CN114437275A - High-specific-surface-area adsorption resin and application thereof in removing dinotefuran residues - Google Patents
High-specific-surface-area adsorption resin and application thereof in removing dinotefuran residues Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
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- 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
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
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- B01J20/28057—Surface area, e.g. B.E.T specific surface area
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- C08J2335/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
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Abstract
The invention discloses a high specific surface area C8-maleic anhydride adsorption resin and application thereof in removing dinotefuran residues, wherein a suspension polymerization method is adopted to carry out Friedel-crafts cross-linking reaction after a petrochemical industry by-product C8 fraction is copolymerized with maleic anhydride, and the high specific surface area C8-maleic anhydride adsorption resin is obtained. The preparation process does not need an additional pore-forming agent, the formula and the process are simple, the resource utilization of the C8 fraction can be realized, the obtained adsorption resin has high dinotefuran adsorption capacity and thorough adsorption, and the dinotefuran pesticide residue removing material is excellent in performance.
Description
Technical Field
The invention belongs to the field of synthesis of high polymer materials, and particularly relates to an adsorption resin with a high specific surface area and application thereof in removing dinotefuran residues.
Background
Dinotefuran, as a latest generation of nicotine pesticide, is widely applied to pest control of crops such as rice, vegetables, fruits and tea by virtue of the characteristics of high efficiency, low toxicity, strong water solubility, wide insecticidal spectrum, convenient use, capability of overcoming resistance risks brought by first and second generation pesticides and the like. At present, research on dinotefuran mainly focuses on research on development, application and prevention of a synthetic route, evaluation on toxicity and safety, a method for measuring dinotefuran and the like, and research on removal of residual dinotefuran is very little. With the wider application range of dinotefuran in the agricultural process, the maximum pesticide residue limit value related to dinotefuran is formulated in each country and each region. The problem of overproof dinotefuran residue severely restricts the export of agricultural products and related extracts in China, so that how to remove the residue of dinotefuran is very important.
The C8 fraction is mainly obtained from the process of producing ethylene and propylene by pyrolysis of petroleum hydrocarbon, and is a mixture of substances having complex components, such as olefin and aromatic hydrocarbon, as shown in table 1. The compositions of the produced C8 are different due to different cracking processes and raw materials of different manufacturers, but the C8 is rich in unsaturated hydrocarbons such as styrene and aromatic hydrocarbon compounds such as toluene and the like. With the rapid development of petrochemical industries such as ethylene, the production of cracked C8 aromatic hydrocarbons is also greatly increased. At present, the C8 fraction in China is mainly used for producing styrene, paraxylene, blend gasoline and solvents, but because the composition of raw materials changes greatly, the separation efficiency of each component is low, the product quality is unstable, and a processing method which fully utilizes the value of the C8 fraction is sought, so that the method has huge economic benefit and environmental benefit.
TABLE 1 certain plant C8 fraction
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the adsorption resin with high specific surface area, which not only can realize the resource utilization of C8 fraction, but also can be used for removing the residual dinotefuran in crops, extracts thereof and other products, and the prepared adsorption resin has high dinotefuran adsorption capacity and thorough adsorption.
In order to achieve the purpose, the invention adopts a suspension polymerization method to copolymerize a petrochemical industry byproduct C8 fraction and maleic anhydride to obtain C8-maleic anhydride adsorption resin, and then the obtained resin is subjected to a Friedel-crafts crosslinking reaction to obtain the C8-maleic anhydride adsorption resin with a high specific surface area.
It will be understood by those skilled in the art that the C8 fraction is a conventional petrochemical industry by-product C8 fraction having a polymerizable unsaturated aromatic content of 20-55% (e.g., 22%, 25%, 28%, 30%, 35%, 40%, 45%, 50%, etc.) and a hard-to-polymerize saturated aromatic content of 30-70% (e.g., 32%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, etc.). Wherein, the polymerizable unsaturated aromatic hydrocarbon refers to aromatic hydrocarbon containing double bond or triple bond, including styrene, allyl benzene, vinyl toluene, indene, methyl indene, etc., and the difficultly polymerizable saturated aromatic hydrocarbon refers to aromatic hydrocarbon containing no double bond or triple bond, including benzene, toluene, ethylbenzene, etc.
The specific synthesis steps of the high specific surface area C8-maleic anhydride adsorption resin comprise the following steps:
(1) synthesis of C8-maleic anhydride adsorbent resin white balls:
dissolving a dispersing agent and inorganic salt in water to prepare a water phase;
uniformly mixing C8 fraction, maleic anhydride, a cross-linking agent and an initiator to obtain an oil phase;
adding the water phase into a reaction kettle, heating to 25-60 ℃, and then adding the oil phase, wherein the volume ratio of the water phase to the oil phase is 3-4: 1, stirring to disperse the oil phase into the water phase, heating to 40-80 ℃, reacting for 3-5h, continuously heating to 55-95 ℃, reacting for 3-5h, stopping the reaction, and cooling; and discharging the cooled resin balls, extracting with methylal with the volume 5-10 times that of the resin, washing and drying to obtain the C8-maleic anhydride adsorption resin white balls.
(2) Synthesizing high specific surface area C8-maleic anhydride adsorption resin:
uniformly mixing C8-maleic anhydride adsorption resin white balls and anhydrous aluminum chloride in dichloromethane, wherein the mass ratio of the resin white balls to the anhydrous aluminum chloride is 5-10:1, the amount of the dichloromethane is 3-15 times of the volume of the resin white balls, stirring for 10-15h at room temperature, fully swelling the resin, reacting for 10-15h at 60-80 ℃, cooling and discharging, washing with acetone and methanol respectively to remove the anhydrous aluminum chloride, performing Soxhlet extraction for 10-15h with methanol, and drying in a vacuum drying oven at 60-80 ℃ to constant weight to obtain the C8-maleic anhydride adsorption resin with high specific surface area.
In the preparation method, in the step (1), the dispersing agent is selected from one or more of gelatin, polyvinyl alcohol, poly (meth) acrylate, talcum powder and kaolin, and the inorganic salt is selected from one or more of sodium sulfate, sodium chloride, potassium chloride and potassium sulfate;
the mass concentration of the dispersant in the water phase is 0.08-0.8%, and the mass concentration of the inorganic salt is 0.4-1%;
the cross-linking agent is selected from one or more of divinylbenzene, trivinylbenzene, divinyltoluene, divinylethylbenzene, ethylene glycol dimethacrylate and allyl methacrylate, the initiator is selected from one or more of oil-soluble azo free radical initiators (such as azobisisoheptonitrile, azobisisobutyronitrile and the like), oil-soluble peroxide free radical initiators (such as dibenzoyl peroxide and the like), and oil-soluble redox initiation systems (such as laurylamine peroxide/N, N-dibutylaniline and the like);
in the oil phase, maleic anhydride accounts for 1-8% of the mass of the C8 fraction, the cross-linking agent accounts for 2-30% of the mass of the C8 fraction, the initiator accounts for 0.2-2% of the total mass of the maleic anhydride, the C8 fraction and the cross-linking agent, and no pore-forming agent is added.
The specific surface area of the resin prepared by the invention is preferably 530-1100m2/g。
The C8-maleic anhydride adsorption resin with high specific surface area can be applied to removing dinotefuran residues, and the adsorption rate of dinotefuran in a static adsorption application experiment is 50-100%.
The invention has the beneficial effects that:
by suspension polymerization, the adsorption resin is prepared by taking the petrochemical industry byproduct C8 fraction as a raw material, no pore-forming agent is added, the formula is simple, the adsorption resin with higher specific surface area and moderate pore diameter can be obtained, and the resource utilization of the C8 fraction can be realized; the addition of maleic anhydride in the formula can increase the adsorption capacity and high selectivity of the resin to dinotefuran, the post-crosslinking reaction can further increase the specific surface area of the adsorption resin, and the obtained adsorption resin has high adsorption capacity to dinotefuran and thorough adsorption, and is a dinotefuran pesticide residue removal material with excellent performance.
Detailed Description
The technical solutions of the present invention are illustrated below by examples, which, however, do not limit the present invention.
The fraction C8 used in the examples contained 28% of polymerizable unsaturated aromatic hydrocarbons and 53% of hardly polymerizable saturated aromatic hydrocarbons.
Example 1:
1. synthesis of C8-maleic anhydride adsorption resin white ball
Dissolving sodium sulfate and gelatin in water to prepare a water phase, wherein the mass concentration of the gelatin in the water phase is 0.2%, and the mass concentration of the sodium sulfate is 0.5%;
uniformly mixing a C8 fraction, maleic anhydride, ethylene glycol dimethacrylate and azobisisoheptonitrile to obtain an oil phase, wherein the mass of the maleic anhydride accounts for 2% of that of the C8 fraction, the mass of the ethylene glycol dimethacrylate accounts for 5% of that of the C8 fraction, and the mass of the azobisisoheptonitrile accounts for 0.8% of the total mass of the maleic anhydride, the C8 fraction and the ethylene glycol dimethacrylate;
adding the water phase into a reaction kettle, heating to 25 ℃, and then adding the oil phase, wherein the volume ratio of the water phase to the oil phase is 3: 1, stirring to disperse the oil phase into the water phase, heating to 45 ℃, reacting for 3 hours, continuously heating to 60 ℃, reacting for 3 hours, stopping the reaction, and cooling; and discharging the cooled resin balls, extracting with methylal with the volume 5 times that of the resin, washing and drying to obtain the C8-maleic anhydride adsorption resin white balls.
2. Synthesis of high specific surface area C8-maleic anhydride adsorption resin
Uniformly mixing C8-maleic anhydride adsorption resin white balls, dichloromethane and anhydrous aluminum chloride, wherein the mass ratio of the resin white balls to the anhydrous aluminum chloride is 5:1, the using amount of the dichloromethane is 5 times of the volume of the resin white balls, stirring for 12 hours at room temperature, fully swelling the white balls, then reacting for 15 hours at 60 ℃, cooling and discharging, respectively washing with acetone and methanol to remove the anhydrous aluminum chloride, then performing Soxhlet extraction on the resin for 12 hours by using methanol, and drying in a vacuum drying oven at 60 ℃ to constant weight to obtain the C8-maleic anhydride adsorption resin with high specific surface area.
Example 2:
1. synthesis of C8-maleic anhydride adsorption resin white ball
Dissolving sodium chloride and polyvinyl alcohol in water to prepare a water phase, wherein the mass concentration of the polyvinyl alcohol in the water phase is 0.6%, and the mass concentration of the sodium chloride is 0.8%;
uniformly mixing the C8 fraction, maleic anhydride, divinylbenzene and azobisisobutyronitrile to form an oil phase, wherein the mass of the maleic anhydride accounts for 6% of that of the C8 fraction, the mass of the divinylbenzene accounts for 25% of that of the C8 fraction, and the mass of the azobisisobutyronitrile accounts for 1.6% of the total mass of the maleic anhydride, the C8 fraction and the divinylbenzene;
adding the water phase into a reaction kettle, heating to 55 ℃, and then adding the oil phase, wherein the volume ratio of the water phase to the oil phase is 4: 1, stirring to disperse the oil phase into the water phase, heating to 80 ℃, reacting for 4 hours, continuously heating to 90 ℃, reacting for 5 hours, stopping the reaction, and cooling; and discharging the cooled resin balls, extracting with methylal with the volume 10 times that of the resin, washing, and drying to obtain the C8-maleic anhydride adsorption resin.
2. Synthesis of high specific surface area C8-maleic anhydride adsorption resin
Uniformly mixing C8-maleic anhydride adsorption resin white balls, dichloromethane and anhydrous aluminum chloride, wherein the mass ratio of the resin white balls to the anhydrous aluminum chloride is 9:1, the using amount of the dichloromethane is 12 times of the volume of the resin white balls, stirring for 15 hours at room temperature, fully swelling the white balls, then reacting for 12 hours at 70 ℃, cooling and discharging, respectively washing with acetone and methanol to remove the anhydrous aluminum chloride, then performing Soxhlet extraction on the resin for 15 hours by using methanol, and drying in a vacuum drying oven at 80 ℃ to constant weight to obtain the C8-maleic anhydride adsorption resin with high specific surface area.
Example 3:
1. synthesis of C8-maleic anhydride adsorbent resin
Dissolving potassium chloride and polyvinyl alcohol in water to prepare a water phase, wherein the mass concentration of the polyvinyl alcohol in the water phase is 0.5%, and the mass concentration of the potassium chloride is 0.8%;
uniformly mixing the C8 fraction, maleic anhydride, divinylbenzene and dibenzoyl peroxide to obtain an oil phase, wherein the maleic anhydride accounts for 2% of the mass of the C8 fraction, the divinylbenzene accounts for 25% of the mass of the C8 fraction, and the dibenzoyl peroxide accounts for 1.0% of the total mass of the maleic anhydride, the C8 fraction and the divinylbenzene;
adding the water phase into a reaction kettle, heating to 40 ℃, and then adding the oil phase, wherein the volume ratio of the water phase to the oil phase is 3: 1, stirring to disperse the oil phase into the water phase, heating to 75 ℃, reacting for 4 hours, continuously heating to 85 ℃, reacting for 4 hours, stopping the reaction, and cooling; and discharging the cooled resin balls, extracting with methylal with the volume 10 times that of the resin, washing, and drying to obtain the C8-maleic anhydride adsorption resin.
2. Synthesis of high specific surface area C8-maleic anhydride adsorption resin
Uniformly mixing C8-maleic anhydride adsorption resin white balls, dichloromethane and anhydrous aluminum chloride, wherein the mass ratio of the resin white balls to the anhydrous aluminum chloride is 8:1, the using amount of the dichloromethane is 9 times of the volume of the resin white balls, stirring for 12 hours at room temperature, fully swelling the white balls, then reacting for 10 hours at 80 ℃, cooling and discharging, respectively washing with acetone and methanol to remove the anhydrous aluminum chloride, then performing Soxhlet extraction on the resin for 12 hours by using methanol, and drying in a vacuum drying oven at 70 ℃ until the weight is constant to obtain the C8-maleic anhydride adsorption resin with the high specific surface area.
Example 4:
BET test using the high specific surface area C8-maleic anhydride adsorption resin prepared in example 1 showed a specific surface area of 546m2/g。
Preparing 200mg/L dinotefuran solution, putting 50mL into a 100mL conical flask, weighing 0.5g of the C8-maleic anhydride adsorption resin with high specific surface area prepared in example 1, adding the weighed resin into the conical flask, putting the conical flask into a 283K constant temperature oscillator, oscillating for 8 hours at an oscillation speed of 120r/min, and testing that the dinotefuran concentration in the adsorbed solution is 34mg/L and the dinotefuran adsorption rate of the C8-maleic anhydride adsorption resin with high specific surface area prepared in example 1 on dinotefuran is 83%.
Example 5:
BET test using the high specific surface area C8-maleic anhydride adsorption resin prepared in example 2 showed a specific surface area of 795m2/g。
Preparing 180mg/L dinotefuran solution, putting 50mL into a 100mL conical flask, weighing 0.8g of the C8-maleic anhydride adsorption resin with the high specific surface area prepared in the example 2, adding the weighed resin into the conical flask, putting the conical flask into a 283K constant temperature oscillator, oscillating for 8 hours at an oscillation speed of 120r/min, testing that the dinotefuran concentration in the adsorbed solution is 18mg/L, and the dinotefuran adsorption rate of the C8-maleic anhydride adsorption resin with the high specific surface area prepared in the example 2 on dinotefuran is 90%.
Example 6:
BET test using the high specific surface area C8-maleic anhydride adsorption resin prepared in example 3, the specific surface area was 1026m2/g。
Preparing 150mg/L dinotefuran solution, putting 50mL into a 100mL conical flask, weighing 1.0g of the C8-maleic anhydride adsorption resin with high specific surface area prepared in example 3, adding the weighed material into the conical flask, putting the conical flask into a 283K constant temperature oscillator, oscillating for 8 hours at an oscillation speed of 120r/min, testing that the dinotefuran concentration in the adsorbed solution is 2mg/L, and the dinotefuran adsorption rate of the C8-maleic anhydride adsorption resin with high specific surface area prepared in example 3 on dinotefuran is 99%.
Comparative example 1
An adsorption resin was prepared in the same manner as in example 2 except that: in the oil phase, maleic anhydride accounted for 12% by mass of the C8 fraction.
The C8-maleic anhydride adsorption resin prepared in comparative example 1 was used for BET test and had a specific surface area of 505m2The dinotefuran adsorption rate was measured by the same method as in example 5 and was 63%/g.
Claims (10)
1. A preparation method of a high specific surface area adsorption resin comprises the following steps:
(1) synthesis of C8-maleic anhydride adsorption resin white ball
Dissolving a dispersing agent and inorganic salt in water to prepare a water phase;
uniformly mixing C8 fraction, maleic anhydride, a cross-linking agent and an initiator to obtain an oil phase;
adding the water phase into a reaction kettle, heating, then adding the oil phase, heating for reaction, stopping the reaction, and cooling; discharging the cooled resin balls, extracting with methylal, washing and drying to obtain C8-maleic anhydride adsorption resin white balls;
(2) synthesis of high specific surface area C8-maleic anhydride adsorption resin
Uniformly mixing C8-maleic anhydride adsorption resin white balls and anhydrous aluminum chloride in dichloromethane, fully swelling the resin, reacting at 60-80 ℃, cooling and discharging, removing the anhydrous aluminum chloride, performing Soxhlet extraction with methanol, and drying to constant weight to obtain the C8-maleic anhydride adsorption resin with high specific surface area.
2. The method according to claim 1, wherein in step (1), the dispersing agent is selected from one or more of gelatin, polyvinyl alcohol, poly (meth) acrylate, talc and kaolin, and the inorganic salt is selected from one or more of sodium sulfate, sodium chloride, potassium chloride and potassium sulfate.
3. The method according to claim 1 or 2, wherein in the step (1), the mass concentration of the dispersant in the aqueous phase is 0.08 to 0.8%, and the mass concentration of the inorganic salt is 0.4 to 1%.
4. The process according to any one of claims 1 to 3, wherein in step (1), the crosslinking agent is selected from one or more of divinylbenzene, trivinylbenzene, divinyltoluene, divinylethylbenzene, ethylene glycol dimethacrylate and allyl methacrylate, and the initiator is selected from one or more of oil-soluble azo-based radical initiators, oil-soluble peroxide-based radical initiators and oil-soluble redox initiation systems.
5. The method according to any one of claims 1 to 4, wherein in step (1), the maleic anhydride accounts for 1 to 8% by mass of the C8 fraction, the crosslinking agent accounts for 2 to 30% by mass of the C8 fraction, and the initiator accounts for 0.2 to 2% by mass of the total of the maleic anhydride, the C8 fraction and the crosslinking agent.
6. The method according to any one of claims 1 to 5, wherein in the step (1), the aqueous phase is heated to 25 to 60 ℃ after being added to the reaction kettle; the volume ratio of the water phase to the oil phase is 3-4: 1.
7. the method according to any one of claims 1 to 6, wherein in the step (1), the temperature rise reaction is carried out for 3 to 5 hours by raising the temperature to 40 to 80 ℃, and is further raised to 55 to 95 ℃ for 3 to 5 hours.
8. The method according to any one of claims 1 to 7, wherein in the step (2), the mass ratio of the resin white balls to the anhydrous aluminum chloride is 5-10:1, and the amount of the dichloromethane is 3-15 times of the volume of the resin white balls.
9. The method according to any one of claims 1 to 8, wherein in step (2), the reaction is carried out at 60 to 80 ℃ for 10 to 15 hours; drying in a vacuum drying oven at 60-80 deg.C.
10. A method for removing dinotefuran residues, which comprises adsorbing with the adsorbent resin prepared by the method of any one of claims 1 to 9.
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| CN101912770A (en) * | 2010-09-03 | 2010-12-15 | 中国科学院长春应用化学研究所 | Polymeric adsorbent and preparation method thereof |
| CN105949388A (en) * | 2016-05-23 | 2016-09-21 | 北京化工大学 | Functional copolymer directly prepared from higher olefin mixture and preparation method |
| CN115598233A (en) * | 2022-08-26 | 2023-01-13 | 中国地质大学（武汉）（Cn） | Gel adsorption film, gradient diffusion device and application of gel adsorption film and gradient diffusion device in neonicotinoid pesticide sampling |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1618827A (en) * | 2004-10-18 | 2005-05-25 | 河北宝硕集团有限公司化工分公司 | C9 maleic anhydride copolymer and its preparation method |
| JP2008001681A (en) * | 2005-12-01 | 2008-01-10 | Sumitomo Chemical Co Ltd | 3-iminopropene compound, pesticide containing the same, and application thereof to controlling noxious organism |
| CN101058068A (en) * | 2007-05-31 | 2007-10-24 | 浙江工商大学 | Macroporous adsorption resin special used for separating antibiotic and its preparation method |
| CN101912770A (en) * | 2010-09-03 | 2010-12-15 | 中国科学院长春应用化学研究所 | Polymeric adsorbent and preparation method thereof |
| CN105949388A (en) * | 2016-05-23 | 2016-09-21 | 北京化工大学 | Functional copolymer directly prepared from higher olefin mixture and preparation method |
| CN115598233A (en) * | 2022-08-26 | 2023-01-13 | 中国地质大学（武汉）（Cn） | Gel adsorption film, gradient diffusion device and application of gel adsorption film and gradient diffusion device in neonicotinoid pesticide sampling |
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