• Title/Summary/Keyword: 크라운에테르

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Synthesis of New Bis-Crown Ether (Ⅱ) : Bis-Crown Ether with Siloxane Moiety (새로운 비스-크라운 에테르의 합성(제 2보) : 실옥산 사슬에 연결된 비스-크라운 에테르)

  • Chang, Seung Hyun;Kim, Jae Yong;Chung, Kwang Bo
    • Journal of the Korean Chemical Society
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    • v.40 no.9
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    • pp.635-639
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    • 1996
  • New bis-crown ether containing siloxane chain was synthesized. 1,3-Bis(trimethylsiloxy)-1,3-dimethyl-1,3-di(4'-ethylbenzo-18-crown-6) disiloxane (1) was synthesized by reaction of 4'-vinylbenzo-18-crown-6 with 1,3-bis(trimethylsiloxy)-1,3-dimethyl-1,3-disiloxane in the presence of Pt catalyst. 4'-Vinylbenzo-18-crown-6 was prepared through five-step reaction which started from the reaction of catechol and acetic anhydride.

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Syntheses of Biologically Active Phosphinate Derivatives with a Pendant Monoazacrown Ether (모노아자크라운에테르 기능기를 가진 생리활성 포스피네이트 유도체의 합성)

  • Nam Chong-Woo;Chung Yeong-Jin;Yang Il-Woo
    • Journal of the Korean Chemical Society
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    • v.37 no.1
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    • pp.154-161
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    • 1993
  • Four kinds of new phosphinate derivatives with a pendant monoazacrown ether were synthesized and their biological activities were tested. These biologically active phosphinates were synthesized in relatively good yields (61∼72%) by one step reactions of phenylphosphinate with aldehyde and monoazacrown ether. Toxicity of these compounds was tested by intraperitoneal injection of the compounds to male mouse and revealed $LD_{50}$ value of 65∼90 mg/kg, which showed enhanced toxicity by attachment of a pendant azacrown ether to a simple phenylphosphinate structure. Although the ring size effect of the pendant crown ethers, (monoaza-15-crown-5 and monoazo-18-crown-6), beening negligible, the identity of the ester functional group in the phosphinate structure exerted sizable influence on toxicity. Thus, phosphinate derivative with octyl or propyl ester group showed somewhat higher toxicity than that with ethyl ester group.

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Reversed-Phase Ion-Pair High Performance Liquid Chromatographic Elution Behavior of Noble Metal-Thiacrown Ether Complexes (귀금속-티아크라운에테르 착물들의 역상 이온쌍 고성능 액체크로마토그래피 용리거동)

  • Chung, Yong Soon;Kim, Dong Won;Lee, Kang Woo;Kim, Chang Seok
    • Journal of the Korean Chemical Society
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    • v.42 no.4
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    • pp.416-421
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    • 1998
  • In the reversed-phase ion-pair high performance liquid chromatographic (RPIP-HPLC) elution behavior of noble metal-thiacrown ether complexes, the effects of the concentration of ion-pairing reagent and kind of ligands were studied. It was found that the less the number of atoms in the ring of the thiacrown ether molecule was, the larger the selectivity was, and the elution mechanism of the complexes was explained due to the formation of ion-pair when the concentration of sodium dodecyl sulfate (SDS) in mobile phase was lower than 10 mM and due to the formation of micelle when the SDS concentration was higher than 10 mM. As a conclusion, separations of the noble metal-thiacrown ether complexes in an optimum separation condition were accomplished successfully and the method was proved to be an useful one for the separation and determination of Ag (Ⅰ) ion in a black-white photographic fixing solution.

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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%).

Syntheses of Novel Bis-Crown Ethers(Ⅰ) : Crown Ethers with Siloxane Moiety (새로운 비스-크라운 에테르류의 합성 (제 1 보) : 실옥산 사슬에 연결된 크라운 에테르)

  • Jang, Seung Hyeon;Kim, Jae Yong
    • Journal of the Korean Chemical Society
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    • v.38 no.5
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    • pp.377-381
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    • 1994
  • New bis-crown ethers containing siloxane chain were synthesized. 1,3-Bis(trimethylsiloxy)-1,3-dimethyl-1,3-dipentaoxacyclohexadecamethyl disiloxane (1) was synthesized by reaction of 3-methylene-16-crown-5 (8) with 1,3-bis(trimethylsiloxy)-1,3-dimethyl disiloxane (10) in the presence of Pt catalyst. 1,1,3,3,5,5-Hexamethyl-1,5-dipentaoxacyclohexadecamethyl trisiloxane (2) was synthesized by the reaction of crown ether (8) with 1,1,3,3,5,5-hexamethyl trisiloxane (11) in the presence of Pt catalyst. 3-Methylene-13-crown-4 (7), 3-methylene-16-crown-5 (8), and 3-methylene-19-crown-6 (9) were synthesized by the reaction of triethylene glycol (3), tetraethylene glycol (4), and pentaethylene glycol (5) respectively with 3-chloro-2-chloro-methyl-1-propene (6) in the presence of NaH.

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Synthesis of Hydroxy-terminated Poly(propylene carbonate) (Hydroxy-terminated Poly(propylene carbonate)의 합성)

  • Jung, S.M.;Moon, J.Y.;Park, D.W.;Park, S.W.;Lee, J.K.
    • Applied Chemistry for Engineering
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    • v.9 no.2
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    • pp.273-277
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    • 1998
  • The synthesis of hydroxy-terminated poly(propylene carbonate)(HTPPC) was performed by the reaction of propylene carbonate(PC) with alcohol initiator using metal alkoxides, crown ethers and quaternary onium salts as catalysts. The effects of catalyst structure, types and concentration of alcohol, and solvent were investigated. Among the alkoxide catalysts tested, the ones with higher Lewis acidity and with more nucleophilic alkoxide anion showed higher catalytic activity. Mixed catalysts of metal alkoxied and crown ether showed higher conversion of PC than metal alkoxide alone. Quaternary onium salts of bulky cation exhibited higher catalytic activity. High polar solvent showed higher yield of HTPPC and the yield increased with the decrease of [PC]/[Initiator] ratio.

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Polymer-Supported Crown Ethers (II). Efficiency for Phase Transfer Catalyst (고분자 물질로 지지된 크라운 에테르류(II) 상이동 촉매 효능)

  • Jae Hu Shim;Kwang Bo Chung;Seung Hyun Chang;Dae Kyung Song;Yong Kiel Sung
    • Journal of the Korean Chemical Society
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    • v.32 no.6
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    • pp.593-602
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    • 1988
  • Polymer-supported crown ethers (Ps-CE) which can be used for phase-transfer catalyst (PTC) were synthesized for the purpose of allowing reusable function to ordinary crown ethers, and the kinetics of the liquid-solid-liquid triphase-catalyzed nucleophilic displacement reaction of iodide (aqueous phase) on 1-bromooctane (organic phase) using synthesized Ps-CE (solid) were studied. Ps-CE were obtained by grafting of hydroxymethyl crown ethers to 1~2% cross-linked chloromethylated polystyrene. All reactions followed a pseudo-first order dependency on the 1-bromooctane concentration and the observed rate constants $(k_{obsd})$ were linearly related to the molar equivalents of Ps-CE, and were subjected to the influence of cross-linking density of polymer backbone, solvent and the reaction temperature. The catalytic activity of Ps-CE was also compared with that of structurally similar soluble crown ethers, and used Ps-CE were easily recovered after the reaction by simple filtration and could be reused without loss of catalytic activity in the same anionic displacement reaction. Enthalpies and entropies of activation associated with the displacement were 10~20kcal $mol^{-1}, 20~55eu. respectively, and the free energy of activation was ~30kcal mol^{-1}$.

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Competitive Solvent Extraction of Alkali Metal Ions with Azacrown Ether Phosphinic Acids (아자크라운에테르포스피닉산에 의한 알카리금속이온의 경쟁용매추출)

  • Nam, Chong-Woo;Chung, Yeong-Jin;Yang, Il-Woo
    • Applied Chemistry for Engineering
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    • v.3 no.2
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    • pp.266-272
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    • 1992
  • Azacrownoalkyl phenylphosphinic acids were synthesized and their competitive solvent extraction characteristics from water to chloroform layer were investigated. Phosphinic acids were synthesized in good yields by one step reaction of phenylphosphinate, aldehyde, and monoazacrown ether and then basic hydrolysis of the resulting phosphinate dsters. These complexing agents revealed a wide effective pH range in extraction of alkali metal ions from water to the organic phase and total metal ion loading at pH 11 was about 75%. The selectivity of the cation extraction was determined mainly by the cavity size of the azacrown ethers, showing $Na^+$ >> $K^+$ > $Rb^+$ > $Li^+$ > $Cs^+$ for the alkyl phenylphosphinic acid ${\underline{2}}$, containing monoaza-15-crown-5 and $K^+$ >> $Rb^+$ > $Na^+$ > $Cs^+$ > $Li^+$ for the alkyl phenylphosphinic acid, ${\underline{3}}$, containing monoaza-18-crown-6 moiety. Applicable pH range of these azacrown ether phosphinic acids in solvent extraction of alkali metal cations was wider than a crownether carboxylic acid with similar selectivity, showing considerable amount of metal ion loading in slightly acidic or neutral media.

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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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    • 2003.08a
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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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