DE1084268B - Verfahren zur Herstellung von 1-Acetylamino-2-chlor- bzw. 1-Acetylamino-2-bromnaphthalin-sulfonsaeuren - Google Patents
Verfahren zur Herstellung von 1-Acetylamino-2-chlor- bzw. 1-Acetylamino-2-bromnaphthalin-sulfonsaeurenInfo
- Publication number
- DE1084268B DE1084268B DEF26631A DEF0026631A DE1084268B DE 1084268 B DE1084268 B DE 1084268B DE F26631 A DEF26631 A DE F26631A DE F0026631 A DEF0026631 A DE F0026631A DE 1084268 B DE1084268 B DE 1084268B
- Authority
- DE
- Germany
- Prior art keywords
- acetylamino
- sulfonic acid
- bromonaphthalene
- chloro
- acid
- 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
- -1 1-acetylamino-2-bromonaphthalene sulfonic acid Chemical compound 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000012362 glacial acetic acid Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- OKQIEBVRUGLWOR-UHFFFAOYSA-N n-naphthalen-1-ylacetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1 OKQIEBVRUGLWOR-UHFFFAOYSA-N 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- HWAUAPHDMHWNCM-UHFFFAOYSA-N 4-acetamidonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 HWAUAPHDMHWNCM-UHFFFAOYSA-N 0.000 description 1
- VGPCCJBOHQGWLW-UHFFFAOYSA-N 5-acetamidonaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1S(O)(=O)=O VGPCCJBOHQGWLW-UHFFFAOYSA-N 0.000 description 1
- MRBULUHDJXUWDD-UHFFFAOYSA-N 5-amino-6-bromonaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(Br)C=CC2=C1S(O)(=O)=O MRBULUHDJXUWDD-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IMVIXDCJEMBUAY-UHFFFAOYSA-N n-(2-bromonaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=C(Br)C=CC2=C1 IMVIXDCJEMBUAY-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL105125D NL105125C (enrdf_load_stackoverflow) | 1958-09-18 | ||
| BE582747D BE582747A (enrdf_load_stackoverflow) | 1958-09-18 | ||
| NL243331D NL243331A (enrdf_load_stackoverflow) | 1958-09-18 | ||
| DEF26631A DE1084268B (de) | 1958-09-18 | 1958-09-18 | Verfahren zur Herstellung von 1-Acetylamino-2-chlor- bzw. 1-Acetylamino-2-bromnaphthalin-sulfonsaeuren |
| FR805310A FR1244425A (fr) | 1958-09-18 | 1959-09-17 | Procédé de préparation d'acides 1-acylamino-2-chloro- ou -2-bromonaphtalène-sulfoniques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26631A DE1084268B (de) | 1958-09-18 | 1958-09-18 | Verfahren zur Herstellung von 1-Acetylamino-2-chlor- bzw. 1-Acetylamino-2-bromnaphthalin-sulfonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1084268B true DE1084268B (de) | 1960-06-30 |
Family
ID=7092094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF26631A Pending DE1084268B (de) | 1958-09-18 | 1958-09-18 | Verfahren zur Herstellung von 1-Acetylamino-2-chlor- bzw. 1-Acetylamino-2-bromnaphthalin-sulfonsaeuren |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE582747A (enrdf_load_stackoverflow) |
| DE (1) | DE1084268B (enrdf_load_stackoverflow) |
| FR (1) | FR1244425A (enrdf_load_stackoverflow) |
| NL (2) | NL105125C (enrdf_load_stackoverflow) |
-
0
- NL NL243331D patent/NL243331A/xx unknown
- BE BE582747D patent/BE582747A/xx unknown
- NL NL105125D patent/NL105125C/xx active
-
1958
- 1958-09-18 DE DEF26631A patent/DE1084268B/de active Pending
-
1959
- 1959-09-17 FR FR805310A patent/FR1244425A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL105125C (enrdf_load_stackoverflow) | |
| NL243331A (enrdf_load_stackoverflow) | |
| FR1244425A (fr) | 1960-10-28 |
| BE582747A (enrdf_load_stackoverflow) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1084268B (de) | Verfahren zur Herstellung von 1-Acetylamino-2-chlor- bzw. 1-Acetylamino-2-bromnaphthalin-sulfonsaeuren | |
| DE840545C (de) | Verfahren zur Herstellung von Azoverbindungen | |
| EP0144701B1 (de) | Verfahren zur Herstellung von 2-Amino-l-hydroxy-4- oder -5-(beta-sulfatoäthylsulfonyl)-benzol-Verbindungen und deren Verwendung zur Synthese von faserreaktiven Verbindungen | |
| CH274425A (de) | Verfahren zur Herstellung eines metallhaltigen Monoazofarbstoffes. | |
| DE863968C (de) | Verfahren zur Herstellung neuer, esterartiger Azofarbstoffderivate | |
| AT226856B (de) | Verfahren zur Herstellung von neuen reaktiven Phthalocyaninfarbstoffen | |
| CH267269A (de) | Verfahren zur Herstellung eines Azofarbstoffes. | |
| DE1263947B (de) | Verfahren zur Herstellung von Ammoniumsalzen sulfonsaeuregruppenhaltiger Chromkomplexfarbstoffe | |
| CH267272A (de) | Verfahren zur Herstellung eines Azofarbstoffes. | |
| AT233010B (de) | Verfahren zur Herstellung von neuen Benzo-dihydro-1, 2, 4-thiadiazin-1, 1-dioxyden | |
| DE1916713C (de) | Benzoesauredenvate | |
| DE1695035C3 (de) | Verfahren zur Herstellung von 5-Chlor-2,3-pyridindiol | |
| DE744959C (de) | Verfahren zur Herstellung von 3-Alkoxy-4-oxybenzaldehyden | |
| DE1006429B (de) | Verfahren zur Herstellung wasserloeslicher Kondensationsprodukte des Rutins | |
| CH267271A (de) | Verfahren zur Herstellung eines Azofarbstoffes. | |
| CH391714A (de) | Verfahren zur Herstellung von neuen Sulfonamiden der Pyrimidinreihe | |
| DE1024971B (de) | Verfahren zur Herstellung von 2,5-Diaryl-1,3,4-oxdiazolen | |
| CH213814A (de) | Verfahren zur Erzeugung von wasserlöslichem Dihydrochlorid der Dihydrocuprein-azobenzen-para-sulfonsäure. | |
| DE1226593B (de) | Verfahren zur Herstellung von reinem 1H-Naphtho[1, 8-de]-1, 2, 3-triazin | |
| CH229982A (de) | Verfahren zur Darstellung von 5,7-Dichlor-8-oxychinaldin. | |
| CH123864A (de) | Verfahren zur Darstellung der 5-Methyl-4-oxy-3-acetaminobenzol-1-arsinsäure. | |
| CH143292A (de) | Verfahren zur Herstellung einer Cyclammoniumverbindung. | |
| EP0286971A2 (de) | Kationische Diazacyaninfarbstoffe | |
| CH374133A (de) | Verfahren zur Herstellung von diamino-1,1'-dianthrachinonylen | |
| DE1292143B (de) | Verfahren zur Reinigung von rohem 1,2-Diphenyl-3,5-dioxo-4-(3'-oxobutyl)-pyrazolidin |