DE2746000C2 - Verfahren zur Herstellung von Bis-triazolylstilbenen - Google Patents
Verfahren zur Herstellung von Bis-triazolylstilbenenInfo
- Publication number
- DE2746000C2 DE2746000C2 DE2746000A DE2746000A DE2746000C2 DE 2746000 C2 DE2746000 C2 DE 2746000C2 DE 2746000 A DE2746000 A DE 2746000A DE 2746000 A DE2746000 A DE 2746000A DE 2746000 C2 DE2746000 C2 DE 2746000C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- formula
- water
- urea
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 16
- UIACIUMOCZUZSC-UHFFFAOYSA-N 4-[1,2-diphenyl-2-(2h-triazol-4-yl)ethenyl]-2h-triazole Chemical class C1=NNN=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=NNN=C1 UIACIUMOCZUZSC-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004202 carbamide Substances 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MLNKXLRYCLKJSS-RMKNXTFCSA-N (2e)-2-hydroxyimino-1-phenylethanone Chemical compound O\N=C\C(=O)C1=CC=CC=C1 MLNKXLRYCLKJSS-RMKNXTFCSA-N 0.000 description 3
- UFBOIWPLCDSNEG-OWOJBTEDSA-N 5-hydrazinyl-2-[(e)-2-(4-hydrazinyl-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(NN)=CC=C1\C=C\C1=CC=C(NN)C=C1S(O)(=O)=O UFBOIWPLCDSNEG-OWOJBTEDSA-N 0.000 description 3
- -1 anhydrides carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FPMFMXSSJXIJEC-UHFFFAOYSA-N N1N=NC(=C1)C(=C(C1=C(C(=CC=C1)S(=O)(=O)O)S(=O)(=O)O)C=1N=NNC1)C1=CC=CC=C1 Chemical class N1N=NC(=C1)C(=C(C1=C(C(=CC=C1)S(=O)(=O)O)S(=O)(=O)O)C=1N=NNC1)C1=CC=CC=C1 FPMFMXSSJXIJEC-UHFFFAOYSA-N 0.000 description 2
- WLUGNJMEBFZDKB-UHFFFAOYSA-N ON=NN=C1C(C(=C(C(=C1)C=CC1=CC=CC=C1)S(=O)(=O)O)S(=O)(=O)O)=NN=NO Chemical class ON=NN=C1C(C(=C(C(=C1)C=CC1=CC=CC=C1)S(=O)(=O)O)S(=O)(=O)O)=NN=NO WLUGNJMEBFZDKB-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- HSTDHICJRITDGJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-hydroxyiminoethanone Chemical compound ON=CC(=O)C1=CC=C(Cl)C=C1 HSTDHICJRITDGJ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical group COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- OLFNMQURIWJIAS-UHFFFAOYSA-N 2-hydroxyimino-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C=NO)C=C1 OLFNMQURIWJIAS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RDCOMWQFSWWPJG-UHFFFAOYSA-N acetyl acetate;formic acid Chemical compound OC=O.CC(=O)OC(C)=O RDCOMWQFSWWPJG-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- PASJSRFXRHDERE-UHFFFAOYSA-N methyl N-hydroxy-2-oxo-2-phenylethanimidate Chemical compound COC(C(=O)C1=CC=CC=C1)=NO PASJSRFXRHDERE-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000005646 oximino group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2746000A DE2746000C2 (de) | 1977-10-13 | 1977-10-13 | Verfahren zur Herstellung von Bis-triazolylstilbenen |
| IN669/DEL/78A IN148571B (cg-RX-API-DMAC7.html) | 1977-10-13 | 1978-09-12 | |
| EP78101043A EP0001582B1 (de) | 1977-10-13 | 1978-09-30 | Verfahren zur Herstellung von Bis-triazolylstilbenen |
| DE7878101043T DE2860090D1 (en) | 1977-10-13 | 1978-09-30 | Process for the preparation of bis-triazolyl stilbenes |
| US05/950,438 US4217449A (en) | 1977-10-13 | 1978-10-11 | Process for the preparation of bis-triazolylstilbenes |
| JP12423178A JPS5464528A (en) | 1977-10-13 | 1978-10-11 | Method of making bistriazorylstilben |
| IT7828656A IT7828656A0 (it) | 1977-10-13 | 1978-10-11 | Procedimento per la preparazione di bis-triazolil-stilbeni. |
| ES474133A ES474133A1 (es) | 1977-10-13 | 1978-10-11 | Procedimiento para la obtencion de compuestos de bis-triazo-lilestilbeno. |
| BR7806745A BR7806745A (pt) | 1977-10-13 | 1978-10-12 | Processo para a preparacao de bis-triazolilestilbenos |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2746000A DE2746000C2 (de) | 1977-10-13 | 1977-10-13 | Verfahren zur Herstellung von Bis-triazolylstilbenen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2746000B1 DE2746000B1 (de) | 1978-07-06 |
| DE2746000C2 true DE2746000C2 (de) | 1979-03-15 |
Family
ID=6021319
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2746000A Expired DE2746000C2 (de) | 1977-10-13 | 1977-10-13 | Verfahren zur Herstellung von Bis-triazolylstilbenen |
| DE7878101043T Expired DE2860090D1 (en) | 1977-10-13 | 1978-09-30 | Process for the preparation of bis-triazolyl stilbenes |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7878101043T Expired DE2860090D1 (en) | 1977-10-13 | 1978-09-30 | Process for the preparation of bis-triazolyl stilbenes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4217449A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0001582B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5464528A (cg-RX-API-DMAC7.html) |
| BR (1) | BR7806745A (cg-RX-API-DMAC7.html) |
| DE (2) | DE2746000C2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES474133A1 (cg-RX-API-DMAC7.html) |
| IN (1) | IN148571B (cg-RX-API-DMAC7.html) |
| IT (1) | IT7828656A0 (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3019521A1 (de) * | 1980-05-22 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von v-triazolverbindungen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670914C3 (de) * | 1967-08-23 | 1978-05-03 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Aryl-v-triazolen |
| DE1670999C3 (de) * | 1968-03-16 | 1979-03-15 | Bayer Ag, 5090 Leverkusen | Triazolyl-cumarine |
| DE2210261C3 (de) * | 1972-03-03 | 1980-02-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Aryl-v-triazolen |
| DE2242784C3 (de) * | 1972-08-31 | 1978-09-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Aryl-v-triazolen |
| IN139845B (cg-RX-API-DMAC7.html) * | 1972-11-06 | 1976-08-07 | Bayer Ag | |
| DE2338881C3 (de) * | 1973-08-01 | 1980-08-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2-Aryl-vic-Triazolen |
| DE2254300A1 (de) * | 1972-11-06 | 1974-05-09 | Bayer Ag | Verfahren zur herstellung von 2-arylvic-triazolen |
| CH587831A5 (cg-RX-API-DMAC7.html) * | 1973-05-17 | 1977-05-13 | Sandoz Ag |
-
1977
- 1977-10-13 DE DE2746000A patent/DE2746000C2/de not_active Expired
-
1978
- 1978-09-12 IN IN669/DEL/78A patent/IN148571B/en unknown
- 1978-09-30 DE DE7878101043T patent/DE2860090D1/de not_active Expired
- 1978-09-30 EP EP78101043A patent/EP0001582B1/de not_active Expired
- 1978-10-11 US US05/950,438 patent/US4217449A/en not_active Expired - Lifetime
- 1978-10-11 JP JP12423178A patent/JPS5464528A/ja active Granted
- 1978-10-11 ES ES474133A patent/ES474133A1/es not_active Expired
- 1978-10-11 IT IT7828656A patent/IT7828656A0/it unknown
- 1978-10-12 BR BR7806745A patent/BR7806745A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN148571B (cg-RX-API-DMAC7.html) | 1981-04-04 |
| DE2746000B1 (de) | 1978-07-06 |
| BR7806745A (pt) | 1979-05-08 |
| ES474133A1 (es) | 1979-05-01 |
| EP0001582B1 (de) | 1980-07-23 |
| JPS5464528A (en) | 1979-05-24 |
| DE2860090D1 (en) | 1980-11-13 |
| IT7828656A0 (it) | 1978-10-11 |
| JPS6228138B2 (cg-RX-API-DMAC7.html) | 1987-06-18 |
| US4217449A (en) | 1980-08-12 |
| EP0001582A1 (de) | 1979-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |