CN104897456B - The method for utilizing [C4mim] PF6 TBP binary extractants that phenol is enriched with from water - Google Patents
The method for utilizing [C4mim] PF6 TBP binary extractants that phenol is enriched with from water Download PDFInfo
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- CN104897456B CN104897456B CN201510233862.3A CN201510233862A CN104897456B CN 104897456 B CN104897456 B CN 104897456B CN 201510233862 A CN201510233862 A CN 201510233862A CN 104897456 B CN104897456 B CN 104897456B
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Abstract
The present invention utilizes [C for a kind of4mim]PF6The method that TBP binary extractants are enriched with phenol from water, the method is comprised the following steps：（1）, phenol solution is placed in centrifuge tube, dispersion liquid is subsequently adding, binary extractant is added, the 25min of ultrasonic disperse 3 at a temperature of 0 50 DEG C is well mixed, form the uniform microemulsion of high degree of dispersion；The composition of the binary extractant is [C4mim]PF6And TBP, volume ratio is [C4mim]PF6：TBP=1：0.4~3.7；（2）, after the microemulsion after ultrasound is centrifuged into 1 16min with 7000~10000rpm rotating speeds, phenol rich is in the precipitated phase ionic liquid of centrifugation bottom of the tube.Ionic liquid binary extractant system of the invention does not receive density, parent/hydrophobic limitation, with flexible controllability, has a wide range of application.
Description
Technical field
The present invention relates to one kind using ionic liquid [C4mim]PF6- TBP binary extractants are enriched with the side of phenol from water
Method.
Background technology
With social progress, the continuous improvement of quality of the life, environmental sanitation, food security etc. are close with mankind itself's health
The problem that cut is closed increasingly is taken seriously.Therefore the detection on environmental sanitation, food security is just most important.At present in sample
During product examine is surveyed, common Modern Methods, such as atomic absorption spectrography (AAS), atomic fluorometry, plasma emission spectroscopy
Method etc. can fast and accurately be analyzed detection to sample, and the accuracy of above method must be set up locating before sample
Manage on this primary and crucial step.
At present, for micro or trace samplings, common pre-treating method has SPME (SPME) and the micro- extraction of liquid phase
Take (LPME).Wherein, 2006, dispersive liquid-liquid microextraction method (DLPME) (the Rezaee M., Assadi of the proposition such as Rezaee
Y.,Hosseinia M.R.M.,Aghaee E.,Ahmadi F.,Berijani S.J.Chromatogr.A,2006,116(1-
2), 1-9) Solvent quantity is few, and maximize the contact area of extractant and sample solution by decentralized medium, thus enrichment
Multiple is high, detection limit are low, are current samples while having the operation advantage that easier, extraction time is short, relative standard deviation is low
One of newest optimal method of pre-treatment.
The dispersive liquid-liquid microextraction of early stage generally comprises density p>1 conventional organic solvent is used as extractant, such as chloroform, chlorine
Benzene, CCl4Deng to meet centrifugation and preferable concentration effect.Because organic extractant majority is water insoluble, so also needing to
Addition can be dissolved in the dispersant of water, such as methyl alcohol, acetonitrile, acetone, good so as to reach to form the multiphase emulsion of high degree of dispersion
Good effect of extracting.But the use of the organic solvents such as volatile extractant, dispersant greatly limit the system
Extensive use.
With the proposition of Green Chemistry concept and the fast development of ionic liquid at room temperature (ILs), for the micro- extraction of above liquid phase
Take and exist in use and the weak point such as organic solvent density and water miscible limitation of volatile organic solvent in system, week et al.
Propose within 2008 to be applied to liquid-phase micro-extraction with ionic liquid substitution volatile organic solvent, form ionic liquid dispersion phase micro-
Extraction (IL-DLPME) (Zhou Q.X., Bai H.H., Xie G.H., Xiao J.P.J.Chromatogr.A, 2008,177
(1),43-49).The characteristics of system make use of ionic liquid steam to force down well, it is to avoid making for volatile organic solvent
With.But have the following disadvantages simultaneously：
1. viscosity of il is big, and ionic liquid consumption is generally micro updating during micro-extraction, therefore causes micro-extraction body
The preparation and analytical sampling of system are more difficult；
2. ionic liquid density is big, therefore when by means of different force approach such as ultrasound, microwave or hand concussions, it is difficult to
The multiphase emulsion of high degree of dispersion is formed, causes to produce part to emulsify, so as to influence the effect of extracting for occurring at boundary layer；
3. ionic liquid is generally conventional ionic liquid, and concentration effect is not good.
Above deficiency greatly limit the extensive use of ionic liquid micro-extraction system.
For above weak point, there is research to make following improvement：With ionic liquid as extractant, organic solvent is added,
Such as methyl alcohol, acetonitrile, acetone are used as dispersant (Jalbani N., Soylak M.Food Chem., 2015,167,433-437；L., Boido E., Carrau F., Dellacassa E.J.Chromatogr.A, 2007,1157,46-50), to drop
The density of low system, viscosity, so as to form good emulsion.But organic dispersing agent is that hydrophilic routine has in this system
Machine solvent, only exists to reduce the viscosity and density of ion liquid abstraction agent as dispersant, and can not improve ionic liquid extraction
Take the concentration effect of agent system.
Therefore, the ionic liquid dispersion of efficiently concentrating effect can be realized again using this green solvent of ionic liquid
The deciding factor for being selected to the enrichment method of extractant in liquid-phase micro-extraction system.
The content of the invention
The present invention is directed to big above ionic liquid micro-extraction system viscosity, sampling complexity, density is big, disperse uneven and enrichment
The problems such as effect difference, propose to utilize [C4mim]PF6The method that-TBP binary extractants are enriched with phenol from water.Novelty of the present invention
Ground will be incorporated into ionic liquid dispersive liquid-liquid microextraction system for the extractant TBP of object phenol, forms ionic liquid
Binary extractant.The introducing of extractant TBP had both reduced density, the viscosity of ionic liquid, instead of again as the normal of dispersant
Rule organic solvent, improves concentration effect.
Technical scheme is as follows：
One kind utilizes [C4mim]PF6The method that-TBP binary extractants are enriched with phenol from water, comprises the following steps：
(1) phenol solution is placed in centrifuge tube, is subsequently adding dispersion liquid, add binary extractant, after being well mixed
The ultrasonic disperse 3-25min at a temperature of 0-50 DEG C, forms the uniform microemulsion of high degree of dispersion；
Wherein, volume ratio is phenol solution：Dispersion liquid：Binary extractant=1：0.6~0.7：0.02~0.06；Described
Dispersion liquid is inorganic salt solution or distilled water；
The composition of the binary extractant is [C4mim]PF6And TBP, volume ratio is [C4mim]PF6：TBP=1：0.4~
3.7；
(2) after the microemulsion after ultrasound being centrifuged into 1-16min with 7000~10000rpm rotating speeds, phenol rich is in centrifugation
In the precipitated phase ionic liquid of bottom of the tube.
The solubility scope of described phenol solution is 5 × 10-6-5×10-4mol/L。
The inorganic salts are KPF6, its solution concentration scope is 0.5~8.0g/L.
The invention is compared with existing ionic liquid micro-extraction system, with advantages below：
(1) viscosity of ionic liquid micro-extraction system can be effectively reduced using TBP, follow-up micro syringe is sampled
Operation is simpler；
(2) density of ionic liquid micro-extraction system can be effectively reduced using TBP, by means of ultrasound, microwave or shake
The effect of swinging is easier to be formed the uniform micro-extraction system of high degree of dispersion, maximizes extractant and object contact area product, so that
Improve concentration effect；
(3) the efficiently concentrating effect for phenol can be obtained using TBP, binary extractant system is 30 μ L in extractant
[C4mim]PF6During -30 μ L TBP, ultrasound 10min under the conditions of 0 DEG C, the optimal concentration effect after centrifugation 4min is 150.8, compared with
Ionic liquid [the C of document report6mim]PF6、[C8mim]PF6、[C6mim]BF4Or [C8mim]BF4For extractant, methyl alcohol are to divide
The optimum efficiency 90.02 of the micro-extraction system enrichment phenol of powder improves 68% (Zhang Yao, the micro-extraction side based on ionic liquid
Organic pollution in method determination of the environment sample, Master's thesis, Beijing：Beijing University of Chemical Technology, 2012：51-62.)；
Therefore, [C4mim]PF6- TBP binary extractant systems be a kind of green, efficiently, simple, efficiently example enrichment side
Method.
Brief description of the drawings
Fig. 1 is influence figure of the TBP consumptions to concentration effect in the binary extractant system that embodiment 1-5 is obtained
Fig. 2 is [C in the binary extractant system that embodiment 6-11 is obtained4mim]PF6Influence figure of the consumption to concentration effect
Fig. 3 is influence figure of the ultrasonic temperature to concentration effect in the binary extractant system that embodiment 12-17 is obtained
Fig. 4 is influence figure of the ultrasonic time to concentration effect in the binary extractant system that embodiment 18-23 is obtained
Fig. 5 is influence figure of the centrifugation time to concentration effect in the binary extractant system that embodiment 24-29 is obtained
Fig. 6 is influence figure of the salt effect to concentration effect in the binary extractant system that embodiment 30-34 is obtained
Specific embodiment
Below in conjunction with [the C that specific embodiment is provided the present invention4mim]PF6- TBP binary extractants benzene rich from water
The method of phenol is described in detail, but not thereby limiting the invention.
[C of the present invention4mim]PF6(1- butyl -3- methylimidazoles hexafluorophosphoric acid) is well known materials, can be by city
Sell or document obtains (Huddleston J.G., Willauer H.D., Swatloski R.P., Visser A.E., Rogers
R.D.Chem.Commum.,1998,16,1765-1766)。
Embodiment 1-5：
It is 5 × 10 to take 5 parts of concentration-4The phenol solution 3mL of mol/L is added in 10mL centrifuge tubes in each centrifuge tube
2mL distilled water, 30 μ L [C4mim]PF6Afterwards, then it is separately added into 30,50,70,90,110 μ L TBP (tributyl phosphate), hand shake
1 minute is swung after 30 DEG C of ultrasound 10min, milky microemulsion is formed, and dispersive liquid-liquid microextraction is carried out with this understanding.Extraction
The 8000rpm centrifugations 4min in supercentrifuge of system afterwards, ionic liquid is deposited on centrifugation bottom of the tube, phenol rich
In ionic liquid body phase.The μ L of ionic liquid body phase 20 are pipetted with micro syringe, 3mL is diluted to absolute ethyl alcohol, by UV-Vis instrument
Its absorbance is surveyed at 271.50nm wavelength, and calculates phenol content and enrichment times.Blank is the aqueous solution without phenol.It is rich
Collection multiple EF is calculated by formula 1, as a result as shown in Figure 1.
As shown in Figure 1, TBP consumptions are fewer, and the concentration effect of ionic liquid binary extractant Pyrogentisinic Acid is better.When TBP is used
Measure during for 30 μ L, enrichment times are 108.8.Illustrate the use of conventional extraction agent in ionic liquid binary extractant to ionic liquid
The concentration effect of micro-extraction system has significant impact.
Embodiment 6-11：
It is 5 × 10 to take 6 parts of concentration-4The phenol solution 3mL of mol/L distinguishes in 10mL centrifuge tubes in each centrifuge tube
After adding 2mL distilled water, 50 μ L TBP, then it is separately added into 30,40,50,70,90,110 μ L [C4mim]PF6, hand 1 point of concussion
Clock forms milky microemulsion after 30 DEG C of ultrasound 10min, and dispersive liquid-liquid microextraction is carried out with this understanding.After extraction
System in supercentrifuge 8000rpm centrifugations 4min, ionic liquid is deposited on centrifugation bottom of the tube, phenol rich in from
Sub- liquid phase.Pipette the μ L of ionic liquid body phase 20 with micro syringe, 3mL be diluted to absolute ethyl alcohol, by UV-Vis instrument in
Its absorbance is surveyed at 271.50nm wavelength, and calculates phenol content and enrichment times.Blank is the aqueous solution without phenol.Enrichment
Multiple EF is calculated by formula 1, as a result as shown in Figure 2.
As shown in Figure 2, [C4mim]PF6Consumption is fewer, and the concentration effect of ionic liquid binary extractant Pyrogentisinic Acid is better.When
[C4mim]PF6When consumption is 30 μ L, enrichment times are 75.5.From Fig. 1 and Fig. 2, the ratio of enrichment times and binary extractant
Example is unrelated, and relevant with consumption, and two kinds of Solvent quantities are fewer, and enrichment times are higher.Volume ratio is all 1:1 30 μ L-30 μ L
With 50 μ L-50 μ L binary extractant systems, enrichment times are respectively 108.8 and 64.6.Therefore, comprehensive sampling factor, binary extraction
Take agent preferably 30 μ L [C4mim]PF6With 30 μ L TBP.
Embodiment 12-17：
It is 5 × 10 to take 6 parts of concentration-4The phenol solution 3mL of mol/L distinguishes in 10mL centrifuge tubes in each centrifuge tube
Add 2mL distilled water, 30 μ L [C4mim]PF6With 30 μ L TBP, after hand concussion 1 minute, respectively at 0,10,20,30,40,50
Ultrasound 10min at a temperature of DEG C, forms milky microemulsion, and dispersive liquid-liquid microextraction is carried out with this understanding.After extraction
System 8000rpm centrifugations 4min in supercentrifuge, ionic liquid is deposited on centrifugation bottom of the tube, and phenol rich is in ion
Liquid phase.Pipette the μ L of ionic liquid body phase 20 with micro syringe, 3mL be diluted to absolute ethyl alcohol, by UV-Vis instrument in
Its absorbance is surveyed at 271.50nm wavelength, and calculates phenol content and enrichment times.Blank is the aqueous solution without phenol.Enrichment
Multiple EF is calculated by formula 1, as a result as shown in Figure 3.
From the figure 3, it may be seen that [C4mim]PF6The enrichment times of-TBP binary extractant systems being raised with temperature and are remarkably decreased, and 0
DEG C enrichment times are 150.8, and 50 DEG C is 97.1.
Embodiment 18-23：
It is 5 × 10 to take 6 parts of concentration-4The phenol solution 3mL of mol/L distinguishes in 10mL centrifuge tubes in each centrifuge tube
Add 2mL distilled water, 30 μ L [C4mim]PF6With 30 μ L TBP, hand concussion 1 minute after 30 DEG C respectively ultrasound 3,5,10,15,
20th, 25min, forms milky microemulsion, and dispersive liquid-liquid microextraction is carried out with this understanding.System after extraction is at a high speed
8000rpm centrifugations 4min in centrifuge, ionic liquid is deposited on centrifugation bottom of the tube, and phenol rich is in ionic liquid body phase.With
Micro syringe pipettes the μ L of ionic liquid body phase 20,3mL is diluted to absolute ethyl alcohol, by UV-Vis instrument at 271.50nm wavelength
Its absorbance is surveyed, and calculates phenol content and enrichment times.Blank is the aqueous solution without phenol.Enrichment times EF presses formula 1
Calculated, as a result as shown in Figure 4.
As shown in Figure 4, in 10min, enrichment times reach maximum 108.8 to ultrasonic time, therefore, in the present invention during ultrasound
Between preferably 10min.
Embodiment 24-29：
It is 5 × 10 to take 6 parts of concentration-4The phenol solution 3mL of mol/L distinguishes in 10mL centrifuge tubes in each centrifuge tube
Add 2mL distilled water, 30 μ L [C4mim]PF6With 30 μ L TBP, after 30 DEG C of ultrasound 10min, formation is milky white within 1 minute for hand concussion
The microemulsion of color, carries out dispersive liquid-liquid microextraction with this understanding.System after the extraction 8000rpm speed in supercentrifuge
Degree centrifugation 1,4,7,10,13,16min respectively, ionic liquid is deposited on centrifugation bottom of the tube, and phenol rich is in ionic liquid body phase.With
Micro syringe pipettes the μ L of ionic liquid body phase 20,3mL is diluted to absolute ethyl alcohol, by UV-Vis instrument at 271.50nm wavelength
Its absorbance is surveyed, and calculates phenol content and enrichment times.Blank is the aqueous solution without phenol.Enrichment times EF presses formula 1
Calculated, as a result as shown in Figure 5.
As shown in Figure 5, in 4min, enrichment times reach maximum 112.2 to centrifugation time, therefore, in the present invention during ultrasound
Between preferably 4min.
Embodiment 30-34：
It is 5 × 10 to take 5 parts of concentration-4The phenol solution 3mL of mol/L distinguishes in 10mL centrifuge tubes in each centrifuge tube
To add 2mL concentration be 0.5,2,4,6, the KPF of 8g/L6The aqueous solution, then it is separately added into 30 μ L [C4mim]PF6With 30 μ L TBP, hand
Shaking swings 1 minute after 30 DEG C of ultrasound 10min, forms milky microemulsion, and dispersive liquid-liquid microextraction is carried out with this understanding.
System after the extraction 8000rpm centrifugations 4min in supercentrifuge, ionic liquid is deposited on centrifugation bottom of the tube, phenol
It is enriched in ionic liquid body phase.The μ L of ionic liquid body phase 20 are pipetted with micro syringe, 3mL is diluted to absolute ethyl alcohol, by UV-
Vis instrument surveys its absorbance at 271.50nm wavelength, and calculates phenol content and enrichment times.Blank is without the water-soluble of phenol
Liquid.Enrichment times EF is calculated by formula 1, as a result as shown in Figure 6.
It will be appreciated from fig. 6 that KPF6Concentration/the ionic strength of solution is bigger, and the enrichment times of binary extractant system are smaller, when
KPF6When the concentration of solution is 0.5g/L, enrichment times are 109.5, higher than distilling aqueous systems under the same terms in embodiment 1-29
Optimum value 108.8.Therefore, concentration effect can be improved by adding a small amount of inorganic salts in the present invention.
Unaccomplished matter of the present invention is known technology.
Claims (2)
1. it is a kind of to utilize [C4mim]PF6The method that-TBP binary extractants are enriched with phenol from water, it is characterized by the method includes
Following steps：
（1）Phenol solution is placed in centrifuge tube, dispersion liquid is subsequently adding, binary extractant is added, is well mixed after 0-
Ultrasonic disperse 3-25min at a temperature of 50 DEG C, forms the uniform microemulsion of high degree of dispersion；
Wherein, volume ratio is phenol solution：Dispersion liquid：Binary extractant=1：0.6~0.7：0.02~0.06；Described dispersion
Liquid is inorganic salt solution or distilled water；
The composition of the binary extractant is [C4mim]PF6And TBP, volume ratio is [C4mim]PF6：TBP=1：0.4~3.7；
（2）After the microemulsion after ultrasound is centrifuged into 1-16min with 7000~10000rpm rotating speeds, phenol rich is in centrifuge tube bottom
In the precipitated phase ionic liquid in portion；
The inorganic salts are KPF6, its solution concentration scope is 0.5~8g/L.
2. it is as claimed in claim 1 to utilize [C4mim]PF6- TBP binary extractants are enriched with the method for phenol, its feature from water
For the solubility scope of described phenol solution is 5 × 10-6-5×10-4mol/L。
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| CN101915695A (en) * | 2010-08-11 | 2010-12-15 | 北京市农林科学院 | Centrifuge tube and method for micro-extraction of dispersion liquid |
| CN103245550A (en) * | 2013-04-16 | 2013-08-14 | 长安大学 | Method for separating and enriching trace phthalates by using pyridine type ionic liquid aqueous two-phase system |
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| CN101915695A (en) * | 2010-08-11 | 2010-12-15 | 北京市农林科学院 | Centrifuge tube and method for micro-extraction of dispersion liquid |
| CN103245550A (en) * | 2013-04-16 | 2013-08-14 | 长安大学 | Method for separating and enriching trace phthalates by using pyridine type ionic liquid aqueous two-phase system |
Non-Patent Citations (3)
| Title |
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| Removal of phenolic compounds from aqueous solutions by emulsion liquid membrance containing Ionic Liquid [BMIM]+[PF6]- in Tributyl phosphate;A. Balasubramanian et al.;《Desalination》;20120128(第289期);第27页第1节，第28页第2.1-2.3节，第29-33页第3节、图1 * |
| 疏水型室温离子液体用于放射性核素萃取分离研究;刘浩 等;《中国核科学技术进展报告（第一卷）》;20091130;全文 * |
| 磷酸三丁酯（TBP）对苯酚的络合萃取;杨义燕 等;《环境化学》;19950930;第14卷(第5期);全文 * |
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