CN107190157B - Remove the extractant and preparation method thereof of uranyl ion - Google Patents
Remove the extractant and preparation method thereof of uranyl ion Download PDFInfo
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- CN107190157B CN107190157B CN201710382202.0A CN201710382202A CN107190157B CN 107190157 B CN107190157 B CN 107190157B CN 201710382202 A CN201710382202 A CN 201710382202A CN 107190157 B CN107190157 B CN 107190157B
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- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B60/00—Obtaining metals of atomic number 87 or higher, i.e. radioactive metals
- C22B60/02—Obtaining thorium, uranium, or other actinides
- C22B60/0204—Obtaining thorium, uranium, or other actinides obtaining uranium
- C22B60/0217—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes
- C22B60/0252—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries
- C22B60/026—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries liquid-liquid extraction with or without dissolution in organic solvents
Abstract
The invention discloses a kind of extractant and preparation method thereof for removing uranyl ion, by asymmetric 4- oxo heptanedioyl amine as extraction reactant, functional form ionic liquid forms the extractant as diluent；The preparation method includes: synthesis asymmetry 4- oxo heptanedioyl amine；Isolate and purify asymmetric 4- oxo heptanedioyl amine；Synthesize ionic liquid；Prepare extractant.Extractant of the invention is good for uranium-bearing waste liquid extraction and separation effect, and synthesis cost is low, while not traditional organic solvent is volatile, toxicity is big, not radiation hardness and the disadvantages of be not easy pollution degradation environment, has broad application prospects.
Description
Technical field
The invention discloses a kind of solvent extraction agents and preparation method thereof, and in particular to a kind of extraction for removing uranyl ion
Agent and preparation method thereof.
Background technique
The separation of uranium and process of enriching are one important research projects of uranium-bearing liquid waste processing.The separation method of mainstream at present
There are solvent extraction, absorption method, supercritical CO2Fluid extraction uranium, Capillary Electrophoresis extraction uranium, concussion method extraction uranium etc..
Solvent extraction is the effective ways of current processing uranium-bearing waste liquid, and in extraction process, diluent is mainly traditional
Organic solvent, such as: kerosene, toluene and carbon tetrachloride etc..Traditional organic solvent is volatile, toxicity is big, radiation hardness and is not easy
The disadvantages of pollution degradation environment, compared with conventional organic solvents, ionic liquid has unique physicochemical property: 1. physics and chemistry are steady
Qualitative height, almost non-volatile, nonflammable, it is good to can be recycled 2. dissolubility, can dissolve most inorganic, organic material 3.
Have excellent electrochemical properties, such as 4. liquid temperature range is wide for higher conductivity and wider electrochemical window, from room temperature to
300 DEG C or more 5. structure have designability, the structure of zwitterion can be changed as needed, thus 6. changing its property has
Biggish polarity adjustability forms two-phase or multinomial system.There is very big advantage compared to conventional organic solvents.
The advantages that solvent extraction has reaction speed fast, good separating effect, at low cost, can be improved extraction efficiency, from
It separated in uranium-bearing waste liquid, remove uranyl ion to realize Selective Separation, and amide kind of extractants has convieniently synthesized, resistance to spoke
According to, not facile hydrolysis, catabolite is easy to wash to be removed, irradiation product can completely burned the advantages that, it is considered to be a new generation is important
Extractant.
Summary of the invention
The present invention is proposed to overcome disadvantage existing in the prior art, and the purpose is to provide a kind of removing uranyl
Extractant of ion and preparation method thereof.
The technical scheme is that
A kind of extractant removing uranyl ion, the extractant is by 4- oxo heptanedioyl amine as extraction reactant, function
Energy type ionic liquid mixes gained as diluent, with volume ratio 1:10；
The functional form ionic liquid is [Bmim]+PF6 -、[Hmim]+PF6 -、[Omim]+PF6 -In any one.
A kind of preparation method for the extractant removing uranyl ion, comprising the following steps:
(I) 4- oxo heptanedioyl amine is synthesized
Excessive thionyl chloride is added into 3,3 '-oxo dipropionic acids in (I), and is stirred at room temperature 3~5 hours；
(II) removes remaining thionyl chloride by the method for vacuum distillation from reaction system；
(III) is by HNRCH3(R=(CH2)n, wherein n=1,2,3) and it is added dropwise to reaction system dropwise in the presence of triethyl amine
In, 3~5 hours are vigorously stirred after being added dropwise to complete at 0 DEG C~3 DEG C in dry methylene chloride atmosphere to get thick organic mixing
Object；
(II) 4- oxo heptanedioyl amine is isolated and purified
The resulting thick organic mixture of step (III) is washed with mass fraction for 5% aqueous hydrochloric acid solution, it then will be organic
Layer is separated, and uses anhydrous Na SO4Wherein remaining moisture is removed, then is evaporated under reduced pressure, the product warp after evaporation
SGB-01 silica gel column chromatography purifies the 4- oxo heptanedioyl amine that purity to obtain the final product is more than 97%；
(III) ionic liquid is synthesized
0.1mol chloroethene isoxazolecarboxylic acid is added in (I) in the reaction vessel, adds 100ml methylene chloride, is then constantly stirring
By 0.12mol triethylamine and 0.12mol amine reagent HNR under conditions of mixing2(R=(CH2)nCH3, wherein n=1,2,3) mixing
Liquid is added dropwise in reaction vessel under ice cooling, 4, and when dropwise addition maintains the temperature between 0 DEG C~5 DEG C, and continuation is added dropwise at this
At a temperature of react 3h, after fully reacting, with 50ml mass fraction be that 5%HCl is washed three times, then three times with 50ml washing, it is dry,
Vacuum distillation obtains deep yellow color liquid product；
Deep yellow color liquid product obtained by the step of 0.1mol (I) is added in (II) in the reaction vessel, adds 0.1molN,
N- dialkyl group monoxone amide, and the 1- methylimidazole of same molar is added, then it is heated to reflux in oil bath at 85 DEG C
48h, after completion of the reaction, system become dark yellow solid product, directly put into the product and react in next step；
(III) into step (II) products therefrom, be added 1.1mol amount Potassium Hexafluorophosphate, 100ml methylene chloride and
0.5h stratification is stirred at room temperature in the deionized water of 200ml, and then organic phase and water phase are poured into separatory funnel and are layered,
Then deionized water, repetitive operation are separated, until the water phase to come out cannot be such that silver nitrate aqueous solution becomes cloudy；Then will
Methylene chloride is first removed in organic phase vacuum distillation, then removes water, finally obtains deep yellow color liquid ionic liquid；
(IV) extractant is prepared
Make extraction reactant, step (III) resulting ionic liquid with the resulting 4- oxo heptanedioyl amine of step (II)
[Cnmim][PF6] (wherein n=4,6,8) is mixed as diluent according to the ratio of mass ratio 1:10, and is shaken in an oscillator
One hour to get the extractant for arriving removing uranyl ion.
The beneficial effects of the present invention are:
The present invention provides a kind of Novel Extractants and preparation method thereof of uranyl ion in removing uranium-bearing waste liquid, with synthesis
4- oxo heptanedioyl amine as extraction reactant, functional form ionic liquid is as diluent, 4- oxo heptanedioyl amine, easily and uranium
Acyl ion chelating can greatly improve extraction efficiency；Ion liquid system has the radionuclide including uranyl ion
Preferable extraction efficiency, wherein best with imidazole ion liquid system extraction efficiency.Extractant of the invention is for uranium-bearing waste liquid
Extraction and separation effect is good, and synthesis cost is low, while not traditional organic solvent is volatile, toxicity is big, radiation hardness and is not easy
It the disadvantages of pollution degradation environment, has broad application prospects.
Detailed description of the invention
Fig. 1 is the 4- oxo heptanedioyl amine nuclear magnetic resonance spectroscopy spectrogram that the embodiment of the present invention 1 synthesizes；
Fig. 2 is the 4- oxo heptanedioyl amine nuclear magnetic resonance that the embodiment of the present invention 1 synthesizes13C composes spectrogram.
Specific embodiment
With reference to the accompanying drawings of the specification and embodiment to extractant and preparation method thereof of present invention removing uranyl ion into
Row is described in detail:
A kind of extractant removing uranyl ion, the extractant is by 4- oxo heptanedioyl amine as extraction reactant, function
Energy type ionic liquid mixes gained as diluent, with volume ratio 1:10.
The functional form ionic liquid is [Cnmim][PF6], wherein n=4,6,8.
The functional form ionic liquid is [Bmim]+PF6 -、[Hmim]+PF6 -、[Omim]+PF6 -In any one.
A kind of preparation method for the extractant removing uranyl ion, comprising the following steps:
(I) 4- oxo heptanedioyl amine is synthesized
Reaction equation is as follows:
Excessive thionyl chloride is added into 3,3 '-oxo dipropionic acids in (I), and is stirred at room temperature 3~5 hours；
(II) removes remaining thionyl chloride by the method for vacuum distillation from reaction system；
(III) is by HNRCH3(R=(CH2)n, wherein n=1,2,3) and it is added dropwise to reaction system dropwise in the presence of triethyl amine
In, 3~5 hours are vigorously stirred after being added dropwise to complete at 0 DEG C~3 DEG C in dry methylene chloride atmosphere to get thick organic mixing
Object；
(II) 4- oxo heptanedioyl amine is isolated and purified
The resulting thick organic mixture of step (III) is washed with 5% aqueous hydrochloric acid solution, then separates organic layer,
And use anhydrous Na SO4Wherein remaining moisture is removed, then is evaporated under reduced pressure, the product after evaporation is through SGB-01 silica gel column layer
Analysis purifies the 4- oxo heptanedioyl amine that purity to obtain the final product is more than 97%；
(III) ionic liquid is synthesized
0.1mol chloroethene isoxazolecarboxylic acid is added in 250ml round-bottomed flask, the methylene chloride of 100ml is added, then continuous
By 0.12mol triethylamine and 0.12mol amine reagent HNR under conditions of stirring2(R=(CH2)nCH3, wherein n=1,2,3) it is mixed
It closes liquid to be added drop-wise in flask under ice cooling, 4, keeps every temperature of flask at 0-5 DEG C when dropwise addition, continuation is added dropwise in the temperature
Degree is lower to react 3h, after fully reacting, is washed three times with 50ml5%HCl, then three times with 50ml washing, dry, vacuum distillation obtains
Deep yellow color liquid product.
The previous step product of 0.1mol is added in 250ml single port bottle, adds 0.1molN, N- dialkyl group monoxone acyl
Amine, and the 1- methylimidazole of same molar is added, then 48h is heated to reflux in oil bath at 85 DEG C.After completion of the reaction, system
Become dark yellow solid product.Directly the product is put into and is reacted in next step.
Previous step product is all added in 250ml beaker, the Potassium Hexafluorophosphate of 1.1mol amount, 100ml bis- are added
0.5h stratification is stirred at room temperature in the deionized water of chloromethanes and 200ml, and organic phase and water phase are then poured into liquid separation leakage
It is layered in bucket, then divides deionized water.It is repeated 8 times in this way, until the water phase to come out cannot make silver nitrate aqueous solution become muddy
It is turbid.Then methylene chloride is first removed into organic phase vacuum distillation, then removes water, finally obtain the buff that yield is 96%
Liquids Ionic liquids.Use amine reagent HNRCH3(R=(CH2)n, wherein n=1,2,3) ionic liquid that finally synthesizes, work as n=1
When, ionic liquid is referred to as [Bmim]+PF6 -, as n=2, ionic liquid is referred to as [Hmim]+PF6 -, as n=3, ionic liquid
Body is referred to as [Omim]+PF6 -。
(IV) extractant is prepared
Make extraction reactant, step (III) resulting ionic liquid with the resulting 4- oxo heptanedioyl amine of step (II)
[Cnmim][PF6] (wherein n=4,6,8) is mixed as diluent according to the ratio of mass ratio 1:10, and is shaken in an oscillator
One hour to get the extractant for arriving removing uranyl ion.
Eluant, eluent in the SGB-01 silica gel column chromatography purifying is mixed by petroleum ether and ethyl acetate according to volume ratio 10:1
Conjunction configures.
Embodiment 1
A kind of preparation method for the extractant removing uranyl ion, comprising the following steps:
(I) 4- oxo heptanedioyl amine is synthesized
0.11mol thionyl chloride is added to 0.1mol3 in (I) in 3 '-oxo dipropionic acids, and is stirred at room temperature 4 hours；
(II) removes 10% remaining thionyl chloride by the method for vacuum distillation from reaction system；
(III) is by 0.1molHNCH2CH3Be added dropwise in reaction system dropwise in the presence of triethyl amine, after being added dropwise to complete
3~5 hours are vigorously stirred to get thick organic mixture at 0 DEG C~3 DEG C in dry methylene chloride atmosphere；
(II) 4- oxo heptanedioyl amine is isolated and purified
The resulting thick organic mixture of step (III) is washed with for 5% aqueous hydrochloric acid solution, then isolates organic layer
Come, and uses anhydrous Na SO4Wherein remaining moisture is removed, then is evaporated under reduced pressure, the product after evaporation is through SGB-01 silica gel
Column chromatographic purifying is more than 97% 4- oxo heptanedioyl amine, earning rate 85% up to purity；
(III) two-step method synthesizes ionic liquid
0.1mol chloroethene isoxazolecarboxylic acid is added in 250ml round-bottomed flask, the methylene chloride of 100ml is added, then continuous
By 0.12mol triethylamine and 0.12mol amine reagent HNR under conditions of stirring2(R=(CH2)nCH3, wherein n=1,2,3) it is mixed
It closes liquid to be added drop-wise in flask under ice cooling, 4, keeps every temperature of flask at 0-5 DEG C when dropwise addition, continuation is added dropwise in the temperature
Degree is lower to react 3h, after fully reacting, is washed three times with 50ml5%HCl, then three times with 50ml washing, dry, vacuum distillation obtains
Deep yellow color liquid product.
0.1mol is added in 250ml single port bottle is being added 0.1molN, N- dialkyl group monoxone amide, and phase is added
With the 1- methylimidazole of mole, 48h then is heated to reflux in oil bath at 85 DEG C.After completion of the reaction, system becomes buff
Solid product.Directly the product is put into and is reacted in next step.
Previous step product is all added in 250ml beaker, adds the Potassium Hexafluorophosphate of 1.1mol amount, 100ml dichloro
The deionized water of methane and 200ml is stirred at room temperature 0.5h stratification, organic phase and water phase is then poured into separatory funnel
Middle layering, then divides deionized water.It is repeated 8 times in this way, until the water phase to come out cannot be such that silver nitrate aqueous solution becomes cloudy
?.Then methylene chloride is first removed into organic phase vacuum distillation, then removes water, finally obtain the buff liquid that yield is 96%
Body ionic liquid.
(IV) extractant is prepared
Make extraction reactant, step (III) resulting ionic liquid with the resulting 4- oxo heptanedioyl amine of step (II)
[Cnmim][PF6] (wherein n=4,6,8) is mixed as diluent according to the ratio of mass ratio 1:10, and is shaken in an oscillator
One hour to get the extractant for arriving removing uranyl ion.
As shown in Fig. 1/2, synthesized extraction reactant spectroscopic data, for DMDOHA (4- oxo heptanedioyl amine),1HNMR
(CDCl3, 400MHz): D 3.78 (t, J=9.2Hz, 4h), 3.34 (t, J=10Hz, 2h), 3.25 (t, J=10.0Hz, 2h)
2.97 (S, 3h), 2.91 (S, 3H) 2.61 (m, 4h) 1.57,1.49-(m, 4h), 1.27-1.29 (m, 20h), 0.85-0.91 (Q,
6h)PPM；13C NMR(CDCl3, 100MHz): D 170.26,66.77,49.86,34.89,33.61,32.95,32.71,
31.21,26.59,22.45,14.25 29.25,.
DMDOHA (4- oxo heptanedioyl amine): theoretical calculation obtains: C 69.86%, H 11.72%, N 6.79%, O
11.63%；It obtains test spectrogram by inspection to obtain: C 69.79%, H 11.69%, N 6.76%, O 11.70%.Detection knot
Fruit shows smoothly synthesize high-purity 4- oxo heptanedioyl amine extraction reactant.
Claims (2)
1. a kind of preparation method for the extractant for removing uranyl ion, it is characterised in that: the following steps are included:
(I) 4- oxo heptanedioyl amine is synthesized
Excessive thionyl chloride is added into 3,3 '-oxo dipropionic acids in (I), and is stirred at room temperature 3~5 hours；
(II) removes remaining thionyl chloride by the method for vacuum distillation from reaction system；
(III) is by HNRCH3(R=(CH2)n, wherein n=1,2,3) and it is added dropwise in reaction system dropwise in the presence of triethyl amine,
3~5 hours are vigorously stirred to get thick organic mixture at 0 DEG C~3 DEG C in dry methylene chloride atmosphere after being added dropwise to complete；
(II) 4- oxo heptanedioyl amine is isolated and purified
The resulting thick organic mixture of step (III) is washed with mass fraction for 5% aqueous hydrochloric acid solution, then by organic layer point
It separates out and, and use anhydrous Na SO4Wherein remaining moisture is removed, then is evaporated under reduced pressure, the product after evaporation is through SGB-01
Silica gel column chromatography purifies the 4- oxo heptanedioyl amine that purity to obtain the final product is more than 97%；
(III) ionic liquid is synthesized
0.1mol chloroethene isoxazolecarboxylic acid is added in (I) in the reaction vessel, adds 100ml methylene chloride, is then being stirred continuously
Under the conditions of by 0.12mol triethylamine and 0.12mol amine reagent HNR2(R=(CH2)nCH3, wherein n=1,2,3) mixed liquor exist
It is added dropwise in reaction vessel under ice bath is cooling, when dropwise addition maintains the temperature between 0 DEG C~5 DEG C, and continuation is added dropwise in the temperature
Lower reaction 3h is that 5%HCl is washed three times, then three times with 50ml washing, drying is depressurized with 50ml mass fraction after fully reacting
Distillation obtains deep yellow color liquid product；
Deep yellow color liquid product obtained by the step of 0.1mol (I) is added in (II) in the reaction vessel, adds 0.1molN, N- bis-
Alkyl chloride amide, and the 1- methylimidazole of same molar is added, it then is heated to reflux 48h in oil bath at 85 DEG C, instead
After answering, system becomes dark yellow solid product, directly puts into the product and reacts in next step；
The Potassium Hexafluorophosphate of 1.1mol amount, 100ml methylene chloride and 200ml is added into step (II) products therefrom in (III)
Deionized water, 0.5h stratification is stirred at room temperature, then organic phase and water phase are poured into separatory funnel and are layered, is then divided
It leaves away ionized water, repetitive operation, until the water phase to come out cannot be such that silver nitrate aqueous solution becomes cloudy；Then by organic phase
Methylene chloride is first removed in vacuum distillation, then removes water, finally obtains deep yellow color liquid ionic liquid；
(IV) extractant is prepared
Make extraction reactant, the resulting ionic liquid [C of step (III) with the resulting 4- oxo heptanedioyl amine of step (II)nmim]
[PF6] (wherein n=4,6,8) is mixed as diluent according to the ratio of mass ratio 1:10, and concussion one is small in an oscillator
When to get to removing uranyl ion extractant.
2. a kind of preparation method of extractant for removing uranyl ion according to claim 1, it is characterised in that: described
Eluant, eluent in the purifying of SGB-01 silica gel column chromatography is formed by petroleum ether and ethyl acetate according to volume ratio 10:1 mixed configuration.
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