4-溴-5-硝基-1,8-萘酐的合成工艺改进  被引量:2

Improvement of synthesis process of 4-bromo-5-nitro-1,8-naphthalene anhydride

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作  者:胡艳雄 吴爱斌[1] 师春甜 刘叶 舒文明 余维初[1] HU Yanxiong;WU Aibin;SHI Chuntian;LIU Ye;SHU Wenming;YU Weichu(College of Chemistry&Environmental Engineering,Yangtze University,Jingzhou 434023,Hubei,China)

机构地区:[1]长江大学化学与环境工程学院,湖北荆州434023

出  处:《精细化工》2021年第7期1500-1504,共5页Fine Chemicals

基  金:国家自然科学基金项目(21801022)。

摘  要:以苊为原料、NaBr/CeCl_(3)·7H_(2)O/H_(2)O_(2)为溴化试剂,得到5-溴苊,再用Al(NO_(3))_(3)·9H_(2)O/CH_(3)COOH硝化,得到4-溴-5-硝基苊,进一步以醋酸钴/醋酸锰/N-羟基邻苯二甲酰亚胺/氧气为氧化剂,制备得到萘酰亚胺类荧光染料的重要中间体4-溴-5-硝基-1,8-萘酐。考察了原料配比、反应温度、时间以及溶剂对收率的影响,优选的最佳反应条件为:溴化反应温度25℃,反应时间3 h,n(苊)∶n(CeCl_(3)·7H_(2)O)∶n(NaBr)=2∶1∶2.4,收率86.4%;硝化反应温度45℃,反应时间8 h,n(5-溴苊)∶n[Al(NO_(3))_(3)·9H_(2)O]=1∶1.2,收率88.4%;氧化反应温度110℃,反应时间5h,n(醋酸钴)∶n(醋酸锰)∶n(N-羟基邻苯二甲酰亚胺)∶n(4-溴-5-硝基苊)=1.2∶0.5∶1.2∶10,收率72.3%。进行了初步放大实验,结果表明,反应扩大5~20倍后仍具有较好的收率。5-Bromoacenaphthene was obtained from acenaphthene using NaBr/CeCl_(3)·7H_(2)O/H_(2)O_(2) as bromination reagent.Then,nitration reaction of 5-bromoacenaphthene with Al(NO_(3))_(3)·9H_(2)O/CH_(3)COOH to synthesize 4-bromo-5-nitroacenaphthene.Finally,4-bromo-5-nitro-1,8-naphthalene anhydride,important intermediate of naphthalimide fluorescent dyes was prepared using cobalt acetate/manganese acetate/Nhydroxyphthalimide(NHPI)/oxygen as oxidant.The effects of raw material ratio,reaction temperature,reaction time,and solvent on the yield of the product were investigated.The optimal reaction conditions were obtained.For the bromination reaction,the yield of 5-bromoacenaphthene was 86.4% under the conditions of temperature 25℃,reaction time 3 h,n(acenaphthene)∶n(CeCl_(3)·7H_(2)O)∶n(NaBr)=2∶1∶2.4,Under the conditions of temperature 45℃,reaction time 8 h,n(5-bromoacenaphthene)∶n[Al(NO_(3))_(3)·9H_(2)O]=1∶1.2,the yield of 4-bromo-5-nitroacenaphthene was 88.4%.For the oxidation reaction,when the temperature was 110℃,reaction time was 5 h,n(cobalt acetate)∶n(manganese acetate)∶n(NHPI)∶n(4-bromo-5-nitroacenaphthene)was 1.2∶0.5∶1.2∶10,the yield of 4-bromo-5-nitro-1,8-naphthalene anhydride was 72.3%.A preliminary scale-up experiment was conducted by using this method.The product yield was still high after the reaction was expanded by 5~20 times.

关 键 词: 溴化 硝化 氧化 4-溴-5-硝基-1 8-萘酐 精细化工中间体 

分 类 号:TQ241.5[化学工程—有机化工]

 

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