CN108912312A - A kind of preparation and its application of hydrophobic porous organic polymer material - Google Patents
A kind of preparation and its application of hydrophobic porous organic polymer material Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/025—Polyxylylenes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/02—Food
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/22—Molecular weight
- C08G2261/228—Polymers, i.e. more than 10 repeat units
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
- C08G2261/3326—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms alkane-based
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/35—Macromonomers, i.e. comprising more than 10 repeat units
- C08G2261/352—Macromonomers, i.e. comprising more than 10 repeat units containing only carbon atoms
Abstract
The present invention relates to the detection fields of polycyclic aromatic hydrocarbon in food.The present invention discloses a kind of hydrophobic porous organic polymeric solid phase fiber material and its application in the analysis of food persistent pollutant polycyclic aromatic hydrocarbon.The material is rich in hydrophobicity phenyl ring functional group, is rich in mesoporous and microcellular structure, large specific surface area improves the bioaccumulation efficiency of polycyclic aromatic hydrocarbon analysis detection sample pre-treatments in food, and reduces the matrix interference of target analyte detection.With traditional solid phase extraction material ratio, this material physical and chemical stability is good, and functional group is embedded in material skeleton, and content is high and stabilization not easily runs off, and the materials'use service life is long, reusable.
Description
Technical field
The present invention relates to the detection field of polycyclic aromatic hydrocarbon in food, specifically a kind of hydrophobic porous organic polymer
Adsorbent material and its detection for persistent pollutant polycyclic aromatic hydrocarbon in food.
Background technique
Common pretreatment technology mainly has Soxhlet extraction, accelerates in polycyclic aromatic hydrocarbon analyte detection process in aquatic products at present
Solvent extraction, microwave auxiliary extraction, liquid-liquid distribution, column chromatography (Florisil silica gel, diatomite and alumina column chromatography)
And the technologies such as Solid Phase Extraction.Wherein solvent extraction, being subject to column chromatography purification technology is most common method in national standard.Singh
Use dichloromethane-acetone ultrasonic extraction Deng (2014), later using Soxhlet extraction, cross the pre-treating method of silicagel column, can be with
16 kinds of polycyclic aromatic hydrocarbons in tealeaves are detected, but the method is more complicated, time-consuming.Although these technologies do not need expensive equipment and spy
Different instrument, but in entire analytic process it is time-consuming and laborious, easily cause sample loss, cause the rate of recovery to reduce, and need to consume big
The organic solvent of amount also results in the pollution to environment.Solid phase extraction techniques overcome liquid-liquid extraction techniques and general column chromatography
The shortcomings that, effectively component to be measured can be separated with interfering component, extraction process is simple and quick, and solvent consumption is few, reproducibility
The good and rate of recovery is high, and reduces the introducing of impurity, it is easy to accomplish automation, thus there is development well in PAHs analysis
Prospect.Core of the Solid Phase Extraction matrix as the technology, can be mainly divided into polymer material, silica gel material from material category
With polymer-silica gel hybridization material three categories.Wherein polymer material specific surface area is smaller, generally less than 50m2/g(Svec,
F.,Fréchet,J.M.J.Anal.Chem.,1992,64(7):820-822；)；And silica gel material and polymer-silica gel hybridization
Material specific surface area is then relatively larger, but also there was only 200~300m2Between/g (N.Tanaka, H.Kobayashi,
K.Nakanishi,H.Minakuchi,N.Ishizuka,Anal.Chem.2001,73,420；G.,Ronald,H.Peter,
F.Alwin,R.Regina,S.Helmut,T.Andreas,Chem.-Eur.J.2014,20,17579).Current adsorbent material
For the enrichment of PAHs in food, the ultimate challenge faced is mainly derived from the limit of material specific surface area and functional group content
System, causes bioaccumulation efficiency limited, detection sensitivity needs to be further increased.Therefore, functional group content height, specific surface area are developed
Big solid phase extraction material is to realize the high sensitivity of polycyclic aromatic hydrocarbon in food, high-throughput point for the sample pretreatment of PAHs
Analyse the key technology of urgent need to resolve.
Porous organic polymer material (porous organic polymers, POPs) be it is a kind of by light element (C, H, O,
N, B etc.) it is connected with each other, by covalent bond rich in mesoporous and micropore novel porous materials.Its, porosity low with skeletal density
The advantages of height, large specific surface area, and it is with good stability under the harsh conditions such as soda acid, solvent, moisture and high temperature.This
Outside, the organic monomer type for synthesizing POPs is abundant, can by select different functional groups reaction monomers and different synthesizing means
Regulate and control microcellular structure, size and its functionalization, selects the organic monomer of different structure or functional group that can design synthesis different
The POPs rich medium of structure and type, for the Sample Pretreatment Technique in food analysis.Therefore, benzene rich in is synthesized
The POPs material of ring structure and high-specific surface area can be used for polycyclic in food by the way that stronger π-is pi-conjugated and hydrophobic interaction
The high capacity of aromatic hydrocarbons and highly selective Solid Phase Extraction.
Summary of the invention
The technical problem to be solved by the present invention is to be directed to the current aquatic products PAHs trace analysis sample pre-treatments rate of recovery not
Height, the low problem of sensitivity, the present invention is intended to provide a kind of hydrophobic porous organic polymer material, hydrophobicity rich in
Phenyl structure；The second object of the present invention is to providing a kind of porous organic polymer material producing method simple to operation；Mesh of the present invention
Third is that fast enriching of the hydrophobic porous organic polymer material for Determination of Trace Polycyclic Aromatic Hydrocarbons in aquatic products system, is realized multiple
The high sensitivity of Determination of Trace Polycyclic Aromatic Hydrocarbons, high throughput analysis in miscellaneous food system.
Used technical solution is the present invention to solve above-mentioned technical problem：A kind of hydrophobic porous organic polymer suction
Enclosure material, which is characterized in that hydrophobicity phenyl structure rich in the porous organic polymer adsorbent material, such as followingization
Formula：
M=50-300 in formula；N=50-300.
The preparation method of hydrophobic porous organic polymer material of the present invention, is prepared as follows：
Monomer and dimethoxymethane containing aromatic group are added in round-bottomed flask, lewis acid is added as polymerization
The catalyst of reaction is added 1,2- dichloroethanes as solvent, under conditions of being vigorously stirred, is heated to 30-120 DEG C, preferably
It is 80 DEG C, makes the compound homogeneous polymerization containing aromatic group, polymerization time 12-48h, preferably for 24 hours；Obtained solid is used
Methanol is that solvent carries out Soxhlet extraction, extracts 12-72h, preferably for 24 hours；Filtering, the porous organic polymer obtained by drying are inhaled
Enclosure material.
According to the present invention, the aromatic-containing compound be selected from toluene, 1,3,5- triphenyl methane, one of biphenyl or
It is two or more.
According to the present invention, the lewis acid catalyst is in alchlor, ferric trichloride or boron trifluoride
It is a kind of.
According to the present invention, the solvent in methylene chloride, chloroform, methylene chloride, dichloroethanes or chlorobenzene one
Kind is two or more.
According to the present invention, the amount of the lewis acid catalyst of the addition is the 0.1-10 of porous organic polymer quality
Times.
Application of the porous organic polymer material of the present invention in food in polycyclic aromatic hydrocarbon Solid Phase Extraction.Described consolidates
Mutually extraction can be directly used granular material and carry out offline sample pretreatment, can also be prepared into chromatographic column form and realize online
Solid Phase Extraction.
It is described to be applied in polycyclic aromatic hydrocarbon Solid Phase Extraction in food according to the present invention, second in extractant acetonitrile solution
Nitrile volume fraction be 0-50%, preferably 10%, eluting solvent be selected from one or both of acetone, methanol, acetonitrile, n-hexane
More than；The porous organic polymer adsorbent material dosage is 5-500mg, preferably 10-100mg.
The present invention has the advantages that significant compared with similar porous organic polymer material：
Phenyl ring hydrophobic functional groups, gained material are uniform-distribution in the hydrophobic porous organic polymer material structure of the present invention
Expect large specific surface area, and there is abundant mesoporous and microcellular structure, functional group content is high in material skeleton and stablizes.
The present invention is based on large specific surface area, rich in the hydrophobic porous organic poly- of π-π interaction phenyl ring functional group
Object is closed, the Solid Phase Extraction with very big potentiality for persistent pollutant polycyclic aromatic hydrocarbon in food increases sample pretreatment and returns
Yield improves its detection sensitivity.Be conducive to improve the enrichment capacity of sample pretreatment.
The hydrophobic porous organic polymer material physical and chemical stability of the present invention is good, and phenyl ring functional group is embedded in material skeleton
In, content is high and stabilization not easily runs off, and the materials'use service life is long, reusable.As solid phase extraction material, for eating
The fast enriching of Determination of Trace Polycyclic Aromatic Hydrocarbons in product complex sample system, to realize the high sensitivity of Determination of Trace Polycyclic Aromatic Hydrocarbons, height in food
Flux distribution.
Detailed description of the invention
Fig. 1 is that (phenyl is porous organic for the hydrophobic porous organic polymer material A nitrogen physisorption analysis of spectra of the present invention
The adsorption isotherm of polymer material).
Fig. 2 is that (phenyl is porous organic for the hydrophobic porous organic polymer material A nitrogen physisorption analysis of spectra of the present invention
The graph of pore diameter distribution of polymer material).
Fig. 3 is the trapping chromatography figure that the hydrophobic porous organic polymer material of the present invention is used for 15 kinds of polycyclic aromatic hydrocarbons.
Fig. 4 is the contact angle test figure of hydrophobic porous material of the present invention.
Specific embodiment：
Method provided by the invention is described in detail below with reference to embodiment, but the invention is not limited in any way.
The preparation of 1 materials A of embodiment
In 25mL round bottom single-necked flask, 1.84g toluene is added, 6.5g FeCl is added in 3.04g dimethoxymethane3Make
For the catalyst of polymerization reaction, 20mL1 is added, 2- dichloroethanes is as solvent, under conditions of being vigorously stirred, is heated to 80
DEG C, make toluene and dimethoxymethane homogeneous polymerization, polymerization time is for 24 hours.It with methanol is that solvent carries out rope by obtained solid
Family name extracts, filtering, in 80 DEG C of hydrophobic porous organic polymer material A obtained by drying.
The preparation of 2 material B of embodiment
In 25mL round bottom single-necked flask, 1,3,5- triphenylbenzene of 2.40g is added, 3.04g dimethoxymethane is added
6.5g FeCl3As the catalyst of polymerization reaction, 20mL1 is added, 2- dichloroethanes is as solvent, in the condition being vigorously stirred
Under, 80 DEG C are heated to, 1,3,5- triphenylbenzenes and dimethoxymethane homogeneous polymerization are made, polymerization time is for 24 hours.Consolidate what is obtained
Body is that solvent carries out Soxhlet extraction with methanol, filtering, in 80 DEG C of hydrophobic porous organic polymer material B obtained by drying.
The preparation of 3 material C of embodiment
In 25mL round bottom single-necked flask, 1,3,5- triphenylbenzene of 1.20g and 0.92g toluene, 3.04g dimethoxy is added
6.5g FeCl is added in methylmethane3As the catalyst of polymerization reaction, 20mL1 is added, 2- dichloroethanes is as solvent, violent
Under conditions of stirring, 80 DEG C are heated to, makes 1,3,5- triphenylbenzenes, toluene and dimethoxymethane homogeneous polymerization, polymerization time
For for 24 hours.It with methanol is that solvent carries out Soxhlet extraction by obtained solid, filtering is obtained by drying described hydrophobic porous in 80 DEG C
Organic polymer material C.
The preparation of 4 material D of embodiment
In 25mL round bottom single-necked flask, 3.08g biphenyl is added, 6.5g FeCl is added in 3.04g dimethoxymethane3Make
For the catalyst of polymerization reaction, 20mL1 is added, 2- dichloroethanes is as solvent, under conditions of being vigorously stirred, is heated to 80
DEG C, make biphenyl and dimethoxymethane homogeneous polymerization, polymerization time is for 24 hours.It with methanol is that solvent carries out rope by obtained solid
Family name extracts, filtering, in 80 DEG C of hydrophobic porous organic polymer material D obtained by drying.
The preparation of 5 material E of embodiment
In 25mL round bottom single-necked flask, 1.56g benzene is added, 6.5g FeCl is added in 3.04g dimethoxymethane3As
20mL1 is added in the catalyst of polymerization reaction, and 2- dichloroethanes is as solvent, under conditions of being vigorously stirred, is heated to 80 DEG C,
Make benzene and dimethoxymethane homogeneous polymerization, polymerization time is for 24 hours.It with methanol is that solvent carries out Soxhlet and mentions by obtained solid
It takes, filters, in 80 DEG C of hydrophobic porous organic polymer material E obtained by drying.
Embodiment 6：
By the hydrophobic porous organic polymer adsorbent material 50mg of the various embodiments described above preparation, it is with acetonitrile volume fraction
10% acetonitrile solution is as extractant, using acetone as eluting solvent, based on π-π interaction and hydrophobic interaction
Mechanism is used for the Solid Phase Extraction of 15 kinds of polycyclic aromatic hydrocarbons, as shown in figure 3, its target compound is captured well.
From attached drawing 1 and Fig. 2 as it can be seen that the material has abundant mesoporous and microcellular structure, average pore size 3.2nm, Kong Rong
Amount is 0.61cm3/ g, specific surface area are up to 785m2/ g, wherein specific surface area provided by micropore is 521m2/ g, it is mesoporous to be provided
Specific surface area be 264m2/ g, resulting materials Zhang Fuhan hydrophobicity phenyl ring functional group are very beneficial for improving sample pretreatment
Enrichment capacity and selectivity.
It is illustrated in fig. 4 shown below, the water contact angle of prepared hydrophobic material is up to 160 degree, it was demonstrated that material hydrophobic is good, has
It is enriched with conducive to the reverse phase of polycyclic aromatic hydrocarbon compounds.
Claims (10)
1. a kind of hydrophobic porous organic polymer adsorbent material, which is characterized in that the porous organic polymer adsorbent material bone
Hydrophobic phenyl ring functional group, such as following chemical formula are rich in frame：
M=50-300 in formula；N=50-300.
2. the preparation method of hydrophobic porous organic polymer adsorbent material according to claim 1, it is characterised in that：According to such as
The preparation of lower section method：
Monomer and dimethoxymethane containing aromatic group are added in round-bottomed flask, lewis acid is added as polymerization reaction
Catalyst, be added 1,2- dichloroethanes as solvent, under conditions of being vigorously stirred, be heated to 30-120 DEG C, preferably 80
DEG C, make the compound homogeneous polymerization containing aromatic group, polymerization time 12-48h, preferably for 24 hours；The solid methanol that will be obtained
Soxhlet extraction is carried out for solvent, extracts 12-72h, preferably for 24 hours；Filtering, the porous organic polymer adsorption material obtained by drying
Material.
3. the preparation method of porous organic polymer adsorbent material according to claim 1, it is characterised in that：Described contains fragrance
Compound monomer is selected from toluene, 1,3,5- triphenyl methane, one or more of biphenyl.
4. the preparation method of porous organic polymer adsorbent material according to claim 1, it is characterised in that：The Louis
Acid catalyst is selected from one of alchlor, ferric trichloride or boron trifluoride.
5. the preparation method of porous organic polymer adsorbent material according to claim 1, it is characterised in that：The dimethoxy
The molal weight ratio of methylmethane and aromatic compound monomer is 1:1 to 10:1, preferably 2:1.
6. the preparation method of porous organic polymer adsorbent material according to claim 1, it is characterised in that：The road of the addition
The amount of Lewis acid catalyst is 0.1-10 times of porous organic polymer quality.
7. the preparation method of porous organic polymer adsorbent material according to claim 1, it is characterised in that：The solvent is selected from
One or more of methylene chloride, chloroform, methylene chloride, dichloroethanes or chlorobenzene.
8. the application of porous organic polymer adsorbent material according to claim 1, it is characterised in that：It is described porous organic
Application of the polymer material in food in persistent pollutant polycyclic aromatic hydrocarbon Solid Phase Extraction.
9. the application of porous organic polymer adsorbent material according to claim 8, it is characterised in that：The solid phase extraction
It takes and directlys adopt the offline sample pretreatment of granular material progress, or be prepared into chromatographic column form and realize on-line solid phase extraction.
10. the application of porous organic polymer adsorbent material according to claim 8 or claim 9, it is characterised in that：In food
Applied in polycyclic aromatic hydrocarbon Solid Phase Extraction, in extractant acetonitrile solution acetonitrile volume fraction be 0-50%, preferably 10%, wash
Desolventizing is selected from one or more of acetone, methanol, acetonitrile, n-hexane；The porous organic polymer adsorption material
Material dosage is 5-500mg, preferably 10-100mg.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110921755A (en) * | 2019-12-06 | 2020-03-27 | 大连理工大学 | Oxygen-enriched super-crosslinked porous organic polymer material, preparation method and application |
| WO2020151001A1 (en) * | 2019-01-25 | 2020-07-30 | 浙江大学 | Preparation method for super-hydrophobic high specific surface area microporous polymer adsorbent material |
| CN111617750A (en) * | 2020-04-20 | 2020-09-04 | 广东省测试分析研究所（中国广州分析测试中心） | Microporous polymer polydopamine composite solid-phase microextraction probe and preparation method and application thereof |
| CN111644160A (en) * | 2020-05-19 | 2020-09-11 | 浙江大学 | Green preparation method of super-hydrophobic microporous polymer adsorption material |
| CN111892737A (en) * | 2020-05-29 | 2020-11-06 | 浙江省舟山海洋生态环境监测站 | Method for detecting polycyclic aromatic hydrocarbons in sea area sediments |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020151001A1 (en) * | 2019-01-25 | 2020-07-30 | 浙江大学 | Preparation method for super-hydrophobic high specific surface area microporous polymer adsorbent material |
| CN110921755A (en) * | 2019-12-06 | 2020-03-27 | 大连理工大学 | Oxygen-enriched super-crosslinked porous organic polymer material, preparation method and application |
| CN111617750A (en) * | 2020-04-20 | 2020-09-04 | 广东省测试分析研究所（中国广州分析测试中心） | Microporous polymer polydopamine composite solid-phase microextraction probe and preparation method and application thereof |
| CN111644160A (en) * | 2020-05-19 | 2020-09-11 | 浙江大学 | Green preparation method of super-hydrophobic microporous polymer adsorption material |
| CN111892737A (en) * | 2020-05-29 | 2020-11-06 | 浙江省舟山海洋生态环境监测站 | Method for detecting polycyclic aromatic hydrocarbons in sea area sediments |
| CN111892737B (en) * | 2020-05-29 | 2021-04-20 | 浙江省舟山海洋生态环境监测站 | Method for detecting polycyclic aromatic hydrocarbons in sea area sediments |
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Application publication date: 20181130 |