BE501463A - - Google Patents

Info

Publication number

BE501463A

BE501463A BE501463DA BE501463A BE 501463 A BE501463 A BE 501463A BE 501463D A BE501463D A BE 501463DA BE 501463 A BE501463 A BE 501463A

Authority

BE

Belgium

Prior art keywords

acid

sep

parts

amino

dye

Prior art date

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• 239000000975 dye Substances 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 37
• 230000008878 coupling Effects 0.000 claims description 20
• 238000010168 coupling process Methods 0.000 claims description 20
• 238000005859 coupling reaction Methods 0.000 claims description 20
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 6
• 230000007935 neutral effect Effects 0.000 claims description 6
• 230000009466 transformation Effects 0.000 claims description 6
• 239000000987 azo dye Substances 0.000 claims description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• 230000002378 acidificating effect Effects 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
• IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical class ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• 239000000243 solution Substances 0.000 description 18
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 239000000843 powder Substances 0.000 description 15
• 235000011121 sodium hydroxide Nutrition 0.000 description 12
• 239000000203 mixture Substances 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
• 239000000047 product Substances 0.000 description 5
• 235000002639 sodium chloride Nutrition 0.000 description 5
• 159000000000 sodium salts Chemical class 0.000 description 5
• NGRYSCJUFBVWTA-UHFFFAOYSA-N 4-amino-6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(O)C=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NGRYSCJUFBVWTA-UHFFFAOYSA-N 0.000 description 3
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 238000001035 drying Methods 0.000 description 3
• 238000001914 filtration Methods 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 238000005185 salting out Methods 0.000 description 3
• 235000010288 sodium nitrite Nutrition 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
• OGSZAQASQUXQOD-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(O)C(O)=CC2=C1 OGSZAQASQUXQOD-UHFFFAOYSA-N 0.000 description 2
• HASZQMUXEZXOJG-UHFFFAOYSA-N 3-diazo-4-methoxycyclohexa-1,5-diene-1-sulfonic acid Chemical compound [N+](=[N-])=C1C(C=CC(=C1)S(=O)(=O)O)OC HASZQMUXEZXOJG-UHFFFAOYSA-N 0.000 description 2
• ZTMVXIHBBGXFBB-UHFFFAOYSA-N 3-diazocyclohexa-1,5-diene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1C=CC(S(O)(=O)=O)=CC1=[N+]=[N-] ZTMVXIHBBGXFBB-UHFFFAOYSA-N 0.000 description 2
• HBMLCYVPHOHYCT-UHFFFAOYSA-N 6-diazo-3-nitrocyclohexa-2,4-diene-1-carboxylic acid Chemical compound [N+](=[N-])=C1C(C=C(C=C1)[N+](=O)[O-])C(=O)O HBMLCYVPHOHYCT-UHFFFAOYSA-N 0.000 description 2
• QNTYQLOUVRVHIB-UHFFFAOYSA-N 6-diazo-4-sulfocyclohexa-2,4-diene-1-carboxylic acid Chemical compound C(=O)(O)C1C(C=C(C=C1)S(=O)(=O)O)=[N+]=[N-] QNTYQLOUVRVHIB-UHFFFAOYSA-N 0.000 description 2
• MFCDHQNPTNBIGC-UHFFFAOYSA-N 6-diazocyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CC=CC1=[N+]=[N-] MFCDHQNPTNBIGC-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• 125000000217 alkyl group Chemical group 0.000 description 2
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 125000003118 aryl group Chemical group 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
• -1 2-Diazobenzene-1,5-dicarboxylic Chemical compound 0.000 description 1
• YEHPDJLWYYTFTG-UHFFFAOYSA-N 3-diazocyclohexa-1,5-diene-1,4-dicarboxylic acid Chemical compound [N+](=[N-])=C1C(C=CC(=C1)C(=O)O)C(=O)O YEHPDJLWYYTFTG-UHFFFAOYSA-N 0.000 description 1
• QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
• GZGVYVCAQGXZGA-UHFFFAOYSA-N 6-diazo-3-sulfocyclohexa-2,4-diene-1-carboxylic acid Chemical compound [N+](=[N-])=C1C(C=C(C=C1)S(=O)(=O)O)C(=O)O GZGVYVCAQGXZGA-UHFFFAOYSA-N 0.000 description 1
• VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 1
• SYMAOPXKWWZQIR-UHFFFAOYSA-N 8-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(O)=CC=CC2=C1 SYMAOPXKWWZQIR-UHFFFAOYSA-N 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• 229910006074 SO2NH2 Inorganic materials 0.000 description 1
• 229910006069 SO3H Inorganic materials 0.000 description 1
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000003518 caustics Substances 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 150000001875 compounds Chemical class 0.000 description 1
• 125000004093 cyano group Chemical group *C#N 0.000 description 1
• 238000004043 dyeing Methods 0.000 description 1
• 150000004675 formic acid derivatives Chemical class 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical class 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 150000002826 nitrites Chemical class 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 125000000565 sulfonamide group Chemical group 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1