2-碘七氟丙烷的合成方法
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摘要
介绍了2-碘七氟丙烷的特性及应用,叙述了其制造方法,包括六氟丙烯法、四氟乙烯法及七氟异丁酸钾法、双(七氟异丙基)汞法、2-碘-全氟-2-丁烯法等,分析各种方法的优缺点。认为有工业化潜力的方法是六氟丙烯法,主要原料可选择六氟丙烯、I2、KF与N,N-二甲基甲酰胺,在高压釜自发压力下反应,反应温度60~70℃、时间3~4 h,收率可达87%;也可选择六氟丙烯、I2、氯气/磺酰氯、氢氟酸与BF3,在高压釜自发压力下反应,反应温度170℃、时间5 h,收率可达94%。
The paper introduced the characteristic and application of 2-iodoheptafluoropropane and described its preparation methods including hexafluoropropylene method, tetrafluoroethylene method and potassium heptafluoroisobutyrate method, di(heptafluoroisopropyl)mercury method, 2-iodo-perfluorinated-2-butene method etc, analyzed their advantages and disadvantages, pointed out the industrial potential method is hexafluoropropylene method. The main raw material could choose hexafluoropropylene, I2, KF and N,N-dimethyl formamide, they reacted in autoclave under spontaneous pressure, reaction temperature was 60~70 ℃, reaction time was 3 ~ 4 h, and the reaction yield can reach 87%; the main raw material could also choose hexafluoropropylene, I2, chlorine gas/sulfonyl chloride,hydrofluoric acid and BF3, they reacted in autoclave under spontaneous pressure, reaction temperature was170 ℃, reaction time was5 h, and the reaction yield can reach 94%.
The paper introduced the characteristic and application of 2-iodoheptafluoropropane and described its preparation methods including hexafluoropropylene method, tetrafluoroethylene method and potassium heptafluoroisobutyrate method, di(heptafluoroisopropyl)mercury method, 2-iodo-perfluorinated-2-butene method etc, analyzed their advantages and disadvantages, pointed out the industrial potential method is hexafluoropropylene method. The main raw material could choose hexafluoropropylene, I2, KF and N,N-dimethyl formamide, they reacted in autoclave under spontaneous pressure, reaction temperature was 60~70 ℃, reaction time was 3 ~ 4 h, and the reaction yield can reach 87%; the main raw material could also choose hexafluoropropylene, I2, chlorine gas/sulfonyl chloride,hydrofluoric acid and BF3, they reacted in autoclave under spontaneous pressure, reaction temperature was170 ℃, reaction time was5 h, and the reaction yield can reach 94%.
引文
[1]七氟-2-碘代丙烷[EB/OL].[2015-04-28].http://www.chemicalbook.com/Search.aspx?keyword=677-69-0.
[2]七氟-2-碘代丙烷[EB/OL].[2015-04-28].http://www.molbase.com/zh/search.html?search_keyword=677-69-0.
[3]徐宇威,徐卫国.七氟异丙基碘在含氟有机化学品合成中的应用[J].有机氟工业,2005(4):16-18.
[4]张永明,王军,高洪光,等.一种氧化还原引发制备全氟烷基碘的调聚方法:中国,1927791[P].2007-03-14.
[5]冯东东,粟小理,江建安,等.中等链长多氟烷基乙基碘化物的合成方法:中国,101434511[P].2009-05-20.
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[27]George K C,Alexandrovich P V.Addition of Trifluoromethanes to Fluoroolefins and Isomerization of Monohaloperfluoroalkanes:WO,9702227[P].1997-01-23.
[28]Petrov V A,Krespan C G.Addition of some Unreactive Fluoroalkanes to Tetrafluoroethylene.Direct Catalytic Synthesis of F-butene-2[J].J of Fluo Chem,2000,102(1/2):199-204.
[29]向绍基,李华,孔小林,等.一种低碳数全氟烷基碘的制备方法:中国,102464569[P].2012-05-23.
[30]Kitching W,Glenn M.Organometallic Complexes of Mercury[J].Sci of Syn,2004,3:133-303.
[31]Sun K K,Miller W T.Perfluorophenylsilver[J].J of Am Chem Soc,1970,92:6985-6987.
[2]七氟-2-碘代丙烷[EB/OL].[2015-04-28].http://www.molbase.com/zh/search.html?search_keyword=677-69-0.
[3]徐宇威,徐卫国.七氟异丙基碘在含氟有机化学品合成中的应用[J].有机氟工业,2005(4):16-18.
[4]张永明,王军,高洪光,等.一种氧化还原引发制备全氟烷基碘的调聚方法:中国,1927791[P].2007-03-14.
[5]冯东东,粟小理,江建安,等.中等链长多氟烷基乙基碘化物的合成方法:中国,101434511[P].2009-05-20.
[6]Wlassics I,Tortelli V.Couplin g Reactions of Chlorofluoro and Perfluoroalkyl Iodides[J].Collect of Czech Chem Commun,2008,73(12):1719-1728.
[7]Hedrick V.Fire Extinguishing and Fire Suppression Compositions Comprising Unsaturated Fluorocarbons:WO,2007059468[P].2007-05-24.
[8]Onishi M.Preparation of perfluoroalkylanilines as Intermediates in the Synthesis of Agricultural and Horticultural Insecticides:EP,1380568[P].2004-01-14.
[9]Onishi M.A Process for Producing Perfluoroalkylaniline Derivatives:EP,1006102[P].2000-06-07.
[10]唐秀红,孙华君,曹松.含七氟异丙基的苯胺类化合物的合成[J].化工生产与技术,2008,15(6):5-7.
[11]沈佳萍,罗亦婷,李舒婷,等.2-乙基-4-七氟异丙基苯胺的合成[J].广州化工,2011,39(17):65-66.
[12]李正名,闫涛,刘团伟,等.双酰胺衍生物及其制备和应用:中国,102503876[P].2012-06-20.
[13]李正名,赵毓,冯启,等.一类吡唑酰胺衍生物及其应用:中国,101659655[P].2010-03-03.
[14]大西正展,好浦昭彦,河野荣司,等.苯胺衍生物和其生产方法:中国,1257861[P].2000-06-28.
[15]Matsuzaki Y.Preparation of Phthalamide Derivatives,Pesticides for Agricultural and Horticultural Applications which Comprises Said Derivatives,and Method of Utilizing Said Pesticides:WO,2013065725[P].2013-05-13.
[16]吕龙,齐卿卿.5-多氟烷基取代的2-氨基噻唑类化合物、合成方法及其应用:中国,101885708[P].2010-11-17.
[17]Qi Qingqing,Shen Qilong,Lv Long.Polyfluoroalkylation of2-aminothiazoles[J].J of Fluo Chem,2012,133:115-119.
[18]Qi Qingqing.Polyfluoroalkylation of 2-aminothiazoles:Unexpected sp3 C-Cl Substitution under Mild Conditions[J].Chine J of Chem,2011,29(12):2681-2683.
[19]Chambers R D,Musgrave W K R,Savory J.Mixtures of Halogens and Halogen Polyfluorides as Effective Sources of the Halogen Monofluorides in Reactions with Fluoroolefins[J].J of Chem Soc,1961:3779-3786.
[20]Krespan C G.Synthesis of Fluoroalkyl Iodides[J].J of Org Chem,1962,27:1813-1814.
[21]Dmowski,Wojciech.Preparation of Heptafluorisopropyl Iodide:PL,157347[P].1992-05-29.
[22]Petrov V A,Krespan C G.Conjugated Electrophilic Iodofluorination of Fluoroolefins[J].J of Org Chem,1996,61(26):9605-9607.
[23]Petrov V A,Krespan C G.Process for the Preparation of Perfluoroalkyl Iodides:WO,9504020[P].1995-02-09.
[24]郭彩云,张元发,陈庆云.全氟和多氟烷基磺酸的研究Ⅵ.一些长链烷基磺酰氟的合成[J].化学学报,1982,40(9):828-834.
[25]Millauer H.Process for the Preparation of Pentafluorethyl Iodide and Heptafluorisopropyl Iodide:US,3829512[P].1974-08-13.
[26]吴梓新,高慧敏,许家福,等.单碘代全氟烷的制备方法:中国,101456789[P].2009-06-17.
[27]George K C,Alexandrovich P V.Addition of Trifluoromethanes to Fluoroolefins and Isomerization of Monohaloperfluoroalkanes:WO,9702227[P].1997-01-23.
[28]Petrov V A,Krespan C G.Addition of some Unreactive Fluoroalkanes to Tetrafluoroethylene.Direct Catalytic Synthesis of F-butene-2[J].J of Fluo Chem,2000,102(1/2):199-204.
[29]向绍基,李华,孔小林,等.一种低碳数全氟烷基碘的制备方法:中国,102464569[P].2012-05-23.
[30]Kitching W,Glenn M.Organometallic Complexes of Mercury[J].Sci of Syn,2004,3:133-303.
[31]Sun K K,Miller W T.Perfluorophenylsilver[J].J of Am Chem Soc,1970,92:6985-6987.