• Title/Summary/Keyword: styrene derivatives

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Microbial styrene monooxygenase-catalyzed asymmetric synthesis of enantiopure styrene oxide derivatives (미생물 유래 Styrene monooxygenase를 이용한 광학활성 styrene oxide 유도체의 비대칭합성)

  • Lee, Eun-Yeol;Park, Sung-Hoon
    • KSBB Journal
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    • v.24 no.3
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    • pp.239-245
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    • 2009
  • Enantiopure styrene oxide derivatives are versatile building blocks for the synthesis of enantiopure pharmaceuticals. Styrene monooxygenase (SMO) catalyzes an asymmetric addition of an oxygen atom into a double bond of vinylaromatic compounds. SMO is a commercially potential biocatalyst to synthesize a variety of enantiopure epoxides with high enantiopurity and recovery yield. In this paper development of SMO biocatalyst and commercial feasibility of SMO-catalyzed asymmetric synthesis of enantiopure stylers oxide derivatives are reviewed.

Kinetic Investigation of Styrene Derivatives Oxidation Mechanism by Mn(III)-porphyrin (Mn(III)-porphyrin에 의한 Styrene 유도체의 산화반응 메카니즘 연구)

  • Na, Hun-Gil
    • Journal of the Korean Applied Science and Technology
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    • v.19 no.3
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    • pp.206-212
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    • 2002
  • The catalytic activities of several metalloporphyrin, wherein the porphyrins are TPP(5,lO,l5,20-Tetraphenyl-21H,23H-porphyrin) and (p-X)TPP (X =$CH_{3}O$, $CH_{3}$, F, Cl), are reported for the oxidation of styrene and it's derivatives. The electronic effects of substrates and porphyrins on the catalytic activity of metalloporphyrin containing the transition metal ion such as Mn(III) was discussed. Investigating the correlation between the Michaelis-Menten's rate parameters and the substituent constants, we are going to analyze the influences on the changes of catalytic activity or rate determining step during the processes of the formation and the dissociation of the M-oxo-olefin.

The Kinetics and Mechanism of the Hydrolysis to Benzoyl Styrene Derivatives (Benzoyl Styrene 유도체의 가수분해 반응 메카니즘과 그 반응속도론적 연구)

  • Lee, Ki-Chang;Yoon, Chul-Hun;Hwang, Sung-Kwy;Oh, Se-Young
    • Journal of the Korean Applied Science and Technology
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    • v.12 no.1
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    • pp.35-41
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    • 1995
  • The Hydrolysis kinetics of Benzoyl Styrene Derivatives[I]${\sim}$[IV] was investigated by ultraviolet spectrophotometery in 5% dioxane-$H_2O$ at $40^{\circ}C$. The structure of these compounds were ascertained by means of ultraviolet, melting point, IR and NMR spectra. The rate equations which were applied over a wide pH range (pH $1.0{\sim}13.0$) were obtained. The substituent effects on Benzoyl styrene derivatives[I]${\sim}$[IV] were studied, and the hydrolysis were facilitated by electron attracting groups. On the basis of the rate equation and substitutent effect and final product, the plausible hydrolysis reaction mechanism was proposed: At pH 1.0${\sim}$pH 9.0, not relevant to the hydrogenl ion concentration, neutral $H_2O$ molecule competitively attacked on the double bond. By contrary. Above pH 9.0, It was proportional to concentration of hydroxidel ion.

The Kinetics and Mechanism of the Nucleophilic Addition of Thiourea for Benzoyl Styrene Derivatives (Benzoyl styrene유도체에 대한 Thiourea의 친핵성 첨가반응 메카니즘과 그 반응속도론적 연구)

  • Lee, Ki-Chang;Yoon, Chul-Hun;Hwang, Sung-Kwy;Ryu, Jung-Uk
    • Journal of the Korean Applied Science and Technology
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    • v.12 no.2
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    • pp.107-113
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    • 1995
  • Benzoyl styrene derivatives were synthesized by Claisen-Schmidt condensation. It was measured that nucleophilic addition of thiourea for benzoyl styrene made use of ultraviolet spectrophotometery at a wide pH $1.0{\sim}13.0$ range in 5% $dioxane-H_2O$ at $40^{\circ}C$. On the basis of general base catalysis, substitutent effect, and confirmation of addtion reaction product, the nucleophilic addtion kinetics of thiourea for benzoylstyrene derivatives were measured by pH change. It maybe concluded that a part was unrelated to pH and another part was in proportion to concentration of hydroxide ion : Above pH 10.0. It was in propotion to concentration of hydroxide ion, a part having no concern with pH was added to the neutral thiourea molecule. From the results of measurement the reaction rate and there findings, nucleophilic addition of thiourea to benzoylstyrene derivative was proposed a fitting mechanism.

Immobilization of Styrene-acrylamide Co-polymer on Either Silica Particles or Inner Surface of Silica Capillary for the Separation of D-Glucose Anomers

  • Ali, Faiz;Kim, Yune Sung;Cheong, Won Jo
    • Bulletin of the Korean Chemical Society
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    • v.35 no.2
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    • pp.539-545
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    • 2014
  • Styrene-acrylamide co-polymer was immobilized on porous partially sub-$2{\mu}m$ silica monolith particles and inner surface of fused silica capillary ($50{\mu}m$ ID and 28 cm length) to result in ${\mu}LC$ and CEC stationary phases, respectively, for separation of anomeric D-glucose derivatives. Reversed addition-fragmentation transfer (RAFT) polymerization was incorporated to induce surface polymerization. Acrylamide was employed to incorporate amide-functionality in the stationary phase. The resultant ${\mu}LC$ and CEC stationary phases were able to separate isomers of D-glucose derivatives with high selectivity and efficiency. The mobile phase of 75/25 (v/v) acetonitrile (ACN)/water with 0.1% TFA, was used for HPLC with a packed column (1 mm ID, 300 mm length). The effects of pH and ACN composition on anomeric separation of D-glucose in CEC have been examined. A mobile phase of 85/15 (v/v) ACN/30 mM sodium acetate pH 6.7 was found the optimized mobile phase for CEC. The CEC stationary phase also gave good separation of other saccharides such as maltotriose and Dextran 1500 (MW~1500) with good separation efficiency (number of theoretical plates ~300,000/m).

Improvement of Oxidative Stability for Non-fluorinated Membranes Prepared by Substituted Styrene Monomers (스티렌 유도체를 이용한 비불소계 고분자 전해질막의 산화적 안정성 개선)

  • Moon, Seung-Hyeon;Woo, Jung-Je;Fu, Rong-Qiang;Seo, Seok-Jun;Yun, Sung-Hyun
    • Membrane Journal
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    • v.17 no.4
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    • pp.294-301
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    • 2007
  • To improve oxidative stability of non-fluorinated styrene-based polymer electrolyte membranes, copolymerized membranes were prepared using styrene derivatives such as p-methylstyrene, t-butylstyrene, and ${\alpha}-methylstyrene$ by monomer sorption method. Prepared membrane was characterized by measurement of weight gain ratio, water content, ion-exchange capacity, proton conductivity, and oxidative stability under the accelerated condition. It was found that each step of monomer sorption method including sorption, polymerization and sulfonation could be affected by the properties and the structures of styrenederivatives. Due to difficulty of polymerization, ${\alpha}$-methylstyrene was copolymerized with styrene or p-methylstyrene. Prepared membrane using ${\alpha}-methylstyrene$ and styrene showed higher performance and stability comparing to copolymerized membrane with styrene. However, copolymerized membranes with ${\alpha}-methylstyrene$ did not showed much improved oxidative stability comparing to styrene membrane due to their lower molecular weight. The t-butylstyrene membrane showed a low performance due to substituted bulky-butyl group which prevents sorption and sulfonation reaction. However, copolymerized t-butylstyrene membranes with p-methylstyrene showed good performance and much improved stability than the styrene membranes.

Effect of Process Aids on Rheological and Mechanical Properties of Styrene-Butadiene Rubber Compound (가공조제가 Styrene-Butadiene Rubber 배합고무의 유변특성 및 기계적 물성에 미치는 영향)

  • Kang, Yong-Gu;Jung, Hoon;Kim, Tae-Nyun;Kim, Wan-Doo;Nah, Chang-Woon
    • Elastomers and Composites
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    • v.37 no.3
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    • pp.170-176
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    • 2002
  • Effects of type and loading level of process aids on the rheological and mechanical properties of styrene-butadiene rubber (SBR) compound were investigated. Five commercial grades of process aids composed of fatty acids and their various derivatives such as metal salts, esters, alcohols and amides were selected. The reduction in Mooney and shear viscosities was higher for metal salt-type process aids but lower for the process aids containing high molecular weight fatty acid alcohols and esters with increasing the loading of process aids. Tensile modulus generally decreased, while heat-build-up increased with increased process aids content. No considerable effect was observed for ulimate properties such as tensile strength and elongation at break.

Synthesis of Perfluorinated Heterocyclic Compounds Having a Long Alkyl Chain Functionality by 1,3-Dipolar Cycloaddition

  • Lee, Chan-Woo;Hwang, Ho-Yun;Park, Joo-Yuen;Chi, Ki-Whan
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1305-1308
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    • 2010
  • Regioselective perfluorinated isoxazolidine (5 and 7), isoxazoline (9) and 1,2-addition products (6 and 8) having a long alkyl chain functionality have been prepared by 1,3-dipolar cycloaddition between a 1,3-dipole (NH-nitrone or nitrile oxide) and dipolarophile (perfluoro-2-methyl-2-pentene or styrene), respectively. Interestingly, unusual extended conjugated form of isoxazoline adduct (10) was obtained by dehydrofluorinated reaction from the corresponding perfluorinated isoxazoline adduct (9) which was derived from cycloadition between the perfluorinated long alkyl nitrile oxide 1,3-diplole and styrene olefin. This synthetic methodology of heterocyclic compound having a long alkyl chain functionality is useful for the designing of synthetic strategy and potential self-assembled monolayers (SAM) application. These derivatives were characterized by IR, $^1H$ and $^{19}F$ NMR, and MASS analysis.