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Process On The Synthesis Of The Downstream Products Of 4,4'-Bis (Chloromethyl)-1,1'-biphenyl

Posted on:2012-07-28Degree:MasterType:Thesis
Country:ChinaCandidate:H O HeFull Text:PDF
GTID:2121330332474812Subject:Organic Chemistry
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The thesis focused on the synthesis of the downstream products of 4,4'-bis(chloromethyl)-1,1'-biphenyl, including styrene biphenyl compounds, 4,4'-bis(alkoxyl/phenoxyl-methyl)-biphenyl,4,4'-hydroxymethylbiphenyl,4,4'-biphenyl aldehyde and 4,4'-biphenyl dimethyl amines.Starting from 4,4'-bis(chloromethyl)-1,1'-biphenyl, the fluorescent brightener CBS-127 and CBS-351 was prepared through Michaelis-Arbuzov reaction and Horner-Wadsworth-Emmons reaction. The effects of solvents, alkaline, molar ratio of the reactants, temperature and work-up methods on the reaction were investigated. In Horner-Wadsworth-Emmons reaction, CBS-351 was obtained from 4,4'-bis(diethylphosphonomethyl) biphenyl(BPMB), which was used without purification, in 83% yield. The recrystallization was realized using water as solvent instead of the reported mixture of ethanol and water. A series of new styrene biphenyl compounds were also obtained with different substituted cinnamaldehyde as substrates. And the performance of their fluorescence emission spectra was compared.A series of 4,4'-bis(alkoxyl/phenoxyl-methyl)-biphenyl were prepared, taking 4,4'-bis(chloromethyl)-1,1'-biphenyl(BCMB) as raw material through Williamson ether synthesis methods. In the synthesis of 4,4'-bis(methoxyl-methyl)-biphenyl, CH3ONa was used instead of potassium hydroxylate and the reaction time was shorten from 4h to 2h, and the yield was improved from 75% to 96%. The yields of 4,4'-bis(butoxyl-methyl)-biphenyl and 4,4'-bis(phenoxyl-methyl)-biphenyl were increased by 10%-20%. And a series of new 4,4'-bis(alkoxyl/phenoxyl-methyl)-biphenyl were prepared.4,4'-hydroxymethylbiphenyl was synthesized through hydrolysis, and the effects of solvents and alkaline on the reaction were investigated.4,4'-biphenyl aldehyde was prepared through Sommelet reaction. And the reactions of 4,4'-bis(chloromethyl)-1,1'-biphenyl and amines afforded corresponding 4,4'-biphenyl dimethyl amines derivatives.
Keywords/Search Tags:4,4'-bis(chloromethyl)-l,r-biphenyl, fluorescent brighteners, Williamson ether synthesis, 4,4'-bis(alkoxy]/phenoxyl-methyl)-biphenyl, Sommelet reaction
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