CN112708155B - 一种基于氰基结构侧链磺化聚芳醚离子交换膜及其制备方法 - Google Patents
一种基于氰基结构侧链磺化聚芳醚离子交换膜及其制备方法 Download PDFInfo
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- 125000004093 cyano group Chemical group *C#N 0.000 title claims abstract description 47
- 229920000090 poly(aryl ether) Polymers 0.000 title claims abstract description 47
- 239000003014 ion exchange membrane Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 15
- YXWJGZQOGXGSSC-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(F)=C1F YXWJGZQOGXGSSC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 7
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 7
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 4
- 239000011734 sodium Substances 0.000 claims abstract description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000005266 casting Methods 0.000 claims description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000011261 inert gas Substances 0.000 claims description 8
- BYMHXIQVEAYSJD-UHFFFAOYSA-M sodium;4-sulfophenolate Chemical compound [Na+].OC1=CC=C(S([O-])(=O)=O)C=C1 BYMHXIQVEAYSJD-UHFFFAOYSA-M 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- ZYZWCJWINLGQRL-UHFFFAOYSA-N 4-phenylcyclohexa-2,4-diene-1,1-diol Chemical group C1=CC(O)(O)CC=C1C1=CC=CC=C1 ZYZWCJWINLGQRL-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 239000012716 precipitator Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010025 steaming Methods 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012528 membrane Substances 0.000 abstract description 10
- 229910052720 vanadium Inorganic materials 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 3
- 125000000542 sulfonic acid group Chemical group 0.000 abstract description 3
- 229910001456 vanadium ion Inorganic materials 0.000 abstract description 3
- GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000005341 cation exchange Methods 0.000 abstract description 2
- 230000010220 ion permeability Effects 0.000 abstract description 2
- 238000005191 phase separation Methods 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- 238000004146 energy storage Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- -1 4-dihydroxy biphenyl Natural products 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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Abstract
本发明属于阳离子交换膜技术领域,提供了一种基于氰基结构侧链磺化聚芳醚离子交换膜及其制备方法。首先用五氟苯甲腈与4‑羟基苯磺酸钠合成4‑苯氧基‑4‑磺酸基‑2,3,5,6‑四氟苄腈,然后与双酚聚合得到基于氰基结构侧链磺化聚芳醚,并制膜。本发明的有益效果:氰基可以使聚合物主链更加稳定,支链型磺酸基团可以形成良好的微相分离。该基于氰基结构侧链磺化聚芳醚离子交换膜具有较高的质子传导率,较低的钒离子渗透率和较好的化学稳定性,在全钒液流电池中具有较好的应用前景。
Description
技术领域
本发明属于阳离子交换膜技术领域,涉及到一种基于氰基结构侧链磺化聚芳醚离子交换膜及其制备方法。
背景技术
随着对使用可再生能源的需求不断增长,大规模储能技术因其吸引人的特性而受到越来越多的关注。钒液流电池(VFB)是最有前途的大型储能技术之一,它具有安全性高,循环寿命长,功率和容量可分别调节,效率高和对环境友好等特点。对于VFB单电池,其主要组件由电极,电解质和膜组成。其中,膜是最重要的成分之一,它阻碍钒离子在阳极电解液和阴极电解液中传输,同时传输质子以形成内部回路。全氟化膜(如Nafion)是VFB应用中最常用的商业膜,尽管它具有高电导率,但仍受到高成本、低选择性和化学稳定性的限制。因此,迫切需要开发具有高电导率,高选择性,高稳定性以及低成本的商用VFB 应用的高性能膜。
发明内容
本发明提供了一种基于氰基结构侧链磺化聚芳醚离子交换膜及其制备方法。首先用五氟苯甲腈与4-羟基苯磺酸钠合成4-苯氧基-4-磺酸基-2,3,5,6- 四氟苄腈,然后与双酚聚合得到基于氰基结构侧链磺化聚芳醚,并制膜。本发明的有益效果:氰基可以使聚合物主链更加稳定,支链型磺酸基团可以形成良好的微相分离。该基于氰基结构侧链磺化聚芳醚离子交换膜具有较高的质子传导率,较低的钒离子渗透率和较好的化学稳定性,在全钒液流电池中具有较好的应用前景。
本发明的技术方案:
一种基于氰基结构侧链磺化聚芳醚离子交换膜,基于氰基结构侧链磺化聚芳醚的结构如下:
其中:n为正整数;
Ar为双酚,为4,4-二羟基联苯、双酚A、双酚AF或对苯二酚。
一种基于氰基结构侧链磺化聚芳醚离子交换膜的制备方法,步骤如下:
(1)4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈的合成:在惰性气体保护下,将五氟苯甲腈、4-羟基苯磺酸钠和碳酸钾溶解于溶剂N,N-二甲基甲酰胺中,在 0℃保持温度恒定反应24h;将反应溶液离心、萃取、旋蒸、干燥得到4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈;
所述的4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈结构式如下:
所述的五氟苯甲腈:4-羟基苯磺酸钠:碳酸钾的摩尔比为1.2:1:1.5;
所述的五氟苯甲腈、4-羟基苯磺酸钠和碳酸钾在溶剂N,N-二甲基甲酰胺中的w/v为10.9%~13.4%;
(2)基于氰基结构侧链磺化聚芳醚的合成:在惰性气体保护下,将4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈、双酚和碳酸钾溶解于溶剂二甲基亚砜中,在 30℃保持温度恒定反应40h;将反应溶液倒入沉淀剂A中,过滤、洗涤、干燥得到基于氰基结构侧链磺化聚芳醚;
所述的双酚为4,4-二羟基联苯、双酚A、双酚AF或对苯二酚;
所述的4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈:4,4-二羟基联苯:碳酸钾的摩尔比为1.:1:1.5;
所述的五氟苯甲腈、4-羟基苯磺酸钠和碳酸钾在溶剂A中的w/v为 10.9%~13.4%
所述的沉淀剂A为乙醇、水中的一种;
(3)基于氰基结构侧链磺化聚芳醚离子交换膜:取步骤(2)合成的基于氰基结构侧链磺化聚芳醚溶于溶剂B中,制成浓度为32g/L-37g/L的铸膜液;铸膜液滴加在铸膜玻璃板上,并在烘箱中充分烘干,制成厚度为30μm~40μm的基于氰基结构侧链磺化聚芳醚离子交换膜;
所述的溶剂B为N,N-二甲基乙酰胺、二甲基亚砜中的一种;
所述的铸膜液w/v为3.2~3.7%;
成膜的烘干温度为40~60℃,时间为24~48小时。
上述的w/v的单位均为g/ml。
本发明的效果和益处是通过缩合反应设计并制备了一种在全钒液流电池中应用的基于氰基结构侧链磺化聚芳醚离子交换膜。氰基的存在可以提高聚合物膜的稳定性,支链型磺酸基团可以增强膜的微相分离,从而具有高的离子电导率。此方法制备的基于氰基结构侧链磺化聚芳醚离子交换膜具备优良的电池性能,且具有良好的稳定性。
具体实施方式
以下结合实施案例对本发明做进一步详细的描述,但是本发明的实施方式并不仅限于此。
实施例1
4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈的合成:在250ml三口烧瓶中,将 6ml(46.8mmol)五氟苯甲腈、7.6498g(39mmol)4-羟基苯磺酸钠、和8.0853g (58.85mmol)碳酸钾溶解于溶剂70ml N,N-二甲基甲酰胺中,在在惰性气体保护下0℃保持温度恒定反应24h;将反应溶液离心、萃取、旋蒸、干燥得到白色固体;
得到的4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈如下:
基于氰基结构侧链磺化聚芳醚的合成:在25ml三口烧瓶中,将0.4578g(1.24mmol)4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈、0.2309g(1.24mmol)4, 4-二羟基联苯和0.3428g(2.48mmol)碳酸钾溶解于溶剂5ml二甲基亚砜中在惰性气体保护下30℃保持温度恒定反应40h;将反应溶液倒入沉淀剂乙醇中,过滤、洗涤、干燥得到基于氰基结构侧链磺化聚芳醚;
得到的基于氰基结构侧链磺化聚芳醚如下:
基于氰基结构侧链磺化聚芳醚离子交换膜:取步骤(2)合成的基于氰基结构侧链磺化聚芳醚溶于二甲基亚砜中,制成浓度为32g/L的铸膜液;铸膜液滴加在铸膜玻璃板上,并在烘箱60℃中干燥24h,制成厚度为30μm的基于氰基结构侧链磺化聚芳醚离子交换膜;
经测试表明,基于氰基结构侧链磺化聚芳醚离子交换膜25℃时离子传导率为87.5mS cm-1,吸水率为50.35%,溶胀度为19.6%。在全钒液流电池中,60mA cm-2电密时,CE为94.6%,EE为86.0%;
实施例2
4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈的合成:同实施例1
基于氰基结构侧链磺化聚芳醚的合成:在25ml三口烧瓶中,将0.4578g(1.24mmol)4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈、0.2271g(1.24mmol) 双酚A和0.3428g(2.48mmol)碳酸钾溶解于溶剂5ml二甲基亚砜中在惰性气体保护下30℃保持温度恒定反应40h;将反应溶液倒入沉淀剂乙醇中,过滤、洗涤、干燥得到基于氰基结构侧链磺化聚芳醚;
得到的基于氰基结构侧链磺化聚芳醚如下:
基于氰基结构侧链磺化聚芳醚离子交换膜:取步骤(2)合成的基于氰基结构侧链磺化聚芳醚溶于二甲基亚砜中,制成浓度为32g/L的铸膜液;铸膜液滴加在铸膜玻璃板上,并在烘箱60℃中干燥24h,制成厚度为30μm的基于氰基结构侧链磺化聚芳醚离子交换膜;
经测试表明,基于氰基结构侧链磺化聚芳醚离子交换膜25℃时离子传导率为90.3mS cm-1,吸水率为49.5%,溶胀度为19.4%。在全钒液流电池中,60mA cm-2电密时,CE为95.1%,EE为86.3%;
实施例3
4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈的合成:同实施例1
基于氰基结构侧链磺化聚芳醚的合成:在25ml三口烧瓶中,将0.4578g(1.24mmol)4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈、0.4169g(1.24mmol) 双酚AF和0.3428g(2.48mmol)碳酸钾溶解于溶剂5ml二甲基亚砜中在惰性气体保护下30℃保持温度恒定反应40h;将反应溶液倒入沉淀剂乙醇中,过滤、洗涤、干燥得到基于氰基结构侧链磺化聚芳醚;
得到的基于氰基结构侧链磺化聚芳醚如下:
基于氰基结构侧链磺化聚芳醚离子交换膜:取步骤(2)合成的基于氰基结构侧链磺化聚芳醚溶于二甲基亚砜中,制成浓度为32g/L的铸膜液;铸膜液滴加在铸膜玻璃板上,并在烘箱60℃中干燥24h,制成厚度为30μm的基于氰基结构侧链磺化聚芳醚离子交换膜;
经测试表明,基于氰基结构侧链磺化聚芳醚离子交换膜25℃时离子传导率为88.5mS cm-1,吸水率为48.4%,溶胀度为18.5%。在全钒液流电池中,60mA cm-2电密时,CE为93.9%,EE为84.8%。
Claims (3)
2.权利要求1所述的基于氰基结构侧链磺化聚芳醚离子交换膜的制备方法,其特征在于,步骤如下:
(1)4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈的合成:在惰性气体保护下,将五氟苯甲腈、4-羟基苯磺酸钠和碳酸钾溶解于溶剂N,N-二甲基甲酰胺中,在0℃保持温度恒定反应24h;将反应溶液离心、萃取、旋蒸、干燥得到4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈;
所述的4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈结构式如下:
所述的五氟苯甲腈:4-羟基苯磺酸钠:碳酸钾的摩尔比为1.2:1:1.5;
所述的五氟苯甲腈、4-羟基苯磺酸钠和碳酸钾在溶剂N,N-二甲基甲酰胺中的w/v为10.9%~13.4%;
(2)基于氰基结构侧链磺化聚芳醚的合成:在惰性气体保护下,将4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈、双酚和碳酸钾溶解于溶剂二甲基亚砜中,在30℃保持温度恒定反应40h;将反应溶液倒入沉淀剂A中,过滤、洗涤、干燥得到基于氰基结构侧链磺化聚芳醚;
所述的双酚为4,4-二羟基联苯、双酚A、双酚AF或对苯二酚;
所述的4-苯氧基-4-磺酸基-2,3,5,6-四氟苄腈:4,4-二羟基联苯:碳酸钾的摩尔比为1.:1:1.5;
所述的五氟苯甲腈、4-羟基苯磺酸钠和碳酸钾在溶剂A中的w/v为10.9%~13.4%
所述的沉淀剂A为乙醇、水中的一种;
(3)基于氰基结构侧链磺化聚芳醚离子交换膜:取步骤(2)合成的基于氰基结构侧链磺化聚芳醚溶于溶剂B中,制成浓度为32g/L-37g/L的铸膜液;铸膜液滴加在铸膜玻璃板上,并在烘箱中充分烘干,制成厚度为30μm~40μm的基于氰基结构侧链磺化聚芳醚离子交换膜;
所述的溶剂B为N,N-二甲基乙酰胺、二甲基亚砜中的一种;
所述的铸膜液w/v为3.2~3.7%;
上述的w/v的单位均为g/ml。
3.根据权利要求2所述的制备方法,其特征在于,步骤(3)成膜的烘干温度为40~60℃,时间为24~48小时。
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