CN110270131A - Hydrophobicity eutectic solvent based on parabens compound and preparation method thereof and selective extraction application - Google Patents
Hydrophobicity eutectic solvent based on parabens compound and preparation method thereof and selective extraction application Download PDFInfo
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Abstract
The invention discloses a kind of hydrophobicity eutectic solvents based on parabens compound and preparation method thereof and selective extraction application, belong to Extraction of Heavy Metals separation and concentration technology field.Technical solution of the present invention main points are as follows: the hydrophobicity eutectic solvent based on parabens compound, it is using methyl tricapryl ammonium chloride as hydrogen bond receptor, using the parabens compound of different carbon chain lengths as hydrogen bond donor, synthesized by the molar ratio according to 1:0.25 ~ 4.The invention further particularly discloses the preparation method of the hydrophobicity eutectic solvent based on parabens compound and its to containing the application in 0.51 μ g/L of ultra trace to high concentration 1g/L Cr (VI) selective extraction in Cr (VI) aqueous solution.Hydrophobicity eutectic solvent prepared by the present invention is used as extractant, has many advantages, such as that low in cost, synthetic method is simple, performance is stable, less toxic and extraction efficiency is high.
Description
Technical field
The invention belongs to Extraction of Heavy Metals separation and concentration technology fields, and in particular to one kind is based on parabens compound
Hydrophobicity eutectic solvent and preparation method thereof and selective extraction application.
Background technique
Eutectic solvent is the new generation " green solvent " after ionic liquid.Typically refer to two or more
Substance be formed by by Hyarogen-bonding, fusing point lower than each constituent and be in a liquid state at room temperature eutectic mixing
Object.Outside the features such as eutectic solvent volatilizees in addition to possessing hardly possible possessed by ionic liquid, do not burn, electrochemical window mouth width, also have
There is synthesis simple, atom utilization 100% of preparation process reactant, low in cost, biodegradable.Due to having
Excellent physical and chemical performance, eutectic solvent are often used to substitute the more expensive ion of traditional volatile organic solvent and price
Liquid is applied to the fields such as organic synthesis, electrochemistry, catalysis, extraction and separation.
Liquid-liquid extraction is enrichment and purification technique commonly used in many industrial productions, compared with other techniques, liquid liquid
Extraction has that low energy consumption, equipment operation is easy and the advantages such as efficiently.Extractant is the core component of liquid-liquid extraction, traditional
Industrial extractant is mainly volatile organic solvent, with inflammable, volatile, high poison, difficult for biological degradation and Gao Chengben
Etc. many intrinsic disadvantages.Therefore, exploitation extraction ability it is good, it is inexpensive low toxicity, low volatility " green extractant ", to protection
Environmental and human health impacts develop sustainable friendly process production and are of great significance.
The various eutectic solvents reported at present be largely it is hydrophilic, preparation in relation to hydrophobicity eutectic solvent and
The research that it is applied is relatively fewer, and the document related to the present invention retrieved is as follows:
Zhu Junfang, Wang Xianying etc. have synthesized menthol-lactic acid hydrophobicity eutectic solvent, and use infrared spectroscopy, differential
The means such as scanning amount hot-hot weight analysis the structure and property of eutectic solvent are characterized (chemical research and application,
2018,30 (2), 219-225).Menthol-lactic acid eutectic solvent of document preparation is good with hydrophobicity, viscosity is small and right
The advantages that soluble end of other materials is wide, and due to menthol can be formed with the lactic acid in lactic acid-water mixed solution it is low
The concentration of lactic acid in lactic acid-water mixed solution is greatly lowered in congruent melting solvent.
Bent chess is using choline chloride as hydrogen bond receptor, with different types of phenol (phenol, catechol, resorcinol, adjacent first
Base phenol, m-methyl phenol, p-methyl phenol) it is hydrogen bond donor, 8 kinds of hydrophobicity eutectic have been synthesized according to certain molar ratio
Solvent (Institutes Of Technology Of Tianjin's Master dissertation, 2018).Then, hydrophobicity eutectic solvent as extractant and is combined
Ultrasonic wave added liquid-liquid micro-extraction detects four kinds of sulfonamides in environmental water sample, and the method achieve to sulfanilamide (SN) in environmental water sample
The Rapid Extraction of class drug and detection.
Zhu Shuqiang is using capric acid and octanoic acid as hydrogen bond donor, using methyl tricapryl ammonium chloride and tetrabutylammonium chloride as hydrogen
Key receptor is placed in 4 kinds of hydrophobicity eutectic solvent (Lanzhou University doctors of acquisition in 40 DEG C of oil bath pan according to certain molar ratio
Master dissertation, 2018).The method of document dispersive liquid-liquid microextraction assists four kinds of different hydrophobicity eutectic molten
8 kinds of synthetic dyestuffs in agent extracting beverage sample establish hydrophobicity eutectic solvent combination high effective liquid chromatography for measuring drink
The method of 8 kinds of synthetic dyestuffs in material can effectively measure the synthetic dyestuff in food.
The patent of Publication No. CN108593808A discloses a kind of hydrophobicity eutectic solvent vortex aid dispersion liquid liquid
Micro-extraction-high performance liquid chromatography detection formaldehyde method.This method is using quaternary ammonium salt as hydrogen bond receptor, with cyanophenol, to benzene
At least one of diphenol or parazon are hydrogen bond donor, according to the molar ratio synthesizing hydrophobic eutectic of 1:0.25~3
Solvent, and the method for combining the auxiliary liquid-liquid micro-extraction that is vortexed is successfully applied to the first in measurement biological sample and air sample
Aldehyde.
Up to the present, it has not been found that selecting the parabens of different carbon chain lengths in the data that we are grasped
Conjunction object is hydrogen bond donor, and methyl tricapryl ammonium chloride is that hydrogen bond receptor carrys out synthesizing hydrophobic eutectic solvent and is used for Cr
(VI) report of extraction and separation enrichment.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of hydrophobicity eutectic based on parabens compound is molten
Agent and preparation method thereof, the hydrophobicity eutectic solvent is simple with synthesis, raw material are easy to get, are low in cost, hydrophobic performance is good,
Glass transition temperature is very low, high stability and the advantages of place the several months and can keep better stability, prepared by the present invention
Hydrophobicity eutectic solvent based on parabens compound can be direct in the case where not adding any metal-chelator
Extraction is containing the Cr (VI) in Cr (VI) aqueous solution.
The technical issues of present invention also solves be the glass transition temperature for obtaining the hydrophobicity eutectic solvent, close
Physical properties such as degree, viscosity, hydrophobicity and its in application of the selective extraction containing Cr (VI) in Cr (VI) aqueous solution, the hydrophobicity
Eutectic solvent can extract containing the Cr (VI) in Cr (VI) aqueous solution according to the molar ratio of 1:1 and also have to the Cr of ultra trace (VI)
There is preferable effect of extracting；The hydrophobicity eutectic solvent is selected with very high extraction containing the Cr (VI) in Cr (VI) aqueous solution
When the concentration of selecting property, metal ion and neutral molecule is 2000 times of Cr (VI), hydrophobicity eutectic solvent is to containing Cr (VI) water
The extraction efficiency of Cr (VI) is still higher than 90% in solution.
The present invention adopts the following technical scheme that solve above-mentioned technical problem, the hydrophobicity based on parabens compound
Eutectic solvent, it is characterised in that: the hydrophobicity eutectic solvent is using methyl tricapryl ammonium chloride as hydrogen bond receptor, with not
Parabens compound with carbon chain lengths is hydrogen bond donor, synthesized by the molar ratio according to 1:0.25~4, wherein Ni Bo
Golden ester type compound is methylparaben, ethylparaben, propylben, butyl hydroxybenzoate, iso-butyl p-hy-droxybenzoate, nipalgin
One of n-octyl or the different monooctyl ester of nipalgin are a variety of.
Preferably, the glass transition temperature of the hydrophobicity eutectic solvent is -79.1~-24.2 DEG C, and density is
0.9262~1.0460g/cm3, viscosity is 778~2437mpas, and contact angle is 17.4 °~58.9 °.
The preparation method of hydrophobicity eutectic solvent of the present invention based on parabens compound, feature exist
In specific steps are as follows: weigh methyl tricapryl ammonium chloride and parabens respectively in molar ratio for the proportion of 1:0.25~4
Object is closed to be placed in reaction vessel, it is in 30~80 DEG C of 0.25~4h of heating stirring until forming uniform clear liquid, i.e., hydrophobic
Property eutectic solvent.
It is of the present invention based on the hydrophobicity eutectic solvent of parabens compound to contain Cr (VI) aqueous solution
Application in middle 0.51 μ g/L of ultra trace to high concentration 1g/L Cr (VI) selective extraction.
Preferably, the hydrophobicity eutectic solvent is preferably that methyl tricapryl ammonium chloride/butyl hydroxybenzoate hydrophobicity is low
Congruent melting solvent, the hydrophobicity eutectic solvent have best effect of extracting, extraction to containing the Cr (VI) in Cr (VI) aqueous solution
Rate is taken to be up to 98%.
Preferably, the hydrophobicity eutectic solvent is preferably that methyl tricapryl ammonium chloride/butyl hydroxybenzoate hydrophobicity is low
Congruent melting solvent, the hydrophobicity eutectic solvent have the Cr (VI) in the hexavalent chromium water solution of 100~1000mg/L of higher concentration
There is preferable removal effect, maximum extraction amount is 66.69mg/g, which extracts according to the molar ratio of 1:1
Containing the Cr (VI) in Cr (VI) aqueous solution.
Preferably, the hydrophobicity eutectic solvent is preferably that methyl tricapryl ammonium chloride/butyl hydroxybenzoate hydrophobicity is low
Congruent melting solvent, which has excellent extraction selectivity, in the metal ion or/and organic matter of high concentration
In the presence of, do not interfere the hydrophobicity eutectic solvent to the selective extraction containing Cr (VI) in Cr (VI) aqueous solution, wherein metal
Ion is Cu2+Or Cd2+One of or it is a variety of, organic matter be one of soluble starch or glucose or a variety of.
Preferably, the hydrophobicity eutectic solvent is preferably that methyl tricapryl ammonium chloride/butyl hydroxybenzoate hydrophobicity is low
Congruent melting solvent, the hydrophobicity eutectic solvent is with good stability, after the hydrophobicity eutectic solvent is placed 6 months its
90% is higher than to the extraction efficiency containing Cr (VI) in Cr (VI) aqueous solution.
Hydrophobicity eutectic solvent extractant of the present invention based on parabens compound, no matter to containing Cr
(VI) ultra trace Cr (VI) or high concentration Cr (VI) has excellent selective extraction performance, and 2000 times in aqueous solution
Metal ion and neutral molecule when coexisting, do not interfere its to the extraction containing Cr (VI) in Cr (VI) aqueous solution substantially.The present invention
The hydrophobicity eutectic solvent extractant performance is stablized, even if it is to containing Cr in Cr (VI) aqueous solution after placing 6 months
(VI) effect of extracting does not change substantially.Compared with prior art, the hydrophobicity eutectic solvent conduct prepared by the present invention
Extractant uses, and has many advantages, such as that low in cost, synthetic method is simple, performance is stable, less toxic and extraction efficiency is high.
Specific embodiment
Above content of the invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on above content of the present invention belong to this hair
Bright range.
Embodiment 1
Methyl tricapryl ammonium chloride and methylparaben are weighed according to the molar ratio of 1:0.25~2, then sets mixture
In a round bottom flask, 0.5~4h is stirred under 40~75 DEG C of heating condition until forming uniform clear liquid ,-
It is faint yellow clear liquid within the scope of 77.9~75 DEG C.
Embodiment 2
Methyl tricapryl ammonium chloride and butyl hydroxybenzoate are weighed according to the molar ratio of 1:0.25~3, then sets mixture
In a round bottom flask, 0.25~4h is stirred under 40~80 DEG C of heating condition until forming uniform clear liquid ,-
It is faint yellow clear liquid within the scope of 77.7~80 DEG C.
Embodiment 3
Methyl tricapryl ammonium chloride and iso-butyl p-hy-droxybenzoate are weighed according to the molar ratio of 1:0.25~3, then by mixture
It sets in a round bottom flask, stirs 0.25~4h under 45~80 DEG C of heating condition until forming uniform clear liquid,
It is faint yellow clear liquid within the scope of -62.3~80 DEG C.
Embodiment 4
Methyl tricapryl ammonium chloride and nipalgin n-octyl are weighed according to the molar ratio of 1:0.25~3, then by mixture
It sets in a round bottom flask, stirs 0.25~4h under 40~80 DEG C of heating condition until forming uniform clear liquid,
It is faint yellow clear liquid within the scope of -78.7~80 DEG C.
Embodiment 5
Methyl tricapryl ammonium chloride and the different monooctyl ester of nipalgin are weighed according to the molar ratio of 1:0.25~4, then by mixture
It sets in a round bottom flask, stirs 0.25~4h under 30~80 DEG C of heating condition until forming uniform clear liquid,
It is faint yellow clear liquid within the scope of -79.1~80 DEG C.
Embodiment 6
It is a certain amount of containing Cr in containing that hydrophobicity eutectic solvent synthesized by a certain amount of Examples 1 to 5 is weighed respectively
(VI) in aqueous solution.Under conditions of not adjusting solution ph, the content of Cr (VI) in water phase is measured after vortex centrifugal.According to survey
Determine result it is found that prepared all hydrophobicity eutectic solvents have effect of extracting to Cr in solution (VI), wherein embodiment 2
Synthesized methyl tricapryl ammonium chloride/butyl hydroxybenzoate hydrophobicity eutectic solvent is to containing the Cr (VI) in Cr (VI) aqueous solution
With best effect of extracting, extraction yield is up to 98%.
Embodiment 7
It is molten to measure methyl tricapryl ammonium chloride synthesized by a certain amount of embodiment 2/butyl hydroxybenzoate hydrophobicity eutectic
Then in container container is added in the gradation containing Cr (VI) aqueous solution for the 0.51 μ g/L super low concentration that total volume is 350mL by agent
In extracted, at room temperature after vortex centrifugal, discard water phase retain hydrophobicity eutectic solvent phase, then measure hydrophobicity it is low
The concentration of Cr (VI) in congruent melting solvent phase.Should the result shows that, methyl tricapryl ammonium chloride prepared by embodiment 2/nipalgin fourth
Extraction yield of the ester hydrophobicity eutectic solvent to super low concentration containing Cr (VI) in Cr (VI) aqueous solution is greater than 90%, the i.e. hydrophobicity
Eutectic solvent has excellent separation and enrichment performance to 0.51 μ g/L ultra trace target contaminant.
Embodiment 8
It is molten to weigh methyl tricapryl ammonium chloride synthesized by a certain amount of embodiment 2/butyl hydroxybenzoate hydrophobicity eutectic
Agent is added to containing a certain amount of containing in Cr (VI) aqueous solution.The dry of certain multiplying power concentration is added thereto under conditions of 40 DEG C
Object is disturbed, the content of Cr (VI) in water phase is measured after vortex certain time and centrifugation.The hydrophobicity eutectic solvent to Cr (VI) and
The extraction selectivity energy parameter of other metal ions and common organic matter is shown in Table 1.
The influence that 1 coexistent metallic ion of table and organic matter extract Cr (VI)
As it can be seen from table 1 not having substantially even if the amount of interfering ion is 2000 times of Cr (VI) to the extraction of Cr (VI)
It influences.Therefore, though high concentration metal ion (Cu2+, Cd2+) and organic matter (soluble starch, glucose) there are items
Under part, hydrophobicity eutectic solvent prepared by embodiment 2 to the extraction containing Cr (VI) in Cr (VI) aqueous solution still have compared with
High selectivity.
Embodiment 9
Containing 10mL, mass concentration be respectively 100mg/L, 200mg/L, 300mg/L, 400mg/L, 500mg/L,
100mg is added in the glass centrifuge tube of 600mg/L, 700mg/L, 800mg/L, 900mg/L and 1000mg/L hexavalent chromium solution
Methyl tricapryl ammonium chloride prepared by embodiment 2/butyl hydroxybenzoate hydrophobicity eutectic solvent, be vortexed 10min at 25 DEG C
After be centrifuged 10min, water intaking surveys Cr (VI) remaining content after mutually crossing 0.45 μm of water system film, and calculates the hydrophobicity eutectic solvent pair
The extraction quantity of Cr (VI).Table 2 gives the hydrophobicity eutectic solvent to the extraction quantity of different initial concentration hexavalent chromium solutions.
Extraction quantity of the 2 hydrophobicity eutectic solvent of table to different initial concentration hexavalent chromium solutions
As shown in Table 2, methyl tricapryl ammonium chloride prepared by embodiment 2/butyl hydroxybenzoate hydrophobicity eutectic solvent
Still there is preferable removal effect to the Cr (VI) containing higher concentration in Cr (VI) aqueous solution, maximum extraction amount is
66.69mg/g, when being calculated with molar ratio, i.e., 1mol hydrophobicity eutectic solvent can extract 1mol Cr (VI).
Embodiment 10
To place respectively 0 day, methyl tricapryl ammonium chloride prepared by the embodiment 2 after two weeks, 3 months and 6 months/
Butyl hydroxybenzoate hydrophobicity eutectic solvent is used to extract the Cr (VI) containing in Cr (VI) aqueous solution.The result shows that the hydrophobicity
Eutectic solvent is with good stability, even if it imitates the extraction containing Cr (VI) in Cr (VI) aqueous solution after placing 6 months
Rate is still higher than 90%.
Embodiment above describes basic principles and main features of the invention and advantage, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe originals of the invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (8)
1. the hydrophobicity eutectic solvent based on parabens compound, it is characterised in that: the hydrophobicity eutectic solvent
It is, using the parabens compound of different carbon chain lengths as hydrogen bond donor, to be pressed using methyl tricapryl ammonium chloride as hydrogen bond receptor
Synthesized by molar ratio according to 1:0.25 ~ 4, wherein parabens compound is methylparaben, ethylparaben, nipalgin
One of propyl ester, butyl hydroxybenzoate, iso-butyl p-hy-droxybenzoate, nipalgin n-octyl or the different monooctyl ester of nipalgin are a variety of.
2. the hydrophobicity eutectic solvent according to claim 1 based on parabens compound, it is characterised in that: institute
The glass transition temperature for stating hydrophobicity eutectic solvent is -79.1 ~ -24.2 DEG C, and density is 0.9262 ~ 1.0460g/cm3, stick
Degree is 778 ~ 2437mpa s, and contact angle is 17.4 ° ~ 58.9 °.
3. a kind of preparation method of the hydrophobicity eutectic solvent described in claim 1 based on parabens compound,
It is characterized in that specific steps are as follows: weigh methyl tricapryl ammonium chloride and paraben esters respectively in molar ratio for the proportion of 1:0.25 ~ 4
Class compound is placed in reaction vessel, in 30 ~ 80 DEG C of 0.25 ~ 4h of heating stirring until forming uniform clear liquid, that is, is dredged
Aqueous eutectic solvent.
4. it is described in claim 1 based on the hydrophobicity eutectic solvent of parabens compound to contain Cr (VI) aqueous solution
Application in middle 0.51 μ g/L of ultra trace to high concentration 1g/L Cr (VI) selective extraction.
5. application according to claim 4, it is characterised in that: the hydrophobicity eutectic solvent is preferably methyl trioctylphosphine
Ammonium chloride/butyl hydroxybenzoate hydrophobicity eutectic solvent, the hydrophobicity eutectic solvent is to containing the Cr in Cr (VI) aqueous solution
(VI) there is best effect of extracting, extraction yield is up to 98%.
6. application according to claim 4, it is characterised in that: the hydrophobicity eutectic solvent is preferably methyl trioctylphosphine
Ammonium chloride/butyl hydroxybenzoate hydrophobicity eutectic solvent, the hydrophobicity eutectic solvent is to 100 ~ 1000mg/L's of higher concentration
Cr (VI) in hexavalent chromium water solution has preferable removal effect, and maximum extraction amount is 66.69mg/g, the hydrophobicity eutectic
Solvent is according to the molar ratio extraction of 1:1 containing the Cr (VI) in Cr (VI) aqueous solution.
7. application according to claim 4, it is characterised in that: the hydrophobicity eutectic solvent is preferably methyl trioctylphosphine
Ammonium chloride/butyl hydroxybenzoate hydrophobicity eutectic solvent, which has excellent extraction selectivity, in height
In the presence of the metal ion or/and organic matter of concentration, do not interfere the hydrophobicity eutectic solvent to containing Cr in Cr (VI) aqueous solution
(VI) selective extraction, wherein metal ion is Cu2+Or Cd2+One of or it is a variety of, organic matter be soluble starch or Portugal
One of grape sugar is a variety of.
8. application according to claim 4, it is characterised in that: the hydrophobicity eutectic solvent is preferably methyl trioctylphosphine
Ammonium chloride/butyl hydroxybenzoate hydrophobicity eutectic solvent, the hydrophobicity eutectic solvent is with good stability, described hydrophobic
Property eutectic solvent place 6 months after its 90% is higher than to the extraction efficiency containing Cr (VI) in Cr (VI) aqueous solution.
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| CN113277589A (en) * | 2021-05-11 | 2021-08-20 | 廊坊师范学院 | Method for green absorption of formaldehyde in wastewater by using hydrophobic eutectic solvent |
| CN114588660A (en) * | 2022-02-24 | 2022-06-07 | 广东工业大学 | Hydrophobic deep eutectic solvent and preparation method and application thereof |
| CN115724811A (en) * | 2022-11-21 | 2023-03-03 | 河南师范大学 | Temperature response type phenol eutectic solvent and application thereof in selective separation of 5-hydroxymethylfurfural |
| CN115724811B (en) * | 2022-11-21 | 2024-03-08 | 河南师范大学 | Temperature response type phenol eutectic solvent and application thereof in selective separation of 5-hydroxymethylfurfural |
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