GB1573256A - Process for preparing quinacridonequinone by oxidation of dihydroquinacridone - Google Patents
Process for preparing quinacridonequinone by oxidation of dihydroquinacridone Download PDFInfo
- Publication number
- GB1573256A GB1573256A GB6717/77A GB671777A GB1573256A GB 1573256 A GB1573256 A GB 1573256A GB 6717/77 A GB6717/77 A GB 6717/77A GB 671777 A GB671777 A GB 671777A GB 1573256 A GB1573256 A GB 1573256A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxidation
- dihydroquinacridone
- quinacridonequinone
- chlorate
- vanadium pentoxide
- 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
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 28
- 238000007254 oxidation reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical group [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 14
- KSLLMGLKCVSKFF-UHFFFAOYSA-N 5,12-dihydroquinolino[2,3-b]acridine-6,7,13,14-tetrone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C(=O)C(C(=O)C1=CC=CC=C1N1)=C1C2=O KSLLMGLKCVSKFF-UHFFFAOYSA-N 0.000 description 13
- YEIYQKSCDPOVNO-UHFFFAOYSA-N 5,8,9,12-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C(C=C2N3)=C1C=C2C(=O)C1=C3C=CCC1 YEIYQKSCDPOVNO-UHFFFAOYSA-N 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- -1 alkali metal chlorate Chemical class 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical group CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000012066 reaction slurry Substances 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- SNDAOXYSCAWUFQ-UHFFFAOYSA-N 5,6,12,13-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C2=C1CC(C(=O)C1=CC=CC=C1N1)=C1C2 SNDAOXYSCAWUFQ-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940005989 chlorate ion Drugs 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001052 yellow pigment 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
- C09B48/00—Quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/659,932 US4025518A (en) | 1976-02-20 | 1976-02-20 | Process for preparing quinacridonequinone by oxidation of dihydroquinacridone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1573256A true GB1573256A (en) | 1980-08-20 |
Family
ID=24647430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6717/77A Expired GB1573256A (en) | 1976-02-20 | 1977-02-17 | Process for preparing quinacridonequinone by oxidation of dihydroquinacridone |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4025518A (https=) |
| JP (1) | JPS5940169B2 (https=) |
| CH (1) | CH624975A5 (https=) |
| DE (1) | DE2706795C2 (https=) |
| FR (1) | FR2341579A1 (https=) |
| GB (1) | GB1573256A (https=) |
| MX (1) | MX146514A (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52111923A (en) * | 1976-03-16 | 1977-09-20 | Toyo Soda Mfg Co Ltd | Production of quinozolone derivative |
| DE3063338D1 (de) * | 1979-08-27 | 1983-07-07 | Du Pont | Process for preparing quinacridonequinone |
| DE3532343A1 (de) * | 1985-09-11 | 1987-03-19 | Hoechst Ag | Pigmente der chinacridonchinon-reihe, verfahren zu ihrer herstellung und ihre verwendung |
| DE3888443D1 (de) * | 1987-10-27 | 1994-04-21 | Basf Ag | Verfahren zur Herstellung von Dihydrochinacridonen, Chinacridonen und Chinacridonchinonen. |
| US6972333B2 (en) * | 2004-01-14 | 2005-12-06 | Sun Chemical Corporation | Preparation of quinacridonequinones and substituted derivatives of same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251845A (en) * | 1962-02-27 | 1966-05-17 | Du Pont | Process for oxidizing dihydroquinacridone to quinacridonequinone |
| US3185694A (en) * | 1962-09-17 | 1965-05-25 | Du Pont | Process for preparing quinacridonequinones |
| US3632588A (en) * | 1970-07-20 | 1972-01-04 | Du Pont | Oxidation of dihydroquinacridone |
-
1976
- 1976-02-20 US US05/659,932 patent/US4025518A/en not_active Expired - Lifetime
-
1977
- 1977-01-25 MX MX167815A patent/MX146514A/es unknown
- 1977-02-16 FR FR7704383A patent/FR2341579A1/fr not_active Withdrawn
- 1977-02-17 GB GB6717/77A patent/GB1573256A/en not_active Expired
- 1977-02-17 JP JP52015598A patent/JPS5940169B2/ja not_active Expired
- 1977-02-17 DE DE2706795A patent/DE2706795C2/de not_active Expired
- 1977-02-18 CH CH206677A patent/CH624975A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2706795C2 (de) | 1987-03-12 |
| CH624975A5 (https=) | 1981-08-31 |
| DE2706795A1 (de) | 1977-09-01 |
| FR2341579A1 (fr) | 1977-09-16 |
| MX146514A (es) | 1982-07-07 |
| JPS5940169B2 (ja) | 1984-09-28 |
| JPS52102333A (en) | 1977-08-27 |
| US4025518A (en) | 1977-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930217 |