JP2007327085A5 - - Google Patents
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- JP2007327085A5 JP2007327085A5 JP2006157842A JP2006157842A JP2007327085A5 JP 2007327085 A5 JP2007327085 A5 JP 2007327085A5 JP 2006157842 A JP2006157842 A JP 2006157842A JP 2006157842 A JP2006157842 A JP 2006157842A JP 2007327085 A5 JP2007327085 A5 JP 2007327085A5
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- rare earth
- earth metal
- extractant
- aqueous solution
- alkyl group
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- 229910052761 rare earth metal Inorganic materials 0.000 claims description 24
- 150000002910 rare earth metals Chemical class 0.000 claims description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000008079 hexane Substances 0.000 claims description 11
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 210000002356 Skeleton Anatomy 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- SEGLCEQVOFDUPX-UHFFFAOYSA-N Di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000002194 synthesizing Effects 0.000 description 4
- 230000037408 Distribution ratio Effects 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 2
- NDSYZZUVPRGESW-UHFFFAOYSA-N 2-(2-octoxyethoxy)ethanol Chemical compound CCCCCCCCOCCOCCO NDSYZZUVPRGESW-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052773 Promethium Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- -1 carboxylic acid compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002634 lipophilic molecules Chemical class 0.000 description 1
- 238000011068 load Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002285 radioactive Effects 0.000 description 1
Description
本願発明では、第一に、無極性アルカン系有機溶媒にDGAAの骨格を有する次式： In the present invention, first, the following formula having a DGAA skeleton in a nonpolar alkane-based organic solvent :
で表されるDGAAが溶解している溶液であることを特徴とする希土類金属の抽出剤を提供し、第二に、無極性アルカン系有機溶媒がヘキサンである前記の希土類金属の抽出剤を提供する。DGAA骨格にアルキル鎖を導入して、親油性を付与した化合物を無極性アルカン系有機溶媒に溶解した溶液を抽出剤として希土類金属の抽出に活用することができ、しかも、DGAA骨格にアルキル鎖を導入した化合物は、1段階の合成反応によって、容易かつ高収率で合成することができ、低コストでの生産が可能な抽出剤となる。この抽出剤によれば、第三には、抽出すべき希土類金属を含む水溶液を、上記の抽出剤と適度な酸性条件下、すなわち従来のDGA骨格の化合物を用いる場合に比べてより低い酸濃度であるpHが1〜3程度、望ましくはpH4までの範囲の酸性条件下で接触させることで有機相である抽出剤に希土類金属を抽出し、分液した有機相を、前記水溶液よりも酸の濃度を高くした別の水溶液と接触させることで別の水溶液に希土類金属を逆抽出することを特徴とする希土類金属の抽出方法を提供する。
Providing extractant rare earth metals, wherein the solution der Rukoto THAT represented DGAA is dissolved, the second, the extractant of the rare earth metal nonpolar alkane-based organic solvent is hexane To provide . A solution in which an alkyl chain is introduced into a DGAA skeleton and a lipophilic compound is dissolved in a non-polar alkane organic solvent can be used for extraction of rare earth metals as an extractant, and an alkyl chain is added to the DGAA skeleton. The introduced compound can be synthesized easily and with high yield by a one-step synthesis reaction, and becomes an extractant that can be produced at low cost. According to this extractant, thirdly , the aqueous solution containing the rare earth metal to be extracted has a lower acid concentration as compared with the above extractant and moderately acidic conditions, that is, when a conventional DGA skeleton compound is used. The rare earth metal is extracted into the extractant that is an organic phase by contacting under acidic conditions with a pH of about 1 to 3, preferably up to pH 4, and the separated organic phase is more acidic than the aqueous solution . Provided is a method for extracting a rare earth metal, wherein the rare earth metal is back-extracted into another aqueous solution by contacting with another aqueous solution having a high concentration.
DGAAの骨格を有し、その窒素原子に二つの同一もしくは別異のアルキル基を導入した化合物（以下、これらを総じてRDGAAと省略する）を合成する際は、アミンとジグリコール酸の縮合反応を用い、活性化した酸成分として酸無水物の無水ジグリコール酸を用いる。また、対称酸無水物を用いれば、酸の半分はアミンと反応しない利点もある。つまり、次式： When synthesizing a compound having a DGAA skeleton and introducing two identical or different alkyl groups into the nitrogen atom (hereinafter collectively referred to as RDGAA), a condensation reaction of amine and diglycolic acid is performed. An acid anhydride diglycolic acid anhydride is used as the activated acid component. In addition, if a symmetric acid anhydride is used, there is an advantage that half of the acid does not react with the amine. That is, the following formula:
本願発明の抽出剤に含まれる前記の一般式で表されるジグリコールアミド酸においては、R1およびR2のアルキル基の少なくともいずれか一方は炭素数6以上のアルキル基であるが、一般的には炭素数は6〜18、より好ましくは7〜12が考慮される。炭素数が6未満の場合には親油性が十分でなく、水相への溶解が無視できなくなる。また、炭素数が過剰に大きい場合にはその製造がコスト高になるとともに抽出能そのものの向上には寄与しないことになる。なお、R1およびR2については親油性が確保される限り、一方が炭素数6以上であれば他方は6未満であってもよいが、製造上、そして安全性の観点からは、いずれも炭素数 6以上のもので、さらには同数であることが好適に考慮される。 In diglycol amic acid represented by the general formula that is part of the extracting agent of the present invention, although at least one of the alkyl groups R 1 and R 2 are alkyl group having 6 or more carbon atoms, generally Specifically, 6 to 18 carbon atoms, more preferably 7 to 12 carbon atoms are considered. When the number of carbon atoms is less than 6, the lipophilicity is not sufficient and dissolution in the aqueous phase cannot be ignored. Further, when the carbon number is excessively large, the production becomes expensive and does not contribute to the improvement of the extraction ability itself. As long as one of R 1 and R 2 is oleophilic, if one of them has 6 or more carbon atoms, the other may be less than 6, but from the viewpoint of production and safety, both It is preferably considered that the number of carbon atoms is 6 or more and the same number.
（実施例）
ジグリコールアミド酸骨格にアルキル基を導入した化合物の合成方法
ヘキサンなどのアルカン系無極性有機溶媒に可溶な化合物を調製するため、ジグリコールアミド酸（DGAA）の骨格（＞N−CO−CH2−O−CH2−COOH）の窒素原子に親油性の高いアルキル基を導入する。これまでの研究から、少なくとも一方のアルキルが、炭素原子を6個以上有することによって、抽出剤として十分な親油性を付加できることがわかっている。ここでは、炭素数8のアルキル基を2つ持つジオクチルジグリコールアミド酸（DODGAA）の合成法を例として示す。反応式は以下に示す通りである。
( Example )
Method for synthesizing compounds in which alkyl group is introduced into diglycolamide acid skeleton Diglycolamide (DGAA) skeleton (> N-CO-CH 2- O—CH 2 —COOH) introduces a highly lipophilic alkyl group into the nitrogen atom. Previous studies have shown that at least one alkyl can have sufficient lipophilicity as an extractant by having 6 or more carbon atoms. Here, as examples synthesis of two lifting Tsuji octyl diglycol amic acid alkyl group having 8 carbon atoms (DODGAA). The reaction formula is as shown below.
このように、DODGAAは1つの化学反応のみで容易に合成でき、精製も容易なので、製造に要するコストが安価である。
DODGAAを用いた希土類金属の抽出・分離
合成したDODGAAを用いて希土類金属の抽出・分離実験を行った。具体的には、DODGAAをヘキサンに溶解して0.03M DODGAAヘキサン溶液を調製し、以下に示すような希土類金属に対する2つの抽出実験を行った。
Thus, DODGAA can be easily synthesized by only one chemical reaction and can be easily purified, so that the cost required for production is low.
Extraction and separation of rare earth metals using DODGAA
Rare earth metal extraction / separation experiments were conducted using synthesized DODGAA . Specifically, 0.03M DODGAA hexane solution was prepared by dissolving DODGAA in hexane, and two extraction experiments for rare earth metals as shown below were conducted.
（抽出実験１）DODGAAヘキサン溶液の抽出能
希土類金属としてユウロピウムを選び、分配比（有機相に抽出された金属の濃度を水相に残った金属の濃度で割った値）の水相中の酸濃度に対する依存を測定した。その要領は以下の通りである。
(Extraction experiment 1) Extraction ability of DODGAA hexane solution Select europium as the rare earth metal, and partition ratio (the concentration of the metal extracted into the organic phase divided by the concentration of the metal remaining in the aqueous phase) in the aqueous phase The dependence on concentration was measured. The procedure is as follows.
（抽出実験２）DODGAAヘキサン溶液の選択的分離能
14種の希土類金属（放射性のプロメチウムを除くすべての希土類金属）について、水相中の酸濃度を一定（pH=1.5）にして、（抽出実験１）と同じ0.03MのDODGAAを含む有機相を用いて抽出操作を行い、同様の要領でそれぞれの希土類金属の分配比を測定した。なお、選択的分離能を比較するため、一例として、軽ランタノイドからの分離という観点でランタンを代表として選び、ランタンからの分離係数（対象とする希土類金属（ランタノイド：Ln）の分配比（DLn(III)）をランタンの分配比（DLa(III)）で割った値）として結果をまとめた。
(Extraction experiment 2) Selective resolution of DODGAA hexane solution
For the 14 rare earth metals (all rare earth metals except radioactive promethium), the organic phase containing 0.03M DODGAA is the same as (Extraction Experiment 1) with the acid concentration in the aqueous phase kept constant (pH = 1.5). The extraction operation was performed, and the distribution ratio of each rare earth metal was measured in the same manner. In order to compare the selective resolution, as an example, lanthanum was selected as a representative from the viewpoint of separation from light lanthanoids, and the separation factor from lanthanum (target rare earth metal (lanthanoid: Ln) distribution ratio (D Ln The results are summarized as (III) ) divided by the lanthanum distribution ratio (D La (III) ).
この結果から、DODGAAヘキサン溶液の選択的分離能は、軽希土についてはPC88Aヘキサン溶液及びD2EHPAヘキサン溶液に勝り、重希土についてはPC88Aヘキサン溶液及びD2EHPAヘキサン溶液に劣ることがわかる。
DODGAAの水への溶解度の測定
合成したDODGAAの水への溶解度を測定した。過剰量のDODGAAを水（純水）に投入し、30分間振とう、さらに室温で1日以上放置した後、遠心分離を2回行ってから水溶液を分取し、水に溶解したDODGAAの濃度を紫外部の吸光度に基づいて決定した。
From this result, the selective separation capability of DODGAA hexane solution For the light rare earth better than PC88A hexane solution and D2EHPA hexane solution, for the heavy rare earths inferior to PC88A hexane solution and D2EHPA hexane.
Measuring the solubility of DODGAA in water
The solubility of synthesized DODGAA in water was measured. Add an excess amount of DODGAA to water (pure water), shake for 30 minutes, and leave it at room temperature for more than 1 day, then centrifuge twice and separate the aqueous solution. The concentration of DODGAA dissolved in water Was determined based on the absorbance in the ultraviolet region.
以上の実施例、比較例により、C、H、O、Nのみからなる完全焼却処分が可能である化合物（たとえばDODGAA）を用いて、希土類金属の抽出を行った結果、完全焼却処分が可能な既存のカルボン酸系化合物（Versatic 10）を大きく上回る抽出能・選択的分離能を示すとともに、完全焼却処分はできないが非常に高性能なリン系化合物（PC88A、D2EHPA）にも劣らないことが明らかになった。さらに、水に対する前記化合物の溶解度が、これら既存の化合物（PC88A、D2EHPA、Versatic 10）と比較して著しく小さいため、水環境への前記化合物の負荷を大幅に低減することが可能である。また、水への溶解度が著しく小さいことは、有機相の繰り返し利用に伴う前記化合物の損失も著しく小さくなり、前記化合物を頻繁に補充する必要がなくなるため、経済的である。なお、DODGAAの合成及び精製は非常に容易であるため、製造に要するコストも安価である。また、本願発明で提案する希土類金属の抽出法によって、pH を調節することで容易に有機相への抽出、水相への逆抽出を可能にし、そのpHの領域では、腐食が少なくリサイクル効率に優れた硝酸を用いることが可能であり、抽出工程が安価である。 As a result of extracting rare earth metals using a compound (for example, DODGAA) consisting of only C, H, O, and N according to the above examples and comparative examples, complete incineration is possible. It is clear that the extractability and selective separation ability greatly exceed the existing carboxylic acid compounds (Versatic 10), and it is not inferior to the very high performance phosphorus compounds (PC88A, D2EHPA) although it cannot be completely incinerated. Became. Furthermore, since the solubility of the compound in water is significantly smaller than these existing compounds (PC88A, D2EHPA, Versatic 10), it is possible to greatly reduce the load of the compound on the water environment. In addition, the extremely low solubility in water is economical because the loss of the compound due to repeated use of the organic phase is remarkably reduced, and it is not necessary to replenish the compound frequently. Since synthesis and purification of DODGAA is very easy, the cost required for production is also low. In addition, the rare earth metal extraction method proposed in the present invention allows easy extraction into the organic phase and back extraction into the aqueous phase by adjusting the pH. Excellent nitric acid can be used and the extraction process is inexpensive.
Claims (3)
で表されるジグリコールアミド酸が溶解している溶液であることを特徴とする希土類金属の抽出剤。 For nonpolar alkane organic solvents
Extractant rare earth metals, wherein the solution der Rukoto that diglycol amic acid is dissolved represented in.
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| JP2006157842A JP5035788B2 (en) | 2006-06-06 | 2006-06-06 | Rare earth metal extractant and extraction method |
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| JP2006157842A JP5035788B2 (en) | 2006-06-06 | 2006-06-06 | Rare earth metal extractant and extraction method |
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| JP2007327085A JP2007327085A (en) | 2007-12-20 |
| JP2007327085A5 true JP2007327085A5 (en) | 2010-01-28 |
| JP5035788B2 JP5035788B2 (en) | 2012-09-26 |
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| WO2024155642A1 (en) | 2023-01-17 | 2024-07-25 | Texas Tech University System | Chemically enhanced electrodialysis (ceed): a universal platform for selective ion removal |
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| JP4374460B2 (en) * | 2003-10-06 | 2009-12-02 | 独立行政法人 日本原子力研究開発機構 | Method for solvent extraction of Nd (III) from aqueous nitric acid solution and extractant therefor |
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