CN114315565A - Glycolic acid/alanine natural eutectic ionic liquid and preparation method and application thereof - Google Patents
Glycolic acid/alanine natural eutectic ionic liquid and preparation method and application thereof Download PDFInfo
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 100
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 title claims abstract description 62
- 235000004279 alanine Nutrition 0.000 title claims abstract description 62
- 230000005496 eutectics Effects 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 19
- 150000002500 ions Chemical class 0.000 claims abstract description 16
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910001429 cobalt ion Inorganic materials 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 abstract description 63
- 239000002699 waste material Substances 0.000 abstract description 15
- 238000005065 mining Methods 0.000 abstract description 7
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 229910017052 cobalt Inorganic materials 0.000 description 8
- 239000010941 cobalt Substances 0.000 description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000006228 supernatant Substances 0.000 description 5
- 229910021642 ultra pure water Inorganic materials 0.000 description 5
- 239000012498 ultrapure water Substances 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 3
- 238000003968 anodic stripping voltammetry Methods 0.000 description 3
- 238000000658 coextraction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- HSSJULAPNNGXFW-UHFFFAOYSA-N [Co].[Zn] Chemical compound [Co].[Zn] HSSJULAPNNGXFW-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 238000004043 dyeing Methods 0.000 description 1
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- 230000036541 health Effects 0.000 description 1
- -1 low price Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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Abstract
The invention relates to the technical field of ionic liquid preparation, and particularly discloses a glycolic acid/alanine natural eutectic ionic liquid, and a preparation method and application thereof. The glycolic acid/alanine natural eutectic ionic liquid is prepared from glycolic acid and alanine. The glycolic acid/alanine natural eutectic ionic liquid can be used as a heavy metal ion extractant. The natural eutectic ionic liquid provided by the invention is particularly suitable for being used as an extractant of heavy metal divalent cobalt ions and divalent lead ions in mining waste residues, can realize extremely high extraction rate and extraction capacity of the divalent cobalt ions and the divalent lead ions, and can realize 100% extraction rate of the divalent cobalt ions under the condition of single extraction.
Description
Technical Field
The invention relates to the technical field of ionic liquid preparation, in particular to a glycolic acid/alanine natural eutectic ionic liquid and a preparation method and application thereof.
Background
Heavy metal cobalt pollution generally comes from industries such as printing and dyeing, mining, smelting and the like, and waste residues generated by mining are one of main sources of the heavy metal cobalt. Co can enter human bodies and the environment through various channels such as atmosphere, water bodies and the like, thereby causing atmospheric water body pollution and harming human health. The secondary recycling of cobalt resources is particularly important because of the scarcity and gradual depletion of the initial cobalt resources, which results in higher supply risk of cobalt. The current technology for recovering and separating the heavy metal Co in the waste residue is mainly a solvent extraction method, but the solvent extraction method has certain limitations, such as the need of using a large amount of organic solvent, complex process flow and the like. Therefore, a new cobalt extraction method is urgently needed, and the harmless treatment and resource recovery of Co in waste residues are realized by combining green chemistry and a cleaning technology.
With the progress of the theory and technical research of green chemistry, the research of ionic liquid as an extractant in the environmental field is gradually rising. Compared with the traditional solvent, the ionic liquid has the characteristics of low vapor pressure, difficult volatilization, stable property, wide liquid range, good solubility, cyclic utilization and the like. However, the ionic liquids currently used for Co extraction have the following disadvantages: low extraction capacity, limited single extraction rate, high eutectic melting point, insolubility in water, and unsatisfactory mass transfer process due to high viscosity. The defects cause that the current ionic liquid has larger application limitation in the field of Co extraction.
In recent years, the use of ionic liquids to separate Co from waste residues has been studied, such as "high selective separation and synthesis extraction of zinc from zinc-cobalt slag by ionic liquid [ Hbet][Tf2N]–H2In the O-system, A novel method for separating zinc and cobalt ", a carboxy-functionalized betaine bis (trifluoromethylsulfonyl) imide ([ Hbet)][Tf2N]) The ionic liquid separated Co, but the separation rate was only 21.03%, and the separation rate was low. In view of the environmental protection advantages exhibited by eutectic ionic liquids prepared from natural materials, it is very necessary to find a novel green absorbing material prepared from natural materials and having good separation efficiency.
Disclosure of Invention
The natural eutectic ionic liquid is prepared from natural raw materials, is green and environment-friendly, has low price, is easy to dissolve in water at the lowest liquid state of-15.9 ℃, has good mass transfer effect, and has the advantages of high single extraction rate and large extraction capacity when being used for Co extraction.
In order to achieve the purpose of the invention, the embodiment of the invention adopts the following technical scheme:
a glycolic acid/alanine natural eutectic ionic liquid is prepared from glycolic acid and alanine.
Compared with the prior art, the natural eutectic ionic liquid provided by the invention has the characteristics of wide and natural raw material sources, low price, high thermal stability (good eutectic characteristics) and water solubility, can adjust the characteristics of eutectic ionic liquid such as density, viscosity, conductivity, surface tension and the like by adjusting the concentration of an ionic liquid aqueous solution, and greatly expands the application range of the ionic liquid. In addition, the natural eutectic ionic liquid provided by the invention is used as an extractant of heavy metal divalent cobalt ions and divalent lead ions in mining waste residues, can realize extremely high extraction rate and extraction capacity, and can realize 100% extraction rate of divalent cobalt ions under the condition of single extraction.
The natural eutectic ionic liquid provided by the invention has the characteristics of green and environment-friendly raw materials, low price, liquid state at room temperature and the like, and provides a new idea for the research of the ionic liquid.
Preferably, the molar ratio of glycolic acid to alanine is 1-5: 1.
Preferably, the molar ratio of glycolic acid to alanine is 4: 1.
When the molar ratio of the glycolic acid to the alanine is 4:1, the eutectic melting point of the obtained ionic liquid can be as low as-15.9 ℃, and the eutectic ionic liquid has a better effect of extracting heavy metal divalent cobalt in mining waste residues.
The invention also provides a preparation method of the glycolic acid/alanine natural eutectic ionic liquid. The preparation method at least comprises the following steps: mixing said glycolic acid and said alanine and grinding to a solid powder, in N2And under protection, heating the solid powder to 78-82 ℃ for reaction until a transparent uniform liquid is formed, and drying the liquid to obtain the glycolic acid/alanine natural eutectic ionic liquid.
Compared with the prior art, the preparation method of the glycolic acid/alanine natural eutectic ionic liquid provided by the invention is simple to operate, safe, environment-friendly, green and pollution-free, and has extremely high popularization and application values.
Preferably, the drying method is vacuum drying, and the drying time is 15-25 h.
The invention provides application of the glycolic acid/alanine natural eutectic ionic liquid in serving as a heavy metal ion extracting agent.
Preferably, the heavy metal ion is a divalent cobalt ion.
Preferably, the heavy metal ions are divalent lead ions.
The invention also provides a method for extracting heavy metal ions by using the glycolic acid/alanine natural eutectic ionic liquid, which comprises the following specific steps: dissolving the glycolic acid/alanine natural eutectic ionic liquid in water to enable the concentration of the glycolic acid/alanine natural eutectic ionic liquid to reach 0.1-0.6 mol/L, adding a sample to be extracted, and then extracting for 1-6h at the pressure of 0.08-0.12MPa and the temperature of 10-60 ℃.
Preferably, the method for extracting heavy metal ions by using the glycolic acid/alanine natural eutectic ionic liquid comprises the following steps: dissolving the glycolic acid/alanine natural eutectic ionic liquid in water to enable the concentration of the glycolic acid/alanine natural eutectic ionic liquid to reach 0.4mol/L, adding a sample to be extracted, and extracting for 4h at the pressure of 0.1MPa and the temperature of 40 ℃.
Drawings
FIG. 1 is a graph showing the melting point of glycolic acid/alanine eutectic ionic liquids prepared at different ratios of raw materials in example 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
A glycolic acid/alanine natural eutectic ionic liquid is prepared from glycolic acid and alanine.
Wherein the formula of glycolic acid is as follows:
alanine has the following formula:
the other methods of the glycolic acid/alanine natural eutectic ionic liquid are as follows:
weighing five molar ratios (1:1, 2:1, 3:1, 4:1, 5:1) of glycolic acid and alanine, mixing, grinding into uniform solid powder, and adding N2Under protection, the ground solid powder is placed in a constant-temperature electric heating jacket and heated at 80 ℃ until uniform and transparent liquid is formed, the prepared liquid is dried for 20 hours in vacuum to obtain glycolic acid/alanine natural eutectic ionic liquid, and the glycolic acid/alanine natural eutectic ionic liquid is transferred to a dry reagent bottle for standby. The water content of the five ionic liquids with different glycolic acid/alanine molar ratios is detected to be 0.35-0.40%.
The eutectic melting points of the five ionic liquids obtained above with different molar ratios of glycolic acid/alanine were measured, and the results are shown in fig. 1, wherein the eutectic ionic liquid obtained with a molar ratio of glycolic acid to alanine of 4:1 had the lowest eutectic melting point, specifically-15.9 ℃.
FT-IR characterization and HNMR characterization were performed on the eutectic ionic liquid prepared at a molar ratio of glycolic acid to alanine of 4:1, respectively.
The FT-IR characterization results were as follows: OH (3376 cm)-1The peak of the stretching vibration); CH (CH)2，CH(2940cm-1The peak of the stretching vibration); c ═ O (1742 cm)-1The peak of the stretching vibration); NH (1624cm-1Peak of flexural vibration) OH (1426cm-1Bending vibration peak); CH (1426 cm)-1Bending vibration peak); C-O (1203 cm)-1Symmetric stretching vibration peaks); C-O (1088 cm)-1Asymmetric stretching vibration peak).
HNMR characterization results were as follows, glycolic acid alanine 4:1,1HNMR(500MHz,dmso-d6，δ:x10-6)：1.32(m,3H,CH3),3.90(s,4H,CH2),4.11(s,2H,CH2),4.52(s,2H,CH2),4.83(m,1H,CH),6.5-9.0(b,11H,OH,COOH,NH2)。
the basic properties of the eutectic ionic liquid obtained when the molar ratio of glycolic acid to alanine was 4:1 were measured, and the results are shown in table 1.
TABLE 1 basic Properties of Ionic liquids
| Property/temperature | 30℃ | 40 |
50℃ | 60℃ | 70℃ |
| Density (g/cm)3) | 1.3809 | 1.3761 | 1.3714 | 1.3658 | 1.3607 |
| Viscosity (mPa. s) | 3440 | 1417 | 637 | 292 | 180 |
| Conductivity (mS/cm) | 0.06 | 0.14 | 0.29 | 0.57 | 0.93 |
| Surface tension (mN/m) | 49.88 | 46.90 | 44.88 | 42.52 | 40.58 |
After the eutectic ionic liquid prepared when the molar ratio of glycolic acid to alanine was 4:1 was prepared into a 0.4mol/L ionic liquid solution with ultrapure water, the basic properties were examined and the examination results are shown in Table 2.
TABLE 2 basic Properties of aqueous Ionic liquids
| Property/temperature | 30℃ | 40 |
50℃ | 60℃ | 70℃ |
| Density (g/cm)3) | 1.0103 | 1.0043 | 0.9981 | 0.9925 | 0.9879 |
| Viscosity (mPa. s) | 0.95 | 0.78 | 0.67 | 0.58 | 0.51 |
| Conductivity (mS/cm) | 2.52 | 2.75 | 3.04 | 3.29 | 3.55 |
| Surface tension (mN/m) | 48.98 | 45.24 | 42.73 | 39.74 | 37.64 |
From the basic properties of the ionic liquids in tables 1 and 2, it can be seen that the adjustment of the characteristics of the eutectic ionic liquid, such as density, viscosity, conductivity and surface tension, can be realized by adjusting the concentration of the glycolic acid/alanine natural eutectic ionic liquid aqueous solution, and the application range and the easy operability of the ionic liquid are expanded.
Example 2
Eutectic ionic liquid prepared at a molar ratio of glycolic acid to alanine of 4:1 for heavy metal Co in example 12+The extraction conditions of (1).
Adding 15g of CoCl2·6H2Fully dissolving O in 20mLUP water, adding 5g of silica gel, uniformly stirring in a magnetic stirrer, stirring for 10 hours, rotationally evaporating under vacuum condition, finally drying in an oven at 120 ℃ for 12 hours until constant weight is achieved, and obtaining the Co for the experiment2+The simulated waste sample of (1).
Weighing 0.4037gCoCl2·6H2Obtaining 1g/L Co in a volumetric flask with O constant volume of 100mL2+Diluting the standard solution by 50 times, 100 times, 200 times, 300 times, 400 times and 500 times respectively, and measuring by anodic stripping voltammetry to obtain Co2+The standard curve of (2).
Preparing the eutectic ionic liquid with ultrapure water into ionic liquid aqueous solution with the concentration of 0.1mol/L, 0.2mol/L, 0.3mol/L, 0.4mol/L, 0.5mol/L and 0.6mol/L, taking out 20mL of the ionic liquid aqueous solution, putting the ionic liquid aqueous solution into a 100mL round-bottom flask, adding 3g of simulated soil sample, stirring for 4h at 40 ℃ for extraction experiment, centrifuging at 3500r/min by using a low-speed centrifuge for 15min, taking out supernatant, diluting the supernatant, and measuring Co by using anodic stripping voltammetry2+To thereby calculate Co2+The extraction rate of (2).
Extraction yield (Co in supernatant)2+Total amount of (C)/Co in the soil sample2+Total amount of (d) × 100%.
The extraction temperature of the ionic liquid was controlled at 40 ℃, the extraction time was 4 hours, the extraction pressure was 0.1MPa, and the extraction rates at different concentrations are shown in table 3.
TABLE 3 extraction rates of ionic liquids of different concentrations
| Concentration mol/L | 0.1 | 0.2 | 0.3 | 0.4 | 0.5 | 0.6 |
| Extraction rate | 48.31％ | 49.83％ | 66.42％ | 100％ | 85.20％ | 65.61％ |
The extraction rates at different extraction times are shown in Table 4, with the concentration of the ionic liquid controlled at 0.6mol/L, the extraction temperature at 40 ℃ and the extraction pressure at 0.1 MPa.
TABLE 4 Ionic liquid vs. Co at different extraction times2+Extraction rate of
| Extraction time h | 1 | 2 | 3 | 4 | 5 | 6 |
| Extraction rate | 52.99％ | 63.69％ | 71.61％ | 100％ | 100％ | 100％ |
The extraction rates at different extraction temperatures are shown in Table 5 when the concentration of the ionic liquid is controlled to be 0.6mol/L, the extraction time is 4h, and the extraction pressure is 0.1 MPa.
TABLE 5 Ionic liquid vs. Co at different extraction temperatures2+Extraction rate of
| The extraction temperature is lower | 10 | 20 | 30 | 40 | 50 | 60 |
| Extraction rate | 60.03％ | 63.21％ | 70.49％ | 100％ | 100％ | 100％ |
By the ionic liquid to Co under different conditions2+Preliminarily determining the extraction conditions of the ionic liquid: the extraction pressure is 0.1MPa, the extraction concentration is 0.4mol/L, the extraction temperature is 40 ℃, and the extraction time is 4 hours.
Under the extraction conditions, 0.4mol/L of the glycolic acid/alanine natural eutectic ionic liquid pair Co is detected2+The extraction capacity of (D) was 2.8g/100 mL. Co2+The extraction capacity of (a) is calculated as follows:
c-extraction capacity, g/mL;
V1-volume of 100mL ionic liquid, mL;
V2volume of ionic liquid added during extraction, mL;
m-addition of CoCl2·6H2Amount of O, g;
m-addition of CoCl2·6H2Relative molecular mass of O;
M2-Co2+relative molecular mass of (a);
m2-the amount of the simulated waste sample added during extraction, g;
m1this experiment Co2+The amount of the waste sample, g, was simulated.
Example 3
Utilizing glycolic acid and alanine of example 1The molar ratio of the eutectic ionic liquid to the heavy metal Pb in the mining waste residue is 4:12+The extraction test was carried out as follows:
preparation of Pb as in example 22+Waste samples, i.e. in Pb2+Adding 5g of silica gel into the solution, uniformly stirring the solution in a magnetic stirrer, stirring the solution for 10 hours, then rotationally evaporating the solution under the vacuum condition, finally putting the solution into an oven, and drying the solution at 120 ℃ for 12 hours until the weight of the solution is constant, wherein the solution is used as Pb in the experiment2+And simulating a waste residue sample.
Pb in a configuration of 1g/L2+Diluting the standard solution by 12.5 times, 25 times, 50 times, 100 times and 200 times respectively, and determining by anodic stripping voltammetry to obtain Pb2+The standard curve of (2).
Preparing the ionic liquid and ultrapure water into an ionic liquid aqueous solution with the concentration of 0.4mol/L, taking out 20mL of the ionic liquid aqueous solution, putting the ionic liquid aqueous solution into a 100mL round-bottom flask, adding 3g of a simulated waste residue sample, stirring at 40 ℃ for 4h to perform an extraction experiment, centrifuging at the rotating speed of 3500r/min for 15min by using a low-speed centrifuge, taking the supernatant, storing, diluting the supernatant, and measuring Pb by using an anodic voltammetry to measure Pb2+To thereby calculate Pb2+The extraction rate of (2).
Through detection, the ionic liquid is used for treating Pb under the conditions that the concentration of the ionic liquid is 0.4mol/L, the extraction temperature is 40 ℃ and the extraction time is 4 hours2+The extraction rate of (D) was 83.17%.
Comparative example 1
Ionic liquids were prepared by the method of example 1 using glycolic acid and glycine, and glycolic acid and proline, respectively, at a molar ratio of 4:1, and then ultrapure water was added thereto to prepare glycolic acid/glycine and glycolic acid/proline ionic liquid aqueous solutions having a concentration of 0.4mol/L, and alanine was prepared as an aqueous solution of 0.4mol/L, and Co was carried out by the method of example 2 using ultrapure water as a control2+Extracting. Simultaneously preparing the disclosed acetamide/alanine ionic liquid and acetamide/citric acid ionic liquid into 0.4mol/L aqueous solution, and carrying out the same Co2+Extraction test of (2). The extraction results are shown in Table 7.
Table 7 different solutions for Co2+Extraction rate of
As is clear from the extraction results in Table 7, the above-mentioned glycolic acid/alanine eutectic ionic liquid pairs of Co2+The extraction rate of the eutectic ionic liquid can reach 100 percent in a single time, and other ionic liquids can not reach the Co pair of the glycolic acid/alanine eutectic ionic liquid2+The effect of extraction.
Meanwhile, the glycolic acid/alanine natural eutectic ionic liquid is used for treating metal Co in mining waste residues2+And Co in other solid wastes2+The same applies.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents or improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (9)
1. A glycolic acid/alanine natural eutectic ionic liquid is characterized in that: is prepared from glycolic acid and alanine.
2. The glycolic acid/alanine natural eutectic ionic liquid of claim 1, characterized by: the molar ratio of glycolic acid to alanine was 4: 1.
3. A method for preparing a glycolic acid/alanine natural eutectic ionic liquid according to claim 1 or 2, characterized in that: mixing said glycolic acid and said alanine and grinding to a solid powder, in N2And under protection, heating the solid powder to 78-82 ℃ for reaction until a transparent uniform liquid is formed, and drying the liquid to obtain the glycolic acid/alanine natural eutectic ionic liquid.
4. A method of preparing a glycolic acid/alanine natural eutectic ionic liquid as claimed in claim 3, characterized in that: the drying method is vacuum drying, and the drying time is 15-25 h.
5. Use of the glycolic acid/alanine natural eutectic ionic liquid according to claim 1 or 2 as a heavy metal ion extractant.
6. The use of claim 5, wherein: the heavy metal ions are divalent cobalt ions.
7. The use of claim 5, wherein: the heavy metal ions are divalent lead ions.
8. The method for extracting heavy metal ions by using the glycolic acid/alanine natural eutectic ionic liquid as claimed in claim 1 or 2, characterized in that: dissolving the glycolic acid/alanine natural eutectic ionic liquid in water to enable the concentration of the glycolic acid/alanine natural eutectic ionic liquid to reach 0.1-0.6 mol/L, adding a sample to be extracted, and then extracting for 1-6h at the pressure of 0.08-0.12MPa and the temperature of 10-60 ℃.
9. The method for extracting heavy metal ions by using the glycolic acid/alanine natural eutectic ionic liquid as claimed in claim 8, wherein: dissolving the glycolic acid/alanine natural eutectic ionic liquid in water to enable the concentration of the glycolic acid/alanine natural eutectic ionic liquid to reach 0.4mol/L, adding a sample to be extracted, and extracting for 4h at the pressure of 0.1MPa and the temperature of 40 ℃.
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| WO2001056933A2 (en) * | 2000-02-04 | 2001-08-09 | Commodore Separation Technologies, Inc. | Combined supported liquid membrane/strip dispersion processes and extractants |
| US6410036B1 (en) * | 2000-05-04 | 2002-06-25 | E-L Management Corp. | Eutectic mixtures in cosmetic compositions |
| JP2006042613A (en) * | 2004-07-30 | 2006-02-16 | San Akuteisu:Kk | Method for producing harmful heavy metal-eliminated food material |
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| US20190262647A1 (en) * | 2016-07-29 | 2019-08-29 | Tyco Fire Products Lp | Firefighting foam compositions containing deep eutectic solvents |
| WO2021034150A1 (en) * | 2019-08-21 | 2021-02-25 | 주식회사 엘지생활건강 | Cosmetic composition comprising eutectic mixture |
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| WO2001056933A2 (en) * | 2000-02-04 | 2001-08-09 | Commodore Separation Technologies, Inc. | Combined supported liquid membrane/strip dispersion processes and extractants |
| US6410036B1 (en) * | 2000-05-04 | 2002-06-25 | E-L Management Corp. | Eutectic mixtures in cosmetic compositions |
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| CN102689922A (en) * | 2011-03-24 | 2012-09-26 | 杨春晓 | Lead compound nano-powder preparation method for recovery and manufacture of lead-acid battery |
| US20190262647A1 (en) * | 2016-07-29 | 2019-08-29 | Tyco Fire Products Lp | Firefighting foam compositions containing deep eutectic solvents |
| WO2021034150A1 (en) * | 2019-08-21 | 2021-02-25 | 주식회사 엘지생활건강 | Cosmetic composition comprising eutectic mixture |
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