CN105675749B - The analysis method of cocoyl amino acid surfactant carbochain composition - Google Patents
The analysis method of cocoyl amino acid surfactant carbochain composition Download PDFInfo
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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
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Abstract
The present invention relates to a kind of analysis method of cocoyl amino acid surfactant carbochain composition, cocoyl amino acid/salt is first hydrolyzed and obtains coconut oil by this method, and HPLC analyses are carried out after derivatization.The analysis method of the present invention is not influenceed by amino acid surfactant species, as long as meet the type of fatty acid acylamino acid/salt；The present invention analysis method is simple to operate, low cost, sensitivity are high, do not influenceed by carbon chain lengths.
Description
Technical field
The present invention relates to chemical analysis technology field, more particularly to a kind of cocoyl amino acid surfactant carbon
The analysis method of chain composition.
Background technology
As a kind of typical fatty acid acylamino acid class surfactant, cocoyl amino acid/salt is with native amino
Acid, coconut oil are made for raw material.Excellent degradation property, extremely low toxicity and excitant makes it be applied to food, medicine, daily use chemicals
Etc. industry.In household chemicals field, cocoyl amino acid/salt has that antistatic, sterilizing ability, compatibility be good, resistance to hard water characteristic,
Various liquid, cream kind mildy wash, facial mask, skin care product, toothpaste, washing class articles for use, hair washing, shower can be widely used in
In the product such as dew and various perfumed soaps.
Cocoyl amino acid/salt is a kind of mixed amino-acid surfactant, mainly comprising octanoylamino acid/
It is salt, decanoylamino acid/salt, lauroyl amino acid/salt, myristoyl amino acid/salt, palmitoyl amino acid/salt, hard
The components such as matter acylamino acid/salt, wherein with lauroyl amino acid/salt content highest.Apparent different carbochain composition meeting
Significantly affect its surface-active：Firstth, the CMC value of each component is reduced with the extension of alkyl chain；Secondth, short carbon chain component rises
Bubble is fast and foam stabilizing is poor, and Long carbon chain component foaming slow and steady is soaked；3rd, each component to the viscosity of product formula, skin sense, compatibility
Property, even excitant have completely different contribution.Therefore, the complete carbochain ratio of monitoring cocoyl amino acid/salt seems
It is particularly important.
In order to detect the complete carbochain ratio of cocoyl amino acid/salt, Some Enterprises are using doing that direct HPLC is analyzed
Method, though this method is simple to operate can not to detect free aliphatic acid.In order to overcome this shortcoming, gas phase is developed later
The method of chromatogram (GC)：Cocoyl amino acid/salt complete hydrolysis is obtained into coconut oil first, then by coconut acid methylester or
GC analyses are carried out after ethyl esterified.But the method is hard to work for the analysis of Long carbon chain component.
The content of the invention
Based on this, it is an object of the invention to provide a kind of analysis of cocoyl amino acid surfactant carbochain composition
Method.
Specific technical scheme is as follows：
A kind of analysis method of cocoyl amino acid surfactant carbochain composition, comprises the following steps：
(1) cocoyl amino acid surfactant is dispersed in hydrochloric acid, it is cold after 3.5~4.5h of heating reflux reaction
But to room temperature, pH value is adjusted to 1.5~2.0；
(2) aliphatic acid in the reaction solution obtained with n-hexane extraction step (1), adds drier, crosses and filters after drying
Drier is removed, roto-vap operation is then carried out, obtains fatty acid extract, fatty acid extract and DMF are pressed 1:5~10
Mass ratio mixes to obtain DMF solution；
(3) alpha-brominated acetophenone and KF are accurately weighed, DMF is dissolved in, the DMF solution that step (2) is obtained is added, then in 95
15~25min is reacted at~105 DEG C, is cooled to after room temperature and adds acetonitrile, supernatant is taken after vibration, centrifugation；
(4) supernatant for obtaining step (3) carries out efficient liquid phase chromatographic analysis, produces.
In wherein some embodiments, the cocoyl amino acid surfactant is selected from：Cocoyl sarcosine,
Sodium Coco acylsarcosinate, cocoyl sarcosine potassium, cocoyl sarcosine triethanolamine salt, cocoyl glycine, coconut palm
Oleoyl Sodium Glycinate, cocoyl glycine potassium, cocoyl glycine triethanolamine salt, cocoyl alanine, cocounut oil
Acylalaninies sodium, cocoyl alanine potassium, cocoyl alanine triethanolamine salt, cocoyl glutamic acid, cocounut oil acyl
Base sodium glutamate, cocoyl disodium glutamate, cocoyl potassium glutamate, cocoyl glutamic acid triethanolamine salt or cocounut oil
Sulfonylmethyl sodium taurocholate.
In wherein some embodiments, in step (3), KF, alpha-brominated acetophenone and aliphatic acid mol ratio are 8~6:4
~3:1.
In wherein some embodiments, in step (4), the condition of high performance liquid chromatography is：
Chromatographic column：Anti-phase C18 posts；Column temperature：25~35 DEG C；254 ± 5nm of Detection wavelength；
Mobile phase：Mobile phase A is acetonitrile, and Mobile phase B is water, using gradient elution mode：From 0~15min, mobile phase A
Volume ratio with Mobile phase B is 65~75：35~25；From 15~40min, the percentage by volume of mobile phase A is become by 65~75%
Turn to 100%；Flow velocity is 0.8-1.2ml/min.
In wherein some embodiments, the condition of the high performance liquid chromatography is：
Chromatographic column：Anti-phase C18 posts；Column temperature：30℃；Detection wavelength 254nm；
Mobile phase：Mobile phase A is acetonitrile, and Mobile phase B is water, using gradient elution mode：From 0~15min, mobile phase A
Volume ratio with Mobile phase B is 70：30；From 15~40min, the percentage by volume of mobile phase A is become by 70% turns to 100%；Stream
Speed is 1.0ml/min.
In wherein some embodiments, the concentration of the hydrochloric acid in step (1) is 6.0mol/L.
In wherein some embodiments, drier described in step (2) is anhydrous sodium sulfate.
In wherein some embodiments, in step (3), the addition of acetonitrile is twice of reaction solution volume.
The principle of the present invention is as follows：
The analysis method of the present invention is that, first by cocoyl amino acid/salt complete hydrolysis, extraction obtains coconut oil, Ran Houyan
HPLC analyses are carried out after biochemistry.This method obtains fatty acid proportion and contributed including both sides：(1) active matter cocoyl amino
Acid/salt；(2) free coconut oil/salt.Missing inspection free coconut oil/salt when this method overcomes traditional technique in measuring carbochain ratio
Problem.
Specific step is：Cocoyl amino acid/salt is flowed back under the conditions of high-temperature strong acid first, the thorough water of amido link
Just aliphatic acid is can obtain after solution.Then obtained fatty section and bromoacetophenone are reacted under KF catalytic conditions, just can obtain
Aliphatic acid phenacyl ester.Obtained reaction solution is subjected to HPLC analyses, the mol ratio of different carbon chain component is just can obtain.Therefore from
Theoretically, ability is efficiently separated due to HPLC, this method can analyze cocoyl amino acid/salt sample of any carbochain composition
Product.
Beneficial effects of the present invention：
1st, first cocoyl amino acid/salt is hydrolyzed analysis method of the invention obtains coconut oil, and derivatization is laggard
Row HPLC is analyzed, and this method is not influenceed by amino acid surfactant species, as long as meet fatty acid acylamino acid/salt
Type；
2nd, analysis method of the invention is simple to operate, low cost, sensitivity are high, do not influenceed by carbon chain lengths.
Brief description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram of embodiment 1；
Fig. 2 is the high-efficient liquid phase chromatogram of embodiment 2.
Embodiment
The application is further elaborated by the following examples.
Embodiment 1：
A kind of HPLC analytical method of cocoyl Sodium L-alaninate carbochain composition of the present embodiment, including following step
Suddenly：
(1) 1.0g cocoyls Sodium L-alaninate (commercially available) is dispersed in 50mL 6N hydrochloric acid, heating is allowed to the 4h that flows back
Reaction solution is cooled to room temperature afterwards, with 32% liquid adjusting PH with base to 1.5~2.0；
(2) aliphatic acid in system is first extracted into (extraction three times, each 100mL n-hexanes), Ran Houyong with n-hexane
The extract that about 10g anhydrous sodium sulfate dryings are obtained, filters progress rotary evaporation after drier and obtains fatty acid extract, by it
Dissolve stand-by with 5mL DMF；
(3) the alpha-brominated acetophenones of 0.71g and 0.42g KF are weighed, is disperseed and stirred with 5mL DMF to add step after 1min
(2) DMF solution obtained (exists KF, alpha-brominated acetophenone and aliphatic acid mol ratio control：8~6:4~3:In the range of 1),
Then 20min is reacted under the conditions of placing reaction liquid into 100 DEG C.It is cooled to after room temperature and adds 20mL acetonitriles vibration about 1min,
About 5min is centrifuged under the conditions of 8000rpm takes supernatant to be measured；
(4) supernatant for obtaining step (3) carries out high-efficient liquid phase analysis, and actual conditions is as follows：
Chromatographic apparatus is configured：HPLC instrument (Japanese Shimadzu LC-20AD type chromatographs, Shimadzu CTO-10AS column ovens, Shimadzu
SPD-M20A PDADs)；Chromatogram records (Shimadzu LC solution work stations).
Chromatographic column：Agilent ZORBAX SB-C185μm 4.6*150mm
Column temperature：30℃.
Detection wavelength：254nm.
Mobile phase：B:Ultra-pure water, A:Acetonitrile.
Gradient condition：
Chromatogram is tested as shown in figure 1, carbochain composition is as shown in the table：
| 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 is worth noting that：The method that we determine peak by standard sample is carried out to the peak position that goes out of C8~C16 components
It is determined that, each retention time and peak area are as above represented for its.It is obvious that the relative scale by calculating each component peak area,
Just it can obtain the definite carbochain ratio of cocoyl Sodium L-alaninate sample.
Embodiment 2：
A kind of HPLC analytical method of cocoyl Sodium Glycinate carbochain composition of the present embodiment, including following step
Suddenly：
(1) 1.0g cocoyls Sodium Glycinate (commercially available) is dispersed in 50mL 6N hydrochloric acid, heating is allowed to the 4h that flows back
Reaction solution is cooled to room temperature afterwards, with 32% liquid adjusting PH with base to 1.5-2.0；
(2) aliphatic acid in system is first extracted into (extraction three times, each 100mL n-hexanes), Ran Houyong with n-hexane
The extract that about 10g anhydrous sodium sulfate dryings are obtained, filters progress rotary evaporation after drier and obtains oil-like extracts, used
5mL DMF dissolvings are stand-by；
(3) the alpha-brominated acetophenones of 0.75g and 0.44g KF are weighed, is disperseed and stirred with 5mL DMF to add step after 1min
(2) DMF solution obtained (controls KF, alpha-brominated acetophenone and aliphatic acid mol ratio 8~6:4~3:In the range of 1), so
After place reaction liquid into 100 DEG C under the conditions of react 20min.It is cooled to after room temperature and adds 20mL acetonitriles vibration about 1min,
About 5min is centrifuged under the conditions of 8000rpm takes supernatant to be measured；
(4) supernatant for obtaining step (3) carries out high-efficient liquid phase analysis, and actual conditions is as follows：
Chromatographic apparatus is configured：HPLC instrument (Japanese Shimadzu LC-20AD type chromatographs, Shimadzu CTO-10AS column ovens, Shimadzu
SPD-M20A PDADs)；Chromatogram records (Shimadzu LC solution work stations).
Chromatographic column：Agilent ZORBAX SB-C185μm 4.6*150mm
Column temperature：30℃.
Detection wavelength：254nm.
Mobile phase：B:Ultra-pure water, A:Acetonitrile.
Gradient condition：
Chromatogram is tested as shown in Fig. 2 carbochain composition is as shown in the table：
| 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 is worth noting that：The method that we determine peak by standard sample is carried out to the peak position that goes out of C8~C16 components
It is determined that, each retention time and peak area are as above represented for its.It is obvious that the relative scale by calculating each component peak area,
Just it can obtain the definite carbochain ratio of cocoyl Sodium Glycinate sample.
Each technical characteristic of embodiment described above can be combined arbitrarily, to make description succinct, not to above-mentioned reality
Apply all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, the scope of this specification record is all considered to be.
Embodiment described above only expresses the several embodiments of the present invention, and it describes more specific and detailed, but simultaneously
Can not therefore it be construed as limiting the scope of the patent.It should be pointed out that coming for one of ordinary skill in the art
Say, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the protection of the present invention
Scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (8)
1. a kind of analysis method of cocoyl amino acid surfactant carbochain composition, it is characterised in that including following step
Suddenly：
(1) cocoyl amino acid surfactant is dispersed in hydrochloric acid, be cooled to after 3.5~4.5h of heating reflux reaction
Room temperature, adjusts pH value to 1.5~2.0；
(2) aliphatic acid in the reaction solution obtained with n-hexane extraction step (1), adds drier, is filtered to remove after drying dry
Drying prescription, then carries out roto-vap operation, obtains fatty acid extract, and fatty acid extract and DMF are pressed into 1:5~10 quality
Than mixing to obtain DMF solution；
(3) alpha-brominated acetophenone and KF are accurately weighed, DMF is dissolved in, the DMF solution that step (2) is obtained is added, then in 95~
15~25min is reacted at 105 DEG C, is cooled to after room temperature and adds acetonitrile, supernatant is taken after vibration, centrifugation；
(4) supernatant for obtaining step (3) carries out efficient liquid phase chromatographic analysis, produces.
2. analysis method according to claim 1, it is characterised in that the cocoyl amino acid surfactant choosing
From：Cocoyl sarcosine, Sodium Coco acylsarcosinate, cocoyl sarcosine potassium, cocoyl sarcosine triethanolamine salt,
Cocoyl glycine, cocoyl Sodium Glycinate, cocoyl glycine potassium, cocoyl glycine triethanolamine salt, coconut palm
Oleoyl alanine, cocoyl Sodium L-alaninate, cocoyl alanine potassium, cocoyl alanine triethanolamine salt, cocounut oil
Acyl glutamic acid, sodium cocoyl glutamate, cocoyl disodium glutamate, cocoyl potassium glutamate, cocoyl paddy ammonia
Triethylenetetraminehexaacetic acid alcohol amine salt or sodium cocoyl methyl sodium taurocholate.
3. analysis method according to claim 1, it is characterised in that in step (3), KF, alpha-brominated acetophenone and fat
The mol ratio of 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 posts；Column temperature：25~35 DEG C；254 ± 5nm of Detection wavelength；
Mobile phase：Mobile phase A is acetonitrile, and Mobile phase B is water, using gradient elution mode：From 0~15min, mobile phase A and stream
Dynamic phase B volume ratio is 65~75：35~25；From 15~40min, the percentage by volume of mobile phase A is become by 65~75% to be turned to
100%；Flow velocity is 0.8~1.2ml/min.
5. analysis method according to claim 4, it is characterised in that the condition of the high performance liquid chromatography is：
Chromatographic column：Anti-phase C18 posts；Column temperature：30℃；Detection wavelength 254nm；
Mobile phase：Mobile phase A is acetonitrile, and Mobile phase B is water, using gradient elution mode：From 0~15min, mobile phase A and stream
Dynamic phase B volume ratio is 70：30；From 15~40min, the percentage by volume of mobile phase A is become by 70% turns to 100%；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), the drier 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
For twice of reaction solution volume.
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| DE202015009054U1 (en) | 2014-11-18 | 2016-08-05 | Unilever N.V. | A composition comprising salt of acyl glutamate as a 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 |
| 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 |
| 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 |
| CN106442829B (en) * | 2016-12-13 | 2018-01-02 | 广州天赐高新材料股份有限公司 | It is a kind of while detect the method for aliphatic acid and active matter content in fatty acyl neutral 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 |
| 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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| CN102338790B (en) * | 2011-08-24 | 2014-07-09 | 上海奥利实业有限公司 | Method for measuring fatty acid soap in amino acid surface active agent |
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