DE2030964A1 - Verfahren zur Herstellung nitrierter Azofarbstoffcarbonsauren - Google Patents
Verfahren zur Herstellung nitrierter AzofarbstoffcarbonsaurenInfo
- Publication number
- DE2030964A1 DE2030964A1 DE19702030964 DE2030964A DE2030964A1 DE 2030964 A1 DE2030964 A1 DE 2030964A1 DE 19702030964 DE19702030964 DE 19702030964 DE 2030964 A DE2030964 A DE 2030964A DE 2030964 A1 DE2030964 A1 DE 2030964A1
- Authority
- DE
- Germany
- Prior art keywords
- azo dye
- carboxylic acids
- acid
- nitrated
- formula
- 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.)
- Pending
Links
- 239000000987 azo dye Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 238000006396 nitration reaction Methods 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 6
- -1 nitro-azo carboxylic acids Chemical class 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 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
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- FOVOBTLEKSQTFG-UHFFFAOYSA-N 2,5-dimethoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=C(OC)C=C1N FOVOBTLEKSQTFG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MGLZGLAFFOMWPB-UHFFFAOYSA-N 2-chloro-1,4-phenylenediamine Chemical compound NC1=CC=C(N)C(Cl)=C1 MGLZGLAFFOMWPB-UHFFFAOYSA-N 0.000 description 1
- CPCPKQUNFFHAIZ-UHFFFAOYSA-N 2-chloro-5-methylbenzene-1,4-diamine Chemical compound CC1=CC(N)=C(Cl)C=C1N CPCPKQUNFFHAIZ-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- XJQRCFRVWZHIPN-UHFFFAOYSA-N 3-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1Cl XJQRCFRVWZHIPN-UHFFFAOYSA-N 0.000 description 1
- DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 1
- SPENLBANQJYBEA-UHFFFAOYSA-N 3-amino-n,n,4-trimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(C)C(N)=C1 SPENLBANQJYBEA-UHFFFAOYSA-N 0.000 description 1
- SQLINTILAKQRPD-UHFFFAOYSA-N 3-hydroxy-7-nitronaphthalene-2-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 SQLINTILAKQRPD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MEORYKCCIVWJRR-UHFFFAOYSA-N N-(4-aminophenyl)-4-phenylbenzamide Chemical compound C1(=CC=CC=C1)C1=CC=C(C(=O)NC2=CC=C(C=C2)N)C=C1 MEORYKCCIVWJRR-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- YEPWCJHMSVABPQ-UHFFFAOYSA-N methyl 3-amino-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(N)=C1 YEPWCJHMSVABPQ-UHFFFAOYSA-N 0.000 description 1
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- JFQKGZMJASBPNU-UHFFFAOYSA-N n-(4-aminophenyl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=C(N)C=C1 JFQKGZMJASBPNU-UHFFFAOYSA-N 0.000 description 1
- JDHKVOPFSRGZMT-UHFFFAOYSA-N n-(4-aminophenyl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=C(N)C=C1 JDHKVOPFSRGZMT-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- GTTFJYUWPUKXJH-UHFFFAOYSA-N n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 GTTFJYUWPUKXJH-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010626 work up procedure 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/04—Preparation of azo dyes from other azo compounds by nitration
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH998769A CH519559A (de) | 1969-06-30 | 1969-06-30 | Verfahren zur Herstellung nitrierter Azofarbstoffcarbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2030964A1 true DE2030964A1 (de) | 1971-01-14 |
Family
ID=4357873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702030964 Pending DE2030964A1 (de) | 1969-06-30 | 1970-06-23 | Verfahren zur Herstellung nitrierter Azofarbstoffcarbonsauren |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE752666A (enrdf_load_stackoverflow) |
| CH (1) | CH519559A (enrdf_load_stackoverflow) |
| DE (1) | DE2030964A1 (enrdf_load_stackoverflow) |
| ES (1) | ES381234A2 (enrdf_load_stackoverflow) |
| FR (1) | FR2048048B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1266489A (enrdf_load_stackoverflow) |
| NL (1) | NL7009576A (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR505007A (fr) * | 1916-08-01 | 1920-07-21 | Soc Ind Chimique Bale | Procédé pour la préparation de dérivés nitrés de colorants azoiques |
-
1969
- 1969-06-30 CH CH998769A patent/CH519559A/de not_active IP Right Cessation
-
1970
- 1970-06-03 GB GB1266489D patent/GB1266489A/en not_active Expired
- 1970-06-23 DE DE19702030964 patent/DE2030964A1/de active Pending
- 1970-06-26 FR FR7023852A patent/FR2048048B1/fr not_active Expired
- 1970-06-27 ES ES381234A patent/ES381234A2/es not_active Expired
- 1970-06-29 NL NL7009576A patent/NL7009576A/xx unknown
- 1970-06-29 BE BE752666D patent/BE752666A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE752666A (fr) | 1970-12-29 |
| FR2048048B1 (enrdf_load_stackoverflow) | 1973-10-19 |
| NL7009576A (enrdf_load_stackoverflow) | 1971-01-04 |
| GB1266489A (enrdf_load_stackoverflow) | 1972-03-08 |
| FR2048048A1 (enrdf_load_stackoverflow) | 1971-03-19 |
| CH519559A (de) | 1972-02-29 |
| ES381234A2 (es) | 1972-11-01 |
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