• Journal of the Korean Applied Science and Technology
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• v.25 no.4
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• pp.469-476
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• 2008

The synthesis of cyclic carbonate from butyl glycidyl ether (BGE) and carbon dioxide was performed in the presence of three different types of ionic liquid : quarternary ammonium salt, alkyl pyridinium salt, and alkylimidazolium salt. Ionic liquids of different alkyl groups ($C_3$, $C_4$, $C_6$ and $C_8$) and anions ($Cl^-$, $Br^-$ and $I^-$) were used for the reaction which was carried out in a batch autoclave reactor at $60{\sim}120^{\circ}C$. The catalytic activity was increased with increasing alkyl chain length in the order of $C_3$ < $C_4$ < $C_6$. But the ionic liquid with longer alkyl chain length ($C_8$) decreased the conversion of BGE because it is too bulky to form an intermediate with BGE. For the counter anion of the ionic liquid catalysts, the BGE conversion decreased in the order $Cl^-$ > $Br^-$ > $I^-$.

• Elastomers and Composites
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• v.45 no.4
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• pp.256-262
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• 2010

Dispersion polymerization of methyl acrylate, ethyl acrylate, butyl acrylate, and glycidyl methacrylate were performed in supercritical $CO_2$ at $80\;^{\circ}C$ and 346 bar. Glycidyl methacrylate linked poly(dimethylsiloxane) (GMS-PDMS) surfactant, which was prepared by linking glycidyl methacrylate to monoglycidyl ether terminated PDMS with amino-propyltriethoxysilane, was used as surfactant for the dispersion polymerization in $CO_2$. The yield of the poly(alkyl acrylate) polymers, synthesized in $CO_2$ medium, decreased as the alkyl tail of the acrylate monomers increased. Poly(glycidyl methacrylate) and poly(methyl acrylate) were produced in bead form whereas poly(ethyl acrylate) and poly(butyl acrylate) were viscous liquid. The poly(glycidyl methacrylate) particles had a number average diameter of 2.45 ${\mu}m$ and monodisperse distribution. The poly(methyl acrylate) had a number average diameter of 0.52 ${\mu}m$ and the particle size distribution was bimodal. The glass transition temperatures ($T_g$) of the poly(glycidyl methacrylate) and the poly(alkyl acrylate) products were 4~9 K higher than the $T_g$ of the corresponding acrylate polymers synthesized in conventional processes.

• Applied Chemistry for Engineering
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• v.23 no.4
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• pp.416-420
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• 2012

A convenient procedure for the synthesis of fatty acid diesters was studied. Long chain diesters have been used as biolubricant and transformer oils. The series of octyl, dodecyl, hexadecyl, octadecyl, and octadec-9-enyl glycidyl ether were used to synthesize those diesters. Alkyl glycidyl ethers were reacted with fatty acid such as oleic acid and octanoic acid, and octanoic acid. The one-step / two-step reactions were compared during the condensation reaction. The products were confirmed by $^{1}H-NMR$, FT-IR, and HR/MS spectra. The yield of the product 1-O-acyl-2-O, 3-O-dioctadec-9-enoylglycerol was 55~60%.

• Applied Chemistry for Engineering
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• v.7 no.1
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• pp.26-33
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• 1996

This study is related to the investigation of the characteristics of phase transfer catalysts on the addition reaction of carbon dioxide and phenyl glycidyl ether(PGE). Quaternary ammonium salts showed a good conversion of PGE at l atm of $CO_2$. Among the quaternary ammonium salts tested, the ones with higher alkyl chain length and with more hydrophilic counter anion showed higher catalytic activity. Polyethylene glycol and crown ether were also effective catalysts when they are used with NaI. High pressure of $CO_2$increased the conversion of PGE by increasing solubility of $CO_2$in NMP. A mechanism of the reaction involving the role of phase transfer catalyst was also proposed.

• Archives of Pharmacal Research
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• v.21 no.4
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• pp.452-457
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• 1998

Three compounds, 5-(acetoxymethyl)-5-(hydroxymethyl)-3-tetradecyl-2,5-dihydro-2-furanone (3), 5-(acetoxymethyl)-5-(hydroxymethyl)-3,3-dihexyltetrahydro-2-furanone (4) and 5-(acetoxymethyl)-5-(hydroxymethyl)-3,3-dioctyltetrahydro-2-furanone (5), were designed and synthesized as surrogates of the ultrapotent DAG analogue, 5-(acetoxymethyl)-5-(hydroxymethyl) 3-[(Z)-tetradecylideneltetrahydro-2-furanone (1), a compound that showed high affinity for PKC-$\alpha$ ($K_1$=35 nM) in a competition binding assay with [$^3H$-20]phorbol-12,13-dibutyrate (PDBU). In an attempt to overcome the problem of generating geometrical E- and Z- isomers, as encountered with 1, the double bond was moved to an endocyclic location as in 3, or an additional alkyl chain was appended to C3 to give the corresponding 3,3-dialkyl saturated lactones (4 and 5). The lactone was constructed from glycidyl-4-methoxyphenyl ether in 5 steps. The target compounds showed reduced binding affinities for PKC-.alpha. with $K_{i}$ values of 192 nM (3), 4,829 nM (4), and 2,812 nM (5), respectively. These results indicate that constrained DAG analogues having a tetrahydro-2-furanone template are effectively discriminated by PKC-(X in terms of the direction of the long alkyl chain connected to the 3-position.n.

• Applied Chemistry for Engineering
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• v.27 no.5
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• pp.490-494
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• 2016

This paper describes the very efficient and highly enantioselective ring opening of terminal epoxides with alkyl and arene sulfonic acid. The dinuclear chiral (salen) Co complexes bearing Lewis acids of Al, Ga and In catalyze the reaction enantioselectively in the presence of tetrabutylammonium chloride using tert-butyl methyl ether as a solvent. The variation of the anion of the tetra butyl ammonium salt has significant impact on the reactivity and selectivity of the asymmetric ring opening of phenyl glycidyl ether with p-toluenesulfonic acid. The order of reactivity and selectivity was found to be $Cl^-$ > $l^-$ > $Br^-$ > $OH^-$. Strong synergistic effects of the different Lewis acid centers of Co-Al, Co-Ga and Co-In complexes were observed in the catalytic process. The dinuclear chiral salen catalyst containing $AlCl_3$ was found to be most active and highly enantioselective (91% ee).

• Applied Chemistry for Engineering
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• v.18 no.3
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• pp.218-226
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• 2007

The stereoselective synthesis of chiral terminal epoxides is of immense academic and industrial interest due to their utility as versatile starting materials as well as chiral intermediates. In this study, new dinuclear chiral Co (salen) complexes bearing gallium-, indium- and tallium-chloride have been synthesized and characterized. The mass and EXAFS spectra provided the direct evidence of formation of dinuclear complex. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of various terminal epoxides having ether or ester groups by hydrolytic kinetic resolution technology. The easily prepared dimeric complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ nucleophile, providing enantiomerically enriched terminal epoxides (> 99% ee). The dimeric structured chiral salen showed remarkably enhanced reactivity and may be employed substantially lower loadings than its monomeric analogues. The system described in this work is very efficient for the synthesis of chiral epoxide and 1,2-diol intermediates