CN107091891A - A kind of chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid in Diethanolamine Dehydrogenation product - Google Patents
A kind of chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid in Diethanolamine Dehydrogenation product Download PDFInfo
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- CN107091891A CN107091891A CN201710353154.2A CN201710353154A CN107091891A CN 107091891 A CN107091891 A CN 107091891A CN 201710353154 A CN201710353154 A CN 201710353154A CN 107091891 A CN107091891 A CN 107091891A
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- glycine
- iminodiacetic acid
- dehydrogenation product
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
Abstract
The invention discloses a kind of chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid in Diethanolamine Dehydrogenation product, selected chromatographic separation condition makes iminodiacetic acid, glycine and other accessory substances completely separable, the content of iminodiacetic acid and glycine in energy accurate quantitative analysis Diethanolamine Dehydrogenation product.In 0.045~0.300g/L glycine concentration and 0.010~0.150mg/L iminodiacetic acid concentration, quantified by external standard method, the concentration of iminodiacetic acid and glycine is in strict linear relationship with peak area, and linearly dependent coefficient is more than 0.9999, and relative standard deviation is within 1.5%.Separating degree of the present invention is good, and analysis result accuracy and repeatability are high, and chromatographic column long lifespan disclosure satisfy that the quantitative analysis demand in research and production.
Description
Technical field
The present invention relates to determining for a kind of glycine that can be determined simultaneously in Diethanolamine Dehydrogenation product and iminodiacetic acid
Analysis method
Background technology
Iminodiacetic acid (IDA) is important chemical intermediate, is widely used in agricultural chemicals, chemical industry, medicine and other fields.At present
The method of production iminodiacetic acid mainly has chloroactic acid method, glycine method, ammonia for chloroactic acid method, nitrilotriacetic acid both at home and abroad
(the production of a rich iminodiacetic acid such as method, hydrogen cyanide direct synthesis technique, diethanol amine catalytic dehydrogenation methods and MEA method
Technical progress [J] finely with specialty chemicals .2005.13 (9):6-7.).Because diethanol amine catalytic dehydrogenation methods are economic and environment-friendly,
Production cost is significantly reduced than traditional handicraft, and high income, good product quality, and a large amount of scholar are studying the work both at home and abroad at present
Skill route.Therefore, set up that a kind of efficiently, fast, accurately method analyzes the principal product in diethanol amine catalytic dehydrogenation product
The amount of iminodiacetic acid and accessory substance glycine is just very necessary.
At present, the conventional analysis method of amino acids has：Potentiometric titration, ultraviolet spectrophotometry and anti-phase height
Effect liquid phase chromatogram method etc..
(1) potentiometric titration：The research of Li Yan girl's diethanol amine oxidative dehydrogenation iminodiacetic acid Cu-Zr catalysts
[D] Zhejiang：Zhejiang Normal University, 2011：21-23；Liu's length is flown and mixed using electrodialysis separation of glycine with iminodiacetic acid
Method [P] Chinese patents of compound：101792397A,2010-8-4.During using potentiometric titration, the content obtained by determining
It is all sour contents in sample (including glycine and iminodiacetic acid etc.), but this method determines Diethanolamine Dehydrogenation product
Influence factor to analysis result is relatively more, takes, and manual operation error is big, and sensitivity is low, and analysis result accuracy is poor.
(2) ultraviolet spectrophotometry：Imino-diacetic in Wang Na, yellow east ultraviolet spectrophotometry glycin mother liquids forever
Acetic acid [J] physical and chemical inspections-chemistry fascicle .2016,52 (10):1175-1177；In a kind of double sweet phosphorus mother liquors of Hu Xin, Luo Yan paddy
The analysis method of iminodiacetic acid composition：CN102706986A[P].2012.Such analysis method needs to utilize natrium nitrosum
Or alum generates complex with IDA, according to the ultraviolet absorptivity As of complex in sample and the ultraviolet light absorption of reference substance complex
Degree Ar compares, and calculates the content for obtaining iminodiacetic acid in sample.The method early-stage preparations time length is, it is necessary to by reference substance and sample
Product are detected with blank assay respectively, and need constantly adjustment extension rate to absorbance to be more than 0.01, complex steps.
(3) reversed-phased high performace liquid chromatographic：Using the reversed-phased high performace liquid chromatographic of C18 posts：Due to amino acids chemical combination
The UV absorption of thing is smaller, directly bad, it is necessary to use column front derivation to amino acids using effect during C18 posts
Afterwards, analyzed using reversed-phased high performace liquid chromatographic, its principle is mainly the UV absorption coefficient of increase material.The document of the method
Have：The new pre-column derivatization agents of Fang Fang, Wei Rong minister in ancient times analyze High Performance Liquid Chromatography Study [J] biological processings of glyphosate,
2014,12 (3)：69-72；Free amino acid [J] is eaten in Zhao Ying lotus .2,4- dinitrofluorobenzene column front derivations HPLC detection raspberries
Product science, 2015,36 (6):178-182；Slaughter the high-efficient liquid phase color of spring swallow , Zhao Jun new derivative reagent column front derivation amino acid
Analysis of spectrum [J] analysis test journals, 2008,27 (7)：681-685；Fang Fang, Xu can column front derivation RPLCs
Method determines amino acid content [J] food security quality testing journals, 2015,6 (6) in Ledum palustre：1993-1998.Should
Derivating agent used in class method is generally OPA, phenyl isothiocyanate, 2,4 dinitrofluorobenzene and benzene sulfonyl chloride class
Material.The shortcoming of such method is that derivative accessory substance can influence measure, and severe reaction conditions, while can be brought to mask work
Bigger difficulty, while derivating agent is mostly costly, and can pollute chromatographic column, reduces the service life of chromatographic column so that point
The expense increase of analysis.
(4) using the reversed-phased high performace liquid chromatographic of strong anion chromatographic column：Jia Chenglan, Du Jun industrial production glycine
The quick measure [J] of three kinds of carboxylic acids, 2012,24 (1) in crystalline mother solution:138-141.Such method can quickly determine imino group
The content of oxalic acid, sensitivity is high, easy to operate.But this method is only used for iminodiacetic acid and sweet ammonia in glycin mother liquid
The measure of acid.For the dehydrogenation reaction of diethanol amine, because reaction product is in addition to iminodiacetic acid and glycine, there is it
Its a variety of accessory substance, under described chromatographic condition, main side effect product can not be completely separable, and its separating degree does not reach quantitative
It is required that, and the peak of iminodiacetic acid is asymmetric in the presence of substantially trailing, it is impossible to Accurate Determining goes out the content of two kinds of materials in sample.
The content of the invention
It is an object of the invention to provide a kind of glycine and imino-diacetic that can be determined simultaneously in Diethanolamine Dehydrogenation product
The quantitative analysis method of acetic acid, the method can completely divide being realized in product between iminodiacetic acid, glycine and other components
From absorption disturbs small, sensitivity high, and the research and production optimization work of iminodiacetic acid can be prepared for diethanol amine catalytic dehydrogenation
Skill condition provides guidance.
Because glycine and iminodiacetic acid can ionize out anion in aqueous, according to various ions and fixation
Mutually occur the difference of the coulomb active force of ion exchange, it is organic using Agilent ZORBAX SAX (250mm × 4.6mm, 5 μm)
Anion chromatographic column is more more particularly suitable than C18 post, and the present invention, which chooses Agilent ZORBAX SAX (250mm × 4.6mm, 5 μm), to be had
Machine anion chromatographic column.The selection of mobile phase is the key of chromatographic isolation, and to ensure high separating degree, the present invention chooses di(2-ethylhexyl)phosphate
Hydrogen potassium cushioning liquid (pH value is 2~3) and methanol are flow visualizing, and take flowing phase concentration and flow dual factors gradient to wash
De-, glycine, iminodiacetic acid can be totally separated from other accessory substances.For column temperature, in general column temperature is to liquid
The separating degree influence of material is smaller in phase chromatogram, but for ionic compound, column temperature to the dissociation of ionic compound and
Ion-exchange speed is respectively provided with considerable influence, and the present invention is found especially that by experiment, different temperature, to separating effect and peak type
There is significant impact, when column temperature is higher, sample peak is more symmetrical, in order to ensure the separating effect of sample, peak type is symmetrical and extends
The service life of pillar, the selected column temperature of the present invention is 36~40 DEG C.For the selection of absorbing wavelength, pass through UV scanning glycine
With iminodiacetic acid standard substance, it is found that two kinds of materials have absworption peak at 200~210nm, by 200~210nm
In the range of contrast experiment, find two kinds of standard substances Detection wavelength be 200nm when, have maximum absorption area and highest
Peak height, with reference to the corresponding signal of accessory substance, it is 200nm to determine Detection wavelength.On flow velocity, during chromatographic isolation, flow velocity mainly leads to
Influence test substance is crossed with the interaction of stationary phase and mobile phase so as to influence the retention time of separate substance, flow velocity is too small,
Analysis time is long, and flow velocity is excessive, and various materials do not reach quantitative separating degree requirement, therefore take the graded of flow velocity yet.
On the selection of quantitative approach, experiment is found, in the range of finite concentration, quantified by external standard method, iminodiacetic acid and glycine
Concentration and peak area be in strict linear relationship, linearly dependent coefficient, can be to Diethanolamine Dehydrogenation product more than 0.9999
In glycine and the content of iminodiacetic acid quantified.
The use following technical scheme of the present invention：
A kind of chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid in diethanol amine product：
Liquid phase chromatogram condition：
(1) chromatographic column：Agilent ZORBAX SAX chromatographic columns；
(2) mobile phase：Component A：Concentration be 0.02~0.04mol/L dipotassium hydrogen phosphate solution, its pH value be 2.0~
3.0；B component：Concentration is 100% methanol；
(3) mobile phase concentration gradient：Time/min 0~15, component A mobile phase volume fraction/%100~90, B component
Mobile phase volume fraction/%0~10；
(4) flow rate of mobile phase gradient：Time/min 0~15, flow velocity/ml.min-10.3~1.6；
(5) Detection wavelength：200~210nm；
(6) column temperature：36~40 DEG C；
The configuration and quantitative analysis method of standard liquid, sample solution：
(1) preparation of standard liquid：Glycine and iminodiacetic acid standard sample are accurately weighed respectively, are matched somebody with somebody with ultra-pure water
Into concentration be 0.045~0.300g/L and concentration is 0.010~0.150mg/L glycine and iminodiacetic acid series concentration
Standard liquid；
(2) drafting of standard curve：Under above-mentioned liquid phase chromatogram condition, respectively to glycine and iminodiacetic acid series
Reference material is detected, standard substance concentration is mapped with peak area, glycine and iminodiacetic acid reference material standard is obtained
Curve；
(3) regression equation of glycine and iminodiacetic acid is respectively：
NGly(A)=1573.4CGly+ 1.894, R=0.99991；
NIDA(A)=9720.8120CIDA- 8.87896, R=0.99993；
(4) preparation of Diethanolamine Dehydrogenation Product samples and measure：
Diethanolamine Dehydrogenation product is taken, 0.01~0.03% concentration is diluted to ultra-pure water, mixes equal with ultrasonic oscillation
It is even, and pH value is adjusted to 2.0~4.0 with phosphoric acid solution, ultra-pure water constant volume is mixed and deaerated with ultrasonic oscillation, is configured to two
Monoethanolamine dehydrogenation product sample；Under above-mentioned liquid phase chromatogram condition, Diethanolamine Dehydrogenation Product samples are detected, continuously entered
Sample five times, obtains the analysis collection of illustrative plates of Diethanolamine Dehydrogenation product；Glycine and iminodiacetic acid according to measured by collection of illustrative plates
Peak area, substitutes into the regression equation of glycine and iminodiacetic acid, and calculating obtains sweet ammonia in Diethanolamine Dehydrogenation Product samples
The content of acid and iminodiacetic acid；
(5) in Diethanolamine Dehydrogenation Product samples glycine and iminodiacetic acid cubage formula：
CGly=n × (NGly(A)-1.894)/1573.4
CIDA=n × (NGly(A)+8.87896)/972.0812
In formula, CGlyFor the grams (g/L) of glycine in every liter of Diethanolamine Dehydrogenation product, CIDAIt is de- for every liter of diethanol amine
The grams (g/L) of iminodiacetic acid in hydrogen product, n is the multiple of Diethanolamine Dehydrogenation product dilution, NGly(A)For diethanol amine
The peak area and N of glycine in dehydrogenation productGly(A)For the peak area of iminodiacetic acid in Diethanolamine Dehydrogenation product.
The inventive method focuses on to have studied iminodiacetic acid, glycine in diethanol amine catalytic dehydrogenation product separation sample
With the liquid chromatogram separation condition of other accessory substances, make glycine, iminodiacetic acid and other accessory substances completely separable, can be accurate
It is determined that the content of the iminodiacetic acid and glycine in amount Diethanolamine Dehydrogenation product.In 0.045~0.300g/L sweet ammonia
The iminodiacetic acid concentration of acid concentration and 0.010~0.150mg/L, quantified by external standard method, iminodiacetic acid and glycine
Concentration and peak area are in strict linear relationship, linearly dependent coefficient more than 0.9999, relative standard deviation 1.5% with
It is interior, compared with other analysis methods, the method has separating degree good, and analysis result accuracy and repeatability are high, chromatographic column long lifespan
The advantages of.
The innovative point of the present invention is to be, have found the chromatographic separation condition of optimization, solves Diethanolamine Dehydrogenation product
Middle glycine and iminodiacetic acid are difficult to separate with other accessory substances, so that the problem of being unable to accurate quantitative analysis, this point of invention
Analysis method, the optimization that iminodiacetic acid process conditions can be prepared for Diethanolamine Dehydrogenation improves main reaction selectivity and product receipts
Rate provides effective instruct.
Brief description of the drawings
Fig. 1 glycine standard curves.
Fig. 2 iminodiacetic acid standard curves.
Fig. 3 Diethanolamine Dehydrogenation Product samples separation chromatography figures.
Embodiment
A kind of chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid in Diethanolamine Dehydrogenation product,
1st, chromatographiccondition：
Use Agilent Technologies-1200 high performance liquid chromatographs, Agilent ZORBAX SAX anion
Chromatographic column, mobile phase is that component A 0.03mol/l potassium dihydrogen phosphates (pH value=2.2) and the methanol solution of B component 100% are constituted, and
Using linear gradient elution method to elute, (its mobile phase concentration gradient is time/min 0~15, component A mobile phase volume fraction/%
100~90, B component mobile phase volume fraction/%0~10；Flow rate of mobile phase gradient：Time/min 0~15, flow velocity/
ml.min-10.3~1.6), column temperature：38℃；Detection wavelength：200nm；Sample size：20μL.
2nd, the preparation of standard liquid：
It is accurate prepare 0.05,0.10,0.15,0.20,0.25g/L iminodiacetic acid standard liquid and 0.02,0.04,
0.06th, 0.08,0.10g/L glycine standard liquid.Filtered with syringe filters, take filtrate by selected chromatographic condition, enter
The μ L of sample 20 carry out liquid-phase chromatographic analysis.Using peak area as ordinate, concentration is mapped for abscissa, obtains Fig. 1 and Fig. 2.
Fig. 1 be glycine (Gly) standard curve, abscissa be peak area A/mAu, ordinate for glycine concentration C/
g.L-1,
Its regression equation is：NGly(A)=1573.4CGly+ 1.894, linearly dependent coefficient R=0.99991
Fig. 2 is the standard curve of iminodiacetic acid (IDA), and abscissa is peak area A/mAu, and ordinate is imino-diacetic
Concentration C/g.L of acetic acid-1,
Its regression equation is NIDA(A)=972.0812CIDA- 8.87896, linearly dependent coefficient R=0.99993
3rd, the measure of the preparation concentration of testing sample solution：
1mL solution to be measured is drawn into 50mL volumetric flasks, is diluted with ultra-pure water and adjusts its pH value=3 (and standard liquid
PH value is consistent), ultra-pure water constant volume is used after ultrasonic vibration is well mixed, is filtered with syringe filters.It is identical by standards solution analysis
Chromatographic condition, the μ L of sample introduction 20 carry out liquid-phase chromatographic analysis.
Fig. 3 is diethanol amine catalytic dehydrogenation Product samples separation chromatography figure, and the retention time and peak area at each peak are specifically
It is bright as shown in table 1：
The retention time and peak area (table 1) at each peak in sample separation liquid chromatogram
The peak area of the glycine measured in sample and iminodiacetic acid is substituted into glycine and iminodiacetic acid (salt) respectively
The regression equation of acid, it is that 0.0632g/L, iminodiacetic acid concentration are to calculate glycine concentration in the sample after being diluted
1.4868g/L.Due to 1mL samples have been diluted in 50mL volumetric flasks in case of the present invention, that is, dilute 50 times.So
The concentration of glycine is that 3.163g/L, the concentration of iminodiacetic acid are 74.34g/L in raw sample.
4. recovery of standard addition and relative standard deviation
Choose debita spissitudo (using Diethanolamine Dehydrogenation product as standard) sample solution, add 3 levels Gly and
IDA standard items, carry out recovery testu, and Gly3 pitch-based sphere is respectively：0.005、0.010、0.015g/L；IDA3
Pitch-based sphere is respectively：0.15th, 0.30,0.45g/L, each pitch-based sphere repeats sample introduction 5 times, and its result is as shown in table 2, table 3.
Gly mark-on reclaims result (table 2)
IDA mark-on reclaims result (table 3)
To ensure the accuracy of institute's survey data, in determining from Specification Curve of Increasing to solution concentration to be measured completely
During, standard liquid and solution to be measured for various concentrations, each step and chromatographic condition answer complete phase in its continuous mode
Together.Especially standard liquid should be consistent with the gradient elution program that solution to be measured is taken.
Claims (1)
1. the chromatogram quantitative analysis of the liquid phase method of glycine and iminodiacetic acid, its feature in a kind of Diethanolamine Dehydrogenation product
It is：
Liquid phase chromatogram condition：
(1) chromatographic column：Agilent ZORBAX SAX chromatographic columns；
(2) mobile phase：Component A：Concentration is 0.02~0.04mol/L dipotassium hydrogen phosphate solution, and its pH value is 2.0~3.0；B
Component：Concentration is 100% methanol；
(3) mobile phase concentration gradient：Time/min 0~15, component A mobile phase volume fraction/%100~90, B component flowing
Phase volume fraction/%0~10
(4) flow rate of mobile phase gradient：Time/min 0~15, flow velocity/ml.min-10.3~1.6；
(5) Detection wavelength：200~210nm；
(6) column temperature：36~40 DEG C；
The configuration and quantitative analysis method of standard liquid, sample solution：
(1) preparation of standard liquid：Glycine and iminodiacetic acid standard sample are accurately weighed respectively, are made into ultra-pure water dense
Degree is 0.045~0.300g/L and concentration is 0.010~0.150mg/L glycine and iminodiacetic acid series concentration standard
Solution；
(2) drafting of standard curve：Under above-mentioned liquid phase chromatogram condition, respectively to glycine and iminodiacetic acid series standard
Thing is detected, standard substance concentration is mapped with peak area, glycine and iminodiacetic acid reference material standard curve is obtained；
(3) regression equation of glycine and iminodiacetic acid is respectively：
NGly(A)=1573.4CGly+ 1.894, R=0.99991；
NIDA(A)=9720.8120CIDA- 8.87896, R=0.99993；
(4) preparation of Diethanolamine Dehydrogenation Product samples and measure：
Diethanolamine Dehydrogenation product is taken, 0.01~0.03% concentration is diluted to ultra-pure water, it is well mixed with ultrasonic oscillation, and
PH value is adjusted to 2.0~4.0 with phosphoric acid solution, and ultra-pure water constant volume is mixed and deaerated with ultrasonic oscillation, is configured to diethanol amine
Dehydrogenation product sample；Under above-mentioned liquid phase chromatogram condition, Diethanolamine Dehydrogenation Product samples are detected, continuous sample introduction five
It is secondary, obtain the analysis collection of illustrative plates of Diethanolamine Dehydrogenation product；The peak face of glycine and iminodiacetic acid according to measured by collection of illustrative plates
Product, substitutes into the regression equation of glycine and iminodiacetic acid, calculating obtain in Diethanolamine Dehydrogenation Product samples glycine and
The content of iminodiacetic acid；
(5) in Diethanolamine Dehydrogenation Product samples glycine and iminodiacetic acid cubage formula：
CGly=n × (NGly(A)-1.894)/1573.4
CIDA=n × (NGly(A)+8.87896)/972.0812
In formula, CGlyFor the grams (g/L) of glycine in every liter of Diethanolamine Dehydrogenation product, CIDAFor every liter of Diethanolamine Dehydrogenation production
The grams (g/L) of iminodiacetic acid in thing, n is the multiple of Diethanolamine Dehydrogenation product dilution, NGly(A)For Diethanolamine Dehydrogenation
The peak area and N of glycine in productGly(A)For the peak area of iminodiacetic acid in Diethanolamine Dehydrogenation product.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107621507A (en) * | 2017-08-28 | 2018-01-23 | 湘潭大学 | The liquid phase chromatography analytical method of simultaneous quantitative glycine and iminodiacetic acid in a kind of Diethanolamine Dehydrogenation product |
| CN110646531A (en) * | 2019-09-18 | 2020-01-03 | 湘潭大学 | Ion chromatography quantitative analysis method for raw material diethanolamine in reaction liquid for synthesizing iminodiacetic acid by dehydrogenation of diethanolamine |
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| CN101398413A (en) * | 2008-11-10 | 2009-04-01 | 浙江工业大学 | Liquid phase analytical method for iminodiacetic acid |
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| CN101398413A (en) * | 2008-11-10 | 2009-04-01 | 浙江工业大学 | Liquid phase analytical method for iminodiacetic acid |
Non-Patent Citations (3)
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| DANIEL A. HICKMAN ET AL.: "A continuous diethanolamine dehydrogenation fixed bed catalyst and reactor system", 《CHEMICAL ENGINEERING JOURNAL》 * |
| 伍君 等: "用于二乙醇胺脱氢的Cu/ZnO/Al2O3/ZrO2催化剂的制备与表征", 《精细化工》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107621507A (en) * | 2017-08-28 | 2018-01-23 | 湘潭大学 | The liquid phase chromatography analytical method of simultaneous quantitative glycine and iminodiacetic acid in a kind of Diethanolamine Dehydrogenation product |
| CN107621507B (en) * | 2017-08-28 | 2020-01-21 | 湘潭大学 | Liquid chromatography analysis method for simultaneously quantifying glycine and iminodiacetic acid in diethanolamine dehydrogenation product |
| CN110646531A (en) * | 2019-09-18 | 2020-01-03 | 湘潭大学 | Ion chromatography quantitative analysis method for raw material diethanolamine in reaction liquid for synthesizing iminodiacetic acid by dehydrogenation of diethanolamine |
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