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The Preparation Of Hydroxyl Octadecadienoic Acid From Reduction Of Hydroperoxy Octadecadienoic Acid

Posted on:2009-05-06Degree:MasterType:Thesis
Country:ChinaCandidate:J J ShiFull Text:PDF
GTID:2121360272456578Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
To develop a green synthetic process of hydroxyl octadecadienoic acid, the reduction of hydroperoxy octadecadienoic acid with Na2SO3 in aqueous solution to produce hydroxyl octadecadienoic acid was studied, using hydroperoxy octadecadienoic acid as the starting material that was prepared by oxidation of linoleic acid with soybean lipoxygenase as the catalyst. Two protocols were employed to enhance the solubility of the reactants and therefore to improve the product yield. Ethanol or methanol was used as the co-solvent, or, Na2CO3 was used to saponify hydroperoxy octadecadienoic acid partially. The reaction parameters were optimized. And preliminary exploration of oil hydrogen peroxide and its reduction. The main contents and results are as follows:1,The reaction parameters were optimized. Methanol as solvent system, methanol concentration of 85.8% (v/v), sulfite: hydroperoxy octadecadienoic acid (n:n)≥1, Sulfite reaction to the increase have no significant effect. 0-40℃, temperature was also no significant impact. The initial reaction (10 min less), the conversion into line with time almost up. And after 10 min,the highest conversion of hydroperoxy octadecadienoic acid has reached 98.8%. Ethanol as solvent system, alcohol concentration of 90% (v/v), sulfite: hydroperoxy octadecadienoic acid (n:n)≥1, conversion of hydroperoxy octadecadienoic acid was over 95%.2,In order to avoid solvent ethanol use, choose water as solvents, hydroperoxy octadecadienoic acid was partially saponified by sodium carbonate,which was employed to enhance the solubility of the reactants and therefore to improve the product yield. In saponify system, sodium carbonate: hydroperoxy octadecadienoic acid = 0.2:1 (n: n), sulfite: hydroperoxy octadecadienoic acid (n: n)≥1,20℃, 10min, conversion of hydroperoxy octadecadienoic acid was over 97%.3,The components of common oils such as corn oil, camellia oil, olive oil and canola oil was analysised by gas chromatograph, through which the suitable substrate with more cis,cis-1,4 - pentadiene structure can be determined. Corn oil was found to contain the highest amount in which there is 47.7% of linoleic acid, 1.9% of linolenic acid. So the corn oil was chose as the proper substrate in this enzymatic reaction.4,Synthesis of corn oil hydrogen peroxide with corn oil catalyzed by soybean lipoxygenase in aqueous phase was studied. The optimal conditions were 100 g / L of corn oil in buffer solution of pH 9 at 5 oC. The yield of corn oil hydrogen peroxide reached 54.2%. After 60 min, corn oil hydrogen peroxide reduction has been basically complete.This is the deep oil hydrogen peroxide used to provide a line of thought.
Keywords/Search Tags:Hydroperoxy octadecadienoic acid, Reduction, hydroxyl octadecadienoic acid, Soybean lipoxygenase, saponification, oil hydrogen peroxide, oxidation
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