DE1176668B - Verfahren zur Herstellung von 1-Alkylamino- oder Cycloalkylamino-4-brom- bzw. 1, 5-Di-(alkylamino- oder cycloalkylamino)-4, 8-dibromanthrachinonen - Google Patents
Verfahren zur Herstellung von 1-Alkylamino- oder Cycloalkylamino-4-brom- bzw. 1, 5-Di-(alkylamino- oder cycloalkylamino)-4, 8-dibromanthrachinonenInfo
- Publication number
- DE1176668B DE1176668B DEC28807A DEC0028807A DE1176668B DE 1176668 B DE1176668 B DE 1176668B DE C28807 A DEC28807 A DE C28807A DE C0028807 A DEC0028807 A DE C0028807A DE 1176668 B DE1176668 B DE 1176668B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- alkylamino
- cycloalkylamino
- hydrochloric acid
- bromine
- 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 11
- 125000006310 cycloalkyl amino group Chemical group 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 230000031709 bromination Effects 0.000 claims description 6
- 238000005893 bromination reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 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 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- -1 alkyl radical Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- IIPRUQZTMZETSL-UHFFFAOYSA-N 1-bromo-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC IIPRUQZTMZETSL-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- SVTDYSXXLJYUTM-UHFFFAOYSA-N disperse red 9 Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC SVTDYSXXLJYUTM-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 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 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- NRWJVAOAOUKRCS-UHFFFAOYSA-N 1,2-bis(methylamino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(NC)C(NC)=CC=C3C(=O)C2=C1 NRWJVAOAOUKRCS-UHFFFAOYSA-N 0.000 description 1
- YGOKTRWIJMNYPH-UHFFFAOYSA-N 1,5-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(NC)C=CC=C2C(=O)C2=C1C=CC=C2NC YGOKTRWIJMNYPH-UHFFFAOYSA-N 0.000 description 1
- QPPBADVBJDDEBZ-UHFFFAOYSA-N 1,5-dibromo-4,8-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(NC)C=CC(Br)=C2C(=O)C2=C1C(Br)=CC=C2NC QPPBADVBJDDEBZ-UHFFFAOYSA-N 0.000 description 1
- VLKHNXNEQXFXFS-UHFFFAOYSA-N 1-(1-hydroxyethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(O)C VLKHNXNEQXFXFS-UHFFFAOYSA-N 0.000 description 1
- BWQIGAJDKXZJTG-UHFFFAOYSA-N 1-(cyclohexylamino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1CCCCC1 BWQIGAJDKXZJTG-UHFFFAOYSA-N 0.000 description 1
- ATIYVSUEHXWMKF-UHFFFAOYSA-N 1-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(C)C ATIYVSUEHXWMKF-UHFFFAOYSA-N 0.000 description 1
- CFOFDTGGGLESBH-UHFFFAOYSA-N 1-bromo-4-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC(C)C CFOFDTGGGLESBH-UHFFFAOYSA-N 0.000 description 1
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical group Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone 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
- 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7062A CH444885A (de) | 1962-01-02 | 1962-01-02 | Verfahren zur Herstellung von bromierten Aminoanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1176668B true DE1176668B (de) | 1964-08-27 |
Family
ID=4178602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC28807A Pending DE1176668B (de) | 1962-01-02 | 1962-12-31 | Verfahren zur Herstellung von 1-Alkylamino- oder Cycloalkylamino-4-brom- bzw. 1, 5-Di-(alkylamino- oder cycloalkylamino)-4, 8-dibromanthrachinonen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE626554A (en:Method) |
| CH (1) | CH444885A (en:Method) |
| DE (1) | DE1176668B (en:Method) |
| ES (1) | ES283842A1 (en:Method) |
| GB (1) | GB957146A (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2817890A1 (de) * | 1977-04-25 | 1978-10-26 | Sumitomo Chemical Co | Verfahren zur herstellung von 1-amino- 2-brom-4-hydroxy-anthrachinon |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2459149A (en) * | 1945-06-01 | 1949-01-18 | Eastman Kodak Co | Anthraquinone compounds |
-
0
- BE BE626554D patent/BE626554A/xx unknown
-
1962
- 1962-01-02 CH CH7062A patent/CH444885A/de unknown
- 1962-11-16 GB GB4351262A patent/GB957146A/en not_active Expired
- 1962-12-31 DE DEC28807A patent/DE1176668B/de active Pending
- 1962-12-31 ES ES283842A patent/ES283842A1/es not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2459149A (en) * | 1945-06-01 | 1949-01-18 | Eastman Kodak Co | Anthraquinone compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
|---|---|
| ES283842A1 (es) | 1963-07-01 |
| CH444885A (de) | 1967-10-15 |
| GB957146A (en) | 1964-05-06 |
| BE626554A (en:Method) |
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