环保绝缘气体七氟异丁腈(C_4F_7N)的制备技术现状与发展
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摘要
七氟异丁腈(C_4F_7N)具有优异的绝缘性能和较低的温室效应,是一种备受关注的SF_6替代气体。然而,七氟异丁腈尚未工业化生产,其制备技术是制约其大规模应用的关键问题。为了突破国际壁垒、加快七氟异丁腈批量国产化的进程,综述了国内外七氟异丁腈的制备技术,详细介绍了传统和新型制备技术的研究概况,阐述各种制备技术的反应流程,从原料毒性、反应条件、反应设备和产物收率等方面揭示了各种制备方法之间的差异与优缺点,提出了具有工业化生产潜力的制备七氟异丁腈的新方法,并就七氟异丁腈制备技术的发展做出展望。
Heptafluoroisobutyronitrile is considered to be an attractive alternative gas of SF_6 because of its excellent insulating properties and low GWP. However, heptafluoroisobutyronitrile has not been industrially produced, and the preparation technology is the crucial problem that restricts its large-scale application. In order to break through the international barriers and accelerate the process of localization, the preparation technology of heptafluoroisobutyronitrile at home and abroad is reviewed and the research of traditional and new progress is introduced in detail with the reaction process of various method described. From the angle of the comparison of raw material toxicity, reaction conditions, reaction equipment and product yield, the preparation methods with industrial production potential are proposed, and the development of preparation technology of heptalfluoroisobutyronitrile is prospected.
Heptafluoroisobutyronitrile is considered to be an attractive alternative gas of SF_6 because of its excellent insulating properties and low GWP. However, heptafluoroisobutyronitrile has not been industrially produced, and the preparation technology is the crucial problem that restricts its large-scale application. In order to break through the international barriers and accelerate the process of localization, the preparation technology of heptafluoroisobutyronitrile at home and abroad is reviewed and the research of traditional and new progress is introduced in detail with the reaction process of various method described. From the angle of the comparison of raw material toxicity, reaction conditions, reaction equipment and product yield, the preparation methods with industrial production potential are proposed, and the development of preparation technology of heptalfluoroisobutyronitrile is prospected.
引文
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[24]MICHAEL G C,RICHARD M F,MICHAEL J B.Fluorinated nitriles as dielectric gases:USA,0083979[P].2015-03-26.
[25]宋新巍,黄晓磊,任章顺,等.一种合成全氟异丁腈的方法:中国,108395382A[P].2018-08-14.SONG Xinwei,HUANG Xiaolei,REN Zhangshun,et al.A process for synthesis of perfluoroisobutyronitrile:China,108395382A[P].2018-08-14.
[26]权恒道,张呈平,庆飞要,等.全氟腈的制备方法:中国,108424375A[P].2018-08-21.QUAN Hengdao,ZHANG Chengping,QING Feiyao,et al.Processes for preparation of perfluoroisobutyronitrile:China,108424375A[P].2018-08-21.
[27]WANG Y,SUN M T,GAO Z Y,et al.A novel and efficient synthetic route to perfluoroisobutyronitrile from perfluoroiobutyryl acid[J].RSCAdvances,2018,8:37159-37164.
[28]王易,邹利林,于萍,等.一种由七氟-2-卤代烷烃制备七氟异丁酰氯的方法:中国,108276272A[P].2018-07-13.WANG Yi,ZHOU Lilin,YU Ping,et al.A method for preparing heptafluoroisobutylchloride from heptafluoro-2-haloal-kane:China,108276272A[P].2018-07-13.
[29]王敏,高占阳,罗运柏,等.一种由草酰氯氟化制备双-(七氟异丙基)-酮方法:中国,108191628A[P].2018-06-22.WANG Min,GAO Zhanyang,LUO Yunbai,et al.A process for preparing bis-(heptafluoroisobutyl)-ketone from oxalyl chloride:China,108191628A[P].2018-06-22.
[30]高占阳,王敏,罗运柏,等.一种由双-(七氟异丙基)-酮和氨制备七氟异丁基酰胺的方法:中国,108440327A[P].2018-08-24.GAO Zhanyang,WANG Min,LUO Yunbai,et al.A process for preparing heptafluoroisobutylamide from bis-(heptafluoroisobutyl-ketone with ammonia:China,108440327A[P].2018-08-24.
[2]周文俊,郑宇,高克利,等.环保型绝缘气体电气特性研究进展[J].高电压技术,2018,44(10):3114-3124.ZHOU Wenjun,ZHENG Yu,GAO Keli,et al.Progress in researching electrical characteristics of environment-friendly insulating gases[J].High Voltage Engineering,2018,44(10):3114-3124.
[3]张英,陈琪,张晓星,等.C3F7CN/CO2混合气体在准均匀电场中的绝缘性能[J].高电压技术,2018,44(10):3158-3164.ZHANG Ying,CHEN Qi,ZHANG Xiaoxing,et al.Insulation performance of C3F7CN/CO2 gas mixture in quasi-uniform electric field[J].High Voltage Engineering,2018,44(10):3158-3164.
[4]周文俊,郑宇,杨帅,等.替代SF6的环保型绝缘气体研究进展与趋势[J].高压电器,2016,52(12):8-14.ZHOU Wenjun,ZHENG Yu,YANG Shuai,et al.Research progress and trend of SF6 alternative with environment friendly insulation gas[J].High Voltage Apparatus,2016,52(12):8-14.
[5]谭东现,周柏杰,蔡凡一,等.高气压CF3I-N2混合气体雷电冲击耐受特性及其在GIL中的应用[J].高电压技术,2018,44(10):3150-3157.TAN Dongxian,ZHOU Baijie,CAI Fanyi,et al.Lighting impulse withstand performances of high-pressure CF3I-N2 gas mixture and its application in GIL[J].High Voltage Engineering,2018,44(10):3150-3157.
[6]YAMAMOTO O,TAKUMA T,HAMADA S.Applying a gas mixture containing c-C4F8 as an insulation medium[J].IEEE Transactions on Dielectrics and Electrical Insulation,2001,8(6):1075-1081.
[7]李康,张国强,邢卫军,等.c-C4F8及其与N2混合绝缘气体在典型故障的分解生成物的试验分析[J].高电压技术,2012,38(4):985-992.LI Kang,ZHANG Guoqiang,XING Weijun,et al.Experiment analysis of decomposition products in typical fault of c-C4F8 gas and insulating gas mixture containing c-C4F8 and N2[J].High Voltage Engineering,2012,38(4):985-992.
[8]HYRENBACH M,HINTZEN T,MüLLER P,et al.Alternative gas insulation in medium-voltage switchgear[C]∥23rd International Conference on Electricity Distribution.Lyon,France:CIRED,2015:1-5.
[9]颜湘莲,高克利,郑宇,等.SF6混合气体及替代气体研究进展[J].电网技术,2018,42(6):1837-1844.YAN Xianglian,GAO Keli,ZHENG Yu,et al.Progress of gas mixture and alternative gas of SF6[J].Power System Technology,2018,42(6):1837-1844.
[10]KIEFFEL Y,IRWIN T,PONCHON P,et al.Green gas to replace SF6in electrical grids[J].IEEE Power&Energy Magazine,2016,14(2):32-39.
[11]NECHMI H E,BEROUAL A,GIRODET A,et al.Fluoronitriles/CO2gas mixture as promising substitute to SF6 for insulation in high voltage applications[J].IEEE Transactions on Dielectrics&Electrical Insulation,2016,23(5):2587-2593.
[12]KIEFFEL Y,BIQUEZ F,PONCHON P,et al.SF6 alternative development for high voltage switchgears[C]∥Electrical Insulation Conference.Denver,USA:IEEE,2015:379-383.
[13]高克利,颜湘莲,王浩,等.环保型气体绝缘输电线路(GIL)技术发展[J].高电压技术,2018,44(10):3105-3113.GAO Keli,YAN Xianglian,WANG Hao,et al.Progress in environment-friendly gas-insulated transmission line(GIL)[J].High Voltage Engineering,2018,44(10):3105-3113.
[14]YU X J,HOU H,WANG B S.Double-layered composite methods extrapolating to complete basis-set limit for the systems involving more than ten heavy atoms:application to the reaction of heptafluoroisobutyronitrile with hydroxyl radical[J].The Journal of Physical Chemistry A,2017,121(47):9020-9032.
[15]CHAMBERS R D,TAMURA M,HOWARD J K,et al.Perfluoroalkyl-1,2,3-triazines:novel nucleophilic attack on ring nitrogen[J].Chem Inform,1988,19(16):1697-1698.
[16]CHAMBERS R D,SHEPHERD T,TAMURA M,et al.Photochemistry of halogenocarbon compounds,part 6:direct observation of fluorinated azetes[J].Chem Inform,1990,21(29):983-987.
[17]CHAMBERS R D,SHEPHERD T,TAMURA M.Photochemistry of halogenocarbon compounds,part 5:photolysis of fluorinated 1,2,3-triazine derivatives[J].Chem Inform,1990,21(29):975-981.
[18]CHAMBERS R D,SHEPHERD T,TAMURA M,et al.Novel synthesis and regiospecific cycloaddition reactions of pefluoro-3-methylbut-1-yne[J].Chem Inform,1990,21(16):1657-1658.
[19]CHAMBERS R D,SHEPHERD T,TAMURA M.Polyhalogenoheterocyclic compounds,part 38:synthesis of trifluoro-1,2,3-triazine and perfluoroisopropyl derivatives[J].Chem Inform,1988,19(36):2583-2590.
[20]CHAMBERS R D,TAMURA M,SHEPHERD T,et al.Azetes from fluorinated 1,2,3-triazines[J].Journal of the Chemical Society Chemical Communications,1987,22(22):1699-1700.
[21]BARLOW M G,HASZELDINE R N,SIMON C.Heterocyclic polyfluoro-compounds,part 30:perfluoroalkylation of trifluoro-1,2,4-triazine[J].Journal of the Chemical Society,Perkin Transactions,1980:2254-2257.
[22]BARNES R N,CHAMBERS R D,HERCLIFFE R D,et al.Photochemistry of halogenocarbon compounds,part 4:photochemical conversions of some fluorinated aza-and diaza-cyclohexadienes[J].Journal of the Chemical Society,Perkin Transactions,1981:3289-3291.
[23]BRYCE C O,FLORHAM P,CYRIL W,et al.Process for preparing fluoroperhaloalkyl nitriles:USA,3752840[P].1997-11-04.
[24]MICHAEL G C,RICHARD M F,MICHAEL J B.Fluorinated nitriles as dielectric gases:USA,0083979[P].2015-03-26.
[25]宋新巍,黄晓磊,任章顺,等.一种合成全氟异丁腈的方法:中国,108395382A[P].2018-08-14.SONG Xinwei,HUANG Xiaolei,REN Zhangshun,et al.A process for synthesis of perfluoroisobutyronitrile:China,108395382A[P].2018-08-14.
[26]权恒道,张呈平,庆飞要,等.全氟腈的制备方法:中国,108424375A[P].2018-08-21.QUAN Hengdao,ZHANG Chengping,QING Feiyao,et al.Processes for preparation of perfluoroisobutyronitrile:China,108424375A[P].2018-08-21.
[27]WANG Y,SUN M T,GAO Z Y,et al.A novel and efficient synthetic route to perfluoroisobutyronitrile from perfluoroiobutyryl acid[J].RSCAdvances,2018,8:37159-37164.
[28]王易,邹利林,于萍,等.一种由七氟-2-卤代烷烃制备七氟异丁酰氯的方法:中国,108276272A[P].2018-07-13.WANG Yi,ZHOU Lilin,YU Ping,et al.A method for preparing heptafluoroisobutylchloride from heptafluoro-2-haloal-kane:China,108276272A[P].2018-07-13.
[29]王敏,高占阳,罗运柏,等.一种由草酰氯氟化制备双-(七氟异丙基)-酮方法:中国,108191628A[P].2018-06-22.WANG Min,GAO Zhanyang,LUO Yunbai,et al.A process for preparing bis-(heptafluoroisobutyl)-ketone from oxalyl chloride:China,108191628A[P].2018-06-22.
[30]高占阳,王敏,罗运柏,等.一种由双-(七氟异丙基)-酮和氨制备七氟异丁基酰胺的方法:中国,108440327A[P].2018-08-24.GAO Zhanyang,WANG Min,LUO Yunbai,et al.A process for preparing heptafluoroisobutylamide from bis-(heptafluoroisobutyl-ketone with ammonia:China,108440327A[P].2018-08-24.