DE171588C - - Google Patents

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Publication number

DE171588C

DE171588C DENDAT171588D DE171588DA DE171588C DE 171588 C DE171588 C DE 171588C DE NDAT171588 D DENDAT171588 D DE NDAT171588D DE 171588D A DE171588D A DE 171588DA DE 171588 C DE171588 C DE 171588C

Authority

DE

Germany

Prior art keywords

urethanes

acid

red

urethane

orange

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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• 150000003673 urethanes Chemical class 0.000 claims description 8
• KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
• 238000006396 nitration reaction Methods 0.000 claims description 2
• 238000000034 method Methods 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
• 229910017604 nitric acid Inorganic materials 0.000 description 5
• -1 mononitroacetylmonoaminoanthraquinones Chemical class 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 3
• 239000012362 glacial acetic acid Substances 0.000 description 3
• 239000005457 ice water Substances 0.000 description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
• 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 2
• LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• YSJKYAHYBFJVKV-UHFFFAOYSA-N ethyl n-nitrocarbamate Chemical compound CCOC(=O)N[N+]([O-])=O YSJKYAHYBFJVKV-UHFFFAOYSA-N 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• CVQDLPIREXNIHP-UHFFFAOYSA-N 1,2,3,4,5,6-hexaaminoanthracene-9,10-dione Chemical class NC=1C(=C2C(C=3C(=C(C(=C(C=3C(C2=CC=1)=O)N)N)N)N)=O)N CVQDLPIREXNIHP-UHFFFAOYSA-N 0.000 description 1
• XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
• YYYARFHFWYKNLF-UHFFFAOYSA-N 4-[(2,4-dimethylphenyl)diazenyl]-3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=C12 YYYARFHFWYKNLF-UHFFFAOYSA-N 0.000 description 1
• 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 239000002253 acid Substances 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
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 238000000151 deposition Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• UEGTUUCLWIRSMP-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-n-nitronitramide Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N([N+](=O)[O-])[N+]([O-])=O UEGTUUCLWIRSMP-UHFFFAOYSA-N 0.000 description 1
• WDJHNJSBPXRITJ-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)acetamide Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C WDJHNJSBPXRITJ-UHFFFAOYSA-N 0.000 description 1
• PKKXOTQQOSFKHN-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)nitramide Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N[N+](=O)[O-] PKKXOTQQOSFKHN-UHFFFAOYSA-N 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1