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3-氰基苯甲酸甲酯的绿色合成

Synthesis of Methyl 3-Cyanobenzoate by a Green Process
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摘要 以3-醛基苯甲酸甲酯为原料,与盐酸羟胺反应后,再经脱水反应合成了3-氰基苯甲酸甲酯。考察了NaOH用量、溶剂乙醇用量、盐酸羟胺用量、脱水剂种类及用量和反应温度等条件对3-氰基苯甲酸甲酯收率的影响;并对合成产物进行了FTIR和1H NMR表征。表征结果显示,合成产物为3-氰基苯甲酸甲酯。实验结果表明,以乙酸酐为脱水剂的脱水效果较好;合成3-氰基苯甲酸甲酯的优化条件为:n(3-醛基苯甲酸甲酯)∶n(盐酸羟胺)∶n(NaOH)∶n(乙醇)∶n(乙酸酐)=1.0∶1.5∶1.8∶6.0∶1.5,脱水温度130~140℃。在此条件下,粗产品经水洗、过滤、甲醇重结晶后得黄色砂状晶体,产品纯度大于98%(w),3-氰基苯甲酸甲酯的收率可达95.1%。 Methyl 3-cyanobenzoate was synthesized from methyl 3-formylbenzoat and hydroxylamine hydrochloride by a green method including oximation reaction and dehydration reaction. The effects of sodium hydroxide dosage, solvent ethanol dosage, hydroxylamine hydrochloride dosage, dehydrating agent type and dosage and reaction temperature on the yield of methyl 3-cyanobenzoate were investigated. The end product was identified as methyl 3-cyanobenzoate by means of FTIR and ^1H NMR. The experimental results showed that under the optimum conditions of acetic anhydride as the dehydrating agent, n(methyl 3-formylbenzoate) : n(hydroxylamine hydrochloride) : n(sodium hydroxide) : n(ethanol) : n(acetic anhydride) 1.0 : 1.5 : 1.8 : 6.0 : 1.5 and dehydration temperature 130-140 ℃, the yellow crystal product with the purity higher than 98%(w) could be obtained by succedent washing, filtration and recrystallization with methanol, and the yield of methyl 3-cyanobenzoate could reach 95.1%.
出处 《石油化工》 CAS CSCD 北大核心 2013年第1期59-63,共5页 Petrochemical Technology
基金 科技部科技人员服务企业项目(2009GJD10016) 湖北省教育厅产学研重大项目(CXY2009A010) 湖北省自然科学基金重点项目(2010CDA020)
关键词 3-醛基苯甲酸甲酯 3-氰基苯甲酸甲酯 肟化反应 脱水反应 methyl 3-formylbenzoate methyl 3-cyanobenzoate oximation reaction dehydration reaction
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