CN103341349B - A kind of imidazoles and chitosan functional magnetic particle and its preparation method and application - Google Patents
A kind of imidazoles and chitosan functional magnetic particle and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of imidazoles and chitosan functional magnetic particle and its preparation method and application.Described imidazoles and chitosan functional magnetic particle are the Fe that imidazoles and chitosan are modified jointly
3o
4magnetic particle, is expressed as: Fe
3o
4oACTS-g-IMZ, in formula, OA represents oleic acid, and CTS represents chitosan, and IMZ represents imidazoles.Method building-up process provided by the invention is convenient, economical and have and the magnetic particle preparation method and application of eco-friendly imidazoles and chitosan common modification good compared with more function group, selectivity, use the imidazoles of the present invention and chitin modified magnetic particle, sulfonic acid dye in water sample can be removed efficiently, simply, fast, innocuously.
Description
Technical field
The present invention relates to a kind of functional magnetic particle preparation method and application, especially relate to magnetic particle of a kind of imidazoles and chitosan functionalization and its preparation method and application.
Background technology
At present, remove the main method of sulfonic acid dye in waste water and have chemical oxidization method, membrane separation process, flocculence, absorption method, microbial degradation method etc., these methods respectively have advantage, but also exist and need use a large amount of organic solvents, product recovery rate is low, economic benefit is undesirable, complex operation and secondary pollution problems.
Functional magnetic particle because of its surface can functionalization, there is good selectivity, and can in magnetic field rapid directional separation, therefore, have broad application prospects removing in the sulfonic acid dye in waste water.
At present, the research work for removing the sorbing material of Wastewater Dyes has achieved certain achievement.201210121603.8 disclose on August 15th, 2012 the dye adsorption material that a kind of Pericarpium Musae makes, and its preparation method is: (1) cleans Pericarpium Musae with water, and then making beating is banana latex, and banana latex is sent into fermentor tank; (2) bacterial classification is inoculated in fermentor tank, ventilating fermentation; (3) the product solid-liquid separation in fermentor tank, collects after solid part washing; (4) solid part drying, pulverizing.The dyestuff of 40-60% in the adsorbable dyestuff waste liquid of this sorbing material, removal efficiency is lower, and can not reuse, and also needs the operation of complexity such as filtering, centrifugal, time-consuming effort.201110116052.1 disclose a kind of dyestuff of removing on September 14th, 2011 can the preparation method of novel absorption material of magnetic resolution, and synthesis step is as follows: will adopt chemical Vapor deposition process gained carbon nanotube primary sample, ultrasonic disperse is in distilled water.Add a certain amount of oxidizing solution, solution is placed in magnetic stirring apparatus, at a certain temperature back flow reaction a few hours.By modified magnetic carbon nano-tube sample filtering, washing, vacuum-drying, magnetic carbon nano-tube composite adsorbing material can be obtained.This magnetic carbon nano-tube composite adsorbing material is stablized and is had good dispersing property in aqueous, have good removal effect, but the selectivity of this material is poor to dyestuff, and not reproducible use, required carbon nano-tube material is expensive, and source is not enriched, and is difficult to industrialization.201110219902.0 disclose a kind of preparation method and application of dye adsorption material on February 6th, 2013.The present invention utilizes cdear needle to dry to pulverize, and utilizes alcohol degreasing, de-organic pigment, and rinse through phosphoric acid buffer, redeposition is dried, and makes sorbing material and for the removal of dyestuff after sieving.The removal efficiency of this biological adsorption material to dyestuff is high, and preparation process is simple, and aspect of drawing materials, material are sufficient, cost is lower, but sorbing material cannot recycle, and needs the operation of complexity such as filtering, centrifugal, time-consuming effort.201210112650 disclose a kind of preparation method with the magnetic mesoporous carbon nanometer micro ball of high absorption property on August 1st, 2012, and the method for its solvent-applied heat introduces Fe in mesoporous carbon
3o
4magnetic particle, prepares a kind of mesoporous carbon microballoon with high saturation degree, uses it for removing of the pollutents such as the dyestuff in waste water.The magnetic mesoporous carbon nanometer micro ball of preparation has high specific surface area (741.8m
2g
-1), the fields such as water treatment, support of the catalyst and biomedicine can be widely used in, but selectivity is good not.201110020472.X discloses on June 29th, 2011 method that sulfonic-group-containing dye in alkaline waste water removed by chitosan magnetic sorbing material, preparation method is as follows: chitosan is dissolved in ferric chloride in aqueous solution by (1), stir, separate out solid after adding ethanol, solid after filtration, washing after and nano-magnetic Fe
3o
4mixing, then carry out crosslinking reaction with glutaraldehyde water solution, obtain chitosan magnetic sorbing material through aftertreatment after crosslinking reaction completes; (2) chitosan magnetic is joined in the aqueous solution containing sulfonic group dyestuff, stir, filter, be recycled solution and the chitosan magnetic sorbing material of dyestuff.The method is simple to operate, environmental friendliness and with low cost, but functional group is relatively less, can affect the saturated extent of adsorption of sorbent material p-sulfonic acid radical dye.
Dye adsorption material category is various, as the materials such as gac, carbon nanotube, zeolite can as sorbing material.Take chitosan as the natural dyestuff sorbing material of representative, wide material sources, cheap, receive much concern.Imidazoles cheap and easy to get is a kind of easily protonated material, has good absorption to the pollutent existed with anionic form.Thus, by common for this bi-material modified magnetic Fe
3o
4, obtain being rich in functional group-NH
2,-NH-magnetic particle, can effectively remove in waste water with anionic form exist sulfonic acid dye.
That commonly uses at present removes in the sorbing material of the sulfonic group dyestuff in waste water, and selectivity is poor, and functional group is relatively less and single.Known with regard to our document of retrieval, prepare the magnetic particle of imidazoles and the common functionalization of chitosan, and be applied to the research removed with MO, CR and ACBK tri-kinds of sulphonic acids dyestuffs in recycle-water and have no reported in literature.
Summary of the invention
The technical problem to be solved in the present invention is, overcomes the deficiencies in the prior art, provides a kind of imidazoles and chitosan functional magnetic particle and its preparation method and application.
The modified magnetic particle of the present invention is the magnetic particle of imidazoles and chitosan functionalization, is expressed as: Fe
3o
4oACTS-g-IMZ, in formula, OA represents oleic acid, and CTS represents chitosan, and IMZ represents imidazoles.
The preparation method of the functional magnetic particle of the present invention, comprises the following steps:
(1) Fe
3o
4the synthetic method of OA: at 25 DEG C, by 5.8gFe (NO
3) 9H
2o and 2.3gFeSO
46H
2o adds in three-necked bottle, adds the 100mL redistilled water of logical nitrogen 30min deoxidation, mechanical stirring 5min under nitrogen protection, adds 10mL strong aqua in three-necked bottle, continues mechanical stirring 10min, then adds 1.0g oleic acid, mechanical stirring 1h.Shift out, washing, to neutral, obtains Fe
3o
4oA, stand-by.
The mol ratio of described trivalent iron salt and divalent iron salt is 1: 0.5.
(2) Fe
3o
4the synthetic method of OACTS-g-IMZ; By dried Fe
3o
4oA magnetic particle is scattered in 50mL redistilled water again, is transferred in three-necked bottle, mechanical stirring 10min under room temperature; Add 50mL3% chitosan solution (using 1% acetate dissolution), 0.23gSDS, continue to stir 10min; Add 25mL imidazole solution, then add 2mLECH, be warming up to 70 DEG C, reaction 16h; Shift out, washing is extremely neutral, and 70 DEG C of vacuum-drying 24h are stand-by.In whole process, stirring velocity is 1200rmin
-1.
The preparation of described imidazole solution: be dissolved in by 1.5gIMZ in the mixing solutions of 25mLNaOH solution/methyl alcohol, wherein the mixing solutions of NaOH and methyl alcohol is: V (NaOH): V (methyl alcohol)=1: 4, ultrasonic agitation, is uniformly dispersed.In mixed solution, the concentration of NaOH is 2M.
The imidazoles of the present invention and chitosan functional magnetic particle are applied to and remove sulfonic acid dye in waste water, comprise the following steps:
(1) preparation of simulated wastewater: the dyestuff storing solution pipetting a certain amount of MO, CR, ACBK respectively, being diluted to concentration with deionized water is 100mgL
-1homogencous dyes standardized solution, and be placed in the refrigerator of 4 DEG C for subsequent use;
(2) MO, CO and ABCK sample solution pH is regulated to be 2 ~ 12; Claim 20mgFe
3o
4the functional magnetic particle of OACTS-g-IMZ, in 25mL volumetric flask, adds 10.00mL10mgL
-1sample solution (MO, CR or ACBK solution), 10 DEG C ~ 50 DEG C constant temperature oscillation absorption; After 5 ~ 25min time, taken out by sample, Magneto separate, shifts out solution, stand-by.
(3) magnetic particle is with after second distillation water washing three times, uses 10.00mL0.8molL
-1naOH/ acetone (V: V=80: 20) wash-out MO, CR and ACBK, Magneto separate, obtains strip liquor and magnetic particle;
(4) respectively to feed liquid after stock liquid, extraction and strip liquor sampling, regulate pH to be 6, measure their concentration by visible/UV-detector.
The top condition of described subtractive process is: the optimal ph of MO, CR and ACBK is 4; Temperature of reaction is 30 DEG C; Extraction time is 10min; Stripping times 10min.
Advantage of the present invention: (1) magnetic particle particle diameter is little, is rich in comparatively more function group, is easy to be combined with electrostatic interaction with target substance; Research shows, removes the sulfonic acid dye in waste water with the magnetic particle of imidazoles and chitosan functionalization, and speed is fast, and removal efficiency is high, and magnetic particle is reusable; (2) due to the distinctive magnetic responsiveness of magnetic particle self of imidazoles and chitosan functionalization, promptly can be separated under the effect of externally-applied magnetic field, not need centrifugally operated, be conducive to simplification and the automatization of sepn process; (3) adopt the imidazoles of cheap and easy to get, abundance and chitosan to Fe
4o
3modification, not only reduces cost, can also effectively remove and the sulfonic acid dye reclaimed in waste water; (4) the whole process removing sulfonic acid dye does not use noxious solvent, both can not affect the healthy of operator, can not cause secondary pollution again; (5) whole process operation is simple, consuming time short, can raise the efficiency, and saves manpower and the energy.
Accompanying drawing explanation
Fig. 1 is imidazoles and the chitosan functional magnetic particle Fe of embodiment 1
3o
4the transmission electron microscope figure of OACTS-g-IMZ;
Fig. 2 is the Fe of embodiment 1
3o
4oACTS-g-IMZ (c), Fe
3o
4oACTS (b) and Fe
3o
4the infared spectrum of (a) three kinds of magnetic particles;
Fig. 3 is the Fe of embodiment 1
3o
4oACTS-g-IMZ (c), Fe
3o
4oACTS (b) and Fe
3o
4the X-ray diffractogram of (a) three kinds of magnetic particles;
Fig. 4 is the Fe of embodiment 1
3o
4oACTS-g-IMZ (c), Fe
3o
4oA (b) and Fe
3o
4the magnetic hysteresis loop figure of (a) three kinds of magnetic particles;
Fig. 5 is the Fe of embodiment 1
3o
4the N of OACTS-g-IMZ
2(in figure, illustration is Fe to adsorption and desorption figure
3o
4the pore volume of OACTS-g-IMZ and graph of pore diameter distribution.
Fig. 6 is the Fe of embodiment 1
3o
4oACTS-g-IMZ access times are on the impact of the decreasing ratio of MO, CR and ACBK tri-kinds of sulfonic acid dye.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.
Embodiment 1
The imidazoles of the present embodiment and chitosan functional magnetic particle Fe
3o
4the preparation method of OACTS-g-IMZ, comprises the following steps:
(1) Fe
3o
4the synthetic method of OA: at 25 DEG C, by 5.8gFe (NO
3) 9H
2o and 2.3gFeSO
46H
2o adds in three-necked bottle, adds the 100mL redistilled water of logical nitrogen 30min deoxidation, mechanical stirring 5min under nitrogen protection, adds 10mL strong aqua in three-necked bottle, continues mechanical stirring 10min, then adds 1.0g oleic acid, mechanical stirring 1h.Shift out, washing, to neutral, obtains Fe
3o
4oA, stand-by.
The mol ratio of described trivalent iron salt and divalent iron salt is 1: 0.5.
(2) Fe
3o
4the synthetic method of OACTS-g-IMZ; By dried Fe
3o
4oA magnetic particle is scattered in 50mL redistilled water again, is transferred in three-necked bottle, mechanical stirring 10min under room temperature; Add 50mL3% chitosan solution (using 1% acetate dissolution), 0.23gSDS, continue to stir 10min; Add 25mL imidazole solution, then add 2mLECH, be warming up to 70 DEG C, reaction 16h; Shift out, washing is extremely neutral, and 70 DEG C of vacuum-drying 24h are stand-by.In whole process, stirring velocity is 1200rmin
-1.
The preparation of described imidazole solution: be dissolved in by 1.5gIMZ in the mixing solutions of 25mLNaOH solution/methyl alcohol, wherein the mixing solutions of NaOH and methyl alcohol is: V (NaOH): V (methyl alcohol)=1: 4, ultrasonic agitation, is uniformly dispersed.In mixed solution, the concentration of NaOH is 2M.
Adopt transmission electron microscope, Fourier transform infrared spectrometer, X-ray diffraction analysis instrument, vibrating sample magnetometer and specific surface area measuring instrument to the imidazoles of preparation and chitosan functional magnetic particle Fe
3o
4oACTS-g-IMZ characterizes, see accompanying drawing 1-Fig. 5.Characterization result shows: this magnetic particle is substantially spherical in shape, and have hole to exist, median size is about 90nm, has good superparamagnetism and stability, and the N of magnetic particle
2isothermal adsorption meets IV isothermal adsorption patterns.
The imidazoles of the present embodiment and chitosan functional magnetic particle are applied to and remove sulfonic acid dye in waste water, comprise the following steps:
(1) preparation of standardized solution: accurately take 0.50g analytical pure MO, CR, ACBK respectively in 500mL volumetric flask, after being dissolved in water, constant volume; Pipette a certain amount of dyestuff storing solution respectively, be diluted to 100mgL with deionized water
-1homogencous dyes standardized solution, and then be diluted to the standardized solution of a series of different concns.Storing solution and standardized solution are placed in the refrigerator of 4 DEG C for subsequent use.
The preparation of simulated wastewater: the dyestuff storing solution pipetting a certain amount of MO, CR and ACBK respectively, being diluted to concentration with deionized water is all 100mgL
-1homogencous dyes standardized solution, and be placed in the refrigerator of 4 DEG C for subsequent use;
(2) MO, CR and ACBK sample solution pH is regulated to be 4; Claim 20mgFe
3o
4the functional magnetic particle of OACTS-g-IMZ, in 25mL volumetric flask, adds 10.00mL10mgL
-1sample solution (MO, CR or ACBK solution), when 30 DEG C, constant temperature oscillation 10min, taken out by sample, Magneto separate, shifts out solution, stand-by.
(3) magnetic particle is with after second distillation water washing three times, uses 10.00mL0.8molL
-1naOH/ acetone (V: V=80: 20) wash-out MO, CR and ACBK, Magneto separate, obtains strip liquor and magnetic particle;
(4) respectively to feed liquid after stock liquid, extraction and strip liquor sampling, regulate pH to be 6, measure their concentration by visible/UV-detector.Parallelly do three experiments.
The determined wavelength of above-mentioned three kinds of sulfonic acid dye MO, CR and ACBK is respectively: 464nm, 499nm, 522nm; Filter with the wetting ability polypropylene filtering membrane in 0.45 aperture before sample detection.
Final analysis result shows: Fe
3o
4the functional magnetic particle of OACTS-g-IMZ is fine to the removal effect of these three kinds of sulfonic acid dye of MO, CR and ACBK, and decreasing ratio corresponding when homogencous dyes removes is respectively 92.1%, 93.2%, 94.3%; Use 10.00mL0.8molL
-1naOH/ acetone (V: V=80: 20) back extraction MO, CO and ABCK, the rate of recovery is all more than 90%.
This magnetic particle particle reproducible utilization, recycles five times, and nearly all do not change the decreasing ratio of these three kinds of sulfonic acid dye of MO, CR and ACBK, its result as shown in Figure 6.
Embodiment 2
The chitosan functional magnetic particle Fe of the present embodiment
3o
4the preparation method of OACTS, comprises the following steps:
(1) Fe
3o
4the synthetic method of OA: at 25 DEG C, by 5.8gFe (NO
3) 9H
2o and 2.3gFeSO
46H
2o adds in three-necked bottle, adds the 100mL redistilled water of logical nitrogen 30min deoxidation, mechanical stirring 5min under nitrogen protection, adds 10mL strong aqua in three-necked bottle, continues mechanical stirring 10min, then adds 1.0g oleic acid, mechanical stirring 1h.Shift out, washing, to neutral, obtains Fe
3o
4oA, stand-by.
The mol ratio of described trivalent iron salt and divalent iron salt is 1: 0.5.
(2) Fe
3o
4the synthetic method of OACTS; By dried Fe
3o
4oA magnetic particle is scattered in 50mL redistilled water again, is transferred in three-necked bottle, mechanical stirring 10min under room temperature; Add 50mL3% chitosan solution (using 1% acetate dissolution), 0.23gSDS, continue to stir 10min; Add 2mLECH again, be warming up to 70 DEG C, reaction 16h; Shift out, washing is extremely neutral, and 70 DEG C of vacuum-drying 24h are stand-by.In whole process, stirring velocity is 1200rmin
-1.
The imidazoles of the present embodiment and the magnetic particle of chitosan functionalization are applied to and remove sulfonic acid dye in waste water, comprise the following steps:
(1) preparation of standardized solution: accurately take 0.50g analytical pure MO, CR, ACBK respectively in 500mL volumetric flask, after being dissolved in water, constant volume; Pipette a certain amount of dyestuff deposit respectively, be diluted to 100mgL with deionized water
-1homogencous dyes standardized solution, and then be diluted to the standardized solution of a series of different concns.Storing solution and standardized solution are placed in the refrigerator of 4 DEG C for subsequent use.
The preparation of simulated wastewater: the dyestuff storing solution pipetting a certain amount of MO, CR and ACBK respectively, being diluted to concentration with deionized water is all 100mgL
-1homogencous dyes standardized solution, and be placed in the refrigerator of 4 DEG C for subsequent use;
(2) MO, CR and ACBK sample solution pH is regulated to be 4; Claim 20mgFe
3o
4the functional magnetic particle of OACTS, in 25mL volumetric flask, adds 10.00mL10mgL
-1sample solution (MO, CR or ACBK solution), when 30 DEG C, constant temperature oscillation 10min, taken out by sample, Magneto separate, shifts out solution, stand-by.
(3) magnetic particle is with after second distillation water washing three times, uses 10.00mL0.8molL
-1naOH/ acetone (V: V=80: 20) wash-out MO, CR and ACBK, Magneto separate, obtains strip liquor and magnetic particle;
(4) respectively to feed liquid after stock liquid, extraction and strip liquor sampling, regulate pH to be 6, measure their concentration by visible/UV-detector.Parallelly do three experiments.
Embodiment 3
The imidazoles of the present embodiment and the preparation method of chitosan functional magnetic particle, comprise the following steps:
(1) Fe
3o
4the synthetic method of OA: at 25 DEG C, by 5.8gFe (NO
3) 9H
2o and 2.3gFeSO
46H
2o adds in three-necked bottle, adds the 100mL redistilled water of logical nitrogen 30min deoxidation, mechanical stirring 5min under nitrogen protection, adds 10mL strong aqua in three-necked bottle, continues mechanical stirring 10min, then adds 1.0g oleic acid, mechanical stirring 1h.Shift out, washing, to neutral, obtains Fe
3o
4oA, stand-by.
The mol ratio of described trivalent iron salt and divalent iron salt is 1: 0.5.
(2) Fe
3o
4the synthetic method of OACTS-g-IMZ; By dried Fe
3o
4oA magnetic particle is scattered in 50mL redistilled water again, is transferred in three-necked bottle, mechanical stirring 10min under room temperature; Add 50mL3% chitosan solution (using 1% acetate dissolution), 0.23gSDS, continue to stir 10min; Add 25mL imidazole solution, then add 2mLECH, be warming up to 70 DEG C, reaction 16h; Shift out, washing is extremely neutral, and 70 DEG C of vacuum-drying 24h are stand-by.In whole process, stirring velocity is 1200rmin
-1.
The preparation of described imidazole solution: be dissolved in by 1.5gIMZ in the mixing solutions of 25mLKOH solution/methyl alcohol, wherein the mixing solutions of KOH and methyl alcohol is: V (KOH): V (methyl alcohol)=1: 4, ultrasonic agitation, is uniformly dispersed.In mixed solution, the concentration of KOH is 2M.
The imidazoles of the present embodiment and chitosan functional magnetic particle are applied to and remove sulfonic acid dye in waste water, comprise the following steps:
(1) preparation of standardized solution: accurately take 0.50g analytical pure MO, CR, ACBK respectively in 500mL volumetric flask, after being dissolved in water, constant volume; Pipette a certain amount of dyestuff storing solution respectively, be diluted to 100mgL with deionized water
-1homogencous dyes standardized solution, and then be diluted to the standardized solution of a series of different concns.Storing solution and standardized solution are placed in the refrigerator of 4 DEG C for subsequent use.
The preparation of simulated wastewater: the dyestuff storing solution pipetting a certain amount of MO, CR and ACBK respectively, being diluted to concentration with deionized water is all 100mgL
-1homogencous dyes standardized solution, and be placed in the refrigerator of 4 DEG C for subsequent use;
(2) MO, CR and ACBK sample solution pH is regulated to be 4; Claim 20mgFe
3o
4the functional magnetic particle of OACTS-g-IMZ, in 25mL volumetric flask, adds 10.00mL10mgL
-1sample solution (MO, CR or ACBK solution), when 30 DEG C, constant temperature oscillation 10min, taken out by sample, Magneto separate, shifts out solution, stand-by.
(3) magnetic particle is with after second distillation water washing three times, uses 10.00mL0.8molL
-1naOH/ acetone (V: V=80: 20) wash-out MO, CR and ACBK, Magneto separate, obtains strip liquor and magnetic particle;
(4) respectively to feed liquid after stock liquid, extraction and strip liquor sampling, regulate pH to be 6, measure their concentration by visible/UV-detector.Parallelly do three experiments.
Should be understood that, for those of ordinary skills, can be improved according to the above description or convert, and all these improve and convert the protection domain that all should belong to claims of the present invention.
Claims (3)
1. a preparation method for imidazoles and chitosan functional magnetic particle, is characterized in that, comprise the following steps:
(1) Fe
3o
4the synthetic method of OA: at 25 DEG C, by 5.8gFe (NO
3)
39H
2o and 2.3gFeSO
46H
2o adds in three-necked bottle, adds the 100mL redistilled water of logical nitrogen 30min deoxidation, mechanical stirring 5min under nitrogen protection, adds 10mL strong aqua in three-necked bottle; continue mechanical stirring 10min, then add 1.0g oleic acid, mechanical stirring 1h; shift out, washing, to neutral, obtains Fe
3o
4oA, stand-by;
(2) Fe
3o
4the synthetic method of OACTS-g-IMZ: by dried Fe
3o
4oA magnetic particle is scattered in redistilled water again, is transferred in three-necked bottle, mechanical stirring 10min under room temperature; Add 50mL3% chitosan solution, 0.23g sodium laurylsulfonate, continue to stir 10min; Add imidazole solution, then add 2mL epoxy chloropropane, be warming up to 70 DEG C, reaction 16h; Shift out, washing is extremely neutral, and 70 DEG C of vacuum-drying 24h are stand-by; In whole process, stirring velocity is 1200rmin
-1;
The preparation of described imidazole solution: be dissolved in by 1.5g imidazoles in the mixing solutions of 25mLNaOH solution/methyl alcohol, wherein the mixing solutions of NaOH and methyl alcohol is: V (NaOH): V (methyl alcohol)=1: 4, ultrasonic agitation, is uniformly dispersed.
2. the imidazoles prepared of preparation method as claimed in claim 1 and a chitosan functional magnetic particle, it is characterized in that, be the Fe that imidazoles and chitosan are modified jointly
3o
4magnetic particle, is expressed as: Fe
3o
4oACTS-g-IMZ, in formula, OA represents oleic acid, and CTS represents chitosan, and IMZ represents imidazoles.
3. imidazoles as claimed in claim 2 and chitosan functional magnetic particle are removing the application in waste water in sulfonic acid dye.
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