DE2410310C3 - Verfahren zur Reinigung von 1-Aminoanthrachinon - Google Patents
Verfahren zur Reinigung von 1-AminoanthrachinonInfo
- Publication number
- DE2410310C3 DE2410310C3 DE2410310A DE2410310A DE2410310C3 DE 2410310 C3 DE2410310 C3 DE 2410310C3 DE 2410310 A DE2410310 A DE 2410310A DE 2410310 A DE2410310 A DE 2410310A DE 2410310 C3 DE2410310 C3 DE 2410310C3
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- amino
- reaction
- water
- ammonia
- 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
- 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 title claims description 36
- 238000000034 method Methods 0.000 title claims description 15
- 238000000746 purification Methods 0.000 title claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 229910021529 ammonia Inorganic materials 0.000 claims description 25
- 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 16
- 238000007171 acid catalysis Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000005576 amination reaction Methods 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- QRKOHQULMICIPX-UHFFFAOYSA-N 4-amino-10-iminoanthracen-9-one Chemical compound O=C1C2=CC=CC=C2C(=N)C2=C1C=CC=C2N QRKOHQULMICIPX-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229940078552 o-xylene Drugs 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MARCAKLHFUYDJE-UHFFFAOYSA-N 1,2-xylene;hydrate Chemical compound O.CC1=CC=CC=C1C MARCAKLHFUYDJE-UHFFFAOYSA-N 0.000 description 1
- -1 1-amino anthraquinone imines Chemical class 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 150000004060 quinone imines Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410310A DE2410310C3 (de) | 1974-03-05 | 1974-03-05 | Verfahren zur Reinigung von 1-Aminoanthrachinon |
| US05/546,833 US4003924A (en) | 1974-03-05 | 1975-02-03 | Process for preparing 1-amino anthraquinone |
| GB822275A GB1445065A (en) | 1974-03-05 | 1975-02-27 | Process for the preparation of 1-amino anthraquinone |
| BE153866A BE826129A (fr) | 1974-03-05 | 1975-02-28 | Procede de preparation de la 1-amino-anthraquinone |
| IT48413/75A IT1029917B (it) | 1974-03-05 | 1975-03-03 | Procedimento per produrre i ammino antrachinone |
| CH265275A CH611874A5 (en:Method) | 1974-03-05 | 1975-03-03 | |
| NL7502483A NL7502483A (nl) | 1974-03-05 | 1975-03-03 | Werkwijze voor het bereiden van 1-amino-anthra- chinon. |
| JP50025108A JPS5761727B2 (en:Method) | 1974-03-05 | 1975-03-03 | |
| FR7506921A FR2263229B1 (en:Method) | 1974-03-05 | 1975-03-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410310A DE2410310C3 (de) | 1974-03-05 | 1974-03-05 | Verfahren zur Reinigung von 1-Aminoanthrachinon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2410310A1 DE2410310A1 (de) | 1975-09-18 |
| DE2410310B2 DE2410310B2 (de) | 1978-06-29 |
| DE2410310C3 true DE2410310C3 (de) | 1979-02-22 |
Family
ID=5909051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2410310A Expired DE2410310C3 (de) | 1974-03-05 | 1974-03-05 | Verfahren zur Reinigung von 1-Aminoanthrachinon |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4003924A (en:Method) |
| JP (1) | JPS5761727B2 (en:Method) |
| BE (1) | BE826129A (en:Method) |
| CH (1) | CH611874A5 (en:Method) |
| DE (1) | DE2410310C3 (en:Method) |
| FR (1) | FR2263229B1 (en:Method) |
| GB (1) | GB1445065A (en:Method) |
| IT (1) | IT1029917B (en:Method) |
| NL (1) | NL7502483A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102906A (en) * | 1973-07-10 | 1978-07-25 | Bayer Aktiengesellschaft | Process for preparing α-amino-β'-nitroanthraquinones |
| DE2827197A1 (de) * | 1978-06-21 | 1980-01-10 | Bayer Ag | Verfahren zur herstellung von aminoanthrachinonen |
| JPS6050426U (ja) * | 1983-09-13 | 1985-04-09 | 株式会社 ケ−・シ−・シ−・商会 | 電線の表示片取付具 |
| DE3433074A1 (de) * | 1984-09-08 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur erzeugung von aminoanthrachinonen mit verbesserten verarbeitungstechnischen eigenschaften |
| CN116143642A (zh) * | 2022-10-11 | 2023-05-23 | 淮阴工学院 | 一种连续氨解制备1-氨基蒽醌的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1792348A (en) * | 1928-12-29 | 1931-02-10 | Chem Ind Basel | Anthraquinone derivatives and process of making same |
-
1974
- 1974-03-05 DE DE2410310A patent/DE2410310C3/de not_active Expired
-
1975
- 1975-02-03 US US05/546,833 patent/US4003924A/en not_active Expired - Lifetime
- 1975-02-27 GB GB822275A patent/GB1445065A/en not_active Expired
- 1975-02-28 BE BE153866A patent/BE826129A/xx unknown
- 1975-03-03 NL NL7502483A patent/NL7502483A/xx unknown
- 1975-03-03 CH CH265275A patent/CH611874A5/xx not_active IP Right Cessation
- 1975-03-03 IT IT48413/75A patent/IT1029917B/it active
- 1975-03-03 JP JP50025108A patent/JPS5761727B2/ja not_active Expired
- 1975-03-05 FR FR7506921A patent/FR2263229B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5761727B2 (en:Method) | 1982-12-25 |
| JPS50121325A (en:Method) | 1975-09-23 |
| US4003924A (en) | 1977-01-18 |
| DE2410310B2 (de) | 1978-06-29 |
| BE826129A (fr) | 1975-08-28 |
| CH611874A5 (en:Method) | 1979-06-29 |
| GB1445065A (en) | 1976-08-04 |
| IT1029917B (it) | 1979-03-20 |
| NL7502483A (nl) | 1975-09-09 |
| DE2410310A1 (de) | 1975-09-18 |
| FR2263229B1 (en:Method) | 1978-10-06 |
| FR2263229A1 (en:Method) | 1975-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |