Study On The Synthesis Of 3-Aryloxy-1,2-Propanediols

Petroleum resources are increasingly exhausted.The living environment in the world is deteriorating due to a lot of the mobil vehicles emission and the greenhouse gas emission.Biodiesel,which is the clean renewable,non-toxic energy and a typical "Green energy",can be as the alternative energy of petroleum to resolve the energy and environment problems.However,the high production costs restricted the development of biodiesel industry.Biodiesel is synthesized by transesterification of vegetable oils with alcohols.A large amount of glycerol is byproducts from the transesterification reaction.It is necessary to produce products with high added value in order to reduce the costs of biodiesel production and break out the bottlenecks. 3-aryloxy-1,2-propanediol is the important organic synthesis and pharmaceutical intermediate,which can be used in synthesis of 5-(aryloxymethyl)-2-oxazolidinone and so on.In the thesis the synthesis of glycidyl and 3-aryloxy-1,2-propanediol were studied.Glycidyl was synthesized by two methods.One was two-step method using glycerol as material,and another was epoxidation method using allyl alcohol as material.3-aryloxy-1,2-propanediol was synthesized from glycidyl and phenols.We studied the effects of technological conditions on synthesis reaction and discussed the synthesis mechanism of 3-aryloxy-1,2-propanediol.The results of test showed that base catalysts had greatly influences on the synthesis of glycidyl from chlorine glycerine by cyclization reaction.W/MCM-41 can effectively catalyze the oxidation from allyl alcohol and H₂O₂ to form glycidyl.The optimum conditions to form glycidyl using W/MCM-41 catalyst were as fellow:W/MCM-41 catalyst 50 mg,AAL 1 mL,H₂O₂ 2.7mL,H₂O 5mL,reaction temperature 50℃and feeding time10 h, glycidyl yield can reach 92%.The optimum conditions to form 3-aryloxy-1, 2-propanediol using cyclehexane as solvent were as fellow:NaI catalyst 30 mg,the ratio of phenol to glycidyl 1:1.2,reaction temperature 72℃and feeding time3 h, 3-phenoxy-1,2-propanediol yield can reach 76%.The results of test implied that the conversion rate and yield of different kinds of phenols reacting with glycidyl,on the whole,were better with cyclehexane as solvent,NaI as catalyst.