• Title/Summary/Keyword: n-alcohols

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TMEDA: Efficient and Mild Catalyst for the Acylation of Alcohols, Phenols and Thiols under Solvent-free Condition

  • Kadam, Santosh T.;Lee, Han-Bin;Kim, Sung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.30 no.5
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    • pp.1071-1076
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    • 2009
  • N,N,N′,N′-tetramethylethylenediamine (TMEDA) acts as a simple, mild and efficient catalyst for the acylation of alcohols, phenols and thiols at room temperature under solvent-free condition. Acylation reaction with acetic anhydride and benzoic anhydride proceeds with good to excellent yield in the presence of TMEDA as the catalyst.

Higher Alcohols composition in Korean Alcoholic Beverages (국내산 증류주의 고급 알콜 조성에 관하여)

  • 이해금;최용순;정의호
    • Journal of Food Hygiene and Safety
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    • v.4 no.3
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    • pp.257-261
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    • 1989
  • In order to evaluate the characteristics and quality of various Korean alcoholic beverage, the higher alcohols profiles were analyzed by gas-chromatography. Total amount of the higher alcohols depended on the type and class of the liquors. Gaschromatographic analysis showed that the type of Gin, Rum and Vodka except for SB contain n-propanol mainly. The amount of the higher alcohols determined was proportional to the content of the originally fermented liquor in the whisky. The difference in the ratio of iso-amyl alcohol content to that of iso-butanol may be useful as a parameter in evaluating the class of the whisky.

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Reorientational Motion of N-Ethylacetamide in n-Alcohols (알코올 용액에서의 N-에틸아세트아미드의 재배향 운동)

  • Kwon Sun-Ki;Lee Kang Bong;Choi Young-Sang;Yoon Chang-Ju
    • Journal of the Korean Chemical Society
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    • v.37 no.1
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    • pp.43-48
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    • 1993
  • The $^1H-NMR$ spectra of the NH-group were obtained for N-ethylacetamide (NEAA) in the series of n-alcohols over a temperature range of 310∼350K by using NMR spectroscopy. The $^1H-NMR$ lineshape coupled to $^{14}N$ nucleus were analyzed to obtain the reorientational correlation times ${\tau}_c$ of NEAA. The data indicate that the coupling of solute and solvent decreases as the chain length of n-alcohols increases. But in the n-alcohols the reorientational motion depends almost linearly on η/T of solvents over our temperature range. The results are discussed in the context of the subslip phenomenon.

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Purification and Characterization of NAD-Dependent n-Butanol Dehydrogenase from Solvent-Tolerant n-Butanol-Degrading Enterobacter sp. VKGH12

  • Veeranagouda, Y.;Benndorf, Dirk;Heipieper, Hermann J.;Karegoudar, T.B.
    • Journal of Microbiology and Biotechnology
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    • v.18 no.4
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    • pp.663-669
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    • 2008
  • The solvent-tolerant bacterium Enterobacter sp. VKGH12 is capable of utilizing n-butanol and contains an $NAD^+$-dependent n-butanol dehydrogenase (BDH). The BDH from n-butanol-grown Enterobacter sp. was purified from a cell-free extract (soluble fraction) to near homogeneity using a 3-step procedure. The BDH was purified 15.37-fold with a recovery of only 10.51, and the molecular mass estimated to be 38 kDa. The apparent Michaelis-Menten constant ($K_m$) for the BDH was found to be 4 mM with respect to n-butanol. The BDH also had a broad range of substrate specificity, including primary alcohols, secondary alcohols, and aromatic alcohols, and exhibited an optimal activity at pH 9.0 and $40^{\circ}C$. Among the metal ions studied, $Mg^{2+}$ and $Mn^{2+}$ had no effect, whereas $Cu^{2+},\;Zn^{2+}$, and $Fe^{2+}$ at 1 mM completely inhibited the BDH activity. The BDH activity was not inhibited by PMSF, suggesting that serine is not involved in the catalytic site. The known metal ion chelator EDTA had no effect on the BDH activity. Thus, in addition to its physiological significance, some features of the enzyme, such as its activity at an alkaline pH and broad range of substrate specificity, including primary and secondary alcohols, are attractive for application to the enzymatic conversion of alcohols.

Effects of n-Alcohols on the Amino-Proton Chemical Shift and on the Hindered Rotation About N-C (S) Bond of Thioacetamide (Thioacetamide의 아미노 양성자의 화학적 이동과 N-C (S) 결합 주위의 부자유 회전에 미치는 n-알코올 용매 효과)

  • Jong-Ho Choi;Young-Sang Choi;Chang-Ju Yoon
    • Journal of the Korean Chemical Society
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    • v.33 no.2
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    • pp.149-155
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    • 1989
  • 1H-nmr chemical shifts and lineshapes of amino-protons of thioacetamide in n-alcohols were determined. The chemical shifts are discussed by the Reichardt's solvent polarity parameter, $E_T(30)$. The following relationship between ${delta}_{obs}\;and\;E_T(30)$ was obtained, ${\delta}_{obs}=a{\cdot}E_T(30)+b{\cdot}(E_T(30))_2$ where a is a characteristic constant for the protons of thioacetamide in n-alcohol solutions and b is a constant for the solute(TA)-solvent (n-alcohols) interactions. The barrier of the hindered rotation about the N-C(S) bond in TA was obtained by analysis of the lineshape of the amino-protons in TA. The behavior of the hindered rotation as well as chemical shifts of the amino-protons in TA has been found to be closely related to the $E_T(30)$ of n-alcohols.

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Effects on n-Alcohols on the Amino-Proton Chemical Shifts and on the Hindered Rotation about the N-C(O) Bond of Acetamide (아세트아미드의 아미노 양성자의 화학적 이동과 N-C(O) 결합주위의 부자유회전에 미치는 n-알코올 용매 효과)

  • Gwon, Sun Gi;Choe, Jong Ho;Choe, Yeong Sang;Yun, Chang Ju;Gwon, Dae Geun
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.509-516
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    • 1990
  • 1H-nmr chemical shifts and lineshapes of amino-protons of acetamide (AA) in n-alcohols were determined. The chemical shifts are discussed by the Reichardt's solvent polarity parameter, E$_{T}$(30). The following relationship between $\delta$obs and E$_{T}$(30) was obtained. ${\delta}_{obs}$ = ${\delta}_{o}$ + aE$_{T}$ (30) + b[E$_{T}$(30)]$^2$ where ${\delta}_{o}$ is the chemical shift of the solute in gaseous state or at $E_{T}$(30) = 0, a is a characteristic constant for the protons of AA in n-alcohol solutions and b is a constant for the solute (AA)-solvent (n-alcohols) interaction. The barrier of the hindered rotation about the N-C(O) bond in AA was obtained by analysis of the lineshapes of the amino-protons in AA. The behavior of the internal rotation as well as chemical shifts of the amino-protons in AA has been found to be closely related to the $E_{T}$(30) of n-alcohols.

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Reaction of Lithium n-Butylborohydride with Selected Organic Compounds Containing Representative Functional Groups

  • Chong-Suh Pyun;Jong-Chan Son;Nung-Min Yoon
    • Bulletin of the Korean Chemical Society
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    • v.4 no.1
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    • pp.3-9
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    • 1983
  • Lithium n-butylborohydride was prepared from borane-dimethylsulfide (BMS) and n-butyllithium, and the approximate rates and stoichiometrics of its reactions with selected organic compounds containing representative functional groups were studied in THF at room temperature. Phenol and benzenetiol liberated hydrogen quickly and quantitatively, and the reactions of primary alcohols, 2,6-di-ter-butylphenol and 1-hexanethiol liberated hydrogen quantitatively within 3 hrs, whereas the reactions of secondary and tertiary alcohols were very slow. Aldehydes and ketones were reduced rapidly and quantitatively to the corresponding alcohols. Cinnamaldehyde utilized 1 equiv. of hydride rapidly, suggesting the reduction to cinnamyl alcohol. Carboxylic acids evolved 1 equiv. of hydrogen rapidly and further reduction was not observed. Anhydrides utilized 2 equiv. of hydride rapidly but further hydride uptake was very slow, showing a half reduction. Acid chlorides were reduced to the alcohol stage very rapidly. All the esters examined were reduced to the corresponding alcohol rapidly. Lactones were also reduced rapidly. Expoxides took up 1 equiv. of hydride at a moderate rate to be reduced to the corresponding alcohols. Nitriles and primary amides were inert to this hydride system, whereas tertiary amide underwent slow reduction. Nitroethane and nitrobenzene were reduced slowly, however azobenzene and azoxybenzene were quite inert. Cyclohexanone oxime evolved 1 equiv. of hydrogen rapidly, but no further reduction was observed. Phenyl isocyanate and pyridine N-oxide were proceeded slowly, showing 1.74 and 1.53 hydride uptake, respectively in 24 hours. Diphenyl disulfide was reduced rapidly, whereas di-n-butyl disulfide, sulfone and sulfonic acids were inert or sluggish. n-Hexyl iodide and benzyl bromide reacted rapidly, but n-octyl bromide, n-octyl chloride, and benzyl chloride reacted very slowly.

A Study on Explosive Limits of Flammable Materials - Prediction of Explosive Properties and Temperature Dependence of Explosive Limits for n-Alcohols - (가연성물질의 폭발한계에 관한 연구 -알코올화합물의 폭발특성치 및 폭발한계의 온도의존성 예측-)

  • 하동명
    • Journal of the Korean Society of Safety
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    • v.14 no.1
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    • pp.93-100
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    • 1999
  • By using literature data, the empirical equations have been derived which describe the interrelationships of explosion and other related properties of n-alcohols. The properties which have been correlated data are : lower and upper explosive limits, heats of combustion, carbon numbers. Also, the new equation for predicting the temperature dependence of lower explosive limits(LEL) of n-alcohols on the basis of explosive limits, heats of combustion, flame propagation theory and mathematical method is proposed. The values calculated by the proposed equations were a good agreement with literature data within a few percent. From a given explosive properties. by using the proposed equations, it is possible to predict the other properties. It is hoped eventually that this method will permit the estimation of the explosive properties of alcohol with improved accuracy and the broader application for other compounds.

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Prediction of Upper Explosion Limits(UEL) by Measurement of Upper Flash Point Using Setaflash Apparatus for n-Alcohols (Setaflash 장치를 이용한 노말 알코올류의 상부인화점 측정에 의한 폭발상한계의 예측)

  • Ha, Dong-Myeong
    • Journal of the Korean Society of Safety
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    • v.25 no.2
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    • pp.35-40
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    • 2010
  • Explosion limit and flash point are the major combustion properties used to determine the fire and explosion hazards of the flammable substances. In this study, in order to predict upper explosion limits(UEL), the upper flash point of n-alcohols were measured under the VLE(vapor-liquid equilibrium) state by using Setaflash closed cup tester(ASTM D3278). The UELs calculated by Antoine equation using the experimental upper flash point are usually lower than the several reported UELs. From the given results, using the proposed experimental and predicted method, it is possible to research the upper explosion limits of the other flammable substances.

Mixed Micellar Properties of Cetylpyridinium Chloride(CPC) with Triton X-100(TX-100) in Aqueous Solutions of n-Alcohols (n-알코올 수용액에서 Cetylpyridinium Chloride(CPC)와 Triton X-100(TX-100)의 혼합미셀화에 대한 연구)

  • Chung, Jong Jae;Kim, Yung Cheol;Lee, Yung Cheol
    • Journal of the Korean Chemical Society
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    • v.41 no.6
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    • pp.284-291
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    • 1997
  • The critical micelle concentrations($CMC^*$) of a cationic surfactant cetylpyridinium chloride (CPC) and a nonionic surfactant triton X-100(TX-100) in aqueous solutions of n-alcohols(methanol, ethanol, 1-propanol, 1-butanol and 1-pentanol) were determined by UV spectroscopic method at 25$^{\circ}C$. The various thermodynamic values in 0.1 M n-alcohols were calculated by means of the equation derived from the pseudo-phase separation model and compared with the values in the absence of n-alcohols. The results were a good agreement with the nonideal mixed micelle model, and they showed negative deviation from the ideal behavior.

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