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남희영 중앙대학교 교육대학원 2008 국내석사
diaryl ether is a compound used importantly as natural products in the medical profession. However, the metal oxidizer, a catalyst which is used in synthesis process, should be added stoichiometrically the precise quantity, and dealing with it causes several problems because of much metal oxidizer and dangerous inorganic compounds. In this paper developed an easy and new synthetic process. This synthesis process that using various benzyl alcohol compounds with BF3·Et2 is reacting as one-pot. diaryl ether 화합물은 의학계 등에서 natural products로서 중요한 역할을 하는 화합물이지만 합성 과정 중 사용되는 촉매인 금속 산화제들은 화학 양론(stoichiometric)적으로 정량만을 사용해야 하고 위험하고 독성이 있는 무기, 금속 산화제가 많아 다루는 데 여러 문제가 있을 뿐만 아니라, 부가적으로 생성되는 결과물을 분리하는데 어려움이 있다. 본 연구에서는 청정화학(Green chemistry)으로써 각광받고 있는 환경 친화적인 이온성 액체인 [bmim]BF4를 이용하여 다양한 벤질 알코올 화합물이 BF3·OEt2에 의해 one-pot으로 반응이 진행되고, 보다 쉽게 촉매로부터 반응물인 diaryl ether를 분리할 수 있는 간편하고 새로운 합성법을 개발하였다.
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이온성 액체와 아이오딘-탄산리튬을 이용한 벤질 알코올의 효과적인 산화 반응
알코올에서 카보닐 화합물로의 산화반응은 유기합성 화학 분야에서 기초적인 유기적 변화로 알려지고 있다. 벤질 알코올을 benzaldehyde나 aryl ketone으로 산화시키는 여러 가지 방법은 발전되고 있지만 주로 알려진 기존의 방법들은 조작의 어려움, 긴 반응시간, 그리고 유독한 시약의 사용 등과 같은 여러 단점이 있다. 그래서 benzylic oxidation 반응은 아직까지도 높은 안정성과 낮은 독성, 유용성을 필요로 하고 있다. The oxidation of alcohols to carbonyl compounds has been recognized as a fundamental organic transformation in synthetic chemistry. Various methods have been developed for the oxidation of benzyl alcohols to the corresponding benzaldehyde or acetophenone. However, the majority of known methods commonly suffer from one or more disadventages such as difficulty in manipulation, long reaction times, and utilization of toxic reagents. Therefore, it is still desirable to develop a new efficient oxidant with properties of high stability, low toxicity, and ready availability for the benzylic oxidation.
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The dyeing properties of wool fiber pretreated with benzyl alcohol was investigated. The dyeing experiments were preferred using C.I Acid Orange 7 at 80℃, pH 4.2. The dye uptake of pretreated wool was increased compared to that of scoured wool. The increase of dye uptake of pretreated wool is attributed to the removal of scale which is the surface barrier of dye diffusion. The dye uptake is changed with pretreatment temperature and time of benzyl alcohol. The action of benzyl alcohol on solvent-assisted dyeing is considerably due to some of disaggregation of dye in aqueous solution.
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알코올-물 혼합용매계에서 4-치환된 벤질 유도체의 반응성-선택성에 대한 반응속도 모델
For solvolyses of various benzyl substrates in ethanol-water (EW) and methanol-water (MW) mixtures, product selectivities (S) are reported for chlorides at 75 ˚C defined as follows using molar concentrations: S = ([ether product]/[alcohol product]) x ([water]/[alcohol solvent]). The results support earlier evidence that solvolyses of 4-nitrobenzyl substrates are S_(N)2 processes, which are not susceptible to mechanistic changes over the whole range of solvents from water to alcohol. S values at 25 and/or 45 ˚C in EW and MW, and additional kinetic data including kinetic solvent isotope effects (KSIE) are reported for solvolyses of 4-nitrobenzyl mesylate and tosylate. A kinetic model, explaining both rates and product, is proposed; a general medium effect due to solvent polarity is combined in one parameter with solvent effects on the nucleophilicity of the water and alcohol molecules acting as nucleophiles in S_(N)2 reactions. According to this model, as alcohol is added to water the rate of reaction decreases due to a decrease in solvent polarity, but the nucleophilicity of water increases relative to alcohol. The availability of experimental rate and product data over the whole range of solvent compositions from alcohol to water, reveals limitations of alternative approaches using activities.
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