CN113861063A - Metal ion extracting agent and synthetic method thereof - Google Patents
Metal ion extracting agent and synthetic method thereof Download PDFInfo
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- CN113861063A CN113861063A CN202111148417.9A CN202111148417A CN113861063A CN 113861063 A CN113861063 A CN 113861063A CN 202111148417 A CN202111148417 A CN 202111148417A CN 113861063 A CN113861063 A CN 113861063A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention discloses a metal ion extracting agent and a synthesis method thereof, belonging to the technical field of synthesis of extracting agents. The synthesis method of the metal ion extracting agent specifically comprises the following steps: and adding inorganic acid into the diglycol to react to obtain diglycolic acid, then adding thionyl chloride to react with diglycol acyl chloride, and then adding 2-ethylhexylamine or di-n-octylamine to react to obtain the two metal ion extracting agents. The extractant prepared by the invention has the advantages of relatively short carbon chain length, small steric hindrance, good metal combination effect and good selectivity, and is efficient and green.
Description
Technical Field
The invention relates to the technical field of synthesis of an extracting agent, in particular to a metal ion extracting agent and a synthesis method thereof.
Background
The rare earth is an important nonferrous metal and has great application value in the fields of new material development, preparation of ultrapure materials and the like. The solvent extraction has the characteristics of high separation efficiency and low energy consumption, and becomes an important means for separating and purifying the rare earth. In addition, in the nuclear fuel post-treatment, actinides with long half-life are converted into isotopes with short half-life by neutrons, but lanthanides can effectively capture neutrons, so that lanthanides and actinides in high-level radioactive waste liquid need to be separated by a solvent extraction method. The development and scientific design process flow of a novel extracting agent are two important aspects of solvent extraction, so that the exploration of an efficient and cheap extracting agent has great significance for the development of extraction chemistry.
Sulfur-containing extractants are widely used to extract some heavy metals, lanthanides, and precious metals. But the disadvantages are that the pKa value is high, the acidity of a system suitable for extraction is too low, and acidolysis is easy, so that the application is limited to a certain extent; and secondary pollution can be caused after incineration. The amide extractant has the advantages of easy synthesis, radiation resistance, complete burnout, no pollution and the like, and is a novel green environment-friendly extractant. However, the disadvantage is that the substituted amide loses its hydrogen bonding association ability and is poorly water soluble. And nitrogen atoms are not completely substituted, the extracting agent cannot fully exert the coordination effect, and the extracting capacity is general. Compared with an amide extractant, the bisamide pod ether extractant is a novel green extractant proposed in recent years, and the extractant is complexed with metal ions in a tridentate coordination mode, so that the stability of an extract is improved, and the extraction efficiency is improved, for example, the N, N, N ', N' -tetraoctyl-3-oxoglutaramide (TODGA) extractant is easy to phase separate in a system with too high acidity or too high concentration of metal ions. How to prepare an efficient and green extractant which has good combination effect with metal, good selectivity and difficult phase separation in a system with over-high acidity or over-high metal ion concentration becomes a technical problem to be solved by the technical personnel in the field.
Disclosure of Invention
The invention aims to provide a metal ion extracting agent and a synthesis method thereof, which are used for solving the problems in the prior art, and the efficient and green extracting agent with relatively short carbon chain length, small steric hindrance, good metal combination effect and good selectivity is prepared by changing raw materials and a preparation method.
In order to achieve the purpose, the invention provides the following scheme:
one of the technical schemes of the invention is as follows: a metal ion extracting agent has a structural formula shown as a formula (1) or a formula (2):
the second technical scheme of the invention is as follows: a method for synthesizing the metal ion extracting agent according to claim 1, wherein the method for synthesizing the extracting agent represented by the formula (1) comprises the following steps:
(1) adding inorganic acid into diglycol, heating and refluxing to react to obtain diglycolic acid;
(2) adding thionyl chloride into diglycolic acid prepared in the step (1) to react to obtain diglycolic acyl chloride;
(3) and (3) adding the diglycol acyl chloride prepared in the step (2) into a mixed solution of 2-ethylhexylamine and inorganic base to react to obtain the extractant shown in the formula (1).
The third technical scheme of the invention is as follows: a method for synthesizing the metal ion extracting agent according to claim 1, wherein the method for synthesizing the extracting agent represented by the formula (2) comprises the following steps:
(1) adding inorganic acid into diglycol, heating and refluxing to react to obtain diglycolic acid;
(2) adding thionyl chloride into diglycolic acid prepared in the step (1), and heating and refluxing to react to obtain diglycolic acyl chloride;
(3) and (3) adding the diglycol acyl chloride prepared in the step (2) into a mixed solution of di-n-octylamine and inorganic base to react to obtain the extractant shown in the formula (2).
Further, the step (1) specifically includes: adding inorganic acid into diglycol, heating for reaction until no gas is released, and adding diglycol for secondary heating to obtain diglycolic acid.
Further, the inorganic acid is added when the diethylene glycol is heated to 45 ℃; the inorganic acid is nitric acid; the molar concentration of the inorganic acid is 0.01 mol/L; the molar ratio of the diethylene glycol in the primary heating reaction to the diethylene glycol in the secondary heating reaction is 1: 1-1: 6; the molar mass ratio of the total molar mass of the diethylene glycol in the primary heating reaction and the secondary heating reaction to the molar mass of the inorganic acid is 1: 0.001 to 0.004.
Further, the temperature of the primary heating is 60-70 ℃; the secondary heating specifically comprises: keeping the temperature at 40-50 ℃ for 30-60 min, and then heating the mixture to 75-85 ℃ for heating reaction for 20-40 min.
Further, the molar ratio of diglycolic acid to thionyl chloride in the step (2) is 1: 3-1: 8, the heating reflux time is 4-8 h.
Further, the molar mass ratio of the diglycol acyl chloride to the 2-ethylhexylamine in the step (3) is 1: 1-1: 6; the molar mass ratio of the 2-ethylhexylamine to the inorganic base is 1: 20-1: 50.
further, the molar mass ratio of the diglycol acyl chloride to the di-n-octylamine in the step (3) is 1: 0.5-1: 5; the molar mass ratio of the di-n-octylamine to the inorganic base is 1: 60-1: 80.
further, the inorganic base in the step (3) is sodium hydroxide; the mass fraction of the inorganic base is 30%.
The invention discloses the following technical effects:
the metal ion extracting agent prepared by the invention overcomes the defects that the existing extracting agent is not green enough, is environment-friendly, has a common extracting effect and is easy to form multi-phase separation in a system with large acidity, has the advantages of relatively short carbon chain length, small steric hindrance and the like, and is good in combination effect with metal, good in selectivity and high in extracting efficiency, thereby being a green extracting agent.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without creative efforts.
FIG. 1 is a scheme showing the synthesis scheme of example 1 of the present invention, wherein 1 is nitric acid, 2 is thionyl chloride, and 3 is 2-ethylhexylamine;
FIG. 2 shows the preparation of N, N, N ', N' -tetra-2-ethylhexyldiglycolamide according to example 1 of the present invention1A HNMR spectrogram;
FIG. 3 shows the preparation of N, N, N ', N' -tetraoctyl diglycol amide obtained in example 2 of the present invention1HNMR spectrogram.
Detailed Description
Reference will now be made in detail to various exemplary embodiments of the invention, the detailed description should not be construed as limiting the invention but as a more detailed description of certain aspects, features and embodiments of the invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Further, for numerical ranges in this disclosure, it is understood that each intervening value, between the upper and lower limit of that range, is also specifically disclosed. Every smaller range between any stated value or intervening value in a stated range and any other stated or intervening value in a stated range is encompassed within the invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference herein for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the present disclosure without departing from the scope or spirit of the disclosure. Other embodiments will be apparent to those skilled in the art from consideration of the specification. The specification and examples are exemplary only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are open-ended terms that mean including, but not limited to.
Example 1
The synthesis method of the N, N, N ', N' -tetra-2-ethylhexyl diglycol amide comprises the following steps:
(1) adding 1.0g (0.0094mol) of diethylene glycol into a clean beaker, heating to 45 ℃, adding 15mL of nitric acid with the molar concentration of 0.01mol/L, and heating to 65 ℃ to react until NO Nitrogen Oxide (NO) exists2) After the release is finished, cooling to 45-50 ℃, and slowly adding 4.9g (0.0462mol) of diethylene glycol for 1 h; after the loading of the diglycol is finished, the temperature is kept for 40min at 45 ℃, then the temperature is increased to 80 ℃ for reaction for 30min, after the reaction is finished, the solvent is removed under vacuum at 70 ℃, a dean-Stark water separator and benzene are used for azeotropic distillation to dry the residue, and then the product is filtered and recrystallized from an acetone-benzene mixture to obtain diglycolic acid with the yield of 92%.
(2) 25g (0.187mol) diglycolic acid was added to a drying flask, 85mL (about 139.23g, 1.17mol) of thionyl chloride was added and immediately heated to reflux and the reaction was stirred at that temperature for 5h, after the reaction was completed, excess thionyl chloride was distilled off under reduced pressure at 85 ℃, then high vacuum was applied at room temperature until the mixture precipitated, the precipitate was obtained by filtration, and the precipitate was distilled under high vacuum at 40 ℃ and elevated temperature until all diglycolic acid chloride liquid was collected, with a yield of 95%.
(3) Adding 0.83g (0.0064mol) of 2-ethylhexylamine and 30mL of 30% NaOH solution into a drying flask, cooling to 0 ℃, keeping the temperature unchanged, dropwise adding a diethylene glycol acyl chloride ether solution (the diethylene glycol acyl chloride ether solution contains 0.85g (0.005mol) of diethylene glycol acyl chloride) for 30min, stirring and reacting for 2h at 0 ℃ after dropwise adding is finished, standing for layering, adding a saturated NaCl solution into a water phase, cleaning, and extracting with ether to recover unreacted diethylene glycol acyl chloride; the organic phase was mixed with 20mL of 10% aqueous HCl, vigorously shaken to promote the formation of ammonium salt agglomerates, and the ammonium salt agglomerates were washed twice with 10% aqueous HCl and then with a glass frit(G3) Filtering to obtain filtrate, adding 25mL of 4% by weight aqueous solution of poly (4-styrenesulfonic acid) into the filtrate, shaking vigorously for 10min (to promote formation of polymer salt as amorphous material floating between layers), washing with distilled water to remove reacted poly (4-styrenesulfonic acid), and collecting the organic solution with MgSO4Drying and subsequent removal of the solvent by evaporation in vacuo afforded N, N, N ', N' -tetra-2-ethylhexyldiglycolamide (TEDGA) according to1HNMR spectroscopy (see FIG. 2) revealed that the purity was 97% or more and the yield was 94%.
The reaction scheme is shown in figure 1; in the figure, 1 is nitric acid, 2 is thionyl chloride and 3 is 2-ethylhexylamine.
Example 2
The synthesis method of the N, N, N ', N' -tetraoctyl diglycol amide comprises the following steps:
the same as example 1 except that N, N, N ', N' -Tetraoctyldiglycolamide (TODGA) was prepared by replacing 2-ethylhexylamine in the step (3) with 0.83g (0.0034mol) of di-N-octylamine1HNMR spectroscopy (see FIG. 3) revealed a purity of 97% or more and a yield of 91%.
Example 3
The synthesis method of the N, N, N ', N' -tetra-2-ethylhexyl diglycol amide comprises the following steps:
the difference from example 1 is that step (1) is to add 1.0g (0.0094mol) of diethylene glycol into a clean beaker, raise the temperature to 45 ℃, add 15mL of nitric acid with a molar concentration of 0.1mol/L, and then heat to 60 ℃ to react until NO Nitrogen Oxide (NO) is generated2) After the release is finished, cooling to 45-50 ℃, and slowly adding 4.9g (0.0462mol) of diethylene glycol for 1 h; after the addition of diethylene glycol was completed, the reaction was continued at 40 ℃ for 40min, then heated to 85 ℃ for 20min, after the reaction was completed, the solvent was removed under vacuum at 70 ℃, the residue was dried by azeotropic distillation with benzene using a dean-Stark trap, and then the product was filtered and recrystallized from an acetone-benzene mixture to yield diethylene glycol at 73% yield.
Example 4
The synthesis method of the N, N, N ', N' -tetra-2-ethylhexyl diglycol amide comprises the following steps:
the same as example 1 except that the amount of nitric acid added in step (1) was 10mL, the yield was 65%.
Example 5
The synthesis method of the N, N, N ', N' -tetra-2-ethylhexyl diglycol amide comprises the following steps:
the same as example 1, except that the amount of sulfurous chloride added in step (2) was 60mL, the yield was 60%.
Comparative example 1
The synthesis method of the N, N, N ', N' -tetra-2-ethylhexyl diglycol amide comprises the following steps:
the difference from the example 1 is that the step (1) is to add 15mL of nitric acid with the molar concentration of 0.01mol/L into a clean beaker, heat the nitric acid to 45-50 ℃, and then slowly add 5.9g (0.0556mol) of diethylene glycol for 1 hour; after the addition of diethylene glycol was completed, the reaction was continued at 40 ℃ for 40min, then heated to 85 ℃ for 20min, after the reaction was completed, the solvent was removed under vacuum at 70 ℃, the residue was dried by azeotropic distillation with benzene using a dean-Stark trap, and then the product was filtered and recrystallized from an acetone-benzene mixture to yield diethylene glycol at 70%.
The above-described embodiments are merely illustrative of the preferred embodiments of the present invention, and do not limit the scope of the present invention, and various modifications and improvements of the technical solutions of the present invention can be made by those skilled in the art without departing from the spirit of the present invention, and the technical solutions of the present invention are within the scope of the present invention defined by the claims.
Claims (10)
1. A metal ion extracting agent is characterized in that the structural formula of the metal ion extracting agent is shown as a formula (1) or a formula (2):
2. the method for synthesizing the metal ion extracting agent according to claim 1, wherein the method for synthesizing the extracting agent represented by the formula (1) comprises the following steps:
(1) adding inorganic acid into diglycol, heating and refluxing to react to obtain diglycolic acid;
(2) adding thionyl chloride into diglycolic acid prepared in the step (1) to react to obtain diglycolic acyl chloride;
(3) and (3) adding the diglycol acyl chloride prepared in the step (2) into a mixed solution of 2-ethylhexylamine and inorganic base to react to obtain the extractant shown in the formula (1).
3. A method for synthesizing the metal ion extracting agent according to claim 1, wherein the method for synthesizing the extracting agent represented by the formula (2) comprises the following steps:
(1) adding inorganic acid into diglycol, heating and refluxing to react to obtain diglycolic acid;
(2) adding thionyl chloride into diglycolic acid prepared in the step (1), and heating and refluxing to react to obtain diglycolic acyl chloride;
(3) and (3) adding the diglycol acyl chloride prepared in the step (2) into a mixed solution of di-n-octylamine and inorganic base to react to obtain the extractant shown in the formula (2).
4. The method for synthesizing the metal ion extracting agent according to any one of claims 2 to 3, wherein the step (1) specifically comprises: adding inorganic acid into diglycol, heating for reaction until no gas is released, and adding diglycol for secondary heating to obtain diglycolic acid.
5. The synthesis method according to claim 4, wherein the inorganic acid is added when diethylene glycol is heated to 45 ℃; the inorganic acid is nitric acid; the molar concentration of the inorganic acid is 0.01 mol/L; the molar ratio of the diethylene glycol in the primary heating reaction to the diethylene glycol in the secondary heating reaction is 1: 1-1: 6; the molar mass ratio of the total molar mass of the diethylene glycol in the primary heating reaction and the secondary heating reaction to the molar mass of the inorganic acid is 1: 0.001 to 0.004.
6. The synthesis method according to claim 4, wherein the temperature of the primary heating is 60-70 ℃; the secondary heating specifically comprises: keeping the temperature at 40-50 ℃ for 30-60 min, and then heating the mixture to 75-85 ℃ for heating reaction for 20-40 min.
7. The method for synthesizing a metal ion extractant according to any one of claims 2 to 3, wherein the molar ratio of diglycolic acid to thionyl chloride in the step (2) is 1: 3-1: 8, the heating reflux time is 4-8 h.
8. The synthesis method according to claim 2, wherein the molar mass ratio of the diglycol acyl chloride to the 2-ethylhexylamine in the step (3) is 1: 1-1: 6; the molar mass ratio of the 2-ethylhexylamine to the inorganic base is 1: 20-1: 50.
9. the synthesis method according to claim 3, wherein the molar mass ratio of the diglycol acyl chloride to the di-n-octylamine in the step (3) is 1: 0.5-1: 5; the molar mass ratio of the di-n-octylamine to the inorganic base is 1: 60-1: 80.
10. the method for synthesizing a metal ion extractant according to any one of claims 2 to 3, wherein the inorganic base in the step (3) is sodium hydroxide; the mass fraction of the inorganic base is 30%.
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Cited By (1)
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| CN116555568A (en) * | 2023-05-17 | 2023-08-08 | 四川长晏科技有限公司 | Method for extracting metal ions in strong acid system |
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