CN104645938A - Preparation method of dye functional magnetic nano material and application in fluorescent sensing and magnetic separation of TNT - Google Patents

Preparation method of dye functional magnetic nano material and application in fluorescent sensing and magnetic separation of TNT Download PDF

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CN104645938A
CN104645938A CN201510073819.5A CN201510073819A CN104645938A CN 104645938 A CN104645938 A CN 104645938A CN 201510073819 A CN201510073819 A CN 201510073819A CN 104645938 A CN104645938 A CN 104645938A
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nano material
tnt
phosphoric acid
magnetic nano
dyefunctionalized
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CN104645938B (en
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邹文生
王亚琴
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Zhongke Rinland Environmental Protection Technology Beijing Co ltd
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Anhui Jianzhu University
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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
    • 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
    • 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
    • B01J20/28009—Magnetic properties
    • 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
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/34—Regenerating or reactivating
    • B01J20/345—Regenerating or reactivating using a particular desorbing compound or mixture
    • B01J20/3475—Regenerating or reactivating using a particular desorbing compound or mixture in the liquid phase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material

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Abstract

The invention discloses a preparation method of a dye functional magnetic nano material and application in fluorescent sensing and magnetic separation of TNT. The preparation method comprises the following steps of firstly, reacting a ferric oleate complex with oleylamine in oleic acid so as to obtain an oleic acid coated ferroferric oxide nano material; then dispersing the oleic acid coated ferroferric oxide nano material into a diethyl ether solution of 2-ethylamine phosphate to complete ligand exchange so as to obtain a 2-ethylamine phosphate coated ferroferric oxide nano material; and finally reacting with fluorescein isocyanate so as to obtain a target product. The dye functional magnetic nano material can be used for sensing and removing the trace TNT in a polluted water sample, and has the reproducibility.

Description

A kind of preparation method of dyefunctionalized magnetic Nano material and the application of fluorescence sense and Magneto separate TNT thereof
Technical field
The invention belongs to technical field of nanometer material preparation, relate to the preparation method of the nano material of a kind of renewable fluorescence sense and the high quick-fried thing of Magneto separate TNT.
Background technology
Due to the biopersistence of TNT, toxicity and mutagenicity, the pollution of TNT to soil, air and underground water becomes a public topic.Report shows: human or animal, after being exposed in TNT atmosphere for a long time, will produce major injury to nervous system, kidney, liver and other tissue; In addition, it also has that other toxic and side effect comprises leukocytosis, peripheral neuritis, heart are lost a war and tumor of bladder etc.Therefore, develop highly sensitive method and seem particularly important with selective sensing and removal TNT.
At present, the high-sensitive method for sensing of development is mainly focused on to the analysis of TNT, understands the concrete concentration of the TNT in TNT contaminant water; Or development enrichment material, removes the TNT in contaminated samples.Wherein, FRET or Charger transfer method for quenching can in sensing sample TNT to subnanomole level.And TNT enrichment material mainly comprises nano material and molecularly imprinted polymer etc.Nano material is comparatively large because of its specific surface, has very strong adsorption capacity, but its absorption is not selective and adsorption capacity is less; TNT imprinted polymer has good selective adsorption capacity to TNT, but most " trace cave " is positioned at polymeric inner, and mass transfer ability is weak, and the preparation of imprinted polymer is more restive, which has limited the range of application of the method.Therefore, how can realize the sensing for TNT in contaminant water and enrichment simply, at low cost, remain a great problem of the preparing technical field of function nano material.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of dyefunctionalized magnetic Nano material and the application in fluorescence sense and Magneto separate TNT thereof;
Another object of the present invention realizes the regeneration of dyefunctionalized magnetic Nano material after fluorescence sense and Magneto separate TNT.
Technical solution problem of the present invention, adopts following technical scheme:
The preparation method of the dyefunctionalized magnetic Nano material of the present invention, its feature is to carry out as follows:
(1) take rub iron oleate complex and 20 ~ 40 milliliters of oleyl amines of 3 ~ 6 millis to join in flask, then add 5 ~ 15 milliliters of oleic acid and be heated to 120 DEG C, be stirred to the dissolving of iron oleate complex, obtain mixed solution;
(2) described mixed solution is warmed up to 200 DEG C, fills nitrogen dehydration and constant temperature after 2 hours, continue to be warmed up to 300 ~ 320 DEG C, and constant temperature 2 hours;
(3) naturally cool to room temperature, filter to obtain sediment, then use deionized water and absolute ethanol washing gained sediment successively;
(4) sediment is placed in vacuum drying chamber with the temperature of 40 ~ 60 DEG C drying 6 hours, obtains the ferriferrous oxide nanometer material of Coated with Oleic Acid;
(5) 2-phosphoric acid ethylamine is obtained in absolute ether the diethyl ether solution that mass concentration is the 2-phosphoric acid ethamine of 4 ~ 5%, the ferriferrous oxide nanometer material of described Coated with Oleic Acid is dispersed in the diethyl ether solution of described 2-phosphoric acid ethamine, ligand exchange is completed under ultrasonic, then by Magneto separate, the ferriferrous oxide nanometer material that 2-phosphoric acid ethamine is coated is obtained;
(6) fluorescein isocyanate is dissolved in absolute ethyl alcohol the ethanolic solution obtaining fluorescein isocyanate; Ferriferrous oxide nanometer material coated for described 2-phosphoric acid ethamine is dispersed in absolute ethyl alcohol, dropwise add the ethanolic solution of described fluorescein isocyanate again, mechanical agitation 12 hours under room temperature under nitrogen, then be separated by magnet, after gained solid product uses deionized water and absolute ethanol washing successively, obtain dyefunctionalized magnetic Nano material;
The mass ratio of the ferriferrous oxide nanometer material that described 2-phosphoric acid ethamine is coated and described fluorescein isocyanate is 100:1.
The iron oleate complex that above-mentioned preparation method uses can prepare as follows:
By FeCl 36H 2o and enuatrol are that iron oleate complex prepared by raw material.Simply, by 5.4 grams of FeCl 36H 2o and 18.25g enuatrol is dissolved in the mixed solution that 40 milliliters of ethanol, 30 milliliters of redistilled waters and 70 milliliters of hexanes form, solution be heated to 70 DEG C and keep 4 hours, after reaction terminates, by the organic layer second distillation water washing 3 times containing oleic acid iron complex, then after being steamed by hexane, namely obtain wax-like iron oleate complex.
Dyefunctionalized magnetic Nano material pattern prepared by the present invention is spherical, and structure is homogeneous, single dispersing, diameter about 8 ~ 10 nanometer, has super magnetic property and the fluorescent dye that can be coupled.
Dyefunctionalized magnetic Nano material prepared by said method can be used for fluorescence sense and Magneto separate TNT.Because upper three nitros of TNT are strong electron-withdrawing group groups, make the phenyl ring of TNT positively charged relative to short of electricity, the phenyl ring of TNT short of electricity easily with containing lone electron pair molecule forms Meisenheimer complex as Acid-Base pairing effect occurs amine etc., and the absworption peak of this complex is positioned at 516 ran.In use, be dispersed in the aqueous solution containing TNT using dyefunctionalized magnetic Nano material as probe, TNT is combined in nanometer Fe by the formation of Meisenheimer complex 3o 4surface, by the fluorescence of FRET mode quench fluorescence element, thus reach the object of TNT sensing; Due to nanometer Fe 3o 4magnetic response characteristic, under additional magnetic fields, nanometer Fe can be combined in by with the form of Meisenheimer complex 3o 4on TNT be separated from solution; The combination of TNT and amine-containing compound is a kind of reversible action, will combine the Fe of TNT 3o 4nanoparticle dispersion is at height containing in amine aqueous solution, and TNT will transfer in solution, make Fe 3o 4nano particle is regenerated.
After the fluorescence sense completing TNT at dyefunctionalized magnetic Nano material of the present invention and Magneto separate, to the nano material Magneto separate of TNT have been adsorbed out under outside magnetic field effect, then being immersed in concentration is in the aqueous solution of the ethylenediamine of 1.0M 12 hours, Magneto separate also uses second distillation water washing again, the fluorescence of dyefunctionalized magnetic Nano material and enrichment performance are restored, realize its regeneration.
Compared with existing TNT sensing or enrichment material, the present invention has following feature and advantage:
1, dyefunctionalized magnetic Nano material of the present invention can trace TNT in sensing pollution water sample: magnetic Nano material rich surface amino-contained of the present invention, amido can be combined by Acid-Base pairing effect with TNT, the ultraviolet-ray visible absorbing of the complex formed is positioned at 516 nanometers, almost overlapping with transmitting 519 nanometer of fluorescein, thus by being low to moderate the TNT of 50 nanometers in FRET mode sensing water sample.
2, dyefunctionalized magnetic Nano material of the present invention can enrichment remove TNT in water: due to the Acid-Base pairing effect between the amido of nano material of the present invention and TNT, in water sample, TNT is easy to the surface being combined in magnetic nano-particle, by the effect of externally-applied magnetic field, TNT can be made to separate from water sample.
3, dyefunctionalized magnetic Nano material of the present invention has recyclability: to be immersed in the aqueous solution containing 1.0M ethylenediamine 12 hours, Magneto separate after intermediate water repeatedly washs, fluorescence and the enrichment performance of magnetic nano-particle are restored.
The reagent used in the preparation process of 4, dyefunctionalized magnetic Nano material of the present invention is common agents, and cost is low, and reaction condition is easy to realize, and renovation process is convenient.
Accompanying drawing explanation
Fig. 1 is the phenogram of the dyefunctionalized magnetic Nano material of embodiment 1 gained, and wherein left figure is the TEM figure of material, and centre is the XRD figure of material, and right figure is the magnetization curve of material;
Fig. 2 be the dyefunctionalized magnetic Nano material of embodiment 1 gained for fluorescence sense, wherein left figure is TNT dependence fluorescence spectrum, the fluorescence intensity that right figure is TNT concentration when being 1 μm of ol;
Fig. 3 is the test of the dyefunctionalized magnetic Nano material reproducibility of embodiment 1 gained, and after 5 take turns experiment, fluorescence intensity almost remains unchanged.
Detailed description of the invention
Below by way of specific embodiment, description detailed complete is further done to technical scheme of the present invention.Following embodiment further illustrates of the present invention, and do not limit the scope of the invention.
Embodiment 1:
The present embodiment prepares dyefunctionalized magnetic Nano material as follows:
(1) take iron oleate complex 4.0 milli to rub with the flask of oleyl amine 20 milliliters to 100 milliliters, add 6 milliliters of oleic acid and be heated to 120 DEG C, be stirred to iron oleate complex and dissolve, obtain mixed solution;
(2) mixed solution is warmed up to 200 DEG C, fills nitrogen and dewater and after keeping 2 hours, solution continued be warmed up to 300 DEG C, and keep 2 hours;
(3) naturally cool to room temperature, filter to obtain sediment, then use deionized water and absolute ethanol washing 3 ~ 5 times successively;
(4) sediment is placed in vacuum drying chamber with the temperature of 50 DEG C drying 6 hours, obtains the ferriferrous oxide nanometer material of Coated with Oleic Acid;
(5) 2-phosphoric acid ethylamine is obtained in absolute ether the diethyl ether solution that mass concentration is the 2-phosphoric acid ethamine of 5%, the ferriferrous oxide nanometer material of Coated with Oleic Acid is dispersed in the diethyl ether solution of 2-phosphoric acid ethamine, ligand exchange is completed under ultrasonic, then by Magneto separate, the ferriferrous oxide nanometer material that 2-phosphoric acid ethamine is coated is obtained.
(6) 1.0 milligrams of fluorescein isocyanate are dissolved in absolute ethyl alcohol the ethanolic solution obtaining fluorescein isocyanate; Ferriferrous oxide nanometer material coated for 100 milligrams of 2-phosphoric acid ethamine is dispersed in absolute ethyl alcohol, dropwise add the ethanolic solution of fluorescein isocyanate again, mechanical agitation 12 hours under room temperature under nitrogen, then be separated by magnet, gained solid product uses deionized water and absolute ethanol washing 3 ~ 5 times successively, obtains dyefunctionalized magnetic Nano material;
Fig. 1 is the phenogram of the dyefunctionalized magnetic Nano material of the present embodiment gained, and wherein left figure is the TEM figure of material, and centre is the XRD figure of material, and right figure is the magnetization curve of material.Fe can be found out from left figure 3o 4the Size Distribution of nano particle is relatively more even, and diameter is 8 ran.Middle figure XRD shows Fe 3o 4nano particle is magnetic iron ore crystallographic system.Right figure shows Fe 3o 4nano particle does not have hysteresis loop, has super magnetic characteristic.
For the dyefunctionalized magnetic Nano material of test the present embodiment gained is used for the performance of fluorescence sense and Magneto separate TNT, do following experiment: pipetting about 3 ml concns is that the dyefunctionalized magnetic Nano material solution of 1 mg/ml is in cuvette, measure its fluorescence intensity, then in solution, constantly drip ethanolic solution 10 microlitre of the TNT that to rub containing 10 millis, micro-ly to rub until the TNT concentration in cuvette reaches 1, measure fluorescence intensity one by one.By the Fe in cuvette 3o 4nano particle, after external magnetic field is separated, measures the TNT solubility before and after being separated with UV-VIS spectrophotometry, the separating effect of assessment TNT.
Figure 2 shows that the TNT dependence fluorescence spectrum (left side) of the dyefunctionalized magnetic Nano material of the present embodiment; 1.0 micro-TNT rubbed result in the fluorescent quenching (right side) of probe.Assessed by ultraviolet-visible spectrum, 1.0 micro-TNT of rubbing are attached to Fe 3o 4on ratio be about 14%, namely also this part TNT can remove from solution.
For the reproducibility of the test dyefunctionalized magnetic Nano material of the present embodiment gained after completing fluorescence sense and Magneto separate TNT, do to test as follows: by the volume expansion of above-mentioned experiment to 50 milliliters, by the Fe be separated 3o 4nano particle to be immersed in the aqueous solution containing 1.0M ethylenediamine 12 hours, and Magneto separate also, after redistilled water repeatedly washs, assesses fluorescence and the enrichment performance of dyefunctionalized magnetic Nano material.
As shown in Figure 3, as can be seen from the figure after 5 take turns experiment, fluorescence intensity change remains in 5% scope result, proves that the dyefunctionalized magnetic Nano material of the present embodiment has good reproducibility.
Embodiment 2:
(1) take iron oleate complex 6 milli to rub with the flask of oleyl amine 40 milliliters to 100 milliliters, add 15 milliliters of oleic acid and be heated to 120 DEG C, be stirred to iron oleate complex and dissolve, obtain mixed solution;
(2) mixed solution is warmed up to 200 DEG C, fills nitrogen and dewater and after keeping 2 hours, solution continued be warmed up to 320 DEG C, and keep 2 hours;
(3) naturally cool to room temperature, filter to obtain sediment, then use deionized water and absolute ethanol washing 3 ~ 5 times successively;
(4) sediment is placed in vacuum drying chamber with the temperature of 60 DEG C drying 6 hours, obtains the ferriferrous oxide nanometer material of Coated with Oleic Acid;
(5) 2-phosphoric acid ethylamine is obtained in absolute ether the diethyl ether solution that mass concentration is the 2-phosphoric acid ethamine of 4%, the ferriferrous oxide nanometer material of Coated with Oleic Acid is dispersed in the diethyl ether solution of 2-phosphoric acid ethamine, ligand exchange is completed under ultrasonic, then by Magneto separate, the ferriferrous oxide nanometer material that 2-phosphoric acid ethamine is coated is obtained.
(6) 1.0 milligrams of fluorescein isocyanate are dissolved in absolute ethyl alcohol the ethanolic solution obtaining fluorescein isocyanate; Ferriferrous oxide nanometer material coated for 100 milligrams of 2-phosphoric acid ethamine is dispersed in absolute ethyl alcohol, dropwise add the ethanolic solution of fluorescein isocyanate again, mechanical agitation 12 hours under room temperature under nitrogen, then be separated by magnet, gained solid product uses deionized water and absolute ethanol washing 3 ~ 5 times successively, obtains dyefunctionalized magnetic Nano material.

Claims (2)

1. a preparation method for dyefunctionalized magnetic Nano material, is characterized in that carrying out as follows:
(1) take rub iron oleate complex and 20 ~ 40 milliliters of oleyl amines of 3 ~ 6 millis to join in flask, then add 5 ~ 15 milliliters of oleic acid and be heated to 120 DEG C, be stirred to the dissolving of iron oleate complex, obtain mixed solution;
(2) described mixed solution is warmed up to 200 DEG C, fills nitrogen dehydration and constant temperature after 2 hours, continue to be warmed up to 300 ~ 320 DEG C, and constant temperature 2 hours;
(3) naturally cool to room temperature, filter to obtain sediment, then use deionized water and absolute ethanol washing gained sediment successively;
(4) sediment is placed in vacuum drying chamber with the temperature of 40 ~ 60 DEG C drying 6 hours, obtains the ferriferrous oxide nanometer material of Coated with Oleic Acid;
(5) 2-phosphoric acid ethylamine is obtained in absolute ether the diethyl ether solution that mass concentration is the 2-phosphoric acid ethamine of 4 ~ 5%, the ferriferrous oxide nanometer material of described Coated with Oleic Acid is dispersed in the diethyl ether solution of described 2-phosphoric acid ethamine, ligand exchange is completed under ultrasonic, then by Magneto separate, the ferriferrous oxide nanometer material that 2-phosphoric acid ethamine is coated is obtained;
(6) fluorescein isocyanate is dissolved in absolute ethyl alcohol the ethanolic solution obtaining fluorescein isocyanate; Ferriferrous oxide nanometer material coated for described 2-phosphoric acid ethamine is dispersed in absolute ethyl alcohol, dropwise add the ethanolic solution of described fluorescein isocyanate again, mechanical agitation 12 hours under room temperature under nitrogen, then be separated by magnet, after gained solid product uses deionized water and absolute ethanol washing successively, obtain dyefunctionalized magnetic Nano material;
The mass ratio of the ferriferrous oxide nanometer material that described 2-phosphoric acid ethamine is coated and described fluorescein isocyanate is 100:1.
2. an application for the dyefunctionalized magnetic Nano material prepared by method according to claim 1, be is characterized in that: for fluorescence sense and Magneto separate TNT.
CN201510073819.5A 2015-02-11 2015-02-11 A kind of preparation method of dyefunctionalized magnetic Nano material and its application of fluorescence sense and Magneto separate TNT Active CN104645938B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105363394A (en) * 2015-09-24 2016-03-02 济南大学 Preparation and application of magnetic fluorescent molecule imprinting nano-microspheres for detecting nitrobenzene
CN106009114A (en) * 2016-08-02 2016-10-12 苏州锐特捷化工制品有限公司 Tear-resistant functional rubber material for magnetic modification and preparation method thereof

Citations (1)

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Publication number Priority date Publication date Assignee Title
CN102815753A (en) * 2012-08-24 2012-12-12 上海交通大学 Fe3O4 nano-particles with high dispersion stability in water phase, and preparation method thereof

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Publication number Priority date Publication date Assignee Title
CN102815753A (en) * 2012-08-24 2012-12-12 上海交通大学 Fe3O4 nano-particles with high dispersion stability in water phase, and preparation method thereof

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WEN-SHENG ZOU ET AL.: "Selective fluorescence response and magnetic separation probe for 2,4,6-trinitrotoluene based on iron oxide magnetic nanoparticles", 《ANAL BIOANAL CHEM》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105363394A (en) * 2015-09-24 2016-03-02 济南大学 Preparation and application of magnetic fluorescent molecule imprinting nano-microspheres for detecting nitrobenzene
CN105363394B (en) * 2015-09-24 2017-11-07 济南大学 A kind of preparation and application of the magnetic fluorescence molecular engram nanoparticle for detecting nitrobenzene
CN106009114A (en) * 2016-08-02 2016-10-12 苏州锐特捷化工制品有限公司 Tear-resistant functional rubber material for magnetic modification and preparation method thereof

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