DE2611545A1 - Verfahren zur herstellung von kupferphthalocyanin - Google Patents
Verfahren zur herstellung von kupferphthalocyaninInfo
- Publication number
- DE2611545A1 DE2611545A1 DE19762611545 DE2611545A DE2611545A1 DE 2611545 A1 DE2611545 A1 DE 2611545A1 DE 19762611545 DE19762611545 DE 19762611545 DE 2611545 A DE2611545 A DE 2611545A DE 2611545 A1 DE2611545 A1 DE 2611545A1
- Authority
- DE
- Germany
- Prior art keywords
- urea
- phthalic anhydride
- reactor
- copper salt
- catalyst
- 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- Withdrawn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 20
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001879 copper Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 150000003021 phthalic acid derivatives Chemical class 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- CHCFOMQHQIQBLZ-UHFFFAOYSA-N azane;phthalic acid Chemical compound N.N.OC(=O)C1=CC=CC=C1C(O)=O CHCFOMQHQIQBLZ-UHFFFAOYSA-N 0.000 description 1
- -1 benzene radical Chemical class 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000013589 supplement 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762611545 DE2611545A1 (de) | 1976-03-18 | 1976-03-18 | Verfahren zur herstellung von kupferphthalocyanin |
| CH323277A CH624701A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-03-18 | 1977-03-15 | |
| BE175830A BE852522A (fr) | 1976-03-18 | 1977-03-16 | Procede pour produire de la phtalocyanine de cuivre |
| GB11112/77A GB1541515A (en) | 1976-03-18 | 1977-03-16 | Process for the preparation of copper phthalocyanine |
| JP2812577A JPS52112628A (en) | 1976-03-18 | 1977-03-16 | Process for manufacture of copper phthalocyanine |
| US05/778,117 US4102892A (en) | 1976-03-18 | 1977-03-16 | Process for the preparation of copper phthylocyanine |
| ES456923A ES456923A1 (es) | 1976-03-18 | 1977-03-17 | Procedimiento para la obtencion de ftalocianina de cobre. |
| BR7701632A BR7701632A (pt) | 1976-03-18 | 1977-03-17 | Processo para a preparacao de fialocianina de cobre |
| DK117077A DK117077A (da) | 1976-03-18 | 1977-03-17 | Fremgangsmade til fremstilling af kobberphthalocyanin |
| FR7708235A FR2344601A1 (fr) | 1976-03-18 | 1977-03-18 | Procede pour produire de la phtalocyanine de cuivre |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762611545 DE2611545A1 (de) | 1976-03-18 | 1976-03-18 | Verfahren zur herstellung von kupferphthalocyanin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2611545A1 true DE2611545A1 (de) | 1977-09-22 |
Family
ID=5972837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762611545 Withdrawn DE2611545A1 (de) | 1976-03-18 | 1976-03-18 | Verfahren zur herstellung von kupferphthalocyanin |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5725361A (en) * | 1980-07-23 | 1982-02-10 | Kawasaki Kasei Chem Ltd | Production of copper phthalocyanine and/or derivative thereof |
| US4320059A (en) * | 1980-11-10 | 1982-03-16 | American Cyanamid Company | Process for the manufacture of phthalocyanines |
| JPS57170961A (en) * | 1981-04-16 | 1982-10-21 | Kawasaki Kasei Chem Ltd | Production of copper phthalocyanine and/or its derivative |
| JPH04126873U (ja) * | 1991-05-02 | 1992-11-18 | 溶明 田原 | 多用途印鑑 |
| US9919957B2 (en) | 2016-01-19 | 2018-03-20 | Unifrax I Llc | Inorganic fiber |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1483417A (en) * | 1974-07-06 | 1977-08-17 | Bayer Ag | Process for the preparation and conditioning of copper phthalocyanine |
| DE2432564A1 (de) * | 1974-07-06 | 1976-01-22 | Bayer Ag | Verfahren zur herstellung von kupferphthalocyanin |
-
1976
- 1976-03-18 DE DE19762611545 patent/DE2611545A1/de not_active Withdrawn
-
1977
- 1977-03-15 CH CH323277A patent/CH624701A5/de not_active IP Right Cessation
- 1977-03-16 US US05/778,117 patent/US4102892A/en not_active Expired - Lifetime
- 1977-03-16 GB GB11112/77A patent/GB1541515A/en not_active Expired
- 1977-03-16 JP JP2812577A patent/JPS52112628A/ja active Pending
- 1977-03-16 BE BE175830A patent/BE852522A/xx unknown
- 1977-03-17 BR BR7701632A patent/BR7701632A/pt unknown
- 1977-03-17 ES ES456923A patent/ES456923A1/es not_active Expired
- 1977-03-17 DK DK117077A patent/DK117077A/da unknown
- 1977-03-18 FR FR7708235A patent/FR2344601A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US4102892A (en) | 1978-07-25 |
| GB1541515A (en) | 1979-03-07 |
| CH624701A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-08-14 |
| DK117077A (da) | 1977-09-19 |
| BR7701632A (pt) | 1977-11-08 |
| FR2344601A1 (fr) | 1977-10-14 |
| JPS52112628A (en) | 1977-09-21 |
| BE852522A (fr) | 1977-09-16 |
| ES456923A1 (es) | 1978-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |