CN111094970A - Method for analyzing sucrose ester sample - Google Patents
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Abstract
The present application provides a method for analyzing a sucrose ester sample by using an ultra-high performance phase chromatograph in combination with a mass spectrometer. The method for analyzing the sucrose ester sample can realize quantitative analysis of different sucrose ester contents in the sample, and has high accuracy; the method for analyzing the sucrose ester sample provided by the application has the advantages of extremely short time, high-efficiency analysis and high efficiency; and the used solvent has extremely low toxicity, and is safe and environment-friendly.
Description
Technical Field
The application belongs to the technical field of chemical analysis and relates to a method for analyzing a sucrose ester sample.
Background
Sucrose fatty acid ester is also called sucrose ester (SE for short) and is prepared by taking sucrose as a raw material, and because the sucrose contains 8-OH groups, various products from monoester to octaester can be generated after esterification; can be subdivided into mono-fatty acid esters, di-fatty acid esters, tri-fatty acid esters and poly-fatty acid esters (greater than three). The sucrose-OH group is hydrophilic group, the carbon chain of fatty acid is lipophilic group, and higher fatty acid (powder) such as stearic acid, oleic acid, and palmitic acid, or lower fatty acid (viscous resin) such as acetic acid and isobutyric acid can be used. It is non-toxic, easy to biodegrade and has excellent surface performance, and may be used widely in food, medicine, enzyme preparation for daily use chemical engineering, oil exploitation, textile, agriculture and animal husbandry and other industries.
The sucrose ester has good emulsifying effect on water and oil, and HLB (hydrophilic-lipophilic balance) value can be adjusted in a wide range. As an excellent nonionic surfactant, the cationic surfactant is widely applied to a plurality of fields of food, pharmacy, daily chemicals and the like, and has wide development prospect. The standard of sucrose ester is promulgated in 1987 (GB8272-1987) in China, a quality analysis standard method of the sucrose ester is stipulated, and a new standard (GB8272-2009) is used for replacing the old standard in 2009 to further perfect a quality control system of the sucrose ester. Standards specify the determination methods for the appearance, components, acid value and free sugar of sucrose esters, but the conventional volumetric analysis method is mainly used, the analysis of components is limited to qualitative analysis, and the application of modern analytical instruments and newly developed analytical methods in recent years are not reflected in the standards.
In the qualitative and quantitative analysis of sucrose esters, Thin Layer Chromatography (TLC) is used more often, but since sucrose esters do not develop color by themselves, color development with a color developer is required. Gas Chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) are also used for quantitative and qualitative analysis of sucrose esters, but derivatization of sucrose esters is required, which is a complicated process. As a rapid quantitative method, High Performance Liquid Chromatography (HPLC) ultraviolet detection and high performance liquid chromatography differential detection are both used for analysis of sucrose esters, and since the ultraviolet absorption of sucrose esters is weak, the differential detector cannot perform gradient elution. Therefore, it is important to find a method for rapidly analyzing sucrose esters.
CN103134872A discloses a method for analyzing the distribution of various esters in sucrose fatty acid ester by gel permeation chromatography, which comprises dissolving sucrose fatty acid ester reference substance in tetrahydrofuran to obtain reference substance solution, analyzing the reference substance solution by gel permeation chromatograph, obtaining the chromatographic peak area value of various esters of the reference substance according to GPC spectrogram, calculating the composition of various esters by area normalization method, and correspondingly obtaining the retention time of various esters; and then dissolving a sucrose fatty acid ester sample in tetrahydrofuran to prepare a sample solution, analyzing and determining by adopting the same chromatographic analysis conditions to obtain a GPC spectrogram of the sample, correspondingly obtaining peak area values of various esters in the sample according to the retention time of various esters in a reference substance, and calculating by using an area normalization method to obtain the distribution of various esters in the sucrose fatty acid ester sample. The method given in this patent, although simple, is relatively long in analysis time.
Therefore, it is necessary to develop a method capable of realizing fast and efficient detection to improve the overall detection efficiency.
Disclosure of Invention
It is an object of the present application to provide a method for analyzing a sucrose ester sample. The method for analyzing the sucrose ester sample can realize quantitative analysis of different sucrose ester contents in the sample, and has high accuracy; the method for analyzing the sucrose ester sample provided by the application has the advantages of extremely short time, high-efficiency analysis and high efficiency; and the used solvent has extremely low toxicity, and is safe and environment-friendly.
To achieve the purpose, the following technical scheme is adopted in the application:
in a first aspect, the present application provides a method for analyzing a sucrose ester sample by using an ultra-high performance phase chromatograph in combination with a mass spectrometer.
The analysis method can realize quantitative analysis of different sucrose ester contents in the sucrose ester sample, and has high accuracy; the method has the advantages of extremely short time, high-efficiency analysis and high efficiency.
In the present application, the sucrose ester sample is analyzed as a solution of the sucrose ester sample.
Preferably, the solvent of the sucrose ester sample solution is any one of methanol, isopropanol and dichloromethane or a combination of at least two thereof.
Preferably, the temperature of the sucrose ester sample solution is 5-20 deg.C, such as 8 deg.C, 10 deg.C, 12 deg.C, 15 deg.C, 18 deg.C, etc.
In the present application, the sucrose ester sample may include any one of sucrose monoesters, sucrose diesters, and sucrose triesters, or a combination of at least two thereof.
In the present application, the sucrose monoesters include sucrose palmitate and/or sucrose stearate monoesters.
In the present application, the sucrose diester includes sucrose palmitate diester and/or sucrose stearate diester.
In the present application, the sucrose triester includes sucrose palmitate triester and/or sucrose stearate triester.
The analysis method provided by the application can be used for analyzing any sucrose ester including mono-ester, di-ester or tri-ester, can realize high-efficiency quantitative analysis, and can also be used for content analysis of a specific sucrose ester.
In the present application, the ultra-high performance phase chromatograph comprises a chromatographic column.
Preferably, the temperature of the chromatography column is 30-40 ℃, such as 32 ℃, 35 ℃, 37 ℃ and the like.
Preferably, the sample injection volume of the ultra-high performance phase-combining chromatograph is 1.0 μ L.
In the present application, the chromatography column is a silica gel chromatography column.
Preferably, the length of the chromatography column is 100 mm.
Preferably, the particle size of the silica gel of the chromatographic column is 1.7 μm.
In the present application, the mobile phase a used in the ultra-high performance phase chromatograph is carbon dioxide.
Preferably, the mobile phase B used by the ultra-high performance phase chromatograph is methanol.
Preferably, the sum of the flow rates of the mobile phase A and the mobile phase B used by the ultra-high performance phase chromatograph is 1 mL/min.
In the present application, the compensation liquid used in the ultra-high performance phase chromatograph is an alcohol solution.
Preferably, the compensation liquid is methanol or a methanol solution containing ammonium formate.
Preferably, the volume fraction of ammonium formate is 0.5%.
The method for analyzing the sucrose ester sample provided by the application has the advantages that the time is extremely short, the efficient analysis can be realized, and the efficiency is higher; and the used solvent has extremely low toxicity, and is safe and environment-friendly.
In the present application, the source temperature of the mass spectrometer is 135-165 ℃, e.g., 140 ℃, 145 ℃, 150 ℃, 155 ℃, 160 ℃, etc.
Preferably, the source temperature of the mass spectrometer is 150 ℃ and the desolventizing gas temperature is 350 ℃.
In the present application, the mass spectrometer has a desolvation gas flow rate of 400-600L/Hr, such as 420L/Hr, 450L/Hr, 470L/Hr, 500L/Hr, 520L/Hr, 550L/Hr, 570L/Hr, etc.
Preferably, the mass spectrometer has a desolventizing gas flow rate of 500L/Hr, a capillary voltage of 3.0kV and a cone hole voltage of 40V.
Compared with the prior art, the method has the following beneficial effects:
the methods provided herein for analyzing sucrose ester samples can be implementedThe quantitative analysis of the contents of different sucrose esters in the sucrose ester sample has higher accuracy; the method for analyzing the sucrose ester sample provided by the application has the advantages of extremely short time, high-efficiency analysis and high efficiency; the toxicity of the used solvent is extremely low, the method is safe and environment-friendly, the analysis of sucrose ester can be completed within two minutes, the analysis error is small, and the correlation coefficient R2>0.99。
Drawings
Figure 1 is a standard curve obtained from testing different concentrations of sucrose stearate monoester standard using the method provided in example 1.
Figure 2 is a standard curve obtained from testing different concentrations of sucrose palmitate standards using the method provided in example 1.
Figure 3 is a standard curve obtained from testing different concentrations of sucrose palmitate diester standard using the method provided in example 1.
Detailed Description
The technical solution of the present application is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present application and should not be construed as a specific limitation of the present application.
Example 1
A method of analyzing a sucrose ester sample comprising the steps of:
(1) analyzing the sucrose ester sample solution by using a method of combining an ultra-high performance combined chromatograph and a mass spectrometer, wherein the test conditions are as follows:
ultra-efficient phase-combination chromatograph:
the system comprises the following steps: ACQUITY UPC2；
A chromatographic column:
BEH Column,1.7μm,3x100mm；
column temperature: 40 ℃;
sample temperature: 10 ℃;
sample introduction volume: 1.0 μ L;
flow rate: 1 mL/min;
mobile phase A: CO 22；
Mobile phase B: methanol;
compensation liquid: 0.5% ammonium formate solution in methanol (volume fraction, 0.2 mL/min);
a flow divider: upchurch cross-piece 1/16 PEEK;
detection time: and 2 min.
Mass spectrometry: SQ Detector 2;
ionization mode: ESI +;
capillary voltage: 3.0 kV;
taper hole voltage: 40V;
source temperature: 150 ℃;
desolventizing gas temperature: 350 ℃;
flow rate of taper hole gas: 0L/h;
desolventizing air flow rate: 500L/Hr.
Performance testing
The performance test was performed on the method for analyzing sucrose ester samples provided in example 1, as follows:
(1) the sucrose stearate monoester standard was dissolved in methanol so that the concentrations of the sucrose stearate monoester standard were 0.01mg/mL, 0.02mg/mL, 0.04mg/mL, 0.08mg/mL and 0.16mg/mL, and the sample solution was analyzed by the analysis method provided in example 1, and the results were as follows:
figure 1 is a standard curve for sucrose stearate monoester. As can be seen from the figure, the correlation coefficient R2＝0.993997>0.99, which shows that the concentration of sucrose stearate monoester is in a good linear relationship within the range of 0.01-0.16mg/mL, the method for analyzing the sucrose ester sample provided by the application can be applied to quantitative analysis of sucrose stearate monoester in the sucrose ester sample.
(2) The sucrose palmitate monoester standards were dissolved in methanol to give concentrations of 0.01mg/mL, 0.02mg/mL, 0.04mg/mL, 0.08mg/mL and 0.16mg/mL, and the sample solutions were analyzed by the analysis method provided in example 1, and the results were as follows:
FIG. 2 is a standard curve of sucrose palmitate monoester. As can be seen from the figure, the correlation coefficient R2＝0.998480>0.99, which shows that the linear relation of the concentration of the sucrose palmitate is good in the range of 0.01-0.16mg/mL, the method for analyzing the sucrose ester sample provided by the application can be applied to quantitative analysis of the sucrose palmitate in the sucrose ester sample.
(3) The test was carried out using the method provided in example 1 of the present application for each of models S-570, S-770, S-970, S-1570, S-1670 and P-1570, P-1670 purchased from Mitsubishi corporation of Japan, and the test results are shown in Table 1:
TABLE 1
The embodiment and the performance test show that the standard curves of the sucrose stearate monoester and the sucrose palmitate monoester have good linear relation, can be applied to quantitative analysis of the sucrose stearate monoester and the sucrose palmitate monoester in a sucrose ester sample, and has small analysis error within 9% in the quantitative analysis process.
(4) The sucrose palmitate diester standards were dissolved in isopropanol to give concentrations of 0.08mg/mL, 0.10mg/mL, 0.14mg/mL, 0.16mg/mL, and 0.20mg/mL, and the sample solutions were analyzed by the analysis method provided in example 1, with the following results:
FIG. 3 is a standard curve of sucrose palmitate monoester. As can be seen from the figure, the correlation coefficient R2＝0.992394>0.99, the linear relation of the concentration of the sucrose palmitate diester in the range of 0.08-0.20 mg/mL is good, and the method for analyzing the sucrose ester sample can be applied to quantitative analysis of the sucrose palmitate diester in the sucrose ester sample.
The applicant states that the present application illustrates the method of analyzing a sucrose ester sample of the present application by means of the above examples, but the present application is not limited to the above process steps, i.e. it does not mean that the present application has to rely on the above process steps to be carried out. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitution of selected materials for the present application, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present application.
Claims (15)
1. A method for analyzing a sucrose ester sample by using an ultra-high performance phase chromatograph in combination with a mass spectrometer.
2. The method of claim 1, wherein the sucrose ester sample is analyzed as a sucrose ester sample solution.
3. The method of claim 2, wherein the solvent of the sucrose ester sample solution is any one of methanol, isopropanol, and dichloromethane, or a combination of at least two thereof.
4. The method of claim 2, wherein the temperature of the sucrose ester sample solution is 5-20 ℃.
5. The method of any one of claims 1-4, wherein the sucrose ester comprises any one of, or a combination of at least two of, a sucrose monoester, a sucrose diester, and a sucrose triester.
6. A process according to claim 5, wherein the sucrose monoesters comprise sucrose palmitate and/or sucrose stearate monoesters.
7. The method of claim 5, wherein the sucrose diester comprises a sucrose palmitate diester and/or a sucrose stearate diester.
8. The method of claim 5, wherein the sucrose triester comprises sucrose palmitate and/or sucrose stearate triester.
9. The method of any one of claims 1-8, wherein the ultra-high performance phase chromatograph comprises a chromatography column.
10. The method of claim 9, wherein the temperature of the chromatographic column is 30-40 ℃;
preferably, the sample injection volume of the ultra-high performance phase-combining chromatograph is 1.0 μ L.
11. The method of claim 9 or 10, wherein the chromatography column is a silica gel chromatography column;
preferably, the length of the chromatography column is 100 mm;
preferably, the particle size of the silica gel of the chromatographic column is 1.7 μm.
12. The method of any one of claims 9-11, wherein the mobile phase a used by the ultra-high performance phase chromatograph is carbon dioxide;
preferably, the mobile phase B used by the ultra-high performance phase-combining chromatograph is methanol;
preferably, the sum of the flow rates of the mobile phase A and the mobile phase B used by the ultra-high performance phase chromatograph is 1 mL/min.
13. The method of any one of claims 9-12, wherein the compensation fluid used by the ultra-high performance phase chromatograph is an alcohol solution;
preferably, the compensation liquid is methanol or a methanol solution containing ammonium formate;
preferably, the volume fraction of ammonium formate is 0.5%.
14. The method as claimed in any one of claims 1-13, wherein the source temperature of the mass spectrometer is 135-165 ℃;
preferably, the source temperature of the mass spectrometer is 150 ℃ and the desolventizing gas temperature is 350 ℃.
15. The method as claimed in any one of claims 1 to 14, wherein the mass spectrometer has a desolvation gas flow rate of 400-600L/Hr;
preferably, the mass spectrometer has a desolventizing gas flow rate of 500L/Hr, a capillary voltage of 3.0kV and a cone hole voltage of 40V.
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| CN106290609A (en) * | 2016-07-26 | 2017-01-04 | 重庆市计量质量检测研究院 | A kind of detection method of phthalate material |
| CN107064362A (en) * | 2017-04-19 | 2017-08-18 | 国家烟草质量监督检验中心 | The measure of parabens material in buccal cigarette |
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| CN104774889B (en) * | 2015-03-25 | 2018-08-17 | 郑州轻工业学院 | A method of preparing cane sugar-6-acetic ester using transfructosylase |
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| CN106290609A (en) * | 2016-07-26 | 2017-01-04 | 重庆市计量质量检测研究院 | A kind of detection method of phthalate material |
| CN107064362A (en) * | 2017-04-19 | 2017-08-18 | 国家烟草质量监督检验中心 | The measure of parabens material in buccal cigarette |
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