CN107673991A - A kind of Schiff base derivatives and preparation method thereof - Google Patents
A kind of Schiff base derivatives and preparation method thereof Download PDFInfo
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- CN107673991A CN107673991A CN201711105235.7A CN201711105235A CN107673991A CN 107673991 A CN107673991 A CN 107673991A CN 201711105235 A CN201711105235 A CN 201711105235A CN 107673991 A CN107673991 A CN 107673991A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
The invention discloses a kind of Schiff base derivatives and preparation method thereof, the structural formula of the Schiff base derivatives is：
Description
Technical field
The invention belongs to organic synthesis field, more particularly to a kind of Schiff base derivatives and preparation method thereof.
Background technology
Schiff bases is primarily referred to as a kind of organic compound containing imines or azomethine group, typically by containing active carbonyl
Compound and the primary amine condensation of base form.Schiff bases and its complex, have excellent antibacterial, anticancer, antiviral, weeding etc. raw
Thing activity, and the performance such as special photoelectromagnetic.Therefore, draw in recent years in fields such as medicine, biology, catalysis and functional materials
The widely studied interest of researcher is played.
However, the traditional preparation methods of schiff bases be usually in organic solvent, by the compound containing active carbonyl with
Amine carries out condensation reaction and obtained, and reaction needs to use organic solvent, catalyst, and the reaction time is longer, and side reaction is more, and is difficult to
Separating-purifying, there is the deficiencies of power consumption is high, pollution is larger.Therefore, new Schiff base derivatives are developed, and green,
The low preparation method of high-efficient simple, energy consumption is significant.
Publication No. CN106748879A patent of invention disclose a kind of paranitrobenzaldehyde Schiff base derivatives and its
Preparation method, this method is using o-aminophenol and paranitrobenzaldehyde as raw material, by above-mentioned reaction raw materials in hydrothermal reaction kettle
Mix with appropriate water, reacted under high temperature by the high diffusivity coefficient and strong solubility of high-temperature water.The patented method is not
Using organic solvent and catalyst, mild condition, but the Schiff base derivatives low yield prepared, it is typically left 20~30%
It is right.
The content of the invention
For deficiencies of the prior art, it is an object of the invention to provide a kind of Schiff base derivatives and its preparation
Method, solve the problems, such as that existing method prepares Schiff base derivatives and needs to use organic solvent, catalyst.
To achieve the above object, the present invention adopts the following technical scheme that：
Schiff base derivatives of the present invention, shown in its structural formula such as formula (I)：
The preparation method of Schiff base derivatives is as described above：It is 1 by mol ratio:1~2 o-aminophenol and to first
Benzaldehyde, which is placed in hydrothermal reaction kettle, to be reacted, wherein, the compactedness of the hydrothermal reaction kettle reclaimed water is 30~70%, instead
It is 90~170 DEG C to answer temperature, and the reaction time is 180~360min, and reaction finishes, and reaction product is filtered, dry, recrystallization,
Obtain described Schiff base derivatives.
The reaction equation that the present invention prepares Schiff base derivatives is as follows：
Preferably, the mol ratio of the o-aminophenol and p-tolyl aldehyde is 1:1.5~2.
Preferably, the reaction temperature is 140~160 DEG C.
Preferably, the reaction time is 240~360min.
Preferably, the compactedness is 50~70%.
Under above-mentioned optimum condition, the yield of Schiff base derivatives prepared by the present invention is greatly improved.
Preferably, ethanol or ethyl acetate that the solvent that recrystallization uses is 95%.The present invention by preferable solvent,
The purity and yield of product can be effectively improved, recrystallization method is conventional method.
Schiff base derivatives prepared by the present invention can be applied in the fields such as medicine, catalysis and functional material.
Compared with prior art, the present invention has the advantages that：
1st, the preparation method of Schiff base derivatives of the present invention replaces Conventional glass instrument to be filled as reaction using hydrothermal reaction kettle
Put, high temperature high voltage resistant, conventional organic solvent is replaced as reaction medium using water, it is nontoxic, and without using any catalyst,
Reaction raw materials are mixed with suitable quantity of water in hydrothermal reaction kettle, are placed under the subcritical or supercritical temperature of water, mainly utilize high temperature
The high diffusivity coefficient and strong solubility of water, so that reaction is efficient, easily carries out.The preparation method is green, condition temperature
With the reaction time is short, and accessory substance is few and is easily isolated purification, and yield is high, is easy to operate and control, required equipment and raw material are easy
, it is cheap.
2nd, the Schiff base derivatives that prepare of the present invention, due to the connection of imines both ends it is on the one hand the structure containing phenyl ring,
Chemical stability is good, on the other hand, is dissolved in common a variety of organic solvents, dissolubility is good, and has photoluminescent property, in organic hair
The fields such as optical function material have a good application prospect.
3rd, the present invention reduces the generation of side reaction, significantly by the selection and the optimization of reaction condition to reaction raw materials
The yield of the Schiff base derivatives of preparation is improved, maximum output is up to 68.8%, hence it is evident that prepare higher than existing congenic method
The yield of Schiff base derivatives.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of Schiff base derivatives prepared by embodiment 1；
Fig. 2 is the fluorescence emission spectrogram of compound of Schiff base derivatives prepared by embodiment 1.
Embodiment
The present invention is described in further detail with reference to specific embodiment.
Embodiment 1
In 25mL hydrothermal reaction kettle, 15mL water (compactedness 60%) is added, adds 1mmol adjacent aminobenzene
The p-tolyl aldehyde of phenol and 1mmol, reacted 180 minutes at 150 DEG C.After reaction terminates, after reactor is cooled into room temperature,
Reaction product is filtered successively, dries, recrystallize, is dried, that is, obtains target product, is used when being recrystallized in the present embodiment
Solvent be ethyl acetate.
Embodiment 2
In 50mL hydrothermal reaction kettle, 25mL water (compactedness 50%) is added, adds 2mmol adjacent aminobenzene
The p-tolyl aldehyde of phenol and 2mmol, reacted 240 minutes at 120 DEG C.After reaction terminates, after reactor is cooled into room temperature,
Reaction product is filtered successively, dries, recrystallize, is dried, that is, obtains target product, is used when being recrystallized in the present embodiment
Solvent be 95% ethanol.
Embodiment 3
In 50mL hydrothermal reaction kettle, 20mL water (compactedness 40%) is added, adds 1mmol adjacent aminobenzene
The p-tolyl aldehyde of phenol and 1.5mmol, reacted 300 minutes at 100 DEG C.After reaction terminates, reactor is cooled to room temperature
Afterwards, reaction product filtered successively, dried, being recrystallized, being dried, that is, target product being obtained, when being recrystallized in the present embodiment
The solvent used is ethyl acetate.
Embodiment 4~13
The operating method of embodiment 4~13 is same as Example 1, and difference is design parameter difference, is specifically shown in Table 1.
The relevant parameter of 1 embodiment of table 1~13
By above example, Schiff base derivatives yield prepared by the present invention reaches as high as 68.8%.
Fig. 1 is the infrared spectrogram of Schiff base derivatives prepared by embodiment 1, and as seen from the figure, raw material o-aminophenol exists
3300cm-1And 3375cm-1Place, be attributed to primary amine N-H telescope features absworption peaks it is reacted after disappear, Schiff base derivatives
In about 1635cm-1There is the telescope features absworption peak of schiff bases-C=N- groups, in about 860cm-1And 760cm-1Occur respectively
Contraposition and the phenyl ring characteristic absorption peak of ortho position substitution, thus illustrate that target product schiff bases is successfully prepared.
Fig. 2 is the Schiff base derivatives that prepare of embodiment 1 in absolute ethyl alcohol (solid line in figure) and tetrahydrofuran (void in figure
Line) in fluorescence emission spectrogram of compound (excitation wavelength 300nm), as shown in Figure 2, the Schiff base derivatives that prepare of the present invention are in nothing
There is certain luminosity in water-ethanol and tetrahydrofuran solution, there is potential application in the fields such as luminous organic material
Value.
The above embodiment of the present invention is only example to illustrate the invention, and is not the implementation to the present invention
The restriction of mode.For those of ordinary skill in the field, other can also be made not on the basis of the above description
With the change and variation of form.Here all embodiments can not be exhaustive.It is every to belong to technical scheme
Row of the obvious changes or variations amplified out still in protection scope of the present invention.
Claims (7)
- A kind of 1. Schiff base derivatives as shown in formula (I)：
- A kind of 2. method for preparing Schiff base derivatives as claimed in claim 1, it is characterised in that by mol ratio be 1:1~2 O-aminophenol and p-tolyl aldehyde be placed in hydrothermal reaction kettle and reacted, wherein, the hydrothermal reaction kettle reclaimed water Compactedness is 30~70%, and reaction temperature is 90~170 DEG C, and the reaction time is 180~360min, after completion of the reaction, reaction production Thing is filtered, dry, recrystallization, that is, obtains described Schiff base derivatives.
- 3. the preparation method of Schiff base derivatives according to claim 2, it is characterised in that the o-aminophenol and right The mol ratio of tolyl aldehyde is 1:1.5~2.
- 4. the preparation method of Schiff base derivatives according to claim 2, it is characterised in that the reaction temperature is 140 ~160 DEG C.
- 5. the preparation method of Schiff base derivatives according to claim 2, it is characterised in that the reaction time is 240 ~360min.
- 6. the preparation method of Schiff base derivatives according to claim 2, it is characterised in that the compactedness be 50~ 70%.
- 7. the preparation method of Schiff base derivatives according to claim 2, it is characterised in that recrystallizing the solvent used is 95% ethanol or ethyl acetate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113502014A (en) * | 2021-09-13 | 2021-10-15 | 中国科学院宁波材料技术与工程研究所 | Antibacterial agent and preparation method and application thereof |
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| CN106496065A (en) * | 2016-10-31 | 2017-03-15 | 重庆理工大学 | A kind of o-phenylenediamine Schiff base derivatives and preparation method and application |
| CN106518726A (en) * | 2016-10-31 | 2017-03-22 | 重庆理工大学 | Aryl Schiff base derivative and preparation method and application thereof |
| CN106748879A (en) * | 2016-10-31 | 2017-05-31 | 重庆理工大学 | P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof |
-
2017
- 2017-11-10 CN CN201711105235.7A patent/CN107673991A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106496065A (en) * | 2016-10-31 | 2017-03-15 | 重庆理工大学 | A kind of o-phenylenediamine Schiff base derivatives and preparation method and application |
| CN106518726A (en) * | 2016-10-31 | 2017-03-22 | 重庆理工大学 | Aryl Schiff base derivative and preparation method and application thereof |
| CN106748879A (en) * | 2016-10-31 | 2017-05-31 | 重庆理工大学 | P-nitrobenzaldehyde Schiff base derivative and preparation method and application thereof |
Non-Patent Citations (1)
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| CHO, YEON-HO等: "Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation", 《TETRAHEDRON》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113502014A (en) * | 2021-09-13 | 2021-10-15 | 中国科学院宁波材料技术与工程研究所 | Antibacterial agent and preparation method and application thereof |
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