• Title, Summary, Keyword: crown ether

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Solvent Extraction of Alkali Metal and Alkaline Earth Metal Cations Using a Mono-Crown Ether and Bis-(Crown Ether)s (Mono-Crown Ether와 Bis-(Crown Ether)s를 이용한 알칼리금속과 알칼리토금속 양이온들의 용매추출)

  • Shin, Young-Kook;Kim, Hae-Joong
    • Analytical Science and Technology
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    • v.10 no.1
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    • pp.60-65
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    • 1997
  • Solvent extraction of alkali metal and alkaline earth metal cations by mono-crown ether(benzo-15-crown-5) and bis-(crown ether)s(ethylenediamine bis(4'-formyl benzo-15-crown-5)) containing benzo-15-crown-5 moieties were investigated with water-chloroform system at $25^{\circ}C$. The order of the extraction equilibrium constants($K_e$) and the complexation constants($K_c$) for the alkali metal and alkaline earth metal cations with mono-crown ether and bis-(crown ether)s were Ca(II)>Na(I)>Sr(II)>K(I)>Mg(II)>Rb(I) and Sr(II)>Ca(II)>K(I)>Rb(I)>Mg(II)>Na(I) respectively. These results were explained in terms of the size effect of metal cation and electron density effect. Also, the bis-(crown ether)s was found to extract metal cations more effectively than the corresponding mono-crown ether.

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Syntheses Bis or Tri Crown Ethers Containing Imine Group(V) (이민기를 포함하는 비스 또는 트리 크라운에테르의 합성 (V))

  • Chang, Seung-Hyun;Kim, Jung-Sung
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • pp.110-113
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    • 2003
  • We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers l~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers l~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-l5-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has phothosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-l5-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR. GC-Mass.

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Syntheses New Bis-Crown Ethers Containing Imine Group(III) (새로운 이민기를 포함하는 비스 크라운 에테르의 합성)

  • Lee, Sang-Hwoon;Jang, Dong-Chun;Chang, Seung-hyun
    • Journal of the Korean Society of Industry Convergence
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    • v.6 no.1
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    • pp.73-80
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    • 2003
  • We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers1~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers1~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-15-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has photosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-15-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR, GC-Mass.

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The synergistic solvent extraction effect of europium and yttrium using the hexanoic acid -crown ether system (Hexanoic acid - crown ether system을 이용한 europium과 yttrium의 용매추출효과의 향상)

  • Sim, Dea-Seon;Han, Hye-Rim;Kim, Se-Mi;Kim, Jeong-Hoon;Kim, Young-Wun;Jeong, Noh-Hee;Kang, Ho-Cheol
    • Journal of the Korean Applied Science and Technology
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    • v.32 no.1
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    • pp.31-39
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    • 2015
  • The synergistic solvent extraction of rare earth elements such as europium and yttrium has been investigated by the extractant with crown ether as an additive. Macrocyclic ligand as host-guest compounds form more stable complexes with metal ions which have the similar size of the cavity of crown ether. In our previous study[14] founded that the extraction used fatty acid of the various alkyl chain length. Based on the results of the previous experiment, the synergistic separation effect of two metals investigated that the hexanoic acid had was the worst extraction effect which added a crown ether such as 18-crown-6 ether, 15-crown-5 ether, and 12-crown-4 ether. In this study, the concentrations of hexanoic acid have showed the separation effect, and then the concentrations and kind of crown ether are performed for synergistic extraction at the hexanoic acid concentration of the highest separation effect. As a results, the separation rate is the highest value of 1.72 at 0.05 M hexanoic acid, and 0.002M 15-crown-5 ether is the best value in other concentrations and kind of crown ether, it is about twice of using only hexanoic acid. Moreover, the extraction species of two metals has been founded $MLR_3{\cdot}3RH$ form when added the crown ether.

Syntheses New Crown Ethers Containing Luminescent Coumarin Group(II) (Coumarin을 포함하는 새로운 형광 크라운 에테르의 합성(II))

  • Lee, Sang-Hwoon;Jang, Dong-Chun;Chang, Seung-Hyun
    • Journal of the Korean Society of Industry Convergence
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    • v.6 no.2
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    • pp.109-113
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    • 2003
  • We report herein synthetic results obtained new types of crown ethers containing coumarin group. Crown ethers containing coumarin group 1~3 are hydroxymethyl-15-crown-5-ether linked with 4-hydroxy coumarin-4-acetic acid by esterification reaction. Crown ethers containing coumarin group 1~3 have different cavity in each crown ether rings. The 12-crown-4 ether with coumarin 1 has the smallest cavity size. The 15-crown-5 ether with coumarine 2 has the medium cavity size. The 18-crown-6 ether with coumarin 3 has the largest cavity size. Therefore each crown ether with coumarin group will recognize different ionic radius meta. Because of different hole size in crown ethers, these crown ethers seem to be had different selectivity in luminescent sensors. The crown ethers with coumarine 1~3 synthesized hydroxymethyl-15-crown-5-ether and 4-hydroxy coumarin-4-acetic acid same ratio at one to one. The synthesized crown ethers were characterized respectively by IR, NMR. GC-Mass.

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Extraction of Alkali Metal Cation with Crown Ethers and HDEHP (Crown Ether와 HDEHP에 의한 알칼리금속이온의 추출)

  • Ihn Chong Lee;Si Joong Kim;Chul Lee
    • Journal of the Korean Chemical Society
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    • v.30 no.4
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    • pp.359-368
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    • 1986
  • Solvent extraction equilibria of alkali metal cation with crown ether (DC18C6, DC24C8) and HDEHP have been studied. The extraction equilibrium constants increase in the order of, in the DC18C6 system, $Na^+, and in the DC24C8 system, $Rb^+. The species extracted to organic phase are $M_1(crown ether)_1\;(HDEHP)_1$. The magnitude of extraction equilibrium constant is determined by the distribution ratio of crown ether between organic and aqueous phase, and stability constant of crown ether-alkali metal complex.

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The Nucleophilic Crown Ether Ring Cleavage of Nitro Derivatives of Dibenzo-18-crown-6-(I) (친핵성 치환 반응에 의한 Dibenzo-18-crown-6 의 Nitro 유도체 화합물의 Crown Ether 고리 끊어짐 (제 1 보))

  • Sae Hee Chang;Sung Ah Cho
    • Journal of the Korean Chemical Society
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    • v.32 no.1
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    • pp.71-78
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    • 1988
  • The crown ether ring of 20, 21, 24, 25-tetranitrodibenzo-18-crown-6(TNDB-18-C-6) was cleaved by various alcoholic bases to give 2,4,5-trialkoxynitrobenzene derivatives and 4,5-dialkoxy-1,2-dinitrobenzene derivatives as the major products, and bis[(alkoxynitrophenoxy)ethyl]ether derivatives from partially cleaved crown ether ring as the minor products. The ring cleavage reaction of TNDB-18-C-6 with ethylene glycolic base resulted ring contraction through intramolecular nucleophilic cyclization of the initially formed ring cleavage product to give nitro derivatives of DB-14-C-4.

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Solvent Extractions of Alkali Metal Cations and Alkaline Earth Cations by Ionizable Crown Ether Phosphonic Acids (이온성 크라운에테르 포스포닉산에 의한 알칼리 금속 양이온과 알칼리 토금속 양이온의 용매추출)

  • Chung, Yeong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.1
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    • pp.50-55
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    • 2005
  • A comparison of alkali metal cation and alkaline earth cation solvent extraction was made for three additional monoionizable crown ethers and one diionizable crown ether. sym-(n-Octyldibenzo)-16-crown-5-oxyacetic acid $\underline{1}$ exhibited high efficiency and selecvity in solvent extraction of alkali metal cations with respect to that observed with alkaline earth cations. Sizes of $Na^+$ and $Ca^{2+}$ appropriately match with the cavity size of monoethyl sym-bis[4(5)-tert-butylbenzo]-16-crown-5-oxymethylphosphonic acid $\underline{3}$. As the result, $Na^+$ and $Ca^{2+}$ are the best extracted. sym-(n-Octyldibenzo)-16-crown-5-oxymethyldiphosphonic acid $\underline{4}$was found to be somewhat selective for $Na^+$ over $Li^+$ and other alkaline earth metal cations. In the complexation of alklaine earth cations by crown ether diphosphonic acid $\underline{4}$, $Ca^{2+}$ and $Sr^{2+}$ are the appropriate sizes, but lager $Ba^{2+}$ may be due to favorable formation of a sandwich type complex between the crown ether cavity and the dianion of the deprotonated crown ether phoaphonic acid moiety.

Molecular Vibrational Study of the Allosteric Effect in 2,2'-Bipyridyl Crown Ether (분자진동방법을 사용한 2, 2'-Bipyridyl Crown Ether 의 다른자리 입체성 효과에 관한 연구)

  • Wan Kyu Kim;Soon Ryang Chung
    • Journal of the Korean Chemical Society
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    • v.29 no.3
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    • pp.205-212
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    • 1985
  • By using the Mass-Weighted-Cartesian coordinate method, the allosteric effect of 2,2'-bipyridyl crown(4) ether is studied. The vibrational modes of 235, 234, 188, and 178cm$^{-1}$ belong to the pore opening motion of crown ether and those of 168, 104, and 67cm$^{-1}$ belong to the rotational vibration motion of bipyridyl. Especially the mode appearing at 178cm$^{-1}$ shows a large allosteric effect by activation of the allosteric site.

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Competitive Solvent Extraction of the Mixture of Alkali Metal and Alkaline Earth Metal Cation containing Crown Ether Carboxylic Acid and Crown Ether Phosphonic Acid (크라운에테르 카르복시산과 크라운에테르 포스포닉산을 포함한 알칼리 금속과 알칼리 토금속 양이온 혼합물의 경쟁적 용매추출)

  • Chung, Yeong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.3
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    • pp.219-227
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    • 2005
  • Competitive solvent extraction of the mixure of alkali metal and alkaline earth cation from water into organic solvent containing the crown ether carboxylic acid and anlogous crown ether phosphonic acid was investigated as follows. The lipophilic group is found to strongly influence to the selective extraction in the mixed systems from only alkali metal cation for sym-(n-decyldibenzo)-16-crown-5-oxyacetic acid $\underline{1}$ to mostly alkaline earth metal cation for sym-bis[4(5)-tert-butylbenzo]-16-crown-5-oxyacetic acid $\underline{3}$. Monoethyl sym-(n-decyldibenzo)-16-crown-5-oxymethylphosphonic acid $\underline{2}$. and monoethyl-sym- bis]4(5)-tert-butylbenzo]-16-crown-5-oxymethylphosphonic acid $\underline{4}$ showed good selectivity for $Na^+$ over $Mg^{2+}$, the second extracted ion. Structural variation in the crown ether phosphonic acid somewhat was influenced to the extraction selectivity in the mixed systems. when variation of the ionized group is influenced in the mixed systems, the selectivity of $Na^+$ as the second extracted ion was much better crown ether carboxylic acid $\underline{1}$ than crown ether phosphonic acid $\underline{2}$, while the efficiency of $Na^+$ extraction was better $\underline{2}$ (83% total loading) than $\underline{1}$ (32%).