DE167410C - - Google Patents

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Publication number

DE167410C

DE167410C DENDAT167410D DE167410DA DE167410C DE 167410 C DE167410 C DE 167410C DE NDAT167410 D DENDAT167410 D DE NDAT167410D DE 167410D A DE167410D A DE 167410DA DE 167410 C DE167410 C DE 167410C

Authority

DE

Germany

Prior art keywords

nitro

aminoanthraquinone

urethane

yellow

red

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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• 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 8
• 150000003673 urethanes Chemical class 0.000 claims description 8
• 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 claims description 2
• 150000002823 nitrates Chemical class 0.000 claims 1
• 239000000047 product Substances 0.000 description 10
• JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
• -1 compound compounds Chemical class 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 239000000203 mixture Substances 0.000 description 7
• 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 6
• LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 238000006396 nitration reaction Methods 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• WTCXIALFOUPXPZ-UHFFFAOYSA-N 2-amino-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C([N+]([O-])=O)=C2 WTCXIALFOUPXPZ-UHFFFAOYSA-N 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 230000000802 nitrating Effects 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• JTVJRNPZQWLJIZ-UHFFFAOYSA-N 1-amino-2-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC([N+]([O-])=O)=C2N JTVJRNPZQWLJIZ-UHFFFAOYSA-N 0.000 description 2
• 229960000583 Acetic Acid Drugs 0.000 description 2
• KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
• WMZDDDSWEHQHEQ-UHFFFAOYSA-N NC(=O)OCC.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical compound NC(=O)OCC.C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O WMZDDDSWEHQHEQ-UHFFFAOYSA-N 0.000 description 2
• CBXWGGFGZDVPNV-UHFFFAOYSA-N SO4-SO4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• 230000001476 alcoholic Effects 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 150000004056 anthraquinones Chemical class 0.000 description 2
• 239000004327 boric acid Substances 0.000 description 2
• 238000007865 diluting Methods 0.000 description 2
• YSJKYAHYBFJVKV-UHFFFAOYSA-N ethyl N-nitrocarbamate Chemical class CCOC(=O)N[N+]([O-])=O YSJKYAHYBFJVKV-UHFFFAOYSA-N 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 239000012452 mother liquor Substances 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
• IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 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 1
• KXMLYSJUXIUOHI-UHFFFAOYSA-N 1-amino-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2N KXMLYSJUXIUOHI-UHFFFAOYSA-N 0.000 description 1
• FFRBMBIXVSCUFS-UHFFFAOYSA-N Martius yellow Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
• 240000002799 Prunus avium Species 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
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
• 150000003855 acyl compounds Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 235000019693 cherries Nutrition 0.000 description 1
• 238000004140 cleaning Methods 0.000 description 1
• 230000000875 corresponding Effects 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000005712 crystallization Effects 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 230000001264 neutralization Effects 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 229910052717 sulfur Inorganic materials 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1