CN101216468B - 2-methoxymethyl-4-aminophenol and its impurity highly effective liquid phase chromatography analytical method - Google Patents
2-methoxymethyl-4-aminophenol and its impurity highly effective liquid phase chromatography analytical method Download PDFInfo
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- CN101216468B CN101216468B CN2008100325633A CN200810032563A CN101216468B CN 101216468 B CN101216468 B CN 101216468B CN 2008100325633 A CN2008100325633 A CN 2008100325633A CN 200810032563 A CN200810032563 A CN 200810032563A CN 101216468 B CN101216468 B CN 101216468B
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- aminophenol
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Abstract
The invention discloses a high-performance liquid chromatographic analysis method of 2-methoxymethyl-4-aminophenol and impurities thereof. The method comprises the following steps of: selecting reverse high-performance liquid chromatography; setting chromatographic conditions, wherein the chromatographic column is C18, 5 mum, 150*4.6 mm (I.D.), the mobile phase includes acetonitrile: phosphoric acid -phosphate buffer solution (pH 7.0) at a volume ratio of 45:55 with a flow rate of 0.8 ml/min, the column temperature is 30 DEG C, the detection wavelength is 232 nm, the injection dose is 5 to 10mul, and (NH4)2HPO4 20 mmol/l is added into the mobile phase; adding phosphoric acid to adjust pH to 7.0; diluting the concentration of the injection sample to 1/50; and determining the contents of 2-methoxymethyl-4-aminophenol and the impurities thereof. The invention provides a simple and reliable method for quality control and analysis of 2-methoxymethyl-4-aminophenol.
Description
Technical field
The present invention relates to the HPLC analytical method of a kind of 2-methoxymethyl-4-aminophenol and impurity thereof.
Background technology
The 2-methoxymethyl-4-aminophenol is a kind of dyestuff intermediate, especially can be used as the developer in the oxidative coloration of hair agent, and at dyestuff, the hair dyeing field has a wide range of applications.Initiation material 2-methoxyl methyl-4-nitrophenol by hydrogen reducing, can prepare the 2-methoxymethyl-4-aminophenol under the catalytic condition of metallic catalyst palladium:
Possibly there are raw material 2-methoxyl methyl-impurity such as 4-nitrophenol in the 2-methoxymethyl-4-aminophenol product; The height of its content directly influences the quality of final products; Even human body caused very big harm, the monitoring to raw material 2-methoxyl methyl-impurity contents such as 4-nitrophenol when therefore analyzing 2-methoxymethyl-4-aminophenol content is very important.Do not see at present the report of measuring 2-methoxymethyl-4-aminophenol and impurity content method thereof as yet.
Summary of the invention
The HPLC analytical method that the purpose of this invention is to provide a kind of 2-of mensuration methoxymethyl-4-aminophenol and impurity thereof.
Technical scheme of the present invention is following:
The HPLC analytical method of a kind of 2-methoxymethyl-4-aminophenol and impurity thereof is characterized in that adopting reversed-phased high performace liquid chromatographic, and high-efficient liquid phase chromatogram condition is:
Chromatographic column: C
18, 5 μ m, 150 * 4.6mm (I.D.),
The volume ratio that moving phase is formed: acetonitrile: the phosphoric acid-phosphate-buffered WS (PH7.0)=45: 55,
Flow velocity: 0.8ml/min,
Column temperature: 30 ℃,
Detect wavelength: 232nm,
Sample size: 5-10 μ l.
According to HPLC analytical method of the present invention, with 50 times of the sample introduction sample concentration dilutions of measuring content, measure the content of 2-methoxymethyl-4-aminophenol main body and impurity thereof, add phosphate 20mmol/l (NH in the moving phase of the present invention
4)
2HPO
4, using phosphoric acid regulating ph value is 7.0.
Adopt the HPLC analytical method of 2-methoxymethyl-4-aminophenol of the present invention and impurity thereof; When accurately measuring 2-methoxymethyl-4-aminophenol main content; Can accurately measure the content of impurity 2-methoxyl methyl-4-nitrophenol, for the Quality Control Analysis of 2-methoxymethyl-4-aminophenol provides the Simple and Reliable analytical approach.
Description of drawings
Fig. 1 is the chromatogram of sample, and wherein: Fig. 1-a does not add phosphoric acid-phosphate-buffered WS in the moving phase; Fig. 1-b adds phosphate 20mmol/l (NH in moving phase
4)
2HPO
4, using phosphoric acid regulating ph value is 7.0.2.8 minutes peak is the 2-methoxymethyl-4-aminophenol among the figure, and 5.9 minutes peak is 2-methoxyl methyl-4-nitrophenol.
Fig. 2 is a ultraviolet spectrogram, and wherein: Fig. 2-a is a 2-methoxymethyl-4-aminophenol ultraviolet spectrogram; Fig. 2-b is 2-methoxyl methyl-4-nitrophenol ultraviolet spectrogram.
Fig. 3 is a 2-methoxymethyl-4-aminophenol canonical plotting.
Fig. 4 is 2-methoxyl methyl-4-nitramino phenol canonical plotting.
Fig. 5 is the chromatogram of raw material 2-methoxyl methyl in the sample-4-nitramino phenol content.
Embodiment
Main experimental apparatus and chromatographic condition:
Waters 1525 type high performance liquid chromatographs, Waters 717plus automatic sampler is joined Waters 2996 type diode array (PDA) detecting devices, and the control of chromatographic fractionation system and record are accomplished by Waters Empower chromatogram management system.
That chromatographic column is selected for use is C
18, 5 μ m, 150 * 4.6mm (I.D), moving phase: acetonitrile: the phosphoric acid-phosphate-buffered WS (PH=7.0)=45: 55, flow velocity: 0.8ml/min, column temperature: 30 ℃, detect wavelength: 232nm.
Reagent and medicine:
2-methoxymethyl-4-aminophenol reference substance (＞99.0%)
2-methoxyl methyl-4-nitrophenol reference substance (＞99.0%)
Acetonitrile (HPLC level);
The phosphate-buffered WS (PH=7.0)
Moving phase and solution with water are the quartzy distilled water of secondary in the experiment.
Embodiment 1: the selection of high-efficient liquid phase chromatogram condition
1.1 the selection of moving phase
Acetonitrile is used in experiment: the moving phase isocratic elution of water=45: 55,2-methoxymethyl-4-aminophenol and impurity separation case are good.But because amino in the 2-methoxymethyl-4-aminophenol and hydroxyl can interact with remaining silicon hydroxyl in the chromatographic column; Caused 2-methoxymethyl-4-aminophenol chromatographic peak that phenomenon (Fig. 1-a), influence the accuracy of quantitative test 2-methoxymethyl-4-aminophenol of hangover is arranged.Be employed in and add phosphate 20mmol/l (NH in the moving phase
4)
2HPO
4And to use phosphoric acid regulating ph value be 7.0 method, can eliminate conditions of streaking (Fig. 1-b) of chromatographic peak.
1.2 detect the selection of wavelength
Carry out continuous sweep with PDAD at 200-400nm, the 2-methoxymethyl-4-aminophenol has characteristic absorption (Fig. 2-a), and 2-methoxyl methyl-4-nitrophenol has characteristic absorption (Fig. 2-b) at 229nm and 318nm place at 235nm and 303nm place.Take into account each component sensitivity, selecting to detect wavelength is 232nm.
1.3 the selection of sample concentration
In order to take into account the mensuration of major component content and impurity content, when measuring impurity, the concentration of sample must be enough big, so that impurity can go out the peak; When measuring major component, solution concentration is crossed conference and is caused main peak to exceed the range of linearity and make quantitatively inaccurately, so measure behind 50 times of the diluted samples again, tests accuracy and sees table 1.
Embodiment 2: the preparation of standard solution and sample solution
Accurate weighing 50.00mg 2-methoxymethyl-4-aminophenol reference substance; Place the 50ml volumetric flask, with moving phase dissolving and be diluted to scale, shake up; Being made into concentration is the standard reserving solution of the 2-methoxymethyl-4-aminophenol of 1.0mg/ml, and stepwise dilution is to desired concn during use.
Accurately take by weighing 25.00mg 2-methoxyl methyl-4-nitrophenol reference substance; Place the 50ml volumetric flask, with moving phase dissolving and be diluted to scale, shake up; Getting concentration is the standard reserving solution of 2-methoxyl methyl-4-nitrophenol of 0.5mg/ml, and stepwise dilution is to desired concn during use.
Embodiment 3: the making of typical curve
High-efficient liquid phase chromatogram condition: chromatographic column is C
18, 5 μ m, 150 * 4.6mm (I.D); The volume ratio that moving phase is formed: acetonitrile: the phosphoric acid-phosphate-buffered WS (PH7.0)=45: 55; Flow velocity 0.8ml/min; 30 ℃ of column temperatures; Detect wavelength 232nm.Get 2-methoxymethyl-4-aminophenol standard solution 10 μ l sample introductions, with peak area to concentration mapping (Fig. 3).The 2-methoxymethyl-4-aminophenol is linear in the scope of solution concentration 0.0001～1.0mg/ml, and regression equation is:
A
The 2-methoxymethyl-4-aminophenol=193754.33232+3.31341E7C, r=0.99997
Get 2-methoxyl methyl-4-nitrophenol standard solution 10 μ l sample introductions, with peak area to concentration mapping (Fig. 4).2-methoxyl methyl-4-nitrophenol is linear in solution concentration is the scope of 0.0001～0.10mg/ml, and regression equation is:
A
2-methoxyl methyl-4-nitrophenol=12476.47946+1.79587E7C, r=0.99953
When signal to noise ratio (S/N ratio) S/N=3, the LDL that records 2-methoxymethyl-4-aminophenol and 2-methoxyl methyl-4-nitrophenol is respectively 0.00001mg/ml and 0.00002mg/ml.
Embodiment 4: the mensuration of sample
4.1 main Determination on content
Accurately take by weighing 50.0mg 2-methoxymethyl-4-aminophenol sample, place the 50ml volumetric flask, with moving phase dissolving and be diluted to scale, shake up, concentration be the solution of 1.0mg/ml.Get above-mentioned 1.0mg/ml solution 1.0ml and place the 50ml volumetric flask, add moving phase and be diluted to scale, shake up, get the solution of 0.02mg/ml, subsequent use.
Select the sample of any 5 lot numbers, prepare the 0.02mg/ml sample solution as stated above.High-efficient liquid phase chromatogram condition, chromatographic column C
18, 5 μ m, 150 * 4.6mm (I.D); The volume ratio that moving phase is formed: acetonitrile: the phosphoric acid-phosphate-buffered WS (PH7.0)=45: 55; Flow velocity 0.8ml/min; 30 ℃ of column temperatures; Detect wavelength 232nm and carry out HPLC and analyze, sample size is 10 μ l (Fig. 1-b).
4.2 the mensuration of impurity content
Select the sample of any five lot numbers, prepare the 1.0mg/ml sample solution as stated above.High-efficient liquid phase chromatogram condition: chromatographic column C
18, 5 μ m, 150 * 4.6mm (I.D); The volume ratio that moving phase is formed: acetonitrile: the phosphoric acid-phosphate-buffered WS (PH7.0)=45: 55; Flow velocity is 0.8ml/min; Column temperature is 30 ℃; Detecting wavelength is that 232nm carries out the HPLC analysis, and sample size is 10 μ l (Fig. 5).
The testing result of major component 2-methoxymethyl-4-aminophenol and impurity 2-methoxyl methyl-4-nitrophenol is listed in table 1 in the sample.
Table 1. testing result
| Lot number | The 2-methoxymethyl-4-aminophenol | 2-methoxyl methyl-4-nitrophenol | ||
| Content % | RSD％ | Content % | RSD％ | |
| 1 | 99.30 | 0.45 | 0.29 | 1.5 |
| 2 | 99.26 | 0.48 | 0.33 | 1.8 |
| 3 | 99.23 | 0.37 | 0.38 | 2.0 |
| 4 | 99.28 | 0.53 | 0.34 | 2.1 |
| 5 | 99.21 | 0.34 | 0.27 | 1.5 |
Claims (2)
1. the HPLC analytical method of a 2-methoxymethyl-4-aminophenol is characterized in that comprising the steps:
1) adopt reversed-phased high performace liquid chromatographic, the condition of high performance liquid chromatography is:
Chromatographic column: C
18, 5 μ m, I.D. are 150 * 4.6mm,
The volume ratio that moving phase is formed: the phosphoric acid of acetonitrile: the pH7.0-phosphate-buffered WS=45: 55,
Flow velocity: 0.8ml/min,
Column temperature: 30 ℃,
Detect wavelength: 232nm,
Sample size: 5-10 μ l;
2) prepare the standard solution and the sample solution of 2-methoxymethyl-4-aminophenol, 2-methoxyl methyl-4-nitrophenol respectively;
3) production standard curve;
4) mensuration of sample size;
Wherein, behind 50 times of the sample introduction sample concentration dilutions of measuring content, measure the content of 2-methoxymethyl-4-aminophenol main body again.
2. HPLC analytical method according to claim 1 is characterized in that, phosphate is the (NH of 20mmol/l in moving phase
4)
2HPO
4, using the phosphorus acid for adjusting pH value is 7.0.
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| CN101539544B (en) * | 2009-02-05 | 2013-12-04 | 上海华谊（集团）公司 | Method for analyzing content of trans-butene diacid mono-methyl fumarate and impurities thereof by high performance liquid chromatography |
| CN101629937B (en) * | 2009-08-18 | 2012-07-04 | 中国农业科学院农业环境与可持续发展研究所 | Quantitative detection method of pentachlorophenol in soil |
| CN104237405B (en) * | 2014-09-05 | 2015-12-09 | 北京理工大学 | The method of TATB synthetic intermediate and product in liquid chromatogram measuring waste water |
| CN106501412B (en) * | 2016-11-23 | 2019-04-16 | 太原理工大学 | A method of it is measured by high efficiency liquid phase chromatographic analysis method and prepares o-aminophenol yield using o-nitrophenol |
| CN109541114B (en) * | 2019-01-24 | 2021-01-22 | 山东省烟台市农业科学研究院 | Method for detecting residual quantity of compound sodium nitrophenolate in fruits and vegetables |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN88102680A (en) * | 1987-04-29 | 1988-11-23 | 诺拉姆科有限公司 | Method for purifying crude 4-aminophenol |
| US6200353B1 (en) * | 2000-02-01 | 2001-03-13 | Bristol Myers Squibb Company | Coupler for use in oxidative hair dyeing |
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2008
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN88102680A (en) * | 1987-04-29 | 1988-11-23 | 诺拉姆科有限公司 | Method for purifying crude 4-aminophenol |
| US6200353B1 (en) * | 2000-02-01 | 2001-03-13 | Bristol Myers Squibb Company | Coupler for use in oxidative hair dyeing |
Non-Patent Citations (2)
| Title |
|---|
| 王莉明.高效液相色谱法测定对氨基苯酚.《辽宁化工》.2002,第31卷(第8期),第360-361页. * |
| 薜长彬等.硝基苯电解还原液中对氨基苯酚的测定.《化学世界》.2006,第129-130页. * |
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