微反应器在硝化反应中的应用
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摘要
硝化反应在农药、炸药、染料、香水以及活性药物中间体等的合成中占有重要地位,但目前工业上普遍采用间歇式操作,其生产过程中存在放热量大、选择性低、危险性高、环境污染、资源浪费等问题。微反应器作为高效、安全、环保、操作性强的新型反应设备,可凭借良好的传质、传热性能解决以上问题,同时可通过增加反应器数量进行放大,节省放大时间和成本。因此,对微反应器的特点进行了简单介绍,并针对微反应器在硝化反应中的具体应用做简要概述。
Nitration plays an important role in the synthesis of pesticides,explosives,dyes,perfumes and pharmaceutical intermediates,but it has some problems such as large heat release,high risk,low selectivity,environmental pollution and waste of resources.Microreactor is an emerging chemical reacting equipment with high efficiency,safety,high maneuverability,and environmental friendliness.It can solve these problems with its good mass transfer and heat transfer performance. As well as,its amplification mode of increasing the number of reactors also saves amplification time and cost.This article introduced the microreactor and gave a brief overview of the application of microreactors in nitration.
Nitration plays an important role in the synthesis of pesticides,explosives,dyes,perfumes and pharmaceutical intermediates,but it has some problems such as large heat release,high risk,low selectivity,environmental pollution and waste of resources.Microreactor is an emerging chemical reacting equipment with high efficiency,safety,high maneuverability,and environmental friendliness.It can solve these problems with its good mass transfer and heat transfer performance. As well as,its amplification mode of increasing the number of reactors also saves amplification time and cost.This article introduced the microreactor and gave a brief overview of the application of microreactors in nitration.
引文
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[4]陈光岩,李牧松,王英.过程强化技术在连续聚合工艺中的应用进展[J].化工科技,2017,25(2):76-80.
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[7]MARC E G,TIMOTHY N,VOLKER H. Microflow highp,T intensification of vitamin D3 synthesis using an ultraviolet lamp[J].Org.Pro.Res.Dev.,2018,22(2):147-155.
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[17]韩非.并流式微反应器中叔胺裂解、芳烃硝化反应的研究[D].杭州:浙江工业大学,2008.
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[25]DUEHR J. Nitration technology for aromatics as described in the patent literature[J]. ACS Symp. Ser.,2013,1 155(22):71-82.
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[29]张跃,张菁,辜顺林,等.微通道中硝基胍的连续流合成[J].精细化工,2016,33(8):946-950.
[30]CHEN Mao,BUCHWALD S L.Continuous-flow synthesis of 1-substituted benzotriazoles from chloronitrobenzenes and amines in a C—N bondformation/hydrogenation/diazotization/cyclization sequence[J]. Angew. Chem. Int.Ed.,2013,52(15):3 434-3 437.
[31]ANDRW R B,SARAH L P,DANIEL C,et al.The continuous-flow synthesis of ibuprofen[J].Angew.Chem.Int.Ed.,2009,48(45):8 547-8 550.
[32]ADAMO A,BEINGESSNER R L,BEHNAM M,et al.On-demand continuous-flow production of pharmaceuticals in a compact,reconfigurable system[J]. Science,2016,352(6 281):61-67.
[33]LIN Hong-kun,DAI Chun-hui,JAMISON T F,et al. A rapid total synthesis of ciprofloxacin hydrochloride in continuous flow[J]. Angew. Chem. Int. Ed.,2017,56(30):8 870-8 873.
[34]王锋,李隆键,崔文智,等.微反应中甲醇-水蒸气重整制氢三维模拟[J].重庆大学学报,2007,30(2):26-41.
[35]葛皓,陈光文,袁权,等.微反应器内甲苯气相催化氧化反应动力学[J].化工学报,2007,58(8):1 967-1 972.
[36]GLOTZ G,KNOECHEL D J,PODMORE P,et al.Reaction calorimetry in microreactor environments-measuring heat of reaction by isothermal heat flux calorimetry[J].Org.Pro.Res.Dev.,2017,21(5):1-19.
[2]王乐夫,张美英,李雪辉,等.微化学工程中的微反应技术[J].化学反应工程与工艺,2001,17(2):175-180.
[3]刘冠颖,方玉诚,郭辉进.微反应器发展概况[J].当代化工,2010,39(3):315-318.
[4]陈光岩,李牧松,王英.过程强化技术在连续聚合工艺中的应用进展[J].化工科技,2017,25(2):76-80.
[5]BRIAN P M,KRISTIN E P,JEREMY L S,et al.Greener approaches to organic synthesis using microreactor technology[J].Chem.Rev.,2007,107(6):2 300-2 318.
[6]CAYGILL G,ZANFIR M,GAVRIILIDIS A.Scalable reactor design for pharmaceutical and fine chemicals production:potential scale-up obstacles[J]. Org. Pro. Res. Dev.,2006,10(3):539-552.
[7]MARC E G,TIMOTHY N,VOLKER H. Microflow highp,T intensification of vitamin D3 synthesis using an ultraviolet lamp[J].Org.Pro.Res.Dev.,2018,22(2):147-155.
[8]KULKARNI A A,NIVANGUNE N T.Continuous flow nitration of salicylic acid[J]. Org. Pro. Res. Dev.,2008,12(5):995-1 000.
[9]ANDREOZZI R,CANTERINO M,CAPRIO V,et al.Salicylic acid nitration by means of nitric acid/acetic acid system:chemical and kinetic characterization[J]. Org.Pro.Res.Dev.,2006,10(6):1 199-1 204.
[10]DOMINIQUE R,LAURENT D.Nitration of activated aromatics in microreactors:WO,2 007 087 816A1[P].2007-08-09.
[11]KULKARNI A A,KALYANI V S,JOSHI R A,et al.Continuous flow nitration of benzaldehyde[J]. Org. Pro.Res.Dev.,2009,13(5):999-1002.
[12]滕裕翔.微反应器中绿色硝化合成二甲戊乐灵的工艺研究[D].南京:南京理工大学,2015.
[13]CHEN Yi-zheng,ZHAO Yu-chao,HAN Mei,et al.Safe,efficient and selective synthesis of dinitroherbicides via a multifunctional continuous-flow microreactor:one-step dinitration with nitric acid as agent[J]. Green Chem.,2013,15(1):91-94.
[14]LAURENT D,DOMINIQUE M R.Controlled autocatalytic nitration of phenol in a microreactor[J].Angew.Chem.Int.Ed.,2005,44(48):7 972-7 975.
[15]GAGE J R,GUO Xiao-wen,TAO Jian,et al.High output continuous nitration[J]. Org. Pro. Res. Dev.,2012,16(5):930-933.
[16]PANKE G,SCHWALBE T,STIRNER W,et al.A practical approach of continuous processing to high energetic ntiration reactions in microreactors[J]. Synthesis,2003,18(18):2 827-2 830.
[17]韩非.并流式微反应器中叔胺裂解、芳烃硝化反应的研究[D].杭州:浙江工业大学,2008.
[18]朱翔.微通道反应器中3,4-二硝基吡唑合成工艺研究[D].南京:南京理工大学,2017.
[19]PELLETER J,RENAUD F.Facile,fast and safe process development of nitration and bromination reactions using continuous flow reactors[J]. Org. Pro. Res. Dev.,2009,13(4):698-705.
[20]SCHWEIKERT W,TURCKE T,LOBBECKE S,et al.Monitoring of nitration reactions in microreactors with FTIR microscopy[A]. The symposium of 31stinternational annual conference of ICT[C]. Pfinztal:Energetic Materials,2000.
[21]LOBBECKE S,ANTES J,TURCKE T,et al.The potential of microreactors for the synthesis of energetic materials[A].The symposium of 31stinternational annual conference of ICT[C].Pfinztal:Energetic Materials,2000.
[22]马晓明.N2O5硝化硝解反应研究[D].南京:南京理工大学,2013.
[23]SHEN Jian-ni,ZHAO Yu-chao,CHEN Guang-wen,et al.Investigation of nitration processes of iso-octanol with mixed acid in a microreactor[J]. Cat. Kinet. React.,2009,17(3):412-418.
[24]韩骏奇,孟子晖,孟文君,等.微反应器中合成硝酸酯炸药[J].含能材料,2010,18(1):34-36.
[25]DUEHR J. Nitration technology for aromatics as described in the patent literature[J]. ACS Symp. Ser.,2013,1 155(22):71-82.
[26]TUERCKE T,MENDLA,BOSKOVIC D,et al.Save and continuous synthesis of nitrate esters in an automated microreaction plant[A].The symposium 41stinternational annual conference of ICT[C].Pfinztal:Energetic Materials,2010.
[27]ANTES J,JANITSCHEK W,SCHULZ N,et al.Continuous flow synthesis of DNDA57 in a capillary microreactor[A].The symposium of 43rdinternational annual conference of ICT[C].Pfinztal:Energetic Materials,2012.
[28]ANTES J,SCHWARZER M,JANITSCHEK W,et al. A novel approach to DNDA57 synthesis by microreaction technology[A]. The symposium of 41stinternational annual conference of ICT[C]. Pfinztal:Energetic Materials,2010.
[29]张跃,张菁,辜顺林,等.微通道中硝基胍的连续流合成[J].精细化工,2016,33(8):946-950.
[30]CHEN Mao,BUCHWALD S L.Continuous-flow synthesis of 1-substituted benzotriazoles from chloronitrobenzenes and amines in a C—N bondformation/hydrogenation/diazotization/cyclization sequence[J]. Angew. Chem. Int.Ed.,2013,52(15):3 434-3 437.
[31]ANDRW R B,SARAH L P,DANIEL C,et al.The continuous-flow synthesis of ibuprofen[J].Angew.Chem.Int.Ed.,2009,48(45):8 547-8 550.
[32]ADAMO A,BEINGESSNER R L,BEHNAM M,et al.On-demand continuous-flow production of pharmaceuticals in a compact,reconfigurable system[J]. Science,2016,352(6 281):61-67.
[33]LIN Hong-kun,DAI Chun-hui,JAMISON T F,et al. A rapid total synthesis of ciprofloxacin hydrochloride in continuous flow[J]. Angew. Chem. Int. Ed.,2017,56(30):8 870-8 873.
[34]王锋,李隆键,崔文智,等.微反应中甲醇-水蒸气重整制氢三维模拟[J].重庆大学学报,2007,30(2):26-41.
[35]葛皓,陈光文,袁权,等.微反应器内甲苯气相催化氧化反应动力学[J].化工学报,2007,58(8):1 967-1 972.
[36]GLOTZ G,KNOECHEL D J,PODMORE P,et al.Reaction calorimetry in microreactor environments-measuring heat of reaction by isothermal heat flux calorimetry[J].Org.Pro.Res.Dev.,2017,21(5):1-19.