DE1228274B - Herstellung von p-halogenierten alpha-Amino-anthrachinonen - Google Patents
Herstellung von p-halogenierten alpha-Amino-anthrachinonenInfo
- Publication number
- DE1228274B DE1228274B DEF45156A DEF0045156A DE1228274B DE 1228274 B DE1228274 B DE 1228274B DE F45156 A DEF45156 A DE F45156A DE F0045156 A DEF0045156 A DE F0045156A DE 1228274 B DE1228274 B DE 1228274B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- amino
- anthraquinone
- anthraquinones
- halogenated
- 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
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000460 chlorine Chemical group 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 230000026030 halogenation Effects 0.000 claims description 10
- 238000005658 halogenation reaction Methods 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- UKKFMBKKEFIJST-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carboximidamide Chemical class NC(=N)C1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O UKKFMBKKEFIJST-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
- AWACQBFBMROGQC-UHFFFAOYSA-N 1-amino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2N AWACQBFBMROGQC-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 2
- QWXDVWSEUJXVIK-UHFFFAOYSA-N 1,8-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N QWXDVWSEUJXVIK-UHFFFAOYSA-N 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- -1 1-amino-4-chloro-5-nitro-anthraquinone Chemical compound 0.000 description 2
- QIHMGEKACAOTPE-UHFFFAOYSA-N 1-amino-5-chloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2N QIHMGEKACAOTPE-UHFFFAOYSA-N 0.000 description 2
- PHZPGLMKVOOUGI-UHFFFAOYSA-N 1-amino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O PHZPGLMKVOOUGI-UHFFFAOYSA-N 0.000 description 2
- JMNNJCADZZBEOW-UHFFFAOYSA-N 1-amino-8-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2N JMNNJCADZZBEOW-UHFFFAOYSA-N 0.000 description 2
- CNSNLRXGBRBCAU-UHFFFAOYSA-N 5-amino-1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2N CNSNLRXGBRBCAU-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SZSXIUXAPZMWKU-UHFFFAOYSA-N 1,2,3-triaminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(N)=C2N SZSXIUXAPZMWKU-UHFFFAOYSA-N 0.000 description 1
- MKARJQUHEFPSDM-UHFFFAOYSA-N 1,4,5-triaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C=CC=C2N MKARJQUHEFPSDM-UHFFFAOYSA-N 0.000 description 1
- VIUAXWJVSABMEX-UHFFFAOYSA-N 1,5-diamino-4,8-dibromoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC(Br)=C2C(=O)C2=C1C(Br)=CC=C2N VIUAXWJVSABMEX-UHFFFAOYSA-N 0.000 description 1
- ARTKBKFNUMHVCU-UHFFFAOYSA-N 1,8-diamino-4,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(N)=C2C(=O)C2=C1C(Cl)=CC=C2N ARTKBKFNUMHVCU-UHFFFAOYSA-N 0.000 description 1
- PAIMZVRBBGMCRL-UHFFFAOYSA-N 1-(chloroamino)anthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCl PAIMZVRBBGMCRL-UHFFFAOYSA-N 0.000 description 1
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 description 1
- HVNFHSIIPHSECS-UHFFFAOYSA-N 1-amino-2,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC(Cl)=C2N HVNFHSIIPHSECS-UHFFFAOYSA-N 0.000 description 1
- RTSDLWXWHYMKGC-UHFFFAOYSA-N 1-amino-4,5,8-trichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2N RTSDLWXWHYMKGC-UHFFFAOYSA-N 0.000 description 1
- FNOSFXRVNZPYGJ-UHFFFAOYSA-N 1-amino-4,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C(Cl)=CC=C2N FNOSFXRVNZPYGJ-UHFFFAOYSA-N 0.000 description 1
- JOVRIPGYHSRFFR-UHFFFAOYSA-N 1-amino-4-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2N JOVRIPGYHSRFFR-UHFFFAOYSA-N 0.000 description 1
- YFEHGCGWUWOAFA-UHFFFAOYSA-N 1-amino-6,7-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=C(Cl)C=C2C(=O)C2=C1C=CC=C2N YFEHGCGWUWOAFA-UHFFFAOYSA-N 0.000 description 1
- CCEGIXWXBRNFOS-UHFFFAOYSA-N 1-amino-6-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)C2=C1C=CC=C2N CCEGIXWXBRNFOS-UHFFFAOYSA-N 0.000 description 1
- GGJNMALYBXOQEF-UHFFFAOYSA-N 1-amino-7-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=C(Cl)C=C2C(=O)C2=C1C=CC=C2N GGJNMALYBXOQEF-UHFFFAOYSA-N 0.000 description 1
- ZETPACCJSUWVHX-UHFFFAOYSA-N 4-amino-1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2N ZETPACCJSUWVHX-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical group C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 125000000909 amidinium group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- NGDNCZPCIZNCQS-UHFFFAOYSA-N ctk3j8699 Chemical compound Cl=S NGDNCZPCIZNCQS-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- VHSRXFVZNABKQE-UHFFFAOYSA-N sulfuric acid sulfurochloridic acid hydrate Chemical compound O.S(O)(O)(=O)=O.ClS(=O)(=O)O VHSRXFVZNABKQE-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- 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)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF45156A DE1228274B (de) | 1965-02-05 | 1965-02-05 | Herstellung von p-halogenierten alpha-Amino-anthrachinonen |
| LU50342A LU50342A1 (enExample) | 1965-02-05 | 1966-01-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF45156A DE1228274B (de) | 1965-02-05 | 1965-02-05 | Herstellung von p-halogenierten alpha-Amino-anthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1228274B true DE1228274B (de) | 1966-11-10 |
Family
ID=7100364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF45156A Pending DE1228274B (de) | 1965-02-05 | 1965-02-05 | Herstellung von p-halogenierten alpha-Amino-anthrachinonen |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1228274B (enExample) |
| LU (1) | LU50342A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758518A (en) * | 1964-09-29 | 1973-09-11 | Ciba Geigy Ag | Chlorinated alpha-aminoanthraquinones and process for their manufacture |
| DE2817890A1 (de) * | 1977-04-25 | 1978-10-26 | Sumitomo Chemical Co | Verfahren zur herstellung von 1-amino- 2-brom-4-hydroxy-anthrachinon |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1132931B (de) * | 1961-05-05 | 1962-07-12 | Basf Ag | Verfahren zur Reinigung von Aminoanthrachinonen |
| DE1154489B (de) * | 1961-05-05 | 1963-09-19 | Basf Ag | Verfahren zur Trennung von Mono- und Diaminoanthrachinonen |
-
1965
- 1965-02-05 DE DEF45156A patent/DE1228274B/de active Pending
-
1966
- 1966-01-27 LU LU50342A patent/LU50342A1/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1132931B (de) * | 1961-05-05 | 1962-07-12 | Basf Ag | Verfahren zur Reinigung von Aminoanthrachinonen |
| DE1154489B (de) * | 1961-05-05 | 1963-09-19 | Basf Ag | Verfahren zur Trennung von Mono- und Diaminoanthrachinonen |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758518A (en) * | 1964-09-29 | 1973-09-11 | Ciba Geigy Ag | Chlorinated alpha-aminoanthraquinones and process for their manufacture |
| DE2817890A1 (de) * | 1977-04-25 | 1978-10-26 | Sumitomo Chemical Co | Verfahren zur herstellung von 1-amino- 2-brom-4-hydroxy-anthrachinon |
Also Published As
| Publication number | Publication date |
|---|---|
| LU50342A1 (enExample) | 1966-03-28 |
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