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Synthesis Process on Cyclic N-hydroxyl Imide Compounds

Author: WuYanBin
Tutor: CuiJianLan;YangFan
School: University of North
Course: Chemical Engineering
Keywords: N-Hydroxy succinimide N-Hydroxy maleimide N-acylation reaction hydro-xylamine hydrochloride
CLC: TQ460.1
Type: Master's thesis
Year: 2014
Downloads: 5
Quote: 0
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Abstract


N-Hydroxy succinimide are often used assynthetizing peptide, antibiotics, amino acidprotective agents, proteins as well as reaction precursors of affinity chromatography, and alsoin the diagnosis and displaying of tumour. The purity up to99%of N-Hydroxy succinimidesodium salts and potashes is usually used as chemical electroplating agent. N-Hydroxysuccinimide was synthetized by the preparation of free hydroxylamine, N-acylation reactionand closed loop dehydration reaction successively with hydroxylamine hydrochloride,triethylamine and succinic anhydride as reaction materials,1,4-diethylene dioxide asitssolvent, EDTA trisodium salt as its’ stabilizer, nhydroxybenzotirzole as its’ catalyst. Theeffect of many factors such asmaterials ratios, the use of trietylamine on the experimentalresults was observed and proceeded with process optimization. Through process optimization,the optimal process conditions was ascertained, including1,4-diethylene dioxide as solventsand dehydrant agents;1.01:1.01:1as itsmolar concentration ratio between hydroxylaminehydrochloride,trietylamineand succinic anhydride,120℃and5hours respectively as reactiontemperature and time. In such conditions, the yield of N-Hydroxy succinimide is up to87.5%and its purity is up to99.6%.Owing to N-Hydroxy maleimide with active carton-carton double bond, N-Hydroxymaleimide can be proceeded with free radicals style heated-polymerization reaction, and alsoproceeded with Michael addition reaction with all varieties of hydrogen donorseasily.Therefore, such compounds have had comprehensive application in insulation materials, hightemperature resistant materials, rubber ingredients, pesticides as well as medicineintermediates and so on. N-Hydroxy maleimide was synthetized by the preparation of freehydroxylamine, N-acylation reaction and closed loop dehydration reaction successively withhydroxylamine hydrochloride, sodium hydroxide and cis-butenedioic anhydrideas reactionmaterials, EDTAtrisodium salt as its stabilizer, a new style effective polymerization inhibitor——p-hydroxyanisole as its’ polymerization inhibitor. By the process optimization,the best optimal process conditions was attained, including water as solvents,1.03:1as itsmolar concentration ratio between hydroxylamine hydrochloride and cis-butenedioicanhydride,40℃and8hours respectively as reaction temperature and time, In such conditions,the yield of N-Hydroxy maleimide is up to56.2%and its purity is up to99.1%.

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