CN103675046A - Detection method of protocatechuic acid - Google Patents
Detection method of protocatechuic acid Download PDFInfo
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- CN103675046A CN103675046A CN201210329925.1A CN201210329925A CN103675046A CN 103675046 A CN103675046 A CN 103675046A CN 201210329925 A CN201210329925 A CN 201210329925A CN 103675046 A CN103675046 A CN 103675046A
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Abstract
The invention discloses a novel detection method of protocatechuic acid. The method is characterized in that a classical nonlinear chemical oscillation system (components 'NaBrO3-MA-H2SO4-[CuL](ClO4)2') is utilized as a detection solution, and a work curve is built by an oscillation response of the solution to protocatechuic acid, so as to achieve quantitative analysis of protocatechuic acid. L in a catalyst [CuL](ClO4)2 is 5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraaza 14-4,11-diene; the molar concentration range of each component in the detection solution is as follows: sodium bromate is 0.0018-0.175mol/L, malic acid is 0.005-0.8mol/L, sulfuric acid is 0.25-2.5mol/L, and [CuL](ClO4)2 is greater than or equal to 4.61*10<-4>mol/L. The method has the characteristics of good selectivity, high sensitivity, convenience and fastness, and the like.
Description
Technical field
The present invention relates to a kind of novel method of analyzing and testing protocatechuic acid, specifically set up a kind of with four nitrogen heterocyclic ring copper complexes-[CuL] (ClO
4)
2for the classical nonlinear chemical oscillation system of catalyzer, by system, the respective change that adds variable concentrations protocatechuic acid to produce is accomplished the analysis of protocatechuic acid and mensuration.
Background technology
Protocatechuic acid, formal name used at school 3,4-dihydroxy-benzoic acid, it is extensively present in the Chinese herbal medicines such as rhizoma cibotii, Chinese ilex, Stenoloma chusana, it all has bacteriostasis in various degree to Pseudomonas aeruginosa, Escherichia coli, typhoid bacillus, shigella dysenteriae, Bacillus alcaligenes and hay bacillus and staphylococcus aureus, and has convergence to promote the effect of wound healing.Therefore be used for the treatment of clinically burn, infantile pneumonia, bacillary dysentery, acute pancreatitis, chronic bronchitis.Simultaneously its part effect such as relieving asthma, eliminate the phlegm, antidote against snake bite is domestic also a relevant report.Protocatechuic acid is not only applied to medicine intermediate, dyestuff etc. also as a kind of analytical reagent, the at present domestic common concentration that detects protocatechuic acid by thin layer chromatography scanning, high performance liquid chromatography, reversed-phased high performace liquid chromatographic, fluorometry etc.
Summary of the invention
The present invention is intended to protocatechuic acid that a kind of new detection method is provided, with four nitrogen heterocyclic ring copper complexes-[CuL] (ClO
4)
2the nonlinear chemical oscillation system of catalysis detects the method for protocatechuic acid, this method according to being state variable (concentration due to oscillating reactions system, temperature, reaction rates etc.) generating period changes in time, when adding chaff interference in oscillation system, as long as can exert an influence to a certain elementary reaction of oscillating reactions, will interference oscillatory behavior, change the form of oscillating curve, the chemical information that this change is reflected is (as amplitude of oscillation, cycle, frequency etc.) analyze, set up the relation of this variable quantity and testing concentration, thereby analyze mensuration.Specifically the protocatechuic acid sample solution of a series of variable concentrations is joined in nonlinear chemical system, according to the variable concentrations of sample solution protocatechuic acid and the corresponding relation of the variation of corresponding vibration collection of illustrative plates, set up working curve and then realize sample is carried out to quantitative test.
Four alleged nitrogen heterocyclic ring copper complex catalyzer of the present invention are 5,7,7,12,14,14-vegolysens, 4,8,11-, tetra-nitrogen heterocyclic ring-4, and four nitrogen heterocyclic ring copper (II) complexs that 11-diene is part, have following chemical formula, and are denoted as [CuL] (ClO
4)
2:
This complex structure and life entity fillet Lactoferrin, haemoglobin, the key structure porphyrin ring of chlorophyll and some enzymes is very similar, this with [CuL] (ClO
4)
2biochemistry vibration in the chemical oscillating reaction of catalysis and plant and animal cell body is similar, and therefore, this system has stable amplitude, longer vibration life-span, and the acumen response to protocatechuic acid.
[CuL] (ClO
4)
2preparation divide two: 1) prepare L2HClO
4, 2) again by L2HClO
4preparation [CuL] (ClO
4)
2.
1) prepare L2HClO
4: 98.5mL ethylenediamine is packed in a 500mL three-necked bottle, under condition of ice bath, stir the lower 126mL70% perchloric acid that slowly drips in 120 minutes.Initial reaction acutely and with white cigarette produces, so rate of addition is controlled at 1 of every 5 second.Along with reaction is carried out suitably accelerating rate of addition, until drip, obtain transparent solution.Still under the condition of ice-water bath, to this clear solution, add 224mL anhydrous propanone vigorous stirring, solution becomes very soon muddiness and forms very viscous mixture simultaneously.Still under the condition of ice-water bath, keep 2-3 hour so that fully reaction.Products therefrom is transferred to Buchner funnel and carry out suction filtration separation, and fully wash with acetone, can obtain pure white solid.By this pure white solid recrystallization in hot methanol-water solution, use silica-gel desiccant vacuum drying, obtain 80g white crystal, this white crystal is L2HClO
4.(list of references:
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，Electrochimica?Acta，2007，Vol.52，pp.7996-8002.
3.Lin?Hu，Gang?Hu，Han-Hong?Xu，J.Anal.Chem.，2006，Vol.61，No.10，pp.1021-1025.
4. Hu Gang, China Science & Technology University's PhD dissertation, p25-27, Hefei, 2005)
2) preparation [CuL] (ClO
4)
2: in 1000mL three-necked bottle, add respectively 25.55g Cu (AC)
24H
2o (0.1mol) and equimolar L2HClO
4, then add in 800mL methyl alcohol.Hot bath added after hot reflux 3-4 hour, occurred red precipitate.Red precipitate is filtered, and filtrate is concentrated into original volume 1/2 in hot bath, and placement is spent the night.After sufficient crystallising, can obtain red crystals.Red crystals is transferred to Buchner funnel and with ethanol, washs, recrystallization in hot ethanol-water solution, vacuum drying, can red [Cu the L] (ClO of about 8g
4)
2crystal.(list of references
1.House，D.A.and?Curtis，N.F.，J.Am.Chem.Soc.，1964，vol.86，p.223.
2.Gang?Hu，Panpan?Chen，Wei?Wang，Lin?Hu，Jimei?S?ong，Lingguang?Qiu，Juan?Song，Electrochimica?Acta，2007，Vol.52，pp.7996-8002.
3. Hu Gang, China Science & Technology University's PhD dissertation, p25-27, Hefei, 2005)
This detection method difference with the prior art is application " NaBrO
3-MA (malic acid)-H
2sO
4-[CuL] (ClO
4)
2" Belousov-Zhbaotinskii oscillation system as detecting solution and this solution, the oscillatory response of protocatechuic acid is set up to working curve, and then realize the quantitative test of protocatechuic acid.In this solution, each component concentration ranges is as shown in table 1:
The concentration range of various solution in table 1Belousov-Zhabostinsky oscillating reactions system
Concrete operation step is as follows:
1, by the concentration range preparation of table 1 regulation, detecting solution and record the time dependent E-t curve of this solution potential is chemical potential vibration collection of illustrative plates
The detection solution preparing added in 50mL small beaker and puts into sizeable magneton, be placed on constant temperature magnetic force heating stirrer, keeping stirring rate at 500 revs/min, under water bath condition, making the temperature in beaker maintain 20-30 ℃.Then, ready working electrode (platinum electrode) and contrast electrode (two salt bridge mercurous chloride electrode) are inserted in solution, prepare solution to carry out potential monitoring.Finally, the corresponding software of opening on computer starts record data and vibration collection of illustrative plates.During detection, when vibration collection of illustrative plates reaches vibrational stabilization, add rapidly sample solution, conventionally when the 6th to the 8th vibration, add.
The basic parameter of vibration collection of illustrative plates comprises:
Induction time: add last a kind of material to the front needed time of solution starting of oscillation
Amplitude of oscillation: in oscillatory process from a potential minimum to the current potential difference next peak position.
Oscillation period: put position required time from one minimum (height) some position to next minimum (height) in oscillatory process.
Maximum potential: the current potential maximal value that during stable oscillation stationary vibration, system occurs.
Potential minimum: the potential minimum that during stable oscillation stationary vibration, system occurs.
The vibration life-span: self-oscillation starts to finish the needed time to vibration.
Equilibrium potential: current potential when system reaches thermodynamic equilibrium state.This moment, current potential does not change over time.
2, set up the working curve between concentration of specimens and oscillatory response variable quantity
Preparation series concentration is 3.125 * 10
-6mol/L～1.0 * 10
-4the protocatechuic acid solution of mol/L is as sample solution.The sample solution preparing is added in the oscillation system of stable oscillation stationary vibration, the variable quantity of oscillatory response is that amplitude of oscillation increases or maximum potential increases.Amplitude of oscillation increase value Δ A is defined as Δ A=A
1-A
0, in formula, A
0for adding the determinand amplitude of oscillation of oscillation system before, A
1for adding the amplitude of oscillation of oscillation system after protocatechuic acid; Maximum potential increase value Δ E is defined as Δ E=E
1-E
0, in formula, E
0for adding the determinand maximum potential of oscillation system before, E
1for adding the maximum potential of oscillation system after protocatechuic acid.
Take sample solution concentration as horizontal ordinate, take the logarithm value 1g (Δ A) of Δ A or the logarithm value 1g (Δ E) of Δ E as ordinate mapping, obtain working curve.
3, the quantitative test of protocatechuic acid
Sample to be tested is added in the oscillation system of stable oscillation stationary vibration, (sample to be tested all adds when the potential minimum of the 6th time to the 8th time vibration), oscillatory response is that amplitude of oscillation or maximum potential increase, and obtains Δ A value or Δ E value.According to the corresponding relation between the logarithm value 1g (Δ E) of the logarithm value 1g of Δ A on working curve (Δ A) or Δ E and concentration, can try to achieve the concentration of sample to be tested protocatechuic acid.
This method can detect the content of medicine intermediate protocatechuic acid quickly and easily, and experiment shows, other materials in sample are noiseless to detecting.
Accompanying drawing explanation
Fig. 1, Fig. 4, Fig. 7 are the chemical potential vibration collection of illustrative plates of nonlinear chemical oscillation system solution in embodiment 1,2,3 successively.
Fig. 2, Fig. 5, Fig. 8 add 6.0 * 10 in the oscillation system of embodiment 1,2,3
-5mol/L, 1.25 * 10
-5mol/L and 4.25 * 10
-5system oscillatory response collection of illustrative plates after mol/L protocatechuic acid.
Fig. 3, Fig. 6, Fig. 9 are the working curve that embodiment 1,2,3 sets up successively.
Embodiment
Embodiment 1:
Application NaBrO
3-MA (malic acid)-H
2sO
4-[CuL] (ClO
4)
2belousov-Zhbaotinskii oscillation system as detecting solution, protocatechuic acid is carried out to quantitative test.Add the protocatechuic acid sample solution of serial different content in oscillation system, set up measured object concentration and parameter of oscillation changing value between associated working curve (as linear relationship chart), reach the object of test samples protocatechuic acid content.
(1) obtain solution
Prepare respectively 2mol/L sulfuric acid solution, the sodium bromate solution of 0.5mol/L, the malic acid solution of 2.0mol/L, 1.84 * 10
-2[CuL] (ClO of mol/L
4)
2solution.Then, to the sulfuric acid solution that successively adds 20ml, 2.0mol/L in the open system of 50ml beaker, the sodium bromate solution of 1.2ml, 0.5mol/L, the malic acid solution of 4.5ml, 2.0mol/L, 8.5ml, 1.84 * 10
-2the catalyst solution of mol/L.Finally, in system, the concentration of sulfuric acid is 1.0mol/L, and the concentration of sodium bromate is 0.0150mol/L, and the concentration of malic acid is 0.225mol/L, and the concentration of catalyzer is 3.91 * 10
-3mol/L.
Prepare the protocatechuic acid sample solution of serial variable concentrations simultaneously.
(2) obtain vibration collection of illustrative plates
Registering instrument or the computer recording for vibration collection of illustrative plates of the oscillation system preparing.As shown in Figure 1.In the vibration solution preparing, add micro-protocatechuic acid solution, the time at every turn adding is all the 7th the amplitude potential minimum place producing in stable oscillation stationary vibration.It is that oscillatory response increases amplitude of oscillation that the protocatechuic acid adding can participate in oscillating reactions.As shown in Figure 2.
(3) analyze
Follow according to relation between the addition of system protocatechuic acid and the logarithm value of maximum potential increase value and set up working curve.As shown in Figure 3.Wherein horizontal ordinate is the concentration of vibration solution protocatechuic acid, and ordinate is the logarithm value 1g (Δ E) of maximum potential increase value.When the concentration of protocatechuic acid is 1.5 * 10
-5to 1.0 * 10
-4in the time of between mol/L, protocatechuic acid solution concentration becomes once linear relationship with 1g Δ E.Can realize the quantitative test to sample protocatechuic acid accordingly.
Embodiment 2:
(1) obtain solution
Prepare respectively 2mol/L sulfuric acid solution, the sodium bromate solution of 0.5mol/L, the malic acid solution of 2.0mol/L, 1.84 * 10
-2[CuL] (ClO of mol/L
4)
2solution.Then, to the sulfuric acid solution that successively adds 20ml, 2.0mol/L in the open system of 50ml beaker, the sodium bromate solution of 1.2ml, 0.5mol/L, the malic acid solution of 4.5ml, 2.0mol/L, 7.0ml, 1.84 * 10
-2the catalyst solution of mol/L.Finally, in system, the concentration of sulfuric acid is 1.0mol/L, and the concentration of sodium bromate is 0.0150mol/L, and the concentration of malic acid is 0.225mol/L, and the concentration of catalyzer is 3.22 * 10
-3mol/L.
Prepare the protocatechuic acid sample solution of serial variable concentrations simultaneously.
(2) obtain vibration collection of illustrative plates
Registering instrument or the computer recording for vibration collection of illustrative plates of the oscillation system preparing.As shown in Figure 4.The protocatechuic acid solution that adds variable concentrations in the vibration solution preparing, the time at every turn adding is all the 6th the amplitude potential minimum place producing in stable oscillation stationary vibration, the protocatechuic acid adding and oscillating reactions are that oscillatory response increases amplitude of oscillation.As shown in Figure 5.
(3) analyze
According to the relation value between the addition of protocatechuic acid and the logarithm value of amplitude increase value, set up working curve, as shown in Figure 6.Wherein horizontal ordinate is the concentration of protocatechuic acid, and ordinate is the logarithm value 1g (Δ A) that adds the increase value of amplitude of oscillation after protocatechuic acid.When the concentration of protocatechuic acid is 3.125 * 10
-6to 1.25 * 10
-5in the time of between mol/L, protocatechuic acid solution concentration becomes once linear relationship with 1g Δ A.Can realize the quantitative test to sample protocatechuic acid accordingly.
Embodiment 3
(1) obtain solution
Prepare respectively 2mol/L sulfuric acid solution, the sodium bromate solution of 0.5mol/L, the malic acid solution of 2.0mol/L, 1.84 * 10
-2[CuL] (ClO of mol/L
4)
2solution.Then, to the sulfuric acid solution that successively adds 20ml, 2.0mol/L in the open system of 50ml beaker, the sodium bromate solution of 1.0ml, 0.5mol/L, the malic acid solution of 4.5ml, 2.0mol/L, 8.5ml, 1.84 * 10
-2the catalyst solution of mol/L.Finally, in system, the concentration of sulfuric acid is 1.0mol/L, and the concentration of sodium bromate is 0.0125mol/L, and the concentration of malic acid is 0.225mol/L, and the concentration of catalyzer is 3.91 * 10
-3mol/L.
Prepare the protocatechuic acid sample solution of serial variable concentrations simultaneously.
(2) obtain vibration collection of illustrative plates
Registering instrument or the computer recording for vibration collection of illustrative plates of the oscillation system preparing.As shown in Figure 7.The protocatechuic acid solution that adds variable concentrations in the vibration solution preparing, the time at every turn adding is all the 7th the amplitude potential minimum place producing in stable oscillation stationary vibration, the protocatechuic acid adding and oscillating reactions are that oscillatory response increases amplitude of oscillation.As shown in Figure 8.
(3) analyze
According to the relation value between the addition of protocatechuic acid and the logarithm value of amplitude increase value, set up working curve, as shown in Figure 9.Wherein horizontal ordinate is the concentration of protocatechuic acid, and ordinate is the logarithm value 1g (Δ A) that adds the increase value of amplitude of oscillation after protocatechuic acid.When the concentration of protocatechuic acid is 1.25 * 10
-5to 4.25 * 10
-5in the time of between mol/L, protocatechuic acid solution concentration becomes once linear relationship with 1g Δ A.Can realize the quantitative test to sample protocatechuic acid accordingly.
Claims (3)
1. a method that detects protocatechuic acid, is characterized in that: (it forms " NaBrO to apply a kind of nonlinear chemical oscillation system of classics
3-MA-H
2sO
4-[CuL] (ClO
4)
2") as detecting solution and this solution, the oscillatory response of protocatechuic acid is set up to working curve, and then realize the quantitative test to protocatechuic acid.Catalyzer [CuL] (ClO
4)
2middle L is 5,7,7,12,14,14-vegolysen, 4,8,11-, tetra-azepines 14-4,11-diene; The volumetric molar concentration scope that detects each component in solution is sodium bromate 0.0018-0.175mol/L, malic acid 0.005-0.8mol/L, sulfuric acid 0.25-2.5mol/L, [CuL] (ClO
4)
2>=4.61 * 10
-4mol/L.
2. detection method according to claim 1, is characterized in that: to detecting solution, record chemical potential vibration collection of illustrative plates at 20-30 ℃, comprise induction time, amplitude of oscillation, oscillation period, maximum potential, potential minimum, vibration life-span, equilibrium potential.
3. detection method according to claim 1 and 2, is characterized in that: preparation series concentration is 3.125 * 10
-6mol/L-1.0 * 10
-4the protocatechuic acid solution of mol/L, as sample solution, is set up the working curve between sample solution and oscillatory response variable quantity, and horizontal ordinate is concentration of specimens, and ordinate is the logarithm value of amplitude variations amount or the logarithm value of maximum potential variable quantity.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN104730127A (en) * | 2015-03-31 | 2015-06-24 | 安徽大学 | Identification method of aliphatic chain isomer alpha-oxoglutarate and 1, 3-acetone dicarboxylic acid |
| CN106053564A (en) * | 2016-05-18 | 2016-10-26 | 南京师范大学 | Graphite phase nitrogen carbide-chitosan modified electrode, preparation method thereof, and method using same as work electrode to detect protocatechuic acid |
| CN107228888A (en) * | 2017-05-24 | 2017-10-03 | 安徽大学 | A kind of method for differentiating acetone and its isomer propionic aldehyde |
| CN113219025A (en) * | 2021-05-07 | 2021-08-06 | 安徽大学 | Method for quantitatively detecting potassium bromate |
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| CN109211979A (en) * | 2018-10-08 | 2019-01-15 | 上海应用技术大学 | A method of hydrogen peroxide is tested and analyzed using chemical oscillation |
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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 |
| CN104730127A (en) * | 2015-03-31 | 2015-06-24 | 安徽大学 | Identification method of aliphatic chain isomer alpha-oxoglutarate and 1, 3-acetone dicarboxylic acid |
| CN104730127B (en) * | 2015-03-31 | 2017-03-22 | 安徽大学 | Identification method of aliphatic chain isomer alpha-oxoglutarate and 1, 3-acetone dicarboxylic acid |
| CN104730138B (en) * | 2015-03-31 | 2017-04-12 | 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 |
| CN106053564A (en) * | 2016-05-18 | 2016-10-26 | 南京师范大学 | Graphite phase nitrogen carbide-chitosan modified electrode, preparation method thereof, and method using same as work electrode to detect protocatechuic acid |
| CN106053564B (en) * | 2016-05-18 | 2018-08-21 | 南京师范大学 | A kind of method that graphite-phase nitrogen carbide-chitosan-modified electrode detects protocatechuic acid as working electrode |
| CN107228888A (en) * | 2017-05-24 | 2017-10-03 | 安徽大学 | A kind of method for differentiating acetone and its isomer propionic aldehyde |
| CN113219025A (en) * | 2021-05-07 | 2021-08-06 | 安徽大学 | Method for quantitatively detecting potassium bromate |
| CN113219025B (en) * | 2021-05-07 | 2023-07-25 | 安徽大学 | Method for quantitatively detecting potassium bromate |
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