CN102002590B - Application of cyclophane amide compound containing three central hydrogen bonds as extracting agent in separation of rare-earth elements - Google Patents

Application of cyclophane amide compound containing three central hydrogen bonds as extracting agent in separation of rare-earth elements Download PDF

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CN102002590B
CN102002590B CN2010105955839A CN201010595583A CN102002590B CN 102002590 B CN102002590 B CN 102002590B CN 2010105955839 A CN2010105955839 A CN 2010105955839A CN 201010595583 A CN201010595583 A CN 201010595583A CN 102002590 B CN102002590 B CN 102002590B
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cyclophane
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amide compound
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CN102002590A (en
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袁立华
钟利健
冯文
陈龙
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Sichuan University
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Abstract

The invention relates to application of a cyclophane amide compound containing three central hydrogen bonds as an extracting agent in separation of rare-earth elements, wherein, the cyclophane amide compound containing the three central hydrogen bonds is applied to the separation of the rare-earth elements. The cyclophane amide extracting agent containing the three central hydrogen bonds has single composition, good chemical stability and less consumption; the extracting agent can carry out extraction in neutral solution; the dissolubility of the extracting agent in different solvents can be adjusted through an R group; and the extracting agent further has the advantages of fast extraction speed, fast phase separation speed and the like while extracting the rare-earth elements. Therefore, the cyclophane amide containing the three central hydrogen bonds is taken as a novel extracting agent for extracting and separating the rare-earth elements has practical application prospect.

Description

The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent in separation of rare earth elements
Technical field
The present invention relates to the new purposes of one type of cyclophane amide compound, more particularly, the present invention relates to one type and contain three center hydrogen bond cyclophane amide compounds as the application of extraction agent in separation of rare earth elements.
Background technology
REE comprises the lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu) of group of the lanthanides and with closely-related two elements of 15 elements of group of the lanthanides---scandium (Sc) and yttrium (Y) be totally 17 kinds of elements; Wherein lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu) are light rare earths, and gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), scandium (Sc), yttrium (Y) are heavy rare earth element.Rare earth is important non-ferrous metal, in fields such as novel material exploitation, ultrapure material prepns extremely important value is arranged.The preparation of high-purity single rare earth is the difficult problem of current separation science.The development of extraction agent and screening are to the exploitation of extraction process and improve often decisive role; According to the analysis of sinking of the empirical rule of existing screening extraction agent and reason, explore and be applicable to that the novel extraction agent of high efficiency separation rare earth has important significance for theories and social benefit.
The research of solvent extraction technology (except that equipment) mainly comprises two aspects, the research of established technology Study on process flow and new extractant.
Be used for the isolating small molecules organic extractant of group of the lanthanides and actinium series and mainly comprise amides, Phosphorus, sulfoxide, pyrazoline ketone etc.For example: patent CN 1084574A has reported the carboxylic acid type extraction agent; Patent CN 1108309A and CN 86105043A have reported neutral organophosphorus extractant; Patent CN 1639175A has reported phosphonic amide type extraction agent (Here it is acid amides pod ethers).The amount concentration of the required extraction agent of these patents needs a large amount of extraction agents to come the extracting rare-earth element much larger than the concentration of REE.U.S. Pat 4574072 has been reported with the alkane extraction agent that contains formyl radical dimethyl phosphine oxide (CMPO) and has been extracted group of the lanthanides, but needed to add synergic reagent three normal-butyl phosphoric acid salt.Patent CN 101529528A has reported with glycol ether acid amides or Malonodiamide and has extracted group of the lanthanides, but needed to add dialkyl group monoamide or trialkylphosphate.FRP FR2810679A1 and Japanese Patent JP2002001007 have reported with glycol ether acid amides extraction agent and have extracted group of the lanthanides that this extraction agent can form the three-fold coordination structure with group of the lanthanides.Above-mentioned extraction agent can supply the coordinate atomicity limited, and extraction efficiency and selectivity etc. has limitation, and many extraction agents and extraction process can not satisfy current needs.
Employing has the extraction agent of polygamy position atom, through the synergistic effect between ligating atom or the group, can realize extracting rare-earth element effectively.Thereby containing a plurality of Sauerstoffatoms, crown ether can cooperate the formation complex compound, though there are many documents to report that crown ether can be extracted into (reference: US4726938 in the organic phase with REE from water with rare earth metal; Andrew H. Bond, MarkL. Dietz, and Renato Chiarizia, Ind.Eng.Chem.Res. 2000; 39,3442 – 3464), but only use single crown ether extraction REE, effect of extracting is not ideal; Need through adding synergic reagent to improve percentage extraction, like trichoroacetic acid(TCA), trifluoroacetic acid, beta-diketon (reference: S.V. Demin, V.I. Zhilov, A.Yu. Tsivadze to REE; V.V. Yakshin, O.M. Vilkova, Russian Journal of Inorganic Chemistry, 2009; 54,3,385 – 388; Yoshihiro Meguro, Yoshihiro Kitatsuji, Takaumi Kimura, Zenko Yoshida, Journal of Alloys and Compounds, 1998,790 – 793).U.S. Pat 6312653B1 has reported the Calixarene Derivatives of band CMPO group, utilizes acid amides to realize separating group of the lanthanides and actinoid with collaborative work of a plurality of O ligating atoms on the phosphorus.(reference: US20020002290A1 such as Beer; Paul D. Beer, Giles D. Brindley, O. Danny Fox; Alan Grieve, Mark I. Ogden, J. Chem. Soc.; Dalton Trans.; 2002,3101 – 3111) reported the Calixarene Derivatives of being with acid amides, hydroxyl and hydroxy-acid group, utilized collaborative work of a plurality of O ligating atoms on acid amides, hydroxyl and the hydroxy-acid group to realize separating group of the lanthanides and actinoid.Further searching has the new and effective group of the lanthanides of many coordinate and the actinium series extraction agent has great importance.
One type of cyclophane amide compound that contains three center hydrogen bonds can be by the chloride compounds and 4 of the m-phthalic acid that contains side chain, and 6-dimethoxy-1,3 phenylenediamine one goes on foot into ring and makes (with reference to L. H. Yuan, W. Feng; K. Yamato, A. R. Sanford, D. G. Xu, H. Guo and B. Gong; J. Am. Chem. Soc., 2004,126,11120); Perhaps by the chloride compounds of the diamines of pentamer and the m-phthalic acid that contains side chain progressively Cheng Huan make (with reference to L. Q. Yang, L. J. Zhong, K. Yamato, X. H. Zhang; W. Feng, P. C. Deng, L. H. Yuan, X. C. Zeng and B. Gong; New J. Chem., 2009,33,729 – 733).The cyclophane amide compound that this type contains three center hydrogen bonds can be used for the identification of biological organic molecule.
Summary of the invention
The present invention is directed to the shortcoming of above-mentioned extraction agent, provide one type of cyclophane amide compound that contains three center hydrogen bonds as the extraction agent that separates except that promethium light rare earths and gadolinium.
In order to realize the foregoing invention purpose, particular content of the present invention is:
The cyclophane amide compound is as the application of extraction agent in separating except that promethium light rare earths and gadolinium, and the cyclophane amide compound is the cyclophane amide compound that contains three center hydrogen bonds, and this compound has following structure:
Figure 795816DEST_PATH_IMAGE001
R is C in the formula 11-C 16Linear alkyl chain, C 8-C 12Branched alkyl chain, C 5-C 9Linear chain or C 5-C 12Side chain ether chain.
Described C 11-C 16Linear alkyl chain be undecyl chain C 11H 23, dodecyl chain C 12H 25, hexadecyl chain C 16H 33
Described C 8-C 12Branched alkyl chain be iso-octyl chain CH 2CH (CH 2CH 3) (CH 2) 3CH 3, isodecyl chain CH 2CH (CH 2CH 3) (CH 2) 5CH 3, Permethyl 99A. base chain CH 2CH (CH 2CH 3) (CH 2) 7CH 3
Described C 5-C 9The linear chain be diethylene glycol monomethyl ether chain (CH 2CH 2O) 2OCH 3, triethylene glycol monomethyl ether chain (CH 2CH 2O) 3OCH 3, TEG monomethyl ether chain (CH 2CH 2O) 4OCH 3
Described C 5-C 12Side chain ether chain be glycol isopropyl ether (CH 2) 2OCH (CH 3) 2, terepthaloyl moietie isoamyl oxide (CH 2) 2O (CH 2) 2CH (CH 3) 2, ethylene glycol bisthioglycolate isoamyl oxide (CH 2) 2O (CH 2) 2CH (CH 3) CH 2O (CH 2) 2CH (CH 3) 2
When light rare earths and the gadolinium that separates except that promethium, be extracted to pH is the water of 6.5-7 to the above-mentioned cyclophane amide compound that contains three center hydrogen bonds as extraction agent.
The above-mentioned cyclophane amide compound that contains three center hydrogen bonds as extraction agent when light rare earths and the gadolinium that separates except that promethium, the molar ratio of REE and extraction agent≤1.
When light rare earths and the gadolinium that separates except that promethium, the minimum concentration of extraction agent after diluent is 1 * 10 to the above-mentioned cyclophane amide compound that contains three center hydrogen bonds as extraction agent -4Mol/L.
Above-mentioned thinner is methylene dichloride or trichloromethane.
Promethium is a radioelement, is inappropriate for extracting process of the present invention, so the light rare earths of indication of the present invention is lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), samarium (Sm) and europium (Eu); Heavy rare earth element is gadolinium (Gd).
Can use the REE of extraction agent extraction of the present invention to be lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), samarium (Sm), europium (Eu) and gadolinium (Gd).
The useful technique effect that the present invention brings:
1, to contain the cyclophane acid amides extraction agent of three center hydrogen bonds be one type of extraction agent that composition is single, chemicalstability is good in the present invention; And the consumption of extraction agent is very little; Percentage extraction to most of REEs when the mol ratio of REE and extraction agent is merely 1:1 just can reach more than 90%; So after the amount that strengthens extraction agent, percentage extraction all can reach more than 90%.
2, extraction agent provided by the invention can be under low consistency conditions extracting and separating rear earth element effectively; When extraction, can in neutral solution, extract.
3, the R group can be regulated its solvability in different solvents, makes it can be widely used in the different solvents system.
4, this extraction agent also have advantages such as rate of extraction is fast, the branch phase velocity is fast, so such cyclophane acid amides that contains three center hydrogen bonds has the prospect of practical application as the novel extraction agent of extracting and separating rear earth element when the extracting rare-earth element.
Embodiment
Embodiment 1
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 1:
Contain wherein that R is C in the cyclophane amide compound of three center hydrogen bonds 11H 23
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the methylene dichloride dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 1
Element E(%) D
La 93 13.3
Ce 90 9.0
Pr 91 10.1
Nd 91 10.1
Sm 94 15.7
Eu 90 9.0
Gd 95 19.0
E is a percentage extraction, and D is a partition ratio.
Embodiment 2
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 2:
Contain wherein that R is C in the cyclophane amide compound of three center hydrogen bonds 12H 25
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the trichloromethane dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 2
Element E(%) D
La 92 11.5
Ce 94 15.7
Pr 90 9.0
Nd 95 19.0
Sm 89 8.1
Eu 93 13.3
Gd 91 10.1
E is a percentage extraction, and D is a partition ratio.
Embodiment 3
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 3:
Contain wherein that R is C in the cyclophane amide compound of three center hydrogen bonds 16H 33
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the methylene dichloride dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 3
Element E(%) D
La 92 11.5
Ce 78 3.5
Pr 90 9.0
Nd 93 13.3
Sm 86 6.1
Eu 90 9.0
Gd 92 11.5
E is a percentage extraction, and D is a partition ratio.
Embodiment 4
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 4:
Contain wherein that R is CH in the cyclophane amide compound of three center hydrogen bonds 2CH (CH 2CH 3) (CH 2) 3CH 3
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the trichloromethane dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 4
Element E(%) D
La 92 11.5
Ce 78 3.5
Pr 90 9.0
Nd 93 13.3
Sm 86 6.1
Eu 90 9.0
Gd 92 11.5
E is a percentage extraction, and D is a partition ratio.
Embodiment 5
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 5:
Contain wherein that R is CH in the cyclophane amide compound of three center hydrogen bonds 2CH (CH 2CH 3) (CH 2) 5CH 3
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the methylene dichloride dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 5
Element E(%) D
La 93 13.3
Ce 89 8.1
Pr 91 10.1
Nd 95 19.0
Sm 90 9.0
Eu 93 13.3
Gd 91 10.1
E is a percentage extraction, and D is a partition ratio.
Embodiment 6
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 6:
Contain wherein that R is CH in the cyclophane amide compound of three center hydrogen bonds 2CH (CH 2CH 3) (CH 2) 7CH 3
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the trichloromethane dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 6
Element E(%) D
La 90 9.0
Ce 92 11.5
Pr 90 9.0
Nd 94 15.7
Sm 91 10.1
Eu 95 19.0
Gd 94 15.7
E is a percentage extraction, and D is a partition ratio.
Embodiment 7
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 7:
Contain wherein that R is (CH in the cyclophane amide compound of three center hydrogen bonds 2CH 2O) 2OCH 3
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the methylene dichloride dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 7
Element E(%) D
La 94 15.7
Ce 97 32.3
Pr 96 24.0
Nd 98 49.0
Sm 97 32.3
Eu 98 49.0
Gd 99 99.0
E is a percentage extraction, and D is a partition ratio.
Embodiment 8
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when separating light rare earths, and extraction results is seen table 8:
Contain wherein that R is (CH in the cyclophane amide compound of three center hydrogen bonds 2CH 2O) 3OCH 3
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the trichloromethane dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 8
Element E(%) D
La 92 11.5
Ce 95 19.0
Pr 97 32.3
Nd 94 15.7
Sm 93 13.3
Eu 97 32.3
Gd 96 24.0
E is a percentage extraction, and D is a partition ratio.
Embodiment 9
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 9:
Contain wherein that R is (CH in the cyclophane amide compound of three center hydrogen bonds 2CH 2O) 4OCH 3
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the methylene dichloride dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 9
Element E(%) D
La 95 19.0
Ce 96 24.0
Pr 98 49.0
Nd 94 15.7
Sm 96 24.0
Eu 95 19.0
Gd 98 49.0
E is a percentage extraction, and D is a partition ratio.
Embodiment 10
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 10:
Contain wherein that R is (CH in the cyclophane amide compound of three center hydrogen bonds 2) 2OCH (CH 3) 2
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the trichloromethane dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 10
Element E(%) D
La 91 10.1
Ce 90 9.0
Pr 94 15.7
Nd 92 11.5
Sm 93 13.3
Eu 94 15.7
Gd 95 19.0
E is a percentage extraction, and D is a partition ratio.
Embodiment 11
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 11:
Contain wherein that R is (CH in the cyclophane amide compound of three center hydrogen bonds 2) 2O (CH 2) 2CH (CH 3) 2
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the methylene dichloride dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 11
Element E(%) D
La 92 11.5
Ce 78 3.5
Pr 90 9.0
Nd 93 13.3
Sm 86 6.1
Eu 90 9.0
Gd 92 11.5
E is a percentage extraction, and D is a partition ratio.
Embodiment 12
The cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent when the separation of rare earth elements, and extraction results is seen table 12:
Contain wherein that R is (CH in the cyclophane amide compound of three center hydrogen bonds 2) 2O (CH 2) 2CH (CH 3) CH 2O (CH 2) 2CH (CH 3) 2
The mol ratio of extraction agent and REE is 1:1
Extraction agent concentration after the trichloromethane dilution is 1 * 10 -4Mol/L
Water is the group of the lanthanides inorganic salt: concentration (Ln (NO 3) 3): 1 * 10 -4Mol/L
Temperature: 20 ℃; Compare: 1/1; Vibration: 1 hour
Table 12
Element E(%) D
La 92 11.5
Ce 89 8.1
Pr 95 19.0
Nd 93 13.3
Sm 92 11.5
Eu 91 10.1
Gd 93 13.3
E is a percentage extraction, and D is a partition ratio.

Claims (6)

1. the cyclophane amide compound that contains three center hydrogen bonds is as the application of extraction agent in separating except that promethium light rare earths and gadolinium; The said cyclophane amide compound that contains three center hydrogen bonds has following structure:
Figure 2010105955839100001DEST_PATH_IMAGE001
R is C in the formula 11-C 16Linear alkyl chain, C 8-C 12Branched alkyl chain, C 5-C 9Linear chain or C 5-C 12Side chain ether chain.
2. the cyclophane amide compound that contains three center hydrogen bonds according to claim 1 is characterized in that as the application of extraction agent in separating except that promethium light rare earths and gadolinium:
Described C 11-C 16Linear alkyl chain be undecyl chain C 11H 23, dodecyl chain C 12H 25, hexadecyl chain C 16H 33
Described C 8-C 12Branched alkyl chain be iso-octyl chain CH 2CH (CH 2CH 3) (CH 2) 3CH 3, isodecyl chain CH 2CH (CH 2CH 3) (CH 2) 5CH 3, Permethyl 99A. base chain CH 2CH (CH 2CH 3) (CH 2) 7CH 3
Described C 5-C 9The linear chain be diethylene glycol monomethyl ether chain (CH 2CH 2O) 2OCH 3, triethylene glycol monomethyl ether chain (CH 2CH 2O) 3OCH 3, TEG monomethyl ether chain (CH 2CH 2O) 4OCH 3
Described C 5-C 12Side chain ether chain be glycol isopropyl ether (CH 2) 2OCH (CH 3) 2, terepthaloyl moietie isoamyl oxide (CH 2) 2O (CH 2) 2CH (CH 3) 2, ethylene glycol bisthioglycolate isoamyl oxide (CH 2) 2O (CH 2) 2CH (CH 3) CH 2O (CH 2) 2CH (CH 3) 2
3. the cyclophane amide compound that contains three center hydrogen bonds according to claim 1 is as the application of extraction agent in separating except that promethium light rare earths and gadolinium, and it is characterized in that: when the extracting and separating rear earth element, being extracted to pH is the water of 6.5-7.
4. the cyclophane amide compound that contains three center hydrogen bonds according to claim 1 is characterized in that: the molar ratio of REE and extraction agent≤1 as the application of extraction agent in separating except that promethium light rare earths and gadolinium.
5. the cyclophane amide compound that contains three center hydrogen bonds according to claim 1 is as the application of extraction agent in separating except that promethium light rare earths and gadolinium, and it is characterized in that: the minimum concentration of extraction agent after diluent is 1 * 10 -4Mol/L.
6. the cyclophane amide compound that contains three center hydrogen bonds according to claim 5 is as the application of extraction agent in separating except that promethium light rare earths and gadolinium, and it is characterized in that: described thinner is methylene dichloride or trichloromethane.
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