CN107619380A - A kind of single Schiff base derivatives and preparation method thereof - Google Patents
A kind of single Schiff base derivatives and preparation method thereof Download PDFInfo
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- CN107619380A CN107619380A CN201711105242.7A CN201711105242A CN107619380A CN 107619380 A CN107619380 A CN 107619380A CN 201711105242 A CN201711105242 A CN 201711105242A CN 107619380 A CN107619380 A CN 107619380A
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Abstract
The invention discloses a kind of single Schiff base derivatives and preparation method thereof, the structural formula of single Schiff base derivatives is：
Description
Technical field
The invention belongs to organic synthesis field, more particularly to a kind of single 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. CN106518726A patent of invention discloses a kind of aryl Schiff base derivatives and preparation method thereof,
This method mixes above-mentioned reaction raw materials and appropriate water in hydrothermal reaction kettle using NPD and benzaldehyde as raw material
Close, reacted under high temperature by the high diffusivity coefficient and strong solubility of high-temperature water.The patented method is without using organic solvent
And catalyst, mild condition, but the aryl Schiff base derivatives low yield prepared, typically 20~30% or so.
The content of the invention
For deficiencies of the prior art, it is an object of the invention to provide a kind of single Schiff base derivatives and its system
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：
Single Schiff base derivatives of the present invention, shown in its structural formula such as formula (I)：
The preparation method of single Schiff base derivatives is as described above：It is 1 by mol ratio:1~2 3,4- diaminotoluenes
It is placed in hydrothermal reaction kettle and is reacted with benzaldehyde, wherein, the compactedness of the hydrothermal reaction kettle reclaimed water is 30~70%, instead
It is 90~180 DEG C to answer temperature, and the reaction time is 180~480min, after completion of the reaction, reaction product is filtered, it is dry, tie again
Crystalline substance, that is, obtain described single Schiff base derivatives.
The reaction equation that the present invention prepares single Schiff base derivatives is as follows：
Preferably, the mol ratio of 3, the 4- diaminotoluenes and benzaldehyde is 1:1.5~2.
Preferably, the reaction temperature is 150~170 DEG C.
Preferably, the reaction time is 300~420min.
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 the single Schiff base derivatives of the present invention replaces Conventional glass instrument as reaction using hydrothermal reaction kettle
Device, 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, it is main using high
The high diffusivity coefficient and strong solubility of warm water, so that reaction is efficient, easily carries out.The preparation method is green, condition
Gently, 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 65.6%, 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, 10mL water (compactedness 40%) is added, adds 2mmol 3,4- diaminos
The benzaldehyde of base toluene and 2mmol, reacted 150 minutes at 150 DEG C.It is right after reactor is cooled into room temperature after reaction terminates
Reaction product filtered, dried, being recrystallized successively, is dried, that is, obtains target product, recrystallized in the present embodiment use it is molten
Agent is ethyl acetate.
Embodiment 2
In 50mL hydrothermal reaction kettle, 25mL water (compactedness 50%) is added, adds 5mmol 3,4- diaminos
Base toluene and 5mmol benzaldehydes, reacted 240 minutes at 100 DEG C.After reaction terminates, after reactor is cooled into room temperature, to anti-
Answer product filtered, dried successively, recrystallized, dry, that is, obtain target product, the solvent used is recrystallized in the present embodiment
For 95% ethanol.
Embodiment 3
In 50mL hydrothermal reaction kettle, 30mL water (compactedness 60%) is added, adds 1mmol 3,4- diaminos
Base toluene and 1.5mmol benzaldehydes, reacted 360 minutes at 140 DEG C.It is right after reactor is cooled into room temperature after reaction terminates
Reaction product filtered, dried, being recrystallized successively, is dried, that is, obtains target product, recrystallized in the present embodiment use it is molten
Agent is ethyl acetate.
Embodiment 4~12
The operating method of embodiment 4~12 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 1~12
By above example, Schiff base derivatives yield prepared by the present invention reaches as high as 65.6%.
Fig. 1 is the infrared spectrogram of single Schiff base derivatives prepared by embodiment 1, as seen from the figure, single schiff bases of preparation
Derivative is in about 1625cm-1There is the telescope features absworption peak of schiff bases-C=N- groups, thus illustrate target product Schiff
Alkali is successfully prepared.
Fig. 2 is the single 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, single Schiff base derivatives for preparing of the present invention exist
There is certain luminosity in absolute ethyl alcohol and tetrahydrofuran solution, have in the fields such as luminous organic material and potentially should
With 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. single Schiff base derivatives as shown in formula (I)：
- A kind of 2. method for preparing single Schiff base derivatives as claimed in claim 1, it is characterised in that by mol ratio be 1:1 ~23,4- diaminotoluenes and benzaldehyde, which is placed in hydrothermal reaction kettle, to be reacted, wherein, the hydrothermal reaction kettle reclaimed water Compactedness is 30~70%, and reaction temperature is 90~180 DEG C, and the reaction time is 180~480min, after completion of the reaction, reaction production Thing is filtered, dry, recrystallization, that is, obtains described single Schiff base derivatives.
- 3. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that 3, the 4- diaminourea first The mol ratio of benzene and benzaldehyde is 1:1.5~2.
- 4. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that the reaction temperature is 150~170 DEG C.
- 5. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that the reaction time is 300~420min.
- 6. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that the compactedness be 50~ 70%.
- 7. the preparation method of single Schiff base derivatives according to claim 2, it is characterised in that recrystallize the solvent used For 95% ethanol or ethyl acetate.
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| CN201711105242.7A CN107619380A (en) | 2017-11-10 | 2017-11-10 | A kind of single Schiff base derivatives and preparation method thereof |
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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 |
-
2017
- 2017-11-10 CN CN201711105242.7A patent/CN107619380A/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 |
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Application publication date: 20180123 |