CN115572236A - Choline lactic acid ionic liquid, preparation method thereof and application thereof in iodine extraction - Google Patents
Choline lactic acid ionic liquid, preparation method thereof and application thereof in iodine extraction Download PDFInfo
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- CN115572236A CN115572236A CN202211407459.4A CN202211407459A CN115572236A CN 115572236 A CN115572236 A CN 115572236A CN 202211407459 A CN202211407459 A CN 202211407459A CN 115572236 A CN115572236 A CN 115572236A
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- choline
- ionic liquid
- lactic acid
- iodine
- collecting
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 65
- 229960001231 choline Drugs 0.000 title claims abstract description 47
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 46
- 239000004310 lactic acid Substances 0.000 title claims abstract description 46
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 title claims abstract description 41
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 239000011630 iodine Substances 0.000 title claims abstract description 29
- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 29
- 238000000605 extraction Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 6
- -1 hydroxyl choline Chemical compound 0.000 claims abstract description 6
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 5
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 5
- 229960003178 choline chloride Drugs 0.000 claims abstract description 5
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 5
- 238000001514 detection method Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000008367 deionised water Substances 0.000 claims abstract description 4
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 4
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 4
- 101710134784 Agnoprotein Proteins 0.000 claims abstract description 3
- 238000001291 vacuum drying Methods 0.000 claims abstract description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- MIFGTXFTLQVWJW-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;2-hydroxypropanoate Chemical compound CC(O)C([O-])=O.C[N+](C)(C)CCO MIFGTXFTLQVWJW-UHFFFAOYSA-M 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229940075419 choline hydroxide Drugs 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/13—Iodine; Hydrogen iodide
- C01B7/14—Iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/08—Lactic acid
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of ionic liquid, in particular to choline lactic acid ionic liquid, a preparation method thereof and application thereof in iodine extraction. The choline lactic acid ionic liquid has a structural formula shown as (I), and the preparation method comprises the following steps: placing choline chloride in a container filled with deionized water, completely dissolving, pouring into hydroxide type anion exchange resin, collecting eluate, and collecting with AgNO 3 ‑HNO 3 Detecting the solution until the detection solution is precipitated or turbid, and stopping collecting; adding lactic acid into the exchanged hydroxyl choline, stirring and reacting at room temperature, performing rotary evaporation to remove water, and performing vacuum drying to obtain the target ionic liquid choline lactic acid. The choline lactic acid ionic liquid is simple to operate, low in cost, high in purity and strong in stability, is a green environment-friendly ionic liquid, and has a good extraction effect on iodine.
Description
Technical Field
The invention relates to the technical field of ionic liquid, in particular to choline lactic acid ionic liquid, a preparation method thereof and application thereof in iodine extraction.
Background
The ionic liquid is salt with melting point lower than 100 ℃, is formed by combining organic cation and organic or inorganic anion, and has the properties of low vapor pressure, physical and chemical stability and the like. They are designed to have good stability under a variety of reaction conditions and thus are basic chemicals for reaction solvents, battery electrolytes, lubricants, surfactants, catalysts, and the like. Choline as ionic liquid cation has positive influence on biodegradability, and belongs to environment-friendly ionic liquid.
With the development and utilization of nuclear energy, radioactive iodine occupies a large amount of components in radioactive contamination due to nuclear radiation contamination caused by nuclear leakage and the like, and can seriously harm the health of people. Therefore, it is necessary to research an efficient adsorbent for capturing iodine, and choline lactic acid is an environment-friendly ionic liquid, which is very useful for iodine extraction.
The research on the ionic liquid at the present stage is not so perfect, and the new ionic liquid is continuously developed.
Disclosure of Invention
Aiming at the problems, the invention provides the choline lactic acid ionic liquid which has the advantages of simple operation, low cost, high purity and strong stability.
In order to achieve the purpose, the technical scheme of the invention is as follows: a choline lactic acid ionic liquid has a structural formula shown as (I):
the preparation method of the choline lactic acid ionic liquid is characterized by comprising the following steps:
1) Placing choline chloride in a container filled with deionized water, completely dissolving, pouring into hydroxide type anion exchange resin, collecting eluate, and collecting with AgNO 3 -HNO 3 Detecting the solution until the detection solution is precipitated or turbid, and stopping collecting;
2) Adding lactic acid into the exchanged hydroxyl choline, stirring and reacting at room temperature, performing rotary evaporation to remove water, and performing vacuum drying to obtain target ionic liquid choline lactic acid;
in the preparation method of the choline lactate ionic liquid, in the step 2), the molar ratio of the hydroxyl choline: lactic acid =1:1.
In the preparation method of the choline lactic acid ionic liquid, in the step 2), the stirring reaction time is 48 hours.
The application of the choline lactic acid ionic liquid in iodine extraction.
The application method comprises the following steps of putting the choline lactic acid ionic liquid into a container, heating and stirring the choline lactic acid ionic liquid to enable the choline lactic acid ionic liquid to form a film at the bottom of the container, adding a cyclohexane solution of iodine, and carrying out extraction and separation on the iodine.
The invention has the beneficial effects that: the choline lactic acid ionic liquid is simple to operate, low in cost, high in purity and strong in stability, is a green environment-friendly ionic liquid, has a good extraction effect on iodine, and has a good prevention and treatment effect on influence and harm of radioactive iodine on environment and human.
Drawings
Figure 1 is a hydrogen spectrum of the choline lactic acid ionic liquid prepared in example 1.
Fig. 2 is a carbon spectrum of the choline lactic acid ionic liquid prepared in example 1.
Figure 3 is the recycle capacity of the choline lactic acid ionic liquid prepared in example 1.
Detailed Description
The invention is further illustrated by the following specific examples. The invention is not limited to the embodiments, but may be varied slightly without departing from the scope of the invention.
Example 1 Choline lactic acid Ionic liquids
The preparation method comprises the following steps:
1) Preparation of choline lactic acid ionic liquid:
97.734g choline chloride solid was weighed and dissolved completely by adding 500mL deionized water.
2) 717 anion exchange resin is taken, activated, regenerated and processed to obtain the hydroxide anion exchange resin. Loading the hydroxide anion exchange resin into a column, washing with water to neutrality, and draining. Pouring the choline chloride solution into resin, reacting for 2-4h, collecting the effluent after the reaction is finished, continuously detecting with AgNO3-HNO3 solution until the detection solution is precipitated or turbid, and stopping collection; obtaining the choline in the hydroxyl form, and immediately and rapidly calibrating. The exchange capacity of the resin is much greater than the amount of liquid moles.
3) And mixing the hydroxyl choline liquid with 40.54g of lactic acid, reacting for 48 hours at room temperature, performing rotary evaporation and drying for three days to obtain the choline lactic acid ionic liquid, wherein the yield is 85.6%, and the purity is 98%. The molar ratio of the choline hydroxide to the lactic acid is 1:1.
FIG. 1 is nuclear magnetic hydrogen spectrum of prepared ionic liquid, the characteristic peak of each hydrogen and the position of the hydrogen on the corresponding functional group of the ionic liquid are shown in the figure, and the characteristic peak of the hydrogen in FIG. 1 accords with the position of the hydrogen contained in the choline lactic acid ionic liquid. FIG. 2 is nuclear magnetic carbon spectrum of the prepared ionic liquid, the characteristic peak of each carbon and the position of the corresponding ionic liquid carbon are shown in the figure, the characteristic peak of the carbon in FIG. 2 accords with the position of each group carbon of the choline lactic acid ionic liquid, and the prepared ionic liquid is choline lactic acid ionic liquid which has a structural formula shown in formula (I),
example 2 use of choline lactic acid to extract iodine
(I) extraction separation experiment
A cyclohexane solution having an iodine concentration of 0.01moL/L was prepared in a 100mL volumetric flask, and 0.5g of choline lactic acid ionic liquid was weighed in a 250mL Erlenmeyer flask and heated under stirring to form a film of the ionic liquid on the bottom of the Erlenmeyer flask. The prepared cyclohexane solution of iodine is poured into a conical flask, and the extraction and separation experiment of iodine is carried out by magnetic stirring at the temperature of 30 ℃.
In the extraction separation experiment, the ionic liquid is adhered to the bottom of the conical flask, the supernatant is clear, and the content of iodine in the ionic liquid can be determined by detecting the concentration of iodine in the supernatant. Every 2 minutes, 200. Mu.L of cyclohexane phase solution was measured by a pipette and diluted into a 5mL volumetric flask with cyclohexane solution. Preparing a series of cyclohexane solutions of iodine with different concentrations, determining the maximum absorption wavelength of iodine at 523nm through spectral scanning, performing photometric measurement at the wavelength, and drawing a standard curve according to the change of absorbance along with the concentration.
Extraction rate of choline lactate ionic liquid to iodine
After extraction of the choline lactic acid ionic liquid, detection shows that the concentration of iodine in supernatant liquid is 0.0004744moL/L, the extraction mass ratio of the choline lactic acid ionic liquid to iodine is 1.940528, and the extraction molar ratio is iodine: choline lactate ionic liquid =1.35975578mol/mol.
(III) recoverable performance of choline lactic acid ionic liquid to iodine
To test the recoverability of the choline lactic acid ionic liquid, it was recovered after the first extraction and then reused for subsequent cycles. Ethyl acetate was used to recover the ionic liquid due to the significant difference in solubility between choline lactic acid ionic liquid and iodine in ethyl acetate. Ethyl acetate was added to the ionic liquid layer and after shaking for 30 minutes, the iodine reached equilibrium in ethyl acetate. The ethyl acetate layer was then decanted and the process repeated three times to ensure that the recovered ionic liquid was free of impurities. The same process is repeated for each cycle. And finally calculating the iodine removal efficiency to evaluate the extraction capacity of the recovered ionic liquid. Figure 3 shows that the recovered ionic liquid can be reused times and that the iodine removal performance remains substantially unchanged after 5 cycles. However, the efficiency gradually decreased after 6 cycles, but the efficiency remained at about 90%.
Claims (6)
1. A choline lactate ionic liquid having the formula (I):
2. the preparation method of choline lactic acid ionic liquid as claimed in claim 1, characterized by comprising the following steps:
1) Placing choline chloride in a container filled with deionized water, dissolving completely, pouring into hydroxide type anion exchange resin, collecting eluate, and collecting with AgNO 3 -HNO 3 Detecting the solution until the detection solution is precipitated or turbid, and stopping collecting;
2) Adding lactic acid into the exchanged hydroxyl choline, stirring and reacting at room temperature, performing rotary evaporation to remove water, and performing vacuum drying to obtain the target ionic liquid choline lactic acid.
3. The method for preparing choline lactate ionic liquid according to claim 2, wherein in the step 2), the ratio of hydroxyl choline: lactic acid =1:1.
4. The method for preparing choline lactic acid ionic liquid according to claim 2, wherein the stirring reaction time in step 2) is 48 hours.
5. The use of a choline lactic acid ionic liquid according to claim 1 for the extraction of iodine.
6. The use according to claim 5, wherein the method comprises placing the choline lactic acid ionic liquid as described in claim 1 in a container, heating and stirring to form a film on the bottom of the container, adding a cyclohexane solution of iodine, and performing extraction separation of iodine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211407459.4A CN115572236A (en) | 2022-11-10 | 2022-11-10 | Choline lactic acid ionic liquid, preparation method thereof and application thereof in iodine extraction |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211407459.4A CN115572236A (en) | 2022-11-10 | 2022-11-10 | Choline lactic acid ionic liquid, preparation method thereof and application thereof in iodine extraction |
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| CN115572236A true CN115572236A (en) | 2023-01-06 |
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| CN202211407459.4A Pending CN115572236A (en) | 2022-11-10 | 2022-11-10 | Choline lactic acid ionic liquid, preparation method thereof and application thereof in iodine extraction |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1854120A (en) * | 2004-12-06 | 2006-11-01 | 河北师范大学 | Non-toxic ion liquid its production and use |
| CN103613573A (en) * | 2013-11-11 | 2014-03-05 | 河南师范大学 | Method for synthesizing coumarin and derivatives thereof under catalysis of choline ionic liquids |
| CN105949240A (en) * | 2016-05-13 | 2016-09-21 | 河南师范大学 | Method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of ionic liquid |
| CN109464661A (en) * | 2018-12-14 | 2019-03-15 | 中国科学院过程工程研究所 | A kind of vaccine antigen composition and preparation method thereof |
| CN110540508A (en) * | 2019-08-30 | 2019-12-06 | 齐鲁工业大学 | Eutectic solvent and application thereof in extracting lignin |
| CN111606814A (en) * | 2020-04-28 | 2020-09-01 | 廊坊师范学院 | Ionic liquid containing citrazinic acid anions and application thereof in iodine absorption |
-
2022
- 2022-11-10 CN CN202211407459.4A patent/CN115572236A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1854120A (en) * | 2004-12-06 | 2006-11-01 | 河北师范大学 | Non-toxic ion liquid its production and use |
| CN103613573A (en) * | 2013-11-11 | 2014-03-05 | 河南师范大学 | Method for synthesizing coumarin and derivatives thereof under catalysis of choline ionic liquids |
| CN105949240A (en) * | 2016-05-13 | 2016-09-21 | 河南师范大学 | Method for synthesizing 4-phosphonic acid-1,5-substituted-1,2,3 triazole compounds through catalysis of ionic liquid |
| CN109464661A (en) * | 2018-12-14 | 2019-03-15 | 中国科学院过程工程研究所 | A kind of vaccine antigen composition and preparation method thereof |
| CN110540508A (en) * | 2019-08-30 | 2019-12-06 | 齐鲁工业大学 | Eutectic solvent and application thereof in extracting lignin |
| CN111606814A (en) * | 2020-04-28 | 2020-09-01 | 廊坊师范学院 | Ionic liquid containing citrazinic acid anions and application thereof in iodine absorption |
Non-Patent Citations (1)
| Title |
|---|
| 李瑞鹏: "胆碱类离子液体对苯酚和碘的萃取与捕集性能研究", 河南师范大学硕士学位论文, 31 May 2018 (2018-05-31), pages 59 - 77 * |
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