Preparation Of Dibenzo-18-crown-6 With Ultrasonic Synthesis And The Study Of Its Potassium Ion Complex

Crown ethers have several types.The crown ethers,whose hetero-atom are O atom,ate classified into five kinds,such as the acyclic crown ether,the aromatic crown ether,and so on.The crown ether resins have some advantages that the crown ethers do not have.They are used in chromatogram column,counter-infiltration membrane and phase-transfer catalyzer.Dibenzo-18-crown-6(DB18C6)is one type of 18-crown-6 series.It is widely used in organic synthesis and ion complex and extraction.And it is also made into chromatography column to separate some chiral compounds.Ultrasonic synthesis is one synthetic method developing quickly in recent years. It has many advantages compared to the traditional organic synthesis.It is easier to operate and the experiment equipment is easier to control.It can raise the production rate and shorten the reaction time,and make some experiments do which are difficult to react or unable to react in traditional methods.This article prepares to synthesize DB18C6 with ultrasonic synthesis,and next to synthesize the phenolic resin of DB18C6,and potassium ion complex is synthesized, too.It needs to synthesize diethylene glycal ditosylate first.Using p- toluene sulfonyl chloride and diglycol as raw materials,we can get the product in pyridine.Then we put diethylene glycal ditosylate,catechol,potassium hydroxide and dimethylsulfoxide into a flask together in the ultrasonic reactor so as to get DB18C6.This product can be confirmed by IR,¹HNMR.Experiments of temperature,or of solvents, or of densities,or of catalyst templates,to get the best reaction condition are also done. And then to make DB18C6 reacted with formaldehyde in formic acid to get phenolic resin.And make DB 18C6 reacted with KSCN to get the complex last.The potassium ion complex is confirmed by UV,IR,conductivity and X-diffraction.From these experiments,some conclusions can be educed.1)The best condition to make DB18C6 is doing the reaction with 0.8mol·dm^-3concentration in dimethylsulfoxide with KOH as the catalyst template at 60℃in ultrasonic reactor in about 2.5 hours.The yield is 57.92%.Ultrasonic synthesis has some advantages compared to traditional synthetic methods.It is easier to operate,shorter reaction time and easier to get the product when the reaction is finished.But it is not easy to realize production,either.2)The proportion of DB18C6 and formaldehyde is 1:2 when we want to produce the linear phenolic resin.3)The complex is what we want.There is a red shift in the UV and a red shift in the IR compared to the UV and the IR of DB18C6.The theoretical number of IR corrected with the corrective gene(0.9508)is match the actual number.And the theoretical number is also indicated that potassium ion is complex well with DB18C6.