DE1245387B - Verfahren zur Herstellung von 1-Amino-2-hydroxyanthrachinonen - Google Patents
Verfahren zur Herstellung von 1-Amino-2-hydroxyanthrachinonenInfo
- Publication number
- DE1245387B DE1245387B DEF46941A DEF0046941A DE1245387B DE 1245387 B DE1245387 B DE 1245387B DE F46941 A DEF46941 A DE F46941A DE F0046941 A DEF0046941 A DE F0046941A DE 1245387 B DE1245387 B DE 1245387B
- Authority
- DE
- Germany
- Prior art keywords
- amino
- anthraquinone
- hydroxy
- parts
- found
- 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
- PZHGBWKPRMYCEF-UHFFFAOYSA-N 1-amino-2-hydroxyanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(O)=C2N PZHGBWKPRMYCEF-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000004345 1,2-dihydroxyanthraquinones Chemical class 0.000 claims description 3
- -1 1,2-dihydroxy-anthraquinone 1-hydroxy-2-aminoanthraquinone Chemical compound 0.000 description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 235000005811 Viola adunca Nutrition 0.000 description 8
- 235000013487 Viola odorata Nutrition 0.000 description 8
- 235000002254 Viola papilionacea Nutrition 0.000 description 8
- 244000172533 Viola sororia Species 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 240000009038 Viola odorata Species 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000001788 irregular Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- 244000154870 Viola adunca Species 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 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 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- QNUNPPJSRCMONZ-UHFFFAOYSA-N 1,2-dihydroxy-4-(4-methoxyanilino)anthracene-9,10-dione Chemical compound COC1=CC=C(C=C1)NC1=CC(=C(C=2C(C3=CC=CC=C3C(C12)=O)=O)O)O QNUNPPJSRCMONZ-UHFFFAOYSA-N 0.000 description 1
- GFFFQUROUBABAS-UHFFFAOYSA-N 1,4,8-triamino-2,5-dihydroxyanthracene-9,10-dione Chemical compound NC1=CC(O)=C(N)C2=C1C(=O)C1=C(O)C=CC(N)=C1C2=O GFFFQUROUBABAS-UHFFFAOYSA-N 0.000 description 1
- WYBBLDRNANYEKF-UHFFFAOYSA-N 1,4-diamino-2-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(O)C=C2N WYBBLDRNANYEKF-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- FJFNFDSQPIUJKQ-UHFFFAOYSA-N 4,8-diamino-1,2,5-trihydroxyanthracene-9,10-dione Chemical compound OC1=C(C=C(C=2C(C3=C(C=CC(=C3C(C12)=O)N)O)=O)N)O FJFNFDSQPIUJKQ-UHFFFAOYSA-N 0.000 description 1
- ICRPMHQBDMEAPH-UHFFFAOYSA-N 4,8-diamino-1,2-dihydroxyanthracene-9,10-dione Chemical compound OC1=C(C=C(C=2C(C3=CC=CC(=C3C(C12)=O)N)=O)N)O ICRPMHQBDMEAPH-UHFFFAOYSA-N 0.000 description 1
- RNAVBZRQFCASHH-UHFFFAOYSA-N 4-amino-1,2-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C=C2N RNAVBZRQFCASHH-UHFFFAOYSA-N 0.000 description 1
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46941A DE1245387B (de) | 1965-08-19 | 1965-08-19 | Verfahren zur Herstellung von 1-Amino-2-hydroxyanthrachinonen |
| LU51747A LU51747A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-08-19 | 1966-08-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46941A DE1245387B (de) | 1965-08-19 | 1965-08-19 | Verfahren zur Herstellung von 1-Amino-2-hydroxyanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1245387B true DE1245387B (de) | 1967-07-27 |
Family
ID=7101325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF46941A Pending DE1245387B (de) | 1965-08-19 | 1965-08-19 | Verfahren zur Herstellung von 1-Amino-2-hydroxyanthrachinonen |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1245387B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| LU (1) | LU51747A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1965
- 1965-08-19 DE DEF46941A patent/DE1245387B/de active Pending
-
1966
- 1966-08-10 LU LU51747A patent/LU51747A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU51747A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-10-10 |
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