期刊文献+
任意字段
题名或关键词
题名
关键词
文摘
作者
第一作者
机构
刊名
分类号
参考文献
作者简介
基金资助
栏目信息

一锅法合成氧化呋咱-3,4-二甲酸二乙酯 被引量：1

Synthesis of 3,4-Bis(ethoxycarbonyl)furoxan by One-pot Method
下载PDF
导出
摘要 以乙酰乙酸乙酯为原料,经硝化、氧化、成环反应合成了氧化呋咱-3,4-二甲酸二乙酯,用红外光谱、核磁共振对其结构进行了表征。通过探讨反应机理,研究了影响反应历程的关键因素,得到最优的条件为:硝酸质量分数95%、硝化温度-10℃、乙酰乙酸乙酯与硝酸摩尔比为1.0∶1.4、催化剂与乙酰乙酸乙酯的摩尔比为1.0∶100.0、氧化剂与乙酰乙酸乙酯摩尔比为3.0∶10.0。在最优条件下收率为81.4%,纯度大于98%。 3,4-Bis（ethoxycarbonyl）furoxan was synthesized via nitration,oxidation and cyclization reaction using ethyl acetoacetate as raw material.Its structure was characterized by IR spectrometry and nuclear magnetic resonance（NMR）spectrometry.The reaction mechanism was proposed and the key factors affecting the reaction were studied,as a result,the optimal conditions obtained are as follows：mass fraction of nitric acid,95%;nitration temperature,-10℃;molar ratio of ethyl acetoacetate and nitric acid,1.0∶1.4;molar ratio of catalyst and ethyl acetoacetate,1.0∶100.0;molar ratio of oxidizer and ethyl acetoacetate,3.0∶10.0.Under the optimal conditions,the yield can reach 81.4% and the purity is higher than 98%.
作者 王敏 李斌栋
机构地区 南京理工大学化工学院
出处 《火炸药学报》 EI CAS CSCD 北大核心 2015年第1期12-15,共4页 Chinese Journal of Explosives & Propellants
关键词 有机化学 氧化呋咱-3 4-二甲酸二乙酯 乙酰乙酸乙酯 硝化 氧化腈 organic chemistry 3 4-bis（ethoxycarbonyl）furoxan ethyl acetoacetate nitration nitrile oxide
分类号 TJ55 [兵器科学与技术—军事化学与烟火技术] TQ562 [化学工程—炸药化工]
  • 相关文献

参考文献14

  • 1何金选,卢艳华,雷晴,曹一林.3,3′-二硝基-4,4′-偶氮氧化呋咱的合成及性能[J].火炸药学报,2011,34(5):9-12. 被引量：10
  • 2郭涛,刘敏,姜俊,等.3,3'-二氨基4,4'-偶氮氧化呋咱的合成方法:CN,103086997A[P].2013.
  • 3Kulikov A S, Ovchinnikov I V, Molotov S I, et al. Synthesis of furoxan derivatives based on 4-aminofu- roxan-3-carboxylie acid azid [J].Russian Chemical Bulletin, 2003, 52(8): 1822-1828.
  • 4Epishina M A, Finogenov A O, Kulikov A S, et al. Synthesis and nitration of 3 R-4-(2, 2, 2-trinitroethyl) aminofuroxans[J]. Russian Chemical Bulletin, 2012, 61(8) : 1575-1581.
  • 5Finogenov A O, Kulikov A S, Epishina M A, et al. The first synthesis of furoxan and 1,3,4-oxadiazole ring ensembles[J]. Journal of Heterocyclic Chemis- try, 2013, 50(1): 135-140.
  • 6Shimizu T, Hayashi Y, Teramura K, et al. A new synthetic method for alkyl carbonocyanidate N-oxides [J]. Bulletin of the Chemical Society of Japan, 1985, 58(9) : 2519-2522.
  • 7Makhova N N, Ovchinnikov I V, Dubonos V G, et al. Reaction of dinitrogen tetroxide with substituted dini- tromethane salts as a new method for the generation of nitrile oxides [J]. Mendeleev Communications, 1992 (3) : 91-93.
  • 8Kislyi V P, Laikhter A L, Ugrak B I, et al. Ethyl 2- nitroaceto acetate as a new synthetic equivalent of ethoxyearbonylnitrile oxide[J]. Russian Chemical Bul- letin, 1994, 43(1): 98-100.
  • 9Conti D, Rodriquez M, Sega A, et al. 1,3-Cycloaddit ion of nitrile oxides in ionic liquids. An easier route to 3 carboxy isoxazolines, potential constrained glutamic acid analogues[J]. Tetrahedron Letters, 2003, 44 (28) : 5327-5330.
  • 10Trogu E, Cecchi L, De Sarlo F, et al. Base and cop- per-catalysed condensation of primary activated nitro compounds with enolisable compounds [J]. European Journal of Organic Chemistry, 2009, 5971-5978.

二级参考文献13

  • 1Kulikov A S. Synthesis of furoxan derivatives based on 4-aminofuroxan-3 earboxylic acid azide [J]. Russian Chemical Bulletin, International Edition, 2003,52 (8) 1822- 1828.
  • 2Makhova N N, Blinnikov A N,Oveminnikov I V,et al. 4-Amino-3-azidocarbonylfuroxan as a universal synton for the synthesis of energetic compounds of the furoxan series[C]//30th Inter Annu Conf of ICT. Karlsruhe: ICT,1999,58: 1-10.
  • 3Ovchinnikov I V, Blinikov A N, Makhova N N,et al. The curtius rearrangement of azidocarbonylfuroxans: some peculiarities and the synthesis of aminofuroxans [J]. Mendeleev Communications, 1995,5 ( 2 ), 58-60.
  • 4Sikder A K,Sikder N. A review of advanced high per formance, insensitive and thermally stable energetic materials emerging for military and space applications[J]. Journal of Hazardous Materials,2004,112: 1-15.
  • 5Orakauskas V,Guest A M. Dinitromethane[J]. The Jour nal of Organic Chemistry, 1978,43(18) : 3485-3488.
  • 6Gunasekaran A ,Jayachandran T,Boyer J H,et al. A convenient synthesis of diaminoglyoxime and diaminofurazan : useful precusors for the synthesis of high density energetic materials [J]. J Heterocyclic Chem, 1995,32:1405.
  • 7Kulikov A S, Ovchinnilov I V. Synthesis of furoxan derivatives based on 4-aminofuroxan-3-carboxylic acid azide[J]. Russian Chemical Bulletin, 2003,52(8) : 1822-1828.
  • 8Nina N Makhova, Alexander N Blinnikov. 4-Amino-3-azidocarbonylfuroxan as an universal syntol for the synthesis of energetic compounds of the furoxan series[C]//30th Int. Annu. Conf. of ICT. 1999.
  • 9Ovchinnilov I V, Kulikov A S. The Curtius rearrangement of azidocarbonylfuroxan: Some peculiarities and the synthesis of aminofuroxans [J]. Mendeleev Commun,1995,(2):58-60.
  • 10Lobbecke S, Schuppler H, Schweikert W. Thermal properties of different substituted energetic furoxans[C]//33th Int. Annu. Conf.of ICT. 2002.

共引文献10

同被引文献36

  • 1张静,王莅,苏敏,张香文,米镇涛.无水硝酸中N_2O_4和N_2O_5含量的分析[J].含能材料,2006,14(1):62-65. 被引量：2
  • 2钱华,吕春绪,叶志文.绿色硝化剂五氧化二氮及其在硝化反应中的应用[J].精细化工,2006,23(6):620-624. 被引量：20
  • 3VASS G, DZSOTJAN D, LAJGUT G G, et al. Photoelectron spectroscopic investigation of the electronic structure of furoxans[J]. European ChemicalBulletin, 2012, 1 (1/2): 22-26.
  • 4FRANK I, HAMMERLA, KLAPOTKE T, et al. Processes during the hypergolic ignition between monomethylhydrazine (MMH) and dinitrogen tetroxide (N204) in rocket engines[J]. Propellants, Explosives, Pyrotechnics, 2005, 30 (1): 44-52.
  • 5PAKDEHI S G, ATDARI S, HASHEMI A, et al. Performance evaluation of liquid fuel 2-dimethyl amino ethyl azide (DMAZ) with liquid oxidizers[J]. Journal of Energetic Materials, 2015, 33 ( 1 ): 17-23.
  • 6TRIPATHY S, VINOKOUR E, MCMAHONK M, et al. High-density lipoprotein nanoparticles deliver RNAi to endothelial cells to inhibit angiogenesis[J]. Particle & Particle Systems Characterization, 2014, 31: 1141-1150.
  • 7YAMAMOTO H, HORⅡ F, HIRAI A.Structural studies of bacterial cellulose through the solid-phase nitration and acetylation by CP/MASl3CNMRspectroscopy[J].Cellulose, 2006, 13: 327-342.
  • 8DUDDU R G, DAVE P R.Processes and compositions for nitration of N-substituted isowurtzitane compounds with concentrated nitric acid at elevated temperatures to form HNIW and recovery of gamma HNIW with high yields and purities: US6015898[P],2000-01-18.
  • 9WATSON W E, GLENN J W.Mamffacture of nitric acid: US2486083 [P]. 1949-10-25.
  • 10COON C L.Preparation of anhydrous nitric acid US3981975[P],1976-09-21.

引证文献1

火炸药学报
2015年 第1期

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部