• Title/Summary/Keyword: Benzyl alcohols

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A Study for Mechanism and Oxidation Reaction of Substituted Benzyl Alcohols using Cr(VI)-Heterocyclic Complex[Cr(VI)-2-methylpyrazine] (Cr(VI)-헤테로고리 착물[Cr(VI)-2-methylpyrazine]를 이용한 치환 벤질 알코올류의 산화반응과 메카니즘에 관한 연구)

  • Kim, Young-Sik;Park, Young-Cho
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.14 no.11
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    • pp.6039-6046
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    • 2013
  • Cr(VI)-heterocyclic complex[Cr(VI)-2-methylpyrazine] was synthesized by the reaction between of heterocyclic compound(2-methylpyrazine) and chromium trioxide, and characterized by IR and ICP analysis. The oxidation of benzyl alcohol using Cr(VI)-2-methylpyrazine in various solvents showed that the reactivity increased with the increase of the dielectric constant(${\varepsilon}$), in the order : cyclohexene${\rho}$) was Cr(VI)-2-methylpyrazine= -0.65(308K). The observed experimental data have been ratiolized. The hydride ion transfer causes the prior formation of a chromate ester in the rate-determining step.

Kinetics and Mechanism of the Oxidation of Substituted Benzyl Alcohols by Cr(VI)-Heterocyclic Complex (2,4'-Bipyridinium Chlorochromate) (크롬(VI)-헤테로고리 착물(2,4'-비피리디늄 클로로크로메이트)에 의한 치환 벤질 알코올류의 산화반응에서 속도론과 메카니즘)

  • Park, Young Cho;Kim, Young Sik
    • Applied Chemistry for Engineering
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    • v.25 no.6
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    • pp.648-653
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    • 2014
  • Cr(VI)-heterocyclic complex (2,4'-bipyridinium chlorochromate) was synthesized by the reaction between heterocyclic compound(2,4'-bipyridine) and chromium trioxide, and characterized by IR and ICP analysis. The oxidation of benzyl alcohol using 2,4'-bipyridinium chlorochromate in various solvents showed that the reactivity increased with the increase of the dielectric constant (${\varepsilon}$), in the order : N,N-dimet-hylformamide (DMF) > acetone > chloroform > cyclohexene. In the presence of DMF solvent with acidic catalyst such as hydrochloric acid (HCl solution), 2,4'-bipyridinium chlorochromate oxidized benzyl alcohol (H) and its derivatives (p-$CH_3$, m-Br, m-$NO_2$). Electron-donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (${\rho}$) was -0.67 (303 K). The observed experimental data have been rationalize the proton transfer occurred followed the formation of a chromate ester in the rate-determining step.

Kinetics of the Oxidation of Substituted Benzyl Alcohols using 6-Methylquinolinium Dichromate (6-Methylquinolinium Dichromate를 이용한 치환 벤질 알코올류의 산화반응 속도)

  • Kim, Young-Sik;Park, Young-Cho
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.12 no.12
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    • pp.5990-5996
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    • 2011
  • 6-Methylquinolinium dichromate[$(C_{10}H_9NH)_2Cr_2O_7$] was synthesized by the reaction of 6-methylquinoline with chromium trioxide in $H_2O$, and characterized by IR, ICP. The oxidation of benzyl alcohol using 6-methylquinolinium dichromate in various solvents showed that the reactivity increased with the increase of the dielectric constant(${\varepsilon}$), in the order: cyclohexene < chloroform < acetone < N,N- dimethylformamide. In the presence of hydrochloric acid($H_2SO_4$ solution), 6-methylquinolinium dichromate oxidized benzyl alcohol and its derivatives(p-$OCH_3$, m-$CH_3$, H, m-$OCH_3$, m-Cl, m-$NO_2$) smoothly in DMF. Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant(${\rho}$) was -0.67(303K). The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.

Kinetic Study on the Oxidation Reaction of Substituted Benzyl Alcohols by Cr(VI)-Heterocyclic Complex (2,2'-Bipyridinium Dichromate) (크롬(VI)-헤테로고리 착물(2,2'-Bipyridinium Dichromate)에 의한 치환 벤질 알코올류의 산화반응에 대한 속도론적 연구)

  • Kim, Young Sik;Park, Young Cho
    • Applied Chemistry for Engineering
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    • v.23 no.2
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    • pp.241-246
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    • 2012
  • Cr(VI)-heterocyclic complex (2,2'-bipyridinium dichromate) was synthesized by the reaction between of 2,2'-bipyridine and chromium trioxide in $H_2O$, and characterized by IR and ICP. The oxidation of benzyl alcohol using 2,2'-bipyridinium dichromate in various solvents showed that the reactivity increased with the increase of the dielectric constant, in the order: cyclohexene < chloroform < acetone < N,N-dimethylformamide. In the presence of DMF solvent with acidic catalyst such as $H_2SO_4$ solution, 2,2'-bipyridinium dichromate oxidized the benzyl alcohol and its derivatives (p-$p-OCH_3$, $m-CH_3$, H, $m-OCH_3$, m-Cl, $m-NO_2$). Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant was -0.66 (303 K). The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.

A Study for Kinetics and Oxidation Reaction of Substituted Benzyl Alcohols Using 2,4'-Bipyridinium Dichromate (2,4'-Bipyridinium Dichromate를 이용한 치환 벤질 알코올류의 산화반응과 반응속도에 관한 연구)

  • Kim, Young Sik;Park, Young Cho
    • Applied Chemistry for Engineering
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    • v.22 no.6
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    • pp.718-722
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    • 2011
  • 2,4'-Bipyridinium dichromate [$(C_{10}H_8N_2H)_2Cr_2O_7$] was synthesized by the reaction of 2,4'-bipyridinie with chromium trioxide in $H_2O$. The structure was characterized by IR and ICP analysis. The oxidation of benzyl alcohol using 2,4'-bipyridinium dichromate in various solvents showed that the reactivity increased with the increase in the order of the dielectric constant (${\varepsilon}$), in the order : cyclohexene < chloroform < acetone < N,N'-dimethylformamide. In the presence of hydrochloric acid, 2,4'-bipyridinium dichromate effectively oxidized benzyl alcohol and its derivatives ($p-CH_3$, H, m-Br, $m-NO_2$) in N,N'-dimethylformamide. Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant (${\rho}$) was -0.65 at 303 K. The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.

Volatile Flavor Characteristics of Propolis (Propolis의 휘발성 향기 성분 특성)

  • Song, Hyo-Nam;Kim, Young-Eon;Hwang, In-Kyeong;Ahn, Seung-Yo
    • Korean Journal of Food Science and Technology
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    • v.31 no.5
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    • pp.1153-1158
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    • 1999
  • Propolis is a resinous bee-hive product that honeybees collect from plant exudates, flower and leaves. Flavor characteristics of two varieties of propolis collected from different plant origins, falseacacia(Robinia psedoacacia L.) and chestnut tree(Castanea crenata), were analyzed using Aroma Scan and GC/MS. Two varieties of propolis were grouped with quite different aroma profiles by Aroma Scan. Fifty five flavor compounds were identified by GC/MS, of which 44 compounds were found from the propolis of falseacacia and 47 compounds from chestnut tree. Five aldehydes, eight alcohols. five ketones, three esters, one fatty acid, twenty seven hydrocarbons. two terpenes and four phenolic derivatives were identified. Thirty six compounds including benzaldehyde, cinnamyl alcohol, eudesmol and benzyl benzoate were detected in both propolis, eight compounds including geraniol and n-undecane only in propolis of falseacacia and eleven compounds including piperitenone and valencene only in chestnut tree.

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Screening of Radical Scavenging Activity from the Marine-Derived Fungus (해양균류의 라디칼 소거활성 검색)

  • Li, Xi Feng;Li, Yong;Nam, Ki-Wan;Kim, Dong-Soo;Choi, Hong-Dae;Son, Byeng-Wha
    • Korean Journal of Pharmacognosy
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    • v.33 no.3 s.130
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    • pp.219-223
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    • 2002
  • In order to screen new radical scavenging principle which is expected to be antiaging drug lead, we have isolated 160 strains of the marine-derived fungi and investigated 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity for their acetone extracts. The significant activities (>50% Inhibition) were observed in 8 strains of fungi (MFA006, MFA0l4, MFA040, MFA133, MFA139, MFA143, MFA148, MFA153), and among them, MFA153 (Aspergillus parasiticus) showed the most significant radical scavenging activity. The active components were purified by assay-guided isolation to yield two known benzyl alcohols, l53B3 (1) and l53B4 (2), and their structures were determined by physicochemical evidence. Two compounds (1,2) showed the significant radical scavenging activity with $IC_{50}$ values of 0.6 and $1.4{\mu}M$ against DPPH, respectively.

Changes in the Composition of Essential Oils during Air-Curing Process of Burley 21 Tobacco (Burley 21 잎담배에서 건조기간중의 정유성분 조성의 변화)

  • Hong, Yeol;Lim, Heung-Bin
    • Journal of the Korean Society of Tobacco Science
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    • v.25 no.1
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    • pp.39-46
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    • 2003
  • The essential oils from Burley 21 tobacco was isolated by using the SDE (Simultaneous Distillation & Extraction) apparatus coupled with gas chromatography and mass spectrometry analysis. Burley 21 tobaccos were divided and collected by six stages at intervals of five days during air-curing process. Air curing was conducted with horizontal hanging method in greenhouse settled by shading materials. 55 components were identified by comparisons of retention indices and mass spectral data, including 22 hydrocarbons, 6 alcohols, 3 aldehydes, 9 ketones and 15 miscellaneous compounds. Neophytadiene was the major components of the oils and almost all hydrocarbons were gradually decreased during air-curing process. Most of alcohols were also diminished, on the contrary, 1-pentanol and benzyl alcohol among them were increased. Aldehydes and ketones were increased during air-curing and especially, the concentrations of solanone, $\beta$-damascone, $\beta$-damascenone and megastigmatrienones were much increased. Indole level of miscellaneous compounds were continuously increased during air-curing of Burley 21 tobacco.

Selective Reduction by Lithium Bis- or Tris(dialkylamino)aluminum Hydrides. VIII. Reaction of Lithium Tripiperidinoaluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups

  • 차진순;이재철;주영철
    • Bulletin of the Korean Chemical Society
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    • v.18 no.8
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    • pp.890-895
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    • 1997
  • The approximate rates and stoichiometry of the reaction of excess lithium tripiperidinoaluminum hydride (LTPDA), an alicyclic aminoaluminum hydride, with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, 25°) were examined in order to define the reducing characteristics of the reagent for selective reductions. The reducing ability of LTPDA was also compared with those of the parent lithium aluminum hydride (LAH) and lithium tris(diethylamino)aluminum hydride (LTDEA), a representative aliphatic aminoaluminum hydride. In general, the reactivity of LTPDA toward organic functionalities is weaker than LTDEA and much weaker than LAH. LTPDA shows a unique reducing characteristics. Thus, benzyl alcohol, phenol and thiols evolve a quantitative amount of hydrogen rapidly. The rate of hydrogen evolution of primary, secondary and tertiary alcohols is distinctive. LTPDA reduces aldehydes, ketones, esters, acid chlorides and epoxides readily to the corresponding alcohols. Quinones, such as p-benzoquinone and anthraquinone, are reduced to the corresponding diols without hydrogen evolution. Tertiary amides and nitriles are also reduced readily to the corresponding amines. The reagent reduces nitro compounds and azobenzene to the amine stages. Disulfides are reduced to thiols, and sulfoxides and sulfones are converted to sulfides. Additionally, the reagent appears to be a good partial reducing agent to convert primary carboxamides into the corresponding aldehydes.

Volatile Components of Green Tea(Camellia sinensis L. var. Yabukita) by Purge and Trap Headspace Sampler (Purge와 Trap Headspace Sampler를 이용한 녹차의 휘발성 성분)

  • 이재곤;권영주;장희진;곽재진;김옥찬;최영현
    • The Korean Journal of Food And Nutrition
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    • v.10 no.1
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    • pp.25-30
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    • 1997
  • Volatile components of green tea were isolated by purge and trap headspace method and were analyzed by GC and GC/MSD. And ten headspace volatiles were compared with volatiles isolated by simultaneous distillation-extraction(SDE) method. A total of 99 components were identified in the green tea volatile components, from which 88 components were identified in the headspace volatiles, contained 20 alcohols, 30 hydrocarbons, 21 aldehydes, 10 ketones, 2 acids and 5 miscellaneous components. The major components were low boiling components, such as methyl butanal(3.1%), 1-penten-3-ol(5.48%), 2-penten-1-ol(2.89%), hexanal(5.77%), heptanal(1.90%), and ere 2,4-eptadienal(4.28%), linalool(2.27%), 2,6-dimethyl cyclohexanol(2.57%), $\alpha$-pinene(1.52%), caryophyllene(1.70%), and carbonyl compounds, such as $\alpha$-ionone(2.62%), $\beta$-ionone(2.98%), $\beta$-cyclocitral(2.0%). On the other hand SDE volatiles, from which 64 components were identified, contained 16 alcohols, 16 ydrocarbons, 15 aldehydes, 10 ketones, 3 acids and 4 miscellaneous components. The major components were alcohols, such as, benzyl alcohol(3.79%), linalool(9.52%), terpineol(2.16%), geraniol(2.75%), nerolidol(6.50%), ketones, such as $\alpha$-ionone(1.77%), $\beta$-ionone(4.80%), geranyl acetone(1.82%) and acids, such as hexanoic acid(1.45%), nonanoic acid(1.11%).

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