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New Preparation Of Fine Organic Synthesis By Catalytic Oxidation

Posted on:2014-09-17Degree:MasterType:Thesis
Country:ChinaCandidate:Z B WeiFull Text:PDF
GTID:2251330425975051Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Perilla alcohol is a single-terpene monomer spices and the key intermediates of preparing perillaldehyde and Perillartine, which can also be used to synthesize agricultural pesticides and insect antifeedant.Cyclohexyl ketone compounds are an important intermediates in Spices. oxidation reactions take up an important research position in the synthesis of fragrance raw materials and pharmaceutical intermediates. To promote traditionally stoichiometric oxidation sustainable development, we explored new important synthetic methods of catalytic oxidation preparation of cyclohexenes spices. Acuqired research results as follows:1) Focus on studying the absorption separation of perillyl alcohol the isomeric product of β-pinene epoxide with HY zeoliet, activated carbon etc. The influence of adsorbent, the kind and amount of solvent, reaction temperature, reaction time were investigated in this work, especially the effects of these conditions to the adsorption separation of perillyl alcohol. The results shows that the activated carbon was stronger than other adsorbents on adsorption separation of perillyl alcohol in the isomeric product of β-pinene epoxide oil.β-pinene isomerization oil could be adsorpted by activated carbon, under room temperature, using cyclohexane as solvent. After4h perilly alcohol was adsorpted with78%of its amount and51%in the whole adsorption amount.2) Oxidation of cyclohexene catalyzed by different catalysts was carried out under mild conditions with aqueous hydrogen peroxide as the oxidant.The effects of the reaction temperature,reactiaon time,solvent type, solvent amount,and catalyst amount on the reaction were investigated. We find that c the atalytic activity of8-hydroxyquinoline oxygen vanadium is best, the allylic oxidation of cyclohexene was the dominate reaction,and cyclohexene-2-one was obtained as the major product. The solvent type significantly affect the catalyst activity and the selectivity for cyclohexene-2-one. Particularly acetone is an optimal choice for improving the conversion of cyclohexene. Under the conditions of V (acetone):V (cyclohexene)=4, n (H2O2):n (cyclohexene)=3,30℃, and24h, the conversion of cyclohexene reached up to66.9%and the selectivity for cyclohexene-2-one was84%.3)3,5,5-Trimethyl-1,2-epoxycyclohexanedione was synthesized in ethanol from a-isophorone through epoxidation under alkaline condition with hydroperoxide. The compound was rearrangment catalyzed by solid acid. The influence of reaction temperature, reaction time and reaction solvent on the rearrangment was investigated. It is found that2,3-epoxyisophorone can be converted under the mild condition. The selectivity of3,5,5-trimethyl-1,2-cyclohexanedione was89.8%from the rearrangment of the epoxides catalyzed by aluminium chloride in CH2Cl2reflux for25min.
Keywords/Search Tags:Spices, β-pinene, perilla alcohol, adsorbents, cyclohexenone, Tobacco ketone
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