CN116510695A - Collagen fiber/beta-cyclodextrin adsorbent and preparation method thereof - Google Patents
Collagen fiber/beta-cyclodextrin adsorbent and preparation method thereof Download PDFInfo
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- CN116510695A CN116510695A CN202310320848.1A CN202310320848A CN116510695A CN 116510695 A CN116510695 A CN 116510695A CN 202310320848 A CN202310320848 A CN 202310320848A CN 116510695 A CN116510695 A CN 116510695A
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- cyclodextrin
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- 102000008186 Collagen Human genes 0.000 title claims abstract description 59
- 108010035532 Collagen Proteins 0.000 title claims abstract description 59
- 229920001436 collagen Polymers 0.000 title claims abstract description 59
- 239000000835 fiber Substances 0.000 title claims abstract description 59
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 48
- 239000001116 FEMA 4028 Substances 0.000 title claims abstract description 48
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 48
- 235000011175 beta-cyclodextrine Nutrition 0.000 title claims abstract description 48
- 229960004853 betadex Drugs 0.000 title claims abstract description 48
- 239000003463 adsorbent Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 19
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004132 cross linking Methods 0.000 claims abstract description 5
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 abstract description 20
- 239000004098 Tetracycline Substances 0.000 abstract description 19
- 235000019364 tetracycline Nutrition 0.000 abstract description 19
- 229960002180 tetracycline Drugs 0.000 abstract description 18
- 229930101283 tetracycline Natural products 0.000 abstract description 18
- 150000003522 tetracyclines Chemical class 0.000 abstract description 9
- 125000000524 functional group Chemical group 0.000 abstract description 6
- 230000004048 modification Effects 0.000 abstract description 3
- 238000012986 modification Methods 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000002910 solid waste Substances 0.000 abstract description 2
- OFVLGDICTFRJMM-WESIUVDSSA-N tetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O OFVLGDICTFRJMM-WESIUVDSSA-N 0.000 description 10
- 229920001661 Chitosan Polymers 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003344 environmental pollutant Substances 0.000 description 6
- 231100000719 pollutant Toxicity 0.000 description 6
- 239000002957 persistent organic pollutant Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/286—Treatment of water, waste water, or sewage by sorption using natural organic sorbents or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a collagen fiber/beta-cyclodextrin adsorbent and a preparation method thereof, which uses glutaraldehyde as a cross-linking agent to combine-OH of beta-cyclodextrin with-NH on collagen fiber based on collagen fiber in a large amount of solid waste generated in the tanning process 2 The crosslinking modification is carried out to ensure that the beta-cyclodextrin can be stably combined on the collagen fiber, more functional groups and adsorption sites are added at the same time, the adsorption capacity to the tetracycline is enhanced, and the raw material collagen fiber and the beta-cyclodextrin have the characteristics of wide sources, low preparation cost and environmental friendliness, and the method disclosed by the invention has simple process and easy operation, and the prepared collagen fiber/beta-cyclodextrin adsorbent removes the tetracyclineThe rate reaches 98.21 percent, and has wide application prospect.
Description
Technical Field
The invention belongs to the technical field of adsorption materials, and particularly relates to a collagen fiber/beta-cyclodextrin adsorbent and a preparation method thereof.
Background
In recent years, with the rapid development of society, the demand for medicines and personal care products (Pharmaceutical and Personal Care Products, PPCPs) has greatly increased. Meanwhile, PPCPs are increasingly being discharged into the environment as a new type of pollutant. The PPCPs pollutants mainly comprise various antibiotics, medical drugs, bactericides and the like, have the characteristics of difficult degradation, various types, wide pollution range and the like, and finally can bring threat to human health and ecological environment through the enrichment effect of organisms. Among them, tetracycline (TC) has received extensive attention from researchers as a widely used antibiotic contaminant. At present, common methods for removing TC comprise a biodegradation method, an oxidation method, a photocatalysis method, an adsorption method and the like, wherein the adsorption method has the advantages of simple operation, good treatment effect, reusability and the like. Therefore, the novel adsorbent has wide application prospect in tetracycline wastewater treatment.
China is a large tanning country, and each 1t of raw leather is processed to generate 350kg of untanned solid waste which contains a large amount of collagen fibers. Collagen fibers are a material having a surface containing a large amount of-NH 2 The biomass resource containing oxygen functional groups such as-COOH, -OH and the like has a natural triple helix structure and has good hydrophilicity, so that the biomass resource can be used as a good adsorbent substrate material. The waste collagen fibers are applied to the adsorption of organic pollutants in the water body, so that the resource utilization of the waste collagen fibers can be realized. However, the adsorption of organic pollutants by the individual collagen fibers is weak, and the collagen fibers need to be modified.
The beta-cyclodextrin has hydrophilic surface and hydrophobic inside, and forms a hollow slightly conical cylinder stereo ring shape. The cavity has moderate inner diameter and strong inclusion capacity, and the raw materials are cheap and easy to prepare, so the method has been widely applied to the treatment of organic pollutants in water. However, beta-cyclodextrin is water-soluble, and is not easy to recover, and is usually used after being modified.
The prior art CN103691411A discloses a formaldehyde adsorbent containing chitosan and beta-cyclodextrin and a preparation method thereof, wherein the formaldehyde adsorbent containing chitosan and beta-cyclodextrin is prepared based on chitosan. However, chitosan is a deacetylated product of chitin, the types and the structures of surface functional groups are relatively simple, the stability of the chitosan is reduced along with the increase of the deacetylation degree, the adsorption effect is increased along with the increase of the deacetylation degree, meanwhile, as an adsorption material, the chitosan also has the defects of low density, low sedimentation speed, easy dissolution under acidic conditions and the like, and the steric hindrance of an adsorbent obtained by crosslinking the chitosan with beta-cyclodextrin is large, so that the effective contact area with organic pollutants is small, and the adsorption efficiency is low and is difficult to meet the adsorption requirement. The collagen fiber is obtained by directly crushing scraps, and the surface of the collagen fiber contains a large amount of oxygen-containing functional groups, so that the collagen fiber has a stable structure and is convenient to recycle. The collagen fiber has a natural triple helix structure, and beta-cyclodextrin is loaded on the surface of the collagen fiber, so that the adsorbent can be fully contacted with pollutants, and the adsorption performance is improved.
Disclosure of Invention
Aiming at the problems in the prior art, the beta-cyclodextrin is loaded on the collagen fibers to increase the number of adsorption sites and functional groups on the surfaces of the collagen fibers, so that the adsorption performance of tetracycline which is an organic pollutant in wastewater is enhanced, and the method has a good practical application prospect.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a method for preparing a collagen fiber/beta-cyclodextrin (CF-CD) adsorbent, comprising the steps of:
step 1) adding a cross-linking agent glutaraldehyde into the pretreated collagen fibers for cross-linking;
step 2) adding beta-cyclodextrin for further reaction;
and 3) washing and drying the reaction product to obtain the collagen fiber/beta-cyclodextrin material.
Further, the method for pretreating the collagen fibers in the step 1) is as follows: and immersing the collagen fiber in deionized water for 4-12 hours to obtain a collagen fiber mixed solution.
In step 1), glutaraldehyde solution with the mass fraction of 20-30% is slowly dripped, and the stirring reaction is continued for 3-5 h.
Further, the mass ratio of the collagen fiber to the beta-cyclodextrin in the step 2) is 1: (0.1-0.3).
Further, the step 3) comprises alternately washing the collagen fiber/beta-cyclodextrin material with deionized water and ethanol, and drying at 30-50 ℃.
The invention also discloses the collagen fiber/beta-cyclodextrin adsorbent prepared by adopting any one of the preparation methods.
Compared with the prior art, the invention has the advantages that:
1. the invention uses glutaraldehyde as a cross-linking agent to react with-NH on collagen fibers 2 and-OH of beta-cyclodextrin is subjected to crosslinking modification, so that the beta-cyclodextrin can be stably combined on collagen fibers, more functional groups and adsorption sites are added, the adsorption capacity to tetracycline is enhanced, and the removal rate of the tetracycline is up to 98.21%.
2. The raw materials of the collagen fiber and the beta-cyclodextrin have wide sources, low preparation cost, environmental friendliness and simple process, and are beneficial to practical application.
Drawings
The accompanying drawings, which are included to provide a further understanding of embodiments of the invention and are incorporated in and constitute a part of this application, illustrate embodiments of the invention. In the drawings:
FIG. 1 is a FT-IR diagram of Collagen Fibers (CF), beta-cyclodextrin (beta-CD) and the adsorbent of example 1 of the invention;
FIG. 2 is a graph showing the effect of adsorbing tetracycline by the adsorbents according to examples 1 to 3 of the present invention and collagen fibers;
Detailed Description
For better understanding of the technical scheme of the present invention, the technical scheme of the present invention will be further described with reference to the accompanying drawings and examples. The manner of carrying out the invention includes, but is not limited to, the following examples, which are intended to illustrate the invention, but are not intended to limit the scope thereof. The technical means used in the examples are conventional means well known to those skilled in the art unless otherwise indicated. The test methods in the following examples are conventional methods unless otherwise specified.
The "parts" used in the following specific examples are all "parts by mass".
Example 1: preparation of collagen fiber/beta-cyclodextrin adsorbent
10 parts of collagen fibers and 300 parts of deionized water were added to a three-necked flask and soaked for 8 hours. Then, 5 parts of 25% glutaraldehyde solution was slowly dropped into the three-necked flask, and the reaction was stirred at 35℃for 4 hours. Then 1 part of beta-cyclodextrin is taken and dissolved in 200 parts of deionized water, and the mixture is added into a three-necked flask to continue stirring reaction for 4 hours. And finally, repeatedly washing with deionized water, and drying at 40 ℃ to obtain the collagen fiber/beta-cyclodextrin adsorbent.
Referring to FIG. 1, FT-IR graphs of collagen fibers, beta-cyclodextrin and collagen fibers/beta-cyclodextrin prepared in example 1 of the present invention, 3412cm can be seen -1 The broad absorption band at this location is attributed to the stretching vibrational peaks of the O-H and N-H bonds. 2929cm -1 、1155cm -1 And 942cm -1 Characteristic peaks at the positions correspond to the stretching vibration peaks of C-H, C-O and alpha- (1, 4) glycosidic bonds on beta-CD respectively. 1663cm -1 And 1549cm -1 The stretching vibration peaks of the c=o and N-H bonds of CF, respectively. After the beta-CD is combined with the CF, the characteristic absorption peak with partial identical groups is covered by the CF, and the characteristic absorption peaks of the beta-CD and the CF are both shown in a spectrogram of the CF-CD, so that the beta-CD and the CF are successfully compounded.
Example 2: preparation of collagen fiber/beta-cyclodextrin adsorbent
10 parts of collagen fibers and 300 parts of deionized water were added to a three-necked flask and soaked for 8 hours. Then, 5 parts of 25% glutaraldehyde solution was slowly dropped into the three-necked flask, and the reaction was stirred at 35℃for 4 hours. Then 2 parts of beta-cyclodextrin is taken and dissolved in 200 parts of deionized water, and the mixture is added into a three-necked flask to continue stirring reaction for 4 hours. And finally, repeatedly washing with deionized water, and drying at 40 ℃ to obtain the collagen fiber/beta-cyclodextrin adsorbent.
Example 3: preparation of collagen fiber/beta-cyclodextrin adsorbent
10 parts of collagen fibers and 300 parts of deionized water were added to a three-necked flask and soaked for 8 hours. Then, 5 parts of 25% glutaraldehyde solution was slowly dropped into the three-necked flask, and the reaction was stirred at 35℃for 4 hours. And then 3 parts of beta-cyclodextrin is taken and dissolved in 200 parts of deionized water, and the mixture is added into a three-necked flask to continue stirring reaction for 4 hours. And finally, repeatedly washing with deionized water, and drying at 40 ℃ to obtain the collagen fiber/beta-cyclodextrin adsorbent.
Example 4: adsorption Performance test of adsorbents for Tetracyclines (TC)
The adsorbents prepared in examples 1 to 3 were represented by CF-CD-1, CF-CD-2 and CF-CD-3, respectively.
The activity test was performed on the collagen fibers and the CF-CD adsorbents prepared in examples 1 to 3, respectively, with the target pollutant being a tetracycline solution, under the following test conditions:
the adsorbent was weighed to an amount of 0.1g, added to 50mL of a TC solution having an initial concentration of 20mg/L, and subjected to vibration adsorption at 25℃for 2 hours at a rotation speed of 100 r/min. Samples were taken at regular intervals and filtered to obtain samples, and the concentration of TC in the samples was measured by uv-vis spectroscopy. Through C t /C 0 The effect of TC removal was determined, where C0 was the initial concentration of TC and Ct was the concentration of TC at reaction time t, as shown in FIG. 2.
As can be seen from FIG. 2, the removal rates of TC for collagen fibers, CF-CD-1, CF-CD-2 and CF-CD-3 were 30.01%, 97.82%, 98.21% and 97.95%, respectively. The beta-cyclodextrin is loaded on the collagen fiber, more functional groups and adsorption sites can be exposed, the adsorption performance of the material can be obviously improved by means of the action of electrostatic attraction and inclusion of pollutants, the TC is well removed, and the pollutant treatment capacity can be obviously improved.
In view of the foregoing, it should be appreciated that any combination of the various embodiments of the invention can be made without departing from the spirit of the invention; within the scope of the technical idea of the invention, any combination of various simple modifications and different embodiments of the technical proposal without departing from the inventive idea of the invention should be within the scope of the invention.
Claims (6)
1. A method for preparing a collagen fiber/beta-cyclodextrin adsorbent, which is characterized by comprising the following steps:
step 1) adding a cross-linking agent glutaraldehyde into the pretreated collagen fibers for cross-linking;
step 2) adding beta-cyclodextrin for further reaction;
and 3) washing and drying the reaction product to obtain the collagen fiber/beta-cyclodextrin material.
2. The method according to claim 1, wherein the method for pretreating the collagen fibers in step 1) comprises: and immersing the collagen fiber in deionized water for 4-12 hours to obtain a collagen fiber mixed solution.
3. The preparation method according to claim 1, wherein in the step 1), glutaraldehyde solution with the mass fraction of 20-30% is slowly added dropwise, and the stirring reaction is continued for 3-5 hours.
4. The method according to claim 1, wherein the mass ratio of the collagen fiber to the beta-cyclodextrin in the step 2) is 1: (0.1-0.3).
5. The method according to claim 1, wherein the step 3) comprises alternately washing the collagen fiber/beta-cyclodextrin material with deionized water and ethanol, and drying at 30-50 ℃.
6. A collagen fiber/beta-cyclodextrin adsorbent obtained by the production process according to any one of claims 1 to 5.
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