微反应器内连续重氮化/偶合反应进展
|
摘要
微反应器一般是指通过微加工和精密加工技术制造的小型反应器,其为微化工技术的核心部件之一。与传统的釜式反应器相比,微反应器具有很大的优势,顺应了高技术含量和可持续发展的要求。在化学化工、材料、生物等诸多领域的研究和生产过程中,微反应器都有着广泛的应用前景,这其中一大部分涉及到了危险或不稳定物质的合成过程及高放热反应过程等。本文主要介绍了国内外利用微反应器技术进行重氮化反应连续化的研究进展,以及利用微反应器进行连续重氮化/偶合反应合成偶氮染料及颜料的研究进展。微反应器技术使化学反应过程变得更快速、更安全、更环保,所以具有很高的工业应用价值,也是化工领域未来的发展方向之一。
Microreactor is generally referred to a mini-reactor made by microfabrication and precision machining technology. It is one of the core components of microchemical technology. Compared with the traditional batch reactor, the microreactor has many advantages, which complies with the requirements of high technology content and sustainable development. In chemical engineering, materials, biology and many other fields of research and production process, the microreactor has a broad application. It involves the synthesis process of the dangerous or unstable chemical compounds and the high exothermic reaction process. In this paper, two parts are introduced respectively, involving the research progress of continuous diazotization and continuous diazotization/coupling reaction for synthesis of azo dyes and azo pigments. The microreactor technology makes the chemical reaction process become faster, safer and more environmentally friendly, so it has high industrial application value and is one of the future development directions of the chemical industry.
Microreactor is generally referred to a mini-reactor made by microfabrication and precision machining technology. It is one of the core components of microchemical technology. Compared with the traditional batch reactor, the microreactor has many advantages, which complies with the requirements of high technology content and sustainable development. In chemical engineering, materials, biology and many other fields of research and production process, the microreactor has a broad application. It involves the synthesis process of the dangerous or unstable chemical compounds and the high exothermic reaction process. In this paper, two parts are introduced respectively, involving the research progress of continuous diazotization and continuous diazotization/coupling reaction for synthesis of azo dyes and azo pigments. The microreactor technology makes the chemical reaction process become faster, safer and more environmentally friendly, so it has high industrial application value and is one of the future development directions of the chemical industry.
引文
[1]陈光文,袁权.微化工技术[J].化工学报,2003,54(4):427-439.CHEN G W,YUAN Q.Micro-chemical technology[J].Journal of Chemical Industry and Engineering(China),2003,54(4):427-439.
[2]郑亚峰,赵阳,辛峰.微反应器研究与展望[J].化工进展,2004,23(5):461-466.ZHENG Y F,ZHAO Y,XIN F.Research and prospects of microreactors[J].Chemical Industry and Engineering Progress,2004,23(5):461-466.
[3]刘兆利,张鹏飞.微反应器在化学化工领域中的应用[J].化工进展,2016,35(1):10-17.LIU Z L,ZHANG P F.Applications of microreactor in chemistry and chemical engineering[J].Chemical Industry and Engineering Progress,2016,35(1):10-17.
[4]BOU-DIAB L,FIERZ H,GWERDER C,et al.A new multipurpose microreactor for process safety studies[J].Organic Process Research&Development,2003,7:1077-1078.
[5]MO F Y,DONG G B,ZHANG Y,et al.Recent applications of arene diazonium salts in organic synthesis[J].Org.Biomol.Chem.,2013,11:1582-1593.
[6]DEADMAN B J,COLLINS S G,MAGUIRE A R.Taming hazardous chemistry in flow:the continuous processing of diazo and diazonium compounds[J].Chem.Eur.J.,2015,21:2298-2308.
[7]MULLER S T R,WIRTH T.Diazo compounds in continuous-flow technology[J].ChemSusChem.,2015,8:245-250.
[8]SHUKLA C A,KULKARNI A A,RANADE V V.Selectivity engineering of the diazotization reaction in a continuous flow reactor[J].React.Chem.Eng.,2016,1:387-389.
[9]PARTINGTON S,WALDRAM S P.Runaway reaction during production of an azo dye intermediate[J].Trans IChemE.,2002,80:33-39.
[10]WOOTTON R C,FORTT R,DE MELLO A J,et al.On-chip generation and reaction of unstable intermediates-monolithic nanoreactors for diazonium chemistry:azo dyes[J].Lab Chip,2002,2:5-7.
[11]WOOTTON R C,FORTT R,DE MELLO A J.Continuous-flow generation of anhydrous diazonium species:monolithic microfluidic reactors for the chemistry of unstable intermediates[J].Organic Process Research&Development,2003,7:762-768.
[12]ATTOMA J D,CAMARA T,ROUTIER S,et al.Efficient transposition of the Sandmeyer reaction from batch to continuous process[J].Org.Process Res.Dev.,2017,21:44-51.
[13]KARNEY M J,PORTER K A,VANIER G S,et al.Meso-scale microwave-assisted continuous flow reactions utilizing a selective heating matrix[J].RSC Advances,2013,3:7106-7111.
[14]MALET-SANZ L,MADRZAK J,HOLVEY R S,et al.A safe and reliable procedure for the iododeamination of aromatic and heteroaromatic amines in a continuous flow reactor[J].Tetrahedron Letters,2009,50:7263-7267.
[15]MALET-SANZ L,MADRZAK J,LEY S Y,et al.Preparation of arylsulfonyl chlorides by chlorosulfonylation of in situ generated diazonium salts using a continuous flow reactor[J].Org.Biomol.Chem.,2010,8:5324-5332.
[16]YU Z Q,LV Y W,YU C M,et al.Continuous flow reactor for BalzSchiemann reaction:a new procedure for the preparation of aromatic fluorides[J].Tetrahedron Letters,2013,54:1261-1263.
[17]YU Z Q,LV Y W,YU C M.A continuous kilogram-scale process for the manufacture of o-difluorobenzene[J].Org.Process Res.Dev.,2012,16:1669-1672.
[18]AHMED-OMER B,BARROW D A,WIRTH T.Heck reactions using segmented flow conditions[J].Tetrahedron Letters,2009,50:3352-3355.
[19]AHMED B,BARROW D,WIRTH T.Enhancement of reaction rates by segmented fluid flow in capillary scale reactors[J].Adv.Synth.Catal.,2006,348:1043-1048.
[20]CHERNYAK N,BUCHWALD S L.Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts[J].J.Am.Chem.Soc.,2012,134:12466-12469.
[21]YU Z Q,YE X,XU Q,et al.A fully continuous-flow process for the synthesis of p-cresol:impurity analysis and process optimization[J].Org.Process Res.Dev.,2017,21:1644-1652.
[22]杨玉宇.重氮化管式反应器试验研究[D].杭州:浙江工业大学,2008.YANG Y Y.Experimental study on diazotization in a tubular reactor[D].Hangzhou:Zhejiang University of Technology,2008.
[23]CHENICEK J A,GLEIM W K T.Preparation of palkylaminoazobenzenes:US2714104[P].1955-7-26.
[24]MAHAJAN A J,KIRWAN D J.Micromixing effects in a twoimpinging-jets precipitator[J].AIChE Journal,1996,42(7):1801-1814.
[25]BEHRINGER H,KARRENBAUER K,REHBERG H.Continuous production of azo pigments:US4454067[P].1984-6-12.
[26]何旭斌,欧其,王新武,等.非重氮-偶联法合成偶氮染料[J].上海染料,2012,40(5):36-40.HE X B,OU Q,WANG X W,et al.Azo dyes are synthesized by nondiazo-coupling method[J].Shanghai Dyestuff,2012,40(5):36-40.
[27]杨林涛,刘东,王永华.微通道反应器在重氮化偶合反应中的应用研究[J].染料与染色,2017,54(2):57-61.YANG L T,LIU D,WANG Y H.Application of microchannel reactors in dizaotization and coupling[J].Dyestuffs and Coloration,2017,54(2):57-61.
[28]WANG F J,HUANG J P,XU J X.Continuous-flow synthesis of azo dyes in a microreactor system[J].Chemical Engineering&Processing:Process Intensification,2018,127:43-49.
[29]HISAMOTO H,SAITO T,KITAMORI T,et al.Fast and high conversion phase-transfer synthesis exploiting the liquid-liquid interface formed in a microchannel chip[J].Chem.Commun.,2001,2662-2663.
[30]DIETZ E,WEBER J,SCHNAITMANN D,et al.Process for fine division of organic pigments by precipitation:US6537364[P].2003-3-25.
[31]PENNEMANN H,FORSTER S,KINKEL J,et al.Improvement of dye properties of the azo pigment Yellow 12 using a micromixer-based process[J].Organic Process Research&Development,2005,9(2):188-192.
[32]王永华,于兴春,杨林涛.加强工程化研究打造高品质颜料[J].上海染料,2014,42(2):50-53.WANG Y H,YU X C,YANG L T.Strengthen the engineering study to making high quality azo pigment[J].Shanghai Dyestuff,2014,42(2):50-53.
[33]赵卫国,苏金奇,鞠苏华.一种利用微反应器制备活性染料活性深红C-D方法:101284950[P].2008-10-15.ZHAO W G,SU J Q,JU S H.A method for the preparation of Active Red C-D dyes by using a microreactor:101284950[P].2008-10-15.
[34]张淑芬,梁栋,吕荣文,等.水溶性偶氮染料的螺旋管混沌混合的连续化制备方法:102618063A[P].2012-08-01.ZHANG S F,LIANG D,LYU R W,et al.A continuous preparation method for the chaotic mixing of water-soluble azo dyes:102618063A[P].2012-08-01.
[35]梁栋.缩放螺旋混合器用于偶氮染料连续化制备的研究[D].大连:大连理工大学,2014.LIANG D.Contraction-expansion helical mixer and its application in continuous preparation of azo dyes[D].Dalian:Dalian University of Technology,2014.
[36]余武斌,郑明明,叶青.微通道反应器内偶氮活性染料连续偶合工艺研究[J].染料与染色,2015,52(1):1-4.YU W B,ZHENG M M,YE Q.Study on the continuous coupling reaction for synthesis of azo reactive dyes in microreactor[J].Dyestuffs and Coloration,2015,52(1):1-4.
[37]AKWI F M,WATTS P.The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors[J].Beilstein J.Org.Chem.,2016,12:1987-2004.
[38]AKWI F M,BOSMA C,WATTS P.A facile optimization of diazotization and phase transfer catalyzed azo-coupling reactions in microreactors[J].J.Flow Chem.,2016,6(2):73-79.
[39]NICKEL U,JUNG R,SAITMACHER K,et al.Preparation of azo colorants in microreactors:US6469147[P].2002-10-22.
[40]NICKEL U,KUND K,ALFTER F.Preparation of disazo condensation pigments in microreactors:US6437104[P].2002-8-20.
[41]NICKEL U,UNVERDORBEN L,WEBER J,et al.Preparation of diketopyrrolopyrrole pigments:US6723138[P].2004-4-20.
[42]徐建鸿,王法军,黄晋培,等.一种微反应器内连续化制备偶氮染料的方法:107488361[P].2017-12-19.XU J H,WANG F J,HUANG J P,et al.A method for the continuous preparation of azo dyes in a microreactor:107488361[P].2017-12-19.
[43]杜长森,梁栋,卢圣国,等.偶氮颜料在分支螺旋管中的连续化制备方法:104479394[P].2015-04-01.DU C S,LIANG D,LU S G,et al.The continuous preparation method of azo pigment in the branch spiral tube:104479394[P].2015-04-01.
[2]郑亚峰,赵阳,辛峰.微反应器研究与展望[J].化工进展,2004,23(5):461-466.ZHENG Y F,ZHAO Y,XIN F.Research and prospects of microreactors[J].Chemical Industry and Engineering Progress,2004,23(5):461-466.
[3]刘兆利,张鹏飞.微反应器在化学化工领域中的应用[J].化工进展,2016,35(1):10-17.LIU Z L,ZHANG P F.Applications of microreactor in chemistry and chemical engineering[J].Chemical Industry and Engineering Progress,2016,35(1):10-17.
[4]BOU-DIAB L,FIERZ H,GWERDER C,et al.A new multipurpose microreactor for process safety studies[J].Organic Process Research&Development,2003,7:1077-1078.
[5]MO F Y,DONG G B,ZHANG Y,et al.Recent applications of arene diazonium salts in organic synthesis[J].Org.Biomol.Chem.,2013,11:1582-1593.
[6]DEADMAN B J,COLLINS S G,MAGUIRE A R.Taming hazardous chemistry in flow:the continuous processing of diazo and diazonium compounds[J].Chem.Eur.J.,2015,21:2298-2308.
[7]MULLER S T R,WIRTH T.Diazo compounds in continuous-flow technology[J].ChemSusChem.,2015,8:245-250.
[8]SHUKLA C A,KULKARNI A A,RANADE V V.Selectivity engineering of the diazotization reaction in a continuous flow reactor[J].React.Chem.Eng.,2016,1:387-389.
[9]PARTINGTON S,WALDRAM S P.Runaway reaction during production of an azo dye intermediate[J].Trans IChemE.,2002,80:33-39.
[10]WOOTTON R C,FORTT R,DE MELLO A J,et al.On-chip generation and reaction of unstable intermediates-monolithic nanoreactors for diazonium chemistry:azo dyes[J].Lab Chip,2002,2:5-7.
[11]WOOTTON R C,FORTT R,DE MELLO A J.Continuous-flow generation of anhydrous diazonium species:monolithic microfluidic reactors for the chemistry of unstable intermediates[J].Organic Process Research&Development,2003,7:762-768.
[12]ATTOMA J D,CAMARA T,ROUTIER S,et al.Efficient transposition of the Sandmeyer reaction from batch to continuous process[J].Org.Process Res.Dev.,2017,21:44-51.
[13]KARNEY M J,PORTER K A,VANIER G S,et al.Meso-scale microwave-assisted continuous flow reactions utilizing a selective heating matrix[J].RSC Advances,2013,3:7106-7111.
[14]MALET-SANZ L,MADRZAK J,HOLVEY R S,et al.A safe and reliable procedure for the iododeamination of aromatic and heteroaromatic amines in a continuous flow reactor[J].Tetrahedron Letters,2009,50:7263-7267.
[15]MALET-SANZ L,MADRZAK J,LEY S Y,et al.Preparation of arylsulfonyl chlorides by chlorosulfonylation of in situ generated diazonium salts using a continuous flow reactor[J].Org.Biomol.Chem.,2010,8:5324-5332.
[16]YU Z Q,LV Y W,YU C M,et al.Continuous flow reactor for BalzSchiemann reaction:a new procedure for the preparation of aromatic fluorides[J].Tetrahedron Letters,2013,54:1261-1263.
[17]YU Z Q,LV Y W,YU C M.A continuous kilogram-scale process for the manufacture of o-difluorobenzene[J].Org.Process Res.Dev.,2012,16:1669-1672.
[18]AHMED-OMER B,BARROW D A,WIRTH T.Heck reactions using segmented flow conditions[J].Tetrahedron Letters,2009,50:3352-3355.
[19]AHMED B,BARROW D,WIRTH T.Enhancement of reaction rates by segmented fluid flow in capillary scale reactors[J].Adv.Synth.Catal.,2006,348:1043-1048.
[20]CHERNYAK N,BUCHWALD S L.Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts[J].J.Am.Chem.Soc.,2012,134:12466-12469.
[21]YU Z Q,YE X,XU Q,et al.A fully continuous-flow process for the synthesis of p-cresol:impurity analysis and process optimization[J].Org.Process Res.Dev.,2017,21:1644-1652.
[22]杨玉宇.重氮化管式反应器试验研究[D].杭州:浙江工业大学,2008.YANG Y Y.Experimental study on diazotization in a tubular reactor[D].Hangzhou:Zhejiang University of Technology,2008.
[23]CHENICEK J A,GLEIM W K T.Preparation of palkylaminoazobenzenes:US2714104[P].1955-7-26.
[24]MAHAJAN A J,KIRWAN D J.Micromixing effects in a twoimpinging-jets precipitator[J].AIChE Journal,1996,42(7):1801-1814.
[25]BEHRINGER H,KARRENBAUER K,REHBERG H.Continuous production of azo pigments:US4454067[P].1984-6-12.
[26]何旭斌,欧其,王新武,等.非重氮-偶联法合成偶氮染料[J].上海染料,2012,40(5):36-40.HE X B,OU Q,WANG X W,et al.Azo dyes are synthesized by nondiazo-coupling method[J].Shanghai Dyestuff,2012,40(5):36-40.
[27]杨林涛,刘东,王永华.微通道反应器在重氮化偶合反应中的应用研究[J].染料与染色,2017,54(2):57-61.YANG L T,LIU D,WANG Y H.Application of microchannel reactors in dizaotization and coupling[J].Dyestuffs and Coloration,2017,54(2):57-61.
[28]WANG F J,HUANG J P,XU J X.Continuous-flow synthesis of azo dyes in a microreactor system[J].Chemical Engineering&Processing:Process Intensification,2018,127:43-49.
[29]HISAMOTO H,SAITO T,KITAMORI T,et al.Fast and high conversion phase-transfer synthesis exploiting the liquid-liquid interface formed in a microchannel chip[J].Chem.Commun.,2001,2662-2663.
[30]DIETZ E,WEBER J,SCHNAITMANN D,et al.Process for fine division of organic pigments by precipitation:US6537364[P].2003-3-25.
[31]PENNEMANN H,FORSTER S,KINKEL J,et al.Improvement of dye properties of the azo pigment Yellow 12 using a micromixer-based process[J].Organic Process Research&Development,2005,9(2):188-192.
[32]王永华,于兴春,杨林涛.加强工程化研究打造高品质颜料[J].上海染料,2014,42(2):50-53.WANG Y H,YU X C,YANG L T.Strengthen the engineering study to making high quality azo pigment[J].Shanghai Dyestuff,2014,42(2):50-53.
[33]赵卫国,苏金奇,鞠苏华.一种利用微反应器制备活性染料活性深红C-D方法:101284950[P].2008-10-15.ZHAO W G,SU J Q,JU S H.A method for the preparation of Active Red C-D dyes by using a microreactor:101284950[P].2008-10-15.
[34]张淑芬,梁栋,吕荣文,等.水溶性偶氮染料的螺旋管混沌混合的连续化制备方法:102618063A[P].2012-08-01.ZHANG S F,LIANG D,LYU R W,et al.A continuous preparation method for the chaotic mixing of water-soluble azo dyes:102618063A[P].2012-08-01.
[35]梁栋.缩放螺旋混合器用于偶氮染料连续化制备的研究[D].大连:大连理工大学,2014.LIANG D.Contraction-expansion helical mixer and its application in continuous preparation of azo dyes[D].Dalian:Dalian University of Technology,2014.
[36]余武斌,郑明明,叶青.微通道反应器内偶氮活性染料连续偶合工艺研究[J].染料与染色,2015,52(1):1-4.YU W B,ZHENG M M,YE Q.Study on the continuous coupling reaction for synthesis of azo reactive dyes in microreactor[J].Dyestuffs and Coloration,2015,52(1):1-4.
[37]AKWI F M,WATTS P.The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors[J].Beilstein J.Org.Chem.,2016,12:1987-2004.
[38]AKWI F M,BOSMA C,WATTS P.A facile optimization of diazotization and phase transfer catalyzed azo-coupling reactions in microreactors[J].J.Flow Chem.,2016,6(2):73-79.
[39]NICKEL U,JUNG R,SAITMACHER K,et al.Preparation of azo colorants in microreactors:US6469147[P].2002-10-22.
[40]NICKEL U,KUND K,ALFTER F.Preparation of disazo condensation pigments in microreactors:US6437104[P].2002-8-20.
[41]NICKEL U,UNVERDORBEN L,WEBER J,et al.Preparation of diketopyrrolopyrrole pigments:US6723138[P].2004-4-20.
[42]徐建鸿,王法军,黄晋培,等.一种微反应器内连续化制备偶氮染料的方法:107488361[P].2017-12-19.XU J H,WANG F J,HUANG J P,et al.A method for the continuous preparation of azo dyes in a microreactor:107488361[P].2017-12-19.
[43]杜长森,梁栋,卢圣国,等.偶氮颜料在分支螺旋管中的连续化制备方法:104479394[P].2015-04-01.DU C S,LIANG D,LU S G,et al.The continuous preparation method of azo pigment in the branch spiral tube:104479394[P].2015-04-01.