CN113588811A - Detection method of 1, 2-propylene glycol enantiomer - Google Patents

Detection method of 1, 2-propylene glycol enantiomer Download PDF

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CN113588811A
CN113588811A CN202110741025.7A CN202110741025A CN113588811A CN 113588811 A CN113588811 A CN 113588811A CN 202110741025 A CN202110741025 A CN 202110741025A CN 113588811 A CN113588811 A CN 113588811A
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enantiomer
propanediol
detecting
propylene glycol
temperature
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黄勤
夏行
李卫鹏
黄想亮
孔叶青
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Zhejiang Menovo Pharmaceuticals Co ltd
Ningbo Menovo Pharmaceutical Co Ltd
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Ningbo Menovo Pharmaceutical Co Ltd
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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
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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
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Abstract

The invention provides a method for detecting 1, 2-propylene glycol enantiomer, which comprises the following steps: adding a derivatization reagent and a catalyst into a sample containing the 1, 2-propylene glycol enantiomer, performing derivatization, adding a diluent for dilution to obtain a test solution, and performing quantitative analysis according to a gas chromatography; the derivatization reagent is: an organic acid anhydride reagent. The invention solves the problems of tailing of chromatographic peaks and poor separation effect of the chromatogram, solves the problems of filtration and reproducibility before entering a gas phase system caused by adding a water removing agent, and applies the detection method of the 1,2-propanediol enantiomer with good effect in actual production and detection; effectively controls the quality of 1, 2-propylene glycol, 1, 2-propylene glycol-containing raw material medicaments and preparations thereof.

Description

Detection method of 1, 2-propylene glycol enantiomer
Technical Field
The invention relates to the field of analytical chemistry, in particular to a detection method of a 1, 2-propylene glycol enantiomer.
Background
The company Aslicon and Shi Guibao jointly researches and develops a sodium-glucose cotransporter 2(SGLT2) inhibitor for treating type 2 diabetes. Under the generic name Dapagliflozin (Dapagliflozin), the propylene glycol monohydrate thereof has the molecular formula C21H25O6Cl·C3H8O2·H2O, its chemical name is (2S,3R,4R,5S,6R) -2- (4-chloro-3- (4-ethoxybenzyl) phenyl) -6- (hydroxymethyl) tetrahydro-2H-pyran-3, 4, 5-triol- (S) -1, 2-propanediol monohydrate. In the process of synthesizing the dapagliflozin S-propylene glycol monohydrate, the dapagliflozin reacts with 1, 2-propylene glycol, and then the S-propylene glycol monohydrate is obtained through purification and crystallization, wherein the S-1, 2-propylene glycol and the isomer thereof are added. In the key raw material medicaments or preparations of 1, 2-propylene glycol and dapagliflozin, the contents of S-1, 2-propylene glycol and R-1, 2-propylene glycol need to be controlled, and the key link of quality control in the production of medicines is realized.
1,2-propanediol has no unsaturated bonds and conjugated groups in the chemical structure, so that ultraviolet absorption does not exist, and the detection cannot be carried out by liquid chromatography. At present, the 1, 2-propylene glycol and the isomers thereof are generally measured by gas chromatography, and the chiral gas chromatography column which takes chemically bonded cyclodextrin as a stationary phase is used for separation and measurement. The prior Journal literature "Determination of analytes of 1, 2-general in Beer by Gas Chromatography" ("Journal of Fermentation and biological engineering", volume 75, phase 5, page 339 and 343) discloses a method for detecting the content of 1, 2-isopropanol enantiomer by Gas Chromatography, which uses a DB-WAX chromatographic column and an FID detector and conventional detection conditions, but the detection spectrum has the defects of tail, poor peak shape and poor separation effect. The main reason is that the 1, 2-propylene glycol has two hydroxyl groups in the structure, which are easy to form hydrogen bonds with silanol (-Si-OH) on the surface of a chromatographic column stationary phase carrier, resulting in strong column adsorption, thereby causing serious tailing of chromatographic peaks, and further failing to separate S-1, 2-propylene glycol and R-type enantiomer thereof.
At present, patent CN105738533B discloses a method for separating and measuring 1,2-propanediol enantiomer by gas chromatography, which comprises performing pre-column derivatization by using a ketone or aldehyde derivatization reagent, a water reducing agent and a catalyst, stirring at room temperature, and injecting the filtrate filtered by a 0.45 μm filter membrane as a test solution into a gas chromatograph for detection. In the patent, a large amount of water is generated under the action of a derivatization reagent and a catalyst, so that the content of 1, 2-propylene glycol in a sample solution is reduced, and the detection result is poor, so that a large amount of water reducing agent is required to be added for dewatering; the water reducing agent in the patent is inorganic salt such as anhydrous magnesium sulfate and the like or a 4A molecular sieve, and cannot enter a gas chromatography system, otherwise, the gas chromatography system is blocked, so that a sample solution needs to be filtered; in addition, the operation steps are complicated, and the risk of reproducibility of the method is increased; and the chromatographic peak shape of the gas chromatographic spectrum is not symmetrical enough, and the chromatographic peak separation is not good enough.
Therefore, it is necessary to develop a method for detecting 1,2-propanediol enantiomer, which solves the problems of tailing of chromatographic peak and poor separation effect, and the problems of filtration and reproducibility before entering a gas phase system caused by adding a water removal agent, and has good application effect in actual production and detection.
Disclosure of Invention
In view of the above, the invention aims to develop a method for detecting 1,2-propanediol enantiomer by using gas chromatography, which meets the requirement of controlling the quality of S-1, 2-propanediol or its isomer in the key materials of 1,2-propanediol and dapagliflozin bulk drugs or preparations, and solves the problems of poor separation effect, complicated sample treatment, and low operability and reproducibility of the method.
In order to achieve the above object, the present invention provides a method for detecting enantiomers of 1,2-propanediol, comprising: adding a derivatization reagent and a catalyst into a sample containing the 1, 2-propylene glycol enantiomer, performing derivatization, adding a diluent to dilute to obtain a test solution, and performing quantitative analysis according to a gas chromatography.
Wherein the derivatizing reagent is: an organic acid anhydride reagent.
Further, the organic acid anhydride reagent is C1-C8 low carbon chain acid anhydride.
Still further, the derivatizing agent is selected from the group consisting of: one or more of formic anhydride, acetic anhydride, propionic anhydride, and butyric anhydride.
Wherein the catalyst is selected from one or more of sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid.
Wherein the diluent is dichloromethane. The reagent can also be other common diluents in gas phase detection, and can dilute the sample after derivatization.
Wherein the molar ratio of the sample containing the 1, 2-propylene glycol enantiomer to the derivatization reagent is 1 (2.5-20). Further preferably, the molar ratio of the sample containing 1,2-propanediol enantiomer to the derivatization reagent is 1 (2.5-10). More preferably, the molar ratio of the sample containing 1,2-propanediol enantiomer to derivatizing reagent is 1: 5.
Wherein the molar ratio of the catalyst to the sample containing the 1, 2-propylene glycol enantiomer is (0.05-0.5): 1. More preferably, the molar ratio of catalyst to sample containing the 1,2-propanediol enantiomer is 0.1: 1.
Wherein, the sample containing 1,2-propanediol enantiomer also contains dapagliflozin.
Wherein the derivatization time is 10 minutes to 10 hours, more preferably, the derivatization time is 30 minutes to 3 hours, and even more preferably, the derivatization time is 2 hours.
The invention provides a method for detecting 1, 2-propylene glycol enantiomer, wherein gas chromatography detection conditions are that chemically bonded beta-cyclodextrin is used as a stationary phase, a hydrogen ion flame detector is used as a detector, and a chromatogram is recorded at a proper column temperature.
Wherein the temperature of the sample inlet is 180-300 ℃; the split ratio is 1: 1-100: 1; the temperature of the detector is 200-320 ℃, and the flow rate of nitrogen or helium is 0.1-3.0 mL per minute.
The invention provides a method for detecting 1,2-propanediol enantiomer, wherein the column temperature during detection is temperature programming, elution can be carried out according to a conventional temperature programming mode, and the invention provides a better elution mode, wherein the temperature programming is carried out according to the following table 1:
TABLE 1 temperature programming table
Column temperature (. degree. C.) Retention time (min) Rate of temperature rise (. degree. C./min)
60 5 20
120 0 1
130 0 10
200 10 /
More preferably, the beta-cyclodextrin is CP-Chirasil-DEX CB, and more preferably, the specification of the CP-Chirasil-DEX CB is 25m multiplied by 0.25mm and 0.25 mu m.
Further preferably, the column flow rate is 1.5 mL/min.
Further preferably, the injection volume is 1 μ L.
The parameters of the column flow rate, the column temperature, the sample introduction volume, the concentration of the compound in the solution of the test sample and the like can be adjusted according to the actual detection condition, and the optimal value provided by the invention is a reference value.
To verify that the present invention is capable of fully separating both the R and S enantiomers of 1,2-propanediol, the present invention was demonstrated by systematic suitability testing. In the system adaptability test, a proper amount of (S) -1, 2-propylene glycol and (R) -1, 2-propylene glycol are respectively taken, a derivative reagent and a catalyst are added, the mixture is stirred for reaction, and a diluent is added for dilution to prepare a system adaptability solution, and the detection is carried out according to the detection method provided by the invention.
The detection result shows that the chromatographic peak with the retention time of 8.954min is the (R) -1, 2-propanediol derivative peak, and the chromatographic peak with the retention time of 8.598min is the (S) -1, 2-propanediol derivative peak. In a system adaptability test, the separation degree of (R) -1, 2-propylene glycol and (S) -1, 2-propylene glycol is 6.4, complete separation is achieved, the peak types are symmetrical, and the requirements of Chinese pharmacopoeia are met; compared with the chromatogram of patent CN105738533B, the peak shape is more symmetrical and the separation degree is higher.
Aiming at the defect that the separation cannot be realized due to serious tailing of chromatographic peaks in the conventional method, the technical scheme of the invention adopts chemically bonded beta-cyclodextrin as a stationary phase, a hydrogen ion flame detector as a detector, and proper temperature programming elution, can completely separate S-1, 2-propanediol and enantiomer thereof by utilizing a pre-column derivatization technology, has symmetrical peak types and accords with the regulations of Chinese pharmacopoeia; can control the content of the 1, 2-propylene glycol and the isomer thereof, and the S-1, 2-propylene glycol or the isomer thereof in the bulk drug or the preparation of the dapagliflozin. The method has the advantages of strong specificity, good separation degree, high sensitivity and good accuracy.
The derivatization reagent used in the invention is an acid anhydride reagent, which is not in the protection range of patent CN105738533B, and the derivatization reagent as a similar compound is not reported. The derivative is used as a derivative reagent and also serves as a water reducing agent to a certain extent, and the derivative reaction can be effectively promoted to be rapidly carried out, so that an additional water reducing agent is not required to be added; and the anhydride solvent can enter a gas chromatography detection system, so that the operation such as filtration and the like is not required to be added in the pretreatment process of the test solution, the operation can be effectively simplified, and the operability and the reproducibility of the method are improved.
Drawings
FIG. 1 shows a GC spectrum of a blank solution detected by the method of the present invention;
FIG. 2 shows a GC spectrum of an adaptive solution for a detection system using the method of the present invention;
FIG. 3 is a GC spectrum of a control solution tested using the method of the present invention;
FIG. 4 shows a GC spectrum of a test solution using the method of the present invention;
FIG. 5 shows a GC spectrum of a standard solution for detecting (S) -1, 2-propanediol by a conventional method (see example 3);
FIG. 6 shows a GC spectrum of a standard solution for detecting (R) -1, 2-propanediol by a conventional method (see example 3).
Detailed Description
The embodiment of the invention discloses an analysis method for testing 1, 2-propylene glycol enantiomer by adopting gas chromatography. Those skilled in the art can use the teachings herein to appropriately modify the chromatographic parameters. It is expressly intended that all such similar substitutes and modifications which would be obvious to one skilled in the art are deemed to be included in the invention. While the methods of the present invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the products and methods described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of the present invention without departing from the spirit and scope of the invention.
Before the GC method is used for the related substance test, a systematic adaptability test is required to confirm that the detection system can meet the detection requirement (generally, the separation degree of a main peak and adjacent impurities or the separation degree requirement between certain adjacent impurities). In the specific implementation mode, the invention verifies that (R) -1, 2-propylene glycol and (S) -1, 2-propylene glycol in the system adaptability solution can be completely separated and meet the requirements of Chinese pharmacopoeia.
In the specific embodiment, all reagents, medicines, test environments and the like used are the same and consistent in source without special description.
In order to further understand the present invention, the following examples are provided to illustrate the present invention in detail by using gas chromatography to detect 1,2-propanediol and its enantiomer.
Example 1: system suitability test
The instrument comprises the following steps: agilent 7890A gas chromatograph and workstation, FID detector and autosampler thereof
A chromatographic column: CP-Chirasil-DEX CB, CP7502(25 m.times.0.25 mm 0.25 μm)
-a carrier gas; helium gas
-flow rate: 2mL/min
-split ratio: 87:1
Column temperature: the initial temperature is 60 ℃ and kept for 5 minutes, the temperature is increased to 120 ℃ at the heating rate of 20 ℃/min, the temperature is increased to 130 ℃ at the heating rate of 1 ℃/min, and the temperature is increased to 200 ℃ at the heating rate of 10 ℃/min and kept for 10 minutes.
-injection port temperature: 200 deg.C
Detector temperature: 240 ℃ C
-air flow rate: 400mL/min
-hydrogen flow rate: 40mL/min
-purge gas: helium gas
-purge gas flow rate: 30mL/min
-volume of sample injection: 1 μ L
Transferring 50 mu L of methanesulfonic acid into a 25mL volumetric flask, diluting with acetic anhydride and fixing the volume to the scale, then adding magnetons, and magnetically stirring for 2 hours. Precisely transferring 2mL of the solution, placing the solution in a 20mL volumetric flask, adding a proper amount of dichloromethane for dilution, and fixing the volume to a scale to obtain a blank solution.
The blank solution was taken, subjected to measurement under the chromatographic conditions of this example, and a chromatogram was recorded, and the result is shown in FIG. 1.
Precisely weighing 25mg of (R) -1, 2-propylene glycol reference substance and about 2.5g of (S) -1, 2-propylene glycol reference substance, placing the reference substances in a 25mL volumetric flask, weighing 20mL of acetic anhydride, placing the acetic anhydride in the volumetric flask, adding 50 mu L of methanesulfonic acid, fixing the volume of the acetic anhydride to a scale, then placing a magneton, and magnetically stirring for 2 hours. Precisely transferring 2mL of the solution, placing the solution in a 20mL volumetric flask, adding a proper amount of dichloromethane for dilution, and fixing the volume to a scale to obtain a system adaptive solution.
Accurately weighing 25mg of (R) -1, 2-propylene glycol reference substance, placing the reference substance in a 25mL volumetric flask, weighing 20mL of acetic anhydride, placing the acetic anhydride in the volumetric flask, adding 50 mu L of methanesulfonic acid, fixing the volume of the acetic anhydride to a scale, then placing magnetons, and magnetically stirring for 2 hours. Precisely transferring 2mL of the solution, placing the solution in a 20mL volumetric flask, adding a proper amount of dichloromethane for dilution, and fixing the volume to a scale to obtain a standard solution.
The system-adapted solution was taken, subjected to measurement according to the chromatographic conditions of this example, and a chromatogram was recorded, and the result is shown in FIG. 2.
The standard solution was subjected to measurement under the conditions of chromatography in this example, and a chromatogram was recorded, and the result was shown in FIG. 3 (number 8.947 on the chromatogram).
TABLE 2 relative retention time and resolution of each compound in the system's adaptive solution
Serial number Name of Compound Retention time (min) Relative retention time Degree of separation
1 (S) -1, 2-propanediol 8.598 1.00 /
2 (R) -1, 2-propanediol 8.941 1.04 6.36
As can be seen from table 2, the degree of separation of (R) -1, 2-propanediol and (S) -1, 2-propanediol in the system-adapted solution was 6.36, achieving complete separation; from FIG. 2, it can be seen that the peak patterns of (R) -1, 2-propanediol and (S) -1, 2-propanediol are symmetrical and meet the requirements of Chinese pharmacopoeia.
Example 2: testing of (S) -1, 2-propanediol test solutions
The instrument comprises the following steps: an Agilent 7890A gas chromatograph and workstation thereof, an FID detector and an autosampler;
a chromatographic column: CP-Chirasil-DEX CB, CP7502(25 m.times.0.25 mm.0.25 μm);
-a carrier gas; helium gas
-flow rate: 2mL/min
-split ratio: 87:1
Column temperature: the initial temperature is 60 ℃ and kept for 5 minutes, the temperature is increased to 120 ℃ at the heating rate of 20 ℃/min, the temperature is increased to 130 ℃ at the heating rate of 1 ℃/min, and the temperature is increased to 200 ℃ at the heating rate of 10 ℃/min and kept for 10 minutes.
-injection port temperature: 200 deg.C
Detector temperature: 240 ℃ C
-air flow rate: 400mL/min
-hydrogen flow rate: 40mL/min
-purge gas: helium gas
-purge gas flow rate: 30mL/min
-volume of sample injection: 1 μ L
Accurately weighing about 2.5g of (S) -1, 2-propylene glycol, placing the weighed (S) -1, 2-propylene glycol into a 25mL volumetric flask, weighing 20mL of acetic anhydride, placing the acetic anhydride into the volumetric flask, adding 50 mu L of methanesulfonic acid, using the acetic anhydride to fix the volume to a scale, then placing magnetons, and magnetically stirring for 2 hours. Precisely transferring 2mL of the solution, placing the solution in a 20mL volumetric flask, adding a proper amount of dichloromethane for dilution, and fixing the volume to a scale to obtain a sample solution. The chromatogram obtained from the measurement performed under the chromatographic conditions of this example is shown in FIG. 4 (numeral 8.948).
The standard solution was taken, measured according to the chromatographic conditions of this example, and the chromatogram was recorded, and the result is shown in FIG. 3.
Calculating the content of (R) -1, 2-propylene glycol in the test solution by adopting a peak area external standard method, wherein the calculation formula is as follows:
Figure BDA0003141385450000071
wherein:
ASasthe peak area of a solvent to be detected in a test solution;
CSSconcentration of the solvent to be detected in the standard solution is mg/mL;
ASSthe peak area of a solvent to be detected in the standard solution;
CSasmg/mL, concentration of sample in the test solution.
We have performed a method validation of the above method with the following items: LOQ (limit of quantitation) & LOD (limit of detection), linearity, repeatability and intermediate precision, accuracy, the verification results were as follows:
TABLE 3 quantitation and detection limit results for (R) -1, 2-propanediol
Figure BDA0003141385450000072
And (4) conclusion: as can be seen from Table 3, the limit of quantitation of the impurity (R) -1, 2-propanediol is about 0.02%, the limit of detection is about 0.006%, and the method has a high sensitivity.
TABLE 4 Linear results for (R) -1, 2-propanediol
Figure BDA0003141385450000073
Figure BDA0003141385450000081
And (4) conclusion: from table 4, it can be seen that the impurity (R) -1, 2-propanediol, at the limit concentration of LOQ% to 200%, has good linear correlation, and has an intercept of not more than 10% of the 100% response value, within an acceptable range, meeting the specification.
TABLE 5 repeatability and intermediate precision results for (R) -1, 2-propanediol in (S) -1, 2-propanediol
Figure BDA0003141385450000082
And (4) conclusion: the repeatability of the (R) -1, 2-propanediol content in 6 sample solutions was within acceptable limits (< 5%); the results of intermediate precision of the (R) -1, 2-propanediol content in 12 sample solutions were within acceptable limits (< 5%), so the method had good reproducibility and intermediate precision.
TABLE 6 results of normalized recovery of (R) -1, 2-propanediol from (S) -1, 2-propanediol
Figure BDA0003141385450000083
Figure BDA0003141385450000091
And (4) conclusion: as can be seen from Table 6, the recovery rate of the impurity (R) -1, 2-propanediol is about 92.64% -104.50% at the limit concentration of 40% -150%, and is within the range of 80% -120% of the acceptable range standard, which meets the specification.
From the results of examples 1 and 2, the method has high specificity, sensitivity, linearity and accuracy and precision, and can accurately measure the content of enantiomer (R) -1, 2-propanediol in (S) -1, 2-propanediol.
In addition, the method is also applicable to the chromatographic conditions in the embodiment, such as changing to detecting (R) -1, 2-propanediol or isomer (S) -1, 2-propanediol in dapagliflozin bulk drugs and preparations.
Example 3 this comparative example was tested in a conventional test format with the following steps:
-an instrument: an Agilent 7890A gas chromatograph and workstation thereof, an FID detector and an autosampler;
SUPELCO Gama DEX (30 m. times.0.25 mm. 0.25 μm)
-a carrier gas; nitrogen gas
-flow rate: 0.75mL/min
-split ratio: 35:1
Column temperature: the initial temperature was 40 ℃ and held for 5 minutes, and the temperature was raised to 100 ℃ at a rate of 3 ℃/min and held for 10 minutes.
-injection port temperature: 200 deg.C
Detector temperature: 250 deg.C
-air flow rate: 400mL/min
-hydrogen flow rate: 40mL/min
-purge gas: nitrogen gas
-purge gas flow rate: 25mL/min
-volume of sample injection: 0.5. mu.L
Solution preparation:
diluent agent: methylene dichloride
Blank solution: methylene dichloride
Accurately weighing about 25mg of (S) -1, 2-propylene glycol reference substance, placing the reference substance in a 25mL volumetric flask, adding a proper amount of dichloromethane to dissolve the reference substance, and fixing the volume to the scale. 2mL of the solution was precisely transferred, placed in a 20mL volumetric flask, diluted with dichloromethane and fixed to the volume to the mark to be used as a standard solution of (S) -1, 2-propanediol.
Accurately weighing about 25mg of (R) -1, 2-propylene glycol reference substance, placing the reference substance in a 25mL volumetric flask, adding a proper amount of dichloromethane to dissolve the reference substance, and fixing the volume to the scale. Precisely transferring 2mL of the solution, placing the solution in a 20mL volumetric flask, diluting the solution with dichloromethane and fixing the volume to the scale mark to obtain a standard solution of (R) -1, 2-propylene glycol.
As can be seen from FIGS. 5 and 6, the chromatographic peak tails of (S) -1, 2-propanediol and (R) -1, 2-propanediol were severe, (S) -1, 2-propanediol retention time was 23.150min, and (R) -1, 2-propanediol retention time was 23.239min, which were completely overlapped and could not be separated at all.
Comparative example
The detection method of CN105738533B is adopted to detect the S-1, 2-propylene glycol.
Precisely weighing about 100mg of 1, 2-propylene glycol, placing the weighed 1, 2-propylene glycol into a 10ml measuring flask, adding acetone for dissolving and diluting to scale, shaking up, precisely weighing 5ml, placing the weighed 1, 2-propylene glycol into a micro-reactor, adding 0.5g of a water removal agent (4A molecular sieve) and 10mg of a catalyst (Amberlyst-15), sealing, stirring for 1h at room temperature, filtering a reaction solution by using 0.45 mu m, and taking a filtrate as a sample solution.
Gas phase detection conditions: shimadzu gas chromatograph (GC-2010) and Lab Solutions workstation; automatic sample introduction; CDChirasil-DEX CB (0.25 μm, 25m × 0.25 μm) was used as an analytical column; the detector is a hydrogen flame ion detector; the initial temperature is 60 ℃, the temperature is maintained for 10 minutes, the temperature is raised to 150 ℃ at the rate of 40 ℃ per minute, and the temperature is maintained for 5 minutes; the temperature of a sample inlet is 250 ℃, and the split ratio is 50: 1; the temperature of the detector is 250 ℃; the carrier gas was nitrogen, the flow rate was 1.0ml per minute, and the injection volume was 1. mu.L.
As a result, the chromatographic peaks having retention times of 5.854 minutes and 6.412 minutes were found to be the (R) -1, 2-propanediol derived product and the (S) -1, 2-propanediol derived product, respectively, and the degree of separation was 3.5.
The above description of the embodiments is only for the purpose of assisting understanding of the method of the present invention and the core idea thereof, and it should be noted that those skilled in the art can make several improvements and modifications to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall into the protection scope of the claims of the present invention.

Claims (10)

1. A method for detecting 1,2-propanediol enantiomer, comprising: adding a derivatization reagent and a catalyst into a sample containing the 1, 2-propylene glycol enantiomer, performing derivatization, adding a diluent for dilution to obtain a test solution, and performing quantitative analysis according to a gas chromatography; the derivatization reagent is: an organic acid anhydride reagent.
2. The method for detecting the 1,2-propanediol enantiomer of claim 1, wherein the organic acid anhydride reagent is a C1-C8 lower chain acid anhydride.
3. The method for detecting the enantiomers of 1,2-propanediol according to claim 1, wherein said derivatizing reagent is selected from the group consisting of: one or more of formic anhydride, acetic anhydride, propionic anhydride, and butyric anhydride.
4. The method for detecting 1,2-propanediol enantiomer of claim 1-3, wherein the catalyst is selected from one or more of sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid.
5. The method for detecting the enantiomer of 1,2-propanediol according to claim 1 to 3, wherein the diluent is dichloromethane.
6. The method for detecting the 1,2-propanediol enantiomer of claim 1-3, wherein the molar ratio of the sample containing the 1,2-propanediol enantiomer to the derivatizing reagent is 1 (2.5-20).
7. The method for detecting the 1,2-propanediol enantiomer of claim 1-4, wherein the molar ratio of the catalyst to the sample containing the 1,2-propanediol enantiomer is (0.05-0.5): 1.
8. The method for detecting the 1,2-propanediol enantiomer of claim 1, wherein the gas chromatography detection conditions are that chemically bonded beta-cyclodextrin is used as a stationary phase, and a hydrogen ion flame detector is used as a detector; the temperature of a sample inlet is 180-300 ℃; the split ratio is 1: 1-100: 1; the temperature of the detector is 200-320 ℃, and the flow rate of nitrogen or helium is 0.1-3.0 mL per minute.
9. The method for detecting the enantiomer of 1,2-propanediol according to claim 8, wherein the column temperature during detection is a temperature programming, and the temperature programming is performed according to the following table:
column temperature (. degree. C.) Retention time (min) Rate of temperature rise (. degree. C./min) 60 5 20 120 0 1 130 0 10 200 10 /
10. The method for detecting the enantiomer of 1,2-propanediol according to claim 8 or 9, wherein the column flow rate is 1.5mL/min and the injection volume is 1 μ L.
CN202110741025.7A 2021-06-30 2021-06-30 Detection method of 1, 2-propylene glycol enantiomer Pending CN113588811A (en)

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