DE147851C - - Google Patents

Info

Publication number

DE147851C

DE147851C DENDAT147851D DE147851DA DE147851C DE 147851 C DE147851 C DE 147851C DE NDAT147851 D DENDAT147851 D DE NDAT147851D DE 147851D A DE147851D A DE 147851DA DE 147851 C DE147851 C DE 147851C

Authority

DE

Germany

Prior art keywords

nitroamidoanthraquinone

dinitroanthraquinone

dinitroanthraquinones

reduction

dimethylaniline

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.)

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• 238000000034 method Methods 0.000 claims description 6
• 125000005265 dialkylamine group Chemical group 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• 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 description 10
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• -1 dihydroxylamine anthraquinones Chemical class 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 125000003118 aryl group Chemical group 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• 230000001603 reducing effect Effects 0.000 description 2
• 239000007858 starting material Substances 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
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 125000003368 amide group Chemical group 0.000 description 1
• 150000001412 amines Chemical group 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
• JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 1
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
• MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
• 229940067157 phenylhydrazine Drugs 0.000 description 1
• 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
• 150000003336 secondary aromatic amines Chemical class 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 150000003513 tertiary aromatic amines Chemical class 0.000 description 1

Cited By (1)