Synthsis Of Glucosamine And Application Of Micellar Liquid Chromato Graphy

The synthesis and characterization of glucosamine and micellar liquid chromatography(MLC)in glucosamine’analysis were studied in this thesis.Glucose as one of the most basic monosaccharide,its advantage was not only a source of cheap,but also a renewable resource.The products derived by glucose were safe,moderate,low cost,and easily degradable.Apply to such as the higher requirement for products safety and mild.As early as 1901,E.Roux got glucose(GA)with special structure from glucose oxime reduction into glucose.Glucosamine not only retained the optical structure of glucose and provided the chemical reactive group of the amino group(-NH2).That was why glucosamine could be used as biochemical and pharmaceutical intermediates.So this thsis choosed glucose which was a green renewable resource as the raw material.Synthesis of a series of glucosamines with amines.We used glucose as the material,Pd/C as the catalyst for hydrogenation reation,and synthesized N-methyl-D-glucamine,N-propyl-D-glucamine,N-butyl-D-glucamine,N-octyl-D-glucamine and N-dodecyl-D-glucamine.The reaction products were characterized by 1HNMR.This synthetic route had mild reaction conditions.The reaction temperature should be controlled between 50℃～60℃ for 2.5～4 hours,and high purity of the product was achieved.We find that,using the Pd/C catalyst,the reaction procedures were simplified,and the quality of reaction products improved.Moreover,the presence of a certain amount of water in the reaction solvent did not significantly affect the conversion rate of glucose and product purity.Using N-propyl-D-glucamine,we carried out a series of conditional experiments,and we studied the effects of molar ratio of sugar to amine,reaction time,reaction temperature,amount of catalyst and solvent on the reaction.Due to the reducing power of glucose,we could confim the end of the experiment by Fehling’s solution.The suitable experimental conditions are as follows:the molar ration of sugar to amine is 1:4;the optimum temperature for the hydrogenation reaction is 90℃;hydrogenation reaction time is 3h,and the solvent was anhydrous alcohol.Glucoseamine is a kind of important organic chemical raw materials and intermediates,mainly used in synthesis of surfants,medicine,dye,resin and so on.The detection of glucosamine is an important issue.Generally speaking,chromatography and titration method were used to detect glucosamine in reaction products.But due to the strong polarity of glucosamine and its high boiling point,traditional detection methods were insufficient.Many studies tried to find new detection methods for determing the content of glucosamine.Micellar liquid chromatography(MLC)is a reversed phase liquid chromatography with mobile phase containing surfactant above its critical micellar concentration(CMC).The determination method for amines by micellar liquid chromatography is as follows:use anionic surfactant of sodim dodecyl sulfate as micelle,and use acetic acid-sodium acetate buffer solution to adjust pH.We detected N-methyl-D-glucamine,N-propyl-D-glucamine,ethanol amines,triethanolamine in cement grinding aid.And we also studied the influence of concentration of sodium dodecyl sulfate and sodium acetate on the determination results.The results show that with the increase of SDS concentration the retention time of glucamine shortened.So was sodium acetate.The study shows that when the concentrations SDS and sodium acetate change,the retention time of glucamine changes.