CN1061038C - 疏水液体盐、其制备方法及其在电化学中的应用 - Google Patents
疏水液体盐、其制备方法及其在电化学中的应用 Download PDFInfo
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Abstract
本发明提供通式如下的疏水液体盐，式中，R1和R3相同或不同，各自代表直链或支链烷基、具有1-8个碳原子的氟代烷基或烷氧基烷基；R2、R4和R5相同或不同，各自代表氢原子或具有1-3个碳原子的烷基。本发明的疏水液体盐可在电化学光电池中用作电解质溶剂。
Description
本发明的目的是提供新的、在室温下粘度低的、具有N，N′-二烷基咪唑鎓阳离子和二-三氟甲磺酰胺(CF3SO2)2N-阴离子的疏水液体盐及其制备方法。
本发明还涉及所述盐在电化学或合成应用中作为疏水性极性溶剂的用途，例如用作电化学光电池用电解质组合物中的溶剂。因此本发明还涉及含电解质组合物和碘／三碘化物电对的电化学光电池，其中的电解质组合物含有本发明的疏水液体盐。
具有取代的咪唑鎓阳离子和三氟甲磺酸根阴离子、在环境温度下为液体的盐是已知的。所述化合物被描述于E．J．Cooper和E．J．M．O′Sullivan的文章(The E1ectrochem．Soc．，Proceedings Vol．92-16(1992))中。各化合物的粘度不同，但除了实际上在室温下为固体(熔点：32℃)的三氟甲磺酸十二烷基-1-乙基-3-咪唑鎓之外，均与水相溶(亲水性的)。
US4505997描述了新的化合物，即通过离子交换由相应的四丁基铵制得的二-三氟甲磺酰胺的碱金属盐。这些盐是用来混入聚合物基体的固体化合物，用以形成生产初级电化学发生器或次级电化学发生器所用的固体电解质。而且，所述这些盐是强疏水性的，这实际上是发明人赋予所述二-三氟甲磺酰胺阴离子的特性。
我们现在惊人地发现，由取代的咪唑鎓阳离子和二-三氟甲磺酰胺阴离子组成的盐在环境温度下是液体，它是疏水性的并具有略高的粘度(有利于离子的运动)、较高的导电性、高的热稳定性(至少为300℃)、在环境温度下不高并且在150℃下小于0．1毫巴的蒸汽压、宽的电化学稳定性范围(与碘／三碘化物电对比较至少为-2V至2V)。所有这些性能都使得这类盐能够有利地用作电化学体系(如电化学光电池)的溶剂或者合成所需的非质子传递极性溶剂。
本发明的化合物可用下式表示：
式中，R1和R3相同或不同，各自代表直链或支链烷基、具有1-8个碳原子的氟代烷基或烷氧基烷基；R2，R4和R5相同或不同，各自代表氢原子或具有1-3个碳原子的烷基。
优选的情况是：R1和R3代表甲基、乙基、丁基、异丁基、辛基、甲氧基乙基或2，2，2-三氟乙基；R2，R4或R5代表氢、甲基或乙基。
本发明还涉及通过在水性介质中使碱金属(优选锂)的二-三氟甲磺酰胺与取代的咪唑鎓卤化物(优选溴化物或碘化物)之间按照下述反应式发生离子交换而获得所述化合物的方法：
二-三氟甲磺酰胺锂是市售化合物，例如可以从3M公司(St．Panl Minnesota，USA)购得。
碱金属的二-三氟甲磺酰胺也可以按照已知的先有技术的方法，例如按照EP0096629的方法由五氟烷磺酸酐出发制备，或者按照J．R．Foroponlos和D．D．Desmartean(Inorg．Chem．23，3720-3723)所述的方法由五氟烷磺酸的氟化物出发制备。
取代的咪唑鎓卤化物是用已知的方法通过在有机溶剂中在搅拌下使烷基卤化物R3X与被R1、R2、R4和R5 适当取代的咪唑反应制得的。
下面给出的非限定性实施例描述了本发明的某几种化合物的制备方法，以及使它们适合用作电解质溶剂的物理化学和电化学性能。
实施例1甲基-1-丁基-3-咪唑鎓-二-三氟甲磺酰胺。
将0．1摩尔(8．2g)甲基-1-咪唑溶于200ml在反应容器中的三氯乙烷中，然后在环境温度和剧烈搅拌下滴加丁基溴(16．44g，0．12摩尔)的三氯乙烷(100ml)溶液。然后将混合物加热回流2小时并滗析之。溴化甲基-1-丁基-3-咪唑鎓以液体的形式分出。然后用100ml 50℃的三氯乙烷将该溴化物洗涤两次，在0．1毫巴的负压下在150℃的旋转蒸发器中干燥1小时，得15．3g(收率：70％)溴化甲基-1-丁基-3-咪唑鎓。
将50mmol(11g)上步得到的溴化物随后溶解在50ml水中，向其中一次加入二-三氟甲磺酰胺锂(50mmol，14．35g)的水(50ml)溶液。溶液立即变浑浊，滗析后，溶液成为两相。除去上层水相后，用50ml水将液体盐洗涤两次，然后在0．1毫巴的负压下于150℃干燥1小时。得到18．9g本发明的产物(收率：90％)，为不溶于水的无色液体，折射指数n=1．4271。该液体的凝固点低于-25℃。所得产物的疏水性可通过将产物预先在水中饱和，以Karl Fisher滴定法滴定得其水含量仅为1．4％(体积)而被证实。
该化合物的密度在20℃下的测定值为d=1．429克／立方厘米，动力学粘度测定在20℃下用Haake球形微粘度计进行，粘度系数的值η=52．4厘泊。
作为比较，先有技术已知的均相化合物甲基-1-丁基-3-咪唑鎓-二-三氟甲磺酸盐的熔点为16℃，它可溶于水且粘度η=90厘泊。
还发现本发明的化合物具有高达300℃的热稳定性和非常低的蒸汽压(在150℃低于0．1毫巴)。
在20℃用Autolab电势恒定器频率分析仪测定的该液体的电导σ=3．88mS／cm，该值与三氟甲磺酸盐类似物的为同一数量级(σ=3．68mS／cm)。
图1所示的环伏安曲线是在20℃用表面积为0．78平方毫米的铂工作电极和铂参比电极与在相同的液体盐中的碘／三碘化物电对接触测得的，其扫描范围为50mV／s，该曲线表明本发明的化合物在-2．0V至+2．2V的范围内具有高的电化学稳定性。
实施例2甲基-1-乙基-3-咪唑鎓-二-三氟甲磺酰胺
使用类似于实施例1的两步法，但在第一步中用0．25摩尔(27．75g)乙基溴代替0．12摩尔丁基溴，得到54g(收率：78％)本发明的产物，为具有如下物理化学性能的无色液体：
凝固点 ＜-25℃
含水率 (Karl Fisher)： 1．4％
d20=1．52g·cm-3 η=34．3cP
nD=1．4231 σ=8．84 mS·cm-1
在与实施例1相同的条件下进行环伏安曲线的测定，曲线表明本发明的化合物的电化学范围在-2．0V至+2．2V之间。
实施例3乙基-1-丁基-3-咪唑鎓-二-三氟甲磺酰胺
如实施例1所示进行，但由0．1摩尔(9．6g)乙基-1-咪唑出发，得到13g(收率：60％)本发明的产物，为具有如下物理化学性能的无色液体：
凝固点 ＜-25℃
含水率 (Karl Fisher)： 1．3％
d20=1．52g cm-3 η=47．6cP
nD=1．4285 σ=4．12ms·cm-1
按照与实施例1-3相同的方法，但从不同的取代的咪唑出发制备了下述三氟甲磺酰胺的阳离子：甲基-1-丁基-3-咪唑鎓；甲基-1-甲氧基乙基-3-咪唑鎓；甲基-1-1，2，2，2-三氟乙基-3-咪唑鎓；乙基-1-乙基-3-咪唑鎓；甲基-1-甲基-2-乙基-3-咪唑鎓；乙基-1-甲基-2-乙基-3-咪唑鎓；甲基-1-乙基-3-甲基-5-咪唑鎓；乙基-1-乙基-3-甲基-5-咪唑鎓；乙基-1-异丁基-3-咪唑鎓；甲基-1-辛基-3-咪唑鎓。
实施例4以疏水液体盐为电解质溶剂的电化学光电池
制成如国际专利申请WO／04497所述那样的电化学光电池，它是由两个相距20μm的电极组件构成，其中一个电极被0．3μm厚的二氧化钛纳粒层(nanoparticulate layer)覆盖，上面吸附有敏化剂顺-二硫氰酸根合-二(2，2′-二吡啶基-4，4′-二甲酸铷(Ⅱ))，敏化剂的量应使得可见光在250nm处的吸收仅为5％。电极之间的自由空间填充着由以实施例1的液体盐为溶剂的10％(重量)碘化甲基己基咪唑鎓和10mmol碘组成的电解质。
在对应于1／100标准日光照明(AMI)的照明条件下，可得到530mV的开路电势和27μA／cm的短路电流。
用以实施例2的液体盐为溶剂的10％(重量)碘化甲基己基咪唑鎓和10mmol碘组成的电解质重复相同的实验，可得到550mV的开路电势和25μA／cm的短路电流。
还应当指出，用作电解质溶剂的液体盐的疏水性能够降低二氧化钛纳粒层的敏化剂的解吸附。与许多非质子传递极性溶剂不同，本发明的液体盐对于三碘化物是惰性的。
本实施例是为说明性而给出的，本领域技术人员将能够将本发明的疏水液体盐在不背离本发明范围的情况下用于电化学领域的其它应用。
Claims (9)
1．通式如下的疏水液体盐：
式中，R1和R3相同或不同，各自代表直链或支链烷基、具有1-8个碳原子的氟代烷基或烷氧基烷基；R2、R4和R5相同或不同，各自代表氢原子或具有1-3个碳原子的烷基。
2．根据权利要求1的疏水液体盐，其特征在于：R1或R3代表甲基、乙基、丁基、异丁基、辛基、甲氧基乙基或2，2，2-三氟乙基；R2、R4或R5代表氢、甲基或乙基。
3．根据权利要求1的疏水液体盐，其特征在于它对应于甲基-1-丁基-3-咪唑鎓-二-三氟甲磺酰胺。
4．根据权利要求1的疏水液体盐，其特征在于它对应于甲基-1-乙基-3-咪唑鎓-二-三氟甲磺酰胺。
5．根据权利要求1的疏水液体盐，其特征在于它对应于乙基-1-丁基-3-咪唑鎓-二-三氟甲磺酰胺。
6．制备权利要求1的疏水液体盐的方法，其特征在于使带有R1、R2、R3、R4和R5取代基的的咪唑鎓卤化物在水性介质中与碱金属-二-三氟甲磺酰胺反应，并通过滗析分离所得产物。
7．根据权利要求6的制备方法，其特征在于卤化物是溴化物或碘化物且碱金属是锂。
8．权利要求1的疏水液体盐在电解组合物中作为非质子传递极性溶剂的用途。
9．一种电化学光电池，它含有一种含权利要求1的疏水液体盐的电解组合物以及碘／三碘化物电对。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH03862/1994 | 1994-12-21 | ||
| CH386294A CH688236A5 (fr) | 1994-12-21 | 1994-12-21 | Sels liquides hydrophobes, leur préparation et leur application en électrochimie. |
| CH03862/94 | 1994-12-21 | ||
| FR9415704 | 1994-12-27 | ||
| FR9415704A FR2728569B1 (fr) | 1994-12-27 | 1994-12-27 | Sels liquides hydrophobes, leur preparation et leur application en electrochimie |
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| CN1132746A CN1132746A (zh) | 1996-10-09 |
| CN1061038C true CN1061038C (zh) | 2001-01-24 |
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| CN95119898A Expired - Lifetime CN1061038C (zh) | 1994-12-21 | 1995-12-20 | 疏水液体盐、其制备方法及其在电化学中的应用 |
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| US (1) | US5683832A (zh) |
| EP (1) | EP0718288B8 (zh) |
| JP (3) | JPH08259543A (zh) |
| CN (1) | CN1061038C (zh) |
| DE (1) | DE69534293T2 (zh) |
| ES (1) | ES2244958T3 (zh) |
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| US4463071A (en) * | 1983-11-30 | 1984-07-31 | Allied Corporation | Secondary batteries using room-temperature molten non-aqueous electrolytes containing 1,2,3-trialkylimidazolium halides or 1,3-dialkylimidazolium halide |
| US4463072A (en) * | 1983-11-30 | 1984-07-31 | Allied Corporation | Secondary batteries containing room-temperature molten 1,2,3-trialkylimidazolium halide non-aqueous electrolyte |
| JPH07107888B2 (ja) * | 1986-11-18 | 1995-11-15 | 旭硝子株式会社 | 電気二重層コンデンサ |
| JP2723543B2 (ja) * | 1988-07-28 | 1998-03-09 | 株式会社リコー | 画像形成装置 |
| JP2771607B2 (ja) * | 1989-06-22 | 1998-07-02 | 三菱化学株式会社 | 常温溶融塩の製造方法 |
| JPH04233212A (ja) * | 1990-12-28 | 1992-08-21 | Murata Mfg Co Ltd | 電気二重層コンデンサ |
| JPH04370663A (ja) * | 1991-06-18 | 1992-12-24 | Hitachi Maxell Ltd | 有機電解液電池 |
| JP3473090B2 (ja) * | 1994-03-30 | 2003-12-02 | 三菱化学株式会社 | 電気二重層コンデンサ用電解液 |
-
1995
- 1995-12-11 DE DE69534293T patent/DE69534293T2/de not_active Expired - Lifetime
- 1995-12-11 ES ES95119462T patent/ES2244958T3/es not_active Expired - Lifetime
- 1995-12-11 EP EP95119462A patent/EP0718288B8/fr not_active Expired - Lifetime
- 1995-12-18 US US08/574,317 patent/US5683832A/en not_active Expired - Lifetime
- 1995-12-20 CN CN95119898A patent/CN1061038C/zh not_active Expired - Lifetime
- 1995-12-21 JP JP7348992A patent/JPH08259543A/ja not_active Withdrawn
-
2006
- 2006-02-03 JP JP2006027313A patent/JP4504931B2/ja not_active Expired - Lifetime
-
2010
- 2010-02-18 JP JP2010034025A patent/JP5021778B2/ja not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0096629A1 (fr) * | 1982-06-01 | 1983-12-21 | ANVAR Agence Nationale de Valorisation de la Recherche | Bis perhalogénoacyl - ou sulfonyl - imidures de métaux alcalins, leurs solutions solides avec des matières plastiques et leur application à la constitution d'éléments conducteurs pour des générateurs électrochimiques |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2244958T3 (es) | 2005-12-16 |
| EP0718288B8 (fr) | 2005-10-26 |
| JP4504931B2 (ja) | 2010-07-14 |
| EP0718288B1 (fr) | 2005-06-29 |
| JP2006206594A (ja) | 2006-08-10 |
| US5683832A (en) | 1997-11-04 |
| JP2010180209A (ja) | 2010-08-19 |
| EP0718288A1 (fr) | 1996-06-26 |
| JPH08259543A (ja) | 1996-10-08 |
| CN1132746A (zh) | 1996-10-09 |
| DE69534293T2 (de) | 2006-05-18 |
| DE69534293D1 (de) | 2005-08-04 |
| JP5021778B2 (ja) | 2012-09-12 |
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