DE2149684A1 - Verfahren zur Herstellung von Chinacridonen - Google Patents
Verfahren zur Herstellung von ChinacridonenInfo
- Publication number
- DE2149684A1 DE2149684A1 DE19712149684 DE2149684A DE2149684A1 DE 2149684 A1 DE2149684 A1 DE 2149684A1 DE 19712149684 DE19712149684 DE 19712149684 DE 2149684 A DE2149684 A DE 2149684A DE 2149684 A1 DE2149684 A1 DE 2149684A1
- Authority
- DE
- Germany
- Prior art keywords
- slurry
- dihydroquinacridone
- anthraquinone
- oxidation
- quinacridone
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000002002 slurry Substances 0.000 claims description 34
- 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 claims description 28
- 230000003647 oxidation Effects 0.000 claims description 25
- 238000007254 oxidation reaction Methods 0.000 claims description 25
- 238000012986 modification Methods 0.000 claims description 24
- 239000013078 crystal Substances 0.000 claims description 22
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims description 21
- 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 claims description 17
- 230000004048 modification Effects 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- JAJIPIAHCFBEPI-UHFFFAOYSA-M 9,10-dioxoanthracene-1-sulfonate Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] JAJIPIAHCFBEPI-UHFFFAOYSA-M 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000002054 inoculum Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical group [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 238000002441 X-ray diffraction Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000000049 pigment Substances 0.000 description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 231100000989 no adverse effect Toxicity 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 3
- -1 ethoxylated acetylene glycol Chemical compound 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IJNPIHLZSZCGOC-UHFFFAOYSA-N 9,10-dioxoanthracene-1,8-disulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O IJNPIHLZSZCGOC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000012066 reaction slurry Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 description 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- 229920006384 Airco Polymers 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101150116986 THPO gene Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ZJXBEXRSXKGGHS-UHFFFAOYSA-N diethyl 2,5-dianilinocyclohexa-1,4-diene-1,4-dicarboxylate Chemical compound C1C(C(=O)OCC)=C(NC=2C=CC=CC=2)CC(C(=O)OCC)=C1NC1=CC=CC=C1 ZJXBEXRSXKGGHS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 238000009736 wetting 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
- C09B48/00—Quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7925470A | 1970-10-08 | 1970-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2149684A1 true DE2149684A1 (de) | 1972-04-13 |
Family
ID=22149389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712149684 Withdrawn DE2149684A1 (de) | 1970-10-08 | 1971-10-05 | Verfahren zur Herstellung von Chinacridonen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3738988A (enExample) |
| JP (1) | JPS551315B1 (enExample) |
| DE (1) | DE2149684A1 (enExample) |
| GB (1) | GB1349582A (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2325696A1 (fr) * | 1975-09-25 | 1977-04-22 | Du Pont | Preparation perfectionnee de quinacridone en utilisant du chlorure ferrique |
| EP0363759A3 (de) * | 1988-10-12 | 1991-09-04 | Bayer Ag | Verfahren zur Herstellung eines gegebenenfalls substituierten Chinacridons |
| EP0682090A1 (en) * | 1994-05-06 | 1995-11-15 | Bayer Corporation | Process for the preparation of quiacridone pigments |
| EP0716129A1 (en) * | 1994-12-06 | 1996-06-12 | Bayer Corporation | Process for the preparation of organic pigments |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873548A (en) * | 1971-05-06 | 1975-03-25 | Du Pont | 2,9-Dicarboxyquinacridone and methods for its production |
| JPS52111923A (en) * | 1976-03-16 | 1977-09-20 | Toyo Soda Mfg Co Ltd | Production of quinozolone derivative |
| US4247696A (en) * | 1978-04-01 | 1981-01-27 | Toyo Soda Manufacturing Co., Ltd. | Process for preparing gamma phase quinacridone |
| US4197404A (en) * | 1978-05-08 | 1980-04-08 | E. I. Du Pont De Nemours And Company | Preparation of γ-quinacridone pigment |
| JPS6062048A (ja) * | 1983-09-16 | 1985-04-10 | Seiko Instr & Electronics Ltd | 電子線マクロアナライザ |
| JPS6068541A (ja) * | 1983-09-21 | 1985-04-19 | Toyota Central Res & Dev Lab Inc | 擬似動態画像の撮影方法 |
| DE3605976A1 (de) * | 1986-02-25 | 1987-08-27 | Bayer Ag | Verfahren zur herstellung von 6,13-dihydrochinacridonen und chinacridonen |
| US5286863A (en) * | 1991-08-22 | 1994-02-15 | Ciba-Geigy Corporation | Oxidation process for preparing quinacridone pigments |
| JP3055365B2 (ja) * | 1993-06-30 | 2000-06-26 | 東洋インキ製造株式会社 | ２，５−ジ（アリールアミノ）−３，６−ジヒドロテレフタル酸ジアルキルエステル類の製造法およびこれを中間体とするキナクリドン類の製造法 |
| JPH07242836A (ja) * | 1993-11-19 | 1995-09-19 | Toyo Ink Mfg Co Ltd | ６，１３−ジヒドロキナクリドン類の製造方法およびこれを中間体とするキナクリドン類の製造方法 |
| US5502192A (en) * | 1994-08-08 | 1996-03-26 | Ciba-Geigy Corporation | Process for the preparation of quinacridones from dihydroquinacridones in an aqueous medium |
| DE69614058T2 (de) * | 1995-09-22 | 2002-03-21 | Ciba Speciality Chemicals Holding Inc., Basel | Verfahren zur Herstellung von Chinacridonen |
| EP0829523B1 (en) * | 1996-08-16 | 2001-09-12 | Ciba SC Holding AG | Oxidation process for preparing quinacridone pigments |
| US6313300B1 (en) | 1999-09-07 | 2001-11-06 | Ciba Specialty Chemicals Corp. | Oxidation process for preparing quinacridone pigments |
-
1970
- 1970-10-08 US US00079254A patent/US3738988A/en not_active Expired - Lifetime
-
1971
- 1971-10-05 DE DE19712149684 patent/DE2149684A1/de not_active Withdrawn
- 1971-10-06 JP JP7798671A patent/JPS551315B1/ja active Pending
- 1971-10-08 GB GB4688471A patent/GB1349582A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2325696A1 (fr) * | 1975-09-25 | 1977-04-22 | Du Pont | Preparation perfectionnee de quinacridone en utilisant du chlorure ferrique |
| EP0363759A3 (de) * | 1988-10-12 | 1991-09-04 | Bayer Ag | Verfahren zur Herstellung eines gegebenenfalls substituierten Chinacridons |
| EP0682090A1 (en) * | 1994-05-06 | 1995-11-15 | Bayer Corporation | Process for the preparation of quiacridone pigments |
| EP0716129A1 (en) * | 1994-12-06 | 1996-06-12 | Bayer Corporation | Process for the preparation of organic pigments |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1349582A (en) | 1974-04-03 |
| JPS551315B1 (enExample) | 1980-01-12 |
| US3738988A (en) | 1973-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |