CN107045008B - A kind of aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid discrimination method - Google Patents
A kind of aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid discrimination method Download PDFInfo
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Abstract
A kind of discrimination method of aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid, it is characterised in that: apply " H2SO4‑KIO3‑[NiL](ClO4)2Malonic acid-H2O2" nonlinear chemical oscillation system is as solution is identified, according to aromatic isomer to oscillatory response caused by the system, and then realize that aromatic series identifies the differentiation of isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid；[NiL](ClO4)2Middle L is 5,7,7,12,14,14- vegolysen, tetra- azepine of 4,8,11-, 14-4,11- diene.Oscillation map provided by this identification method has more intuitive, it not only can be convenient and quickly identify aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid, it can also be widely used in other isomers, and equipment is simple, accuracy is high, easily operated and observation.
Description
Technical field
The present invention relates to a kind of differentiation discrimination methods, specifically a kind of 14 cyclic diolefine nickel complex of four azepine
[NiL](ClO4)2 The nonlinear chemical system of catalysis is to aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid
Discrimination method.Belong to qualitative analysis chemical field.
Background technique
2 hydroxybenzoic acid and 3- hydroxybenzoic acid molecular formula having the same, belong to aromatic isomer,
Shown in the following formula (I) of structure.They play very important role in respective field each other.2 hydroxybenzoic acid (water
Poplar acid) it is plant extract of willow bark, it is a kind of natural anti-inflammatory drug.Salicylic acid is usually used in treating various chronic skins in dermatology
Skin disease such as acne (whelk), tinea etc.；3- hydroxybenzoic acid is used as fungicide, coating, preservative, ion-exchanger, plasticizer
And the intermediate of medicine, it is also possible to Lai Hecheng azo dyes etc..
Since 2 hydroxybenzoic acid is identical with 3- hydroxybenzoic acid molecular formula, structure is close, so that some physics and chemistry
Property is also similar, and the appearance of the two is also very much like, and the two is caused to be difficult to differentiate between.Although many reports existing at present are about fixed
The method of amount analysis hydroxybenzoic acid concentration, such as HPLC, electrochemical methods, capillary electrophoresis.But about to 2- hydroxyl
The differentiation identification of two kinds of isomers of yl benzoic acid and 3- hydroxybenzoic acid there is no report.Therefore, there is an urgent need to a kind of identifications
Effect it is good and it is easy to operate quickly, the result method that easily determines identify both substances.
(I)
Summary of the invention
The present invention is directed to for aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid provide it is a kind of novel and
Discrimination method is conveniently distinguished, i.e., with four azepine 14 cyclic diolefine nickel complex [NiL] (ClO4)2The non-linearization of catalysis
For system to the discrimination method of 2 hydroxybenzoic acid and 3- hydroxybenzoic acid, this discrimination method is complex-catalyzed non-based on this
Linear chemical system (i.e. oscillation system) is responded to the acumen of aromatic isomer and a kind of electrochemical oscillation body of exploitation
It is method.Specifically by same concentrations sample solution to be identified, it is added separately in two groups of oscillation systems, according to sample to be identified
Product are different to oscillatory response caused by oscillation system (variation for vibrating map), realize qualitative point to sample to be identified
Analysis.
The present invention solves technical problem, adopts the following technical scheme that
The discrimination method of aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid of the present invention, feature exist
In:
Using secondary distilled water as solvent, the solution of sample to be identified is prepared；
Using " H2SO4 - KIO3 - [NiL](ClO4)2 Malonic acid-H2O2" nonlinear chemical oscillation system conduct mirror
Other solution records the oscillation map of oscillation system, at any one stable current potential minimum point, respectively into two groups of oscillation systems
The solution of sample to be identified is added, according to sample to be identified to the difference of oscillatory response caused by oscillation system, mirror is treated in realization
The qualitative analysis of other style product；
The sample to be identified is 2 hydroxybenzoic acid and 3- hydroxybenzoic acid；
After being separately added into the solution of sample to be identified into two groups of oscillation systems, if sample to be identified makes oscillation system
Amplitude of oscillation slightly reduces and cycle of oscillation is elongated, then the sample to be identified is 2 hydroxybenzoic acid, and if sample to be identified
Oscillation system is not influenced, then the sample to be identified is 3- hydroxybenzoic acid.
The 3rd ~ 20 current potential that any one the stable current potential minimum point for wherein vibrating generation refers to that oscillation generates is minimum
Point in any one.
So-called four azepines, the 14 cyclic diolefine nickel complex of the present invention is 5,7,7,12,14,14- vegolysen,
4,8,11- tetra- azepines 14-4,11- diene are four major esters nickel (II) complex of ligand, are denoted as [NiL] (ClO4)2,
L is 5,7,7,12,14,14- vegolysens, 4,8,11- tetra- azepines 14-4,11- diene, and structure is as shown in the formula (II).
(II)
Myoglobins in the structure and life entity of this complex, hemoglobin, chlorophyll and some metalloenzyme key
Structure porphyrin ring is much like, this with [NiL] (ClO4)2The chemical oscillating reaction and the intracellular biochemistry of plant and animal of catalysis
It vibrates similar.So the system has stable amplitude, longer oscillation service life and to 2 hydroxybenzoic acid and 3- hydroxy benzenes first
The sharp response of acid.
Four major esters catalyst plays a crucial role in the present invention, and configuration is broadly divided into two steps: 1)
Prepare L2HClO4；2) by L2HClO4Prepare [NiL] (ClO4)2
1) C16H32N4·2HClO4(L2HClO4) synthesis:
C16H32N4·2HClO4(L2HClO4) synthesis.By the method for document, the reaction is always under condition of ice bath
It carries out.98.5mL ethylenediamine is added in the three-necked bottle of 500 mL, 126 mL70% perchloric acid are slowly added dropwise with dropping funel, adjusts
The mixing speed for saving magnetic stirring apparatus is 500r/min.Initial reaction is violent and generates with white cigarette, so rate of addition control
System is dripped in every five seconds clock 1, is formed icicle if too fast solution is added dropwise in funnel bottom and is caused funnel blockade.As reaction carries out
White cigarette gradually decreases, and the severe degree of reaction, which also gradually mitigates, can suitably accelerate rate of addition, until dripping, obtains
Transparent solution.Be added and 224 mL anhydrous propanones and be vigorously stirred to the clear solution, solution become cloudy quickly be formed simultaneously it is non-
Normal viscous mixture.Mixing speed should be properly increased at this time, and adjusting mixing speed is 1000r/min, still in ice-water bath
Under the conditions of kept for 2-3 hours sufficiently to react.Milk yellow viscous fluid is finally obtained, gained viscous fluid is transferred to Buchner funnel
Suction filtration separation is carried out, and is sufficiently washed with acetone, pure white solid can be obtained.By this pure white solid in hot methanol-water solution
Middle recrystallization, is dried in vacuo with silica-gel desiccant, obtains 80 g white crystals, this white crystal is L2HClO4。
Bibliography:
1.Curtis, N. F. and Hay, R. W. , J. Chem. Soc. , Chem. Commun. ,
1966, p. 534.
2.Gang Hu, Panpan Chen, Wei Wang, Lin Hu, Jimei Song, Lingguang Qiu,
Juan Song, E1ectrochimica Acta, 2007, Vol. 52, pp. 7996-8002.
3. Lin Hu, Gang Hu, Han-Hong Xu, J. Ana1. Chem. , 2006, Vol. 61, NO.
10, pp. 1021-1025.
4. Hu Gang, China Science & Technology University's doctoral thesis, p25-27, Hefei, 2005.
2) [NiL(C16H32N4)]·(ClO4)2Synthesis:
( [NiL](ClO4)2) synthesis.By the method for document, it is separately added into 11g Ni (AC)24H2The L of O and 21g
2HClO4It is placed in 1000mL three-necked bottle, adds the methanol of 500mL.After hot bath is heated to reflux 3-4 hours, it is heavy to there is yellow
It forms sediment.Yellow mercury oxide is filtered, filtrate is concentrated into original volume 1/2-1/3 in hot bath, stands overnight.It, can be with after sufficient crystallising
Obtain yellow crystals.Yellow crystals are transferred to Buchner funnel ethanol washing, are recrystallized in the ethanol-water solution of heat, very
Sky is dry, can obtain about 8 g [NiL] (ClO4)2Glassy yellow crystal.
Bibliography:
1. N. F. Curtis, J. Chem. Soc. Dolton Tran. , 1972, Vol. 13, 1357.
2. Hu Gang, China Science & Technology University's doctoral thesis, p42-43, Hefei, 2005.
Detection method difference with the prior art of the present invention is that the present invention is using " H2SO4 KIO3-[NiL]
(ClO4)2Malonic acid-H2O2" nonlinear chemical oscillation system is as solution is identified, according to aromatic isomer 2- hydroxyl
Benzoic acid and 3- hydroxybenzoic acid realize same to aromatic series the difference of acumen oscillatory response caused by the reaction system
The differentiation of enantiomers identifies.Aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid identify in solution can
Identifying concentration range is 1.0 × 10-5 - 2.2 × 10-4Mol/L, it is tests determined optimal that this, which can identify concentration range,
Concentration range, the response that 2 hydroxybenzoic acid generates oscillation in the concentration range are very clear obvious, it is easy to Ji Keshi
Now identify；It is as shown in table 1 to identify each component concentration in solution, as shown in table 2 through the determining optium concentration of test of many times:
Table 1: the concentration range of each component in oscillation system
| Sulfuric acid (mol/L) | Potassiumiodate (mol/L) | [NiL](ClO4)2 (mol/L) | Malonic acid (mol/L) | Hydrogen peroxide (mol/L) |
| 0.0195-0.026 | 0.0179-0.0195 | 6.86×10-4-9.15×10-4 | 0.165-0.1925 | 1.28-1.33 |
Table 2: the optium concentration of each component in oscillation system
| Sulfuric acid (mol/L) | Potassiumiodate (mol/L) | [NiL](ClO4)2 (mol/L) | Malonic acid (mol/L) | Hydrogen peroxide (mol/L) |
| 0.026 | 0.01925 | 9.15×10-4 | 0.165 | 1.33 |
Concrete operations are as follows:
1, it is prepared by solubility best in table and identifies solution, and recorded the E-t curve that the solution potential changes over time and change
Learn electrical oscillation map.
Firstly, taking in a 50 mL small beakers and being put into sizeable magneton, it is placed on constant temperature magnetic heating stirrer
On, speed is kept stirring in 500 r/min.Oscillation system each component solution is added into beaker.Ready working electrode
(platinum electrode) and reference electrode (double salt bridge calomel electrodes) are inserted into beaker, and working electrode and reference electrode pass through amplifier
(Instrument Amplifier) is connected to data collector (GO!LINK it) is then connected on computer by USB again.It opens
Computer equipped with logger lite software, using logger lite software to solution potential change with time situation carry out
(sample to be tested is not yet added) in acquisition in real time at this time, to make blank control.Vibrating any one stable current potential of generation most
At low spot, into two groups of oscillation systems identical with each component concentration in blank control experiment, it is rapidly added respectively to be identified
The solution of sample, according to sample to be identified to the difference of oscillatory response caused by oscillation system, sample to be identified is determined in realization
Property analysis.That is: after being separately added into the solution of sample to be identified into two groups of oscillation systems, if the amplitude of oscillation of oscillation system omits
Have reduction and cycle of oscillation be elongated, then the sample to be identified be 2 hydroxybenzoic acid, and if oscillation system is not influenced,
The sample to be identified is 3- hydroxybenzoic acid.
Chemical potential oscillation map basic parameter include:
Amplitude of oscillation: in oscillatory process from a potential minimum to the potential difference next maximum potential.
Cycle of oscillation: in oscillatory process the time required to from minimum (height) current potential to next minimum (height) current potential.
Maximum potential: the current potential highest point that system occurs when stable oscillation stationary vibration.
Potential minimum: the current potential minimum point that system occurs when stable oscillation stationary vibration.
Inhibit the time: after addition prepare liquid, vibrating suppressed to recovery oscillation required time again.
Detailed description of the invention
Fig. 1 is when sample to be identified not being added, to identify the oscillation map of solution (oscillation system) in embodiment 1.
Fig. 2, Fig. 3 are to be separately added into 1.2 × 10 in embodiment 1-4Mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid
Afterwards, oscillation system oscillatory response map obtained.
Fig. 4 is when sample to be identified not being added, to identify the oscillation map of solution (oscillation system) in embodiment 2.
Fig. 5, Fig. 6 are to be separately added into 1.4 × 10 in embodiment 2-4Mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid
Afterwards, oscillation system oscillatory response map obtained.
Fig. 7 is when sample to be identified not being added, to identify the oscillation map of solution (oscillation system) in embodiment 3.
Fig. 8, Fig. 9 are to be separately added into 2.0 × 10 in embodiment 3-4Mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid
Afterwards, oscillation system oscillatory response map obtained.
Figure 10 is when sample to be identified not being added, to identify the oscillation map of solution (oscillation system) in embodiment 4.
Figure 11, Figure 12 are to be separately added into 2.1 × 10 in embodiment 4-4Mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid
Afterwards, oscillation system oscillatory response map obtained.
Figure 13 is when sample to be identified not being added, to identify the oscillation map of solution (oscillation system) in embodiment 5.
Figure 14, Figure 15 are to be separately added into 1.6 × 10 in embodiment 5-4Mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid
Afterwards, oscillation system oscillatory response map obtained.
Specific embodiment
Embodiment 1:
The present embodiment verifies aromatic isomer 2 hydroxybenzoic acid and 3- hydroxy benzenes first of the present invention as follows
The feasibility of the discrimination method of acid:
(1) solution is prepared
Use first 98% the concentrated sulfuric acid and distilled water prepare 0.026mol/L sulfuric acid as stock solution, then use
The sulfuric acid solution of 0.026mol/L prepares [NiL] of the potassium iodate solution of 0.13mol/L, 0.0183mol/L as solvent respectively
(ClO4)2Solution, the malonic acid solution of 2.2mol/L, 3.8mol/L hydrogenperoxide steam generator.
Simultaneously with second distillation water as solvent, 0.12mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid are prepared respectively
Solution.
(2) map is vibrated
Magneton is added into 50mL small beaker, sequentially adds 15mL 0.026mol/L sulfuric acid solution, 6mL 0.13mol/
L potassium iodate solution, 2mL 0.0183mol/L [NiL] (ClO4)2Solution, 3mL 2.2mol/L malonic acid are molten, are eventually adding 14mL
3.8mol/L hydrogenperoxide steam generator, maintenance system total volume are 40mL, guarantee " H2SO4-KIO3-[NiL](ClO4)2 Malonic acid-
H2O2" in system, the molar concentration of each component is respectively sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL]
(ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L.With equipped with logger lite journey
The computer of sequence records the oscillation map that current potential changes over time.
Fig. 1 is (sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL] (ClO under typical concentration4)2 9.15×
10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L), the oscillation of sample to be tested is not added for above-mentioned identification solution
Map, to make blank control.The color of observation oscillation solution can be found that the continuous generating period variation of the color of solution: yellow
Color-brown color-yellow, and periodic variation is also presented in potential.
Take one group of each component concentration identification solution (sulfuric acid 0.026mol/L, Potassiumiodate identical with above-mentioned concentration
0.0195mol/L、[NiL](ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L),
When oscillation map reaches the 5th current potential minimum point, 40uL 0.12mol/L 2 hydroxybenzoic acid is added with liquid-transfering gun, so that
It is 1.2 × 10 identifying the concentration in solution-4Mol/L, resulting oscillatory response map are as shown in Figure 2.
Another group of each component concentration identification solution identical with above-mentioned concentration is taken, reaches the 5th current potential most in oscillation map
When low spot, 40uL 0.12mol/L 3- hydroxybenzoic acid is added with liquid-transfering gun, so that it is 1.2 identifying the concentration in solution
×10-4Mol/L, resulting oscillatory response map are as shown in Figure 3.
(3) it distinguishes and identifies
As aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid to reaction due to molecular structure difference
The difference of system generation oscillatory response.As shown in Figure 2, compared to Figure 1, the addition of 2 hydroxybenzoic acid is to oscillation map and its base
This parameter influences very big: amplitude of oscillation slightly reduces and cycle of oscillation (T) is elongated；It is identical dense and from the figure 3, it may be seen that compared to Figure 1
The addition of the 3- hydroxybenzoic acid of degree does not influence oscillation map and its basic parameter.It is found that it can root by above-mentioned identification experiment
Realize that the differentiation to 2 hydroxybenzoic acid and 3- hydroxybenzoic acid identifies according to the difference of oscillatory response map.
Take the sample to be identified of two 0.12mol/L prepared in advance solution (one of them for 2 hydroxybenzoic acid it is molten
Liquid, another is 3- hydroxybenzoic acid solution, but the two is not yet distinguished), it is 1 by one of label, another label
For sample 2；
Two groups of each component concentration identification solution identical with above-mentioned concentration is prepared, respectively the corresponding oscillation map of acquisition, and
The sample 1 and sample 2 of 40uL 0.12mol/L are separately added at the 5th current potential minimum point, so that they are in identifying solution
Concentration be 1.2 × 10-4mol/L。
Known to analysis relatively: the oscillation map of sample 1 is compared with Fig. 1, and amplitude of oscillation slightly reduces and cycle of oscillation
(T) elongated, it is corresponding with Fig. 2, do not corresponded to Fig. 3, therefore sample 1 is 2 hydroxybenzoic acid.The oscillation map of sample 2 with
Fig. 1 is corresponding with Fig. 3, do not correspond to Fig. 2 compared to more not changing, therefore sample 2 is 3- hydroxybenzoic acid.Therefore, according to
The difference of oscillatory response map realizes the differentiation to isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid.
Embodiment 2:
The present embodiment verifies aromatic isomer 2 hydroxybenzoic acid and 3- hydroxy benzenes first of the present invention as follows
The feasibility of the discrimination method of acid:
(1) solution is prepared
Use first 98% the concentrated sulfuric acid and distilled water prepare 0.026mol/L sulfuric acid as stock solution, then use
The sulfuric acid solution of 0.026mol/L prepares [NiL] of the potassium iodate solution of 0.13mol/L, 0.0183mol/L as solvent respectively
(ClO4)2Solution, the malonic acid solution of 2.2mol/L, 3.8mol/L hydrogenperoxide steam generator.
Simultaneously with second distillation water as solvent, the 2 hydroxybenzoic acid and 3- hydroxybenzoic acid of 0.14mol/L are prepared respectively
Solution.
(2) map is vibrated
Magneton is added into 50mL small beaker, sequentially add 5.5mL 0.026mol/L sulfuric acid solution, 10mL distilled water,
5.5mL 0.13mol/L potassium iodate solution, 2mL 0.0183mol/L [NiL] (ClO4)2Solution, 3mL 2.2mol/L malonic acid
It is molten, it is eventually adding 14mL 3.8mol/L hydrogen peroxide, maintenance system total volume is 40mL, guarantees " H2SO4-KIO3-[NiL]
(ClO4)2 Malonic acid-H2O2" in system, the molar concentration of each component is respectively sulfuric acid 0.0195mol/L, Potassiumiodate
0.0179mol/L、[NiL](ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L.With
Computer equipped with logger lite program records the oscillation map that current potential changes over time.
Fig. 4 is to identify solution (sulfuric acid 0.0195mol/L, Potassiumiodate 0.0179mol/L, [NiL] (ClO4)2 9.15×10- 4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L) the oscillation map of sample to be tested is not added, to make blank pair
According to.The color of observation oscillation solution can be found that the continuous generating period variation of the color of solution: yellow-brown color-yellow,
And periodic variation is also presented in potential.
Take one group of each component concentration identification solution (sulfuric acid 0.0195mol/L, Potassiumiodate identical with above-mentioned concentration
0.0179mol/L、[NiL](ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L),
When oscillation map reaches the 5th current potential minimum point, 40uL 0.14mol/L 2 hydroxybenzoic acid is added with liquid-transfering gun, so that its
It is 1.4 × 10 identifying the concentration in solution-4Mol/L, resulting oscillatory response map are as shown in Figure 5.
Another group of each component concentration identification solution identical with above-mentioned concentration is taken, reaches the 5th current potential most in oscillation map
When low spot, 40uL 0.14mol/L 3- hydroxybenzoic acid is added with liquid-transfering gun, so that it is 1.4 identifying the concentration in solution
×10-4Mol/L, resulting oscillatory response map are as shown in Figure 6.
(3) it distinguishes and identifies
As aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid to anti-due to molecular structure difference
System is answered to generate the difference of oscillatory response.As shown in Figure 5, compared with Fig. 4, the addition of 2 hydroxybenzoic acid to oscillation map and its
Basic parameter influences very big: amplitude of oscillation slightly reduces and cycle of oscillation (T) is elongated；It is identical and it will be appreciated from fig. 6 that compared with Fig. 4
The addition of the 3- hydroxybenzoic acid of concentration does not influence oscillation map and its basic parameter.By above-mentioned identification experiment it is found that can
Realize that the differentiation to 2 hydroxybenzoic acid and 3- hydroxybenzoic acid identifies according to the difference of oscillatory response map.
Take the sample to be identified of two 0.14mol/L prepared in advance solution (one of them for 2 hydroxybenzoic acid it is molten
Liquid, another is 3- hydroxybenzoic acid solution, but the two is not yet distinguished), it is 1 by one of label, another label
For sample 2；
Two groups of each component concentration identification solution identical with above-mentioned concentration is prepared, respectively the corresponding oscillation map of acquisition, and
The sample 1 and sample 2 of 40uL 0.14mol/L are separately added at the 5th current potential minimum point, so that they are in identifying solution
Concentration be 1.4 × 10-4mol/L。
Known to analysis relatively: the oscillation map of sample 1 is compared with Fig. 4, and amplitude of oscillation slightly reduces and cycle of oscillation
(T) elongated, it is corresponding with Fig. 5, do not corresponded to Fig. 6, therefore sample 1 is 2 hydroxybenzoic acid.The oscillation map of sample 2 with
Fig. 4 is corresponding with Fig. 6, do not correspond to Fig. 5 compared to more not changing, therefore sample 2 is 3- hydroxybenzoic acid.Therefore, according to vibration
The difference for swinging response map, realizes the differentiation to isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid.
Embodiment 3:
The present embodiment verifies aromatic isomer 2 hydroxybenzoic acid and 3- hydroxy benzenes first of the present invention as follows
The feasibility of the discrimination method of acid:
(1) solution is prepared
Use first 98% the concentrated sulfuric acid and distilled water prepare 0.026mol/L sulfuric acid as stock solution, then use
The sulfuric acid solution of 0.026mol/L prepares [NiL] of the potassium iodate solution of 0.13mol/L, 0.0183mol/L as solvent respectively
(ClO4)2Solution, the malonic acid solution of 2.2mol/L, 3.8mol/L hydrogenperoxide steam generator.
Simultaneously with second distillation water as solvent, 2 hydroxybenzoic acid and the 3- hydroxybenzoic acid for preparing 0.2mol/L respectively are molten
Liquid.
(2) map is vibrated
Magneton is added into 50mL small beaker, sequentially adds 15mL 0.026mol/L sulfuric acid solution, 6mL 0.13mol/
L potassium iodate solution, 1.5mL 0.0183mol/L [NiL] (ClO4)2Solution, 3.5mL 2.2mol/L malonic acid are molten, are eventually adding
14mL 3.8mol/L hydrogenperoxide steam generator, maintenance system total volume are 40mL, guarantee " H2SO4-KIO3-[NiL](ClO4)2- the third
Diacid-H2O2" in system, the molar concentration of each component is respectively sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL]
(ClO4)2 6.86×10-4Mol/L, malonic acid 0.1925mol/L, hydrogen peroxide 1.33mol/L.With equipped with logger lite journey
The computer of sequence records the oscillation map that current potential changes over time.
Fig. 7 is to identify solution (sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL] (ClO4)2 6.86×10- 4Mol/L, malonic acid 0.1925mol/L, hydrogen peroxide 1.33mol/L) the oscillation map of sample to be tested is not added, to make blank
Control.The color of observation oscillation solution can be found that the continuous generating period variation of the color of solution: yellow-brown color-Huang
Color, and periodic variation is also presented in potential.
Take one group of each component concentration identification solution (sulfuric acid 0.026mol/L, Potassiumiodate identical with above-mentioned concentration
0.0195mol/L、[NiL](ClO4)2 6.86×10-4Mol/L, malonic acid 0.1925mol/L, hydrogen peroxide 1.33mol/L),
When oscillation map reaches the 5th current potential minimum point, 40uL 0.2mol/L 2 hydroxybenzoic acid is added with liquid-transfering gun, so that its
It is 2.0 × 10 identifying the concentration in solution-4Mol/L, resulting oscillatory response map are as shown in Figure 8.
Another group of each component concentration identification solution identical with above-mentioned concentration is taken, reaches the 5th current potential most in oscillation map
When low spot, with liquid-transfering gun be added 40uL 0.2mol/L 3- hydroxybenzoic acid so that its identify solution in concentration be 2.0 ×
10-4Mol/L, resulting oscillatory response map are as shown in Figure 9.
(3) it distinguishes and identifies
As aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid to anti-due to molecular structure difference
System is answered to generate the difference of oscillatory response.As shown in Figure 8, compared with Fig. 7, the addition of 2 hydroxybenzoic acid to oscillation map and its
Basic parameter influences very big: amplitude of oscillation slightly reduces and cycle of oscillation (T) is elongated；And as shown in Figure 9, it is identical compared with Fig. 7
The addition of the 3- hydroxybenzoic acid of concentration does not influence oscillation map and its basic parameter.By above-mentioned identification experiment it is found that can
Realize that the differentiation to 2 hydroxybenzoic acid and 3- hydroxybenzoic acid identifies according to the difference of oscillatory response map.
Take the sample to be identified of two 0.2mol/L prepared in advance solution (one of them for 2 hydroxybenzoic acid it is molten
Liquid, another is 3- hydroxybenzoic acid solution, but the two is not yet distinguished), it is 1 by one of label, another label
For sample 2；
Two groups of each component concentration identification solution identical with above-mentioned concentration is prepared, respectively the corresponding oscillation map of acquisition, and
The sample 1 and sample 2 of 40uL 0.2mol/L are separately added at the 5th current potential minimum point, so that they are in identifying solution
Concentration is 2.0 × 10-4mol/L。
Known to analysis relatively: the oscillation map of sample 1 is compared with Fig. 7, and amplitude of oscillation slightly reduces and cycle of oscillation
(T) elongated, it is corresponding with Fig. 8, do not corresponded to Fig. 9, therefore sample 1 is 2 hydroxybenzoic acid.The oscillation map of sample 2 with
Fig. 7 is corresponding with Fig. 9, do not correspond to Fig. 8 compared to more not changing, therefore sample 2 is 3- hydroxybenzoic acid.Therefore, according to
The difference of oscillatory response map realizes the differentiation to isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid.
Embodiment 4:
The present embodiment verifies aromatic isomer 2 hydroxybenzoic acid and 3- hydroxy benzenes first of the present invention as follows
The feasibility of the discrimination method of acid:
(1) solution is prepared
Use first 98% the concentrated sulfuric acid and distilled water prepare 0.026mol/L sulfuric acid as stock solution, then use
The sulfuric acid solution of 0.026mol/L prepares [NiL] of the potassium iodate solution of 0.13mol/L, 0.0183mol/L as solvent respectively
(ClO4)2Solution, the malonic acid solution of 2.2mol/L, 3.8mol/L hydrogenperoxide steam generator.
Simultaneously with second distillation water as solvent, the 2 hydroxybenzoic acid and 3- hydroxybenzoic acid of 0.21mol/L are prepared respectively
Solution.
(2) map is vibrated
Magneton is added into 50mL small beaker, sequentially adds 15.5mL 0.026mol/L sulfuric acid solution, 6mL
0.13mol/L potassium iodate solution, 2mL 0.0183mol/L [NiL] (ClO4)2Solution, 3mL 2.2mol/L malonic acid are molten, finally
13.5mL 3.8mol/L hydrogenperoxide steam generator is added, maintenance system total volume is 40mL, guarantees " H2SO4-KIO3-[NiL]
(ClO4)2Malonic acid-H2O2" in system, the molar concentration of each component is respectively sulfuric acid 0.026mol/L, Potassiumiodate
0.0195mol/L、[NiL](ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.28mol/L.With
Computer equipped with logger lite program records the oscillation map that current potential changes over time.
Figure 10 is to identify solution (sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL] (ClO4)2 9.15×10- 4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.28mol/L) the oscillation map of sample to be tested is not added, to make blank pair
According to.The color of observation oscillation solution can be found that the continuous generating period variation of the color of solution: yellow-brown color-yellow,
And periodic variation is also presented in potential.
Take one group of each component concentration identification solution (sulfuric acid 0.026mol/L, Potassiumiodate identical with above-mentioned concentration
0.0195mol/L、[NiL](ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.28mol/L),
When oscillation map reaches the 5th current potential minimum point, 40uL 0.21mol/L 2 hydroxybenzoic acid is added with liquid-transfering gun, so that its
It is 2.1 × 10 identifying the concentration in solution-4Mol/L, resulting oscillatory response map are as shown in figure 11.
Another group of each component concentration identification solution identical with above-mentioned concentration is taken, reaches the 5th current potential most in oscillation map
When low spot, 40uL 0.21mol/L 3- hydroxybenzoic acid is added with liquid-transfering gun, so that it is 2.1 identifying the concentration in solution
×10-4Mol/L, resulting oscillatory response map are as shown in figure 12.
(3) it distinguishes and identifies
As aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid to anti-due to molecular structure difference
System is answered to generate the difference of oscillatory response.As shown in Figure 11, compared with Figure 10, the addition of 2 hydroxybenzoic acid to oscillation map and
Its basic parameter influences very big: amplitude of oscillation slightly reduces and cycle of oscillation (T) is elongated；And as shown in Figure 12, compared with Figure 10,
The addition of the 3- hydroxybenzoic acid of same concentrations does not influence oscillation map and its basic parameter.It can by above-mentioned identification experiment
Know, can realize that the differentiation to 2 hydroxybenzoic acid and 3- hydroxybenzoic acid identifies according to the difference of oscillatory response map.
Take the sample to be identified of two 0.21mol/L prepared in advance solution (one of them for 2 hydroxybenzoic acid it is molten
Liquid, another is 3- hydroxybenzoic acid solution, but the two is not yet distinguished), it is 1 by one of label, another label
For sample 2；
The identification solution of two groups of above-mentioned concentration is prepared, respectively the corresponding oscillation map of acquisition, and in the 5th current potential minimum point
Place is separately added into the sample 1 and sample 2 of 40 μ L 0.21mol/L, so that they are 2.1 × 10 identifying the concentration in solution- 4mol/L。
Known to analysis relatively: the oscillation map of sample 1 is compared with Figure 10, and amplitude of oscillation slightly reduces and cycle of oscillation
(T) elongated, it is corresponding with Figure 11, do not corresponded to Figure 12, therefore sample 1 is 2 hydroxybenzoic acid.The oscillation map of sample 2
More do not change compared with Figure 10, it is corresponding with Figure 12, do not corresponded to Figure 11, therefore sample 2 is 3- hydroxybenzoic acid.Cause
This realizes the differentiation to isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid according to the difference of oscillatory response map.
Embodiment 5:
The present embodiment verifies aromatic isomer 2 hydroxybenzoic acid and 3- hydroxy benzenes first of the present invention as follows
The feasibility of the discrimination method of acid:
(1) solution is prepared
Use first 98% the concentrated sulfuric acid and distilled water prepare 0.026mol/L sulfuric acid as stock solution, then use
The sulfuric acid solution of 0.026mol/L prepares [NiL] of the potassium iodate solution of 0.13mol/L, 0.0183mol/L as solvent respectively
(ClO4)2Solution, the malonic acid solution of 2.2mol/L, 3.8mol/L hydrogenperoxide steam generator.
Simultaneously with second distillation water as solvent, 0.16mol/L 2 hydroxybenzoic acid and 3- hydroxybenzoic acid are prepared respectively
Solution.
(2) map is vibrated
Magneton is added into 50mL small beaker, sequentially adds 15mL 0.026mol/L sulfuric acid solution, 6mL 0.13mol/
L potassium iodate solution, 2mL 0.0183mol/L [NiL] (ClO4)2Solution, 3mL 2.2mol/L malonic acid are molten, are eventually adding 14mL
3.8mol/L hydrogenperoxide steam generator, maintenance system total volume are 40mL, guarantee " H2SO4-KIO3-[NiL](ClO4)2Malonic acid-
H2O2" in system, the molar concentration of each component is respectively sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL]
(ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L.With equipped with logger lite journey
The computer of sequence records the oscillation map that current potential changes over time.
Figure 13 is in typical concentration (sulfuric acid 0.026mol/L, Potassiumiodate 0.0195mol/L, [NiL] (ClO4)2 9.15×
10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L) under, the vibration of sample to be tested is not added for above-mentioned identification solution
Map is swung, to make blank control.The color of observation oscillation solution can be found that the continuous generating period variation of the color of solution:
Yellow-brown color-yellow, and periodic variation is also presented in potential.
Take one group of each component concentration identification solution (sulfuric acid 0.026mol/L, Potassiumiodate identical with above-mentioned concentration
0.0195mol/L、[NiL](ClO4)2 9.15×10-4Mol/L, malonic acid 0.165mol/L, hydrogen peroxide 1.33mol/L),
When oscillation map reaches the 7th current potential minimum point, 40uL 0.16mol/L 2 hydroxybenzoic acid is added with liquid-transfering gun, so that
It is 1.6 × 10 identifying the concentration in solution-4Mol/L, resulting oscillatory response map are as shown in figure 14.
Another group of each component concentration identification solution identical with above-mentioned concentration is taken, reaches the 7th current potential most in oscillation map
When low spot, 40uL 0.16mol/L 3- hydroxybenzoic acid is added with liquid-transfering gun, so that it is 1.6 identifying the concentration in solution
×10-4Mol/L, resulting oscillatory response map are as shown in figure 15.
(3) it distinguishes and identifies
As aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid to anti-due to molecular structure difference
System is answered to generate the difference of oscillatory response.As shown in Figure 14, compared with figure 13, the addition of 2 hydroxybenzoic acid to oscillation map and
Its basic parameter influences very big: amplitude of oscillation slightly reduces and cycle of oscillation (T) is elongated；And as shown in Figure 15, compared with figure 13,
The addition of the 3- hydroxybenzoic acid of same concentrations does not influence oscillation map and its basic parameter.It can by above-mentioned identification experiment
Know, can realize that the differentiation to 2 hydroxybenzoic acid and 3- hydroxybenzoic acid identifies according to the difference of oscillatory response map.
Take the sample to be identified of two 0.16mol/L prepared in advance solution (one of them for 2 hydroxybenzoic acid it is molten
Liquid, another is 3- hydroxybenzoic acid solution, but the two is not yet distinguished), it is 1 by one of label, another label
For sample 2；
Prepare the identification solution of two groups of above-mentioned typical concentrations, respectively the corresponding oscillation map of acquisition, and the 7th current potential most
The sample 1 and sample 2 of 40 μ L 0.16mol/L are separately added at low spot so that they identify solution in concentration be 1.6 ×
10-4mol/L。
Known to analysis relatively: the oscillation map of sample 1 is compared with figure 13 compared with amplitude of oscillation slightly reduces and cycle of oscillation
(T) elongated, it is corresponding with Figure 14, do not corresponded to Figure 15, therefore sample 1 is 2 hydroxybenzoic acid.The oscillation map of sample 2
Less change compared with figure 13, it is corresponding with Figure 15, do not corresponded to Figure 14, therefore sample 2 is 3- hydroxybenzoic acid.Cause
This realizes the differentiation to isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid according to the difference of oscillatory response map.
As can be seen from the above embodiments, the 2 hydroxybenzoic acid of smaller or larger concentration and 3- hydroxybenzoic acid can also be with
Identified by the method for the invention.
Claims (3)
1. a kind of aromatic isomer 2 hydroxybenzoic acid and 3- hydroxybenzoic acid discrimination method, it is characterised in that:
Using secondary distilled water as solvent, the solution of sample to be identified is prepared；
Using " H2SO4 - KIO3 - [NiL](ClO4)2Malonic acid-H2O2" nonlinear chemical oscillation system as identify it is molten
Liquid records the oscillation map of oscillation system, at any one stable current potential minimum point that oscillation generates, to two groups of oscillating bodies
The solution of sample to be identified is separately added into system, it is real according to sample to be identified to the difference of oscillatory response caused by oscillation system
The now qualitative analysis to sample to be identified: if the amplitude of oscillation of oscillation system slightly reduces and cycle of oscillation T is elongated, it is described to
Identification sample is 2 hydroxybenzoic acid；If not influencing on oscillation system, the sample to be identified is 3- hydroxybenzoic acid；
[NiL](ClO4)2 Middle L is 5,7,7,12,14,14- vegolysen, tetra- azepine of 4,8,11-, 14-4,11- diene；
Identify the molar concentration of each component in solution are as follows: 0.0195-0.026mol/L of sulfuric acid, Potassiumiodate 0.0179-
0.0195mol/L、[NiL](ClO4)2 6.86×10-4-9.15×10-4Mol/L, malonic acid 0.165-0.1925mol/L, mistake
Hydrogen oxide 1.28-1.33mol/L；
The sample to be identified is 2 hydroxybenzoic acid and 3- hydroxybenzoic acid.
2. discrimination method according to claim 1, it is characterised in that: any one stable current potential that the oscillation generates
Minimum point refers to any one in the 3rd ~ 20 current potential minimum point that oscillation generates.
3. discrimination method according to claim 1, it is characterised in that: sample to be identified identify solution in identify it is dense
Spending range is 1.0 × 10-5-2.2×10-4mol/L。
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| CN104730138A (en) * | 2015-03-31 | 2015-06-24 | 嘉兴迪生电子科技有限公司 | Differentiating identification method of aromatic isomers 1,3-cyclohexanedione and 1,4-cyclohexanedione |
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