CN106501412B - A method of it is measured by high efficiency liquid phase chromatographic analysis method and prepares o-aminophenol yield using o-nitrophenol - Google Patents
A method of it is measured by high efficiency liquid phase chromatographic analysis method and prepares o-aminophenol yield using o-nitrophenol Download PDFInfo
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Abstract
The present invention relates to the measuring methods of yield.A method of it is measured by high efficiency liquid phase chromatographic analysis method and prepares o-aminophenol yield using o-nitrophenol, being obtained respectively by high efficiency liquid phase chromatographic analysis method using peak area is ordinate concentration as the canonical plotting of the o-nitrophenol of abscissa and o-aminophenol；The high-efficient liquid phase chromatogram that the final sample solution of o-aminophenol is prepared using o-nitrophenol is obtained by high efficiency liquid phase chromatographic analysis method；Obtain the peak area of o-nitrophenol and o-aminophenol respectively from high-efficient liquid phase chromatogram, they are substituted into respectively in step 1 using peak area is ordinate concentration as the canonical plotting of the o-nitrophenol of abscissa and o-aminophenol, obtains the concentration of o-nitrophenol and o-aminophenol respectively.
Description
Technical field
The present invention relates to the measuring methods of yield, utilize more particularly to a kind of measured by high efficiency liquid phase chromatographic analysis method
The method that o-nitrophenol prepares o-aminophenol yield.
Background technique
O-aminophenol is a kind of important chemical intermediate, is widely used in dyestuff, medicine, press and biology neck
Domain.It can be used for preparing sulfur dye, azo dyes and fluorescent whitening agent and plastics solidification agent and medical product.In recent years
People have found that o-aminophenol can be used as the chemical modifying agent of fatty acid for analyzing fatty acid, by o-aminophenol and carbonyl again
Schiff made of based compound and its certain metal complexs catalysis behavior, magnetic property and in terms of also have
Important function.
The preparation of o-aminophenol mainly is restored to obtain by o-nitrophenol, and method mainly has iron powder reducing method, vulcanization
Sodium reduction, electrolytic synthesis and hydrogenating reduction method.Electrolytic synthesis has product pure compared with traditional chemical method, produces
Rate is high, pollutes the advantages that small and obtains the concern of researcher.Its electrosynthesis glyoxal route are as follows:
It is that o-aminophenol is prepared by electroreduction o-nitrophenol.Include neighbour in solution after due to electrolysis
Two kinds of components of amino-phenol and o-nitrophenol need to measure (o-nitrophenol is excessive in preparation process), and disclose at present
Document report it is rarely seen have individually measurement o-aminophenol or o-nitrophenol chromatography.For example, " chromatography ", 2012, (9):
" the 11 kinds of amino-phenols in hplc simultaneous determination hair dye " reported on P870-875；" chemistry notification ",
2011, (12): P1140-1144" the adjacent nitre in microwave-assisted-headspace liquid-phase microextraction efficient liquid phase chromatographic analysis water sample of upper report
Base phenol " etc., not yet discovery can measure the analysis method of both compounds simultaneously.Therefore, establishing one kind can measure simultaneously
The method of o-aminophenol and o-nitrophenol two-component is solved using o-nitrophenol as Material synthesis o-aminophenol process
In, the adjustment and optimization of reaction condition are carried out in time, and it is very necessary for improving reaction efficiency problem.
Summary of the invention
The technical problems to be solved by the present invention are: how in view of the drawbacks of the prior art, proposing a kind of simple and reliable survey
The method of o-aminophenol yield is determined to carry out the adjustment and optimization of reaction condition in time.
The technical scheme adopted by the invention is that: it is a kind of that o-nitrophenol is utilized by high efficiency liquid phase chromatographic analysis method measurement
The method for preparing o-aminophenol yield is carried out according to following step
Step 1: being obtained respectively by high efficiency liquid phase chromatographic analysis method using peak area is ordinate concentration as the neighbour of abscissa
The canonical plotting of nitrophenol and o-aminophenol；
Step 2: obtaining the final samples for preparing o-aminophenol using o-nitrophenol by high efficiency liquid phase chromatographic analysis method
The high-efficient liquid phase chromatogram of product solution；
Step 3: obtaining the peak face of o-nitrophenol and o-aminophenol respectively from the high-efficient liquid phase chromatogram in step 2
Product, they are substituted into respectively in step 1 using peak area is ordinate concentration as the o-nitrophenol of abscissa and o-aminophenol
Canonical plotting, respectively obtain o-nitrophenol and o-aminophenol concentration, yield=(the actual measurement quality of o-aminophenol
Concentration/o-aminophenol Theoretical Mass concentration) * 100%.
As a kind of preferred embodiment: in high efficiency liquid phase chromatographic analysis method, chromatographic column is Shim-pack VP-ODS, detects wave
Grow between 270 ~ 300 nm, mobile phase is methanol: the solution of water=60 ~ 100%, flow rate of mobile phase are 0.4 ~ 1.4 ml/min,
25 ~ 40 DEG C of chromatographic column column temperature range, sample volume are 20 uL.
As a kind of preferred embodiment: in high efficiency liquid phase chromatographic analysis method, Detection wavelength is 285 nm, and mobile phase is 100% first
Alcohol, flow rate of mobile phase are 0.80 ml/min, and chromatographic column column temperature is 35 DEG C.
The beneficial effects of the present invention are: two kinds of compounds in solution coexist to o-aminophenol and o-nitrophenol in the present invention
While measure, can quickly, accurately obtain the yield of o-aminophenol.
Detailed description of the invention
Fig. 1: the high-efficient liquid phase chromatogram of o-aminophenol and o-nitrophenol mixed standard solution.
Fig. 2: the high-efficient liquid phase chromatogram of test solution.
Fig. 3: the canonical plotting of o-aminophenol.
Fig. 4: the canonical plotting of o-nitrophenol.
Specific embodiment
The invention will be further described with reference to embodiments:
The present embodiment instrument and reagent
Japanese Shimadzu Corporation LC-10A type high performance liquid chromatograph is furnished with SHIMADZU SPD-10Avp detector, N-
2000 Data Processing in Chromatography Workstation, CTO-10ASvp post case, SCL-10Avp system controller；SK250HP type ultrasonic cleaner
(Shanghai section leads ultrasonic instrument)；BS-1105 type precision electronic balance (Beijing Sai Duolisi)；FB-01T type solvent filter (day
Saliva is permanent difficult to understand).
Methanol is chromatographically pure (α Cygni friend), o-nitrophenol standard items (99%) and o-aminophenol standard items (98%)
(Sa grace chemical technology (Shanghai)), water is ultrapure water, and all reagents make after using the membrane filtration of 0.22 um and ultrasonic degassing
With.
Obtaining o-nitrophenol using peak area by high efficiency liquid phase chromatographic analysis method is ordinate concentration as the mark of abscissa
Directrix curve figure, obtaining o-aminophenol using peak area by high efficiency liquid phase chromatographic analysis method is ordinate concentration as the mark of abscissa
Directrix curve figure.
The preparation of standard solution: accurately weighing 0.10 g o-nitrophenol methanol dilution and constant volume holds in 100 mL
In measuring bottle, 0.10 g o-aminophenol methanol dilution and constant volume are accurately weighed in a 100 mL volumetric flasks, as adjacent nitre
Base phenol and o-aminophenol standard reserving solution；Accurately weigh 0.10 g o-nitrophenol and o-aminophenol standard items respectively again
In a 100 mL volumetric flasks, with methanol dilution and constant volume, as o-nitrophenol and o-aminophenol hybrid standard deposit
Liquid.
The preparation of test solution: the sample for accurately pipetting the electrosynthesis glyoxal o-aminophenol for being adjusted to neutrality through pre-treatment is molten
Liquid 0.5mL is settled in 10 mL volumetric flasks with flowing phase dilution, as detection o-aminophenol and o-nitrophenol for examination
Product solution.
Accurate measurement o-aminophenol and o-nitrophenol standard reserving solution are appropriate respectively, are made into often with flowing phase dilution
Contain the o-aminophenol or o-nitrophenol of 1.0,5.0,10.0,15.0,20.0,25.0,30.0,35.0,40.0 ug in 1mL；
20 uL test fluids are accurately injected by chromatograph quantitative loop to be analyzed in high performance liquid chromatograph, and chromatogram is obtained.Respectively with
Peak area is ordinate, and concentration is abscissa, obtains the canonical plotting of o-nitrophenol, o-aminophenol (such as Fig. 3,4 institutes
Show), linearly dependent coefficient R is respectively 0.9995 and 0.9998.
The stability test of solution
The stability test result of 1 solution of table
| Compound | Time | Peak area | Average value | RSD |
| 1 | 359565.688 | |||
| 2 | 352199.063 | |||
| O-aminophenol | 3 | 353556.250 | 355743.794 | 1.05 |
| 4 | 352705.719 | |||
| 5 | 360692.250 | |||
| 1 | 512666.781 | |||
| 2 | 502117.906 | |||
| O-nitrophenol | 3 | 510128.344 | 505830.256 | 1.05 |
| 4 | 503617.313 | |||
| 5 | 500620.938 |
Accurately pipetting each 0.20 mL of o-aminophenol, o-nitrophenol standard reserving solution is respectively placed in 10 mL volumetric flasks
In, scale is diluted to mobile phase.It is primary every the measurement of 1 h sample introduction, continuous sample introduction 5 times, its peak area is measured, RSD is
1.05%, show that sample solution is basicly stable in 5h, concrete outcome is shown in Table 1.
The precision test of method
The precision of 2 method of table
| Compound | Additional amount | Peak area | Average value | RSD |
| 359565.688 | ||||
| 353947.500 | ||||
| 353034.656 | ||||
| 356157.344 | ||||
| O-aminophenol | 20 | 350338.781 | 352464.792 | 1.04 |
| 352199.063 | ||||
| 348441.125 | ||||
| 349877.563 | ||||
| 348621.406 | ||||
| 512666.781 | ||||
| 502117.906 | ||||
| 510128.344 | ||||
| 508140.844 | ||||
| O-nitrophenol | 20 | 504485.156 | 507231.656 | 0.68 |
| 507891.438 | ||||
| 503617.313 | ||||
| 510029.438 | ||||
| 506007.688 |
Accurately pipette 0.20mL o-aminophenol respectively, o-nitrophenol is placed in two 10 mL volumetric flasks, use mobile phase
Constant volume, it is each to be measured in parallel 9 times, its peak area is measured, RSD is respectively 1.04% and 0.68%, and it is good heavy to show that this method has
Renaturation, see Table 2 for details for measurement result.
Sample analysis and recovery of standard addition measurement
The measurement of 3 sample size of table and recovery of standard addition experimental result
Each two parts of test solution of 3 batches are accurately pipetted, are respectively placed in 10 mL volumetric flasks, with flowing phase dilution
And constant volume, a copy of it are quantitatively adding the hybrid standard sample of o-aminophenol and o-nitrophenol, according to the chromatostrip after optimization
Part analyze while o-aminophenol and o-nitrophenol, and carries out recovery of standard addition measurement.The result shows that two kinds of chemical combination
The rate of recovery of object respectively between 93.0% ~ 105.6% and 90.6% ~ 106.2%, relative standard deviation difference≤3.75% and≤
1.44%, this method can be used for measurement while o-nitrophenol and o-aminophenol in sample solution, and concrete outcome is shown in Table 3.
Claims (2)
1. a kind of measure the method for preparing o-aminophenol yield using o-nitrophenol by high efficiency liquid phase chromatographic analysis method,
It is characterized in that: being carried out according to following step
Step 1: being obtained respectively by high efficiency liquid phase chromatographic analysis method using peak area is ordinate concentration as the adjacent nitro of abscissa
The canonical plotting of phenol and o-aminophenol；
Step 2: it is molten to obtain the final sample for preparing o-aminophenol using o-nitrophenol by high efficiency liquid phase chromatographic analysis method
The high-efficient liquid phase chromatogram of liquid, in high efficiency liquid phase chromatographic analysis method, chromatographic column is Shim-pack VP-ODS, and Detection wavelength exists
Between 270 ~ 300 nm, mobile phase is methanol: the solution of water=60 ~ 100%, and flow rate of mobile phase is 0.4 ~ 1.4 ml/min, chromatography
25 ~ 40 DEG C of column column temperature range, sample volume are 20 μ L；
Step 3: obtain the peak area of o-nitrophenol and o-aminophenol respectively from the high-efficient liquid phase chromatogram in step 2,
They are substituted into respectively in step 1 using peak area is ordinate concentration as the o-nitrophenol of abscissa and o-aminophenol
Canonical plotting obtains the concentration of o-nitrophenol and o-aminophenol, yield=(the actual measurement quality of o-aminophenol is dense respectively
Degree/o-aminophenol Theoretical Mass concentration) * 100%.
2. a kind of measured by high efficiency liquid phase chromatographic analysis method according to claim 1 prepares adjacent ammonia using o-nitrophenol
The method of base phenol yield, it is characterised in that: in high efficiency liquid phase chromatographic analysis method, Detection wavelength is 285 nm, and mobile phase is
100% methanol, flow rate of mobile phase are 0.80 ml/min, and chromatographic column column temperature is 35 DEG C.
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| CN108828100B (en) * | 2018-08-03 | 2021-04-09 | 湖州出入境检验检疫局综合技术服务中心 | Method for testing nitrobenzene compounds in textiles and leather products |
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| WO1995024465A1 (en) * | 1994-03-11 | 1995-09-14 | E.I. Du Pont De Nemours And Company | Single bacterial isolates for the degradation of nitrogen containing phenol compounds |
| CN101216468A (en) * | 2008-01-11 | 2008-07-09 | 上海化学试剂研究所 | 2-methoxymethyl-4-aminophenol and its impurity highly effective liquid phase chromatography analytical method |
| CN102267943A (en) * | 2011-07-29 | 2011-12-07 | 江苏力达宁化工有限公司 | Method for preparing 5-chloro-8-hydroxyquinoline |
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| JP2686947B2 (en) * | 1988-01-25 | 1997-12-08 | コニカ株式会社 | Method for producing 2- (phenylureido) aminophenols |
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| WO1995024465A1 (en) * | 1994-03-11 | 1995-09-14 | E.I. Du Pont De Nemours And Company | Single bacterial isolates for the degradation of nitrogen containing phenol compounds |
| CN101216468A (en) * | 2008-01-11 | 2008-07-09 | 上海化学试剂研究所 | 2-methoxymethyl-4-aminophenol and its impurity highly effective liquid phase chromatography analytical method |
| CN102267943A (en) * | 2011-07-29 | 2011-12-07 | 江苏力达宁化工有限公司 | Method for preparing 5-chloro-8-hydroxyquinoline |
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