CN115308332A - 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 42
- 238000001514 detection method Methods 0.000 title abstract description 11
- 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 65
- 238000000034 method Methods 0.000 claims abstract description 50
- 238000004458 analytical method Methods 0.000 claims abstract description 39
- 239000012085 test solution Substances 0.000 claims abstract description 16
- 238000010812 external standard method Methods 0.000 claims abstract description 5
- 239000007789 gas Substances 0.000 claims description 65
- 239000000523 sample Substances 0.000 claims description 46
- 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
- 238000002309 gasification Methods 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 230000000630 rising effect Effects 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 239000012488 sample solution Substances 0.000 claims description 9
- 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
- 238000004587 chromatography analysis Methods 0.000 claims 12
- 239000000243 solution Substances 0.000 description 15
- 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
- 238000006482 condensation reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000001914 filtration 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000011033 desalting Methods 0.000 description 3
- 238000012417 linear regression Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PWHHOXIZSHCFSH-UHFFFAOYSA-N 2-(2-hydroxy-2-nitro-2-phenylethyl)sulfanyl-1-nitro-1-phenylethanol Chemical compound C=1C=CC=CC=1C([N+]([O-])=O)(O)CSCC(O)([N+]([O-])=O)C1=CC=CC=C1 PWHHOXIZSHCFSH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000000967 suction filtration 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
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- 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
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006467 substitution reaction Methods 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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- 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
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- G—PHYSICS
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- 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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Abstract
The invention discloses a method for detecting p-nitrophenyl-beta-hydroxyethyl sulfide and impurity content thereof, belonging to the technical field of detection and analysis, and the method for detecting the p-nitrophenyl-beta-hydroxyethyl sulfide and impurity content thereof comprises the following steps: preparing a sample into a test solution; injecting the test solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the contents 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 provided by the invention can effectively detect the contents of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof and the content of dithiodiethanol, and has high accuracy.
Description
Technical Field
The invention relates to the technical field of detection and analysis, and particularly relates to p-nitrophenyl-beta-hydroxyethyl sulfide and a method for detecting the content of impurities in the p-nitrophenyl-beta-hydroxyethyl sulfide.
Background
P-nitrophenyl- β -hydroxyethyl sulfide is an important organic synthesis intermediate, and in the synthesis of para-esters, four-step reactions are usually involved: the p-nitrophenyl-beta-hydroxyethyl sulfide is a main product of a first condensation reaction, and the first condensation reaction is accompanied by numerous byproducts (i.e., impurities), such as thiodiglycol, dithiodiethanol, mercaptoethanol, phenol, p-chloronitrobenzene, dimethylformamide and other unknown substances.
The content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide directly affects the yield and conversion rate of reaction products, the generation of dithiodiethanol must be strictly controlled, and the prior art does not describe how to measure the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide.
How to accurately detect the contents of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof and the content of dithiodiethanol in the nitrophenyl-beta-hydroxyethyl sulfide becomes a technical problem to be solved by the technical personnel 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 sulfide and impurities thereof, which can effectively detect the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
therefore, in the first aspect of the invention, the invention provides a p-nitrophenyl-beta-hydroxyethyl sulfide and a method for detecting the impurity content thereof, comprising the following steps:
preparing a sample into a test solution;
injecting the test solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the contents 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.
The gas chromatograph is selected and the method is adopted, so that the obtained chromatogram can effectively display the peak of the p-nitrophenyl-beta-hydroxyethyl sulfide, the peak purity and the separation degree are good, the interference factor is small, meanwhile, the impurity peak can be displayed in the chromatogram, the content of the p-nitrophenyl-beta-hydroxyethyl sulfide can be effectively detected, and the content of the impurity can be calculated.
The method can be widely applied to detecting the content of the p-nitrophenyl-beta-hydroxyethyl sulfide, is particularly suitable for detecting the content of substances taking the p-nitrophenyl-beta-hydroxyethyl sulfide as a main component and the content of impurities, is particularly suitable for detecting the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and the impurities thereof in the first step of condensation reaction in the synthesis of the para-ester by the four-step method, and can fully display the chemical component information of the products obtained in the first step of condensation reaction.
As a preferred embodiment of the present invention, the sample concentration in the test solution is 100 to 300mg/kg.
Specifically, the preparation method of the test solution comprises the following steps: removing the solvent from the sample, desalting, and preparing a sample solution with the sample concentration of 100-300 mg/kg by using cyclohexane.
The solvent removing method is at least one of extraction, filtration and distillation; the desalting method comprises at least one of suction filtration and washing.
Before detection and analysis, the p-nitrophenyl-beta-hydroxyethyl sulfide has high viscosity and usually contains a certain amount of salt, so that a sample needs to be pretreated, and the pretreatment under the above conditions can effectively remove impurities, remove interference factors and reduce detection errors.
As a preferred embodiment of the present invention, the conditions for the gas chromatograph analysis 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
The inventor of the present invention has searched and found in a great deal of research, and under the above specific analysis conditions, a sample solution is injected into a gas chromatograph, a sample is gasified by a gasification chamber, and then enters a chromatographic column for separation, and finally components in the sample sequentially flow out of the chromatographic column according to the boiling point and are displayed on a chromatogram in a form of a chromatographic peak, the peak purity of p-nitrophenyl-beta-hydroxyethyl sulfide in the obtained chromatogram is high, the peak separation degree is good, the separation time is short, the chromatogram sufficiently shows 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 determination of the p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof can be performed, 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 chromatographic column is at least one of OV-1 capillary chromatographic column, BP-20 capillary chromatographic column, HP-35 capillary chromatographic column, DB-1301 capillary chromatographic column and Rtx-200 capillary chromatographic column.
As a preferred embodiment of the present invention, the conditions for the gas chromatograph analysis 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
Particularly, under the above analysis conditions, the detection result is most accurate.
In a second aspect of the invention, the invention provides a method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide, which comprises the following steps:
preparing a sample into a test solution;
injecting the test solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the contents 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 chromatogram obtained by selecting the color chromatograph and the method can effectively display the peaks of the p-nitrophenyl-beta-hydroxyethyl sulfide and the dithiodiethanol, and has good peak purity and separation degree and small interference factors, so that the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and the dithiodiethanol can be effectively calculated.
The method can be widely applied to detecting the content of dithiodiethanol, is particularly suitable for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide, and is suitable for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide in the first-step 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 test solution comprises the following steps: removing the solvent and the salt from the sample, and preparing the sample solution with the sample concentration of 500-6000 mg/kg by using cyclohexane.
The solvent removing method comprises at least one of extraction, filtration and distillation; the desalting method comprises at least one of suction filtration and washing.
Before detection and analysis, because the viscosity of the p-nitrophenyl-beta-hydroxyethyl sulfide is high and the p-nitrophenyl-beta-hydroxyethyl sulfide usually contains a certain salt, a sample needs to be pretreated, and the pretreatment under the above conditions can effectively remove impurities, remove interference factors and reduce detection errors.
As a preferred embodiment of the present invention, the conditions for the gas chromatograph analysis 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 the gasification chamber is 150-230 ℃, the 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-flow ratio is (20-40): 1;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 120 deg.C, and maintained for 5min, and 10 deg.C/min to 230 deg.C, and maintained for 8min.
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 the chromatogram in a chromatographic peak form through a detector, the peak separation degree of dithiodiethanol in the obtained chromatogram is good, the separation time is short, and the peak area of dithiodiethanol is substituted into a linear regression equation, so that the content of dithiodiethanol in nitrophenyl-beta-hydroxyethyl sulfide can be measured.
As a preferred embodiment of the invention, the capillary chromatographic column is one of SH-Stabilwax capillary chromatographic column, SP-2340 capillary chromatographic column, HP-20M capillary chromatographic column, SP-2401 capillary chromatographic column and InertCap capillary chromatographic column.
As a preferred embodiment of the present invention, the conditions for the gas chromatograph analysis 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 feeding amount is 1.0 mu L, and the split ratio is 20:1;
temperature rising procedure: the initial temperature is 60 deg.C, and is increased to 120 deg.C at 5 deg.C/min, and maintained for 5min, and is increased to 230 deg.C at 10 deg.C/min, and maintained for 8min.
The invention has the beneficial effects that: the detection method can effectively detect the contents of p-nitrophenyl-beta-hydroxyethyl thioether and impurities thereof and the content of dithiodiethanol, and has high accuracy; according to the method, under a specific analysis condition, a sample solution is injected into a gas chromatograph, a sample is gasified through a gasification chamber, then enters a chromatographic column for separation, finally passes through a detector, components in the sample sequentially flow out of the chromatographic column according to the boiling point and are displayed on a chromatogram in a chromatographic peak form, the peak purity of p-nitrophenyl-beta-hydroxyethyl sulfide in the obtained chromatogram is high, the peak separation degree is good, the separation time is short, the chromatogram fully shows 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 the impurities thereof can be determined, and the content of the p-nitrophenyl-beta-hydroxyethyl sulfide and the 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 test solution of example 1;
FIG. 4 is a chromatogram of a 160mg/kg dithiodiethanol control solution;
FIG. 5 is a standard curve for dithiodiethanol control;
FIG. 6 is a chromatogram of the test solution of example 6.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are some, but not all embodiments of the present invention. All other embodiments, which can be obtained by a person skilled in the art without inventive step based on the embodiments of the present invention, are within the scope of protection of the present invention.
The reagents or instruments used in the present invention are conventional products which are commercially available, and manufacturers are not indicated.
Example 1
A method for detecting p-nitrophenyl-beta-hydroxyethyl sulfide and impurity content thereof comprises the following steps:
1. the analysis conditions of the gas chromatograph are as follows: the gas chromatograph is an 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
(1) Preparation of control solutions: accurately weighing p-nitrophenyl-beta-hydroxyethyl thioether standard substances, and preparing into p-nitrophenyl-beta-hydroxyethyl thioether reference substance solutions with the concentrations of 5mg/kg, 10mg/kg, 20mg/kg, 40mg/kg, 60mg/kg, 80mg/kg, 100mg/kg, 200mg/kg, 300mg/kg, 400mg/kg and 500mg/kg by using cyclohexane respectively;
(2) Injecting the reference substance solutions with different concentration gradients in the step (1) into a gas chromatograph, analyzing under the chromatographic conditions, respectively, recording a chromatogram and a peak area of the reference substance, wherein the chromatogram of the reference substance with 100mg/kg is shown in fig. 1, the retention time of the chromatogram is 15.8min, the peak area is 2002254, and calculating a standard curve equation (fig. 2) according to the peak area of the reference substance solution with the gradient concentration;
(3) Preparing a sample solution, distilling and filtering a sample to remove impurities, preparing the sample into a concentration of 200mg/kg with cyclohexane, injecting the sample into a gas chromatograph, analyzing under the chromatographic conditions, enabling components in the sample to sequentially flow out of a chromatographic column according to the boiling point, displaying the components on a chromatogram in a chromatogram (as shown in figure 3) in a chromatogram peak mode, and recording the peak area;
(4) And (4) putting the p-nitrophenyl-beta-hydroxyethyl sulfide into a standard curve equation, and calculating the content of the p-nitrophenyl-beta-hydroxyethyl sulfide so as to calculate the content of impurities.
Example 2
Example 2 is different from example 1 in that the gas chromatograph analysis conditions of example 2 are different from those of example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis are: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is a 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 gasification chamber temperature 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
Example 3
Example 3 is different from example 1 in that the gas chromatograph analysis conditions of example 3 are different from those of example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis are as follows: the gas chromatograph is an 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 gasification chamber temperature 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
Example 4
Example 4 is different from example 1 in that the gas chromatograph analysis conditions of example 4 are different from those of example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis are as follows: the gas chromatograph is Shimadzu GC-2014C, the chromatographic column is a 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
Example 5
Example 5 is different from example 1 in that the gas chromatograph analysis conditions of example 5 are different from those of example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis 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 gasification chamber temperature 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
Test example 1
In order to verify the accuracy of the present invention, the p-nitrophenyl- β -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 p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof can be widely applied to the determination of the content of p-nitrophenyl-beta-hydroxyethyl sulfide and impurities thereof, and has high accuracy and wide application prospect.
Example 6
A method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide comprises the following steps:
1. the analysis conditions of 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 feeding amount is 1.0 mu L, and the split ratio is 20:1;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 120 deg.C, and maintained for 5min, and 10 deg.C/min to 230 deg.C, and maintained for 8min.
(1) Preparation of control solutions: precisely weighing dithiodiethanol standard substances, and preparing reference substance solutions with the concentrations of 80mg/kg, 100mg/kg, 120mg/kg, 160mg/kg, 180mg/kg, 200mg/kg, 220mg/kg, 240mg/kg and 280mg/kg by using cyclohexane respectively;
(2) Injecting the reference substance solutions with different concentration gradients in the step (1) into a gas chromatograph, analyzing under the chromatographic conditions, respectively, recording the chromatogram and the peak area of the reference substance, wherein the chromatogram of the reference substance 160mg/kg is shown in fig. 4, the retention time of the chromatogram is 14.58min, the peak area is 1433, and calculating a standard curve equation (fig. 5) according to the peak area of the reference substance solution with the gradient concentration;
(3) Preparing a sample solution, distilling and filtering a sample to remove impurities, preparing the sample into a concentration of 5000mg/kg with cyclohexane, injecting the sample into a gas chromatograph, analyzing under the chromatographic conditions, enabling components in the sample to sequentially flow out of a chromatographic column according to the boiling point, displaying the components on a chromatogram in a chromatogram (as shown in figure 6) in a form of a chromatographic peak, and recording the peak area;
(4) And (4) putting the p-nitrophenyl-beta-hydroxyethyl sulfide into 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 gas chromatograph analysis conditions in example 7 are different from those in example 6, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis 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, the split ratio is 30:1;
temperature rising procedure: the initial temperature is 60 deg.C, and is increased to 120 deg.C at 5 deg.C/min, and maintained for 5min, and is increased to 230 deg.C at 10 deg.C/min, and maintained for 8min.
Example 8
Example 8 is different from example 6 in that the gas chromatograph analysis conditions of example 8 are different from those of example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis are as follows: 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 gasification chamber temperature 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;
temperature rising procedure: the initial temperature is 60 deg.C, and is increased to 120 deg.C at 5 deg.C/min, and maintained for 5min, and is increased to 230 deg.C at 10 deg.C/min, and maintained for 8min.
Example 9
Example 9 is different from example 6 in that the conditions for gas chromatograph analysis in example 9 are different from those in example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis are as follows: 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 gasification chamber temperature 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;
temperature rising procedure: the initial temperature is 60 deg.C, and is increased to 120 deg.C at 5 deg.C/min, and maintained for 5min, and is increased to 230 deg.C at 10 deg.C/min, and maintained for 8min.
Example 10
Example 10 is different from example 6 in that the gas chromatograph analysis conditions of example 10 are different from those of example 1, and the other conditions are the same.
In this embodiment, the conditions of the gas chromatograph analysis are as follows: 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 gasification chamber temperature 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;
temperature rising procedure: the initial temperature is 60 deg.C, and is increased to 120 deg.C at 5 deg.C/min, and maintained for 5min, and is increased to 230 deg.C at 10 deg.C/min, and maintained for 8min.
Test example 2
In order to verify the accuracy of the present invention, dithiodiethanol standard (impurity content 1%) with a purity of 99.00 was subjected to content measurement by the method 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 method can be applied to detecting the content of dithiodiethanol, and has high accuracy and wide application prospect.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is 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 on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. A method for detecting p-nitrophenyl-beta-hydroxyethyl sulfide and impurity content thereof is characterized by comprising the following steps:
preparing a sample into a test solution;
injecting the test solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the contents 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.
2. The method for detecting p-nitrophenyl- β -hydroxyethyl sulfide and impurity content thereof according to claim 1, wherein the sample concentration in the sample solution is 100 to 300mg/kg.
3. The method for detecting p-nitrophenyl- β -hydroxyethyl sulfide and impurity content thereof according to claim 1, wherein the conditions for the gas chromatograph analysis 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
4. The method for detecting p-nitrophenyl- β -hydroxyethyl sulfide and impurity content thereof according to claim 3, wherein the capillary chromatography column is at least one of an OV-1 capillary chromatography column, a BP-20 capillary chromatography column, an HP-35 capillary chromatography column, a DB-1301 capillary chromatography column, and an Rtx-200 capillary chromatography column.
5. The method for detecting p-nitrophenyl- β -hydroxyethyl sulfide and impurity content thereof according to claim 4, wherein the gas chromatograph analysis conditions 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;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 280 deg.C, holding for 5min, 10 deg.C/min to 300 deg.C, and holding for 8min.
6. A method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide is characterized by comprising the following steps:
preparing a sample into a test solution;
injecting the test solution into a gas chromatograph for analysis to obtain a chromatogram, and calculating the contents 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.
7. The method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide according to claim 6, wherein a sample concentration in the sample solution is 500 to 6000mg/kg.
8. The method for detecting the content of dithiodiethanol in p-nitrophenyl- β -hydroxyethyl sulfide according to claim 6, wherein the conditions for the gas chromatograph analysis 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 the gasification chamber is 150-230 ℃, the 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;
temperature rising procedure: the initial temperature is 60 deg.C, and is increased to 120 deg.C at 5 deg.C/min, and maintained for 5min, and is increased to 230 deg.C at 10 deg.C/min, and maintained for 8min.
9. The method for detecting the content of dithiodiethanol in p-nitrophenyl-beta-hydroxyethyl sulfide according to claim 8, wherein the capillary chromatography column is one of an SH-Stabilwax capillary chromatography column, an SP-2340 capillary chromatography column, an HP-20M capillary chromatography column, an SP-2401 capillary chromatography column, and an InertCap capillary chromatography column.
10. The method for detecting the content of dithiodiethanol in p-nitrophenyl- β -hydroxyethyl sulfide according to claim 9, wherein the conditions for the gas chromatograph analysis 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 feeding amount is 1.0 mu L, and the split ratio is 20:1;
temperature rising procedure: the initial temperature is 60 deg.C, 5 deg.C/min to 120 deg.C, and maintained for 5min, and 10 deg.C/min to 230 deg.C, and maintained for 8min.
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