CN102372821A - Dibutyl phthalate molecularly imprinted polymer (DBP-MIP) and preparation method thereof - Google Patents

Dibutyl phthalate molecularly imprinted polymer (DBP-MIP) and preparation method thereof Download PDF

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CN102372821A
CN102372821A CN2010102648059A CN201010264805A CN102372821A CN 102372821 A CN102372821 A CN 102372821A CN 2010102648059 A CN2010102648059 A CN 2010102648059A CN 201010264805 A CN201010264805 A CN 201010264805A CN 102372821 A CN102372821 A CN 102372821A
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witcizer
molecularly imprinted
imprinted polymer
template molecule
dbp
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孙姝琦
张颖
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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Abstract

The invention provides a dibutyl phthalate molecularly imprinted polymer (DBP-MIP) and a preparation method thereof, belonging to the technical field of analytical chemistry. The DBP-MIP is prepared by dissolving a template molecule DBP, a functional monomer methacrylic acid and a crosslinking agent ethylene glycol dimethacrylate into a porogen chloroform or acetonitrile, adding an initiator azobisisobutyronitrile, filling nitrogen to remove oxygen, carrying out initiated polymerization at 55-75 DEG C, and grinding, sieving and washing a polymer after completing reaction. An MIP solid phase extraction column can highly selectively separate and enrich DBP in samples such as environment, food, chemical products and the like and effectively remove matrix interference.

Description

A kind of Witcizer 300 molecularly imprinted polymer and preparation method thereof
Technical field
The present invention relates to a kind of technique of analytical chemistry method, be specially a kind of Witcizer 300 molecularly imprinted polymer and preparation method thereof.
Background technology
Witcizer 300 (dibutyl phthalate, DBP), mainly as industrial softening agent, and the raw materials for production of farm chemical carrier, wormer, makeup, fragrance article, lubricant and defoaming agents etc.DBP extensively is present in the physical environments such as atmosphere, water body, soil, organism along with industrial production constantly gets into environment, has become one of the most general global pollutent.DBP is a kind of important environment incretion interferent, and similar female hormone seriously disturbs human and animal's endocrine system, particularly reproductive function, has carcinogenic, teratogenesis and mutagenic possible, has therefore caused people's great attention.
One of European Union, the U.S. and China all monitor DBP as needs environmental pollutant.Bibliographical information mainly is methods such as vapor-phase chromatography, liquid phase chromatography, gas chromatography-mass spectrography, liquid chromatograph mass spectrography to the monitoring method of DBP at present.These analytical procedures all need be separated pollutent to be measured from sample, the pre-treatment process that contains the DBP sample mainly contains Suo Shi extraction, ultrasonic extraction, liquid-liquid extraction, SPE, silica gel or charcoal absorption etc.But; In these pre-treating processs, the effect between target compound and the sorbent material is nonspecific, when obtaining DBP, also can bring other impurity into; These impurity not only can the pollution detection device; Also possible interferometric analysis result, therefore, it is imperative to develop the sorbing material with specific adsorption function.
Molecularly imprinted polymer (molecularly imprinted polymer; MIP) can be used as a species specific sorbing material; It is meant with the target molecule to be template molecule (microsphere); The functionalized polymer monomer that will have a complementary structure combines with template molecule through mode covalently or non-covalently, adds linking agent and carries out polyreaction, the cross-linked high polymer that formation a kind of has the big or small and shape in fixed cavitation and have definite arranging functional to roll into a ball after after react template molecule being extracted.Because MIP has advantages such as unique chemical variety, predetermined selectivity, thermostability and long service life; It is used for SPE as sorbent material; Can be widely used in the pre-treatment process of samples such as environment, biology, medicine and food, specificity is strong, the recovery is high.
Summary of the invention
The technical problem that the present invention will solve:
When detecting in order to overcome Witcizer 300 in the prior art in the sample pretreatment process sorbent material specificity do not introduce the problem of Interference Detection impurity by force, easily; The invention provides a kind of Witcizer 300 molecularly imprinted polymer and preparation method thereof; This compound can be used in preparation Witcizer 300 molecular imprinted solid phase extraction cartridge; Make its can be simply fast, highly selective separates and enrichment the Witcizer 300 that contains in the complex matrices sample, is used for the detection of trace Witcizer 300.
Witcizer 300 molecularly imprinted polymer of the present invention prepares through following step:
(1) with template molecule Witcizer 300 (DBP), function monomer methylacrylic acid (MAA) and linking agent ethylene glycol dimethacrylate (EDMA), be dissolved in pore-creating agent chloroform or the acetonitrile, add initiator Diisopropyl azodicarboxylate (AIBN), according to mol ratio,
Template molecule: function monomer: linking agent: pore-creating agent: initiator=1: 1~10: 10~100: 10~100: 0.05~0.5; Preferable range is a template molecule: function monomer: linking agent: pore-creating agent: initiator=1: 2~8: 10~30: 20~80: 0.05~0.2, preferred ratio is 1: 4: 20: 40: 0.1.
Ultrasonic preact 0.5h in ice-water bath (UW makes various reactant thorough mixing even, and ice-water bath prevents that various reactants are heated polymerization takes place in advance that this step is a routine operation method in the laboratory in ultrasonic procedure);
(2) feed nitrogen 5~15min, use plug sealing back in 55~75 ℃ of oil baths, to react 12~48h and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution that contains 5~10% acetate to be extraction agent, soxhlet extraction 24~48h removes template molecule, re-uses methanol wash and removes residual formic acid for several times;
(4) molecularly imprinted polymer that will remove template molecule obtains Witcizer 300 molecularly imprinted polymer (DBP-MIP) in 60~70 ℃ of vacuum-drying 12~24h.
Application method technical scheme of the present invention is:
The first step, the preparation of Witcizer 300 molecular imprinted solid phase extraction cartridge
Weighing 20~300mg Witcizer 300 molecularly imprinted polymer (DBP-MIP); Use methyl alcohol homogenate; Vacuumize condition (0.01~-0.08MPa) add down 1~5mL Vestolen PP 7052 post; And the Vilaterm sieve plate is installed at the polymer packing two ends, obtain the Witcizer 300 molecular imprinted solid phase extraction cartridge.
In second step, use 1~5mL methyl alcohol or water activation solid-phase extraction column, last appearance: the extracting solution of water sample to be measured or testing sample is at the uniform velocity passed through solid phase extraction column with the speed of 0.5~5mL/min, finish back 1~2mL methanol-eluted fractions.
In the 3rd step, elutriant uses high performance liquid chromatograph or gas chromatograph-mass spectrometer test.
The performance liquid chromatography testing conditions is: UV-detector, reversed-phase column is (like C 18Chromatographic column), methanol or acetonitrile/water, degree of grade or gradient elution detect.
The gas chromatography-mass spectrography testing conditions is: the electron impact ionization source, and low-pole column (like the HP-5MS chromatographic column), constant temperature or temperature programming detect.
The essential distinction of the present invention and prior art is, has invented a kind of Witcizer 300 molecularly imprinted polymer, and the solid phase extraction column of using this polymkeric substance can adsorb the target compound in the complex sample and not introduce other impurity by highly selective.Therefore, can be widely used for aspects such as stratographic analysis, SPE, electrochemica biological sensor.
Description of drawings
Fig. 1 is a Witcizer 300 molecularly imprinted polymer schematic diagram;
Fig. 2 is the Witcizer 300 molecularly imprinted polymer infrared spectrum that obtains among the embodiment 1;
Fig. 3 is the structural representation of Witcizer 300 molecular imprinted solid phase extraction cartridge, wherein 1, and 3-sieve plate, 2-DBP-MIP; 4-Vestolen PP 7052 pillar.
Fig. 4 is a Witcizer 300 standard solution high-efficient liquid phase chromatogram;
Fig. 5 is a Witcizer 300 standard solution SPE elutriant high-efficient liquid phase chromatogram among the embodiment 1.
Embodiment
Embodiment 1
(1) the Witcizer 300 molecularly imprinted polymer is synthetic
(1) with DBP 0.5mmol, MMA 2mmol, EDMA 10mmol; AIBN0.05mmol; Be dissolved in the 20mmol acetonitrile, mixed solution is as in the round-bottomed flask, and (UW makes various reactant thorough mixing even to ultrasonic preact 0.5h in ice-water bath; Ice-water bath prevents that various reactants are heated polymerization takes place in advance that this step is a routine operation method in the laboratory in ultrasonic procedure);
(2) feed nitrogen 10min, use plug to seal back reaction 24h in 60 ℃ of oil baths and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution 200mL that contains 10% acetate to be extraction agent, soxhlet extraction 24h removes template molecule, adds extraction agent once during middle about 12h, and extraction finishes the back and uses methyl alcohol 100mL to wash to remove residual formic acid;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 60 ℃ of vacuum-drying 12h.
The Witcizer 300 molecularly imprinted polymer infrared spectrum that obtains among this embodiment is seen accompanying drawing 2.
(2) preparation of Witcizer 300 molecular imprinted solid phase extraction cartridge
Weighing 30mg Witcizer 300 molecularly imprinted polymer (DBP-MIP); Use methyl alcohol homogenate; Vacuumize condition (0.01~-0.08MPa) add down 2mL Vestolen PP 7052 post; And the Vilaterm sieve plate is installed at the polymer packing two ends, and obtaining the DBP-MIP solid-phase extraction column, its structural representation is shown in accompanying drawing 3.
(3) application method technical scheme of the present invention
(1) use 1mL methyl alcohol activation solid-phase extraction column, last appearance (extracting solution of water sample to be measured or testing sample is at the uniform velocity passed through solid phase extraction column with the speed of 1mL/min) is finished back 1mL methanol-eluted fractions.
(2) elutriant uses the high performance liquid chromatograph test.
Witcizer 300 standard substance high-efficient liquid phase chromatogram is seen accompanying drawing 4 among this embodiment, and the high-efficient liquid phase chromatogram that elutriant obtains is seen accompanying drawing 5.The color atlas of Fig. 4 and Fig. 5 is consistent, proves that solid phase extraction column can adsorb the target compound in the complex sample and not introduce other impurity by highly selective.
Embodiment 2
(1) the Witcizer 300 molecularly imprinted polymer is synthetic
(1) with DBP 0.5mmol, MMA 2mmol, EDMA 10mmol, AIBN0.05mmol is dissolved in the 20mmol chloroform, and mixed solution is as in the round-bottomed flask, ultrasonic preact 0.5h in ice-water bath;
(2) feed nitrogen 10min, use plug to seal back reaction 24h in 60 ℃ of oil baths and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution 200mL that contains 10% acetate to be extraction agent, soxhlet extraction 24h removes template molecule, adds extraction agent once during middle about 12h, and extraction finishes the back and uses methyl alcohol 100mL to wash to remove residual formic acid;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 60 ℃ of vacuum-drying 24h.
(2) preparation of Witcizer 300 molecular imprinted solid phase extraction cartridge
Weighing 30mg Witcizer 300 molecularly imprinted polymer (DBP-MIP); Use methyl alcohol homogenate; Vacuumize condition (0.01~-0.08MPa) add down 2mL Vestolen PP 7052 post; And the Vilaterm sieve plate is installed at the polymer packing two ends, and obtaining the DBP-MIP solid-phase extraction column, its structural representation is shown in accompanying drawing 3.
(3) application method technical scheme of the present invention
(1) use 1mL methyl alcohol activation solid-phase extraction column, last appearance (extracting solution of water sample to be measured or testing sample is at the uniform velocity passed through solid phase extraction column with the speed of 1mL/min) is finished back 1mL methanol-eluted fractions
(2) elutriant uses the high performance liquid chromatograph test.
Embodiment 3
(1) the Witcizer 300 molecularly imprinted polymer is synthetic
(1) with DBP 0.5mmol, MMA 2mmol, EDMA 10mmol, AIBN0.05mmol is dissolved in the 20mmol acetonitrile, and mixed solution is as in the round-bottomed flask, ultrasonic preact 0.5h in ice-water bath;
(2) feed nitrogen 10min, use plug to seal back reaction 48h in 70 ℃ of oil baths and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution 200mL that contains 5% acetate to be extraction agent, soxhlet extraction 48h removes template molecule, adds extraction agent once during the about 12h in every interval, and extraction finishes the back and uses methyl alcohol 100mL washing to remove residual formic acid;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 70 ℃ of vacuum-drying 12h.
(2) preparation of Witcizer 300 molecular imprinted solid phase extraction cartridge
Weighing 100mg Witcizer 300 molecularly imprinted polymer (DBP-MIP); Use methyl alcohol homogenate; Vacuumize condition (0.01~-0.08MPa) add down 5mL Vestolen PP 7052 post; And the Vilaterm sieve plate is installed at the polymer packing two ends, and obtaining the DBP-MIP solid-phase extraction column, its structural representation is shown in accompanying drawing 3.
(3) application method technical scheme of the present invention
(1) use 2mL methyl alcohol activation solid-phase extraction column, last appearance (extracting solution of water sample to be measured or testing sample is at the uniform velocity passed through solid phase extraction column with the speed of 1mL/min) is finished back 2mL methanol-eluted fractions.
(2) elutriant uses the high performance liquid chromatograph test.
Embodiment 4
(1) the Witcizer 300 molecularly imprinted polymer is synthetic
(1) with DBP 0.5mmol, MMA 4mmol, EDMA 20mmol, AIBN0.1mmol is dissolved in the 40mmol acetonitrile, and mixed solution is as in the round-bottomed flask, ultrasonic preact 0.5h in ice-water bath;
(2) feed nitrogen 15min, use plug to seal back reaction 24h in 60 ℃ of oil baths and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution 200mL that contains 10% acetate to be extraction agent, soxhlet extraction 24h removes template molecule, adds extraction agent once during middle about 12h, and extraction finishes the back and uses methyl alcohol 100mL to wash to remove residual formic acid;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 60 ℃ of vacuum-drying 12h.
(2) preparation of Witcizer 300 molecular imprinted solid phase extraction cartridge
Weighing 200mg Witcizer 300 molecularly imprinted polymer (DBP-MIP); Use methyl alcohol homogenate; Vacuumize condition (0.01~-0.08MPa) add down 5mL Vestolen PP 7052 post; And the Vilaterm sieve plate is installed at the polymer packing two ends, and obtaining the DBP-MIP solid-phase extraction column, its structural representation is shown in accompanying drawing 3.
(3) application method technical scheme of the present invention
(1) use 2mL methyl alcohol activation solid-phase extraction column, last appearance (extracting solution of water sample to be measured or testing sample is at the uniform velocity passed through solid phase extraction column with the speed of 1mL/min) is finished back 2mL methanol-eluted fractions.
(2) elutriant uses the high performance liquid chromatograph test.
Embodiment 5
(1) the Witcizer 300 molecularly imprinted polymer is synthetic
(1) with DBP 0.5mmol, MMA 5mmol, EDMA 50mmol, AIBN 0.25mmol is dissolved in the 50mmol acetonitrile, and mixed solution is as in the round-bottomed flask, ultrasonic preact 0.5h in ice-water bath;
(2) feed nitrogen 15min, use plug to seal back reaction 24h in 60 ℃ of oil baths and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution 200mL that contains 10% acetate to be extraction agent, soxhlet extraction 24h removes template molecule, adds extraction agent once during middle about 12h, and extraction finishes the back and uses methyl alcohol 100mL to wash to remove residual formic acid;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 60 ℃ of vacuum-drying 24h.
(2) preparation of Witcizer 300 molecular imprinted solid phase extraction cartridge
Weighing 300mg Witcizer 300 molecularly imprinted polymer (DBP-MIP); Use methyl alcohol homogenate; Vacuumize condition (0.01~-0.08MPa) add down 5mL Vestolen PP 7052 post; And the Vilaterm sieve plate is installed at the polymer packing two ends, and obtaining the DBP-MIP solid-phase extraction column, its structural representation is shown in accompanying drawing 3.
(3) application method technical scheme of the present invention
(1) use 2mL methyl alcohol activation solid-phase extraction column, last appearance (extracting solution of water sample to be measured or testing sample is at the uniform velocity passed through solid phase extraction column with the speed of 1mL/min) is finished back 2mL methanol-eluted fractions.
(2) elutriant uses the high performance liquid chromatograph test.

Claims (6)

1. Witcizer 300 molecularly imprinted polymer is characterized in that through following method preparation:
(1) with template molecule Witcizer 300, function monomer methylacrylic acid and linking agent ethylene glycol dimethacrylate; Be dissolved in pore-creating agent chloroform or the acetonitrile; Add the initiator Diisopropyl azodicarboxylate; According to mol ratio, template molecule: function monomer: linking agent: pore-creating agent: initiator=1: 1~10: 10~100: 10~100: 0.05~0.5, ultrasonic preact 0.5h in ice-water bath;
(2) feed nitrogen 5~15min, use plug sealing back in 55~75 ℃ of oil baths, to react 12~48h and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution that contains 5~10% acetate to be extraction agent, soxhlet extraction 24~48h removes template molecule, re-uses methanol wash and removes residual formic acid for several times;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 60~70 ℃ of vacuum-drying 12~24h.
2. Witcizer 300 molecularly imprinted polymer according to claim 1, wherein template molecule in the step (2): function monomer: linking agent: pore-creating agent: initiator=1: 2~8: 10~30: 20~80: 0.05~0.2.
3. Witcizer 300 molecularly imprinted polymer according to claim 2, wherein template molecule in the step (2): function monomer: linking agent: pore-creating agent: initiator=preferred ratio is 1: 4: 20: 40: 0.1.
4. the preparation method of a Witcizer 300 molecularly imprinted polymer is characterized in that, may further comprise the steps:
(1) with template molecule Witcizer 300, function monomer methylacrylic acid and linking agent ethylene glycol dimethacrylate, be dissolved in pore-creating agent chloroform or the acetonitrile, add the initiator Diisopropyl azodicarboxylate, according to mol ratio, template molecule; Function monomer: linking agent: pore-creating agent: initiator=1: 1~10: 10~100: 10~100: 0.05~0.5, ultrasonic preact 0.5h in ice-water bath;
(2) feed nitrogen 5~15min, use plug sealing back in 55~75 ℃ of oil baths, to react 12~48h and obtain reaction product.After reaction finishes, polymkeric substance is ground, sieve, use the acetone rinsing to remove fine particle, obtain the polymkeric substance of particle diameter 20~200 μ m;
(3) use the methanol solution that contains 5~10% acetate to be extraction agent, soxhlet extraction 24~48h removes template molecule, re-uses methanol wash and removes residual formic acid for several times;
(4) molecularly imprinted polymer that will remove template molecule obtains the Witcizer 300 molecularly imprinted polymer in 60~70 ℃ of vacuum-drying 12~24h.
5. the preparation method of Witcizer 300 molecularly imprinted polymer according to claim 4, wherein template molecule in the step (2): function monomer: linking agent: pore-creating agent: initiator=1: 2~8: 10~30: 20~80: 0.05~0.2.
6. the preparation method of Witcizer 300 molecularly imprinted polymer according to claim 5, wherein template molecule in the step (2): function monomer: linking agent: pore-creating agent: initiator=preferred ratio is 1: 4: 20: 40: 0.1.
CN2010102648059A 2010-08-27 2010-08-27 Dibutyl phthalate molecularly imprinted polymer (DBP-MIP) and preparation method thereof Pending CN102372821A (en)

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CN109540867A (en) * 2018-11-30 2019-03-29 东南大学 A kind of plasticiser Raman spectra detection process based on molecular engram nano fibrous membrane
CN109553798A (en) * 2018-11-28 2019-04-02 南通市产品质量监督检验所 A kind of preparation method of diisononyl phthalate molecular engram microsphere

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CN105218746B (en) * 2014-06-13 2017-06-30 中国石油化工股份有限公司 A kind of molecularly imprinted polymer and its preparation method and application
CN105218746A (en) * 2014-06-13 2016-01-06 中国石油化工股份有限公司 A kind of molecularly imprinted polymer and its preparation method and application
CN104231172A (en) * 2014-09-24 2014-12-24 刘秀珠 Preparation method of DIHP (Dihexylphthalate) molecularly imprinted solid phase extraction column filling material
CN105622824A (en) * 2014-11-07 2016-06-01 中国石油化工股份有限公司 Molecularly imprinted polymer, preparation method and applications thereof
CN105622824B (en) * 2014-11-07 2019-03-26 中国石油化工股份有限公司 A kind of molecularly imprinted polymer and its preparation method and application
CN104497183A (en) * 2015-01-20 2015-04-08 河南工业大学 Method for preparing phthalate imprinted polymer by atom transfer radical polymerization method
CN105085765A (en) * 2015-06-24 2015-11-25 浙江农林大学 Preparation method for dimethyl phthalate molecularly imprinted microspheres
CN106380619A (en) * 2016-08-24 2017-02-08 江苏大学 Preparation method and application of fluorescent molecularly imprinted adsorption separation material
CN107400187A (en) * 2017-07-04 2017-11-28 新疆农垦科学院 A kind of preparation method and application of phthalate molecular imprinted polymer on surface
CN107400187B (en) * 2017-07-04 2019-04-26 新疆农垦科学院 A kind of preparation method and application of phthalate molecular imprinted polymer on surface
CN109553798A (en) * 2018-11-28 2019-04-02 南通市产品质量监督检验所 A kind of preparation method of diisononyl phthalate molecular engram microsphere
CN109540867A (en) * 2018-11-30 2019-03-29 东南大学 A kind of plasticiser Raman spectra detection process based on molecular engram nano fibrous membrane
CN109540867B (en) * 2018-11-30 2021-07-27 东南大学 Plasticizer Raman spectrum detection method based on molecularly imprinted nanofiber membrane

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