DE2253553C2 - Verfahren zur Herstellung von 4-Amino-l,8-naphthalsäureimid-3-sulfonsäure - Google Patents
Verfahren zur Herstellung von 4-Amino-l,8-naphthalsäureimid-3-sulfonsäureInfo
- Publication number
- DE2253553C2 DE2253553C2 DE19722253553 DE2253553A DE2253553C2 DE 2253553 C2 DE2253553 C2 DE 2253553C2 DE 19722253553 DE19722253553 DE 19722253553 DE 2253553 A DE2253553 A DE 2253553A DE 2253553 C2 DE2253553 C2 DE 2253553C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- acid
- naphthalic
- ammonia
- reaction
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 238000006277 sulfonation reaction Methods 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- SSMIFVHARFVINF-UHFFFAOYSA-N 4-amino-1,8-naphthalimide Chemical compound O=C1NC(=O)C2=CC=CC3=C2C1=CC=C3N SSMIFVHARFVINF-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- -1 bromine compound Chemical class 0.000 claims description 2
- 239000010959 steel Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 8
- 239000004952 Polyamide Substances 0.000 claims 3
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims 3
- 239000000835 fiber Substances 0.000 claims 3
- 229920002647 polyamide Polymers 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- 238000004043 dyeing Methods 0.000 claims 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 2
- 229910001385 heavy metal Inorganic materials 0.000 claims 2
- 150000003949 imides Chemical group 0.000 claims 2
- 238000006396 nitration reaction Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- YZAFLLHEMBUGFB-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-4-sulfonic acid Chemical compound C1=CC2=CC(S(=O)(=O)O)=CC(CC3)=C2C3=C1 YZAFLLHEMBUGFB-UHFFFAOYSA-N 0.000 claims 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 1
- GTCAZWRERBLCFJ-UHFFFAOYSA-N 4-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N)=CC=C(C(O)=O)C2=C1 GTCAZWRERBLCFJ-UHFFFAOYSA-N 0.000 claims 1
- NPNRZUBMQUTWPW-UHFFFAOYSA-N 4-nitro-1,2-dihydroacenaphthylene Chemical compound C1=CC2=CC([N+](=O)[O-])=CC(CC3)=C2C3=C1 NPNRZUBMQUTWPW-UHFFFAOYSA-N 0.000 claims 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 claims 1
- VWPQCOZMXULHDM-UHFFFAOYSA-N 9-aminononanoic acid Chemical compound NCCCCCCCCC(O)=O VWPQCOZMXULHDM-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000005104 Neeliglow 4-amino-1,8-naphthalimide Substances 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229960001506 brilliant green Drugs 0.000 claims 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 claims 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 210000002268 wool Anatomy 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722253553 DE2253553C2 (de) | 1972-11-02 | 1972-11-02 | Verfahren zur Herstellung von 4-Amino-l,8-naphthalsäureimid-3-sulfonsäure |
| NL7314760A NL7314760A (enExample) | 1972-11-02 | 1973-10-26 | |
| CH1526873A CH584277A5 (enExample) | 1972-11-02 | 1973-10-30 | |
| JP12188073A JPS4977940A (enExample) | 1972-11-02 | 1973-10-31 | |
| FR7338843A FR2205513B1 (enExample) | 1972-11-02 | 1973-10-31 | |
| IT3081173A IT999142B (it) | 1972-11-02 | 1973-10-31 | Acidi 4 amino 1.8 naftalimid 3 solfonici e processo per la loro produzione |
| GB5093773A GB1415807A (en) | 1972-11-02 | 1973-11-02 | 4-amino-1,8-naphthalimido-3-sulphonic acids and process for preparing them |
| BE137395A BE806904A (fr) | 1972-11-02 | 1973-11-05 | Acides 4-amino-1,8-naphtalimide-3-sulfoniques et leur preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722253553 DE2253553C2 (de) | 1972-11-02 | 1972-11-02 | Verfahren zur Herstellung von 4-Amino-l,8-naphthalsäureimid-3-sulfonsäure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2253553B1 DE2253553B1 (de) | 1974-04-11 |
| DE2253553A1 DE2253553A1 (enExample) | 1974-04-11 |
| DE2253553C2 true DE2253553C2 (de) | 1974-11-07 |
Family
ID=5860602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722253553 Expired DE2253553C2 (de) | 1972-11-02 | 1972-11-02 | Verfahren zur Herstellung von 4-Amino-l,8-naphthalsäureimid-3-sulfonsäure |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE806904A (enExample) |
| DE (1) | DE2253553C2 (enExample) |
-
1972
- 1972-11-02 DE DE19722253553 patent/DE2253553C2/de not_active Expired
-
1973
- 1973-11-05 BE BE137395A patent/BE806904A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2253553B1 (de) | 1974-04-11 |
| DE2253553A1 (enExample) | 1974-04-11 |
| BE806904A (fr) | 1974-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2727484A1 (de) | Verfahren zur herstellung eines roten pigments aus perylen-3.4.9.10-tetracarbonsaeure-n,n'-bis-methylimid | |
| DE2253553C2 (de) | Verfahren zur Herstellung von 4-Amino-l,8-naphthalsäureimid-3-sulfonsäure | |
| DE929805C (de) | Verfahren zur Herstellung von Nickel- oder Kobalttetra-aza-porphinen bzw. ihren alkyl- und cycloalkylsubstituierten Derivaten | |
| CH639986A5 (de) | Verfahren zur herstellung von pigmentformen des perylen-3,4,9,10-tetracarbonsaeurediimids mit hoher lasur und brillanz. | |
| EP0123256B1 (de) | Verfahren zur Herstellung von 3,4,9,10-Perylentetracarbonsäurediimid | |
| DE1807729A1 (de) | Farbstoff der Perylentetracorbonsaeurediimidreihe | |
| DE2247971C3 (de) | Verfahren zur Herstellung von 3'-Hydroxychinophthalonen | |
| EP0054806B1 (de) | Verfahren zur Herstellung von Perylentetracarbonsäurediimid | |
| DE1960896C3 (de) | Lineare trans-Chinacridon-Pigmente, Verfahren zu ihrer Herstellung und mit ihnen gefärbte Lacke, Druckfarben und Kunststoffe | |
| AT163642B (de) | Verfahren zur Herstellung von Äthylenglykolestern der Terephthalsäure | |
| CH632290A5 (de) | Verfahren zur herstellung eines 3,4,9,10-perylentetracarbonsaeure-dianhydrid-pigmentes. | |
| DE3836674A1 (de) | Verfahren zur herstellung von kuepenfarbstoffen und pigmenten der perinon-reihe | |
| DE810052C (de) | Verfahren zur Herstellung von Leukoschwefelsaeureestern verkuepbarer Verbindungen der Anthrachinon- und Indigoreihe | |
| DE2220744B2 (de) | Derivate der l,l'-Dinaphthyl-4,4', 53'3^'-hexacarbonsäure, Verfahren zu deren Herstellung und ihre Verwendung | |
| DE2314875C3 (de) | Verfahren zur Herstellung von 4-Amino-1,8- naphthalsäureimid-3-sulfonsäuren, 4-Amino-1,8-naphthalsäureimid-3-sulfonsäuren und ihre Verwendung zum Färben von natürlichen und synthetischen Polyamidfasern | |
| DE2045908C3 (de) | Verfahren zur Herstellung von Kupferphthalocyaninen | |
| DE2300019C3 (de) | Verfahren zur direkten Herstellung von 1,9-Anthrapyrimidin-2-carbonsäure-1 '-anthrachinonylamid in Pigmentform | |
| DE1235473B (de) | Verfahren zur Herstellung von Dicarbonsaeureamiden der Anthrachinonreihe | |
| DE1120043B (de) | Verfahren zur Umwandlung eines Kobaltphthalocyanins in einen Kuepenfarbstoff mit verbesserter Loeslichkeit in der Kuepe | |
| DE2501742A1 (de) | O-(3-hydroxy-1-isochinolinyl)-benzoesaeure, n-phenylacetyl-phthalimid, verfahren zu dessen herstellung sowie ein verfahren zur herstellung von 7-oxo-7h-dibenzo- eckige klammer auf d e, h eckige klammer zu -chinolin-2-ol unter verwendung desselben | |
| DE810053C (de) | Verfahren zur Herstellung von Leukoschwefelsaeureestern verkuepbarer Verbindungen der Anthrachinon- und Indigoreihe | |
| DE2000510C3 (de) | Verfahren zur Herstellung von Flavanthrenen | |
| DE835917C (de) | Verfahren zur Herstellung von Methyl- und Chlormethylverbindungen von Pyrazolanthron-Benzanthronen und deren Leukoestern | |
| AT225316B (de) | Verfahren zur Herstellung von linearen Chinacridonfarbstoffen | |
| DE2320062A1 (de) | Verfahren zur herstellung von 1,4diaminoanthrachinon-2,3-dicarbonsaeureimid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |