DE1768333A1 - Verfahren zur Herstellung von 1-Brom-4-acylaminoanthrachinonen - Google Patents
Verfahren zur Herstellung von 1-Brom-4-acylaminoanthrachinonenInfo
- Publication number
- DE1768333A1 DE1768333A1 DE19681768333 DE1768333A DE1768333A1 DE 1768333 A1 DE1768333 A1 DE 1768333A1 DE 19681768333 DE19681768333 DE 19681768333 DE 1768333 A DE1768333 A DE 1768333A DE 1768333 A1 DE1768333 A1 DE 1768333A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- bromine
- water
- mixture
- bromo
- 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
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 65
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 63
- 229910052794 bromium Inorganic materials 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 18
- 230000031709 bromination Effects 0.000 claims description 17
- 238000005893 bromination reaction Methods 0.000 claims description 17
- KOJOUCAVSDKDPR-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)benzamide Chemical class C=1C=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=1NC(=O)C1=CC=CC=C1 KOJOUCAVSDKDPR-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 8
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 3
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 38
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- 238000003756 stirring Methods 0.000 description 26
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- -1 heterocyclic carboxylic acids Chemical class 0.000 description 11
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- JKRCBOYQTINLRS-UHFFFAOYSA-N n-(4-bromo-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Br)=CC=C1NC(=O)C1=CC=CC=C1 JKRCBOYQTINLRS-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- WDJHNJSBPXRITJ-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)acetamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C WDJHNJSBPXRITJ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- LRZQPQJEYDUCKH-UHFFFAOYSA-N n-(6-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1NC(=O)C1=CC=CC=C1 LRZQPQJEYDUCKH-UHFFFAOYSA-N 0.000 description 2
- VGSMPPZALKNNJT-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O VGSMPPZALKNNJT-UHFFFAOYSA-N 0.000 description 2
- ZARKDHHMWOCDPM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O ZARKDHHMWOCDPM-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- RQFIRASFBSDTDA-UHFFFAOYSA-N 2-amino-1-benzoylanthracene-9,10-dione Chemical class NC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1C(=O)C1=CC=CC=C1 RQFIRASFBSDTDA-UHFFFAOYSA-N 0.000 description 1
- OXTNQKFXUFNLGY-UHFFFAOYSA-N 2-chloro-n-(9,10-dioxoanthracen-1-yl)benzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O OXTNQKFXUFNLGY-UHFFFAOYSA-N 0.000 description 1
- ZOIHMUYZQODNEB-UHFFFAOYSA-N 4-chloro-n-(9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O ZOIHMUYZQODNEB-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CMRQJVYJXPEDBO-UHFFFAOYSA-N N-(5-chloro-9,10-dioxoanthracen-1-yl)-2-fluorobenzamide Chemical compound ClC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC(C1=C(C=CC=C1)F)=O)=O CMRQJVYJXPEDBO-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HIWMEFUFIRTVOZ-UHFFFAOYSA-N ethyl N-[4,8-dibromo-5-(ethoxycarbonylamino)-9,10-dioxoanthracen-1-yl]carbamate Chemical compound BrC1=CC=C(C=2C(C3=C(C=CC(=C3C(C12)=O)NC(=O)OCC)Br)=O)NC(=O)OCC HIWMEFUFIRTVOZ-UHFFFAOYSA-N 0.000 description 1
- WOKZFJICKMOZLE-UHFFFAOYSA-N ethyl n-(9,10-dioxoanthracen-1-yl)carbamate Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)OCC WOKZFJICKMOZLE-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IEFIRFASAAHCOS-UHFFFAOYSA-N n-(4-bromo-9,10-dioxoanthracen-1-yl)acetamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC(=O)C IEFIRFASAAHCOS-UHFFFAOYSA-N 0.000 description 1
- DORCRAXPUWOWPM-UHFFFAOYSA-N n-(5-acetamido-4,8-dibromo-9,10-dioxoanthracen-1-yl)acetamide Chemical compound O=C1C2=C(NC(C)=O)C=CC(Br)=C2C(=O)C2=C1C(Br)=CC=C2NC(=O)C DORCRAXPUWOWPM-UHFFFAOYSA-N 0.000 description 1
- VDCUNNJIPITONP-UHFFFAOYSA-N n-(5-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(Cl)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 VDCUNNJIPITONP-UHFFFAOYSA-N 0.000 description 1
- ZECJHXJLPDOKHF-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-2-fluorobenzamide Chemical compound FC1=CC=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O ZECJHXJLPDOKHF-UHFFFAOYSA-N 0.000 description 1
- UEEBUOUIWYBECI-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C=CC=2)=C1 UEEBUOUIWYBECI-UHFFFAOYSA-N 0.000 description 1
- IRDGVQANOHDRRG-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O IRDGVQANOHDRRG-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- 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
-
- 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
- C09B1/36—Dyes with acylated amino groups
-
- 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
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH655367A CH483396A (de) | 1967-05-09 | 1967-05-09 | Verfahren zur Herstellung von 1-Brom-4-acylamino-anthrachinonen |
| CH970467A CH505784A (de) | 1967-05-09 | 1967-07-07 | Verfahren zur Herstellung von 1-Brom-4-acylaminoanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768333A1 true DE1768333A1 (de) | 1971-06-03 |
Family
ID=25699766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768333 Pending DE1768333A1 (de) | 1967-05-09 | 1968-05-02 | Verfahren zur Herstellung von 1-Brom-4-acylaminoanthrachinonen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3804863A (en:Method) |
| BE (1) | BE714864A (en:Method) |
| CH (2) | CH483396A (en:Method) |
| DE (1) | DE1768333A1 (en:Method) |
| FR (1) | FR1574809A (en:Method) |
| GB (1) | GB1177869A (en:Method) |
| IT (1) | IT943040B (en:Method) |
| NL (1) | NL6806502A (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2130596B (en) * | 1982-11-12 | 1987-06-10 | Ivaschenko Alexandr V | Anthraquinone derivatives method for preparing same liquid-crystal material for electrooptical devices and electrooptical device |
| EP0368750B1 (en) * | 1988-11-10 | 1994-10-26 | Sumitomo Chemical Company Limited | Process for preparing substituted aminoanthraquinones |
-
1967
- 1967-05-09 CH CH655367A patent/CH483396A/de not_active IP Right Cessation
- 1967-07-07 CH CH970467A patent/CH505784A/de unknown
-
1968
- 1968-04-29 FR FR1574809D patent/FR1574809A/fr not_active Expired
- 1968-05-02 DE DE19681768333 patent/DE1768333A1/de active Pending
- 1968-05-07 IT IT36784/68A patent/IT943040B/it active
- 1968-05-08 BE BE714864D patent/BE714864A/xx unknown
- 1968-05-08 NL NL6806502A patent/NL6806502A/xx unknown
- 1968-05-09 GB GB22054/68A patent/GB1177869A/en not_active Expired
-
1971
- 1971-06-07 US US00150943A patent/US3804863A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1177869A (en) | 1970-01-14 |
| IT943040B (it) | 1973-04-02 |
| US3804863A (en) | 1974-04-16 |
| BE714864A (en:Method) | 1968-11-08 |
| CH505784A (de) | 1971-04-15 |
| FR1574809A (en:Method) | 1969-07-18 |
| NL6806502A (en:Method) | 1968-11-11 |
| CH483396A (de) | 1969-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1029506B (de) | Verfahren zur Herstellung von Farbstoffen fuer synthetische Fasern | |
| DE2524748B2 (de) | Verfahren zur Herstellung von 1 ^-Diaminoanthrachinon^-dinitril | |
| DE1768333A1 (de) | Verfahren zur Herstellung von 1-Brom-4-acylaminoanthrachinonen | |
| DE2259329C2 (de) | Verfahren zur Herstellung von Anthrachinonoxazolen | |
| DE1795102C2 (de) | Verfahren zur Herstellung stickstoffhaltiger aromatischer Verbindungen | |
| DE1493566A1 (de) | Verfahren zur Chlorierung von alpha-Aminoanthrachinonen | |
| DE1493566C3 (de) | Verfahren zur Chlorierung von a-Aminoanthrachinonen | |
| DE889750C (de) | Verfahren zur Herstellung von Zwischenprodukten der Anthrachinonreihe | |
| DE1228274B (de) | Herstellung von p-halogenierten alpha-Amino-anthrachinonen | |
| DE1929808A1 (de) | Verfahren zur Herstellung von 1,8-Dihydroxy-4,5-dinitro- und diaminoanthrachinonbrom- und -chlorverbindungen | |
| EP0375990B1 (de) | Verfahren zur Herstellung von 1-Amino-2-brom-4-hydroxy-anthrachinon | |
| DE1127911B (de) | Verfahren zur Herstellung von 1-Amino-2-(ªÏ-mono- und -dichlor- oder -bromacetyl)-anthrachinonen | |
| DE1793151C (de) | Verfahren zur Herstellung von in alpha-Stellung chlorierten Anthrachönonderivaten | |
| US1963109A (en) | Preparation of halogenated benzoyl-amino-anthraquinone | |
| DE1173907B (de) | Verfahren zur Herstellung von 1, 4-Diamino-5, 8-dichlor-anthrachinonen | |
| DE1543605C3 (de) | Verfahren zur Herstellung von Amino-Anthrachinonen | |
| DE1135495B (de) | Verfahren zur Reinigung von 1-Amino-anthrachinon-2-sulfonsaeuren | |
| DE2460687C3 (de) | Verfahren zur Herstellung von 1-Aminoanthrachinon | |
| AT48028B (de) | Verfahren zur Darstellung von Halogenderivaten der Indigoreihe. | |
| DE487595C (de) | Verfahren zur Erzeugung hochchlorierter Perylene | |
| DE254622C (en:Method) | ||
| DE352719C (de) | Verfahren zur Gewinnung des sym. Oktohydrophenanthrens | |
| DE656944C (de) | Verfahren zur Herstellung von N-Dihydro-1, 2, 2', 1'-anthrachinonazin und seinen Abkoemmlingen | |
| DE2631833B2 (de) | Verfahren zur Herstellung von 3- Brom-benz [d,e] -anthron durch Bromierung von Benzanthron | |
| DE1154490B (de) | Verfahren zur Herstellung von Chlor-amino-anthrachinonen |