Synthesis Of Tetraphenol Ethane

Tetraphenol ethane is useful and important chemical products andstarting materials, owing to its excellent properties such as highsymmetry, strong rigidity and fluorescence properties. It can be rawmaterial of special epoxy resin and cyanate, curing agent of universalepoxy resin, modified agents of phenolic resin and corrosion agent tolight, and it is widely used as adhesive, electronic packaging materials,etc. However, the reaction about tetraphenol ethane and its homolog isseldom reported. In this paper, condensation reaction of phenol andglyoxal has been carried out using isopropyl alcohol as solvent in thepresence of No.732cationic exchange resin as catalyst, an effectivemethodology to analysis and calculate the yield of tetraphenol ethane wasbuilt, the reaction mechanism of tetraphenol ethane was studied, phenol,other three kinds of tetraphenolic compounds were designed andsynthesized by the reaction of glyoxal and2,6-Dimethylphenol, phenoland glutaraldehyde, glutaraldehyde and2,6-Dimethylphenol,fluorescence properties of tetraphenol ethane and its homolog wasdiscussed.1,Condensation reaction of phenol and glyoxal has been carried out using isopropyl alcohol as solvent in the presence of No.732cationicexchange resin as catalyst. An effective methodology to analysis andcalculate the yield was built under the help of combination of highperformance liquid chromatograph and mass spectrometer. With thismethod, the impacts of different react condition (ratio of phenol andglyoxal, reaction time) on ultimate yield were clarified. The result showsthat when the concentration of phenol is increased, the yield wouldincrease at first, then decreased. The yield will increase with theincreasing of reaction time from0h to32h. The maximum yield is78.8%2,This paper intend to investigate the reaction of phenol and glyoxalcatalyzed by cationic exchange resin and monitor the structures ofintermediates and final products by ESI-MS, FTIR and NMR. The resultshows that the reaction of phenol and glyoxal producesp-hydroxyphenylacetaldehyde, diphenylacetaldehyde, diphenylacetylene,triphenyl ethylene and tetraphenol ethane.1,2-Diphenyl dihydroxylethane and1,1,2-triphenyl hydroxyl ethane are not found to clarify thehydroxide group produced by the reaction of phenol and glyoxal isunstable and easy to eliminated H2O with H atom. And modified reactionmechanism of phenol and glyoxal was suggested.3,Other three kinds of tetraphenolic compounds were designed andsynthesized by the reaction of glyoxal and2,6-Dimethylphenol, phenoland glutaraldehyde, glutaraldehyde and2,6-Dimethylphenol based on the reaction mechanism of tetraphenol ethane. The result shows that theproducts the reaction of glyoxal and2,6-Dimethylphenol, phenol andglutaraldehyde, glutaraldehyde and2,6-Dimethylphenol are1,1,2,2–tetrakis (2,6-dimethyl-4-hydroxyphenyl) ethane, tetraphenol pentane and1,1,5,5-tetrakis (2,6-dimethyl-4hydroxyphenyl) pentane.4,Fluorescence properties of tetraphenol ethane and its homologwas discussed. The result shows that tetraphenol ethane has fluorescenceproperties its fluorescence emission is a series bands at about314nm,334nm and353nm. Fluorescence properties of1,1,2,2–tetrakis (2,6-dimethyl-4-hydroxyphenyl) ethane abate because of methyl replace thehydrogen of benzene ring and produce steric hindrance. Fluorescenceproperties of tetraphenol pentane abate because of introduction of longchain which destroys the coplanarity of tetraphenol ethane.