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Hydroformylation Reaction In Ionic Liquid - Water System And A New Imidazole Chiral Quaternary Ammonium Salt Of The Molecular Design And Synthesis

Posted on:2005-04-13Degree:MasterType:Thesis
Country:ChinaCandidate:Y H GongFull Text:PDF
GTID:2191360122993846Subject:Organic Chemistry
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This thesis includes two parts. The first part is study on hydroformylation of alkenes in ionic liquid-H2O system. The second part is synthesis of some imidazolium chiral quaternary ammonium salts(CQAS).Part I: we have studied the hydroformylation of butene in ionic liquid [Bmim]BF4-H20 system for the first time, and developed an excellent catalysis system: ionic liquid [Bmim]BF4 and water, mixed in ratio of 3:1, were used as solvents with RhCl3-TPPTS as catalysts. The product can be conveniently separated from the solvent-catalyst system after the reaction. The result showed that the ratio of n-aldehyde to the isomer was up to 9.1:1 with 96% ~ 98% yield. The P/Rh catalyst could be immobilized effectively in the catalyst-solvent system.The catalyst-solvent system of [Bmim]BF4/H2O/RhCl3/TPPTS was also used in the hydroformylation of 1-hexene and 1-octene, and the comparatively good results were obtained. In the hydroformylation of 1-hexene, the n/i ratio of the corresponding aldehyde was 3.6 ~ 4.5 with 92% yield while 3.2 ~ 4.3 and 67% of n/i ratio and yield, respectively, for 1-octene were obtained, and the catalyst system can be recycled 6 times.Part II: we have designed and synthesized series of new imidazolium chiral quaternary ammonium salts(CQAS):(1) Five new CQASs: the the oxalate, the chloride, and the borofluororide of (s,s)-1,3-di(a-methylbenzyl)imidazolium, the oxalate of (s)-l-H-3-(a-methyl benzyl)- imidazolium, and the bromide of (s)-l-hexadecyl-3-(a-methylbenzyi)-imidazolium. All of the structures were confirmed by EA, IR, MS, 1H-NMR and 13C-NMR.(2) Using (s)-l-hexadecyl-3-(a-methylbenzyl)- imidazolium as chiral template reagent, a kind of molecular sieve MCM-41 was successfully prepared, and the meso- hole structure was confirmed by XRD.(3) two new chiral imidazoles with big conjugate system were synthesized, that is, (s)-1-( -methylbenzyl)-2-benzene-4,5-dibenzene-imidazole and (s)-1- ( -methyl benzyI)-2-styrene-4,5-dibenzene-imidazole, whose salifying conditions were also briefly investigated.
Keywords/Search Tags:Hydroformylation
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