CN112816572A - Method for determining content of phenoxyacetic acid in phenoxyacetic acid tested sample - Google Patents

Method for determining content of phenoxyacetic acid in phenoxyacetic acid tested sample Download PDF

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CN112816572A
CN112816572A CN202011576807.1A CN202011576807A CN112816572A CN 112816572 A CN112816572 A CN 112816572A CN 202011576807 A CN202011576807 A CN 202011576807A CN 112816572 A CN112816572 A CN 112816572A
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phenoxyacetic acid
sample
solution
content
mobile phase
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张军立
段志钢
马金玉
刘倩
王新辉
穆军明
崔克娇
赵彬
杨婷
程璐英
曹欢
翟梦
师书迪
刘磊
赵汝梅
宋斌
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NORTH CHINA PHARMACEUTICAL CORP
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Abstract

The invention discloses a method for measuring the content of phenoxyacetic acid in a phenoxyacetic acid measured sample, which belongs to the field of chemical analysis and adopts a high performance liquid chromatography to measure the content of phenoxyacetic acid, and comprises the following steps: (a) preparing a reference substance solution; (b) preparing a sample solution to be detected; (c) chromatographic conditions are as follows: octadecylsilane chemically bonded silica is used as a filler, and the weight ratio of phosphate with the pH value of 3.5: weighing 68g of potassium dihydrogen phosphate, adding purified water to 1000ml, and adjusting the pH value to 3.5 by using phosphoric acid, wherein the mobile phase comprises the following components: water: methanol: ph3.5 phosphate 100:80:20, wavelength: 220nm, flow rate: 1.4. (d) the determination method comprises the following steps: respectively and precisely measuring 10 mu L of each of the measured sample solution and the reference solution, injecting into a liquid chromatograph, recording chromatograms of the measured sample and the reference solution, and calculating according to the peak area by an external standard method to obtain the content of the measured phenoxyacetic acid sample. The method has the advantages of simple and convenient operation process, high accuracy and good stability, and can effectively influence the titration method on the measurement result.

Description

Method for determining content of phenoxyacetic acid in phenoxyacetic acid tested sample
Technical Field
The invention relates to a method for determining effective components in antibiotic raw materials, in particular to a method for determining the content of phenoxyacetic acid in a phenoxyacetic acid sample, and belongs to the field of chemical analysis.
Background
Phenoxyacetic acid, white needle crystals. 1g of product was dissolved in about 75ml of water and readily soluble in ethanol, diethyl ether, benzene, carbon disulfide and glacial acetic acid. Melting point 98 ℃. Boiling point 285 ℃ (partial decomposition) for penicillin V potassium feedstock, its structural formula is as follows:
Figure RE-GDA0002966764740000011
at present, the method for detecting the content of phenoxyacetic acid in domestic enterprises is a titration method, but the method is complex to operate and has poor accuracy.
The prior literature (Chinese medicine, 2004, 13(5), 38) has reported that the content of phenoxyacetic acid in penicillin V potassium is determined by high performance liquid chromatography, a Hypersil ODS2 chromatographic column is adopted, 0.025mol/L ammonium dihydrogen phosphate solution (ammonia solution is used for adjusting the pH value to 7.0-acetonitrile (85:15) is used as a mobile phase, and the detection wavelength is 220nm502730mg/kg (oral rat); 1250mg/kg (rabbit percutaneous).
Therefore, there is a need for improvement of the prior art phenoxyacetic acid detection methods to improve accuracy and reduce solvent toxicity.
Disclosure of Invention
In view of the above, the invention provides a method for determining the content of phenoxyacetic acid in a phenoxyacetic acid detected sample, so as to solve the problems of high reagent toxicity, high possibility of being influenced by impurities and poor accuracy in the existing method.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for measuring the content of phenoxyacetic acid in a phenoxyacetic acid measured sample adopts a high performance liquid chromatography to measure the content of phenoxyacetic acid in the phenoxyacetic acid measured sample, and specifically comprises the following steps:
(a) preparation of control solutions: weighing a phenoxyacetic acid standard substance, adding the phenoxyacetic acid standard substance into a mobile phase for dissolving, quantitatively diluting to obtain a phenoxyacetic acid standard reference substance solution with the concentration of 0.02-0.5 mg/mL, preferably 0.2mg/mL, and shaking uniformly for later use;
(b) preparation of a sample solution to be tested: weighing a phenoxyacetic acid sample to be detected, adding the phenoxyacetic acid sample to a mobile phase for dissolving, and quantitatively diluting to prepare a phenoxyacetic acid sample solution with the concentration of 0.02-0.5 mg/mL, preferably 0.2mg/mL, and shaking uniformly for later use;
(c) chromatographic conditions are as follows: by C18A chromatographic column, octadecylsilane chemically bonded silica is used as a filler, and the flow rate of a mobile phase is 1.2-1.6 mL/min, preferably 1.4 mL/min;
the detection wavelength is 200-230 nm, preferably 220 nm;
the column temperature is 20-30 ℃, and the preferred temperature is 25 ℃;
the theoretical plate number is not less than 2000 calculated according to the main peak;
(d) and (3) determination: respectively measuring 10 mu L of each of a phenoxyacetic acid standard reference substance solution and a phenoxyacetic acid detected sample solution, injecting the phenoxyacetic acid standard reference substance solution and the phenoxyacetic acid detected sample solution into a high performance liquid chromatograph, recording chromatograms of the phenoxyacetic acid standard reference substance solution and the phenoxyacetic acid detected sample solution, and calculating according to an external standard method by peak area to obtain the content of phenoxyacetic acid in the detected sample.
Wherein, the mobile phase is water by volume ratio: methanol: the phosphate aqueous solution is a mixed solution of 100: 70-90: 10-30, and preferably, the mobile phase is a mixed solution of water: methanol: the ratio of phosphate aqueous solution is 100:80: 20.
Further, the pH of the phosphate aqueous solution is 3.5, and the preparation method thereof is: 68g of potassium dihydrogen phosphate were weighed out and added to 1000ml of purified water, and the pH was adjusted to 3.5 with phosphoric acid.
Further, calculating the content of the phenoxyacetic acid in the detected sample by peak area according to an external standard method according to the following formula:
C％＝Aa/As×Cs/Ca×100％，
wherein C% is the content of phenoxyacetic acid in the detected sample, Aa is the liquid phase main peak area of phenoxyacetic acid in the detected sample, As is the liquid phase main peak area of phenoxyacetic acid standard substance, Ca is the concentration of the detected sample, and Cs is the concentration of phenoxyacetic acid standard substance.
The invention has the beneficial effects that the toxicity of the reagent in the operating process of the high performance liquid chromatography analysis method of phenoxyacetic acid provided by the invention is relatively low (methanol LD)505628mg/kg (oral in rat); 15800mg/kg (rabbit skin)), simple and convenient, good precision, high accuracy, good stability, excellent durability, and can effectively avoid the influence of impurities on the measurement result; the method has low requirement on equipment, simple and easily obtained mobile phase medium and strong feasibility and applicability.
Drawings
FIG. 1 is a chromatogram of a phenoxyacetic acid standard of example 2 according to the invention;
FIG. 2 is a chromatogram of a sample of phenoxyacetic acid of example 2 according to the invention;
FIG. 3 is a standard curve diagram of the linear test for determining the content of phenoxyacetic acid in example 25 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the following examples, the invention was tested using the following instruments and reagents:
agilent high performance liquid chromatography (agilent 1200Series detector, agilent 1200Series pump);
sample and reagent: methanol (chromatographic purity), a phenoxyacetic acid standard (an alatin reagent, content 99%), a phenoxyacetic acid sample (North China pharmaceutical Co., Ltd., batch number: 201901101, 001 batch produced in 11 months of 2019).
The method for determining the content of the phenoxyacetic acid in the phenoxyacetic acid detected sample by adopting the high performance liquid chromatography comprises the following steps:
(a) preparation of control solutions: precisely weighing phenoxyacetic acid standard substance, dissolving in mobile phase, and quantitatively diluting to obtain concentrated solutionDegree of Ca1(0.02-0.5 mg/mL) of phenoxyacetic acid standard reference solution, shaking up and fixing the volume;
(b) preparation of a sample solution to be tested: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a phenoxyacetic acid sample solution with the concentration of Ca (0.02-0.5 mg/mL), shaking up, and fixing the volume;
(c) chromatographic conditions are as follows: octadecylsilane chemically bonded silica is used as a filling agent, and the volume ratio of the filler to the octadecylsilane chemically bonded silica is 100: a mixed solution of water, methanol and a phosphate water solution with the pH value of 3.5 in a ratio of 80:20 is used as a mobile phase, and the flow rate is 1.4 mL/min; the detection wavelength is 220 nm; the column temperature was 25 ℃; the theoretical plate number is not lower than 2000 calculated according to the main peak;
(d) the determination method comprises the following steps:
according to Chinese pharmacopoeia (2015 edition), weighing a proper amount of phenoxyacetic acid standard, precisely weighing, and adding the mixture according to a volume ratio of 100: dissolving the mixed solution of water, methanol and phosphate water solution with pH of 3.5 at a ratio of 80:20, and diluting to obtain Ca with a certain concentration1Shaking the solution, precisely measuring 10 mu L of the solution, injecting the solution into a liquid chromatograph, and recording a chromatogram;
taking a proper amount of test samples, precisely weighing, measuring by the same method, and recording a chromatogram;
according to an external standard method, calculating the peak area to obtain the content C% of the phenoxyacetic acid in the detected sample:
C％＝Aa/As×Cs/Ca×100％；
aa is the liquid phase main peak area of phenoxyacetic acid in the detected sample; as is the liquid phase main peak area of the phenoxyacetic acid standard product; ca is the concentration of the sample to be detected; cs is the concentration of the phenoxyacetic acid standard substance.
Example 1
Chromatographic conditions are as follows: using elette C18The reversed phase column is 4.6mm multiplied by 150mm and 5 mu m; the mobile phase is 100 by volume: 80:20 of water, methanol and a phosphate water solution with the pH value of 3.5; the flow rates are respectively 1.0mL/min, 1.4mL/min and 2.0 mL/min; an ultraviolet detector with detection wavelength of 292 nm; the column temperature was 25 ℃ (room temperature); the theoretical plate number is not lower than 2000 calculated by main peak.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain 0.02mg phenoxyacetic acid standard substance solution per 1mL, shaking, and fixing volume;
the determination method comprises the following steps: respectively precisely measuring 10 μ L of the measured sample solution and phenoxyacetic acid standard solution, and injecting into a liquid chromatograph; and recording chromatograms of the reference substance and the detected sample, and calculating according to the peak area by an external standard method to obtain the determination result of the content of the phenoxyacetic acid in the sample.
The content of the phenoxyacetic acid is calculated by adopting the following steps:
correction factor
Figure RE-GDA0002966764740000051
Wherein, W1 is the sample weight (mg) of the reference substance; d1 is control dilution volume (mL); a1 is the peak area of the main peak in the chromatogram of the control solution.
Content of test sample
Figure RE-GDA0002966764740000052
Wherein, W2 is the sample weighing (mg) of the sample; d2 is the dilution volume (mL) of the test article; a2 is the peak area of the main peak of the test article.
The contents of phenoxyacetic acid in the sample obtained by adopting the method are 93.5%, 90.7% and 94.2%.
Example 2
The chromatographic conditions were the same as in example 1.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the determination method and the steps for calculating the content of the phenoxyacetic acid are the same as those in the example 1, chromatograms of the phenoxyacetic acid standard substance and the phenoxyacetic acid sample are shown in figures 1-2, and the calculated content of the phenoxyacetic acid in the sample is respectively 96.7%, 98.2% and 96.8%.
Example 3
The chromatographic conditions were the same as in example 1.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5mg per 1mL, shaking, and fixing volume;
the assay and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the samples was calculated to be 93.5%, 93.7%, and 92.9%, respectively.
Example 4
Chromatographic conditions were similar to example 1, except that the mobile phase used was a mixture of 100: 90: 10 of water, methanol and an aqueous solution of phosphate at pH 3.5.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase pyran for dissolution, quantitatively diluting to prepare a solution containing 0.02mg phenoxyacetic acid standard substance in each 1mL, shaking up, and fixing the volume;
the assay and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the samples was calculated to be 96.6%, 96.8%, and 96.5%, respectively.
Example 5
The chromatographic conditions were the same as in example 4.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the assay and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the samples was calculated to be 96.1%, 95.9%, and 95.7%, respectively.
Example 6
The chromatographic conditions were the same as in example 4.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.7%, 95.5%, and 95.8%, respectively.
Example 7
The chromatographic conditions were the same as in example 1 except for the mobile phase. The volume ratio of the adopted mobile phase is 100: 70: 30 of mobile phase mixed solution.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.02mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.9%, 95.2%, and 95.7%, respectively.
Example 8
The chromatographic conditions were the same as in example 7.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.9%, 95.5%, and 95.6%, respectively.
Example 9
The chromatographic conditions were the same as in example 7.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.7%, 95.4%, and 95.8%, respectively.
Example 10
The chromatographic conditions were the same as in example 1 except for the mobile phase. The volume ratio of the adopted mobile phase is 100: 70: 20 of mobile phase mixed solution.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.02mg per 1mL, shaking, and fixing volume;
the measurement method and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 95.6%, 95.9%, and 95.8%, respectively.
Example 11
The chromatographic conditions were the same as in example 10.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the measurement method and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 95.9%, 95.7%, and 95.6%, respectively.
Example 12
The chromatographic conditions were the same as in example 10.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5g per 1mL, shaking, and fixing volume;
the measurement method and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 95.7%, 97.9%, and 95.3%, respectively.
Example 13
The chromatographic conditions were the same as in example 1 except for the mobile phase. The volume ratio of the adopted mobile phase is 100: 70: 10 the solution is mixed.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.02mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.9%, 95.5%, and 95.6%, respectively.
Example 14
The chromatographic conditions were the same as in example 13.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.3%, 94.7%, and 95.2%, respectively.
Example 15
The chromatographic conditions were the same as in example 13.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5mg per 1mL, shaking, and fixing volume;
the assay and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the samples was calculated to be 95.3%, 96.1%, and 95.8%, respectively.
Example 16
The chromatographic conditions were the same as in example 1 except for the mobile phase. The volume ratio of the adopted mobile phase is 100:80: 10 of mobile phase mixed solution.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the measurement method and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 95.3%, 95.6%, and 95.9%, respectively.
Example 17
The chromatographic conditions were the same as in example 16.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.7%, 94.5%, and 93.9%, respectively.
Example 18
The chromatographic conditions were the same as in example 16.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.7%, 94.6%, and 94.5%, respectively.
Example 19
The chromatographic conditions were the same as in example 1 except for the mobile phase. The volume ratio of the adopted mobile phase is 100:80: 30 of mobile phase mixed solution.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.02mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.02mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.6%, 94.7%, and 93.9%, respectively.
Example 20
The chromatographic conditions were the same as in example 19.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.2mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.2mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.5%, 94.8%, and 94.7%, respectively.
Example 21
The chromatographic conditions were the same as in example 19.
The measured sample solution: precisely weighing a phenoxyacetic acid sample, adding a mobile phase for dissolving, quantitatively diluting to prepare a solution containing 0.5mg of phenoxyacetic acid sample in every 1mL, shaking up, and fixing the volume;
control solution: precisely weighing phenoxyacetic acid standard substance, adding mobile phase for dissolving, quantitatively diluting to obtain solution containing phenoxyacetic acid standard substance 0.5mg per 1mL, shaking, and fixing volume;
the measurement and the procedure for calculating the phenoxyacetic acid content were the same as in example 1, and the phenoxyacetic acid content of the sample was calculated to be 94.8%, 94.6%, and 93.7%, respectively.
From the above examples, it can be seen that: example 2 is a preferred protocol for analyzing the content of phenoxyacetic acid.
The following methodological validation was performed for the method of example 2:
EXAMPLE 22 suitability test for System
Preparing reference substance solution and test solution according to the method of the specific embodiment, measuring according to the same chromatographic conditions as the previous method, and injecting 10 μ L of phenoxyacetic acid standard solution into a liquid chromatograph; measuring 5 times by the same method, and recording chromatogram of the control. The results of the experiment are shown in table 1.
TABLE 1 test results of the applicability of the phenoxyacetic acid content determination system
Figure RE-GDA0002966764740000121
As can be seen from Table 1, the relative standard deviation RSD calculated for 5 times according to the peak area of the sample is 0.015 percent, which accords with that the RSD is less than or equal to 1.0 percent; calculated according to the main peak, the theoretical plate number is 6987, which meets the requirement of not less than 2000. The test result shows that the system precision of the method is good.
EXAMPLE 23 method precision test
6 parts of test solution is prepared according to the method of example 1, the same chromatographic conditions are adopted, the sample injection measurement is carried out according to the measurement method of example 1, the atlas is recorded, and the phenoxyacetic acid content of each test solution is calculated according to the external standard method, and the result is shown in table 2.
TABLE 2 measurement of Phenoxyacetic acid content method precision test results
Figure RE-GDA0002966764740000131
RSD was calculated to be 0.50% for 6 data, less than the limit of 1.0%. The test result shows that the method has good precision.
Example 24 intermediate precision test
6 parts of test solution were prepared according to the method of example 1, and tested by different analysts on different dates and under different instrument conditions according to the measurement method of example 1, chromatograms were recorded, and 3 sets of data were collected for analysis, the relative standard deviation of the results was calculated, the results are shown in Table 3, and the data in the intermediate precision test were compared with the six data in the method precision test.
TABLE 3 measurement of Phenoxyacetic acid content intermediate precision test results
Figure RE-GDA0002966764740000132
Figure RE-GDA0002966764740000141
RSD was calculated to be 0.21% for 6 data, less than the limit of 1.0%. The 6 data in intermediate precision were compared to the 6 data in method precision and the RSD of the 12 data was calculated to be 0.67%, less than the limit of 1.0%. The test result shows that the method has good intermediate precision.
Example 25 examination of the Linear relationship
Control solutions and test solutions were prepared according to the method of example 1 and measured according to the same chromatographic conditions as in example 1: injecting 10 μ L of phenoxyacetic acid standard solution into a liquid chromatograph; measuring 5 times by the same method, and recording chromatogram of the reference substance as a system practicability experiment.
Respectively taking a phenoxyacetic acid reference substance 24mg, placing the phenoxyacetic acid reference substance in a 100mL volumetric flask, adding a mobile phase solution to dilute the phenoxyacetic acid reference substance into a stock solution with the phenoxyacetic acid concentration of 0.24mg/mL, precisely measuring 3mL, 4mL, 5mL, 6mL and 7mL of the reference stock solution, placing the reference stock solution in a 10mL volumetric flask, diluting the solution to a scale by using the mobile phase, shaking the solution uniformly to prepare solutions (corresponding to 60%, 80%, 100%, 120% and 140% of a test solution) containing phenoxyacetic acid of 0.072mg, 0.096mg, 0.12mg, 0.144mg and 0.168mg in each 1mL of the solution, taking 10 mu L of the solutions as linear solutions, respectively injecting the linear solutions into a liquid chromatograph, respectively recording chromatograms, taking the concentration as a horizontal coordinate and the peak area as a vertical coordinate, drawing a standard curve, wherein the corresponding data is shown in a table 3, and the calculated regression equation is 5038 x-1.88; the correlation coefficient R is 0.9990, and meets the requirement that the correlation coefficient R of the components to be tested in the linear range test is more than or equal to 0.999. The test result shows that: the phenoxyacetic acid has a good linear relation between the peak area and the concentration within the concentration range of 0.072-0.168 mg/mL.
TABLE 4 Linear test results for phenoxyacetic acid assay
Figure RE-GDA0002966764740000142
Figure RE-GDA0002966764740000151
Example 26 accuracy test
Control solutions and test solutions were prepared according to the method of example 1 and measured according to the same chromatographic conditions as in example 1: respectively injecting 10 μ L of phenoxyacetic acid standard solution into a liquid chromatograph; measuring 5 times by the same method, and recording chromatogram of the reference substance as a system practicability experiment.
Weighing 3 parts of phenoxyacetic acid reference substances, namely 9.6mg, 12mg and 14.4mg respectively, placing the phenoxyacetic acid reference substances into 50mL volumetric flasks respectively, adding a mobile phase for dissolving and diluting to a scale, and shaking up to be respectively equal to 80%, 100% and 120% of the concentration of the test sample. And respectively injecting 10 mu L of the mixture into a liquid chromatograph, respectively recording chromatograms, calculating by peak area according to an external standard method, and taking the ratio of the content to a theoretical value as a recovery rate, wherein the result is shown in table 5.
TABLE 5 Phenoxyacetic acid content determination accuracy test results
Figure RE-GDA0002966764740000152
The test result shows that: the concentration of the sample is in the range of 80-120%, the recovery rate after 9 times is in the range of 98-102%, the RSD value is 0.05%, and is less than the limit of 2.0%, and the RSD meets the standard regulation.
EXAMPLE 27 stability of the solution
1. Stability at room temperature
Precisely weighing about 12mg of phenoxyacetic acid sample, placing the phenoxyacetic acid sample in a 50mL volumetric flask, adding the mobile phase for dissolving, diluting to a scale, and shaking up. The solution was left at room temperature for 0, 2, 4, 6, 8, 10, and 12 hours, and the stability of the solution was examined by the measurement method of example 1.
Stability at 2.4 deg.C
Precisely weighing about 12mg of phenoxyacetic acid sample, placing the phenoxyacetic acid sample in a 50mL volumetric flask, adding the mobile phase for dissolving, diluting to a scale, and shaking up. The test was performed by the measurement method of example 1 after leaving at 4 ℃ for 0, 2, 4, 6, 8, 10, and 12 hours to examine the stability of the solution.
The results of the stability tests of the test solutions at room temperature and 4 ℃ are shown in Table 6.
TABLE 6 Phenoxyacetic acid content solution stability Studies
Figure RE-GDA0002966764740000161
As can be seen from Table 6, the RSD values of the test solutions were less than the limit of 2.0% for 7 data at room temperature and 4 deg.C, respectively. The test result shows that the sample content of the solution is stable within 12 hours under the conditions of room temperature and 4 ℃.
EXAMPLE 28 durability examination
The durability of the analysis method was examined by varying the flow rate, the column temperature, the detection wavelength, and the different types of chromatography columns.
1. Replacement of chromatographic columns
The sample test samples are detected by replacing chromatographic columns and respectively adopting C18 chromatographic columns with different models of large continuous eletrin, Agilent and large continuous eletrin, and the experimental results are shown in a table 7-1.
TABLE 7-1 sample assay HPLC method durability (different model chromatographic columns)
Figure RE-GDA0002966764740000171
Test results show that the separation degree of the sample and adjacent peaks is larger than 1.5, the system applicability meets the specification, and the RSD value of 6 data is smaller than 2.0%. Therefore, the chromatographic columns of different types do not influence the determination of the content of the sample.
2. Changing the detection wavelength
The sample samples were tested by adjusting the detection wavelength to range (292 + -5 nm) with 287nm, 292nm and 297nm, respectively, and the results are shown in tables 7-3.
TABLE 7-2 sample assay durability of HPLC methods (different detection wavelengths)
Figure RE-GDA0002966764740000181
Test results show that the separation degree of the sample and adjacent peaks is larger than 1.5, the system applicability meets the regulation, and the RSD value of 6 data is smaller than 2.0%. Therefore, different detection wavelengths do not influence the determination of the content of the sample.
3. Changing the column temperature
The column temperature was varied between (25. + -. 5 ℃ C.) and the column temperature was used to detect the sample samples at 20 ℃ C., 25 ℃ C., 30 ℃ C. respectively, and the results are shown in tables 7-3.
TABLE 7-3 sample assay HPLC method durability (different column temperatures)
Figure RE-GDA0002966764740000182
Test results show that the separation degree of the sample and adjacent peaks is larger than 1.5, the system applicability meets the specification, and the RSD value of 6 data is smaller than 2.0%. From this, it was found that a slight change in the column temperature did not affect the measurement of the sample content.
4. Varying the flow rate
The sample test samples were tested by varying the flow rates between (1.2. + -. 0.2mL/min) using flow rates of 1.0mL/min, 1.2mL/min, 1.4mL/min, respectively, and the results are shown in tables 7-5.
TABLE 7-4 sample assay HPLC method durability (different flow rates)
Figure RE-GDA0002966764740000191
Test results show that the separation degrees of the sample and adjacent peaks are all larger, the system applicability meets the regulations, and the RSD value of 6 data is smaller. It is thus clear that a slight change in flow rate does not affect the measurement of the sample content.
Example 29 specificity test
Respectively carrying out destructive tests on the sample under the conditions of high temperature, illumination, acid, alkali and oxidation, and inspecting the purity of a main peak and the separation degree of the main peak and an adjacent peak of the destroyed sample; and taking a blank solvent or the damaged blank solvent for sample injection, and inspecting whether the blank solvent interferes with the determination of the content of the sample.
1. Destructive test
And (3) no damage: 10.34mg of sample is taken and placed in a 50mL volumetric flask, the mobile phase is added for dissolution to the scale, the mixture is shaken evenly, the sample introduction detection is carried out, and the chromatogram is recorded.
a. Alkali breakdown test
Weighing 10.45mg of a test sample, placing the test sample in a 50mL volumetric flask, adding 20mL of mobile phase, adding 1mL of 1mol/mL of sodium hydroxide, placing for 1min, adding 1mL of 1mol/mL of hydrochloric acid solution for neutralization, adding the mobile phase for dissolving and diluting to a scale, shaking uniformly, carrying out sample injection detection, and recording a chromatogram.
b. Acid breakdown test
Weighing 10.78mg of a test sample, placing the test sample in a 50mL volumetric flask, adding 20mL of mobile phase, adding 1mL of 1mol/mL hydrochloric acid solution, placing for 1min, adding 1mL of 1mol/mL sodium hydroxide for neutralization, adding the mobile phase for dissolving and diluting to a scale, shaking uniformly, carrying out sample injection detection, and recording a chromatogram.
c. High temperature failure test
Weighing 10.29mg of test sample, placing in a 50mL volumetric flask, adding 3/4 dissolved and diluted by the mobile phase to approximate volume of the volumetric flask, carrying out water bath at 80 ℃ for 30min, cooling to room temperature, adding the mobile phase for dissolution and dilution to scale, shaking uniformly, carrying out sample injection detection, and recording a chromatogram.
d. Oxidative destruction test
Weighing 10.64mg of test sample, placing in a 50mL volumetric flask, adding 20mL of mobile phase, adding 1mL of 30% hydrogen peroxide, placing for 1min, adding the mobile phase for dissolving and diluting to scale, shaking uniformly, detecting by sample injection, and recording chromatogram.
e. Light damage test
Taking 10.38mg of the product, placing the product in a 50mL volumetric flask, adding a mobile phase for dissolving to a scale, placing the solution in a 4500lx illumination test box for 24 hours, taking out, shaking uniformly, carrying out sample injection detection, and recording a chromatogram.
The results of the content measurement of the above samples subjected to the non-destructive, alkali destructive, acid destructive, high temperature destructive, oxidation destructive, and light destructive tests are shown in Table 8.
TABLE 8 sample assay specificity damage results
Figure RE-GDA0002966764740000201
Note: the main peak area is converted from the peak area measured by an undamaged peak area sample according to the sample weighing and is a theoretical value; the destruction degree is the percentage of the area of the main peak after destruction to the area of the main peak before destruction; and R is the separation degree of the main peak area and the impurity peak of the front adjacent peak.
Test results show that all the damage degrees reach 80-90%, and the main peak area and the impurity peak separation degree of the front adjacent peak are all larger than the specified value. From this, it was found that the main peak was a single peak, and the content of the sample was not affected by the degradation impurities generated under each destruction condition.

Claims (8)

1. A method for measuring the content of phenoxyacetic acid in a phenoxyacetic acid sample is characterized by comprising the following steps:
(a) preparation of control solutions: weighing a phenoxyacetic acid standard substance, adding the phenoxyacetic acid standard substance into a mobile phase for dissolving, quantitatively diluting to obtain a phenoxyacetic acid standard reference substance solution with the concentration of 0.02-0.5 mg/mL, and shaking uniformly for later use;
(b) preparation of a sample solution to be tested: weighing a phenoxyacetic acid sample to be detected, adding the phenoxyacetic acid sample to a mobile phase for dissolving, and quantitatively diluting to prepare a phenoxyacetic acid sample solution with the concentration of 0.02-0.5 mg/mL, and shaking uniformly for later use;
(c) chromatographic conditions are as follows: by C18Chromatographic column, octadecylsilane chemically bonded silica as filler, flowingThe flow rate of the phase is 1.2-1.6 mL/min, the detection wavelength is 200-230 nm, the column temperature is 20-30 ℃, and the theoretical plate number is not less than 2000 calculated according to the main peak;
(d) and (3) determination: respectively measuring 10 mu L of each of a phenoxyacetic acid standard reference substance solution and a phenoxyacetic acid detected sample solution, injecting the phenoxyacetic acid standard reference substance solution and the phenoxyacetic acid detected sample solution into a high performance liquid chromatograph, recording chromatograms of the phenoxyacetic acid standard reference substance solution and the phenoxyacetic acid detected sample solution, and calculating according to an external standard method by peak area to obtain the content of phenoxyacetic acid in a detected sample;
the mobile phase is water in volume ratio: methanol: the phosphate aqueous solution is a mixed solution of 100: 70-90: 10-30.
2. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1, wherein the mobile phase comprises water: methanol: the ratio of phosphate aqueous solution is 100:80: 20.
3. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1 or 2, wherein the pH value of the phosphate aqueous solution is 3.5.
4. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1, wherein the concentration of the phenoxyacetic acid standard control solution in (a) and/or the phenoxyacetic acid test sample solution in (b) is 0.2 mg/mL.
5. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1, wherein the flow rate of the mobile phase in (c) is 1.4 mL/min.
6. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1, wherein the detection wavelength in (c) is 220 nm.
7. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1, wherein the column temperature in (c) is 25 ℃.
8. The method for determining the content of phenoxyacetic acid in a phenoxyacetic acid test sample according to claim 1, wherein the calculation of the content of phenoxyacetic acid in the test sample by peak area according to the external standard method in (d) is as follows:
C％＝Aa/As×Cs/Ca×100％，
wherein C% is the content of phenoxyacetic acid in the detected sample, Aa is the liquid phase main peak area of phenoxyacetic acid in the detected sample, As is the liquid phase main peak area of phenoxyacetic acid standard substance, Ca is the concentration of the detected sample, and Cs is the concentration of phenoxyacetic acid standard substance.
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