CN105131002A - Synthetic method of unsubstituted cobalt phthalocyanine - Google Patents
Synthetic method of unsubstituted cobalt phthalocyanine Download PDFInfo
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- CN105131002A CN105131002A CN201510526852.9A CN201510526852A CN105131002A CN 105131002 A CN105131002 A CN 105131002A CN 201510526852 A CN201510526852 A CN 201510526852A CN 105131002 A CN105131002 A CN 105131002A
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- synthetic method
- cobalt phthalocyanine
- cobalt
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- phthalic nitrile
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to a synthetic method of unsubstituted cobalt phthalocyanine. The synthetic method is characterized by comprising the steps of using metallic cobalt salt and phthalic nitrile as raw materials, using DMF as a solvent, and performing a reaction of the metallic cobalt salt and the phthalic nitrile in the DMF at the temperature of 130-170 DEG C in a hydrothermal reaction kettle so as to obtain target products. The synthetic method disclosed by the invention is low in reacting temperature and short in reacting time, does not need any catalysts; and the method is simple, low in production cost, high in yield and purity and good in repeatability, so that the synthetic method can meet requirements for large-scale industrial production.
Description
Technical field
The invention belongs to the field of chemical synthesis, particularly relating to a kind of method of synthesizing without replacing cobalt phthalocyanine.
Background technology
Metal phthalocyanine is the symmetrical title complex of the planar conjugate aroma system with 18 π-electrons, has the stability of height, the handiness of structure and good spectrum characteristic.Within 1907, chanced in an experiment by Braun and Tchemiac of Britain, apart from modern existing century-old many history.This compounds is very important kind in organic synthesis pigment, and they have excellent look strong and fastness, are applied in the fields such as plastics, coating and ink widely, and are the important source material of producing electrophotographic photoconductor, CD etc.At present, the preparation method of phthalocyanine mainly contains three kinds: ammonium molybdate solid catalysis method, inert solvent method and DBU liquid catalytic.But these three kinds of methods not only all need to add catalyzer, temperature of reaction is higher, the reaction times is longer, and method of purification is complicated.Therefore, developing a kind of simple, economic, efficient novel method is very necessary to prepare metal phthalocyanine to meet the need of market.
Summary of the invention
The object of the present invention is to provide a kind of novel method of synthesizing without replacing cobalt phthalocyanine, from the angle of economy and environmental protection, simplifying synthesis step, optimizing reaction system, reducing the production cost without replacing cobalt phthalocyanine.
For achieving the above object, the technical solution used in the present invention is: a kind of synthetic method without replacing cobalt phthalocyanine: with Cobalt salts and phthalic nitrile for raw material, with DMF (DMF) for solvent, without the need to adding any catalyzer, synthesized by hydrothermal synthesis method; Described is as follows without the chemical structural formula replacing cobalt phthalocyanine:
The above-mentioned synthetic method without replacement cobalt phthalocyanine, adds in DMF successively by Cobalt salts and phthalic nitrile, and in 130-170 DEG C, reaction 2-6h, is cooled to room temperature, adds organic solvent, suction filtration.
The above-mentioned synthetic method without replacement cobalt phthalocyanine, in molar ratio, Cobalt salts: phthalic nitrile=1:3-5.Preferably, Cobalt salts: phthalic nitrile=1:4.
The above-mentioned synthetic method without replacement cobalt phthalocyanine, described Cobalt salts is Cobalt diacetate tetrahydrate, CoCL2 6H2O or heptahydrate.Preferably, Cobalt salts is Cobalt diacetate tetrahydrate.
The above-mentioned synthetic method without replacement cobalt phthalocyanine, described organic solvent is ether, acetone or ethyl acetate.Preferably, organic solvent is ether.
The above-mentioned synthetic method without replacement cobalt phthalocyanine, comprise purification step, described purification is: after suction filtration, gets precipitation, and precipitation uses methylene dichloride repetitive scrubbing.
Synthetic route of the present invention is as follows:
The invention has the beneficial effects as follows:
1. the present invention, simple without the synthetic method replacing cobalt phthalocyanine, do not need to add any catalyzer, temperature of reaction is low, time is short, easy to operate, does not need regulating and controlling temperature, low production cost, productive rate is high, and product purity is high and reproducible, makes the requirement of its applicable scale operation.
2. the present invention, method of purification is simple, and adding ether has a large amount of solid to separate out, and by crude product washed with dichloromethane, suction filtration can obtain pure product.
3. the present invention, reacts raw materials used and solvent is all common common agents, does not produce waste gas, environmentally safe.
Accompanying drawing explanation
Fig. 1 is the uv-visible absorption spectra figure without replacement cobalt phthalocyanine that embodiment 1 is synthesized.
Embodiment
Embodiment 1 is without the synthetic method replacing cobalt phthalocyanine
By Cobalt diacetate tetrahydrate 1.02g (4.0mmol), phthalic nitrile 2.05g (16.0mmol) joins in the DMF solvent of 30ml successively, in hydrothermal reaction kettle, at 150 DEG C, reaction 4h, stopped reaction is cooled to room temperature, the color of solution is sapphirine, add 300ml ether, namely have a large amount of solid to separate out, suction filtration.Precipitation use methylene dichloride repetitive scrubbing, suction filtration, a large amount of atropurpureus solid, vacuum-drying, obtains pressed powder 1.97g, and productive rate is 86%.
Ultimate analysis (C
32h
16coN
8), measured value (theoretical value) %:C66.82 (67.26), H2.53 (2.82), N19.24 (19.61).
Fig. 1 is without replacing the uv-visible absorption spectra figure of cobalt phthalocyanine in DMF solvent.As can be seen from the figure, 600-800nm is that the Q of phthalocyanine is with charateristic avsorption band, 300-400nm is that the B of phthalocyanine is with charateristic avsorption band, with conforming to without replacing cobalt phthalocyanine uv-visible absorption spectra of reporting in document, in addition by the sign of ultimate analysis, absolutely prove that obtained pure nothing replaces cobalt phthalocyanine.
Embodiment 2 is without the synthetic method replacing cobalt phthalocyanine
By Cobalt diacetate tetrahydrate 1.02g (4.0mmol), phthalic nitrile 2.05g (16.0mmol) joins in the DMF solvent of 30ml successively, in hydrothermal reaction kettle, at 150 DEG C, reaction 4h, stopped reaction is cooled to room temperature, the color of solution is sapphirine, add 300ml acetone, namely have a large amount of solid to separate out, suction filtration.Precipitation use methylene dichloride repetitive scrubbing, suction filtration, a large amount of atropurpureus solid, vacuum-drying, obtains pressed powder 1.74g, and productive rate is 76%.
Embodiment 3 is without the synthetic method replacing cobalt phthalocyanine
By Cobalt diacetate tetrahydrate 1.02g (4.0mmol), phthalic nitrile 2.05g (16.0mmol) joins in the DMF solvent of 30ml successively, in hydrothermal reaction kettle, at 150 DEG C, reaction 4h, stopped reaction is cooled to room temperature, the color of solution is sapphirine, add 300ml ethyl acetate, namely have a large amount of solid to separate out, suction filtration.Precipitation use methylene dichloride repetitive scrubbing, suction filtration, a large amount of atropurpureus solid, vacuum-drying, obtains pressed powder 1.69g, and productive rate is 74%.
Embodiment 4 is without the synthetic method replacing cobalt phthalocyanine
By CoCL2 6H2O 0.952g (4.0mmol), phthalic nitrile 2.05g (16.0mmol) joins in the DMF solvent of 30ml successively, in hydrothermal reaction kettle, at 150 DEG C, reaction 4h, stopped reaction is cooled to room temperature, the color of solution is sapphirine, add 300ml ether, namely have a large amount of solid to separate out, suction filtration.Precipitation use methylene dichloride repetitive scrubbing, suction filtration, a large amount of atropurpureus solid, vacuum-drying, obtains pressed powder 1.81g, and productive rate is 79%.
Embodiment 5 is without the synthetic method replacing cobalt phthalocyanine
By heptahydrate 1.12g (4.0mmol), phthalic nitrile 2.05g (16.0mmol) joins in the DMF solvent of 30ml successively, in hydrothermal reaction kettle, at 150 DEG C, reaction 4h, stopped reaction is cooled to room temperature, the color of solution is sapphirine, add 300ml ether, namely have a large amount of solid to separate out, suction filtration.Precipitation use methylene dichloride repetitive scrubbing, suction filtration, a large amount of atropurpureus solid, vacuum-drying, obtains pressed powder 1.78g, and productive rate is 78%.
Claims (8)
1. without the synthetic method replacing cobalt phthalocyanine, it is characterized in that: with Cobalt salts and phthalic nitrile for raw material, taking DMF as solvent, without the need to adding any catalyzer, being synthesized by hydrothermal synthesis method; Described is as follows without the chemical structural formula replacing cobalt phthalocyanine:
2. the synthetic method without replacing cobalt phthalocyanine according to claim 1, is characterized in that: Cobalt salts and phthalic nitrile are added successively in DMF, and in 130-170 DEG C, reaction 2-6h, is cooled to room temperature, adds organic solvent, suction filtration.
3. the synthetic method without replacing cobalt phthalocyanine according to claim 1 and 2, is characterized in that: in molar ratio, Cobalt salts: phthalic nitrile=1:3-5.
4. the synthetic method without replacing cobalt phthalocyanine according to claim 3, is characterized in that: in molar ratio, Cobalt salts: phthalic nitrile=1:4.
5. the synthetic method without replacing cobalt phthalocyanine according to claim 1 and 2, is characterized in that: described Cobalt salts is Cobalt diacetate tetrahydrate, CoCL2 6H2O or heptahydrate.
6. the synthetic method without replacing cobalt phthalocyanine according to claim 2, is characterized in that: described organic solvent is ether, acetone or ethyl acetate.
7. the synthetic method without replacing cobalt phthalocyanine according to claim 6, is characterized in that: described organic solvent is ether.
8. the synthetic method without replacing cobalt phthalocyanine according to claim 2, is characterized in that: after suction filtration, and purify, described purification is: after suction filtration, gets precipitation, and precipitation uses methylene dichloride repetitive scrubbing.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510526852.9A CN105131002A (en) | 2015-08-25 | 2015-08-25 | Synthetic method of unsubstituted cobalt phthalocyanine |
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| CN201510526852.9A CN105131002A (en) | 2015-08-25 | 2015-08-25 | Synthetic method of unsubstituted cobalt phthalocyanine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496238A (en) * | 2016-10-19 | 2017-03-15 | 东北大学 | A kind of method that solvent-thermal method prepares metal phthalocyanine compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009139973A1 (en) * | 2008-04-01 | 2009-11-19 | New Jersey Institute Of Technology | Microwave-assisted synthesis of perfluorophthalocyanine molecules |
| WO2012105483A1 (en) * | 2011-01-31 | 2012-08-09 | 国立大学法人宇都宮大学 | Method for producing metal complex of compound that has porphyrin skeleton |
| CN102887541A (en) * | 2011-07-21 | 2013-01-23 | 北京化工大学 | Preparation method of phthalocyanine sensitized TiO2 nano-particle by microwave-hydrothermal method |
-
2015
- 2015-08-25 CN CN201510526852.9A patent/CN105131002A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009139973A1 (en) * | 2008-04-01 | 2009-11-19 | New Jersey Institute Of Technology | Microwave-assisted synthesis of perfluorophthalocyanine molecules |
| WO2012105483A1 (en) * | 2011-01-31 | 2012-08-09 | 国立大学法人宇都宮大学 | Method for producing metal complex of compound that has porphyrin skeleton |
| CN102887541A (en) * | 2011-07-21 | 2013-01-23 | 北京化工大学 | Preparation method of phthalocyanine sensitized TiO2 nano-particle by microwave-hydrothermal method |
Non-Patent Citations (1)
| Title |
|---|
| KARIFABAYO，等: "E´tude des interactions intramole´culairesdans les bime´tallophtalocyanines par e´lectrochimie et par spectroe´lectrochimie", 《COMPTESRENDUSCHIMIE》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496238A (en) * | 2016-10-19 | 2017-03-15 | 东北大学 | A kind of method that solvent-thermal method prepares metal phthalocyanine compound |
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Application publication date: 20151209 |
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