CN107793442B - 一种四氟硼酸季铵盐的制备方法 - Google Patents
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- -1 tetrafluoroborate quaternary ammonium salt Chemical class 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 9
- 239000004327 boric acid Substances 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000001348 alkyl chlorides Chemical class 0.000 abstract description 2
- 239000002168 alkylating agent Substances 0.000 abstract description 2
- 229940100198 alkylating agent Drugs 0.000 abstract description 2
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- 239000003990 capacitor Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
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- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
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- 238000001514 detection method Methods 0.000 description 3
- 238000004896 high resolution mass spectrometry Methods 0.000 description 3
- 238000004255 ion exchange chromatography Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
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- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JAJRRCSBKZOLPA-UHFFFAOYSA-M triethyl(methyl)azanium;hydroxide Chemical compound [OH-].CC[N+](C)(CC)CC JAJRRCSBKZOLPA-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
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Abstract
本发明提供一种四氟硼酸季铵盐的制备方法，其制备步骤包括：(1)胺与硼酸烷基酯在有机溶剂中季铵化反应生成硼酸类季铵盐；(2)硼酸类季铵盐与氢氟酸反应，得四氟硼酸季铵盐。该法使用硼酸烷基酯作为烷基化试剂，没有使用氯代烷，或溴代烷，因此无氯离子、溴离子残留，并且使用廉价的氢氟酸代替四氟硼酸来生成四氟硼酸盐，降低了生产成本。
Description
技术领域
本发明涉及一种四氟硼酸季铵盐的制备方法，特别是作为超级电容器电解质的四氟硼酸季铵盐的制备方法。
背景技术
超级电容器，又叫做双层电容器(Ectrochemical Double-Layer Capacitors,EDLCs)，比传统静电电容器有更高的能量密度，比二次电池有更大的功率密度，是介于普通电池与传统静电电容器之间的新型能量储存器件。由于超级电容器具有功率密度高，循环寿命长，充放电时间短和使用温度范围宽等优点，具有广阔的应用前景，成为了研究的热点。
电解质是超级电容器的重要组成部分，对超级电容器的性能有很大的影响。季铵盐，特别是甲基三乙基四氟硼酸铵、N,N-二甲基吡咯四氟硼酸铵、1,3-二甲基咪唑四氟硼酸铵，在极性有机溶剂中有良好的溶解性，具有较高的电导率；几乎没有蒸汽压，可以消除因挥发对环境产生的污染；工作温度范围宽、防爆性能和阻燃性能较好，具有较高的安全性能等优点，广泛用作超级电容器电解质。
用作超级电容器电解质的四氟硼酸类季铵盐，如甲基三乙基四氟硼酸铵、N,N-二甲基吡咯四氟硼酸铵、1,3-二甲基咪唑四氟硼酸铵，其制备方法有以下三种：(1)方法一，是先将卤代季铵盐转化成季铵碱，再与相应的酸中和反应，得到目标产品。专利CN 104892433A公布了一种甲基三乙基四氟硼酸铵的制备方法，是先制备甲基三乙基氯化铵，再与氢氧化钠或氢氧化钾反应转化成甲基三乙基氢氧化物，再与四氟硼酸反应，得到甲基三乙基四氟硼酸铵。该合成方法有卤化物参与，卤素离子不易去除干净，会影响超级电容器的电化学性能。为了尽量脱除卤素离子，专利JP 2011192963 A利用氧化银与甲基三乙基氯化铵在水溶液中反应，制备甲基三乙基氢氧化物，再与四氟硼酸反应，得到甲基三乙基四氟硼酸铵。虽然此方法可以几乎完全去除卤素离子，但成本太高。(2)方法二，以硫酸烷基酯为烷基化试剂与胺反应制备硫酸类季铵盐，再与相应的酸反应，得到目标产品。专利CN 101328128 A公布了将二乙胺或三乙胺与硫酸二甲酯季铵化反应，生成硫酸类季铵盐，再与四氟硼酸反应得到相应的产品。该方法虽然合成工艺简单，收率高，并且没有卤素离子的引入，但硫酸烷基酯毒性大，对环境污染严重，所以限制了其使用。(3)方法三，以碳酸烷基酯为烷基化试剂与胺反应制备碳酸类季铵盐，再与相应的酸反应，得到目标产品。专利CN 102584602 A公布了将正三丙胺或哌嗪与碳酸二甲酯季铵化反应，生成碳酸类季铵盐，再与四氟硼酸反应得到相应的产品。该方法虽然没有卤素离子的引入，但是碳酸烷基酯的活性低，反应需要在耐压釜中进行，工艺条件复杂，增加了生产成本。
发明内容
本发明的目的在于克服上述四氟硼酸类季铵盐制备方法的不足，提供一种四氟硼酸季铵盐的制备方法。
本发明目的的实现，步骤如下：
(1)胺与硼酸烷基酯在有机溶剂中季铵化反应生成硼酸类季铵盐；
(2)硼酸类季铵盐与氢氟酸反应，得四氟硼酸季铵盐。
所述步骤(1)中，胺为以下结构的一种，代表性分子结构如下：
其中：R1代表氢或C1～C4烷基；R2、R3代表C1～C4烷基。
所诉步骤(1)中，硼酸烷基酯为硼酸三甲酯、硼酸三乙酯中的一种。
所诉步骤(1)中，有机溶剂为硼酸烷基酯对应的醇、四氢呋喃中的一种。
所诉步骤(1)中，胺与硼酸烷基酯的摩尔比为1:1～3:1，反应温度为60℃～200℃，反应时间为4h～18h。
所诉步骤(2)中，硼酸类季铵盐与氢氟酸的摩尔比为1:4～1:5，反应温度为10℃～90℃，反应时间为1h～6h。
有益效果：本发明的优点在于使用硼酸烷基酯作为烷基化试剂，没有使用氯代烷，或溴代烷，因此无氯离子、溴离子残留，因此无氯离子、溴离子残留；并且使用廉价的氢氟酸代替四氟硼酸来生成四氟硼酸盐，降低了生产成本。
具体实施方法
以下结合具体实施例对本申请进行示例性说明和进一步理解，但实施例仅作为例子给出，不视为本发明的全部技术方案，不是对本发明总的技术方案的限定。凡具有相同或相似技术特征，简单改变或替换的，均属本发明保护范围。
实施例1
将硼酸三甲酯(10.39g，0.1mol)，三乙胺(15.15g，0.15mol)，20mL甲醇，加入到高压反应釜中，搅拌，135℃左右反应9h。反应结束后，旋蒸脱溶剂，得甲基三乙基硼酸类季铵盐。
将40％的氢氟酸水溶液(22.51g，0.45mol)，滴加到甲基三乙基硼酸类季铵盐溶液中，40℃左右反应4h，旋蒸脱溶剂，得粗产品。用乙醇重结晶，得到甲基三乙基四氟硼酸铵13.90g。
1H-NMR(D2O)δ，ppm：1.29～1.33(t，9H，N-CH2-CH3)，2.93～3.01(s，3H，N-CH3)，3..30～3.34(q，6H，N-CH2)。
13C-NMR(D2O)：
高分辨质谱：M+＝116.144，M-＝87.004。
经离子色谱检测，结果如下：
实施例2
将硼酸三甲酯(10.39g，0.1mol)，N-甲基吡咯烷(12.77g，0.15mol)，20mL甲醇，加入到高压反应釜中，搅拌，130℃左右反应9h。反应结束后，旋蒸脱溶剂，得N,N-二甲基吡咯硼酸类季铵盐。
将40％的氢氟酸水溶液(22.51g，0.45mol)，滴加到N,N-二甲基吡咯硼酸类季铵盐溶液中，40℃左右反应4h，旋蒸脱溶剂，得粗产品。用乙醇重结晶，得到N,N-二甲基吡咯四氟硼酸铵15.75g。
1H-NMR(D2O)δ，ppm：2.21～2.35(t，4H，CH2)，3.08～3.15(s，6H，N-CH3)，3.56～3.64(q，4H，N-CH2)。
13C-NMR(D2O)：
高分辨质谱：M+＝100.113，M-＝87.004。
经离子色谱检测，结果如下：
实施例3
将硼酸三甲酯(10.39g，0.1mol)，1-甲基咪唑(12.32g，0.15mol)，20mL甲醇，加入到高压反应釜中，搅拌，125℃左右反应7h。反应结束后，旋蒸脱溶剂，得1,3-二甲基咪唑硼酸类季铵盐。
将40％的氢氟酸水溶液(22.51g，0.45mol)，滴加到1,3-二甲基咪唑硼酸类季铵盐溶液中，40℃左右反应4h，旋蒸脱溶剂，得粗产品。用乙醇重结晶，得到1,3-二甲基咪唑四氟硼酸铵14.36g。
1H-NMR(D2O)δ，ppm：3.79～3.86(s，6H，CH3)，7.43～7.52(s，2H，CH)，8.70～8.83(s，1H，CH)。
13C-NMR(D2O)：
高分辨质谱：M+＝97.135，M-＝87.004。经离子色谱检测，结果如下：
Claims (6)
1.一种四氟硼酸季铵盐的制备方法，其特征在于该方法步骤如下：
(1)胺与硼酸烷基酯在有机溶剂中季铵化反应生成硼酸类季铵盐；
(2)硼酸类季铵盐与氢氟酸反应，得四氟硼酸季铵盐。
2.根据权利要求1所述的一种四氟硼酸季铵盐的制备方法，其特征在于，所诉步骤(1)中胺为以下结构的一种，代表性分子结构如下：
其中：R1代表氢或C1～C4烷基；R2、R3代表C1～C4烷基。
3.根据权利要求1所述的一种四氟硼酸季铵盐的制备方法，其特征在于，所诉步骤(1)中硼酸烷基酯为硼酸三甲酯、硼酸三乙酯中的一种。
4.根据权利要求1所述的一种四氟硼酸季铵盐的制备方法，其特征在于，所诉步骤(1)中有机溶剂为硼酸烷基酯对应的醇、四氢呋喃中的一种。
5.根据权利要求1所述的一种四氟硼酸季铵盐的制备方法，其特征在于，所诉步骤(1)中胺与硼酸烷基酯的摩尔比为1:1～3:1，反应温度为60℃～200℃，反应时间为4h～18h。
6.根据权利要求1所述的一种四氟硼酸季铵盐的制备方法，其特征在于，所诉步骤(2)中硼酸类季铵盐与氢氟酸的摩尔比为1:4～1:5，反应温度为10℃～90℃，反应时间为1h～6h。
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