CN115112795B - HPLC-UV detection method for purity of disodium sulfosuccinate intermediate - Google Patents
HPLC-UV detection method for purity of disodium sulfosuccinate intermediate Download PDFInfo
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- CN115112795B CN115112795B CN202210741371.XA CN202210741371A CN115112795B CN 115112795 B CN115112795 B CN 115112795B CN 202210741371 A CN202210741371 A CN 202210741371A CN 115112795 B CN115112795 B CN 115112795B
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- disodium sulfosuccinate
- acetonitrile
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- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 title claims abstract description 44
- 238000000825 ultraviolet detection Methods 0.000 title claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 22
- 239000012488 sample solution Substances 0.000 claims abstract description 12
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005695 Ammonium acetate Substances 0.000 claims abstract description 9
- 229940043376 ammonium acetate Drugs 0.000 claims abstract description 9
- 235000019257 ammonium acetate Nutrition 0.000 claims abstract description 9
- 238000010828 elution Methods 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 238000001514 detection method Methods 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 239000000523 sample Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- YRIDFQASBDRMBJ-UHFFFAOYSA-N undec-10-enamide Chemical compound NC(=O)CCCCCCCCC=C YRIDFQASBDRMBJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000014759 maintenance of location Effects 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000000337 buffer salt Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 46
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SWELIMKTDYHAOY-UHFFFAOYSA-N 2,4-diamino-6-hydroxypyrimidine Chemical compound NC1=CC(=O)N=C(N)N1 SWELIMKTDYHAOY-UHFFFAOYSA-N 0.000 description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 description 3
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
-
- 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
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/36—Control of physical parameters of the fluid carrier in high pressure liquid systems
-
- 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
- G01N30/50—Conditioning of the sorbent material or stationary liquid
- G01N30/52—Physical parameters
- G01N30/54—Temperature
-
- 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
- G01N30/60—Construction of the column
- G01N30/6052—Construction of the column body
-
- 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
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
Abstract
The invention discloses an HPLC-UV detection method for the purity of disodium sulfosuccinate intermediate, which comprises the steps of taking a proper amount of disodium sulfosuccinate intermediate, dissolving with ACN as a diluent to prepare a sample solution with the concentration of about 1mg/mL, taking 10 mu L of the sample solution, and injecting the sample solution into a liquid chromatograph to detect the purity of main components and related substances; the method adopts a C8 chromatographic column with better retention of the medium polar compound and an ammonium acetate aqueous solution/acetonitrile reversed phase buffer salt chromatographic system, so that the retention of the target compound can be enhanced; the gradient elution is used for separation, so that the purity of the disodium sulfosuccinate intermediate can be rapidly detected, the main component and related substances thereof can be effectively separated, and the reaction of the disodium sulfosuccinate intermediate can be monitored.
Description
Technical Field
The invention belongs to a high performance liquid chromatography (High Performance Liquid Chromatography, HPLC) method, in particular to a method for detecting related substances and purity of disodium sulfosuccinate intermediate by using HPLC.
Background
Undecylenamide MEA-disodium sulfosuccinate is a chemical auxiliary agent used as a surfactant and has a bactericidal effect.
Undecylenamide MEA-disodium sulfosuccinate having the formulaIts molecular formula is C 17 H 27 NNa 2 O 8 S, chemical name of Disodium 4- [2- [ (1-oxoudec-10-enyl) amino ]]ethyl]2-sulfophosphate, the purity of its intermediates and the content of the relevant substances which may be present are DMF, maleic anhydride, need to be controlled during the production process.
Therefore, the separation of the undecylenamide MEA-disodium sulfosuccinate intermediate from the related substances is of great importance for controlling the reaction in the production process.
Disclosure of Invention
The invention aims to provide an HPLC-UV method for detecting the purity of key intermediates, the content of related substances and the residual quantity of solvents in the process of preparing disodium sulfosuccinate starting materials.
The technical scheme adopted for solving the technical problems is as follows: an HPLC-UV detection method for the purity of disodium sulfosuccinate intermediate, the detection conditions are as follows: chromatographic column: dikma Diamonsil C8, 150 x 4.6mm,5 μm, column temperature of 35 ℃ which better retains the medium polar compound; mobile phase: the water phase is ammonium acetate water solution, the organic phase is acetonitrile, and the flow rate is 0.6mL/min; the elution procedure was gradient elution: eluting with 5% acetonitrile for 2min, then raising the acetonitrile gradient to 75% for 15min, then washing with 75% acetonitrile for 3min, and finally adjusting back to the initial ratio of 5% acetonitrile with 0.1min, and balancing for 8min; detection wavelength: 205nm; the disodium sulfosuccinate intermediate has fewer double bonds, and the detection wavelength of 205nm (short wavelength) is used for quantifying the disodium sulfosuccinate intermediate; the method comprises the following steps:
(1) Taking proper amounts of the disodium sulfosuccinate intermediate 1 and the intermediate 2 respectively, dissolving samples by using CAN as a diluent, and preparing sample solutions containing about 1mg of the disodium sulfosuccinate intermediate 1 or the intermediate 2 in concentration of each 1mL of the diluent respectively;
(2) And (3) injecting the solution obtained in the step (1) into a liquid chromatograph according to a sample injection volume of 10 mu L, recording a chromatogram, completing separation of the disodium sulfosuccinate intermediate and related substances, and detecting the purity of the disodium sulfosuccinate intermediate and the content of the related substances, wherein the related substances possibly exist are DMF and maleic anhydride.
Wherein the aqueous phase is 8mM ammonium acetate aqueous solution.
Wherein, the liquid chromatograph is a Thermo Ultimate 3000/VC, DAD detector.
The method adopts a C8 chromatographic column with better retention of the medium polar compound and an ammonium acetate aqueous solution/acetonitrile reversed phase buffer salt chromatographic system, so that the retention of the target compound can be enhanced; the gradient elution is used for separation, the purity of the disodium sulfosuccinate intermediate 1 and the purity of the intermediate 2 can be rapidly detected, the main component and related substances thereof are effectively separated, and the reaction of the disodium sulfosuccinate intermediate is monitored
The invention adopts 8mM ammonium acetate aqueous solution as the water phase, which enhances the retention of disodium sulfosuccinate intermediate in the mobile phase system.
The column temperature is set to 35 ℃, so that the situation of precipitation of ammonium acetate in the water phase caused by over low temperature is avoided, and the column temperature is also within the tolerance column temperature range of the chromatographic column.
The invention calculates the purity of the disodium sulfosuccinate intermediate and the content of related substances by adopting a percentage area method, and the established method is simple and easy to implement.
The invention monitors disodium sulfosuccinate intermediate and related substances thereof by adopting 205nm (short wavelength) to obtain proper UV absorbance and chromatographic peak height.
The method can simply and rapidly measure the purity of the disodium sulfosuccinate intermediate and the content of related substances, and solves the problem of reaction monitoring of the disodium sulfosuccinate intermediate in the production process.
Drawings
FIG. 1 is an HPLC overlay of disodium sulfosuccinate intermediate 1 and intermediate 2 of the process of the present invention;
FIG. 2 is an HPLC overlay of disodium sulfosuccinate intermediate and related materials of the process of the present invention.
Detailed Description
The invention will be further described with reference to the drawings and the specific examples.
The applicant finds that the disodium sulfosuccinate intermediate and related substances thereof can be effectively separated by using a C8 chromatographic column which better retains the medium polar compounds and using an ammonium acetate aqueous solution/acetonitrile as a mobile phase system for gradient elution, and the purity of the disodium sulfosuccinate intermediate and the content of the related substances can be accurately measured, so that an HPLC-UV method for detecting the purity of the key intermediate, the content of the related substances and the residual solvent in the process of preparing the disodium sulfosuccinate starting material is provided.
The HPLC detection method of the invention can be realized according to the following method:
(1) Samples were dissolved in ACN as a diluent by taking appropriate amounts of disodium sulfosuccinate intermediate 1 and intermediate 2, respectively, and about 1mg of sample solution containing disodium sulfosuccinate intermediate 1 or intermediate 2 per 1mL of diluent was prepared, respectively.
(2) Taking the solution in the step (1), and injecting the solution into a liquid chromatograph according to a sample injection volume of 10 mu L, wherein the detection conditions are as follows:
high performance liquid chromatograph: thermo Ultimate 3000, DAD detector.
Chromatographic column: dikma Diamonsil C8, 150 x 4.6mm,5 μm.
Mobile phase: 8mM ammonium acetate aqueous solution (lane I), acetonitrile (lane II).
Elution procedure: eluting with 5% acetonitrile for 2min, then raising acetonitrile gradient to 75% for 15min, washing with 75% acetonitrile for 3min, and finally adjusting back to the initial ratio of 5% acetonitrile with 0.1min for balancing for 8min.
Detection wavelength: 205nm.
Flow rate: 0.6mL/min.
Column temperature: 35 ℃.
Sample injection volume: 10 mu L.
The experimental steps are as follows: taking 10mg of guanidine hydrochloride as a starting material and 10mg of 2, 4-diamino-6-hydroxypyrimidine as a produced solid respectively, placing the materials in a 5mL volumetric flask, and adding ACN: H 2 O=1:1 (v/v) was dissolved and diluted to scale, shaken well, and used as a sample solution for method development.
Taking the sample solution, performing high performance liquid chromatography under the conditions, and recording a chromatogram. As a result, in FIG. 1, peak No. 1 is 2, 4-diamino-6-hydroxypyrimidine (main component), peak No. 2 is guanidine hydrochloride (known impurity of main component), and under this condition, the peak form of 2, 4-diamino-6-hydroxypyrimidine and known impurity guanidine hydrochloride to be controlled is good.
Comparative example 1
Instrument and conditions:
high performance liquid chromatograph: thermo Ultimate 3000, DAD detector.
Chromatographic column: YMC-Pack ODS-AQ,150×4.6mm,3 μm.
Mobile phase: h 2 O (lane one), meOH (lane two).
Elution procedure: eluting with 5% acetonitrile for 5min, then raising acetonitrile gradient to 90% for 9min, washing with 90% acetonitrile for 1.5min, and finally adjusting back to the initial ratio of 5% acetonitrile for 0.1min and balancing for 4.5min.
Detection wavelength: and (5) full sweeping.
Flow rate: 1.0mL/min.
Column temperature: 35 ℃.
Sample injection volume: 1 mul.
The experimental steps are as follows: respectively taking 20mg of disodium sulfosuccinate intermediate 1 and 20mg of disodium sulfosuccinate intermediate 2, placing into a 20mL volumetric flask, adding ACN to dissolve and dilute to scale, and shaking uniformly to obtain a main component sample solution for developing a method.
20mg of DMF and maleic anhydride are taken and placed in a 20mL volumetric flask, 0.2mL of each of the prepared main component sample solutions of the disodium sulfosuccinate intermediate 1 and the intermediate 2 are respectively added, and then dissolved and diluted to a scale by ACN, and shaking is carried out to obtain an RS sample solution for developing the method.
Taking the sample solution, performing high performance liquid chromatography under the conditions, and recording a chromatogram. The results are shown in FIG. 1 and FIG. 2. In FIG. 1, the M01 peak is the disodium sulfosuccinate intermediate 1, and the M02 peak is the disodium sulfosuccinate intermediate 2. As can be seen from the figure, under this condition, the peak patterns of the disodium sulfosuccinate intermediate 1 and the intermediate 2 are good, and the two can be completely separated, and the peak heights are suitable. In FIG. 2, peak A is DMF, peak B is maleic anhydride, peak M01 is disodium sulfosuccinate intermediate 1, and peak M02 is disodium sulfosuccinate intermediate 2. As can be seen from the figure, under this condition, disodium sulfosuccinate intermediate 1 and intermediate 2 can be completely separated from DMF and maleic anhydride, which are related substances, and a peak is evident at a concentration level of 100%, and disodium sulfosuccinate intermediate 1 and intermediate 2 at a concentration level of 1% respond well.
The above embodiments are merely illustrative of the principles of the present invention and its effectiveness, and some practical embodiments, and variations and modifications may be made by those skilled in the art without departing from the inventive concept, which are all within the scope of the present invention.
Claims (1)
1. HPLC-UV detection method for disodium sulfosuccinate intermediate purity, wherein structural formula of undecylenamide MEA-disodium sulfosuccinate for detection isMolecular formula C 17 H 27 NNa 2 O 8 S, chemical name of Disodium 4- [2- [ (1-oxoudec-10-enyl) amino ]]ethyl]2-sulfophosphate; the method is characterized in that the detection conditions are as follows:
chromatographic column: dikma Diamonsil C8, 150 x 4.6mm,5 μm, column temperature 35 ℃;
mobile phase: the aqueous phase is 8mM ammonium acetate aqueous solution, the organic phase is acetonitrile, and the flow rate is 0.6mL/min;
elution procedure: eluting with 5% acetonitrile for 2min, gradient-increasing acetonitrile to 75% at 15min, washing with 75% acetonitrile for 3min, and adjusting back to the initial ratio of 5% acetonitrile with 0.1min, and balancing for 8min;
detection wavelength: 205nm;
the method comprises the following steps:
(1) Respectively taking disodium sulfosuccinate intermediate, and dissolving with acetonitrile as a diluent to prepare a sample solution with the concentration of 1mg of disodium sulfosuccinate intermediate in each 1mL of diluent;
(2) Injecting the solution obtained in the step (1) into a liquid chromatograph according to a sample injection volume of 10 mu L, recording a chromatogram, completing separation of disodium sulfosuccinate intermediate and related substances, and detecting the purity of the disodium sulfosuccinate intermediate and the content of the related substances;
the liquid chromatograph is a Thermo Ultimate 3000/VC and DAD detector.
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| CN202210741371.XA CN115112795B (en) | 2022-06-28 | 2022-06-28 | HPLC-UV detection method for purity of disodium sulfosuccinate intermediate |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07197078A (en) * | 1993-12-29 | 1995-08-01 | Kawaken Fine Chem Co Ltd | Polyoxyethylene fatty acid amide sulfosuccinic acid ester type surfactant, its production and detergent composition |
| WO2013186390A1 (en) * | 2012-06-15 | 2013-12-19 | Farma Grs, D.O.O. | Selective crystallization processes using reverse micelle and w/o microemulsion systems - multitask emulsion crystallization (mec) |
| CN108152316A (en) * | 2017-12-14 | 2018-06-12 | 中国日用化学工业研究院 | It is a kind of using maleic anhydride content and sulphonation rate as the quality inspection method of the glucosides sulfosuccinate ester salt product of index |
| CN109100454A (en) * | 2018-10-24 | 2018-12-28 | 中国日用化学研究院有限公司 | Method that is a kind of while measuring surfactant product sulfite salt and sulphates content |
| CN109115926A (en) * | 2018-10-24 | 2019-01-01 | 中国日用化学研究院有限公司 | The measuring method of sulfosuccinic acid content in Sulfosuccinate Surfactant product |
-
2022
- 2022-06-28 CN CN202210741371.XA patent/CN115112795B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07197078A (en) * | 1993-12-29 | 1995-08-01 | Kawaken Fine Chem Co Ltd | Polyoxyethylene fatty acid amide sulfosuccinic acid ester type surfactant, its production and detergent composition |
| WO2013186390A1 (en) * | 2012-06-15 | 2013-12-19 | Farma Grs, D.O.O. | Selective crystallization processes using reverse micelle and w/o microemulsion systems - multitask emulsion crystallization (mec) |
| CN108152316A (en) * | 2017-12-14 | 2018-06-12 | 中国日用化学工业研究院 | It is a kind of using maleic anhydride content and sulphonation rate as the quality inspection method of the glucosides sulfosuccinate ester salt product of index |
| CN109100454A (en) * | 2018-10-24 | 2018-12-28 | 中国日用化学研究院有限公司 | Method that is a kind of while measuring surfactant product sulfite salt and sulphates content |
| CN109115926A (en) * | 2018-10-24 | 2019-01-01 | 中国日用化学研究院有限公司 | The measuring method of sulfosuccinic acid content in Sulfosuccinate Surfactant product |
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Inventor after: Guan Danyingzi Inventor after: Mei Qing Inventor after: Hu Jin Inventor after: Chai Jinzhu Inventor before: Chai Jinzhu Inventor before: Guan Danyingzi Inventor before: Mei Qing Inventor before: Hu Jin |
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