BE484836A - - Google Patents
Info
- Publication number
- BE484836A BE484836A BE484836DA BE484836A BE 484836 A BE484836 A BE 484836A BE 484836D A BE484836D A BE 484836DA BE 484836 A BE484836 A BE 484836A
- Authority
- BE
- Belgium
- Prior art keywords
- parts
- carbonyl
- hydrazine
- oxodiazole
- anthraquinone
- Prior art date
Links
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- 239000000975 dye Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 210000004940 Nucleus Anatomy 0.000 description 5
- 150000004056 anthraquinones Chemical class 0.000 description 5
- -1 anthraquinonyl Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000984 vat dye Substances 0.000 description 5
- CTGJDBCTMNANBE-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carbohydrazide Chemical compound C1=CC=C2C(=O)C3=C(N)C(C(=O)NN)=CC=C3C(=O)C2=C1 CTGJDBCTMNANBE-UHFFFAOYSA-N 0.000 description 4
- 229940042795 Hydrazides for tuberculosis treatment Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- NWFOTILLJRKQQH-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2[N+](=O)[O-] NWFOTILLJRKQQH-UHFFFAOYSA-N 0.000 description 3
- ZGCHATBSUIJLRL-UHFFFAOYSA-N Hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 3
- 239000012493 hydrazine sulfate Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- BIZVHVKTTCPVPP-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2N BIZVHVKTTCPVPP-UHFFFAOYSA-N 0.000 description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- MMKNBFSDCOALQO-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(O)=O)=C2N MMKNBFSDCOALQO-UHFFFAOYSA-N 0.000 description 1
- JOVXWCNPCIBTJQ-UHFFFAOYSA-N 1-chloro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C(=O)Cl)=CC=C3C(=O)C2=C1 JOVXWCNPCIBTJQ-UHFFFAOYSA-N 0.000 description 1
- ZHLRCPOFSPCJPL-UHFFFAOYSA-N 1-chloro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C(=O)O)=CC=C3C(=O)C2=C1 ZHLRCPOFSPCJPL-UHFFFAOYSA-N 0.000 description 1
- ATNRQUWWDJOENL-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carbohydrazide Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)NN)=CC=C3C(=O)C2=C1 ATNRQUWWDJOENL-UHFFFAOYSA-N 0.000 description 1
- HRKJWVBTIZPZJV-UHFFFAOYSA-N 1-nitro-N'-(1-nitro-9,10-dioxoanthracene-2-carbonyl)-9,10-dioxoanthracene-2-carbohydrazide Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)NNC(=O)C4=C(C=5C(=O)C6=CC=CC=C6C(=O)C=5C=C4)[N+](=O)[O-])=CC=C3C(=O)C2=C1 HRKJWVBTIZPZJV-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- DTJZVTZAKHHCHS-UHFFFAOYSA-N 4-nitropyrazol-3-one Chemical class [O-][N+](=O)C1=CN=NC1=O DTJZVTZAKHHCHS-UHFFFAOYSA-N 0.000 description 1
- LLSVGXGSYBLMNY-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)Cl LLSVGXGSYBLMNY-UHFFFAOYSA-N 0.000 description 1
- DGJNWQJOASAMHY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)Cl)=CC=C3C(=O)C2=C1 DGJNWQJOASAMHY-UHFFFAOYSA-N 0.000 description 1
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 description 1
- HOTCUYUAFLJZKZ-UHFFFAOYSA-N C1(=CC=CC=2C(C3=CC=CC=C3C(C1=2)=O)=O)C=1C(N=NC=1)=O Chemical class C1(=CC=CC=2C(C3=CC=CC=C3C(C1=2)=O)=O)C=1C(N=NC=1)=O HOTCUYUAFLJZKZ-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- PTIRLODIWSXPBG-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=CC=2C(C3=CC(=CC=C3C(C12)=O)C(=O)Cl)=O Chemical compound [N+](=O)([O-])C1=CC=CC=2C(C3=CC(=CC=C3C(C12)=O)C(=O)Cl)=O PTIRLODIWSXPBG-UHFFFAOYSA-N 0.000 description 1
- KSDKUTSQPZBFLM-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=CC=2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O Chemical compound [N+](=O)([O-])C1=CC=CC=2C(C3=CC(=CC=C3C(C12)=O)C(=O)O)=O KSDKUTSQPZBFLM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PPAJMIIIQKXWIV-UHFFFAOYSA-N anthracene-9,10-dione;pyrazol-3-one Chemical class O=C1C=CN=N1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 PPAJMIIIQKXWIV-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RWVIIDFPPPPSDT-UHFFFAOYSA-N thionyl dichloride;toluene Chemical compound ClS(Cl)=O.CC1=CC=CC=C1 RWVIIDFPPPPSDT-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE484836A true BE484836A (it) |
Family
ID=130900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE484836D BE484836A (it) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE484836A (it) |
-
0
- BE BE484836D patent/BE484836A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE484836A (it) | ||
| US677239A (en) | Halogen-substituted indigo and process of making same. | |
| CH292803A (fr) | Procédé de préparation d'un colorant pour cuve. | |
| US1874584A (en) | Production of new vat dyestuffs | |
| US807181A (en) | Yellow-green dye and process of making same. | |
| BE542525A (it) | ||
| BE471144A (it) | ||
| US609352A (en) | Paul julius | |
| US856776A (en) | Tetrabromo derivative of indigo and process of making same. | |
| BE496405A (it) | ||
| BE590513A (it) | ||
| CH355238A (fr) | Procédé de préparation de colorants monoazoïques | |
| BE685426A (it) | ||
| BE474073A (it) | ||
| BE545435A (it) | ||
| BE487807A (it) | ||
| BE620899A (it) | ||
| BE524797A (it) | ||
| BE509646A (it) | ||
| BE557245A (it) | ||
| BE570888A (it) | ||
| CH296545A (fr) | Procédé de préparation d'un colorant pour cuve. | |
| BE532338A (it) | ||
| BE523495A (it) | ||
| BE532948A (it) |