CN109444123A - Application and detection method in beta-cyclodextrin-micro benzaldehyde of phenolphthalein probe in detecting - Google Patents
Application and detection method in beta-cyclodextrin-micro benzaldehyde of phenolphthalein probe in detecting Download PDFInfo
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Abstract
The present invention provides a kind of method using micro benzaldehyde in beta-cyclodextrin-phenolphthalein supermolecular probe detection water, inclusion reaction occurs in alkaline environment the invention firstly uses beta-cyclodextrin and phenolphthalein and prepares supermolecular probe, the aqueous solution containing benzaldehyde is added in beta-cyclodextrin-phenolphthalein supermolecular probe again, pass through benzaldehyde, phenolphthalein and beta-cyclodextrin are at war with inclusion reaction, phenolphthalein in supermolecular probe is cemented out, to detect the content of benzaldehyde, method provided by the invention is easy to operate, high sensitivity, it is at low cost, benzaldehyde that can be micro in Rapid Detection water, as a result reliable.
Description
Technical field
The invention belongs to field of chemical detection, and in particular to beta-cyclodextrin-phenolphthalein supermolecular probe is in detection micro-benzene first
Application and specific detection method in aldehyde.
Background technique
Benzaldehyde popular name almond oil is a kind of common organic pollutants in water body in natural environment.The source of benzaldehyde
Mostly come from the discharge of industrial wastewater.There are many benzaldehyde most industrial use, are a kind of important industrial chemicals, for making
Lauric aldehyde, dodecanoic acid, phenylacetaldehyde and some particular perfumes such as wine essence etc., while being also resin, oils, certain nitric acid fibre
The solvent of dimension element, cellulose ether also acts as measurement ozone, phenols, alkaloid etc..The purposes of benzaldehyde is in manufacturing industry at present
There is new infiltration and development again, currently used for paint defoaming agent, anti-friction lubricant etc..Benzaldehyde common are machine dirt as one kind
Object is contaminated in environment water.For aquatile, its harmfulness is great.It belongs to noxious material difficult to degrade, and
And once enter in organism and will cause bioconcentration, there is bioaccumulation.For human body, if into human body
The fuselage state of human body can be upset, illness is made one.Therefore, in Accurate Determining environment water the content of benzaldehyde for environmental protection
Tool has very important significance.
Currently, the analysis and detection method about benzaldehyde are concentrated mainly on gas chromatography, spectrophotometry, liquid phase color
The fields such as spectrometry.If the method for capillary gas chromatography Benzene in Beverages content of formaldehyde, determined by ultraviolet spectrophotometry are without flower
The method etc. of benzaldehyde in the method for benzaldehyde content in fruit, food by HPLC common used material.It is general next
It says, the organic pollutant detected in water needs quickly to detect, in order to timely make counte-rplan.And gas phase color
These methods such as spectrometry, liquid chromatography have the body of operator since sample pre-treatments need a large amount of organic solvent
Certain harm also pollutes the environment simultaneously.And the time of detection is long, takes time and effort, and reproducibility is poor etc., therefore cannot
Satisfaction quickly detects this.
Summary of the invention
For the technical problem more than solving, the present invention provides a kind of method of micro benzaldehyde in detection water, the side
Method forms supermolecular probe using beta-cyclodextrin and phenolphthalein, detects the benzaldehyde in water, and detection speed is fast, and accuracy rate is high.
The object of the present invention is to provide a kind of applications of beta-cyclodextrin-phenolphthalein supermolecular probe.
It is a further object of the present invention to provide a kind of methods using the micro benzaldehyde of above-mentioned probe in detecting.
Beta-cyclodextrin-phenolphthalein supermolecular probe is applied to detect micro benzaldehyde by purpose according to the present invention, the present invention.
Main method in view of the detection at present to the micro benzaldehyde in water is gas chromatography, liquid chromatography etc.,
These detection methods are cumbersome, and ingredient is high.Since the outer wall of β-CD is hydrophilic and inner cavity is hydrophobic, it is thus possible to provide one it is hydrophobic
Environment, as the various guest molecules of main body envelope；Its inner cavity is hydrophobic and the characteristic of external hydrophilic makes it can be according to intermolecular phase
Interaction and many organic molecules and inorganic ions form inclusion compound and molecular assembled system, become many field related scientific research
The research object of worker.The characteristics of present invention can form inclusion compound using beta-cyclodextrin (β-CD) and phenolphthalein (PP), production
Supermolecular probe is measured using supermolecular probe and hears formaldehyde, reduces cost, streamline operation.
The method provided by the invention for detecting micro benzaldehyde using beta-cyclodextrin-phenolphthalein supermolecular probe, including it is following
Step:
(1) beta-cyclodextrin-phenolphthalein supermolecule is prepared using beta-cyclodextrin aqueous solution, phenolphthalein solution and alkaline solution reaction to visit
Needle；
(2) alkaline solution for taking the equivalent in step (1) detects absorbance of the alkaline solution at 552nm；
(3) sample to be tested is reacted with supermolecular probe obtained in step (1), obtains mixed solution, then detection is mixed
Close absorbance of the solution at 552nm；
The concentration of the benzaldehyde in measuring samples is calculated according to △ A=261.21c+0.0523,
Wherein △ A is that the absorbance of mixed solution and alkaline solution at 552nm is poor, and c is the concentration of benzaldehyde.
The present invention makes probe first, the inclusion compound of 1:1 is capable of forming under alkaline condition using β-CD and PP, according to benzene
The inclusion compound of formaldehyde and β-CD are also to be included according to the mass ratio of the material 1:1, are then occurred using benzaldehyde, PP and β-CD competing
Inclusion reaction is striven, the PP molecule of part is cemented out from the cavity of β-CD, causes the PP molecular number of free state in solution
It measures and increases, be exactly that absorbance increases from macroscopically performance, since absorption photometric value of the PP at 552nm is maximum, utilize
The variation of absorbance at 552nm detects the content of the benzaldehyde in water.Method provided by the invention is easy to operate, cost
It is low, high sensitivity.
Preferably, in step (1), the beta-cyclodextrin-phenolphthalein supermolecular probe preparation method is the following steps are included: take
Beta-cyclodextrin aqueous solution and phenolphthalein solution, the solvent of the phenolphthalein solution are the alcohol that volume divides water to be 95%, and it is molten that alkalinity is added
Liquid is uniformly mixed, and is stood reaction 1-5min at room temperature, is obtained the supermolecular probe.Stable probe in order to obtain, by β-
CD is reacted under alkaline condition with PP, since the inclusion reaction of β-CD and PP can be completed in a relatively short time,
Reaction time provided by the invention is 1-5min, guarantees sufficiently reaction；Since PP and benzaldehyde are reacted with the competitive inclusion of β-CD
An exothermic process, high temperature is unfavorable for the progress of inclusion reaction, therefore is reacted at room temperature, guarantee reaction sufficiently into
Row.
Preferably, the molar ratio of the beta-cyclodextrin and phenolphthalein is 6:0.5.
Preferably, the concentration of the beta-cyclodextrin aqueous solution is 2.5 × 10-4-3.5×10-4Mol/L, the phenolphthalein solution
Concentration be 2.0 × 10-5-2.5×10-5mol/L。
Preferably, the concentration of the beta-cyclodextrin aqueous solution is 3.0 × 10-4The concentration of mol/L, the phenolphthalein solution is
2.5×10-5mol/L。
For the stabilization of guarantee system, guarantee that reaction sufficiently carries out, the research of the invention finds that, when β-CD and PP is with above-mentioned dense
After degree and ratio are reacted, the absorbance value of system is stablized, and obtained probe is relatively stable.
Preferably, the alkaline solution is the mixed aqueous solution comprising sodium carbonate and sodium bicarbonate, the alkaline solution
PH is 10.2.It is reacted since β-CD is able to carry out under alkaline condition with PP, the competitive inclusion reaction after benzaldehyde is added
Condition is also required to carry out under alkaline condition, by inventor's the study found that the pH for working as alkaline solution is 10.2, obtained spy
Needle body system absorbance is stablized.
Preferably, the mass ratio of the material of the sodium carbonate and the sodium bicarbonate is 2:5.
Preferably, the content detection range of benzaldehyde is 1.00 × 10-4mol/L-1.00×10-3mol/L。
Preferably, the detection of the benzaldehyde is limited to 9.54 × 10-6Mol/L or more.
Detection limit is according to CL=3 × SIt is empty/ K, wherein K is the slope of △ A=261.21c+0.0523, i.e. K is 261.21, SIt is empty
The absorbance standard deviation for being alkaline solution at 552nm is 8.31 × 10 according to being repeatedly calculated-4。
The invention has the benefit that
The present invention provides a kind of method using micro benzaldehyde in beta-cyclodextrin-phenolphthalein supermolecular probe detection water, this
Invention occurs inclusion reaction in alkaline environment first with beta-cyclodextrin and phenolphthalein and prepares supermolecular probe, then molten with alkalinity
Liquid is that blank group detects absorbance of the blank group at 552nm, then the aqueous solution containing benzaldehyde is added to beta-cyclodextrin-phenol
In phthalein supermolecular probe, it is at war with inclusion reaction by benzaldehyde, phenolphthalein and beta-cyclodextrin, by the phenolphthalein in supermolecular probe
It cements out, absorbance of the mixed solution obtained after detection reaction at 552nm utilizes absorbance difference detection benzaldehyde
Content, method provided by the invention is easy to operate, high sensitivity, at low cost, benzaldehyde that can be micro in Rapid Detection water, knot
Fruit is reliable.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
It obtains other drawings based on these drawings.
Fig. 1 is influence of the temperature to reaction；
Fig. 2 is influence of the alkaline solution dosage to inclusion reaction；
Fig. 3 is influence of the PP concentration to inclusion reaction；
Fig. 4 is influence of the dosage to inclusion reaction of β-CD；
Fig. 5 is the working curve of benzaldehyde.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, technical solution of the present invention will be carried out below
Detailed description.Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Base
Embodiment in the present invention, those of ordinary skill in the art are obtained all without making creative work
Other embodiment belongs to the range that the present invention is protected.
Embodiment 1
The method for detecting micro benzaldehyde using beta-cyclodextrin-phenolphthalein supermolecular probe, comprising the following steps:
(1) beta-cyclodextrin-phenolphthalein supermolecule is prepared using beta-cyclodextrin aqueous solution, phenolphthalein solution and alkaline solution reaction to visit
Needle；
(2) alkaline solution for taking the equivalent in step (1) detects absorbance of the alkaline solution at 552nm；
(3) sample to be tested is reacted with supermolecular probe obtained in step (1), obtains mixed solution, then detection is mixed
Close absorbance of the solution at 552nm；
The concentration of the benzaldehyde in measuring samples is calculated according to △ A=261.21c+0.0523,
Wherein △ A is that the absorbance of mixed solution and alkaline solution at 552nm is poor, and c is the concentration of benzaldehyde.
Embodiment 2
The method for preparing the supermolecular probe in embodiment 1 in step (1):
A. it prepares beta-cyclodextrin aqueous solution: first recrystallizing beta-cyclodextrin, take the β-CD of 5g in beaker, add water
100mL is heated to boiling, and obtains clear solution, and standing is cooled to room temperature, and obtains β-CD sample in 120 DEG C of drying after filtering,
Secondary recrystallization is carried out with same operation again, sample is spare.β-CD (secondary recrystallization) sample 1.1356g is weighed in beaker,
After addition distilled water is to be dissolved, it is transferred in the volumetric flask of 100mL, constant volume to 100mL obtains 1.00 × 10-2Mol/L β-CD water
Solution；
B. it prepares phenolphthalein solution: weighing 0.1591gPP sample in small beaker, after 95% ethyl alcohol dissolution is added, transfer
Into the volumetric flask of 50mL, with 95% ethyl alcohol constant volume to 50mL, 1.00 × 10 are obtained-2Mol/LPP solution；
C. Na is prepared2CO3-NaHCO3Solution takes NaHCO3And Na2CO3Sample is put into baking oven, in 120 DEG C of dry 3h, so
After weigh 0.1050gNaHCO3Sample is dissolved to 50mL, weighs 0.0530gNa2CO3Sample is mixed after being dissolved to 50mL, is obtained
The alkaline solution for being 10.2 to pH value.
Detection method:
Several 10mL colorimetric cylinders are taken first, then sequentially add 1.00 × 10 thereto-3β-the CD3.00mL of mol/L,
1.00×10-4The Na of the PP2.50mL of mol/L, pH=10.202CO3-NaHCO3It mixes and shakes up after buffer solution 3.00mL.Most
After a certain amount of benzaldehyde is added, be diluted to 10.00mL, sufficiently vibrate, stand 1-5min.In TU-1810SPC ultraviolet-visible
The absorbance A of solution is measured on spectrophotometer, at λ max with the Na of equivalent2CO3-NaHCO3Buffer solution and distilled water are
Reagent blank A0 calculates the difference DELTA A (Δ A=A-A0) of absorbance.
Embodiment 3
Reaction system is prepared according to the method for embodiment 2, investigates the variation of system absorbance at different temperatures.As a result see
Fig. 1.
As shown in Figure 1, as the raising of solution temperature, the absorbance value of reaction system are being gradually reduced, show the inclusion
Reaction is exothermic process, and within the temperature range of study, when high temperature is unfavorable for inclusion reaction progress, and temperature reduces favorably
In the progress of inclusion reaction.This may increase due to the raising of temperature, the kinetic energy of benzaldehyde molecule, random motion aggravation, from
And benzaldehyde molecule and the intermolecular interaction of β-CD is caused to weaken, including hydrophobic interaction, Van der Waals force, hydrogen bond work
Firmly etc..Meanwhile temperature increases, it is also possible to cause the cavity of β-CD to increase, cause benzaldehyde molecule good with β-CD
It combines closely.So the temperature setting of experiment carries out at room temperature.
Embodiment 4
The influence of alkaline solution dosage
Reaction system is prepared according to the method for embodiment 2, investigates Na at room temperature2CO3-NaHCO3Buffer solution medium is used
Measure the influence to system absorbance.As a result see Fig. 2.
As shown in Figure 2, absorbance is with Na2CO3-NaHCO3The increase of volume of buffer solution is 3.00mL when volume is added
When, the absorbance of solution is no longer changed substantially reaches maximum.Na is selected as a result,2CO3-NaHCO3The dosage of buffer solution is
3.00mL。
Embodiment 5
The influence of PP concentration
Reaction system is prepared according to the method for embodiment 2, at room temperature, fixed Na2CO3-NaHCO3Buffer solution 3.00mL,
1.00×10-3β-the CD3.00mL of mol/L, time of repose 1-5min.Change PP concentration, investigate at room temperature PP concentration to body
It is the influence of absorbance.As a result see Fig. 3.
From the figure 3, it may be seen that the concentration of PP is 2.0 × 10-5-2.5×10-5Mol/L, Δ A value reach maximum, are basically unchanged.By
The concentration of PP is 2.50 × 10 in solution-5When mol/L, Δ A value reaches maximum, and with the increase of PP dosage, the variation of Δ A value becomes
In steady.Therefore, select concentration for 1.00 × 10 in current experiment-4The PP of mol/L, pipetting volume is 2.50mL, molten at this time
The concentration of PP is 2.50 × 10 in liquid-5mol/L。
Embodiment 6
The influence of the dosage of β-CD
Reaction system, the concentration of fixed PP and the concentration of benzaldehyde are prepared according to the method for embodiment 2, investigates the use of β-CD
Measure the influence to system absorbance.As a result see Fig. 4.
As shown in Figure 4, the dosage of β-CD Δ A when 2.00mL reaches maximum, but not stable enough, and analysis reason can
Know, at the beginning, the amount of β-CD is less than the amount of PP and benzaldehyde in solution, is merely able to inclusion part PP molecule.Until continuing to increase
When the dosage of big β-CD, β-CD can include the phenolphthalein in solution completely, and the hydrophobicity of benzaldehyde is strong compared with PP, the knot with β-CD
Conjunction ability is better than the binding ability of β-CD and PP, so β-CD is more likely to inclusion benzaldehyde at this time, and PP then can be by benzaldehyde
Displacement is gone out, and free PP will cause the increase of absorbance in the solution.So the absorbance value of solution progressivelyes reach at this time
It is maximum.Thus selection tends to be steady the β-CD dosage in stage, at this point, system is most stable.At this time β-CD to do be 2.5 ×
10-4-3.5×10-4Mol/L, therefore the additional amount for choosing β-CD is 3.00mL, the concentration in solution is 3.00 × 10 at this time- 4mol/L。
Embodiment 7
According to the optimum condition that embodiment 3-6 is obtained, the concentration for fixing PP at room temperature is 1.00 × 10-4Mol/L is pipetted
Volume is 2.50mL, and the concentration of β-CD is 1.00 × 10-3Mol/L, pipetting volume is 3.00mL, and Na2CO3-NaHCO3 buffering is molten
The volume that pipettes of liquid is 3.00mL, stands 1-5min.The concentration for changing benzaldehyde at wavelength 552nm, then measures absorbance
Δ A, using concentration c as abscissa, absorbance difference Δ A is ordinate mapping, as a result such as Fig. 5:
Benzaldehyde is 1.00 × 10 as shown in Figure 5-4mol/L-1.00×10-3There is good linear pass in the section of mol/L
System, equation of linear regression:
Δ A=261.21c+0.0523R2=0.9958
Relation character i.e. between the concentration c (mol/L) and absorbance difference Δ A of benzaldehyde closes the formula stated, therefore only
Try to obtain the absorbance difference Δ A of benzaldehyde solution of the wavelength at 552nm, corresponding benzaldehyde in system can be acquired
Concentration.
Embodiment 8
Detection limit
To 7.50 × 10-4The benzaldehyde solution system of mol/L carries out 11 measurements under conditions of embodiment 7, opposite
Standard deviation is 1.1%, and by 11 blank assays, the standard deviation S sky of A0 is 8.31 × 10-4.It can by the formula of embodiment 3
Know slope K=261.21 of standard curve, detection is limited to CL=3 × SIt is empty/ K=3 × 8.31 × 10-4/ 261.21=9.54 × 10-6mol/L。
Embodiment 9
Not only contain a kind of this pollutant of benzaldehyde in the natural water environment of reality, therefore, it is also desirable to consider other
The interference effect of organic pollutant.At optimum conditions, the organic matters such as phenol and para aminotenzaldehyde are added, the suction of solution is measured
Luminosity.These interference organic matters are analyzed in the presence of β-CD-PP spectral probe, are acted on by competitive inclusion, to detect benzaldehyde
Content.
- CD1.00 × 10 host molecule β under optimum condition are separately added into the color-comparison tube of 7 10mL-3mol/
L3.00mL, PP1.00 × 10-4The Na of mol/L2.50mL, pH=10.202CO3-NaHCO3Buffer solution and benzaldehyde 1.00 ×
10-3Mol/L1.00mL, and phenol and para aminotenzaldehyde with benzaldehyde comparable sodium and volume is added, with Na2CO3-
NaHCO3Buffer solution and distilled water are reagent blank.It is diluted to graduation mark, is shaken up, after standing 1min, is inhaled with photometric determination
Luminosity, to determine the maximum concentration of interfering component of the relative error no more than ± 5% as the maximum concentration of Coexisting component.As a result table
It is bright to do spectral probe measurement 1.00 × 10 with β-CD-PP-3The maximum magnitude of each chaff interferent is respectively as follows: 5 when the benzaldehyde of mol/L
Phenol organic matter again, 10 times of para aminotenzaldehyde.
Embodiment 10
Water sample is acquired in Jin Bohu, Xing Qinghu and Xixia Garden lake surface respectively with sampling bottle, number is water sample 1, water respectively
Sample 2 and water sample 3.It is adjusted to pH=1-2 with acid, and is placed at 4 DEG C of refrigerator and saves.Accurately 1.00mL is pipetted in 10mL colorimetric cylinder,
PH=10.20 or so is adjusted to the NaOH solution of 0.1mol/L.Measure the content of benzaldehyde in water sample simultaneously as described in Example 2
Do recovery experiment.It the results are shown in Table 1.
The measurement result (n=6) of benzaldehyde in 1 water sample of table
As shown in Table 1, the RSD measured is tested less than 5%, and the rate of recovery illustrates this experiment between 93.6%-100.6%
The accuracy of method and precision are relatively high, and easy to operate, and finding speed is fast, as a result accurately.
Embodiment 11
To the method for detecting benzaldehyde than in the prior art, beta-cyclodextrin-phenolphthalein supermolecule is utilized with provided by the invention
The method of probe assay benzaldehyde, the results are shown in Table 2.
The Comparative result of the different detection benzaldehyde Methods of table 2
From the results shown in Table 2, method detection limit provided by the invention is higher than other both of which.The present invention mentions
The method victory of confession is that operation is easy and efficient is quick, result is reliable, the ability with on-site test.Benzaldehyde is fast in suitable water
Fast real-time detection, the content for detecting micro benzaldehyde in water can obtain more satisfied result.So this method has
Certain application potential.
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Those familiar with the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, and should all contain
Lid is within protection scope of the present invention.Therefore, protection scope of the present invention should be based on the protection scope of the described claims.
Claims (10)
1. a kind of beta-cyclodextrin-phenolphthalein supermolecular probe is detecting the application in micro benzaldehyde.
2. the method for detecting micro benzaldehyde using supermolecular probe described in claim 1, which is characterized in that including following step
It is rapid:
(1) beta-cyclodextrin-phenolphthalein supermolecular probe is prepared using beta-cyclodextrin aqueous solution, phenolphthalein solution and alkaline solution reaction；
(2) alkaline solution for taking the equivalent in step (1) detects absorbance of the alkaline solution at 552nm；
(3) sample to be tested is reacted with supermolecular probe obtained in step (1), obtains mixed solution, then detection mixing is molten
Absorbance of the liquid at 552nm；
The concentration of the benzaldehyde in measuring samples is calculated according to △ A=261.21c+0.0523,
Wherein △ A is that the absorbance of mixed solution and alkaline solution at 552nm is poor, and c is the concentration of benzaldehyde.
3. the method for the micro benzaldehyde of detection according to claim 2, which is characterized in that in step (1), the β-ring paste
For essence-phenolphthalein supermolecular probe preparation method the following steps are included: taking beta-cyclodextrin aqueous solution and phenolphthalein solution, the phenolphthalein is molten
The solvent of liquid is the alcohol that volume divides water to be 95%, and alkaline solution is added, and is uniformly mixed, and stands reaction 1-5min at room temperature,
Obtain the supermolecular probe.
4. the method for the micro benzaldehyde of detection according to claim 3, which is characterized in that the beta-cyclodextrin and phenolphthalein
Molar ratio is 6:0.5.
5. the method for the micro benzaldehyde of detection according to claim 4, which is characterized in that the beta-cyclodextrin aqueous solution
Concentration is 2.5 × 10-4-3.5×10-4Mol/L, the concentration of the phenolphthalein solution are 2.0 × 10-5-2.5×10-5mol/L。
6. the method for the micro benzaldehyde of detection according to claim 5, which is characterized in that the beta-cyclodextrin aqueous solution
Concentration is 3.0 × 10-4Mol/L, the concentration of the phenolphthalein solution are 2.5 × 10-5mol/L。
7. the method for the micro benzaldehyde of detection according to claim 6, which is characterized in that the alkaline solution is to include carbon
The mixed aqueous solution of sour sodium and sodium bicarbonate, the pH of the alkaline solution are 10.2.
8. the method for the micro benzaldehyde of detection according to claim 7, which is characterized in that the sodium carbonate and the carbonic acid
The mass ratio of the material of hydrogen sodium is 2:5.
9. according to the method for any micro benzaldehyde of detection of claim 2-8, which is characterized in that the content of benzaldehyde is examined
Surveying range is 1.00 × 10-4mol/L-1.00×10-3mol/L。
10. according to the method for any micro benzaldehyde of detection of claim 2-8, which is characterized in that the benzaldehyde
Detection is limited to 9.54 × 10-6Mol/L or more.
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