English
新闻公告
More
化学进展 2010, Vol. 22 Issue (12): 2316-2327 前一篇   后一篇

• 综述与评论 •

基于离子液体电解液的有机电化学反应

褚道葆, 周莹, 张雪娇, 李艳, 宋奇   

  1. 安徽省功能性分子固体、分子基材料重点实验室,安徽师范大学化学与材料科学学院 芜湖 241000
  • 出版日期:2010-12-24 发布日期:2010-11-04
  • 作者简介:e-mail:dbchu@sina.com
  • 基金资助:

    国家自然科学基金(No. 20476001)、安徽省自然科学基金(No. 070414160)及高校自然科学重点基金(KJ2007A010)资助

Organic Electrochemical Reactions Based on Ionic Liquid Electrolytes

Chu Daobao, Zhou Ying, Zhang Xuejiao, Li Yan, Song Qi   

  1. Anhui Key Laboratory of Functional Molecular Solids and Molecular Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
  • Online:2010-12-24 Published:2010-11-04

室温离子液体(RTILs) 作为一类在室温时呈液态且具有良好导电性的新型绿色溶剂, 在有机电化学反应体系中的应用前景广阔。本文介绍了近年报道过的新型离子液体及离子液体电解液的特性,阐述了基于离子液体电解液的电化学实验方法,重点综述了离子液体中的各种有机电化学反应,包括电化学还原反应、CO2在离子液体中的电化学固定、电化学氧化反应、烯烃的环氧化、选择性氟化反应、偶联反应、功能化有机硅氧烷的合成、电化学氟化脱硫反应、电化学聚合反应等,并展望了发展趋势。

Room-temperature ionic liquids (RTILs),as a class of novel  "green solvents" that exist in the liquid state around room-temperature and possess excellent ionic conductivity, have many promising applications in organic electrochemical reaction. In the review, new type of ionic liquids reported in recent years and the properties of ionic liquid electrolyte are described. The electrochemical experimental methods based on ionic liquid electrolyte are also discussed. Various organic electrochemical reactions in ionic liquid,including electrochemical reduction, electroreduction fixation of CO2, electrochemical oxidation, olefin epoxidation, selective fluorination reaction, coupling reaction,the synthesis of functional organic siloxane, electrochemical fluorination desulfurization,electrochemical polymerization reaction, etc, are reviewed specifically, and the development trend is given.

Contents
1 Introduction
2 The new ionic liquids
3 Properties of ionic liquid electrolytes
3.1 Viscosity
3.2 Conductivity
3.3 Diffusion of electroactive solutes
3.4 Effects of impurities
3.5 Electrochemical windows
4 The experimental methods based on ionic liquid electrolytes
5 Organic electrochemical reactions in ionic liquids
5.1 Electrochemical reduction
5.2 Fixation of CO2 in ionic liquids
5.3 Electrochemical oxidation
5.4 Olefin epoxidation
5.5 Selective fluorination reaction
5.6 Coupling reaction
5.7 The synthesis of functional organic siloxane
5.8 Electrochemical fluorination desulfurization
5.9 Electrochemical polymerization reaction
6 Conclusion and perspective

中图分类号: 

()


[1] Yoshida J I, Kataoka K, Horcajada R, Nagaki A. Chem. Rev.,2008,108: 2265—2299

[2] Chu D B, Xu M, Lu J, Zheng P, Qin G X, Yuan X M. Electrochem. Commun., 2008, 10 (2): 350—353

[3] Welton T. Chem. Rev., 1999, 99: 2071—2083

[5] Hapiot P, LagrostC., Chem. Rev., 2008, 108: 2238—2264

[5] Lall S I, Mancheno D, Castro S, Behaj V, Cohen J I, Engel R. Chem. Commun., 2000, 2413—2414

[6] Demberelnyamba D, Shin B K, Lee H. Chem. Commun., 2002, 1538—1539

[7] Ignat’ev N V, Bissky G, Willner H. Journal of Fluorine Chemistry, 2005, 126(8): 1150—1159

[8] Quek S K, IIya M L, HanV H. Tetrahedron, 2006, 62(13): 3137—3145

[9] Dana B, Nikolai I, Helge W. Journal of Fluorine Chemistry, 2010, 131(3): 325—332

[10] Han H B, Nie J, Liu K, Li W K, Feng W F, Michel A, ArmandM, Matsumoto H, Zhou Z B. Electrochimica Acta., 2010, 55: 1221—1226

[11] Cheng J Y, Chu Y H. Tetrahedron Letters, 2006, 47(10): 1575—1579

[12] Anderson J L, Ding R, Ellern A, Armstong D W. Journal of Americal Chemical Society, 2005, 127: 593—604

[13] Gu Z, Brennecke J F. J. Chem. Eng. Data, 2002, 47(2): 339—345

[14] Bonhte P, Dias A P, Papageorgiou N, Kalyanasundaram K, Grtzel M. Inorg. Chem., 1996, 35: 1168—1178

[15] Fitchett B D, Knepp T N, Conboy J C. J. Electrochem. Soc., 2004, 151(7): E219—E225

[16] Jiqin Z, Jian C, Chengyue L, Weiyang F. J. Chem. Eng. Data, 2007, 52: 812—816

[17] Tokuda H, Hayamizu K, Ishii K, Susan M A B H, Watanabe M. J. Phys. Chem. B, 2004, 108: 16593—16600

[18] McEwen A B, Ngo H L, LeCompte K, Goldman, J L. J. Electrochem. Soc., 1999, 146: 1687—1695

[19] Dzyuba S V, Bartsch R A. Chem Phys Chem, 2002, 3(2): 161—166

[20] Every H A, Bishop A G, MacFarlane D R, Ordd G, ForsythM. Phys. Chem. Chem. Phys., 2004, 6: 1758—1765

[21] Forsyth C M, MacFarlane D, Golding J J, Huang J F, SunJ, Forsyth M. Chem. Mater., 2002, 14: 2103—2108

[22] Noda A, Hayamizu K, Watanabe M. J. Phys. Chem. B, 2001, 105: 4603—4610

[23] Izgorodina E I, Forsyth M, MacFarlane D. Aust. J. Chem., 2007, 60: 15—20

[24] Tokuda H, Hayamizu K, Ishii K, Susan M A B H, WatanabeM. J. Phys. Chem. B, 2005, 109: 6103—6110

[25] Huddleston J G, Visser A E, Reichert W M, Willauer H D, Broker G A, Rogers R D. Green Chem., 2001, 3: 156—164

[26] Okoturo O O, Van der Noot T J. Journal of Electroanalytical Chemistry, 2004, 568: 167—181

[27] Ann E V, Reichert W M, Swatloski R P, Willauer H D, Huddleston J G, Rogers R D. ACS Symposium Series, 2002, 818: 289—308

[28] Fuller J, Carlin R T, Osteryoung R A. J. Electrochem. Soc., 1997, 144: 3881—3886

[29] Nanjundiah C, Mc Devitt F, Koch V R. J. Electrochem. Soc., 1997, 144: 3392—3397

[30] Carlin R T, Fuller J. Chem. Commun., 1997, 15: 1345—1347

[31] Galinski M, Lewandowski A, Stepniak I. Electrochim. Acta., 2006, 51(26): 5567—5580

[32] MacFarlane D, Sun J, Golding J J, Meakin P, Forsyth M. Electrochim. Acta., 2000, 45: 1271—1278

[33] Zistler M, Wachter P, Wasserscheid P, Gerhard D, Hinsch A, Sastrawan R, Gores H J. Electrochim. Acta., 2006, 52(1): 161—169

[34] Kosmulski M, Osteryoung R A, Ciszkowska M. J. Electrochem. Soc., 2000, 147: 1454—1458

[35] Schrder U, Wadhawan J D, Compton R G, Marken F, Suarez P A Z, Consorti C S, de Souza R F, Dupont J. New J. Chem., 2000, 24: 1009—1015

[36] Carlin R T, De Long H C, Fuller J, Trulove P C. J. Electrochem. Soc., 1998, 145: 1598—1607

[37] Comminges C, Barhdadi R, Laurent M, Troupel M. J. Chem. Eng. Data, 2006, 51(2): 680—685

[38] Evans R G, Klymenko O V, Hardacre C, Seddon K R, Compton R G. J. Electroanal. Chem., 2003, 556: 179—188

[39] Cammarata L, Kazarian S G, Salter P A, Welton T. Phys. Chem. Chem. Phys., 2001, 3: 5192—5200

[40] Widegren J A, Laesecke A, Magee J W. Chem. Commun., 2005, 1610—1612

[41] Visser A, Swatloski R, Reichert W, Griffin S, Rogers R. Ind. Eng. Chem. Res., 2000, 39: 3596—3604

[42] Huddleston J, Visser A, Reichert W, Willauer H, Broker G, Rogers R. Green Chemistry, 2001, 3: 156—164

[43] Seddon K R, Stark A, Torres M J. Pure Appl. Chem., 2000, 72(12): 2275—2287

[44] Xiao L, Johnson K E. J. Electrochem. Soc., 2003, 150: E307—E311

[45] Li Z P, Du Z Y, Gu Y L, Zhu L Y, Zhang X P, Deng Y Q. Electrochem. Commun., 2006, 8(8): 1270—1274

[46] Villagran C, Banks C E, Hardacre C, Compton R G. Anal. Chem., 2004, 76: 1998—2003

[47] Suarez P A Z, Consorti C S, de Souza R F, Dupont J, Gonalves R S. J. Braz. Chem. Soc., 2002, 13(1): 106—109

[48] Suarez P A Z, Selbach V M, Dullius J E L, Einloft S, Piatnicki C M S, Azambuja D S, de Souza R F, Dupont J. Electrochim. Acta., 1997, 42(16): 2533—2535

[49] MacFarlane D, Meakin P, Amini N, Forsyth M. J. Phys. Chem. B, 1999, 103: 4164—4170

[50] Matsumoto H, Yanagida M, Tanimoto K, Nomura M, Kitagawa Y, Miyazaki Y. Chem. Lett., 2000(29): 922—923

[51] Sun J, Forsyth M, MacFarlane D. J. Phys. Chem. B, 1998, 102: 8858—8864

[52] Hultgren V M, Mariotti A W A, Bond A M, Wedd A G. Anal. Chem., 2002, 74: 3151—3156

[53] Rogers E I, Silvester D S, Jones S E W, Aldous L, Hardacre C, Russell A J, Davies S G, Compton R G. J. Phys. Chem. C, 2007, 111(37): 13957—13966

[54] Paddon C A, Silvester D S, Bhatti F L, Donohoe T J, Compton R G. Electroanalysis, 2007, 19: 11—22

[55] Boxall D L, O’Dea J J, Osteryoung R A. J. Electrochem. Soc., 2002, 149: E468—E471

[56] Villagrán C, Banks C E, Pitner W R, Hardacre C, Compton R G. Ultrasonics Sonochemistry, 2005, 12(6): 423—428

[57] Feroci M, Elinson M, Rossi L, Inesi A. Electrochem. Commun., 2009, 11(7): 1523—1526

[58] Silvester D S, Wain A J, Aldous L, Hardacre C, Compton R G. J Electroanal Chem., 2006, 596(2): 131—140

[59] Lu J X, Sun Q, He M Y. Chin. J. Chem., 2003, 21: 1229—1230

[60] Doherty A P, Brooks C A. Electrochimica Acta, 2004, 49: 3821—3826

[61] Zhao N, Dong W J, Shi Q Z. Electrochemistry, 2006, 12 (1): 80—84

[62] Chu D B, Hou Y Y, He J G, Xu M, Wang Y Q, Wang S X, Wang J, Zha L W. J. Nanopart. Res., 2009, 11: 1805—1809

[63] 褚道葆(Chu D B), 张莉艳(Zhang L Y), 张金花(Zhang J H), 张秀梅(Zhang X M), 尹晓娟(Yin X J). 物理化学学报(Acta Phys. -Chim. Sin. ), 2006, 22(3): 373—377

[64] Chu D B, QinG X, Yuan X M, Xu M, Lu J, Zheng P. J. Porous Mater, 2008, 15: 661—665

[65] Cadena C, Anthony J, Shah J, Morrow T, Brennecke J, Maginn E. J. American Chem. Soc., 2004, 126(16): 5300—5308

[66] Yang H Z, Gu Y L, Deng Y Q, Shi F. Chem. Commun., 2002(3): 274—275

[67] Chu D B, Qin G X, Yuan X M, Xu M, Zheng P, Lu J. ChemSusChem, 2008, 1: 205—209

[68] Wang H, ZhangG R, Liu Y Z, Luo Y W, Lu J X. Electrochem. Commun., 2007, 9(9): 2235—2239

[69] Barhdadi R, Comminges C, Doherty A P, Ne · de · lec J Y, O’Toole S, Troupel M. J. Appl. Electrochem., 2007, 37: 723—728

[70] Ren T, Liu Y C, Guo Q X. Bull. Chem. Soc. Jpn., 1996, 69(10): 2935—2941

[71] AlNashef I M, Leonard M L, Matthews M A, Weidner J W. Ind. Eng. Chem. Res., 2002, 41(18): 4475—4478

[72] Villagrán C, Aldous L, Lagunas M C, Compton R G, Hardacre C. J. Electroanal. Chem., 2006, 588: 27—31

[73] Zhao G Y, JiangT, Wu W Z, Han B X, Liu Z M, Gao H X. J. Phys. Chem. B, 2004, 108(34): 13052—13057

[74] Allen G D, Buzzeo M C, Villagrán C, Hardacre C, Compton R G. J. Electroanal. Chem., 2005, 575: 311—320

[75] Allen G D, Buzzeo M C, Davies I G, Villagrán C, Hardacre C, Compton R G. J. Phys. Chem. B, 2004, 108: 16322—16327

[76] Palombi L, Bocchino C, Caruso T, Villano R, Scettri A. Tetrahedron Letters, 2008, 49: 5611—5613

[77] Safavi A, Maleki N, Farjami F, Farjami E. J. Electroanal. Chem., 2009, 626(1/2): 75—79

[78] 褚道葆(Chu D B), 张雪娇(Zhang X J), 何建国(He J G), 侯源源(Hou Y Y), 肖英(Xiao Y). 化学学报(Acta Chimica Sinica), 2010, 68(2): 125—130

[79] 褚道葆(Chu D B), 查龙武(Zha L W), 王树西(Wang S X), 王建(Wang J), 肖英(Xiao Y), 侯源源(Hou Y Y), 何建国(He J G), 张雪娇(Zhang X J). 电化学(Electrochemistry), 15(3): 299—302

[80] Ho K P, Wong K Y, Chan T H. Tetrahedron, 2006, 62(28): 6650—6658

[81] Tang M C Y, Wong K Y, Chan T H. Chem. Commun., 2005(10): 1345—1347

[82] Martiz B, Keyrouz R, Gmouh S, Vaultier M, Jouikov V. Chem. Commun., 2004(6): 674—675

[83] GaillonL, BediouiF. Chem. Commun., 2001(16): 1458—1459

[84] Meurs J H H, Eilenberg W. Tetrahedron, 1991, 47(4/5): 705—714

[85] Momota K, Morita M, Matsuda Y. Electrochim. Acta., 1993, 38: 1123—1130

[86] Hasegawa M, Ishii H, Fuchigami T. Green Chem., 2003, 5: 512—515

[87] Ilayaraja N, Radhakrishnan S, Renganathan N G. Ionics, 2010, 16: 137—144

[88] Mellah M, Zeitouny J, Gmouh S, Vaultier M, JouikovV. Electrochem. Commun., 2005, 7(9): 869—874

[89] Mellah M, Gmouh S, Vaultier M, Jouikov V. Electrochem. Commun., 2003, 5(7): 591—593

[90] Barhdadi R, Courtinard C, Nédélec J Y, Troupel M. Chem. Commun., 2003, 1434—1435

[91] Markus S, Bernd S. Electrochim. Acta, 2009, 54(14): 3735—3744

[92] Niu D F, Zhang A J, Xue T, Zhang J B, Zhao S F, Lu J X. Electrochem. Commun., 2008, 10(10): 1498—1501

[93] Duran P L, Elsevier C J, Rothenberg G. Adv. Synth. Catal., 2006, 348: 1705—1710

[94] Hasegawa M, Fuchigami T. Electrochim. Acta, 2004, 49: 3367—3372

[95] 董彬(Dong B), 徐景坤(Xu J K), 郑利强(Zheng L Q). 化学进展(Progress in Chemistry), 2009, 21(9): 1792—1799

[96] Sekiguchi K, Atobe M, Fuchigami T J. Electroanal. Chem., 2003, 557: 1—7

[97] Kubisa P. Progress in Polymer Science, 2004, 29(1): 3—12

[98] Elabedin S Z, Borissenko N, Endres F. Electrochem. Commun., 2004, 6(4): 422—426

[99] Wagner M, Kvarnstrm C, Ivaska A, Electrochim. Acta, 2010, 55(7): 2527—2535

[100] Sekiguchi K, Atobe M, Fuchigami T. Electrochem. Commun., 2004, 4: 881— 885

[101] Pringle J M, Efthimiadis J, Howlett P C, Efthimiadis J, MacFarlane D R, Chaplin A B, Hall S B, Officer D L, Wallace G G, Forsyth M. Polymer, 2004, 45(5): 1447—1453

[102] Zhang A J, Chen J, Niu D F, Wallace G G., Lu J X. Synthetic Metals, 2009, 159(15/16): 1542—1545

[103] Deepa M, Ahmad S. European Polymer Journal, 2008, 44(10): 3288—3299

[104] Li M C, Ma C A, Liu B Y, Jin Z M. Electrochem. Commun., 2005, 7(2): 209—212

[105] 刘宝友(Liu B Y), 许丹倩(Xu D Q), 徐振元(Xu Z Y). 中国化学(Chin. J Chem. ), 2005, 23(7): 803—805

[106] Wei D, Kvarnstrm C, Lindfors T, Ivaska A. Electrochem. Commun., 2006, 8 (10): 1563—1566

[107] Du Y F, Wang H, Zhang A J, Lu J X. Chinese Science Bulletin, 2007, 52 (16): 2174—2178

[108] Murray P S, Ralph S F, Too C O, Wallace G G. Electrochim. Acta., 2006, 51: 2471—2476

[109] Pang Y H, Li X Y, Ding H L, Shi G Y, Jin L T. Electrochim. Acta., 2007, 52(20): 6172—6177

[110] Dong B, Xing Y H, Xu J K, Zheng L Q, Hou J, Zhao F. Electrochim. Acta., 2008, 53(19): 5745—5751

[111] Dong B, Zheng L Q, Xu J K, Liu H T, Pu S Z. Polymer, 2007, 48(19): 5548—5555

[112] Dong B, Song D F, Zheng L Q, Xu J K, Li N, J Electroana. Chem., 2009, 633(1): 63—70

[113] Pang Y H, Xu H, Li X Y, Ding H L, Cheng Y X, Shi G Y, Jin L T. Electrochem. Commun., 2006, 8(11): 1757—1763

[1] 刘亚伟, 张晓春, 董坤, 张锁江. 离子液体的凝聚态化学研究[J]. 化学进展, 2022, 34(7): 1509-1523.
[2] 康美荣, 金福祥, 李臻, 宋河远, 陈静. 离子液体固载化及应用研究[J]. 化学进展, 2020, 32(9): 1274-1293.
[3] 刘风国, 王博, 章莲玉, 刘爱民, 王兆文, 石忠宁. 离子液体在电沉积铝及铝合金中的应用[J]. 化学进展, 2020, 32(12): 2004-2012.
[4] 佟国宾, 鄂雷, 徐州, 马春慧, 李伟, 刘守新. 基于离子液体的炭材料制备、改性及应用[J]. 化学进展, 2019, 31(8): 1136-1147.
[5] 苏红, 韩业君. 亲电微生物及其催化的CO2固定和合成[J]. 化学进展, 2019, 31(2/3): 433-441.
[6] 李志勇, 冯莹, 王慧勇, 袁晓晴, 赵玉灵, 王键吉. 光响应离子液体的结构与性能调控[J]. 化学进展, 2019, 31(11): 1550-1559.
[7] 刘文巧, 李臻, 夏春谷. 酸功能化离子液体固相催化材料的制备及应用[J]. 化学进展, 2018, 30(8): 1143-1160.
[8] 程海东, 陈双俊*. 功能化离子液体在聚酯PET降解与合成中的应用[J]. 化学进展, 2017, 29(4): 443-449.
[9] 宋河远, 康美荣, 靳荣华, 金福祥, 陈静. 离子液体在羰基化反应中的应用[J]. 化学进展, 2016, 28(9): 1313-1327.
[10] 杨许召, 王军, 方云. 双阳离子液体的合成、性能及应用[J]. 化学进展, 2016, 28(2/3): 269-283.
[11] 孟艳山, 陈玉焕, 邓雨晨, 张姝明, 王桂香. 离子液体及离子液体膜在天然气净化方面的应用[J]. 化学进展, 2015, 27(9): 1324-1332.
[12] 徐艺凇, 张凤香, 厉嘉云, 白赢, 肖文军, 彭家建. 聚乙二醇功能化离子液体的制备及其在有机反应中的应用[J]. 化学进展, 2015, 27(10): 1400-1412.
[13] 王雪珠, 谭忱, 李永琪, 张恒, 刘晔. 离子型膦配体及其离子型过渡金属配合物的合成和均相催化作用[J]. 化学进展, 2015, 27(1): 27-37.
[14] 李善建, 冯拉俊. 功能离子液体杂化固相纳米材料的制备及催化应用[J]. 化学进展, 2014, 26(10): 1633-1644.
[15] 孙晓杰, 邢钧, 翟毓秀, 李兆新. 离子液体在气相色谱固定相中的应用[J]. 化学进展, 2014, 26(04): 647-656.