CN106018660A - Method for measuring content of alcohol ether in alkylpolyethoxy carboxylate surfactant product - Google Patents
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Abstract
A method for measuring content of alcohol ether in an alkylpolyethoxy carboxylate surfactant product is characterized by adopting the high-performance liquid chromatography, using raw alcohol ether as a reference control, adopting methanol and water which are added with modifiers as mobile phase, and using an evaporative light scattering detector to carry out detection. The method has the advantages of high detection efficiency, good accuracy, high sensitivity and high applicability.
Description
Technical field
The invention belongs to fine chemical product detection method, be specifically related to a kind of alcohol ether carboxylate salt surface activity
The assay method of alcohol ether content in agent product.
Background technology
Alcohol ether carboxylate salt surfactant (Alkylpolyethoxy Carboxylate is called for short AEC) is
The multifunctional green anion surfactant that one class is novel, nontoxic, non-stimulated, easily biological-degradable, has both
Anion and the feature of nonionic surfactant, have excellence decontamination, emulsifying, dispersibility, resistance to
Soda acid, resistance to hard water, high temperature resistant, resistance to oxidation reducing agent, compatibility is good, do not interfere with cationic properties,
It is particularly suited for function equipment opaque products.Since industrialization in 20 end of the centurys, the application of AEC expands
Exhibition to daily use chemicals, weave, print and dye, the process of leather processing, metal, the industry such as petroleum industry and domestic cleaning,
Application potential is huge, good market prospects.
AEC is Material synthesis based on alcohol ether, uses carboxy methylation method or oxidizing process to produce, and product can be divided into salt
Type or acid type product two class, can be divided into again multiple product according to different carbon chain lengths or different product designs
Series.Although the complex manufacturing of AEC is various, product category is different, but between various processes,
There is the conversion ratio height of common evaluation criterion, i.e. alcohol ether raw material between various product categories, conversion ratio is more
It is the highest that Gao Ze represents technological level, and product quality also can promote therewith simultaneously, so the mensuration of alcohol ether content is right
Most important in the evaluation of AEC production technology and product quality.
At present, in AEC, the assay method of alcohol ether content typically uses ion exchange column chromatography method or diphasic titration,
Wherein ion exchange column chromatography method complex operation, the longest, and the subjectivity of operator is depended on by assay method
Bad property is relatively big, easily produces error；And diphasic titration terminal be difficult to judge, be easily subject to other material or
The interference of condition determination and spurious results occurs.So, efficiently, accurately assay method be developed into AEC
Product Quality Evaluation and the essential condition of process modification.
Document is had once to use reversed-phase ion-pair liquid chromatograph method to carry out AEC acid type product separating analysis [Guo
Continuous heavy rain, analytical chemistry, 2000,28 (4): 407], but the exclusive peak of AEC is poor with the separating degree of alcohol ether, and inspection
Survey sensitivity is relatively low, measures poor effect.
Summary of the invention
The present invention provides the alcohol ether carboxylate that a kind of detection efficiency is high, accuracy is good, highly sensitive, the suitability is wide
The assay method of alcohol ether content in type surfactant product.
In the alcohol ether carboxylate salt surfactant product that the present invention provides, the assay method of alcohol ether content is to pass through
High performance liquid chromatography, using raw material alcohol ether as reference substance, with add dressing agent first alcohol and water for flowing phase,
Detect with evaporative light scattering detector.What the product scope being suitable for included various carbochain has different adduction
The alcohol ether carboxylate product salt of number, products molecule structure can represent with following formula:
R(OCH2CH2)n OCH2COOX
Wherein: R is C6-18Straight or branched alkyl；N is 2～12；X is H, Na+、K+、NH4 +, Dan Yi
Alcohol amido, diethanol amido, Triethanolamine etc..
The assay method of the present invention comprises the steps:
(1) preparation of the phase that flows: use binary solvent system eluting, uses methanol as organic facies, uses symbol
Close liquid chromatograph require water as aqueous phase, add in organic facies and an aqueous phase at least phase such as triethylamine,
Its pH regulator is 8～10 by the alkalescence dressing agent such as ammonia；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use can the C of alkali resistance condition18Reversed phase chromatographic column is as carrier of separating；With the eluent gradient eluting prepared,
Elution program is: binary solvent mixes, terraced for initiateing with the mixed solvent that methanol volume accounting is 60%～80%
Degree, linearly or nonlinearly being become methanol volume accounting through the time of 5min～20min from start gradient is 100%
Final gradient, keep 100% methanol to all chromatographic peak eluting complete；
(3) foundation of standard curve: according to alcohol ether carboxylate salt surfactant product classification, select phase therewith
Corresponding alcohol ether raw material as reference substance, such as, has tridecyl and oxirane adduction number is the alcohol ether of 9
Carboxylic acid salt product then selects tridecyl and oxirane adduction number to be the C of 913EO9Alcohol ether is as reference substance；This
Reference substance adds ethanol and dissolves constant volume, prepares 0.1mg mL-1～5mg mL-1Reference substance storage liquid, then distinguish
Dilution obtains the reference substance solution of series concentration, and series concentration scope should match with detector sensitivity, and
Including at least 3 concentration values, control series product solution sample introduction respectively, sample size keeps consistent, records face, peak
Long-pending；With the logarithm value of concentration as abscissa, the logarithm value of peak area carry out linear regression for vertical coordinate, obtain
Regression equation y=ax+c, wherein: y is peak area logarithm, x is log concentration, and a, c are constant,
Dependence among equations coefficient should be greater than 0.999；
(4) sample analysis: weigh alcohol ether carboxylate sample 1～3 parts, respectively adds ethanol preparation 2mg mL-1~
20mg·mL-1Sample solution, closed ultrasonic extract 1min～30min, put to room temperature, shake up and i.e. obtain sample
Solution, respectively sample introduction, sample size keeps consistent with reference substance, records peak area；
(5) external standard method calculates: by sample solution peak area compared with the standard curve range of linearity, if be less than
The range of linearity, then should strengthen sampling amount, if above the range of linearity, then should the amount of down-sampling, repeat samples
Analysis process, until sample solution peak area is in the range of linearity；Bring sample solution peak area into recurrence
Equation, the alcohol ether content being calculated in sample solution, obtain alcohol ether carboxylate in conjunction with weighing Mass Calculation
Alcohol ether content in surfactant product.
The present invention has the advantage that compared with existing analysis method
1. efficient, compared with original ion exchange column chromatography method, significantly save analysis time.
2. accurate, assay method precision is high, and range of error is little, and measurement result is more accurate.
The most highly sensitive, compared with existing chromatogram analysis method, aim colour spectral peak separating degree is high, disturbs little,
The sensitivity of evaporative light scattering detector is of a relatively high, and detection limit is lower.
4. the suitability is wide, and the present invention is applicable to all kinds of alcohol ether carboxylate product salt, has the advantage that the suitability is wide.
Accompanying drawing explanation
Fig. 1: there is C16-18Alkyl, oxirane adduction number is the AECH type product chromatography figure of 12
Fig. 2: there is C6-8Alkyl, oxirane adduction number is the AEC ammonium salt type product chromatography figure of 2
Fig. 3: there is C12-14Alkyl, oxirane adduction number is the AEC sodium-salt type product chromatography figure of 9
Fig. 4: there is C13Isomery alkyl, oxirane adduction number is the AEC potassium salt type product chromatography figure of 9
Fig. 5: there is C9-11Isomery alkyl, oxirane adduction number is the AEC monoethanolamine salt form product color of 6
Analysis of spectrum figure.
Detailed description of the invention
Embodiment 1
There is C16-18Alkyl, oxirane adduction number be 12 AECH type product in the mensuration of alcohol ether content.
(1) preparation of the phase that flows: use methanol as organic facies, use and meet the water conduct that liquid chromatograph requires
Aqueous phase, adding triethylamine in aqueous phase is 8 by its pH regulator；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use C18Reversed phase chromatographic column is as carrier of separating；With the eluent gradient eluting prepared, elution program is:
With the mixed solvent start gradient that methanol volume accounting is 80%, linearly become first from start gradient through 5min
Alcohol volume accounting is the final gradient of 100%, keeps 100% methanol complete to all chromatographic peak eluting；
(3) foundation of standard curve: select C16-18EO12As reference substance；Weigh this reference substance, be accurate to
0.0001g, adds ethanol and dissolves constant volume, and compound concentration is 0.502mg mL-1Reference substance solution, diluter
Release and obtain concentration and be about 0.251mg mL-1、0.126mg·mL-1、0.0502mg·mL-1Reference substance solution,
Respectively sample introduction 20 μ L, records peak area, with the logarithm value of concentration as abscissa, the logarithm value of peak area be vertical
Coordinate carries out linear regression, and obtaining regression equation is y=1.3627x+4.3376 (R=0.9998)；
(4) sample analysis: weigh sample 0.1040g, 0.1143g, 0.1024g respectively, each add ethanol
50.00mL, closed ultrasonic extracts 10min, puts to room temperature, shake up and i.e. obtain sample solution, respectively sample introduction 20 μ L,
Record peak area；
(5) external standard method calculates: bring sample peak area into regression equation, the C being calculated in sample solution16-18
Alcohol ether content, in conjunction with weighing the alcohol ether content that Mass Calculation obtains in alcohol ether carboxylate surfactant product
Average is 5.1%.
Using ion exchange column chromatography method to be analyzed, measurement result, precision and mensuration duration are to such as simultaneously
Under:
Visible, two kinds of methods and resultses are close, but assay method provided by the present invention can significantly save minute,
And method precision is far above ion exchange column chromatography method.
Embodiment 2
There is C6-8Alkyl, oxirane adduction number be 2 AEC ammonium salt type product in the mensuration of alcohol ether content.
(1) preparation of the phase that flows: use binary solvent system eluting, uses methanol as organic facies, uses symbol
Close water that liquid chromatograph requires as aqueous phase, be 9 with ammonia by methanol pH regulator；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use C18Reversed phase chromatographic column is as carrier of separating；With the eluent gradient eluting prepared, elution program is:
With methanol volume accounting be the mixed solvent of 60% as start gradient, linearly become from start gradient through 20min
Methanol volume accounting is the final gradient of 100%, keeps 100% methanol complete to all chromatographic peak eluting；
(3) foundation of standard curve: weigh C6-8EO2Alcohol ether 50.4mg, adds ethanol dissolving and is settled to 100mL appearance
In measuring bottle, compound concentration is 5.04mg mL-1Reference substance solution, then dilution obtains concentration and is respectively
2.52mg·mL-1、1.26mg·mL-1、1.01mg·mL-1、0.84mg·mL-1、0.0504mg·mL-1Right
According to product solution, sample introduction respectively, sample size 5 μ L, record peak area, with the logarithm value of concentration as abscissa,
The logarithm value of peak area is that vertical coordinate carries out linear regression, and obtaining regression equation is y=1.5891x+4.4231
(R=0.9992)；
(4) sample analysis: weigh alcohol ether carboxylate sample 0.4001g, add ethanol 50.00mL, closed ultrasonic
Extract 30min, put to room temperature, shake up and i.e. obtain sample solution, sample introduction, sample size 5 μ L, record peak area；
(5) external standard method calculates: bring sample peak area into regression equation, the alcohol ether being calculated in sample solution
Content, in conjunction with weighing the alcohol ether content that Mass Calculation obtains in alcohol ether carboxylate surfactant product be
2.5%.
Use 0.0504mg mL-1Reference substance solution stepwise dilution, observe signal to noise ratio, till S/N=3,
Now alcohol ether concentration is 0.00101mg mL-1, detection is limited to 5ng, and the sensitivity of the inventive method is the highest
The 0.1 μ g in document [Guo Lin, analytical chemistry, 2000,28 (4): 407] report method.
Embodiment 3
There is C12-14Alkyl, oxirane adduction number be 9 AEC sodium-salt type product in the mensuration of alcohol ether content.
(1) preparation of the phase that flows: use binary solvent system eluting, uses methanol as organic facies, uses symbol
The pH of first alcohol and water, as aqueous phase, is all adjusted to 10 with triethylamine by the water that conjunction liquid chromatograph requires；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use can the C of alkali resistance condition18Post is analyzed；With the eluent gradient eluting prepared, elution program is:
With methanol volume accounting be the mixed solvent of 60% as start gradient, linearly become from start gradient through 10min
Methanol volume accounting is the final gradient of 100%, keeps 100% methanol complete to all chromatographic peak eluting；
(3) foundation of standard curve: weigh C12-14EO9Alcohol ether 120.2mg, adds ethanol and dissolves constant volume in 50mL
In volumetric flask, compound concentration is 2.404mg mL-1Reference substance solution, then dilution obtains concentration and is respectively
1.202mg·mL-1、0.601mg·mL-1、0.4808mg·mL-1、0.2404mg·mL-1Reference substance solution,
Respectively sample introduction, sample size keeps consistent, records peak area, with the logarithm value of concentration as abscissa, peak area
Logarithm value be that vertical coordinate carries out linear regression, obtain regression equation y=1.5296x+4.4851
(R=0.9999)；
(4) sample analysis: weigh alcohol ether carboxylate sample 0.2102g, 0.2089g, add ethanol 50.00mL,
Closed ultrasonic extracts 20min, puts to room temperature, shakes up and i.e. obtain sample solution, respectively sample introduction, sample size with compare
Product keep consistent, record peak area；
(5) external standard method calculates: bring sample peak area into regression equation, the alcohol ether being calculated in sample solution
Content, in conjunction with weighing the alcohol ether content average that Mass Calculation obtains in alcohol ether carboxylate surfactant product
It is 10.2%.
Based on this product, the recovery test being measured method is investigated, and result is as follows:
Visible, the average recovery rate of assay method of the present invention is 99.0%, and relative standard deviation is less than 3%, method
Accuracy is good.
Embodiment 4
There is C13Isomery alkyl, oxirane adduction number be 9 AEC potassium salt type product in the mensuration of alcohol ether content.
(1) preparation of the phase that flows: use methanol as organic facies, use and meet the water conduct that liquid chromatograph requires
Aqueous phase, adding triethylamine in aqueous phase is 8 by its pH regulator；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use can the C of alkali resistance condition18Reversed phase chromatographic column is as carrier of separating；With the eluent gradient eluting prepared,
Elution program is: be volume accounting below, and with 65% methanol as start gradient, 0min～5min is 65%
Methanol, 5.1min～10min is 85% methanol, 10.1min～20min is 100% methanol, keeps 100% first
Alcohol is complete to all chromatographic peak eluting；
(3) foundation of standard curve: weigh C13EO9Alcohol ether makees 250.0mg, adds ethanol and dissolves constant volume in 100mL
In volumetric flask, compound concentration is 2.50mg mL-1Reference substance storage liquid, then dilution obtains concentration and is respectively
1.25mg·mL-1、0.625mg·mL-1、0.500mg·mL-1Reference substance solution, respectively sample introduction, sample size
20 μ L, record peak area, and with the logarithm value of concentration as abscissa, the logarithm value of peak area carries out for vertical coordinate
Linear regression, obtaining regression equation is y=1.4617x+4.3256 (R=0.9993)；
(4) sample analysis: weigh sample 0.1050g, 0.1042g, 0.1103g, respectively add ethanol 10.00mL,
Closed ultrasonic extracts 1min, puts to room temperature, shakes up and i.e. obtain sample solution, respectively sample introduction, sample size 20 μ L,
Record peak area；
(5) external standard method calculates: bring sample peak area into regression equation, the C being calculated in sample solution13EO9
Alcohol ether content, in conjunction with weighing the alcohol ether content that Mass Calculation obtains in alcohol ether carboxylate surfactant product
Average is 8.1%.
Embodiment 5
There is C9-11Isomery alkyl, oxirane adduction number be 6 AEC monoethanolamine salt form product in alcohol ether contain
The mensuration of amount.
(1) preparation of the phase that flows: use binary solvent system eluting, uses methanol as organic facies, uses symbol
The water that conjunction liquid chromatograph requires is as aqueous phase, and adding ammonia in aqueous phase is 8 by its pH regulator；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use can the C of alkali resistance condition18Reversed phase chromatographic column is as carrier of separating；With the eluent gradient eluting prepared,
Elution program is: with methanol volume accounting be the mixed solvent of 80% as start gradient, through 8min by initiateing
Gradient linearity becomes the final gradient that methanol volume accounting is 100%, keeps 100% methanol to all chromatographic peaks to wash
De-complete；
(3) foundation of standard curve: weigh C9-11EO6Alcohol ether 48.0mg, adds ethanol and dissolves constant volume, compound concentration
For 0.480mg mL-1Reference substance storage liquid, more respectively dilution to obtain concentration be 0.240mg mL-1、
0.120mg·mL-1、0.0960mg·mL-1、0.08mg·mL-1、0.06mg·mL-1Reference substance solution, point
Other sample introduction 20 μ L, records peak area, and with the logarithm value of concentration as abscissa, the logarithm value of peak area sits for vertical
Mark carries out linear regression, obtains regression equation y=1.6812x+4.3332 (R=0.9991)；
(4) sample analysis: weigh alcohol ether carboxylate sample 0.1545g, add ethanol 50.00mL, closed ultrasonic
Extract 5min, put to room temperature, shake up and i.e. obtain sample solution, sample introduction 20 μ L, record peak area；
(5) external standard method calculates: bring sample peak area into regression equation, the alcohol ether being calculated in sample solution
Content, in conjunction with weighing the alcohol ether content that Mass Calculation obtains in alcohol ether carboxylate surfactant product be
4.5%.
Claims (3)
1. the assay method of alcohol ether content in an alcohol ether carboxylate salt surfactant product, it is characterised in that include
Following steps:
(1) preparation of the phase that flows: use binary solvent system eluting, uses methanol as organic facies, uses symbol
Close liquid chromatograph require water as aqueous phase, add in organic facies and an aqueous phase at least phase such as triethylamine,
Its pH regulator is 8～10 by the alkalescence dressing agent such as ammonia；
(2) chromatographic condition: use general liquid chromatographic system collocation evaporative light scattering detector to be measured；
Use C18Reversed phase chromatographic column is as carrier of separating, and with the eluent gradient eluting prepared, elution program is:
Binary solvent mixes, with methanol volume accounting be the mixed solvent of 60%～80% as start gradient, through 5min～
The time of 20min is linearly or nonlinearly become the final gradient that methanol volume accounting is 100% from start gradient,
Keep 100% methanol complete to all chromatographic peak eluting；
(3) foundation of standard curve: according to alcohol ether carboxylate salt surfactant product classification, select phase therewith
Corresponding alcohol ether raw material is as reference substance, and this reference substance adds ethanol and dissolves constant volume, prepares 0.1mg mL-1~
5mg·mL-1Reference substance storage liquid, then dilution obtains the reference substance solution of series concentration, series concentration respectively
Scope should match with detector sensitivity, and including at least 3 concentration values, control series product solution is respectively
Sample introduction, sample size keeps consistent, records peak area；With the logarithm value of concentration as abscissa, peak area right
Numerical value is that vertical coordinate carries out linear regression, obtains regression equation y=ax+c, wherein: y is peak area logarithm,
X is log concentration, and a, c are constant, and dependence among equations coefficient should be greater than 0.999；
(4) sample analysis: weigh alcohol ether carboxylate sample 1～3 parts, respectively adds ethanol preparation 2mg mL-1~
20mg·mL-1Sample solution, closed ultrasonic extract 1min～30min, put to room temperature, shake up and i.e. obtain sample
Solution, respectively sample introduction, sample size keeps consistent with reference substance, records peak area；
(5) external standard method calculates: by sample solution peak area compared with the standard curve range of linearity, if be less than
The range of linearity, then should strengthen sampling amount, if above the range of linearity, then should the amount of down-sampling, repeat samples
Analysis process, until sample solution peak area is in the range of linearity；Bring sample solution peak area into recurrence
Equation, the alcohol ether content being calculated in sample solution, obtain alcohol ether carboxylate in conjunction with weighing Mass Calculation
Alcohol ether content in surfactant product.
The mensuration side of alcohol ether content in a kind of alcohol ether carboxylate salt surfactant product the most as claimed in claim 1
Method, it is characterised in that described alcohol ether carboxylate salt surfactant is below formula:
R(OCH2CH2)n OCH2COOX
Wherein: R is C6-18Straight or branched alkyl；N is 2～12；X is H, Na+、K+、NH4 +, Dan Yi
Alcohol amido, diethanol amido, Triethanolamine.
The mensuration side of alcohol ether content in a kind of alcohol ether carboxylate salt surfactant product the most as claimed in claim 1
Method, it is characterised in that described C18Reversed phase chromatographic column is can the C of alkali resistance condition18Reversed phase chromatographic column.
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| CN106404978A (en) * | 2016-11-11 | 2017-02-15 | 中国日用化学工业研究院 | Liquid chromatography analysis method of fatty alcohol polyoxyethylene ether composition distribution |
| 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 |
| CN110794048A (en) * | 2019-10-11 | 2020-02-14 | 宁波卫生职业技术学院 | High performance liquid detection method for alcamines cement grinding aid |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN110794048A (en) * | 2019-10-11 | 2020-02-14 | 宁波卫生职业技术学院 | High performance liquid detection method for alcamines cement grinding aid |
| CN110794048B (en) * | 2019-10-11 | 2022-08-23 | 宁波卫生职业技术学院 | High performance liquid detection method for alcamines cement grinding aid |
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| CN106018660B (en) | 2018-04-27 |
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