CN105170103A - Furfural-modified crosslinked-chitosan chelate resin magnetic particles and preparation method - Google Patents
Furfural-modified crosslinked-chitosan chelate resin magnetic particles and preparation method Download PDFInfo
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Abstract
The invention provides furfural-modified crosslinked-chitosan chelate resin magnetic particles and a preparation method. The preparation method comprises the steps that chitosan and furfural are taken as raw materials, and furfural-modified chitosan is synthesized; glutaraldehyde is adopted as a cross-linking agent and is subjected to a cross-linking reaction with the furfural-modified chitosan, the surface of Fe3O4 particles is coated with crosslinked chitosan, and the furfural-modified crosslinked-chitosan chelate resin magnetic particles are prepared. The furfural-modified crosslinked-chitosan chelate resin magnetic particles overcome the defect that the chitosan is prone to being dissolved to be lost in an acid solution, can be repeatedly used and quickly separated out from wastewater in a magnetic field and solves the problems of suspension operation of common chelate resin to enable liquid-solid separation to be easier. The furfural-modified crosslinked-chitosan chelate resin magnetic particles are moderate in swelling ratio, good in heat stability, high in adsorption capacity to metal ions such as Hg<2+>, Pb<2+>, Ni<2+> and Co<2+> in the wastewater, low in preparation cost, easy to recover and the like.
Description
Technical field
What the present invention relates to is a kind of cross-linked chitosan chelating resin magnetic-particle, the present invention also relates to a kind of preparation method of cross-linked chitosan chelating resin magnetic-particle.
Background technology
In the last few years, along with the industry fast development such as China's metallurgy, medicine, dyestuff, the thing followed all to discharge a large amount of industrial wastewater containing contents of many kinds of heavy metal ion every year.Heavy metal ion is in water or exists in soil and all cannot be biodegradable, and being discharged into environment will become permanent pollution.Once enter in human body or in organism, can cumulative effect be produced, all can cause serious harm to the mankind and other biological.In addition, heavy metal resources, also day by day exhausted, therefore, to process the sewage containing heavy metal ion and the recycling of heavy metal ion causes the concern of people gradually.
The chelating resin that conventional method is used for sewage disposal is generally divided into the functional high molecule material of Prof. Du Yucang and the natural macromolecular material of modification, as D.Prabhakaran etc. utilizes 2,3,4-tri hydroxybenzaldehyde and ethylenediamine react, obtain two (2,3,4-trihydroxy benzyl) ethylenediamine, then this function base is connected on the resin matrix of polystyrene-divinylbenzene, for the absorption of actinium series and transition metal ions.Result of study shows, this resin is to U
6+, Th
4+, Pb
2+, Cd
2+the Optimal pH of absorption is respectively 4.0 ~ 5.0,1.0 ~ 2.0,6.0 ~ 6.5,6.5; Adsorption capacity is respectively 1.43mmol/g, 1.19mmol/g, 1.01mmol/g, 0.78mmol/g (D.Prabhakaran, M.S.Subramanian.Selectiveextractionandsequentialseparati onofactinideandtransitionionsusingAXAD-16-BTBEDpolymeric sorbent [J] .ReactiveandFunctionalPolymers, 2003,57 (2): 147-155).Etc. be JainV.K. raw material with o-vanillin, itself and thiosemicarbazides reacted and generates o-vanillin thiosemicarbazones, then connect on polystyrene matrix by coupling reaction, obtain containing o-vanillin thiosemicarbazones chelating resin.Resin adsorption Cu
2+, Zn
2+, Pb
2+optimum PH range be 2.5 ~ 4,5.5 ~ 6.5,6.0 ~ 7.5; Adsorbance is respectively 850 μ g/g, 1500 μ g/g, 2000 μ g/g (V.K.Jain, S.S.Sait, P.Shrivastav, Y., K.Agrawal.ApplicationofchelateformingresinAmberliteXAD-2-o-vanillin-thiosemicarbazonetotheseparationandpreconcent rationofcopper (II), zinc (II) andlead (II) [J] .Talanta, 1997,45 (2): 397-404).
Chitin is a kind of abundant, reproducible natural resources, and its part deacetylation product shitosan, owing to having biocompatibility, biological degradability, hydrophily and the advantage such as nontoxic, is widely used in many fields.Be rich in amino and hydroxyl in chitosan molecule main chain, can with heavy metal ion generation coordination, therefore, heavy metal ion has certain selective adsorption capacity, reaches the object of heavy metal ion in removal and enrichment waste water.But the easily swelling in acid condition and softening loss of shitosan, can not repeatedly use.The deficiency that crosslinked and modification not only overcomes the protonated loss of amino of chitosan is carried out to natural chitosan, and due to chitosan molecule chain containing amino and hydroxyl, easily can introduce other adsorption function groups, thus the adsorption capacity of shitosan heavy metal ion can be improved.Sun Bo etc. adopt the materials such as ASPARTIC ACID, 1B and TGA to carry out modification to natural chitosan, with glutaraldehyde as cross linker, synthesize one and there is peptide-polysaccharide like structure copolymer, by adding-NH in chelating resin to the modification of natural chitosan
2quantity, and introduce sulfydryl, improve the adsorption capacity of chelating resin, but this copolymeric material is only applicable to the sewage solution system of extremely low concentration, saturated extent of adsorption is lower, and swelling ratio is comparatively large, is unfavorable for bed operation (China Patent Publication No.: CN1869105).Chen Xingjuan etc. take ASPARTIC ACID as raw material, and phosphoric acid is catalyst, synthesis polysuccinimide, react with CYSTINE again, carry out cross-linking modified to shitosan further, prepare cross-linked chitosan derivative chelating resin, single step reaction introduction-NH in chelating resin molecule
2with-S-S-functional group, to Hg
2+, Pb
2+, Ni
2+, Co
2+significantly improve etc. adsorption of metal ions capacity, swelling ratio is moderate, Heat stability is good, the low (Chinese Patent Application No.: 201210189467.6) of resin preparation cost.It is little that Properties of Magnetic Chelating Resins has particle diameter, and the strong and easy advantage such as recovery of adsorption function, particularly can carry out solid-liquor separation fast by resin and waste water, overcome difficulty during common chelating resin suspension procedure from magnetic field.YehuaZhu etc. have prepared xanthate modified magnetic shitosan, it is to Pb (II), the maximum adsorption capacity of Cu (II) and Zn (II) can reach 76.9mg/g, 34.5mg/g and 20.8mg/g (YehuaZhu, JunHu, JianlongWang.CompetitiveadsorptionofPb (II), Cu (II) andZn (II) ontoxanthate-modifiedmagneticchitosan [J] .JournalofHazardousMaterials, 2012,221-222:155-161).
Summary of the invention
The object of the present invention is to provide and a kind ofly not only to metal ion, there is higher adsorption capacity, and the furfural modified crosslinking Chitosan Chelating Resin magnetic-particle can separated from waste water fast from magnetic field.The present invention also aims to the preparation method of the furfural modified crosslinking Chitosan Chelating Resin magnetic-particle that a kind of simple possible is provided.
The object of the present invention is achieved like this:
The structure of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle of the present invention is as follows:
Wherein, x is more than or equal to 1000; N is less than or equal to 450; M+n is more than or equal to 2300, is less than or equal to 3000.
The preparation method of modified crosslinking Chitosan Chelating Resin magnetic-particle of the present invention is:
(1) first adopt furfural to carry out modification to natural chitosan, in chitosan molecule, introduce more atom N and O atom, to add in resin can with the atomic quantity of metallic ion coordination, improve the absorption property of resin.
(2) with crosslinking agent glutaraldehyde, furfural modification of chitosan is cross-linked further, and is coated on Fe
3o
4the surface of particle, obtains furfural modified crosslinking Chitosan Chelating Resin magnetic-particle.Which overcome the shortcoming of shitosan soluble loss in an acidic solution, can repeatedly use, and there is the advantage separated from waste water fast from magnetic field, overcome difficulty during common chelating resin suspension procedure, make solid-liquor separation easier.
The preparation method of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle of the present invention can also comprise:
1, described take furfural as raw material, and shitosan is matrix, and the method preparing furfural modification of chitosan comprises:
(1) in the reactor that agitating device is housed, add shitosan and 25 ~ 250mL aqueous acetic acid of 0.5 ~ 5g drying successively, constant temperature 50 ~ 80 DEG C, stir and make it all dissolve, obtain water white solution (A).Solution (A) is added in the NaOH solution of 30 ~ 50mL, solution (A) becomes gel particle at once, and constant temperature 50 ~ 80 DEG C stirs 3 ~ 12h, and gel particle becomes the clear gel of thickness, respectively wash three times with distilled water and methyl alcohol, obtain gel (B).Gel (B) after washing is dissolved in a certain amount of methyl alcohol, makes the concentration of shitosan be about 50 ~ 200g/L.Then add furfural, the mol ratio of furfural and shitosan glucose unit is (1 ~ 5): 1, and constant temperature 50 ~ 80 DEG C stirs 3 ~ 12h, obtains lurid sticky mass, respectively washes three times with deionized water and methyl alcohol.The precipitation of collection is put into 50 ~ 80 DEG C of vacuum drying chambers and be dried to constant weight, obtain yellow powder material (C), be furfural modification of chitosan.The concentration of aqueous acetic acid is 1 ~ 3% (v/v).NaOH solution concentration is 1 ~ 5mol/L.
(2) furfural modification of chitosan is cross-linked with crosslinking agent glutaraldehyde described in, and be coated on Fe
3o
4the surface of particle, the method preparing furfural modified crosslinking Chitosan Chelating Resin magnetic-particle comprises: claim 0.5 ~ 5g furfural modification of chitosan (C) to be dissolved in the acetic acid of 12.5 ~ 125mL8% (v/v), obtain pale yellow solution (D).By 0.5 ~ 5gFe
3o
4magnetic-particle is dispersed in 1 ~ 10mL glutaraldehyde, obtains suspension (E).Suspension (E) is dropwise added in pale yellow solution (D), and at 50 ~ 90 DEG C, constant temperature stirs 3 ~ 12h, obtains black mixture (F).Finally remove the Fe be not wrapped by
3o
4particle and not coated chelating resin, remaining mixture 0.1mol/LNaOH solution, distilled water and methyl alcohol respectively wash three times, finally product to be placed in vacuum drying chamber 60 DEG C and to be dried to constant weight, obtain solid matter (G), be furfural modified crosslinking Chitosan Chelating Resin magnetic-particle.Fe
3o
4the particle diameter of magnetic-particle is 100 ~ 1000nm.
The implementation procedure of method of the present invention can be expressed as follows with reaction equation:
Advantage of the present invention and effect: the weak point that the present invention be directed to natural chitosan and modification of chitosan chelating resin thereof, there is provided a kind of preparation method simple, novel and the simple preparation method of the cross-linked chitosan chelating resin magnetic-particle that can repeatedly use, compared with common chelating resin, furfural modified crosslinking Chitosan Chelating Resin magnetic-particle of the present invention not only has higher adsorption capacity to metal ion, and there is inherent magnetic due to chelating resin magnetic-particle, can separate from waste water fast from magnetic field, overcome difficulty during common chelating resin suspension procedure, make solid-liquor separation easier.The resin size prepared is even, and acid and alkali-resistance, has good adsorption effect to contents of many kinds of heavy metal ion in waste water, renewablely reuses.
Furfural modified crosslinking Chitosan Chelating Resin magnetic-particle of the present invention, can be used for containing Ni
2+, Co
2+, Pb
2+, Hg
2+etc. the wastewater treatment of heavy metal ion, convenience Magnetic tools is separated chelating resin and handled waste water.
Accompanying drawing explanation
Fig. 1 is furfural modified crosslinking Chitosan Chelating Resin magnetic-particle infrared spectrogram provided by the invention (adopting KBr pressed disc method);
Fig. 2 is the X-ray diffracting spectrum of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle provided by the invention.
Detailed description of the invention
Illustrate below and the present invention is described in more detail.
Specific embodiment 1
(1) in the 500mL three-necked bottle that agitating device, thermometer and reflux condensate device are housed, add the shitosan of 0.5 ~ 5g drying and the aqueous acetic acid of 25 ~ 250mL3% (v/v) successively, constant temperature 50 ~ 80 DEG C, stirring makes it all dissolve, and obtains water white solution.This solution is added in the NaOH solution of 30 ~ 50mL, solution becomes gel particle at once, 3 ~ 12h is stirred at constant temperature 50 ~ 80 DEG C, gel particle becomes the clear gel of thickness, three times are respectively washed with distilled water and methyl alcohol, by the gel dissolves after washing in a certain amount of methyl alcohol, the concentration of shitosan is made to be about 50 ~ 200g/L.Then add furfural, the mol ratio of furfural and shitosan glucose unit is (1 ~ 5): 1, and constant temperature 50 ~ 80 DEG C stirs 3 ~ 12h, obtains lurid sticky mass, respectively washes three times with deionized water and methyl alcohol.The precipitation of collection is put into 50 ~ 80 DEG C of vacuum drying chambers and be dried to constant weight, obtain yellow powder material and be furfural modification of chitosan (1).
(2) claim 0.5 ~ 5g furfural modification of chitosan (1) to be dissolved in the aqueous acetic acid of 12.5 ~ 125mL8% (v/v), obtain pale yellow solution.Be the Fe of 200 ~ 300nm by 0.5 ~ 5g particle diameter
3o
4magnetic-particle is dispersed in 1 ~ 10mL glutaraldehyde, obtains suspension.Suspension is dropwise added in above-mentioned pale yellow solution, and at 50 ~ 90 DEG C, constant temperature stirs 3 ~ 12h, obtains black mixture, removes the Fe be not wrapped by
3o
4particle and not coated chelating resin, remaining mixture 0.1mol/LNaOH solution, distilled water and methyl alcohol respectively wash three times, finally product to be placed in vacuum drying chamber 60 DEG C and to be dried to constant weight, obtain solid matter (2), be furfural modified crosslinking Chitosan Chelating Resin magnetic-particle.
The chelating resin magnetic-particle obtained can be used for removing containing Ni
2+, Co
2+, Pb
2+, Hg
2+etc. the wastewater treatment of heavy metal ion.
Specific embodiment 2
In the 250mL three-necked bottle that agitating device, thermometer and reflux condensate device are housed, add 2.5g shitosan successively, be dissolved in 125mL1% (v/v) aqueous acetic acid, constant temperature 75 DEG C, magnetic agitation dissolves 6h.Add in the NaOH solution of 2.5mol/L31mL by the shitosan of dissolving, shitosan becomes gel particle at once.Constant temperature 75 DEG C stirs 6h, and gel particle becomes the transparency liquid of thickness, respectively washes three times with distilled water and methyl alcohol.
Be dissolved in the methyl alcohol of 25mL by the shitosan after washing, then add 1.09mL (0.01mol) furfural, make the mass concentration of shitosan be 100g/L, constant temperature 75 DEG C stirs 6h.Three times are respectively washed with deionized water and methyl alcohol.The precipitation of collection is put into 50 DEG C of dry 24h of vacuum drying chamber.Obtain yellow powder furfural modification of chitosan.
Taking 2g furfural modification of chitosan is dissolved in the acetic acid of 50mL8% (v/v), by 2gFe
3o
4be dispersed in 4mL (volume by volume concentration is 50%) glutaraldehyde, and it is dropwise added in the aqueous acetic acid of furfural modification of chitosan, at 60 DEG C, constant temperature stirs 6h, then removes the Fe be not wrapped by
3o
4particle and not coated chelating resin, remaining solid matter 0.1mol/LNaOH solution, distilled water and methyl alcohol respectively wash three times, finally product are placed on 60 DEG C of dry 24h in vacuum drying chamber.Obtain black particle shape material, be furfural modified crosslinking Chitosan Chelating Resin magnetic-particle.
Specific embodiment 3
By furfural modified crosslinking Chitosan Chelating Resin magnetic-particle prepared by embodiment 2, be 6 in room temperature and pH, metal ion initial concentration is 20mg/L, and the dosage of adsorbent is 2g/L, Pb under the condition of adsorption time 8h
2+clearance be 90.7%; To Ni
2+clearance be 87.5%; To Co
2+clearance be 59.2%; To Hg
2+clearance be 86.2%.
By furfural modified crosslinking Chitosan Chelating Resin magnetic-particle prepared by embodiment 2, being analyzed as follows of the typical absorption peak of its infrared spectrogram:
3422cm
-1for-OH stretching vibration absworption peak; 2922cm
-1for the stretching vibration of C-H singly-bound; 1647cm
-1for the overlap of-C=N stretching vibration and C=C double bond stretching vibration peak; 1020cm
-1for C-O singly-bound stretching vibration absworption peak; 595cm
-1for the characteristic absorption peak (see Fig. 1) of Fe-O.
By furfural modified crosslinking Chitosan Chelating Resin magnetic-particle prepared by embodiment 2, being analyzed as follows of its X-ray diffracting spectrum: 30.12 °; 35.44 °; 37.12 °; 53.4 °; 57 ° and 62.56 °, belong to Fe respectively
3o
4the diffraction (see Fig. 2) of the crystal face such as (220), (200), (221), (400), (422) and (511).
Claims (7)
1. a furfural modified crosslinking Chitosan Chelating Resin magnetic-particle, is characterized in that having following structure:
Wherein, x is more than or equal to 1000; N is less than or equal to 450; M+n is more than or equal to 2300, is less than or equal to 3000.
2. a preparation method for furfural modified crosslinking Chitosan Chelating Resin magnetic-particle according to claim 1, is characterized in that comprising the steps:
(1) take furfural as raw material, shitosan is matrix, prepares furfural modification of chitosan;
(2) use glutaraldehyde as cross linker, furfural modification of chitosan is cross-linked, and is coated on Fe
3o
4particle surface, obtains furfural modified crosslinking Chitosan Chelating Resin magnetic-particle.
3. the preparation method of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle according to claim 2, it is characterized in that described furfural modification of chitosan of preparing specifically comprises: in the reactor that agitating device is housed, add 0.5 ~ 5g drying successively shitosan and 25 ~ 250mL aqueous acetic acid, constant temperature 50 ~ 80 DEG C, stirring makes it all dissolve, and obtains water white solution A; Solution A added in the NaOH solution of 30 ~ 50mL, solution A becomes gel particle at once, and constant temperature 50 ~ 80 DEG C stirs 3 ~ 12h, and gel particle becomes the clear gel of thickness, respectively washs three times, obtain gel B with distilled water and methyl alcohol; Gel B after washing is dissolved in methyl alcohol, the concentration of shitosan is made to be 50 ~ 200g/L, then furfural is added, the mol ratio of furfural and shitosan glucose unit is 1 ~ 5:1, and constant temperature 50 ~ 80 DEG C stirs 3 ~ 12h, obtains lurid sticky mass, three times are respectively washed with deionized water and methyl alcohol, the precipitation of collection is put into 50 ~ 80 DEG C of vacuum drying chambers and be dried to constant weight, obtain yellow powder substance C, be furfural modification of chitosan.
4. the preparation method of the furfural modified crosslinking Chitosan Chelating Resin magnetic-particle according to Claims 2 or 3, it is characterized in that the preparation method of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle comprises: claiming 0.5 ~ 5g furfural modification of chitosan C to be dissolved in 12.5 ~ 125mL volume by volume concentration is in the acetic acid of 8%, obtain pale yellow solution D, by 0.5 ~ 5gFe
3o
4magnetic-particle is dispersed in 1 ~ 10mL glutaraldehyde, obtains suspension E, and suspension E is dropwise added in solution D, and at 50 ~ 90 DEG C, constant temperature stirs 3 ~ 12h, obtains black mixture F, finally removes the Fe be not wrapped by
3o
4particle and not coated chelating resin, remaining mixture 0.1mol/LNaOH solution, distilled water and methyl alcohol respectively wash three times, finally product to be placed in vacuum drying chamber 60 DEG C and to be dried to constant weight, obtain solid matter G, be furfural modified crosslinking Chitosan Chelating Resin magnetic-particle.
5. the preparation method of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle according to claim 3, is characterized in that the volume by volume concentration of aqueous acetic acid used is 1 ~ 3%.
6. the preparation method of the furfural modified crosslinking Chitosan Chelating Resin magnetic-particle according to Claims 2 or 3 or 5, is characterized in that Fe used
3o
4the particle diameter of magnetic-particle is 100 ~ 1000nm.
7. the preparation method of furfural modified crosslinking Chitosan Chelating Resin magnetic-particle according to claim 4, is characterized in that Fe used
3o
4the particle diameter of magnetic-particle is 100 ~ 1000nm.
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| CN110115988A (en) * | 2019-06-03 | 2019-08-13 | 湖南泰谷生态工程有限公司 | A kind of processing method of heavy metal ion type industrial wastewater |
| CN110862187A (en) * | 2019-08-16 | 2020-03-06 | 重庆工程职业技术学院 | Artificial wetland for treating industrial wastewater |
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| CN105170103B (en) | 2017-10-31 |
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