CN106018660B - The assay method of alcohol ether content in alcohol ether carboxylate salt surfactant product - Google Patents
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Abstract
The assay method of alcohol ether content is by high performance liquid chromatography in a kind of alcohol ether carboxylate salt surfactant product, using raw material alcohol ether as reference substance, using the first alcohol and water for adding dressing agent as mobile phase, is detected with evaporative light scattering detector.This hair has the advantages that good detection efficiency height, accuracy, high sensitivity, applicability are wide.
Description
Technical field
The invention belongs to fine chemical product detection method, and in particular to a kind of alcohol ether carboxylate salt surfactant product
The assay method of middle alcohol ether content.
Background technology
Alcohol ether carboxylate salt surfactant (Alkylpolyethoxy Carboxylate, abbreviation AEC) is a kind of new
Multifunctional green anion surfactant, nontoxic, non-stimulated, easily biological-degradable, has both anion and non-ionic surface and lives
Property agent the characteristics of, have excellent decontamination, emulsification, dispersibility, acid and alkali-resistance, resistance to hard water, high temperature resistant, resistance to oxidation reducing agent,
Compatibility is good, cationic properties are not interfered with, particularly suitable for function equipment opaque products.From industrialization at the end of the 20th century with
Come, the application field of AEC has expanded to daily use chemicals, weaving, printing and dyeing, leather processing, metal processing, petroleum industry and family expenses cleaning etc.
Industry, application potential is huge, good market prospect.
AEC is produced, product can be divided into salt form or acid using alcohol ether as basic Material synthesis using carboxy methylation method or oxidizing process
Two class of type product, can be divided into various product series again according to different carbon chain lengths or different product designs.Although the life of AEC
Production. art complexity is various, and product category is different, but there are common evaluation between various processes, between various products classification
The conversion ratio height of standard, i.e. alcohol ether raw material, it is higher that conversion ratio more Gao Ze represents technological level, while product quality also can be therewith
Lifting, so evaluation of the measure of alcohol ether content for AEC production technologies and product quality is most important.
At present, the assay method of alcohol ether content generally uses ion exchange column chromatography method or diphasic titration in AEC, wherein
Ion exchange column chromatography method is cumbersome, takes and extremely grows, and assay method is larger to the subjective dependence of operating personnel, easily production
Raw error；And diphasic titration terminal is not easy to judge, easily it is subject to the interference of other materials or determination condition and false knot occurs
Fruit.So efficient, accurate assay method is developed into the necessary condition of AEC Product Quality Evaluations and process modification.
There is document once to carry out separation analysis [Guo Lin, analysis to AEC acid types product using reversed-phase ion-pair liquid chromatograph method
Chemistry, 2000,28 (4):407], but the separating degree of the exclusive peaks of AEC and alcohol ether is poor, and detection sensitivity is relatively low, measures effect
It is bad.
The content of the invention
The present invention provides the alcohol ether carboxylate salt surface that a kind of detection efficiency is high, accuracy is good, high sensitivity, applicability are wide
The assay method of alcohol ether content in active agent product.
The assay method of alcohol ether content is by efficient in alcohol ether carboxylate salt surfactant product provided by the invention
Liquid chromatography, using raw material alcohol ether as reference substance, using the first alcohol and water for adding dressing agent as mobile phase, is examined with evaporative light-scattering
Device is surveyed to be detected.Applicable product scope includes the alcohol ether carboxylate product salt with different adduction numbers of various carbochains, product
Molecular structure can use following general formula to represent：
R(OCH2CH2)n OCH2COOX
Wherein：R is C6-18Straight or branched alkyl；N is 2~12；X is H, Na+、K+、NH4 +, monoethanol amido, diethyl
Alcohol amido, Triethanolamine etc..
The assay method of the present invention includes the following steps：
(1) preparation of mobile phase：Eluted using binary solvent system, using methanol as organic phase, using meeting liquid phase
The water of chromatography requirement adds the alkaline dressing agent such as triethylamine, ammonium hydroxide as water phase in organic phase and a water phase at least phase
Its pH is adjusted to 8~10；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Using can
The C of alkali resistance condition18Reverse-phase chromatographic column is as carrier of separating；Eluted with prepared eluent gradient, elution program is：Binary
Solvent mixes, and the mixed solvent for being 60%~80% using methanol volume accounting is start gradient, by the time of 5min~20min
Linearly or nonlinearly it is changed into the final gradient that methanol volume accounting is 100% from start gradient, keeps 100% methanol coloured to institute
Spectral peak elution is complete；
(3) foundation of standard curve：According to alcohol ether carboxylate salt surfactant product classification, select corresponding
Alcohol ether raw material is then selected as reference substance, such as with tridecyl and ethylene oxide adduction number for 9 alcohol ether carboxylate product salt
Tridecyl and the C that ethylene oxide adduction number is 913EO9Alcohol ether is as reference substance；This reference substance adds ethanol to dissolve constant volume, prepares
0.1mg·mL-1~5mgmL-1Reference substance storage liquid, then dilution obtains the reference substance solution of series concentration respectively, and series is dense
Degree scope should match with detector sensitivity, and include at least 3 concentration values, control series product solution difference sample introduction, sample introduction
Amount is consistent, and records peak area；It is ordinate is linearly returned to numerical value as abscissa, peak area to numerical value using concentration
Return, obtain regression equation y=ax+c, wherein：Y is peak area logarithm, and x is log concentration, and a, c are constant, dependence among equations coefficient
It should be greater than 0.999；
(4) sample analysis：1~3 part of alcohol ether carboxylate sample is weighed, respectively plus ethanol prepares 2mgmL-1~20mgmL-1
Sample solution, closed ultrasonic extraction 1min~30min, puts to room temperature, shakes up up to sample solution, respectively sample introduction, sample size
It is consistent with reference substance, records peak area；
(5) external standard method calculates：Sample solution peak area is compared with the standard curve range of linearity, if being less than linear model
Enclose, then should increase sampling amount, if above the range of linearity, then should the amount of down-sampling, repeat samples analysis process, until sample is molten
Liquid peak area is in the range of linearity；Bring sample solution peak area into regression equation, the alcohol ether in sample solution is calculated
Content, the alcohol ether content in alcohol ether carboxylate surfactant product is obtained in conjunction with Mass Calculation is weighed.
It is of the invention to be had the following advantages compared with existing analysis method：
1. efficiently, compared with original ion exchange column chromatography method, analysis time is significantly saved.
2. accurate, assay method precision is high, and error range is small, and measurement result is more accurate.
3. high sensitivity, compared with existing chromatogram analysis method, target chromatographic peak separating degree is high, and interference is small,
The sensitivity of evaporative light scattering detector is of a relatively high, and detection limit is lower.
4. applicability is wide, the present invention is suitable for all kinds of alcohol ether carboxylate product salts, has the advantages that applicability is wide.
Brief description of the drawings
Fig. 1：With C16-18Alkyl, ethylene oxide adduction number are 12 AECH type product chromatography figures
Fig. 2：With C6-8Alkyl, ethylene oxide adduction number are 2 AEC ammonium salt type product chromatography figures
Fig. 3：With C12-14Alkyl, ethylene oxide adduction number are 9 AEC sodium-salt type product chromatography figures
Fig. 4：With C13Isomery alkyl, ethylene oxide adduction number are 9 AEC sylvite type product chromatography figures
Fig. 5：With C9-11Isomery alkyl, ethylene oxide adduction number are 6 AEC monoethanolamine salt form product chromatography
Figure.
Embodiment
Embodiment 1
With C16-18Alkyl, ethylene oxide adduction number be 12 AECH type products in alcohol ether content measure.
(1) preparation of mobile phase：Using methanol as organic phase, using the water of liquid chromatogram requirement is met as water phase,
Triethylamine is added in water phase its pH is adjusted to 8；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Use C18
Reverse-phase chromatographic column is as carrier of separating；Eluted with prepared eluent gradient, elution program is：Using methanol volume accounting as
80% mixed solvent start gradient, is linearly changed into the final ladder that methanol volume accounting is 100% by 5min from start gradient
Degree, keeps 100% methanol complete to the elution of all chromatographic peaks；
(3) foundation of standard curve：Select C16-18EO12As reference substance；This reference substance is weighed, is accurate to 0.0001g,
Ethanol is added to dissolve constant volume, compound concentration 0.502mgmL-1Reference substance solution, then dilution obtains concentration and is about respectively
0.251mg·mL-1、0.126mg·mL-1、0.0502mg·mL-1Reference substance solution, respectively 20 μ L of sample introduction, record peak area,
It is ordinate carries out linear regression to numerical value as abscissa, peak area to numerical value using concentration, to obtain regression equation be y=
(1.3627x+4.3376 R=0.9998)；
(4) sample analysis：Sample 0.1040g, 0.1143g, 0.1024g are weighed respectively, it is each plus ethanol 50.00mL, close
Ultrasonic extraction 10min is closed, is put to room temperature, is shaken up up to sample solution, 20 μ L of sample introduction, record peak area respectively；
(5) external standard method calculates：Bring sample peak area into regression equation, the C in sample solution is calculated16-18Alcohol ether contains
Amount, is 5.1% in conjunction with weighing Mass Calculation to obtain alcohol ether content average in alcohol ether carboxylate surfactant product.
Analyzed at the same time using ion exchange column chromatography method, measurement result, precision and measure duration contrast are as follows：
As it can be seen that two methods result is close, but assay method provided by the present invention can significantly save minute, and side
Method precision is far above ion exchange column chromatography method.
Embodiment 2
With C6-8Alkyl, ethylene oxide adduction number be 2 AEC ammonium salt type products in alcohol ether content measure.
(1) preparation of mobile phase：Eluted using binary solvent system, using methanol as organic phase, using meeting liquid phase
Methanol pH is adjusted to 9 by the water of chromatography requirement as water phase with ammonium hydroxide；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Use C18
Reverse-phase chromatographic column is as carrier of separating；Eluted with prepared eluent gradient, elution program is：Using methanol volume accounting as
60% mixed solvent is start gradient, be linearly changed into from start gradient by 20min methanol volume accounting be 100% it is final
Gradient, keeps 100% methanol complete to the elution of all chromatographic peaks；
(3) foundation of standard curve：Weigh C6-8EO2Alcohol ether 50.4mg, adds ethanol dissolving to be settled in 100mL volumetric flasks,
Compound concentration is 5.04mgmL-1Reference substance solution, then to obtain concentration be 2.52mgmL for dilution respectively-1、1.26mg·mL-1、1.01mg·mL-1、0.84mg·mL-1、0.0504mg·mL-1Reference substance solution, respectively sample introduction, 5 μ L of sample size, record
Peak area, is ordinate carries out linear regression to numerical value as abscissa, peak area to numerical value using concentration, obtains regression equation
For y=1.5891x+4.4231 (R=0.9992)；
(4) sample analysis：Alcohol ether carboxylate sample 0.4001g is weighed, adds ethanol 50.00mL, closed ultrasonic extraction
30min, puts to room temperature, shakes up up to sample solution, sample introduction, 5 μ L of sample size, records peak area；
(5) external standard method calculates：Bring sample peak area into regression equation, the alcohol ether content in sample solution be calculated,
It is 2.5% in conjunction with weighing Mass Calculation to obtain alcohol ether content in alcohol ether carboxylate surfactant product.
Use 0.0504mgmL-1Reference substance solution dilute step by step, observe signal-to-noise ratio, untill S/N=3, at this time
Alcohol ether concentration is 0.00101mgmL-1, detect and be limited to 5ng, [Guo Lin, is analyzed apparently higher than document for the sensitivity of the method for the present invention
Chemistry, 2000,28 (4):407] 0.1 μ g of report method.
Embodiment 3
With C12-14Alkyl, ethylene oxide adduction number be 9 AEC sodium-salt type products in alcohol ether content measure.
(1) preparation of mobile phase：Eluted using binary solvent system, using methanol as organic phase, using meeting liquid phase
The pH of first alcohol and water is adjusted to 10 by the water of chromatography requirement as water phase with triethylamine；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Using can
The C of alkali resistance condition18Column is analyzed；Eluted with prepared eluent gradient, elution program is：Using methanol volume accounting as
60% mixed solvent is start gradient, be linearly changed into from start gradient by 10min methanol volume accounting be 100% it is final
Gradient, keeps 100% methanol complete to the elution of all chromatographic peaks；
(3) foundation of standard curve：Weigh C12-14EO9Alcohol ether 120.2mg, adds ethanol to dissolve constant volume in 50mL volumetric flasks
In, compound concentration 2.404mgmL-1Reference substance solution, then to obtain concentration be 1.202mgmL for dilution respectively-1、
0.601mg·mL-1、0.4808mg·mL-1、0.2404mg·mL-1Reference substance solution, respectively sample introduction, sample size keep one
Cause, record peak area, be ordinate carries out linear regression to numerical value as abscissa, peak area to numerical value using concentration, obtain
Regression equation y=1.5296x+4.4851 (R=0.9999)；
(4) sample analysis：Alcohol ether carboxylate sample 0.2102g, 0.2089g are weighed, adds ethanol 50.00mL, closed ultrasonic
20min is extracted, is put to room temperature, shakes up and is consistent up to sample solution, difference sample introduction, sample size with reference substance, record peak face
Product；
(5) external standard method calculates：Bring sample peak area into regression equation, the alcohol ether content in sample solution be calculated,
It is 10.2% in conjunction with weighing Mass Calculation to obtain alcohol ether content average in alcohol ether carboxylate surfactant product.
Based on this product, the recovery test for being measured method is investigated, as a result as follows：
As it can be seen that the average recovery rate of assay method of the present invention is 99.0%, relative standard deviation is less than 3%, and method is accurate
Degree is good.
Embodiment 4
With C13Isomery alkyl, ethylene oxide adduction number be 9 AEC sylvite type products in alcohol ether content measure.
(1) preparation of mobile phase：Using methanol as organic phase, using the water of liquid chromatogram requirement is met as water phase,
Triethylamine is added in water phase its pH is adjusted to 8；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Using can
The C of alkali resistance condition18Reverse-phase chromatographic column is as carrier of separating；Eluted with prepared eluent gradient, elution program is：Below
It is volume accounting, using 65% methanol as start gradient, 0min~5min is 65% methanol, and 5.1min~10min is 85% first
Alcohol, 10.1min~20min are 100% methanol, keep 100% methanol complete to the elution of all chromatographic peaks；
(3) foundation of standard curve：Weigh C13EO9Alcohol ether makees 250.0mg, adds ethanol to dissolve constant volume in 100mL volumetric flasks
In, compound concentration 2.50mgmL-1Reference substance storage liquid, then to obtain concentration be 1.25mgmL for dilution respectively-1、
0.625mg·mL-1、0.500mg·mL-1Reference substance solution, respectively sample introduction, 20 μ L of sample size, record peak area, with concentration
Be to numerical value abscissa, peak area be to numerical value ordinate carry out linear regression, it is y=1.4617x+ to obtain regression equation
(4.3256 R=0.9993)；
(4) sample analysis：Sample 0.1050g, 0.1042g, 0.1103g are weighed, respectively adds ethanol 10.00mL, closed ultrasonic
1min is extracted, is put to room temperature, is shaken up up to sample solution, difference sample introduction, 20 μ L of sample size, record peak area；
(5) external standard method calculates：Bring sample peak area into regression equation, the C in sample solution is calculated13EO9Alcohol ether
Content, is 8.1% in conjunction with weighing Mass Calculation to obtain alcohol ether content average in alcohol ether carboxylate surfactant product.
Embodiment 5
With C9-11Isomery alkyl, ethylene oxide adduction number be 6 AEC monoethanolamine salt form products in alcohol ether content survey
It is fixed.
(1) preparation of mobile phase：Eluted using binary solvent system, using methanol as organic phase, using meeting liquid phase
The water of chromatography requirement is as water phase, its pH is adjusted to 8 by addition ammonium hydroxide in water phase；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Using can
The C of alkali resistance condition18Reverse-phase chromatographic column is as carrier of separating；Eluted with prepared eluent gradient, elution program is：With first
The mixed solvent that alcohol volume accounting is 80% is start gradient, and being linearly changed into methanol volume accounting from start gradient by 8min is
100% final gradient, keeps 100% methanol complete to the elution of all chromatographic peaks；
(3) foundation of standard curve：Weigh C9-11EO6Alcohol ether 48.0mg, adds ethanol to dissolve constant volume, and compound concentration is
0.480mg·mL-1Reference substance storage liquid, then to obtain concentration be 0.240mgmL for dilution respectively-1、0.120mg·mL-1、
0.0960mg·mL-1、0.08mg·mL-1、0.06mg·mL-1Reference substance solution, respectively 20 μ L of sample introduction, record peak area, with
Concentration be to numerical value abscissa, peak area be to numerical value ordinate carry out linear regression, obtain regression equation y=
(1.6812x+4.3332 R=0.9991)；
(4) sample analysis：Alcohol ether carboxylate sample 0.1545g is weighed, adds ethanol 50.00mL, closed ultrasonic extraction 5min,
Put to room temperature, shake up up to sample solution, 20 μ L of sample introduction, record peak area；
(5) external standard method calculates：Bring sample peak area into regression equation, the alcohol ether content in sample solution be calculated,
It is 4.5% in conjunction with weighing Mass Calculation to obtain alcohol ether content in alcohol ether carboxylate surfactant product.
Claims (4)
1. the assay method of alcohol ether content in a kind of alcohol ether carboxylate salt surfactant product, it is characterised in that including following step
Suddenly：
(1) preparation of mobile phase：Eluted using binary solvent system, using methanol as organic phase, using meeting liquid chromatogram
It is required that water as water phase, in organic phase and water mutually an at least phase add alkaline dressing agent is adjusted to 8~10 by its pH；
(2) chromatographic condition：It is measured using general liquid chromatographic system collocation evaporative light scattering detector；Use C18It is anti-phase
Chromatographic column is eluted, elution program is as carrier of separating with prepared eluent gradient：Binary solvent mixes, with methanol body
The mixed solvent that product accounting is 60%~80% is start gradient, by 5min~20min time by start gradient it is linear or
It is non-linear to be changed into the final gradient that methanol volume accounting is 100%, keep 100% methanol complete to the elution of all chromatographic peaks；
(3) foundation of standard curve：According to alcohol ether carboxylate salt surfactant product classification, corresponding alcohol ether is selected
For raw material as reference substance, this reference substance adds ethanol to dissolve constant volume, prepares 0.1mgmL-1~5mgmL-1Reference substance storage
Liquid, then dilution obtains the reference substance solution of series concentration respectively, series concentration scope should match with detector sensitivity, and extremely
3 concentration values, control series product solution difference sample introduction are included less, and sample size is consistent, and records peak area；With the logarithm of concentration
Be worth for abscissa, peak area be to numerical value ordinate carry out linear regression, obtain regression equation y=ax+c, wherein：Y is peak
Area logarithm, x are log concentration, and a, c are constant, and dependence among equations coefficient should be greater than 0.999；
(4) sample analysis：1~3 part of alcohol ether carboxylate sample is weighed, respectively plus ethanol prepares 2mgmL-1~20mgmL-1Sample
Product solution, closed ultrasonic extraction 1min~30min, puts to room temperature, shakes up up to sample solution, respectively sample introduction, sample size with it is right
It is consistent according to product, records peak area；
(5) external standard method calculates：Sample solution peak area is compared with the standard curve range of linearity, if being less than the range of linearity,
Sampling amount should then be increased, 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；Sample solution peak area is substituted into regression equation, the alcohol ether being calculated in sample solution contains
Amount, the alcohol ether content in alcohol ether carboxylate surfactant product is obtained in conjunction with Mass Calculation is weighed.
2. the assay method of alcohol ether content in a kind of alcohol ether carboxylate salt surfactant product as claimed in claim 1, its
It is characterized in that the 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 +, monoethanol amido, diethanol amine
Base, Triethanolamine.
3. the assay method of alcohol ether content in a kind of alcohol ether carboxylate salt surfactant product as claimed in claim 1, its
It is characterized in that the C18Reverse-phase chromatographic column is the C for being resistant to alkaline condition18Reverse-phase chromatographic column.
4. the assay method of alcohol ether content in a kind of alcohol ether carboxylate salt surfactant product as claimed in claim 1, its
It is characterized in that the alkaline dressing agent is triethylamine or ammonium hydroxide.
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| CN108152316B (en) * | 2017-12-14 | 2019-12-31 | 中国日用化学工业研究院 | Quality inspection method of glucoside sulfosuccinate product by taking maleic anhydride content and sulfonation rate as indexes |
| 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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