE2206960B2 (enExample) |
| FR (1) | FR2125887A5 (enExample) |
| GB (1) | GB1374341A (enExample) |
| IT (1) | IT948535B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794823A (fr) * | 1972-02-01 | 1973-07-31 | Sandoz Sa | Procede de purification de la 1-nitroanthraquinone |
| DE2248990A1 (de) * | 1972-10-06 | 1974-04-11 | Bayer Ag | Verfahren zur herstellung von l-nitroanthrachinon |
| DE2256644C2 (de) * | 1972-11-18 | 1983-10-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von reinem 1-Nitro-anthrachinon |
| DE2259074C3 (de) * | 1972-12-02 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von praktisch 1,5-Dinitro-anthrachinon-freiem 1-Nitro-anthrachinon |
| DE2552560A1 (de) * | 1974-12-05 | 1976-06-10 | Sandoz Ag | Verfahren zum reinigen von l-nitroanthrachinon |
| CN102746692B (zh) * | 2012-06-18 | 2014-04-23 | 绍兴奇彩化工有限公司 | 一种分散蓝2bln的制备方法 |
| CN102746691A (zh) * | 2012-06-18 | 2012-10-24 | 绍兴奇彩化工有限公司 | 分散蓝2bln母液分离技术 |
-
1971
- 1971-02-16 CH CH225171A patent/CH554308A/xx not_active IP Right Cessation
-
1972
- 1972-02-11 FR FR7204593A patent/FR2125887A5/fr not_active Expired
- 1972-02-11 GB GB647872A patent/GB1374341A/en not_active Expired
- 1972-02-14 US US00226326A patent/US3798244A/en not_active Expired - Lifetime
- 1972-02-14 DE DE19722206960 patent/DE2206960B2/de active Granted
- 1972-02-15 JP JP1527572A patent/JPS5432010B1/ja active Pending
- 1972-02-15 IT IT20577/72A patent/IT948535B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DE2206960A1 (de) | 1972-08-31 |
| IT948535B (it) | 1973-06-11 |
| GB1374341A (en) | 1974-11-20 |
| US3798244A (en) | 1974-03-19 |
| JPS5432010B1 (enExample) | 1979-10-11 |
| FR2125887A5 (enExample) | 1972-09-29 |
| CH554308A (de) | 1974-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |