CN107632076A - The quick instrument analytical method of azanol residual quantity in a kind of reaction solution - Google Patents
The quick instrument analytical method of azanol residual quantity in a kind of reaction solution Download PDFInfo
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- CN107632076A CN107632076A CN201710682553.3A CN201710682553A CN107632076A CN 107632076 A CN107632076 A CN 107632076A CN 201710682553 A CN201710682553 A CN 201710682553A CN 107632076 A CN107632076 A CN 107632076A
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Abstract
The invention discloses the quick instrument analytical method of azanol residual quantity, this method in a kind of reaction solution to specifically include following steps：Step 1：Derivatization reaction is occurred into for the reaction solution containing azanol and benzaldehyde, generates benzaldoxime；Step 2：Using high effective liquid chromatography for measuring, it derives the content of benzaldoxime in liquid, according to the content of benzaldoxime and then calculates the content of azanol in former reaction solution.Analyzing detecting method provided by the invention is simple to operate, and the degree of accuracy is high, and specificity is strong, and high sensitivity, analyze speed is fast, efficiency high.Compared with prior art, this method is after derivative reaction with liquid chromatograph by being measured, can accurate qualitative, quantitative, meet the needs in research and production.
Description
Technical field
The invention belongs to chemical analysis technical field, it is related to a kind of quick Instrumental Analysis side of azanol residual quantity in reaction solution
Method, benzaldoxime is generated by benzaldehyde and azanol reaction more particularly to one kind, is measured with liquid chromatograph, can be accurate
The quick instrument analytical method of hydroxylamine content in qualitative, quantitative reaction solution.
Background technology
Azanol is generally used as reducing agent in organic synthesis, industrially generally dissociates into azanol, Ran Hourang with hydroxylamine hydrochloride
Azanol heating response together with succinic anhydride generates N- hydroxysuccinimides, and the usual hydroxylamine hydrochloride of the reaction is excessive, unreacted
Complete azanol is unstable explosive in reaction solution, therefore to control the residual quantity of azanol in reaction solution.
At present it is known that azanol determination of residual amount method be version in 2015《Chinese Pharmacopoeia》Include, particular content is：In alkali
Property under the conditions of, then diazo-reaction occurs with p-aminobenzene sulfonic acid for azanol and Iod R generation nitrous acid, then even with alpha-naphthylamine
Connection forms coloured azo-compound, and the content of azanol is determined using spectrophotometry instrument.But the above method be
Its absorbance is determined in visible-range, higher is required to color sample, and reaction solution generally has color, while the azanol determined
Concentration is very low, therefore uses the azanol residual quantity error in this method measure reaction solution big, inaccurate, can not meet the inspection of safety in production
Survey and require.Therefore a kind of quick, accurate, convenient and economic detection method need to be established, is advantageous to monitor the azanol in reaction solution
Content, so as to ensure production safety.
Application publication number CN102937577A discloses micro hydroxyl in a kind of ABTS free radicals Fading spectrophotometry detection water
The method of amine, the technology for detection amount are less, it is impossible to meet the testing requirements of production.
The content of the invention
, can be full it is an object of the invention to provide a kind of method that step is simple while can accurately detect azanol residual quantity
The sufficient degree of accuracy is high, and detection limit is low, and can detect the demand of azanol residual quantity simultaneously.
The purpose of the present invention can be achieved through the following technical solutions：
Azanol residual quantity instrument analytical method, this method specifically include following steps in a kind of reaction solution：
Step 1：Derivatization reaction is occurred into for the reaction solution containing azanol and benzaldehyde, generates benzaldoxime；
Step 2：Using high effective liquid chromatography for measuring, it derives the content of benzaldoxime in liquid, according to containing for benzaldoxime
Measure and then calculate the content of azanol in former reaction solution.
Further, step 1 concrete operations are：Azanol reaction liquid is weighed in volumetric flask, adds benzaldehyde, solubilization
Agent, it is placed in stirring in constant temperature blender with magnetic force and derivatization reaction occurs.
Further, after the derivatization reaction occurs, in addition to the operation of following constant volumes：Weigh a certain amount of derivatization reaction solution
In the volumetric flask equipped with acetonitrile, add 60% acetonitrile solution (acetonitrile：Water=60:40, V/V) scale is diluted to, mixes, treats liquid
Analysis of hplc.
Further, in the reaction solution material of azanol (azanol amount is estimated value in former reaction solution) and benzaldehyde amount
The ratio between be 2-5.
Further, the solvent is at least one of ethanol, methanol, acetonitrile, purified water.
Further, the ratio between the mass number of the solvent and the mass number containing azanol reaction liquid are 15-10.
Further, the derivatization reaction temperature is 20-35 DEG C, reaction time 0.5-1h.
Further, the liquid chromatographic detection is：The derivatization reaction liquid of constant volume is detected using liquid chromatograph, liquid phase
Chromatographic condition：Chromatographic column：Diamonsil C18 5um, 250*4.6mm；Column temperature：30℃；Mobile phase：70% acetonitrile solution
(acetonitrile：Water=70:30, V/V)；Detection wavelength：250nm；Flow velocity：1.0ml/min；Sample size：20ul；Isocratic operation, operation
Time 10min.
Further, the specific calculating process of the content of the azanol is as follows：
The content W of oxime in derivative reactionOxime%=ASample*CMark*F/AMark/CSample* 100%
ASample：The peak area of benzaldoxime in sample solution
CSample：The concentration of sample solution
AMark：The peak area of benzaldoxime in standard solution
CMark：The concentration of benzaldoxime standard solution
F：The content of standard items benzaldoxime
The amount %=W of azanolOxime%*m0/121*33/MSample* 100%
m0：Participate in derivatization reaction gross weight/g
MSample：Azanol reaction liquid sample sample weighting amount to be measured
121：The relative molecular mass of benzaldoxime
33：The relative molecular mass of azanol.
Beneficial effects of the present invention：Analyzing detecting method provided by the invention is simple to operate, and the degree of accuracy is high, specificity
By force, high sensitivity, analyze speed is fast, efficiency high.Compared with prior art, this method after derivative reaction by using liquid chromatogram
Instrument is measured, can accurate qualitative, quantitative, meet research and production in needs.
Brief description of the drawings
For the ease of it will be appreciated by those skilled in the art that the present invention is further illustrated below in conjunction with the accompanying drawings.
Fig. 1 is standard liquid chromatogram of the present invention.
Embodiment
Technical scheme is clearly and completely described below in conjunction with embodiment, it is clear that described reality
It is only part of the embodiment of the present invention to apply example, rather than whole embodiments.It is general based on the embodiment in the present invention, this area
All other embodiment that logical technical staff is obtained under the premise of creative work is not made, belong to what the present invention protected
Scope.
Instrument and reagent
Liquid chromatograph：1525Waters；
Constant temperature blender with magnetic force：90-1 types；Shanghai Hu Xi Analytical Instrument Co., Ltd
Ultrasonic washing instrument：KQ-250B；Kunshan ultrasonic instrument Co., Ltd
BenzaldoximeStandard liquid：Oneself configuration；
Acetonitrile (chromatographic grade), absolute ethyl alcohol (analysis level)；
Sample pre-treatments
Weigh azanol (NH2OH) reaction solution 1.5g adds 0.54g benzaldehydes in 25ml volumetric flasks
Add 12g absolute ethyl alcohols, add 3.8g purified waters, be placed in stirring reaction 1h in constant temperature blender with magnetic force.Then it is above-mentioned molten to weigh 60mg
Liquid adds 60% acetonitrile solution (acetonitrile in the 25ml volumetric flasks equipped with 5ml acetonitriles：Water=60:40, V/V) scale is diluted to,
Mix.Treat liquid-phase chromatographic analysis.
Liquid phase chromatogram condition：
Chromatographic column：Diamonsil C18 (5um, 250*4.6mm)
Column temperature：30℃
Mobile phase：70% acetonitrile solution (acetonitrile：Water=70:30, V/V)
Detection wavelength：250nm
Flow velocity：1.0ml/min
Sample size：20ul
Isocratic operation, run time 10min.
The linear equation of embodiment 1 and standard items chromatogram
With acetonitrile-water (60:40, V/V) be solvent, configuration benzaldoxime concentration of standard solution is respectively 20,15,10,5,
1st, 0ug/ml series standard solution, sample introduction determines peak area under above-mentioned chromatographic condition, with quantified by external standard method.Standard liquid color
Such as " Fig. 1 ", using peak area y as ordinate, concentration x is that abscissa carries out linear regression to spectrogram, as a result such as " table 1 ".
The retention time of benzaldoxime, linear equation and coefficient correlation in table 1：
| Analyte | Retention time (min) | Linear equation | Coefficient correlation |
| Benzaldoxime | 3.58 | Y=130777*x+14343 | R2=0.9987 |
The derivatization process of embodiment 2 optimizes
2.1 derive the selection of solvent
In experimentation, the selection of derivatization reaction solvent directly affects in derivatization process whether solution is uniform, influences to examine
Whether accurate survey result.In order to obtain measurement result as accurate as possible, we must select that derivatization reaction solution can be allowed equal
Even solvent.By Literature Consult, and specific experimentation in the lab, select ethanol-purified water (12:3.8；g/
G) it is derivatization reaction solvent, finds using this derivative solvent relative to other derivative solvent (such as ethanol-purified waters；50/50；V/
V) derivatization reaction solution can be made uniform, not stratified, is easy to claim sample detection.
2.2 method detection limits and precision
LOD and LOQ is that signal to noise ratio (s/n) is 3 respectively:1 and 10:1 compound concentration.By being used under conditions of HPLC
60% acetonitrile solution (acetonitrile：Purified water=60:40；V/V determined after) diluting benzaldoxime, it is LOD to obtain result：2.6ng/
ml；LOQ：8.6ng/ml, it can be seen that：Benzaldoxime sensitivity fully meets detection demand.
2.3 Precision Experiment
The hydroxylamine solution that mass fraction is 0.5% is added in reaction solution sample, is derived according to 2.1 analyte derivative process
Sample, while 5 samples are handled, as a result see " table 2 ".
The Precision Experiment result of table 2
2.4 rate of recovery are tested
Using the average recovery method measure rate of recovery in experiment.In reaction solution sample, high 15.0g/Kg is separately added into；In
10.0g/Kg；The hydroxylamine solution of low tri- concentration of 5.0g/Kg, each concentration is parallel 3 parts, spreads out according to 2.1 analyte derivative process
Raw sample, calculates the rate of recovery of sample, as a result sees " table 3 ".As a result show to have obtained the preferable rate of recovery, show that the experiment has
The higher rate of recovery.
The rate of recovery experimental result of table 3
The detection of azanol residual quantity in the reaction solution of embodiment 3
This law and version in 2015 is respectively adopted《Chinese Pharmacopoeia》Detect the residual quantity of azanol in reaction solution.
This law：Azanol reaction liquid 1.7325g is weighed in 25ml volumetric flasks, adds 0.9488g benzaldehydes, add 11.6663g without
Water-ethanol, add 1.9885g purified waters, be placed in stirring reaction 1h in constant temperature blender with magnetic force.Then the above-mentioned solution of 114.1mg is weighed
In the 25ml volumetric flasks equipped with 5ml acetonitriles, add 60% acetonitrile solution (acetonitrile：Water=60:40, V/V) scale is diluted to, is mixed
It is even.Treat liquid-phase chromatographic analysis.Testing result：The content of azanol is 1.75% (mass percent) in azanol reaction liquid.
Version in 2015《Chinese Pharmacopoeia》Method：0.5ml azanol reaction liquid is pipetted in 1000ml volumetric flasks, is diluted with water
To scale, mix.The above-mentioned solution of 0.6ml is pipetted again in 10ml volumetric flasks, is diluted with water to scale, is mixed.It is dilute to pipette 0.3ml
Sample solution after releasing adds 6% sodium acetate 1.3ml；Add 1% p-aminobenzene sulfonic acid 0.2ml；Add 1.3% iodine solution
0.1ml, after placing 10min, add 0.4mol/L sodium thiosulfate 50ul；Add 0.6% alpha-naphthylamine solution 40ul；Mix.Room temperature
1h is placed, heart 5min is left through per minute 10000, takes supernatant, at 520nm, treats that UV-VIS spectrophotometry detects.
Testing result：The content of azanol is 5.52% (mass percent) in azanol reaction liquid.
The detection of azanol residual quantity in the reaction solution of embodiment 4
Take azanol reaction liquid 1.5824g to add 0.8772g benzaldehydes in 25ml volumetric flasks, add 11.5332g absolute ethyl alcohols,
Add 1.9418g purified waters, room temperature is placed in stirring reaction 1h in constant temperature blender with magnetic force.Then the above-mentioned solution of 99.6mg is weighed in dress
Have in the 25ml volumetric flasks of 5ml acetonitriles, add 60% acetonitrile solution (acetonitrile：Water=60:40, V/V) scale is diluted to, is mixed.
Treat liquid-phase chromatographic analysis.Testing result：The content of azanol is 1.87% (mass percent) in azanol reaction liquid.
From embodiment 3-4 testing results, the sensitivity of the method for the invention, the rate of recovery are high, and measurement result is accurate
Degree was high, with version in 2015《Chinese Pharmacopoeia》The method included is compared, and this method measurement result is accurate.
Conclusion：The sample result degree of accuracy using this law measure is high, can accurately monitor the content of azanol in reaction solution, full
The requirement produced enough.
Present invention disclosed above preferred embodiment is only intended to help and illustrates the present invention.Preferred embodiment is not detailed
All details are described, it is only described embodiment also not limit the invention.Obviously, according to the content of this specification,
It can make many modifications and variations.This specification is chosen and specifically describes these embodiments, is to preferably explain the present invention
Principle and practical application so that skilled artisan can be best understood by and utilize the present invention.The present invention is only
Limited by claims and its four corner and equivalent.
Claims (9)
1. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution, it is characterised in that this method specifically includes following step
Suddenly：
Step 1：Derivatization reaction is occurred into for the reaction solution containing azanol and benzaldehyde, generates benzaldoxime；
Step 2：Using high effective liquid chromatography for measuring, it derives the content of benzaldoxime in liquid, is entered according to the content of benzaldoxime
And calculate the content of azanol in former reaction solution.
2. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 1, it is characterised in that institute
Stating step 1 concrete operations is：Azanol reaction liquid is weighed in volumetric flask, adds benzaldehyde, solubilizer, is placed in constant temperature blender with magnetic force
Derivatization reaction occurs for upper stirring.
3. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 2, it is characterised in that institute
After stating derivatization reaction generation, in addition to the operation of following constant volumes：A certain amount of derivatization reaction solution is weighed in the volumetric flask equipped with acetonitrile
In, add 60% acetonitrile solution to be diluted to scale, mix, treat liquid-phase chromatographic analysis.
4. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 2, it is characterised in that institute
It is 2-5 to state the ratio between amount of material of azanol and benzaldehyde in reaction solution.
5. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 2, it is characterised in that institute
Solvent is stated as at least one of ethanol, methanol, acetonitrile, purified water.
6. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 2, it is characterised in that institute
It is 15-10 to state the ratio between the mass number of solvent and mass number containing azanol reaction liquid.
7. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 2, it is characterised in that institute
It is 20-35 DEG C to state derivatization reaction temperature, reaction time 0.5-1h.
8. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 3, it is characterised in that institute
Stating liquid chromatographic detection is：The derivatization reaction liquid of constant volume is detected using liquid chromatograph, liquid phase chromatogram condition：Chromatographic column：
Diamonsil C18 5um, 250*4.6mm；Column temperature：30℃；Mobile phase：70% acetonitrile solution；Detection wavelength：250nm；Stream
Speed：1.0ml/min；Sample size：20ul；Isocratic operation, run time 10min.
9. the quick instrument analytical method of azanol residual quantity in a kind of reaction solution according to claim 1, it is characterised in that institute
The specific calculating process of content for stating azanol is as follows：
The content W of oxime in derivative reactionOxime%=ASample*CMark*F/AMark/CSample* 100%
ASample：The peak area of benzaldoxime in sample solution
CSample：The concentration of sample solution
AMark：The peak area of benzaldoxime in standard solution
CMark：The concentration of benzaldoxime standard solution
F：The content of standard items benzaldoxime
The amount %=W of azanolOxime%*m0/121*33/MSample* 100%
m0：Participate in derivatization reaction gross weight/g
MSample：Azanol reaction liquid sample sample weighting amount to be measured
121：The relative molecular mass of benzaldoxime
33：The relative molecular mass of azanol.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109632979A (en) * | 2018-11-12 | 2019-04-16 | 上海大学 | Azanol analysis method when hydroxy amino urea coexists |
| CN111812249A (en) * | 2020-07-24 | 2020-10-23 | 济南同路医药科技发展有限公司 | Detection method of trace hydroxylamine hydrochloride |
| CN111855881A (en) * | 2020-08-24 | 2020-10-30 | 珠海润都制药股份有限公司 | Method for detecting hydroxylamine hydrochloride in azilsartan |
| CN113075343A (en) * | 2020-01-04 | 2021-07-06 | 东莞市东阳光仿制药研发有限公司 | Detection method of hydroxylamine and salt thereof |
| CN114994212A (en) * | 2022-06-21 | 2022-09-02 | 常州合全药业有限公司 | High performance liquid chromatography detection method for hydroxylamine residue in medicine |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109632979A (en) * | 2018-11-12 | 2019-04-16 | 上海大学 | Azanol analysis method when hydroxy amino urea coexists |
| CN109632979B (en) * | 2018-11-12 | 2021-01-12 | 上海大学 | Hydroxylamine analysis method in the coexistence of aminohydroxyurea |
| CN113075343A (en) * | 2020-01-04 | 2021-07-06 | 东莞市东阳光仿制药研发有限公司 | Detection method of hydroxylamine and salt thereof |
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| CN111812249A (en) * | 2020-07-24 | 2020-10-23 | 济南同路医药科技发展有限公司 | Detection method of trace hydroxylamine hydrochloride |
| CN111855881A (en) * | 2020-08-24 | 2020-10-30 | 珠海润都制药股份有限公司 | Method for detecting hydroxylamine hydrochloride in azilsartan |
| CN114994212A (en) * | 2022-06-21 | 2022-09-02 | 常州合全药业有限公司 | High performance liquid chromatography detection method for hydroxylamine residue in medicine |
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