CN107840928A - The preparation method of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, nonyl phenol and bisphenol A molecular engram post and its application - Google Patents
The preparation method of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, nonyl phenol and bisphenol A molecular engram post and its application Download PDFInfo
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Abstract
The invention discloses the preparation method of a kind of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, including interaction, polymerisation, the step such as removal of microsphere occur for microsphere and function monomer；The invention also discloses a kind of nonyl phenol and bisphenol A molecular engram post, the filler of the molecular blotting column is nonyl phenol and bisphenol-A double-template molecularly imprinted polymer.Nonyl phenol and bisphenol A molecular engram post provided by the present invention, can specific adsorption nonyl phenol and bisphenol-A；Invention also discloses a kind of application of nonyl phenol and bisphenol A molecular engram post, and it can be applied to detect the nonyl phenol and bisphenol-A in food, it is not necessary to using Internal standard, reduce cost；Detection efficiency is high, and recovery of extraction is solved because bisphenol-A and nonyl phenol content are relatively low up to more than 90%, matrix is various, serious interference and can not simultaneously by bisphenol-A and nonyl phenol extraction and cleaning the problem of.The present invention is applied to nonyl phenol and bisphenol A molecular engram post and its application.
Description
Technical field
The present invention relates to a kind of molecular blotting column, the specially system of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer
Preparation Method, nonyl phenol and bisphenol A molecular engram post and its application.
Background technology
Nonyl phenol（nonylphenol,NP）Be widely used in industrially prepared synthetic detergent, humidizer, lube oil additive,
Plasticizer etc., it is pollutant widely distributed in environment, investigation at present finds that NP is prevalent in varieties of food items.NP is a kind of
Incretion interferent, there is estrogenlike activity, toxic action can be produced to body, it is to ill-effect caused by organism
Influence and tumor promotion including Endocrine system, reproductive system and immune system.
Bisphenol-A（BisphenolA ,BPA）For producing the materials such as makrolon, it is widely used in food box and beverage bottle
Deng packaging material.Bisphenol-A is entered in Foods or drinkses by packaging material for food, and then enters human body, can cause reproductive organs
Exception, male is feminized, tissue canceration can also be triggered.
Therefore, it is necessary to be monitored to nonyl phenol pollution condition in dairy products, and environment, packaging material, raw material are strengthened
The monitoring of breast, eliminate and reduce the pollution of phenols endocrine disruptors in dairy product manufacturing process.Food safety supervision inspection and
It is 2-73 file attachments that risk supervision, which specifies the method for inspection,《The detection high performance liquid chromatography of bisphenol-A and nonyl phenol in food-
Tandem mass spectrometry》, this method need to use gel permeation chrommatograph grease removal to purify, be quantified using Isotopic Internal Standard, and Isotopic Internal Standard price is high,
Testing cost is high.Detection time is grown, and handles 10 samples daily using exclusion chromatography, it is impossible to meets risk requirements of plan, needs
Establish quick and easy method.
The content of the invention
To solve the above-mentioned problems in the prior art, the present invention is intended to provide a kind of nonyl phenol and bisphenol-A double-template
The preparation method of molecularly imprinted polymer, corresponding nonyl phenol and bisphenol A molecular engram post and its application, it is existing can solve the problem that
Above mentioned problem present in technology.
To achieve the above object, used technical scheme is as follows by the present invention：
A kind of preparation method of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, the preparation method is according to following step
Order is carried out：
（1）Microsphere interacts with function monomer
Nonyl phenol analog and bisphenol-A analog are imprint molecule, and methacrylic acid is function monomer；
0.1-1mmol nonyl phenols analog, 0.1-1mmol bisphenol-A analogs are dissolved in 0.5-5ml chloroforms, add volume
For 4-5 times of methacrylic acid of chloroform volume, low temperature is placed after supersound process；
（2）Polymerisation
To step（1）0.1-0.5mmol n-dodecanes, 0.1-0.5mmol surfactants, 10- are added in gained mixture
30ml polyethylene glycol diacrylates methyl esters, 0.01-0.1g azodiisobutyronitriles and 20-60ml ultra-pure waters, ultrasound after being well mixed
15-30min is handled, nitrogen 10-15min is passed through, is then sonicated 8-15min, said mixture is formed the breast of isotropic stable
Liquid, in 90 DEG C of stirring reactions, obtain milky polymer beads；
（3）The removal of microsphere
Dry after the milky polymer beads are filtered by vacuum, sieved after mechanical lapping；
After polymer beads after above-mentioned grinding is sieved are washed repeatedly repeatedly with second alcohol and water respectively, then it is more with formic acid-methanol
Secondary washing, until can't detect nonyl phenol analog and bisphenol-A analog, again with methanol is washed to neutrality, produce nonyl phenol and
Bisphenol-A double-template molecularly imprinted polymer.
As restriction, step（1）In, the mol ratio of nonyl phenol analog and bisphenol-A analog is 1:1.
Limited as further：
Step（1）It is 2-8 DEG C that middle low temperature, which places temperature, standing time 12-16h；
Step（2）The mol ratio of middle n-dodecane and surfactant is 1:1；
Step（2）The middle stirring reaction time is 20-24h.
Step（3）Described in formic acid-methanol concentration be 2%, formic acid is solute, and methanol is solvent.
Present invention also offers a kind of nonyl phenol and bisphenol A molecular engram post, its filler is nonyl phenol and bisphenol-A bimodulus
Plate molecularly imprinted polymer, bisphenol-A double-template molecularly imprinted polymer, wherein the bisphenol-A double-template molecularly imprinted polymer
As obtained by the preparation method of foregoing nonyl phenol and bisphenol-A double-template molecularly imprinted polymer.
Present invention provides the application of above-mentioned nonyl phenol and bisphenol A molecular engram post, and it can be applied to detect in food
Nonyl phenol and bisphenol-A.
As restriction, the food is dairy products.
Limited as further, nonyl phenol and the bisphenol A molecular engram post is applied to the nonyl in detection dairy products
The method of phenol and bisphenol-A, including the following steps that order is carried out：
（1）Sample is weighed in GPC loading pipes, adds acetonitrile, vortex mixes, ultrasonic extraction, centrifuging and taking supernatant；
（2）By step（1）Gained supernatant crosses nonyl phenol and bisphenol A molecular engram post, is cleaned with ultra-pure water, decompressing and extracting, uses
Methanol is eluted, and centrifugation, supernatant liquor is detected using honest chromatogram-tandem mass spectrometer.
Compared with prior art, acquired technological progress is the present invention：
（1）The nonyl phenol and bisphenol A molecular engram post of the present invention, its filler is nonyl phenol and bisphenol-A double-template molecular engram
Polymer, the polymer have adsorption capacity height, the characteristic of uniform particle diameter；The molecular blotting column as made from polymer filling can
Specific adsorption nonyl phenol and bisphenol-A；
（2）The nonyl phenol and bisphenol A molecular engram post of the present invention can be applied to the detection of nonyl phenol and bisphenol-A in food, use
External standard method need not use Internal standard, simpler relative to internal standard method, and internal standard expense is very high, if general method
When less accurate or loss is bigger, using internal standard method, interior target side can not be used if using external standard accuracy height
Method is carried out.Therefore, present invention reduces cost；Detection efficiency is high, recovery of extraction up to more than 90%, solve because bisphenol-A and
Nonyl phenol content is relatively low, matrix is various, serious interference and can not simultaneously by bisphenol-A and nonyl phenol extraction and cleaning the problem of, and protect
Demonstrate,prove being remained without background for molecular blotting column；
To sum up, the present invention is applied to nonyl phenol and bisphenol A molecular engram post and its application.
Embodiment
The preferred embodiments of the present invention are illustrated below.It should be appreciated that preferred embodiment described herein is only used
In the description and interpretation present invention, it is not intended to limit the present invention.
A kind of 1 nonyl phenol of embodiment and bisphenol A molecular engram post
A kind of nonyl phenol and bisphenol A molecular engram post, its filler are nonyl phenol and bisphenol-A double-template molecularly imprinted polymer.
Wherein：
Nonyl phenol and bisphenol-A double-template molecularly imprinted polymer are made as follows：
（1）Microsphere interacts with function monomer
Nonyl phenol analog and bisphenol-A analog are imprint molecule, and methacrylic acid is function monomer；
1mmol nonyl phenols analog, 1mmol bisphenol-A analogs are dissolved in 5ml chloroforms, add 25ml methacrylic acid, ultrasound
After processing after 45min, 4 DEG C of placement 15h；
（2）Polymerisation
To step（1）0.5mmol n-dodecanes, 0.5mmol surfactants, 30ml polyethylene glycol two are added in gained mixture
Methyl acrylate, 0.03g azodiisobutyronitriles and 60ml ultra-pure waters, 30min is ultrasonically treated after well mixed, is passed through nitrogen
15min, 15min is then sonicated, said mixture is formed the emulsion of isotropic stable, in 90 DEG C of stirring reaction 24h, obtain breast
White poiymer partides；
（3）The removal of microsphere
Dry after the milky polymer beads are filtered by vacuum, sieved after mechanical lapping；
Polymer beads after above-mentioned grinding is sieved first are washed with the ethanol of 10 times of volumes, then the water washing with 10 times of volumes,
Wash 5 times repeatedly successively；
Formic acid-the methanol solution for being again 2% with the concentration of 10 times of volumes（Formic acid is solute, and methanol is solvent）Wash repeatedly, until
UV-detector can't detect nonyl phenol analog and bisphenol-A analog；
Washed with methanol to neutrality, produce nonyl phenol and bisphenol-A double-template molecularly imprinted polymer.
Embodiment 2-5 nonyl phenols and bisphenol A molecular engram post
Embodiment 2-5 is respectively a kind of nonyl phenol and bisphenol A molecular engram post, and their filler is nonyl phenol and bisphenol-A bimodulus
Plate molecularly imprinted polymer, the wherein preparation method of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer and the phase of embodiment 1
Closely, their differing only in embodiment 1, relevant parameter is different, specifically see the table below：
The application of the nonyl phenol of embodiment 6 and bisphenol A molecular engram post
Nonyl phenol and bisphenol A molecular engram post can be applied to detect the nonyl phenol and bisphenol-A in food, and Cleaning Principle is：Sample
Extracted by acetonitrile, through molecular engram column purification, isotopic dilution high performance liquid chromatography-tandem mass technology for detection, with standard
Series of comparisons quantifies.
Nonyl phenol and bisphenol A molecular engram post can be applied to detect the liquid milks such as liquid milk, lactogenesis, acidified milk, milk beverage
Nonyl phenol and bisphenol-A in product, including the following steps that order is carried out：
Sample 1.0-2.0g directly is weighed in GPC loading pipes, adds 6ml acetonitriles, and vortex mixes, ultrasonic extraction 15min, in 4
DEG C, 5000r/min centrifugation 10min, supernatant is poured into Erlenmeyer flask, add 9ml ultra-pure waters, mix, all cross nonyl
Phenol and bisphenol A molecular engram post, are cleaned, decompressing and extracting with 5ml ultra-pure waters, are eluted with 3ml methanol, 5000r/min centrifugation 5min,
Supernatant liquor is detected using honest chromatogram-tandem mass spectrometer.
Nonyl phenol and bisphenol A molecular engram post can be applied to detect the nonyl in the powdery dairy produces such as milk powder, PURE WHEY
Base phenol and bisphenol-A, including the following steps that order is carried out：
Directly weigh in sample 1.0g and GPC loading pipes, add 6ml acetonitriles, vortex mixes, ultrasonic extraction 15min, in 4 DEG C,
5000r/min centrifuges 10min, and supernatant is poured into Erlenmeyer flask, then repeats extraction once with 2% acetic acid acetonitrile, and merging carries
Liquid is taken, adds 18ml ultra-pure waters, is mixed, nonyl phenol and bisphenol A molecular engram post is all crossed, is cleaned with 5ml ultra-pure waters, is depressurized
Drain, eluted with 3ml methanol, 5000r/min centrifugation 5min, supernatant liquor is examined using honest chromatogram-tandem mass spectrometer
Survey.
Instrument and equipment：Type high performance liquid chromatograph-AB 4000QTrip the tandem mass spectrometers of Agilent 1260；Analyze day
It is flat；Turbula shaker；Refrigerated centrifuge；Molecular blotting column；Ultrasonic wave.
Reagent：Nonyl phenol；Bisphenol-A；Chromatographic Pure Methanol；Trifluoroacetic acid aqueous solution；Ethyl acetate；Hexamethylene.
Chromatographic condition：
Chromatographic column：C18 posts, 2.7 μm, 100mm × 3.0mm or with equal performance chromatographic column；
Trapping column：C18 posts, 2.7 μm, 50mm × 4.6mm, trapping column is located at before sampling valve；
Column temperature：30℃；
Flow velocity：300μL/min；
Sample size：10μL；
Run time：18min；
Condition of gradient elution：
Mass Spectrometry Conditions：
Ionization mode：ES（-）；
Detection mode:More reaction detections；
Gas curtain gas：30L/min；
Spray voltage：-4500V；
Remove solubility temperature：550℃；
Mass spectrum optimal conditions：
To determine the applicable linearly interval of this method, the range of linearity of design experiment assay method.Required according to method, use methanol
It is respectively 10ng/mL, 20ng/mL, 50ng/mL, 100ng/mL, 200ng/mL, 500ng/mL to prepare nonyl phenol and content of bisphenol A
The directly upper machine measure of standard curve, empirical tests meet Lambert-Beer's law.
Finally it should be noted that：The preferred embodiments of the present invention are the foregoing is only, are not intended to limit the invention,
Although the present invention is described in detail with reference to the foregoing embodiments, for those skilled in the art, it still may be used
To be modified to the technical scheme described in foregoing embodiments, or equivalent substitution is carried out to which part technical characteristic.
All any modification, equivalent substitution and improvements within the spirit and principle of content described by claims of the present invention, made
Deng should be included in the protection domain of the claims in the present invention.
Claims (10)
1. the preparation method of a kind of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, it is characterised in that the preparation method is pressed
Carried out according to following step order：
（1）Microsphere interacts with function monomer
Nonyl phenol analog and bisphenol-A analog are imprint molecule, and methacrylic acid is function monomer；
0.1-1mmol nonyl phenols analog, 0.1-1mmol bisphenol-A analogs are dissolved in 0.5-5ml chloroforms, addition volume is chlorine
The methacrylic acid of 4-5 times of volume is imitated, low temperature is placed after supersound process；
（2）Polymerisation
To step（1）0.1-0.5mmol n-dodecanes, 0.1-0.5mmol surfactants, 10- are added in gained mixture
30ml polyethylene glycol diacrylates methyl esters, 0.01-0.1g azodiisobutyronitriles and 20-60ml ultra-pure waters, ultrasound after being well mixed
15-30min is handled, nitrogen 10-15min is passed through, is then sonicated 8-15min, said mixture is formed the breast of isotropic stable
Liquid, in 90 DEG C of stirring reactions, obtain milky polymer beads；
（3）The removal of microsphere
Dry after the milky polymer beads are filtered by vacuum, sieved after mechanical lapping；
After polymer beads after above-mentioned grinding is sieved are washed repeatedly repeatedly with second alcohol and water respectively, then it is more with formic acid-methanol
Secondary washing, until can't detect nonyl phenol analog and bisphenol-A analog, again with methanol is washed to neutrality, produce nonyl phenol and
Bisphenol-A double-template molecularly imprinted polymer.
2. the preparation method of nonyl phenol according to claim 1 and bisphenol-A double-template molecularly imprinted polymer, its feature exist
In：The step（1）In, the mol ratio of nonyl phenol analog and bisphenol-A analog is 1:1.
3. the preparation method of nonyl phenol according to claim 1 and bisphenol-A double-template molecularly imprinted polymer, its feature exist
In：The step（1）It is 2-8 DEG C that middle low temperature, which places temperature, standing time 12-16h.
4. the preparation method of nonyl phenol according to claim 1 and bisphenol-A double-template molecularly imprinted polymer, its feature exist
In：The step（2）The mol ratio of middle n-dodecane and surfactant is 1:1.
5. the preparation method of nonyl phenol according to claim 1 and bisphenol-A double-template molecularly imprinted polymer, its feature exist
In：The step（2）The middle stirring reaction time is 20-24h.
6. the preparation method of nonyl phenol according to claim 1 and bisphenol-A double-template molecularly imprinted polymer, its feature exist
In：The step（3）Described in formic acid-methanol concentration be 2%, formic acid is solute, and methanol is solvent.
7. a kind of nonyl phenol and bisphenol A molecular engram post, it is characterised in that：Nonyl phenol and the bisphenol A molecular engram post is filled out
Material, is nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, wherein the bisphenol-A double-template molecularly imprinted polymer is by weighing
Profit is required obtained by the preparation method of the nonyl phenol and bisphenol-A double-template molecularly imprinted polymer any one of 1-6.
8. the application of nonyl phenol according to claim 7 and bisphenol A molecular engram post, it is characterised in that：The nonyl phenol
It can be applied to detect the nonyl phenol and bisphenol-A in food with bisphenol A molecular engram post.
9. the application of nonyl phenol according to claim 8 and bisphenol A molecular engram post, it is characterised in that：The food
Product are dairy products.
10. the application of nonyl phenol according to claim 8 and bisphenol A molecular engram post, it is characterised in that：The nonyl phenol
It is applied to detect the method for the nonyl phenol and bisphenol-A in dairy products with bisphenol A molecular engram post, includes the following step that order is carried out
Suddenly：
（1）Sample is weighed in GPC loading pipes, adds acetonitrile, vortex mixes, ultrasonic extraction, centrifuging and taking supernatant；
（2）By step（1）Gained supernatant crosses nonyl phenol and bisphenol A molecular engram post, is cleaned with ultra-pure water, decompressing and extracting, uses
Methanol is eluted, and centrifugation, supernatant liquor is detected using honest chromatogram-tandem mass spectrometer.
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| CN201711162911.4A CN107840928A (en) | 2017-11-21 | 2017-11-21 | The preparation method of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, nonyl phenol and bisphenol A molecular engram post and its application |
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| CN201711162911.4A CN107840928A (en) | 2017-11-21 | 2017-11-21 | The preparation method of nonyl phenol and bisphenol-A double-template molecularly imprinted polymer, nonyl phenol and bisphenol A molecular engram post and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102911306A (en) * | 2012-10-10 | 2013-02-06 | 肇庆学院 | Bisphenol-A and nonylphenol double-template molecularly imprinted polymeric microspheres |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102911306A (en) * | 2012-10-10 | 2013-02-06 | 肇庆学院 | Bisphenol-A and nonylphenol double-template molecularly imprinted polymeric microspheres |
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Application publication date: 20180327 |