CN115308332B - P-nitrophenyl-beta-hydroxyethyl sulfide and impurity content detection method thereof - Google Patents
P-nitrophenyl-beta-hydroxyethyl sulfide and impurity content detection method thereof Download PDFInfo
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- 239000012535 impurity Substances 0.000 title claims abstract description 40
- 238000001514 detection method Methods 0.000 title abstract description 20
- WDJLDRBCOKVKBE-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C(CSCC(C1=CC=C(C=C1)[N+](=O)[O-])O)O Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C(CSCC(C1=CC=C(C=C1)[N+](=O)[O-])O)O WDJLDRBCOKVKBE-UHFFFAOYSA-N 0.000 claims abstract description 59
- 239000000523 sample Substances 0.000 claims abstract description 47
- 238000004458 analytical method Methods 0.000 claims abstract description 37
- 239000012488 sample solution Substances 0.000 claims abstract description 24
- 238000010812 external standard method Methods 0.000 claims abstract description 5
- 239000007789 gas Substances 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 239000012159 carrier gas Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 25
- 238000002309 gasification Methods 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 12
- 238000000926 separation method Methods 0.000 description 11
- 239000013558 reference substance Substances 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000011033 desalting Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000012417 linear regression Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- -1 dithiodiethanol Chemical compound 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- 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
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/025—Gas chromatography
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- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses a p-nitrophenyl-beta-hydroxyethyl thioether and an impurity content detection method thereof, which belong to the technical field of detection and analysis, and the p-nitrophenyl-beta-hydroxyethyl thioether and the impurity content detection method thereof comprise the following steps: preparing a sample into a sample solution; injecting the sample solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the content of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof by an external standard method; the gas chromatograph is one of Agilent gas chromatograph 7820A, agilent gas chromatograph 7890A, shimadzu GC-2010Plus and Shimadzu GC-2014C. The detection method disclosed by the invention can be used for effectively detecting the content of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof and the content of dithiodiethanol, and is high in accuracy.
Description
Technical Field
The invention relates to the technical field of detection and analysis, in particular to a method for detecting p-nitrophenyl-beta-hydroxyethyl thioether and impurity content thereof.
Background
P-nitrophenyl-beta-hydroxyethyl sulfide is an important organic synthesis intermediate, and in the process of synthesizing para-esters, four steps of reactions are generally involved: condensation, oxidation, hydrogenation reduction and esterification, p-nitrophenyl-beta-hydroxyethyl sulfide is the main product of the first condensation step, which is accompanied by numerous byproducts (i.e., impurities), such as thiodiglycol, dithiodiethanol, mercaptoethanol, phenol, p-chloronitrobenzene, dimethylformamide and other unknowns.
The content of dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl thioether directly affects the yield and conversion rate of a reaction product, the generation of dithiodiethanol must be strictly controlled, and the prior art does not describe how to measure the content of dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl thioether.
How to accurately detect the content of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof and the content of dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl thioether become technical problems to be solved urgently by the technicians in the field.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for detecting the content of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof, which can effectively detect the content of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
therefore, in a first aspect of the present invention, the present invention provides a method for detecting p-nitrophenyl-beta-hydroxyethyl sulfide and impurity content thereof, comprising the steps of:
preparing a sample into a sample solution;
injecting the sample solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the content of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof by an external standard method;
the gas chromatograph is one of Agilent gas chromatograph 7820A, agilent gas chromatograph 7890A, shimadzu GC-2010Plus and Shimadzu GC-2014C.
As a preferred embodiment of the invention, the gas chromatograph is Shimadzu GC-2014C.
By selecting the gas chromatograph, the peak of the p-nitrophenyl-beta-hydroxyethyl sulfide can be effectively displayed in the obtained chromatogram according to the method, the purity and the separation degree of the peak are good, the interference factor is small, and meanwhile, the impurity peak can be displayed in the chromatogram, so that the content of the p-nitrophenyl-beta-hydroxyethyl sulfide can be effectively detected, and the impurity content of the p-nitrophenyl-beta-hydroxyethyl sulfide can be calculated.
The method can be widely applied to the detection of the content of the p-nitrophenyl-beta-hydroxyethyl sulfide, is particularly suitable for the detection of the content of substances and the content of impurities taking the p-nitrophenyl-beta-hydroxyethyl sulfide as a main component, is particularly suitable for the detection of the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and the content of impurities thereof in the first-step condensation reaction in the four-step synthesis of para-ester, and can fully display the chemical composition information of the obtained product of the first-step condensation reaction.
As a preferred embodiment of the present invention, the sample concentration in the sample solution is 100 to 300mg/kg.
Specifically, the preparation method of the sample solution comprises the following steps: removing solvent from the sample, desalting, and preparing a sample solution with the sample concentration of 100-300 mg/kg by cyclohexane.
The method for removing the solvent comprises at least one of extraction, filtration and distillation; the desalting method is at least one of suction filtration and washing.
Before detection analysis, the p-nitrophenyl-beta-hydroxyethyl thioether has high viscosity and usually contains a certain salt, so that the sample needs to be pretreated, and impurities can be effectively removed, interference factors can be removed, and detection errors can be reduced by pretreatment under the conditions.
As a preferred embodiment of the present invention, the conditions for the analysis by the gas chromatograph are: the chromatographic column is a capillary chromatographic column, the detector is a thermal conductivity cell detector or a hydrogen flame ionization detector, the temperature of the detector is 280-320 ℃, the temperature of the gasification chamber is 200-280 ℃, the carrier gas is nitrogen, hydrogen or helium, the flow rate of the carrier gas is 0.8-4 mL/min, the sample injection amount is 0.3-1.0 mu L, and the split ratio is (10-70): 1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
The inventor of the invention has found out and found in a great deal of research that under the specific analysis conditions, a sample solution is injected into a gas chromatograph, a sample is gasified through a gasification chamber and then enters a chromatographic column for separation, finally, components in the sample sequentially flow out of the chromatographic column according to the boiling point and are displayed on a chromatogram in the form of chromatographic peaks, the obtained chromatogram has high peak purity of p-nitrophenyl-beta-hydroxyethyl sulfide, good peak separation degree and short separation time, the chromatogram fully displays the component information of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof, and the peak area of the p-nitrophenyl-beta-hydroxyethyl sulfide is substituted into a linear regression equation, so that the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof can be measured, and the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof can be accurately detected.
As a preferred embodiment of the present invention, the capillary chromatography column is at least one of OV-1 capillary chromatography column, BP-20 capillary chromatography column, HP-35 capillary chromatography column, DB-1301 capillary chromatography column, and Rtx-200 capillary chromatography column.
As a preferred embodiment of the present invention, the conditions for the analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an OV-1 capillary chromatographic column, the column length is 50m, the column inner diameter is 0.32mm, the film thickness is 0.4 mu m, the column temperature is 60 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 320 ℃, the gasification chamber temperature is 280 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 70:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
In particular, under the above analysis conditions, the detection result is the most accurate.
In a second aspect of the present invention, the present invention provides a method for detecting the content of dithiodiethanol in p-nitrophenyl- β -hydroxyethyl sulfide, comprising the steps of:
preparing a sample into a sample solution;
injecting the sample solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the content of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof by an external standard method;
the gas chromatograph is one of Agilent gas chromatograph 7820A, agilent gas chromatograph 7890A, shimadzu GC-2010Plus and Shimadzu GC-2014C.
By selecting the hue chromatograph and according to the method, the obtained chromatogram can effectively show the peaks of the p-nitrophenyl-beta-hydroxyethyl sulfide and the dithiodiethanol, and the peak purity and the separation degree are good, and the interference factor is small, so that the contents of the p-nitrophenyl-beta-hydroxyethyl sulfide and the dithiodiethanol can be effectively calculated.
The method can be widely applied to the detection of the content of the dithiodiethanol, and is particularly suitable for the content of the dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl thioether, and the method is suitable for the content detection of the dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl thioether in the first condensation reaction.
As a preferred embodiment of the present invention, the sample concentration in the test solution is 500 to 6000mg/kg.
Specifically, the preparation method of the sample solution comprises the following steps: removing solvent from the sample, desalting, and preparing a sample solution with the sample concentration of 500-6000 mg/kg by cyclohexane.
The method for removing the solvent comprises at least one of extraction, filtration and distillation; the desalting method is at least one of suction filtration and washing.
Before detection analysis, the p-nitrophenyl-beta-hydroxyethyl thioether has high viscosity and usually contains a certain salt, so that the sample needs to be pretreated, and impurities can be effectively removed, interference factors can be removed, and detection errors can be reduced by pretreatment under the conditions.
As a preferred embodiment of the present invention, the conditions for the analysis by the gas chromatograph are: the chromatographic column is a capillary chromatographic column, the detector is a thermal conductivity cell detector or a hydrogen flame ionization detector, the temperature of the detector is 250-280 ℃, the temperature of a gasification chamber is 150-230 ℃, carrier gas is nitrogen, hydrogen or helium, the flow rate of the carrier gas is 0.8-1.5 mL/min, the sample injection amount is 0.3-1.0 mu L, and the split ratio is (20-40): 1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
Under the specific analysis conditions, the sample solution to be tested is injected into a gas chromatograph, the sample is gasified through a gasification chamber, then enters a chromatographic column for separation, finally, components in the sample sequentially flow out of the chromatographic column according to the boiling point through a detector, and are displayed on the chromatogram in the form of chromatographic peaks, the peak separation degree of the dithiodiethanol in the obtained chromatogram is good, the separation time is short, and the peak area of the dithiodiethanol is substituted into a linear regression equation, so that the content of the dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl thioether can be measured.
As a preferred embodiment of the present invention, the capillary chromatography column is one of SH-Stabilwax capillary chromatography column, SP-2340 capillary chromatography column, HP-20M capillary chromatography column, SP-2401 capillary chromatography column, inertCap capillary chromatography column.
As a preferred embodiment of the present invention, the conditions for the analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an SH-Stabilwax capillary chromatographic column, the column length is 30m, the column inner diameter is 0.25mm, the film thickness is 0.25 mu m, the column temperature is 120 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 250 ℃, the gasification chamber temperature is 150 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 20:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
The invention has the beneficial effects that: the detection method can effectively detect the content of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof and the content of dithiodiethanol, and has high accuracy; under specific analysis conditions, the sample solution to be tested is injected into a gas chromatograph, the sample is gasified through a gasification chamber and then enters a chromatographic column for separation, finally, components in the sample sequentially flow out of the chromatographic column according to the boiling point through a detector and are displayed on a chromatogram in the form of chromatographic peaks, the obtained chromatogram has high peak purity of p-nitrophenyl-beta-hydroxyethyl sulfide, good peak separation degree and short separation time, the chromatogram fully displays the component information of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof, and the peak area of the p-nitrophenyl-beta-hydroxyethyl sulfide is substituted into a linear regression equation, so that the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof can be measured, and the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof can be accurately detected.
Drawings
FIG. 1 is a chromatogram of a 100mg/kg p-nitrophenyl-beta-hydroxyethyl sulfide control solution;
FIG. 2 is a standard curve of p-nitrophenyl-beta-hydroxyethyl sulfide control;
FIG. 3 is a chromatogram of the sample solution of example 1;
FIG. 4 is a chromatogram of a 160mg/kg dithiodiethanol control solution;
FIG. 5 is a standard curve of a dithiodiethanol control;
FIG. 6 is a chromatogram of the sample solution of example 6.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The reagents or apparatus used in the present invention are conventional products commercially available without the manufacturer's knowledge.
Example 1
A method for detecting p-nitrophenyl-beta-hydroxyethyl thioether and impurity content thereof comprises the following steps:
1. the conditions for the analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an OV-1 capillary chromatographic column, the column length is 50m, the column inner diameter is 0.32mm, the film thickness is 0.4 mu m, the column temperature is 60 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 320 ℃, the gasification chamber temperature is 280 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 70:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
(1) Preparation of a control solution: accurately weighing p-nitrophenyl-beta-hydroxyethyl sulfide standard substances, and preparing 5mg/kg, 10mg/kg, 20mg/kg, 40mg/kg, 60mg/kg, 80mg/kg, 100mg/kg, 200mg/kg, 300mg/kg, 400mg/kg and 500mg/kg of p-nitrophenyl-beta-hydroxyethyl sulfide reference substance solutions by using cyclohexane respectively;
(2) Injecting the reference substance solutions with different concentration gradients in the step (1) into a gas chromatograph, respectively analyzing under the chromatographic conditions, and recording a chromatogram of the reference substance and a peak area, wherein the chromatogram of 100mg/kg of the reference substance is shown as figure 1, the retention time is 15.8min, the peak area is 2002254, and a standard curve equation (figure 2) is calculated according to the peak area of the reference substance solutions with the gradient concentrations;
(3) Preparing a sample solution, distilling a sample, removing impurities by suction, preparing the sample into a concentration of 200mg/kg by using cyclohexane, injecting the sample into a gas chromatograph, analyzing under the chromatographic conditions, sequentially flowing out components in the sample from a chromatographic column according to the boiling point, displaying the components on the chromatogram in the form of chromatographic peaks (as shown in figure 3), and recording the peak area;
(4) And (3) carrying out a standard curve equation, and calculating the content of p-nitrophenyl-beta-hydroxyethyl sulfide, thereby calculating the content of impurities.
Example 2
Example 2 is different from example 1 in that the conditions for analysis by the gas chromatograph of example 2 are different from example 1, and the other are the same.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is BP-20 capillary chromatographic column, the column length is 30m, the column inner diameter is 0.32mm, the film thickness is 0.32 mu m, the column temperature is 180 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 280 ℃, the temperature of the gasification chamber is 220 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 0.8 mu L, and the split ratio is 10:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
Example 3
Example 3 is different from example 1 in that the conditions for analysis by the gas chromatograph of example 3 are different from example 1, and are otherwise identical.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an HP-35 capillary chromatographic column, the column length is 50m, the column inner diameter is 0.25mm, the film thickness is 0.50 mu m, the column temperature is 200 ℃, the detector is a thermal conductivity cell detector, the detector temperature is 280 ℃, the temperature of a gasification chamber is 200 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 4.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 40:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
Example 4
Example 4 differs from example 1 in that the conditions for analysis by the gas chromatograph of example 4 are different from example 1, and are otherwise identical.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is DB-1301 capillary chromatographic column, the column length is 50m, the column inner diameter is 0.32mm, the film thickness is 0.32 mu m, the column temperature is 200 ℃, the detector is a thermal conductivity cell detector, the detector temperature is 280 ℃, the gasification chamber temperature is 250 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 0.3 mu L, and the split ratio is 60:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
Example 5
Example 5 is different from example 1 in that the conditions for analysis by the gas chromatograph of example 5 are different from example 1, and are otherwise identical.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an Rtx-200 capillary chromatographic column, the column length is 30m, the column inner diameter is 0.53mm, the film thickness is 0.32 mu m, the column temperature is 150 ℃, the detector is a thermal conductivity cell detector, the detector temperature is 280 ℃, the temperature of a gasification chamber is 210 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 0.5 mu L, and the split ratio is 70:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
Test example 1
To verify the accuracy of the present invention, p-nitrophenyl-beta-hydroxyethyl sulfide standard (impurity content 1%) having a purity of 99.00 was subjected to content measurement according to the methods described in examples 1 to 5, and the content measurement results are shown in table 1.
TABLE 1
As can be seen from Table 1, the method for detecting the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and the impurity thereof can be widely applied to the determination of the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and the impurity thereof, has high accuracy and has wide application prospect.
Example 6
A method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl thioether comprises the following steps:
1. the conditions for the analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an SH-Stabilwax capillary chromatographic column, the column length is 30m, the column inner diameter is 0.25mm, the film thickness is 0.25 mu m, the column temperature is 120 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 250 ℃, the gasification chamber temperature is 150 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 20:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
(1) Preparation of a control solution: precisely weighing dithio-diethanol standard substance, and respectively preparing reference substance solutions with concentrations of 80mg/kg, 100mg/kg, 120mg/kg, 160mg/kg, 180mg/kg, 200mg/kg, 220mg/kg, 240mg/kg and 280mg/kg by cyclohexane;
(2) Injecting the reference substance solutions with different concentration gradients in the step (1) into a gas chromatograph, respectively analyzing under the chromatographic conditions, and recording a chromatogram of the reference substance and a peak area, wherein the chromatogram of 160mg/kg of the reference substance is shown as figure 4, the retention time is 14.58min, the peak area is 1433, and a standard curve equation (figure 5) is calculated according to the peak area of the reference substance solutions with the gradient concentrations;
(3) Preparing a sample solution, distilling a sample, removing impurities by suction, preparing the sample into 5000mg/kg with cyclohexane, injecting the sample into a gas chromatograph, analyzing under the chromatographic conditions, sequentially flowing out of a chromatographic column according to the boiling point of the components in the sample, displaying the components on the chromatogram in the form of chromatographic peaks (as shown in figure 6), and recording the peak area;
(4) And (3) carrying out a standard curve equation, and calculating the content of dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl sulfide.
Example 7
Example 7 is different from example 6 in that the conditions for analysis by the gas chromatograph of example 7 are different from example 6, and the other are the same.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an SP-2340 capillary chromatographic column, the column length is 30m, the column inner diameter is 0.32mm, the film thickness is 0.5 mu m, the column temperature is 180 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 250 ℃, the gasification chamber temperature is 200 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 0.8 mu L, and the split ratio is 30:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
Example 8
Example 8 differs from example 6 in that the conditions for analysis by the gas chromatograph of example 8 are different from those of example 1, and are otherwise identical.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an HP-20M capillary chromatographic column, the column length is 30M, the column inner diameter is 0.32mm, the film thickness is 0.5 mu M, the column temperature is 160 ℃, the detector is a thermal conductivity cell detector, the detector temperature is 250 ℃, the temperature of a gasification chamber is 200 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 40:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
Example 9
Example 9 is different from example 6 in that the conditions for analysis by the gas chromatograph of example 9 are different from those of example 1, and the other are the same.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an SP-2401 capillary chromatographic column, the column length is 50m, the column inner diameter is 0.32mm, the film thickness is 1.0 mu m, the column temperature is 200 ℃, the detector is a thermal conductivity cell detector, the detector temperature is 280 ℃, the temperature of a gasification chamber is 230 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 0.3 mu L, and the split ratio is 20:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
Example 10
Example 10 is different from example 6 in that the conditions for analysis by the gas chromatograph of example 10 are different from those of example 1, and the other are the same.
In this embodiment, the conditions for analysis by the gas chromatograph are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an InertCap capillary chromatographic column, the column length is 30m, the column inner diameter is 0.53mm, the film thickness is 1.0 mu m, the column temperature is 150 ℃, the detector is a thermal conductivity cell detector, the detector temperature is 280 ℃, the temperature of a gasification chamber is 220 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 0.5 mu L, and the split ratio is 20:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
Test example 2
In order to verify the accuracy of the present invention, a dithiodiethanol standard having a purity of 99.00 (impurity content 1%) was subjected to content measurement according to the methods described in examples 6 to 10, and the content measurement results are shown in table 1.
TABLE 1
As can be seen from Table 1, the detection of the invention can be applied to the detection of the content of dithiodiethanol, has high accuracy and wide application prospect.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made to the technical solution of the present invention without departing from the spirit and scope of the technical solution of the present invention.
Claims (6)
1. The method for detecting the content of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof is characterized by comprising the following steps of:
preparing a sample into a sample solution;
injecting the sample solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the content of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof by an external standard method;
the gas chromatograph is one of Agilent gas chromatograph 7820A, agilent gas chromatograph 7890A, shimadzu GC-2010Plus and Shimadzu GC-2014C;
the conditions for the analysis by the gas chromatograph are: the chromatographic column is a capillary chromatographic column, the detector is a thermal conductivity cell detector or a hydrogen flame ionization detector, the temperature of the detector is 280-320 ℃, the temperature of the gasification chamber is 200-280 ℃, the carrier gas is nitrogen, hydrogen or helium, the flow rate of the carrier gas is 0.8-4 mL/min, the sample injection amount is 0.3-1.0 mu L, and the split ratio is (10-70): 1, a step of;
heating program: the initial temperature is 60 ℃, the temperature is increased to 280 ℃ at 5 ℃/min, the temperature is kept for 5min, the temperature is increased to 300 ℃ at 10 ℃/min, and the temperature is kept for 8min;
the impurity is dithiodiethanol.
2. The method for detecting p-nitrophenyl-beta-hydroxyethyl sulfide and the impurity content thereof according to claim 1, wherein the concentration of the sample in the sample solution is 100-300 mg/kg.
3. The method for detecting the content of impurities in p-nitrophenyl-beta-hydroxyethyl sulfide according to claim 1, wherein the gas chromatograph analyzes the following conditions: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an OV-1 capillary chromatographic column, the column length is 50m, the column inner diameter is 0.32mm, the film thickness is 0.4 mu m, the column temperature is 60 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 320 ℃, the gasification chamber temperature is 280 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 70:1, a step of;
heating program: the initial temperature was 60℃and was kept at 5℃/min to 280℃for 5min and at 10℃/min to 300℃for 8min.
4. The method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl thioether is characterized by comprising the following steps of:
preparing a sample into a sample solution;
injecting the sample solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the content of dithiodiethanol in the p-nitrophenyl-beta-hydroxyethyl sulfide by an external standard method;
the gas chromatograph is one of Agilent gas chromatograph 7820A, agilent gas chromatograph 7890A, shimadzu GC-2010Plus and Shimadzu GC-2014C;
the chromatographic column is a capillary chromatographic column, the detector is a thermal conductivity cell detector or a hydrogen flame ionization detector, the temperature of the detector is 250-280 ℃, the temperature of a gasification chamber is 150-230 ℃, carrier gas is nitrogen, hydrogen or helium, the flow rate of the carrier gas is 0.8-1.5 mL/min, the sample injection amount is 0.3-1.0 mu L, and the split ratio is (20-40): 1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
5. The method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide according to claim 4, wherein the concentration of the sample in the sample solution is 500-6000 mg/kg.
6. The method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide according to claim 5, wherein the conditions for analysis by the gas chromatograph are as follows: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is an SH-Stabilwax capillary chromatographic column, the column length is 30m, the column inner diameter is 0.25mm, the film thickness is 0.25 mu m, the column temperature is 120 ℃, the detector is a hydrogen flame ionization detector, the detector temperature is 250 ℃, the gasification chamber temperature is 150 ℃, the carrier gas is nitrogen, the carrier gas flow rate is 1.0mL/min, the sample injection amount is 1.0 mu L, and the split ratio is 20:1, a step of;
heating program: the initial temperature was 60℃and was raised to 120℃at 5℃per minute for 5min, and then to 230℃at 10℃per minute for 8min.
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| JP2000304736A (en) * | 1999-04-20 | 2000-11-02 | Kawasaki Steel Corp | Quick analytical method for organic compound in stainless steel sulfuric acid pickle |
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| JP2020184068A (en) * | 2020-04-13 | 2020-11-12 | 三井化学株式会社 | Thiol-containing composition for optical material, polymerizable composition for optical material |
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| JP2000304736A (en) * | 1999-04-20 | 2000-11-02 | Kawasaki Steel Corp | Quick analytical method for organic compound in stainless steel sulfuric acid pickle |
| CN107739323A (en) * | 2017-10-10 | 2018-02-27 | 宿迁远扬生物科技有限公司 | A kind of method for preparing p-Aminophenyl-β-hydroxyethyl sulfone sulfate |
| JP2020184068A (en) * | 2020-04-13 | 2020-11-12 | 三井化学株式会社 | Thiol-containing composition for optical material, polymerizable composition for optical material |
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