CN110102263A - Mercaptoethylmaine functional magnetic graphene oxide adsorbent and its preparation method and application - Google Patents
Mercaptoethylmaine functional magnetic graphene oxide adsorbent and its preparation method and application Download PDFInfo
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- CN110102263A CN110102263A CN201910283891.9A CN201910283891A CN110102263A CN 110102263 A CN110102263 A CN 110102263A CN 201910283891 A CN201910283891 A CN 201910283891A CN 110102263 A CN110102263 A CN 110102263A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
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- 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
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
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- 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
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- 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
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
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Abstract
Application the invention discloses a kind of mercaptoethylmaine functional magnetic graphene oxide adsorbent and preparation method thereof and in tetracycline adsorbing separation.Particular by by Fe3O4After magnetic nano-particle and graphene oxide are compound, mercaptoethylmaine is recycled to be modified to obtain to graphene oxide.The adsorbent had not only had the high characterization of adsorption of graphene oxide, but also the easily separated characteristic with magnetic material, has quick Magneto separate ability and higher adsorption capacity for the tetracycline in aqueous solution, has certain practical value.
Description
Technical field
The invention belongs to Magnetic solid phases abstraction technique fields, and in particular to a kind of magnetic oxygen using mercaptoethylmaine functionalization
Graphite alkene adsorbent and preparation method thereof and the application in tetracycline adsorbing separation.
Background technique
Drug and personal-care supplies (PPCPs) are a kind of important emerging pollutants for causing people's extensive concern.PPCPs
Including various human pharmaceutical use compounds and veterinary drug, wherein antibiotic oneself be considered a type of important emerging pollutant, cause state
The extensive concern of border society.The abuse of antibiotic can not only affect human health, and antibiotic present in environment is aobvious
Various serious environmental effects are shown, such as the generation of antiviral antibiotic gene in microbial body.Tetracycline antibiotics are a kind of wide
Antibiotic is composed, most representative is tetracycline.Tetracycline medication is also commonly used for that antibacterial is somatotrophic to be added in addition to being used as treatment
Add agent to be added in animal feed, tetracycline medication is caused to remain in animal body.The intake of long-term low dose has very much can
It can generate various chronic and savings property toxicity and drug resistance problems.Tetracycline medication can inhibit the development of child's tooth and bone
Growth, after these antibacterials remained in aquatic livestock property product enter human body, sensitive individual will sensitization, generate anti-
Body will cause allergic reaction etc. then when these are contacted again these drugs by the individual of sensitization.Therefore, exploitation is to residual
Staying antibiotic, accurately and rapidly analysis method is to study the necessary means of its environmental behaviour and ecological effect.
Currently, various analytical technology detection antibiotic residues, such as microbial method, thin-layer chromatography have had been established both at home and abroad
Method, liquid chromatography, enzyme-linked immunization etc..However, environmental sample and biological specimen ingredient are complicated and antibacterial medicine residue is big
All in trace level, directly there are certain difficulties for measurement.Therefore foundation is scientific, quickly and effectively analysis method is current
The a great problem that analysis worker faces.In the analytic process of trace materials, determinand is before carrying out instrument analysis, before sample
Processing is a vital link.
Magnetic solid phases abstraction technique (magnetic solid-phase extraction, MSPE) is with magnetic nano particle
Son is used as adsorbent, wherein Fe3O4As a kind of magnetic nanometer particle, preparation is convenient, has no toxic and side effect to human body, and has preferable
The features such as biocompatibility and biological degradability is to study one of widest magnetic nano material at present.Graphene oxide has
Biggish specific surface area, meanwhile, graphene oxide layer structure centre includes great amount of hydroxy group and epoxy group, and layer side edge contains greatly
The carboxyl of amount is conducive to carry out modification to it, and therefore, graphene oxide has become the research hotspot of water process.But oxygen
Graphite alkene partial size is smaller, when ambient pressure is big may with flow through solid-phase extraction column solution flow out cylinder, and pressure compared with
Hour disengaging time is long.Therefore, the graphite oxide alkenes adsorbent of appropriate particle size is prepared, optimization separation process is to must overcome
One of critical issue.
Summary of the invention
The technical issues of solution: the present invention is directed to the deficiency of existing tetracycline adsorption separation technology, as adsorbent is fabricated to
The technical problems such as this height, detection means complexity and adsorption effect difference, by Fe3O4The segregative advantage of magnetic nano-particle is received with carbon
Rice material combines, and provides a kind of magnetic oxygenated graphene adsorbent using mercaptoethylmaine functionalization, which both had
The high characterization of adsorption of nano material, and the easily separated characteristic with magnetic material have the tetracycline in aqueous solution quick
Magneto separate ability and higher adsorption capacity have certain practical value.
Technical solution:
A kind of mercaptoethylmaine functional magnetic graphene oxide adsorbent, is by Fe3O4Magnetic nano-particle and graphite oxide
After alkene is compound, then mercaptoethylmaine is carried out to graphene oxide and modifies to obtain.
The preparation method of above-mentioned mercaptoethylmaine functional magnetic graphene oxide adsorbent, comprising the following steps:
Step 1, graphene oxide is dispersed in water, ultrasound obtains graphene oxide dispersion；
Step 2, graphene oxide dispersion is heated to 70-90 DEG C, under the conditions of nitrogen protection, FeCl is added3·6H2O
And FeCl2·4H2O, stirring adjust pH value of solution to 10-11,70-90 DEG C of insulation reaction 05-1.5h, and water and second are successively used in filtering
Alcohol washing, vacuum drying obtain magnetic oxygenated graphene；
Step 3, by magnetic oxygenated graphene dispersion in dehydrated alcohol, ultrasound, be added under stirring condition mercaptoethylmaine and
Dicyclohexylcarbodiimide, nitrogen protection are protected from light 24-36h, filter, vacuum drying, obtain functional graphene oxide suction
Attached dose.
Further, ultrasound condition is 20-25 DEG C, 2-3h in step 1.
Further, FeCl is added to graphene oxide solution in step 23·6H2O and FeCl2·4H2O, FeCl3·
6H2O and FeCl2·4H2The mass ratio of O is 2.7, stirs 10-30min.
Further, it is 60-80 DEG C, 24-36h that condition is dried in vacuo in step 2.
Further, ultrasound condition is 20-25 DEG C, 1-2h in step 3.
Further, in step 3 magnetic oxygenated graphene be added, the mass ratio of mercaptoethylmaine and dicyclohexylcarbodiimide
For 1:1:2.5.Further, it is 60-80 DEG C, 24-36h that condition is dried in vacuo in step 3.
Application of the above-mentioned mercaptoethylmaine functional magnetic graphene oxide adsorbent in tetracycline adsorbing separation.
Further, above-mentioned application is specifically and the functional graphene oxide adsorbent is directly appended to containing Fourth Ring
In the sample solution of element, after Static Adsorption, by externally-applied magnetic field separating adsorbent, the adsorbing separation to tetracycline can be completed.
The utility model has the advantages that
1, the present invention combines the advantages of magnetic nano material and graphene oxide, and avoiding conventional solid extraction adsorbent needs to fill
The troublesome operations such as column and sample loading solve time-consuming, column blockage problem.
2, the magnetic oxygenated grapheme material of functionalization is prepared, and is used for the adsorbing separation of tetracycline, to four
The large amount of adsorption of ring element, up to 56.8mg/g.
2, the magnetic oxygenated grapheme material AET-GO-Fe of functionalization is prepared3O4It is directly appended in sample solution,
Magnetic adsorbent is separated by externally-applied magnetic field after the completion of absorption, there is quick Magneto separate ability.
Detailed description of the invention
Fig. 1 is AET-GO-Fe in embodiment 13O4The infrared spectrogram of adsorbent.
Fig. 2 is AET-GO-Fe in embodiment 23O4Staticadsorption experiment schematic diagram of the adsorbent to tetracycline.
Fig. 3 is AET-GO-Fe in embodiment 33O4Adsorbent is under different acidity to the adsorption effect curve graph of tetracycline.
Fig. 4 is the AET-GO-Fe of different quality in embodiment 43O4Adsorption effect curve graph of the adsorbent to tetracycline.
Fig. 5 is AET-GO-Fe in embodiment 43O4Adsorbent is in different adsorption times to the adsorption effect of tetracycline.
Fig. 6 is AET-GO-Fe in embodiment 63O4Linear model of the adsorbent to tetracycline Langmuir adsorption isotherm
Figure.
Specific embodiment
The present invention is described in further details below with reference to specific embodiment, to better understand the present invention.It answers
Work as understanding, described herein specific examples are only used to explain the present invention, is not intended to limit the present invention.
Embodiment 1
Mercaptoethylmaine functional magnetic graphene oxide adsorbent (AET-GO-Fe3O4) preparation, the preparation method is as follows:
Step 1, the preparation of graphene oxide dispersion: taking 0.2g graphite oxide to be scattered in 200mL water, room temperature ultrasound
2h obtains graphene oxide dispersion (concentration 1mg/L).
Step 2, the preparation of magnetic oxygenated graphene: graphene oxide dispersion is stirred and is heated up under the conditions of nitrogen protection
To 80 DEG C, 1.9g FeCl is added3·6H2O and 0.7g FeCl2·4H2O stirs 15min, is uniformly dispersed.Then it is added 28%
Ammonium hydroxide about 10mL adjusts pH value of solution=10,80 DEG C and reacts 1h, and filtering is successively washed with water and ethanol washing, 70 DEG C of vacuum drying
12h obtains the magnetic oxygenated graphene (GO-Fe of solid product3O4)。
Step 3, the preparation of the magnetic oxygenated graphene adsorbent of mercaptoethylmaine functionalization: the magnetic oxygenated graphite of 0.4g is taken
Alkene is scattered in 100mL dehydrated alcohol, room temperature ultrasound 1h.It is stirred at room temperature down, 0.4g mercaptoethylmaine and 1.0g dicyclohexyl is added
Carbodiimide, nitrogen protection are protected from light for 24 hours.Product filters, in a vacuum drying oven for 24 hours in 60 DEG C of dryings, obtained solid
The magnetic oxygenated graphene adsorbent (AET-GO-Fe of product mercaptoethylmaine functionalization3O4)。
IR analysis: the infrared spectroscopy of the magnetic oxygenated graphene adsorbent of mercaptoethylmaine functionalization is as shown in Figure 1, GO curve
In 3600~2800cm-1Place is the stretching vibration peak of O-H group；1700cm-1The absorption peak at place is C=O stretching vibration peak.Magnetic
The infrared spectrum of property graphene oxide is in 580cm-1There is new absorption peak in place, belongs to Fe-O stretching vibration peak.Sulfydryl second
The infrared spectrum of the magnetic oxygenated graphite of amino-functionalization is in~3400cm-1With~1650cm-1There is absorption peak at place, show to have-
CONHR exists；~2900cm-1Locate peak and derives from-CH2Stretching vibration；~580cm-1Locate the stretching vibration that peak derives from Fe-O.
By carrying out IR Characterization to the composite material of synthesis, it was demonstrated that successfully synthesize the magnetic oxygenated graphite of mercaptoethylmaine functionalization
Alkene.
Embodiment 2
Staticadsorption experiment
A series of various concentration tetracycline standard solution (5,10,15,20,25,30mg/L) are prepared, are successively surveyed in 356nm
The absorbance A of each part sample is obtained, tetracycline standard curve is drawn.
In order to probe into AET-GO-Fe3O4Adsorbent is used for the absorption property of tetracycline adsorption, in conjunction with Staticadsorption experiment pair
Optimal adsorption experiment condition is investigated, and Staticadsorption experiment is as shown in Fig. 2, adsorption efficiency is calculated with formula (1):
Adsorption efficiency (%)=(c0-ce)/c0× 100% (1)
Wherein, c0And ceWhen respectively initial and balance when sample solution in tetracycline concentration.
Embodiment 3
AET-GO-Fe3O4Adsorbent is under different acidity to the adsorption effect of tetracycline
By 20mg AET-GO-Fe3O4Adsorbent be added to it is a series of containing 10mL tetracycline standard solution (20mg/L,
PH=3.0-12.0 in), 1h is vibrated after being sufficiently mixed uniformly.After separation, supernatant is taken to measure the absorbance A of each part sample,
And calculate the adsorption rate of each part sample.Experimental result is as shown in figure 3, when the pH of solution is when 4.0-10.0, adsorbent pair
Tetracycline shows high adsorption rate, reaches Absorption quantity (> 95%).
Embodiment 4
The AET-GO-Fe of different quality3O4Adsorption effect of the adsorbent to tetracycline
Prepare pH 4.0 20mg/L tetracycline standard solution, respectively into every centrifuge tube be added different quality (5,
10,15,20,25,30,35mg) AET-GO-Fe3O4, then the standard solution 10mL of preparation is added in each centrifuge tube, to abundant
1h is vibrated after mixing.After separation, the absorbance A of each part sample is measured, experimental result is as shown in figure 4, work as the matter of adsorbent
When amount is between 10-35mg, the Absorption quantity to tetracycline can be completed.
Embodiment 5
AET-GO-Fe3O4Adsorbent is in different adsorption times to the adsorption effect of tetracycline
The tetracycline standard solution for preparing the 20mg/L of pH 4.0 a series of, contains 10mL standard solution to every respectively
15mg AET-GO-Fe is added in centrifuge tube3O4, 5,10,15,20,25,30 and 35min is vibrated respectively after being sufficiently mixed uniformly.
After separation, the absorbance A of each part sample is measured, and calculates the adsorption rate of each part sample.Experimental result is as shown in figure 5, in 15min
It inside can reach Absorption quantity, illustrate that adsorption process can quickly reach dynamic absorption balance, and quickly kinetic balance is said
This bright adsorbent is known as good affinity to Fourth Ring.
Embodiment 6
AET-GO-Fe3O4Maximum adsorption capacity of the adsorbent to tetracycline
It prepares a series of different tetracycline standard solution of concentration (10,20,30,40,50,60,80,100mg/L), respectively
Take 10mL in containing 15mg AET-GO-Fe3O4Centrifuge tube in, it is to be mixed uniformly after oscillation 2h make to reach adsorption equilibrium.Separation
Afterwards, the absorbance A of each part sample is measured.Equilibrium adsorption capacities (qe, mg/g) calculation method such as formula (2) shown in:
In formula, c0And ceThe concentration (mg/L) of solution when respectively initial and reaching adsorption equilibrium；M is the matter of adsorbent
It measures (g)；V is the volume of solution, unit mL.
In order to assess the potential maximum adsorption capacity of adsorbent, with Langmuir adsorption isotherm to the data that measure of experiment
It is handled, shown in calculating process such as formula (3):
With ceFor independent variable, ce/qeFor variable, as shown in fig. 6, straight line is obtained, slope 1/q, intercept 1/
qb.AET-GO-Fe is obtained by calculation3O4Maximum adsorption capacity q to tetracycline in solution is 56.8mg/g.
Claims (10)
1. a kind of mercaptoethylmaine functional magnetic graphene oxide adsorbent, it is characterised in that: by Fe3O4Magnetic nano-particle with
After graphene oxide is compound, mercaptoethylmaine is recycled to be modified to obtain to graphene oxide.
2. the preparation method of mercaptoethylmaine functional magnetic graphene oxide adsorbent described in claim 1, it is characterised in that:
The following steps are included:
Step 1, graphene oxide is dispersed in water, ultrasound obtains graphene oxide dispersion；
Step 2, graphene oxide dispersion is heated to 70-90 DEG C, under the conditions of nitrogen protection, FeCl is added3•6H2O and
FeCl2•4H2O, stirring adjust pH value of solution to 10-11,70-90 DEG C of insulation reaction 05-1.5h, and filtering is successively washed with water and ethyl alcohol
It washs, is dried in vacuo, obtains magnetic oxygenated graphene；
Step 3, ultrasonic by magnetic oxygenated graphene dispersion in dehydrated alcohol, mercaptoethylmaine and two rings are added under stirring condition
Hexyl carbodiimide, nitrogen protection are protected from light 24-36h, filter, and vacuum drying obtains functional graphene oxide adsorbent.
3. preparation method according to claim 2, it is characterised in that: ultrasound condition is 20-25 DEG C, 2-3h in step 1.
4. preparation method according to claim 2, it is characterised in that: the FeCl being added in step 23·6H2O and FeCl2·4H2O
Mass ratio is 2.7, and mixing time is 10-30 min.
5. preparation method according to claim 2, it is characterised in that: the condition that is dried in vacuo in step 2 is 60-80 DEG C, 24-36h.
6. preparation method according to claim 2, it is characterised in that: ultrasound condition is 20-25 DEG C, 1-2h in step 3.
7. preparation method according to claim 2, it is characterised in that: magnetic oxygenated graphene, mercaptoethylmaine and two rings in step 3
The mass ratio of hexyl carbodiimide is 1:1:2.5.
8. preparation method according to claim 2, it is characterised in that: the condition that is dried in vacuo in step 3 is 60-80 DEG C, 24-36h.
9. mercaptoethylmaine functional magnetic graphene oxide adsorbent answering in tetracycline adsorbing separation described in claim 1
With.
10. application according to claim 9, it is characterised in that: be specifically by the functional graphene oxide adsorbent
It is directly appended in the sample solution containing tetracycline, after Static Adsorption, by externally-applied magnetic field separating adsorbent, can be completed pair
The adsorbing separation of tetracycline.
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Cited By (2)
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| CN110665486A (en) * | 2019-10-17 | 2020-01-10 | 福州大学 | Magnetic ferroferric oxide-PAMAM-antibody complex and preparation method and application thereof |
| WO2023123142A1 (en) * | 2021-12-29 | 2023-07-06 | 北京建工环境修复股份有限公司 | Surface plasma resonance sensing chip, and preparation method therefor and use thereof |
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Application publication date: 20190809 |