CN105675749A - Analysis method of carbon chain composition of cocoyl amino acid surfactants - Google Patents
Analysis method of carbon chain composition of cocoyl amino acid surfactants Download PDFInfo
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Abstract
The invention relates to an analysis method of carbon chain composition of cocoyl amino acid surfactants. The method comprises the following steps: hydrolysis is carried out for cocoyl amino acid/salt, coconut oil fatty acid is obtained, and HPLC analysis is carried out after derivatization. The analysis method is not influenced by kinds of amino acid surfactants, as long as the type of the surfactant accords with fatty acyl amino acid/salt; the analysis method has the advantages of simple operation, low cost, and high sensitivity, and the analysis method is not influenced by length of carbon chain.
Description
Technical field
The present invention relates to chemical analysis technology field, particularly relate to the analysis method of a kind of cocoyl amino acid surfactant carbochain composition.
Background technology
As the typical fatty acid acylamino acid class surfactant of one, cocoyl aminoacid/salt prepares with natural amino acid, coconut oil for raw material. Excellent degradation property, extremely low toxicity and zest make it be applicable to the industries such as food, medicine, daily use chemicals. In household chemicals field; cocoyl aminoacid/salt has that antistatic, sterilizing ability, compatibility be good, the characteristic of resistance to hard water; various liquid, cream kind cleansing milk, facial film, skin care product, toothpaste, washing class articles for use can be widely used in, in the product such as hair washing, bath gel and various fancy soaps.
Cocoyl aminoacid/salt is a kind of mixed amino-acid surfactant; mainly comprise the components such as octanoylamino acid/salt, decanoylamino acid/salt, lauroyl aminoacid/salt, myristoyl aminoacid/salt, palmitoyl amino acid/salt, hard acylamino acid/salt, wherein the highest with lauroyl aminoacid/salt content. Clearly different carbochain compositions can its surface activity of appreciable impact: the first, the CMC value of each component reduces along with the prolongation of alkyl chain; The second, short carbon chain component is bubbled and is steeped difference soon and surely, and Long carbon chain component foaming slow and steady soaks; 3rd, each component has distinct contribution to the viscosity of product formula, skinfeel, compatibility, even zest. Therefore, the complete carbochain ratio monitoring cocoyl aminoacid/salt is particularly important.
In order to detect the complete carbochain ratio of cocoyl aminoacid/salt, Some Enterprises adopts the direct HPLC way analyzed, though this method is simple to operate but free fatty acid cannot be detected. In order to overcome this shortcoming, be developed the way of gas chromatogram (GC) later: first cocoyl aminoacid/salt complete hydrolysis is obtained coconut oil, then by coconut acid methylester or ethyl esterified after carry out GC analysis. But the method is difficult to prove effective for the analysis of Long carbon chain component.
Summary of the invention
Based on this, it is an object of the invention to provide the analysis method of a kind of cocoyl amino acid surfactant carbochain composition.
Concrete technical scheme is as follows:
The analysis method of a kind of cocoyl amino acid surfactant carbochain composition, comprises the steps:
(1) cocoyl amino acid surfactant is dispersed in hydrochloric acid, after heating reflux reaction 3.5～4.5h, is cooled to room temperature, adjust pH value to 1.5～2.0;
(2) fatty acid in the reactant liquor obtained by n-hexane extraction step (1), add desiccant, it is filtered to remove desiccant after drying, then evaporation operation is rotated, obtain fatty acid extract, fatty acid extract is mixed to get DMF solution with DMF by the mass ratio of 1:5～10;
(3) accurately weigh alpha-brominated 1-Phenylethanone. and KF, be dissolved in DMF, add the DMF solution that step (2) obtains, at 95～105 DEG C, then react 15～25min, after being cooled to room temperature, add acetonitrile, vibration, centrifugal after take supernatant;
(4) supernatant that step (3) obtains is carried out efficient liquid phase chromatographic analysis, to obtain final product.
Wherein in some embodiments, described cocoyl amino acid surfactant is selected from: cocoyl sarcosine, Sodium Coco acylsarcosinate, cocoyl sarcosine potassium, cocoyl sarcosine triethanolamine salt, cocoyl glycine, cocoyl Glycine sodium, cocoyl glycine potassium, cocoyl glycine triethanolamine salt, cocoyl alanine, cocoyl Sodium L-alaninate, cocoyl alanine potassium, cocoyl alanine triethanolamine salt, cocoyl glutamic acid, sodium cocoyl glutamate, cocoyl disodium glutamate, cocoyl Kaglutam, cocoyl glutamic acid triethanolamine salt or sodium cocoyl methyl sodium taurocholate.
Wherein in some embodiments, in step (3), the mol ratio of KF, alpha-brominated 1-Phenylethanone. and fatty acid is 8～6:4～3:1.
Wherein in some embodiments, in step (4), the condition of high performance liquid chromatography is:
Chromatographic column: anti-phase C18 post; Column temperature: 25～35 DEG C; Detection wavelength 254 ± 5nm;
Mobile phase: mobile phase A is acetonitrile, Mobile phase B is water, adopts gradient elution mode: from 0～15min, and the volume ratio of mobile phase A and Mobile phase B is 65～75:35～25; From 15～40min, the percentage by volume of mobile phase A is changed to 100% by 65～75%; Flow velocity is 0.8-1.2ml/min.
Wherein in some embodiments, the condition of described high performance liquid chromatography is:
Chromatographic column: anti-phase C18 post; Column temperature: 30 DEG C; Detection wavelength 254nm;
Mobile phase: mobile phase A is acetonitrile, Mobile phase B is water, adopts gradient elution mode: from 0～15min, and the volume ratio of mobile phase A and Mobile phase B is 70:30; From 15～40min, the percentage by volume of mobile phase A is changed to 100% by 70%; Flow velocity is 1.0ml/min.
Wherein in some embodiments, the concentration of the hydrochloric acid in step (1) is 6.0mol/L.
Wherein in some embodiments, desiccant described in step (2) is anhydrous sodium sulfate.
Wherein in some embodiments, in step (3), the addition of acetonitrile is the twice of reactant liquor volume.
Principles of the invention is as follows:
The analysis method of the present invention is first by cocoyl aminoacid/salt complete hydrolysis, extracts and obtains coconut oil, then carries out HPLC analysis after derivatization. This method obtains fatty acid proportion and includes the contribution of two aspects: (1) active matter cocoyl aminoacid/salt; (2) free coconut oil/salt. The problem that this method overcomes the free coconut oil/salt of missing inspection during traditional technique in measuring carbochain ratio.
Concrete step is: first refluxed when high-temperature strong acid by cocoyl aminoacid/salt, and amido link just can obtain fatty acid after being thoroughly hydrolyzed. Then under KF catalytic condition, the fatty section obtained is reacted with bromoacetophenone, just can obtain fatty acid phenacyl ester. The reactant liquor obtained is carried out HPLC analysis, just can obtain the mol ratio of different carbon chain component. Therefore theoretically, due to the high efficiency separation ability of HPLC, this method can analyze the cocoyl aminoacid/salt sample of any carbochain composition.
Beneficial effects of the present invention:
1, cocoyl aminoacid/salt is first hydrolyzed and obtains coconut oil by the analysis method of the present invention, carries out HPLC analysis after derivatization, and the method is not by the impact of amino acid surfactant kind, as long as meet the type of fatty acid acylamino acid/salt;
2, the analysis method of the present invention is simple to operate, cost is low, highly sensitive, not by the impact of carbon chain lengths.
Accompanying drawing explanation
Fig. 1 is the high-efficient liquid phase chromatogram of embodiment 1;
Fig. 2 is the high-efficient liquid phase chromatogram of embodiment 2.
Detailed description of the invention
By the following examples the application is further elaborated.
Embodiment 1:
The HPLC (high performance liquid chromatography) of a kind of cocoyl Sodium L-alaninate carbochain composition of the present embodiment, comprises the steps:
(1) being dispersed in 50mL6N hydrochloric acid by 1.0g cocoyl Sodium L-alaninate (commercially available), heating is so as to be cooled to room temperature by reactant liquor after the 4h that refluxes, with 32% liquid adjusting PH with base to 1.5～2.0;
(2) first with normal hexane, fatty acid in system is extracted and (extract three times, each 100mL normal hexane), then dry, with about 10g anhydrous sodium sulfate, the extract obtained, carry out rotary evaporation after filtering desiccant and obtain fatty acid extract, it is dissolved stand-by with 5mLDMF;
(3) the alpha-brominated 1-Phenylethanone. of 0.71g and 0.42gKF are weighed, add the DMF solution (mol ratio of KF, alpha-brominated 1-Phenylethanone. and fatty acid being controlled: within the scope of 8～6:4～3:1) that step (2) obtains after disperseing with 5mLDMF and stirring 1min, then place reaction liquid into reaction 20min under 100 DEG C of conditions. Adding 20mL acetonitrile after being cooled to room temperature to vibrate about 1min, when 8000rpm, to take supernatant to be measured for centrifugal about 5min;
(4) supernatant that step (3) obtains being carried out high-efficient liquid phase analysis, actual conditions is as follows:
Chromatographic apparatus configures: HPLC instrument (Japan's Shimadzu LC-20AD type chromatograph, Shimadzu CTO-10AS column oven, Shimadzu SPD-M20A diode array detector); Chromatogram record (Shimadzu LCsolution work station).
Chromatographic column: AgilentZORBAXSB-C185 μm of 4.6*150mm
Column temperature: 30 DEG C.
Detection wavelength: 254nm.
Mobile phase: B: ultra-pure water, A: acetonitrile.
Gradient condition:
Experiment chromatogram is as it is shown in figure 1, shown in carbochain table composed as follows:
| Component | Retention time | Area | Highly | Area % |
| C8 | 7.274 | 756409 | 79030 | 9.379 |
| C10 | 10.864 | 707102 | 78354 | 8.768 |
| C12 | 14.481 | 5094573 | 574242 | 63.169 |
| C14 | 17.550 | 1291832 | 164625 | 16.018 |
| C16 | 20.099 | 215028 | 25510 | 2.666 |
| Amount to | 8064943 | 921761 | 100.000 |
It should be noted that: the peak position that goes out of C8～C16 component has been determined by the way that we determine peak by standard sample, and each retention time and peak area as above represent for they. It is obvious that by the relative scale calculating each component peaks area, the definite carbochain ratio of cocoyl Sodium L-alaninate sample just can be obtained.
Embodiment 2:
The HPLC (high performance liquid chromatography) of a kind of cocoyl Glycine sodium carbochain composition of the present embodiment, comprises the steps:
(1) being dispersed in 50mL6N hydrochloric acid by 1.0g cocoyl Glycine sodium (commercially available), heating is so as to be cooled to room temperature by reactant liquor after the 4h that refluxes, with 32% liquid adjusting PH with base to 1.5-2.0;
(2) first with normal hexane, fatty acid in system is extracted and (extract three times, each 100mL normal hexane), then dry, with about 10g anhydrous sodium sulfate, the extract obtained, carry out rotary evaporation after filtering desiccant and obtain oil-like extracts, it is dissolved stand-by with 5mLDMF;
(3) the alpha-brominated 1-Phenylethanone. of 0.75g and 0.44gKF are weighed, add the DMF solution (mol ratio of KF, alpha-brominated 1-Phenylethanone. and fatty acid being controlled within the scope of 8～6:4～3:1) that step (2) obtains after disperseing with 5mLDMF and stirring 1min, then place reaction liquid into reaction 20min under 100 DEG C of conditions. Adding 20mL acetonitrile after being cooled to room temperature to vibrate about 1min, when 8000rpm, to take supernatant to be measured for centrifugal about 5min;
(4) supernatant that step (3) obtains being carried out high-efficient liquid phase analysis, actual conditions is as follows:
Chromatographic apparatus configures: HPLC instrument (Japan's Shimadzu LC-20AD type chromatograph, Shimadzu CTO-10AS column oven, Shimadzu SPD-M20A diode array detector); Chromatogram record (Shimadzu LCsolution work station).
Chromatographic column: AgilentZORBAXSB-C185 μm of 4.6*150mm
Column temperature: 30 DEG C.
Detection wavelength: 254nm.
Mobile phase: B: ultra-pure water, A: acetonitrile.
Gradient condition:
Experiment chromatogram is as in figure 2 it is shown, shown in carbochain table composed as follows:
| Component | Retention time | Area | Highly | Area % |
| C8 | 7.240 | 2738365 | 291103 | 8.927 |
| C10 | 10.812 | 2838911 | 306119 | 9.255 |
| C12 | 14.396 | 18185697 | 1768634 | 59.285 |
| C14 | 17.472 | 5784823 | 702793 | 18.858 |
| C16 | 20.021 | 1127473 | 135329 | 3.676 |
| Amount to | 30675268 | 3203977 | 100.000 |
It should be noted that: the peak position that goes out of C8～C16 component has been determined by the way that we determine peak by standard sample, and each retention time and peak area as above represent for they. It is obvious that by the relative scale calculating each component peaks area, the definite carbochain ratio of cocoyl Glycine sodium sample just can be obtained.
Each technical characteristic of embodiment described above can combine arbitrarily, for making description succinct, the all possible combination of each technical characteristic in above-described embodiment is not all described, but, as long as the combination of these technical characteristics is absent from contradiction, all it is considered to be the scope that this specification is recorded.
Embodiment described above only have expressed the several embodiments of the present invention, and it describes comparatively concrete and detailed, but can not therefore be construed as limiting the scope of the patent. It should be pointed out that, for the person of ordinary skill of the art, without departing from the inventive concept of the premise, it is also possible to making some deformation and improvement, these broadly fall into protection scope of the present invention. Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (8)
1. the analysis method of a cocoyl amino acid surfactant carbochain composition, it is characterised in that comprise the steps:
(1) cocoyl amino acid surfactant is dispersed in hydrochloric acid, after heating reflux reaction 3.5～4.5h, is cooled to room temperature, adjust pH value to 1.5～2.0;
(2) fatty acid in the reactant liquor obtained by n-hexane extraction step (1), add desiccant, it is filtered to remove desiccant after drying, then evaporation operation is rotated, obtain fatty acid extract, fatty acid extract is mixed to get DMF solution with DMF by the mass ratio of 1:5～10;
(3) accurately weigh alpha-brominated 1-Phenylethanone. and KF, be dissolved in DMF, add the DMF solution that step (2) obtains, at 95～105 DEG C, then react 15～25min, after being cooled to room temperature, add acetonitrile, vibration, centrifugal after take supernatant;
(4) supernatant that step (3) obtains is carried out efficient liquid phase chromatographic analysis, to obtain final product.
2. analysis method according to claim 1, it is characterized in that, described cocoyl amino acid surfactant is selected from: cocoyl sarcosine, Sodium Coco acylsarcosinate, cocoyl sarcosine potassium, cocoyl sarcosine triethanolamine salt, cocoyl glycine, cocoyl Glycine sodium, cocoyl glycine potassium, cocoyl glycine triethanolamine salt, cocoyl alanine, cocoyl Sodium L-alaninate, cocoyl alanine potassium, cocoyl alanine triethanolamine salt, cocoyl glutamic acid, sodium cocoyl glutamate, cocoyl disodium glutamate, cocoyl Kaglutam, cocoyl glutamic acid triethanolamine salt or sodium cocoyl methyl sodium taurocholate.
3. analysis method according to claim 1, it is characterised in that in step (3), the mol ratio of KF, alpha-brominated 1-Phenylethanone. and fatty acid is 8～6:4～3:1.
4. analysis method according to claim 1, it is characterised in that in step (4), the condition of high performance liquid chromatography is:
Chromatographic column: anti-phase C18 post; Column temperature: 25～35 DEG C; Detection wavelength 254 ± 5nm;
Mobile phase: mobile phase A is acetonitrile, Mobile phase B is water, adopts gradient elution mode: from 0～15min, and the volume ratio of mobile phase A and Mobile phase B is 65～75:35～25; From 15～40min, the percentage by volume of mobile phase A is changed to 100% by 65～75%; Flow velocity is 0.8～1.2ml/min.
5. analysis method according to claim 4, it is characterised in that the condition of described high performance liquid chromatography is:
Chromatographic column: anti-phase C18 post; Column temperature: 30 DEG C; Detection wavelength 254nm;
Mobile phase: mobile phase A is acetonitrile, Mobile phase B is water, adopts gradient elution mode: from 0～15min, and the volume ratio of mobile phase A and Mobile phase B is 70:30; From 15～40min, the percentage by volume of mobile phase A is changed to 100% by 70%; Flow velocity is 1.0ml/min.
6. the analysis method according to any one of Claims 1 to 5, it is characterised in that in step (1), the concentration of hydrochloric acid is 6.0mol/L.
7. the analysis method according to any one of Claims 1 to 5, it is characterised in that in step (2), described desiccant is anhydrous sodium sulfate.
8. the analysis method according to any one of Claims 1 to 5, it is characterised in that in step (3), the addition of acetonitrile is the twice of reactant liquor volume.
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| CN106172391A (en) * | 2016-07-05 | 2016-12-07 | 南京科翼新材料有限公司 | A kind of agricultural builder containing sodium cocoyl glutamate |
| CN106442829A (en) * | 2016-12-13 | 2017-02-22 | 广州天赐高新材料股份有限公司 | Method of simultaneously detecting contents of fatty acid and active matter in fatty acyl neutral amino acid surfactant |
| CN106596767A (en) * | 2016-12-13 | 2017-04-26 | 广州天赐高新材料股份有限公司 | Method for quick determination of fatty acid residues in amino acid surfactants |
| CN106596768A (en) * | 2016-12-13 | 2017-04-26 | 广州天赐高新材料股份有限公司 | Liquid phase detection method for fatty acid residue in amino acid surfactant |
| CN106680402A (en) * | 2016-12-13 | 2017-05-17 | 广州天赐高新材料股份有限公司 | Detection method for fatty acid residues in potassium salt type amino acid surfactant |
| CN107722867A (en) * | 2017-11-06 | 2018-02-23 | 张永宏 | Static-free glue band electrostatic agent processing method |
| CN107759129A (en) * | 2017-11-20 | 2018-03-06 | 中建西部建设北方有限公司 | It is a kind of to be used to mix foaming agent of stone flour foam concrete and preparation method thereof |
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| CN110954602A (en) * | 2018-09-26 | 2020-04-03 | 伽蓝（集团）股份有限公司 | Cosmetic detection method |
| WO2023001267A1 (en) | 2021-07-23 | 2023-01-26 | 苏州欧丽特生物医药有限公司 | Supramolecular amino acid or salt thereof, and preparation method therefor and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3220883B1 (en) | 2014-11-18 | 2018-07-04 | Unilever PLC | Composition comprising salt of acyl glutamate as primary surfactant or primary anionic surfactant |
| CN106172391B (en) * | 2016-07-05 | 2020-04-07 | 南京科翼新材料有限公司 | Agricultural synergistic additive containing sodium cocoyl glutamate |
| CN106172391A (en) * | 2016-07-05 | 2016-12-07 | 南京科翼新材料有限公司 | A kind of agricultural builder containing sodium cocoyl glutamate |
| CN106442829A (en) * | 2016-12-13 | 2017-02-22 | 广州天赐高新材料股份有限公司 | Method of simultaneously detecting contents of fatty acid and active matter in fatty acyl neutral amino acid surfactant |
| CN106596767A (en) * | 2016-12-13 | 2017-04-26 | 广州天赐高新材料股份有限公司 | Method for quick determination of fatty acid residues in amino acid surfactants |
| CN106596768A (en) * | 2016-12-13 | 2017-04-26 | 广州天赐高新材料股份有限公司 | Liquid phase detection method for fatty acid residue in amino acid surfactant |
| CN106680402A (en) * | 2016-12-13 | 2017-05-17 | 广州天赐高新材料股份有限公司 | Detection method for fatty acid residues in potassium salt type amino acid surfactant |
| CN106596768B (en) * | 2016-12-13 | 2019-04-30 | 广州天赐高新材料股份有限公司 | The remaining liquid phase detection method of fatty acid in amino acid surfactant |
| CN107722867A (en) * | 2017-11-06 | 2018-02-23 | 张永宏 | Static-free glue band electrostatic agent processing method |
| CN107759129A (en) * | 2017-11-20 | 2018-03-06 | 中建西部建设北方有限公司 | It is a kind of to be used to mix foaming agent of stone flour foam concrete and preparation method thereof |
| CN110954602A (en) * | 2018-09-26 | 2020-04-03 | 伽蓝（集团）股份有限公司 | Cosmetic detection method |
| CN110954602B (en) * | 2018-09-26 | 2023-04-07 | 伽蓝（集团）股份有限公司 | Cosmetic detection method |
| WO2023001267A1 (en) | 2021-07-23 | 2023-01-26 | 苏州欧丽特生物医药有限公司 | Supramolecular amino acid or salt thereof, and preparation method therefor and application thereof |
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