CN117205890A - EDTA-SBA-15 adsorbent and preparation method and application thereof - Google Patents
EDTA-SBA-15 adsorbent and preparation method and application thereof Download PDFInfo
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- CN117205890A CN117205890A CN202311324517.1A CN202311324517A CN117205890A CN 117205890 A CN117205890 A CN 117205890A CN 202311324517 A CN202311324517 A CN 202311324517A CN 117205890 A CN117205890 A CN 117205890A
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- 239000003463 adsorbent Substances 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 238000012986 modification Methods 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 abstract description 28
- 150000002500 ions Chemical class 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 3
- 239000002262 Schiff base Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000010586 diagram Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000002336 sorption--desorption measurement Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- -1 aminopropyl groups Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical compound [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 description 1
- 229910000331 cadmium sulfate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- KVICROHOONHSRH-UHFFFAOYSA-N mercury(2+);dinitrate;hydrate Chemical compound O.[Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KVICROHOONHSRH-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001988 small-angle X-ray diffraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention provides an EDTA-SBA-15 adsorbent, a preparation method and application thereof, and relates to the technical field of adsorption materials. According to the invention, schiff base and EDTA are grafted into SBA-15 in sequence, so that the EDTA-SBA-15 adsorbent is obtained. The EDTA-SBA-15 adsorbent prepared by the invention maintains a two-dimensional hexagonal ordered structure of SBA-15, has excellent selectivity and adsorption performance on lead ions in water, and the regenerated EDTA-SBA-15 adsorbent still has excellent adsorption performance and can be reused.
Description
Technical Field
The invention relates to the technical field of adsorption materials, in particular to an EDTA-SBA-15 adsorbent, and a preparation method and application thereof.
Background
The SBA-15 pore canal structure is highly ordered and has single pore diameter distribution, but the SBA-15 is used as an adsorbent, the adsorption performance is relatively poor, and meanwhile, the adsorption performance of the regenerated SBA-15 is obviously reduced, so that the regenerated SBA-15 cannot be repeatedly used for many times. Modification of SBA-15 to increase its adsorption capacity is a hotspot of current research.
Disclosure of Invention
In view of this, the invention provides an EDTA-SBA-15 adsorbent, and a preparation method and application thereof. The invention firstly carries out the process of SBA-15Performing line modification to obtain NH 2 SBA-15, then NH pair with EDTA 2 SBA-15 is modified to obtain EDTA-SBA-15 adsorbent with excellent adsorption performance.
The invention is realized by adopting the following technical scheme:
a preparation method of EDTA-SBA-15 adsorbent comprises the following steps:
s1, synthesizing NH 2 -SBA-15: amino modification is carried out on the inner surface of SBA-15 by using 3-aminopropyl triethoxy silane as a silylating reagent, thereby obtaining NH 2 -SBA-15；
S2, under inert gas, adding 0.04mol of EDTA and 100mL of dichloromethane into a reactor, then dropwise adding 0.04mol of thionyl chloride, and after the dropwise addition is completed, adding 1.0g of NH 2 -SBA-15, at room temperature for 2h;
s3, filtering, washing and vacuum drying after the reaction is finished to obtain the EDTA-SBA-15 adsorbent.
Preferably, NH in step S1 2 The synthesis method of SBA-15 is as follows:
1g of SBA-15 which had been activated in advance at 120℃for 6 hours in vacuo was weighed, then dispersed in anhydrous toluene, 1mL of 3-aminopropyl triethoxysilane was added dropwise, and after mixing well, it was added in N 2 Reflux-reacting for 24h under atmosphere, filtering, washing with toluene and dichloromethane sequentially to remove unreacted 3-aminopropyl triethoxysilane, refluxing with a Soxhlet extractor with diethyl ether/dichloromethane at volume ratio of 1:1 overnight, vacuum-filtering, and vacuum-drying at 60deg.C to obtain NH 2 -SBA-15。
Preferably, the inert gas in step S2 is nitrogen.
Preferably, step S3 is performed by sequentially using DCM, acetone, distilled water, and 0.1M NaHCO 3 The aqueous solution and distilled water were washed.
Preferably, the vacuum drying temperature in step S3 is 45-55 ℃.
The EDTA-SBA-15 adsorbent prepared by the method can be used for adsorbing lead ions in water.
Compared with the prior art, the invention has the following beneficial effects:
the invention uses SOCl 2 As an activating reagent, EDTA is effectively grafted on the surface of an SBA-15 pore canal under mild conditions, and the carboxyl content is 0.908m mol g -1 . The EDTA-SBA-15 adsorbent prepared by the invention contains the advantages of EDTA and SBA-15, has excellent adsorption capacity to Pb (II), and has the maximum adsorption capacity of 273.2mg g calculated according to Langmuir model under experimental conditions -1 。
The EDTA-SBA-15 adsorbent of the invention has good adsorption selectivity to Pb (II) and can be used for preparing the catalyst from Pb 2+ /Hg 2+ /Cd 2+ Selectively adsorbing Pb in metal ion mixed solution of (2) 2+ 。
Drawings
FIG. 1 is a synthetic route diagram of the EDTA-SBA-15 adsorbent of this invention;
FIG. 2 is an X-ray diffraction pattern of SBA-15 before and after modification in accordance with the present invention;
FIG. 3 is a schematic diagram showing the N of SBA-15 before and after modification according to the present invention 2 Adsorption/desorption isotherms and pore size distribution curves;
FIG. 4 is SBA-15, NH 2 -infrared spectra of SBA-15 and EDTA-SBA-15;
FIG. 5 shows the EDTA-SBA-15 adsorbent amount vs. Pb in water according to example 1 of this invention 2+ Influence of adsorption effect;
FIG. 6 shows the adsorption effect of EDTA-SBA-15 adsorbent of example 1 of this invention on each metal ion in an aqueous solution of mixed metal ions;
Detailed Description
The invention will be further illustrated by the following examples
Example 1
A preparation method of EDTA-SBA-15 adsorbent comprises the following steps:
s1, synthesizing NH 2 -SBA-15: amino modification is carried out on the inner surface of SBA-15 by using 3-aminopropyl triethoxy silane as a silylating reagent, thereby obtaining NH 2 -SBA-15; the preparation method comprises the following steps:
1g of SBA-15 which had been activated in advance at 120℃for 6 hours in vacuo was weighed, then dispersed in anhydrous toluene, 1mL of 3-aminopropyl triethoxysilane was added dropwise, and after mixing well, it was added in N 2 Reflux-reacting for 24h under atmosphere, filtering, washing with toluene and dichloromethane sequentially to remove unreacted 3-aminopropyl triethoxysilane, refluxing with a Soxhlet extractor with diethyl ether/dichloromethane at volume ratio of 1:1 overnight, vacuum-filtering, and vacuum-drying at 60deg.C to obtain NH 2 -SBA-15。
S2, under the nitrogen gas, adding 0.04mol of EDTA and 100mL of dichloromethane into a reactor, then dropwise adding 0.04mol of thionyl chloride, and after the dropwise addition is completed, adding 1.0g of NH 2 -SBA-15, at room temperature for 2h;
s3, filtering after the reaction is finished, and then sequentially using DCM, acetone, distilled water and 0.1M NaHCO 3 Washing the aqueous solution and distilled water, and finally drying the aqueous solution at 50 ℃ in vacuum overnight to obtain the EDTA-SBA-15 adsorbent.
For SBA-15, NH in example 1 2 Three materials, SBA-15 and EDTA-SBA-15, were tested, with SAXRD structure parameters shown in Table 1, pore structure parameters shown in Table 2, and elemental analysis shown in Table 3.
TABLE 1
As can be seen from Table 1, the SBA-15 adsorbent is modified by APTES and EDTA chloride sequentially, i.e. the EDTA-SBA-15 of the present invention still maintains the long range order of SBA-15.
TABLE 2
As can be seen from table 2, after grafting the organic groups, the specific surface area and pore volume of the mesopores are significantly reduced, in the order from large to small: SBA-15>NH 2 -SBA-15>EDTA-SBA-15 confirmed that the organic group was assembled on the inner surface of the cell channel.
TABLE 3 Table 3
a Results were derived from back titration tests; b the results are derived from EA; c the results were derived from XPS.
EDTA at NH 2 Grafting rate on SBA-15 was estimated by comparing carboxyl groups and total N content, see Table 3, compared to NH 2 -SBA-15, edta-SBA-15 carboxyl content was significantly increased. During the synthesis, besides EDTA being immobilized on NH 2 SBA-15, no other way to introduce carboxyl groups, EDTA grafted well on NH2-SBA-15. In addition, NH 2 About 80% of the aminopropyl groups in SBA-15 reacted with the acid chloride EDTA, indicating that EDTA was more difficult to incorporate into the silicon wall than APTES.
Experiment one: the EDTA-SBA-15 adsorbent prepared in example 1 is used for carrying out an adsorption experiment on copper ions in a copper sulfate aqueous solution, and the specific experimental process is as follows:
50mL of an aqueous solution of Pb sulfate having a pH of 5.0 was measured, wherein Pb was contained 2+ The concentration is 100mg L -1 Adding EDTA-SBA-15 adsorbent, and oscillating at 25deg.C (150 r min) -1 ) Adsorption was performed for 320min, and the effect of the amount of adsorbent added on the adsorption effect was examined, as shown in fig. 5.
Meanwhile, the invention also researches the influence of the pH value of the water body on the adsorption effect of the EDTA-SBA-15 adsorbent. Pb when the pH was increased from 2.0 to 5.0 2+ The adsorption capacity of (2) rapidly increased from 2.74 to 91.6mg g -1 The adsorption capacity is kept almost unchanged from pH6.0 to 8.0,
experiment II: the EDTA-SBA-15 adsorbent prepared in example 1 was used for carrying out an adsorption experiment on an aqueous solution of mixed metal ions, and the specific experimental procedure is as follows:
preparing mixed metal ion aqueous solution with pH value of 5.0 by using lead sulfate, mercury (II) nitrate hydrate and cadmium sulfate, wherein Pb 2+ The concentration is 100mg L -1 ，Hg 2+ The concentration is 100mg L -1 ，Cd 2+ The concentration is 100mg L -1 ；
Weighing 50mL of the mixed metal ion aqueous solution, adding 50mg of EDTA-SBA-15 adsorbent, and shaking at constant temperature of 25deg.C (150 r min) -1 ) Adsorption is carried out, and the adsorption time is inspected to the metalThe effect of ion adsorption is shown in fig. 6.
As can be seen from FIGS. 5 to 6, the EDTA-SBA-15 adsorbent prepared by the method has very high selectivity and adsorption performance on lead ions in water.
The EDTA-SBA-15 adsorbent after Pb ion adsorption in experiment was regenerated by shaking with 100ml of 0.1M HCl for 4 hours, followed by 0.1M NaHCO 3 The aqueous solution was stirred overnight, filtered and dried to give regenerated EDTA-SBA-15 adsorbent. Experiments were performed using regenerated EDTA-SBA-15 adsorbent to adsorb Pb ions, and the adsorption-desorption process was repeated three times to evaluate the adsorption stability. After four cycles, the adsorption capacity of EDTA-SBA-15 for Pb ions was 87.5mg g -1 The loss is only 4.4%, which shows that the EDTA-SBA-15 has higher adsorption capacity after being used for many times and can be reused.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (7)
1. The preparation method of the EDTA-SBA-15 adsorbent is characterized by comprising the following steps of:
s1, synthesizing NH 2 -SBA-15: amino modification is carried out on the inner surface of SBA-15 by using 3-aminopropyl triethoxy silane as a silylating reagent, thereby obtaining NH 2 -SBA-15；
S2, under inert gas, adding 0.04mol of EDTA and 100mL of dichloromethane into a reactor, then dropwise adding 0.04mol of thionyl chloride, and after the dropwise addition is completed, adding 1.0g of NH 2 -SBA-15, at room temperature for 2h;
s3, filtering, washing and vacuum drying after the reaction is finished to obtain the EDTA-SBA-15 adsorbent.
2. The method of claim 1, wherein NH is in step S1 2 The synthesis method of SBA-15 is as follows:
1g of SBA-15 which had been activated in advance at 120℃for 6 hours in vacuo was weighed, then dispersed in anhydrous toluene, 1mL of 3-aminopropyl triethoxysilane was added dropwise, and after mixing well, it was added in N 2 Reflux-reacting for 24h under atmosphere, filtering, washing with toluene and dichloromethane sequentially to remove unreacted 3-aminopropyl triethoxysilane, refluxing with a Soxhlet extractor with diethyl ether/dichloromethane at volume ratio of 1:1 overnight, vacuum-filtering, and vacuum-drying at 60deg.C to obtain NH 2 -SBA-15。
3. The method of claim 1, wherein the inert gas in step S2 is nitrogen.
4. The process of claim 1, wherein step S3 is performed sequentially with DCM, acetone, distilled water, and 0.1M NaHCO 3 The aqueous solution and distilled water were washed.
5. The process according to claim 1, wherein the vacuum drying in step S3 is carried out at a temperature of 45℃to 55 ℃.
6. An EDTA-SBA-15 adsorbent, characterized in that it is prepared by the method according to any one of claims 1 to 5.
7. The use of the EDTA-SBA-15 adsorbent according to claim 6, wherein said EDTA-SBA-15 adsorbent is used for Pb in water 2+ And (5) adsorbing.
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