DE2105286A1 - Verfahren zur Herstellung von Flavanthronen - Google Patents
Verfahren zur Herstellung von FlavanthronenInfo
- Publication number
- DE2105286A1 DE2105286A1 DE19712105286 DE2105286A DE2105286A1 DE 2105286 A1 DE2105286 A1 DE 2105286A1 DE 19712105286 DE19712105286 DE 19712105286 DE 2105286 A DE2105286 A DE 2105286A DE 2105286 A1 DE2105286 A1 DE 2105286A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- copper
- flavanthrones
- bromo
- process according
- 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 18
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 18
- 229910052802 copper Inorganic materials 0.000 claims description 14
- 239000010949 copper Substances 0.000 claims description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- INPPNPYTEFTFQG-UHFFFAOYSA-N 2-amino-1-bromoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(Br)C(N)=CC=C3C(=O)C2=C1 INPPNPYTEFTFQG-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
- -1 1-bromo-2-amino-3-methoxyanthraquinone Chemical compound 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZDNLBGNACWKHAX-UHFFFAOYSA-N 2-amino-1,3-dibromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Br)C(N)=C(Br)C=C3C(=O)C2=C1 ZDNLBGNACWKHAX-UHFFFAOYSA-N 0.000 description 2
- PLGPRGMWHYWEFT-UHFFFAOYSA-N 2-amino-1-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(N)=CC=C3C(=O)C2=C1 PLGPRGMWHYWEFT-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- IAHOXFDIXYBPBM-UHFFFAOYSA-N 2-amino-1-bromo-3-methylanthracene-9,10-dione Chemical compound BrC1=C(C(=CC=2C(C3=CC=CC=C3C(C12)=O)=O)C)N IAHOXFDIXYBPBM-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl 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
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- IBHWREHFNDMRPR-UHFFFAOYSA-N phloroglucinol carboxylic acid Natural products OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YTWOHSWDLJUCRK-UHFFFAOYSA-N thiolane 1,1-dioxide Chemical compound O=S1(=O)CCCC1.O=S1(=O)CCCC1 YTWOHSWDLJUCRK-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000003021 water soluble solvent 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/20—Flavanthrones
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 |
|---|---|---|---|
| CH198970A CH541604A (de) | 1970-02-11 | 1970-02-11 | Verfahren zur Herstellung von Flavanthronen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2105286A1 true DE2105286A1 (de) | 1971-08-19 |
Family
ID=4223305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712105286 Pending DE2105286A1 (de) | 1970-02-11 | 1971-02-04 | Verfahren zur Herstellung von Flavanthronen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3720678A (OSRAM) |
| BE (1) | BE762731A (OSRAM) |
| BR (1) | BR7100763D0 (OSRAM) |
| CA (1) | CA947284A (OSRAM) |
| CH (1) | CH541604A (OSRAM) |
| DE (1) | DE2105286A1 (OSRAM) |
| FR (1) | FR2074360A5 (OSRAM) |
| GB (1) | GB1278914A (OSRAM) |
| NL (1) | NL7101763A (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2748860C2 (de) * | 1977-10-31 | 1979-10-31 | Basf Ag, 6700 Ludwigshafen | Verfahren zur direkten Überführung von rohem Flavanthron in eine lasierende Pigmentform |
| DE3663951D1 (en) * | 1985-04-01 | 1989-07-20 | Ciba Geigy Ag | Process for the preparation of anthraquinone imide compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191202949A (en) * | 1911-07-11 | 1912-08-22 | Fritz Ullmann | Manufacture of Vat Dyestuffs of the Anthracene Series. |
| DE512821C (de) * | 1926-05-26 | 1930-11-20 | Scottish Dyes Ltd | Verfahren zur Herstellung von 1, 1-Dianthrachinonyl-2, 2-diurethan, seinen Derivaten und gegebenenfalls Kondensationsprodukten |
| US1714249A (en) * | 1926-05-26 | 1929-05-21 | Scottish Dyes Ltd | Process of preparing flavanthrone |
| CH159670A (de) * | 1930-12-11 | 1933-01-31 | Ig Farbenindustrie Ag | Verfahren zur Darstellung von Flavanthren. |
| US2068312A (en) * | 1933-05-24 | 1937-01-19 | Du Pont | Halogen-amino-flavanthrones and process of producing the same |
| US2685582A (en) * | 1946-08-23 | 1954-08-03 | Ici Ltd | Manufacture of dyestuffs |
| US3660407A (en) * | 1969-06-02 | 1972-05-02 | Pfizer | Purification of flavanthrone yellow pigment |
-
1970
- 1970-02-11 CH CH198970A patent/CH541604A/de not_active IP Right Cessation
- 1970-12-28 FR FR7046881A patent/FR2074360A5/fr not_active Expired
-
1971
- 1971-01-15 CA CA102807A patent/CA947284A/en not_active Expired
- 1971-01-21 US US00108602A patent/US3720678A/en not_active Expired - Lifetime
- 1971-02-04 DE DE19712105286 patent/DE2105286A1/de active Pending
- 1971-02-10 BE BE762731A patent/BE762731A/xx unknown
- 1971-02-10 NL NL7101763A patent/NL7101763A/xx unknown
- 1971-03-01 BR BR763/71A patent/BR7100763D0/pt unknown
- 1971-04-19 GB GB20400/71A patent/GB1278914A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7100763D0 (pt) | 1973-05-03 |
| GB1278914A (en) | 1972-06-21 |
| US3720678A (en) | 1973-03-13 |
| FR2074360A5 (OSRAM) | 1971-10-01 |
| CA947284A (en) | 1974-05-14 |
| BE762731A (fr) | 1971-08-10 |
| NL7101763A (OSRAM) | 1971-08-13 |
| CH541604A (de) | 1973-09-15 |
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