CN102964369B - 一类聚合物型硼酸酯锂盐及其制备方法和应用 - Google Patents
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- 239000004327 boric acid Substances 0.000 title claims abstract description 24
- -1 boric acid ester lithium salts Chemical class 0.000 title claims abstract description 24
- 229910003002 lithium salt Inorganic materials 0.000 title claims abstract description 23
- 229920000642 polymer Polymers 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000008346 aqueous phase Substances 0.000 claims abstract description 6
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 6
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 5
- 239000012153 distilled water Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000012074 organic phase Substances 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims abstract 4
- 239000011261 inert gas Substances 0.000 claims abstract 4
- 239000003960 organic solvent Substances 0.000 claims abstract 4
- 239000000843 powder Substances 0.000 claims abstract 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract 2
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000003213 activating effect Effects 0.000 claims abstract 2
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- 239000002245 particle Substances 0.000 claims abstract 2
- 229910000077 silane Inorganic materials 0.000 claims abstract 2
- 238000003756 stirring Methods 0.000 claims abstract 2
- 150000002500 ions Chemical class 0.000 claims description 7
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 4
- 229910001416 lithium ion Inorganic materials 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 229960002645 boric acid Drugs 0.000 description 15
- 235000010338 boric acid Nutrition 0.000 description 15
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RIUNEBYJXQAXKP-UHFFFAOYSA-N [Li+].B([O-])(O)O.C(C(O)C(O)C(=O)O)(=O)O Chemical compound [Li+].B([O-])(O)O.C(C(O)C(O)C(=O)O)(=O)O RIUNEBYJXQAXKP-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- RIUWBIIVUYSTCN-UHFFFAOYSA-N trilithium borate Chemical class [Li+].[Li+].[Li+].[O-]B([O-])[O-] RIUWBIIVUYSTCN-UHFFFAOYSA-N 0.000 description 3
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 2
- 229910001947 lithium oxide Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 238000002444 silanisation Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229910013188 LiBOB Inorganic materials 0.000 description 1
- 229910013872 LiPF Inorganic materials 0.000 description 1
- 229910013870 LiPF 6 Inorganic materials 0.000 description 1
- 101150058243 Lipf gene Proteins 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- DEUISMFZZMAAOJ-UHFFFAOYSA-N lithium dihydrogen borate oxalic acid Chemical compound B([O-])(O)O.C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.[Li+] DEUISMFZZMAAOJ-UHFFFAOYSA-N 0.000 description 1
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920005569 poly(vinylidene fluoride-co-hexafluoropropylene) Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Secondary Cells (AREA)
Abstract
本发明公开了一类聚合物型硼酸酯锂盐及其制备方法和应用。该化合物具有如下结构：其中X1，X2，X3，X4为：R为C1-C5烷基、C1-C5氟代烷基的一种。Y为：直链或带支链的烷基，直链或带支链的氟代烷基，芳基，氟代芳基的至少一种。该类聚合物型硼酸酯锂盐反应可分别采用水相和有机相作为反应介质。工艺过程为：水相——将摩尔比为1∶1的H3BO3和LiOH加入蒸馏水中，惰性气体保护，在搅拌加热状态下慢慢加入配置好的等摩尔比的单体水溶液。反应1h，共沸除水。即得到固体颗粒或粉末，过滤。有机相——将摩尔比为1∶1的LiB(OH)4和硅烷基活化的单体加入有机溶剂中，惰性气体保护，加热搅拌，使有机溶剂回流，反应48h，得到固体粉末或者颗粒，旋转蒸发。将过滤或者旋转蒸发后的产物进行烘干即得到聚合物型硼酸酯锂盐。该聚合物型硼酸酯锂盐可应用于二次锂离子电池，钠硫电池中。
Description
技术领域
本发明涉及一类聚合物型硼酸酯锂盐
本发明涉及一类聚合物型硼酸酯锂盐的制备方法。
本发明涉及二次锂离子电池或其它电池用聚合物电解质等技术领域。
背景技术
现有的二次锂离子电池用商业化电解液多用LiPF6基电解液，但LiPF6制备工艺复杂，成本高，提纯困难，并且其热稳定差，制约了锂离子电池在动力汽车方面的应用。因此，迫切需要开发制备工艺简单，价格低廉，热稳定性高的新型锂盐。硼酸锂盐由于种类繁多且环境友好，近年来越来越引起人们的重视。这类锂盐多以硼为中心原子，与含氧的配体相结合，形成一个大π共轭体系，分散了中心离子的负电荷，是阴离子更加稳定的同时又减小了阴、阳离子的相互吸引力。比较具有代表性的包括双草酸硼酸锂盐(LiBOB)，二氟草酸硼酸锂盐(LiODFB)。基于以上思路，我们合成了聚合物型的硼酸酯锂盐，使其具有更大的阴离子半径，这样可以进一步提高其热稳定性及电解液中阳离子的迁移数。
发明内容
本发明的目的在于合成了一类聚合物型硼酸酯锂盐并提供了合成该类聚合物型硼酸酯锂盐的方法。制备方法包括水相合成和有机相合成两种方法。尤其对于水相合成，该方法无需引发剂，反应条件温和，原料简单，转化率高，非常适合工业化生产。
一类聚合物型硼酸酯锂盐具有如通式1所示的结构：
通式1
其中X1，X2，X3，X4为：
R为C1-C5烷基、C1-C5氟代烷基的一种。
Y为：直链或带支链的烷基，直链或带支链的氟代烷基，芳基，氟代芳基的至少一种。
具体结构式包括如下：
本发明合成的聚合物型硼酸酯锂盐，其制备方法，具体包括水相和有机相两种方法。
本发明合成的聚合物型硼酸酯锂盐，其中所述的金属阳离子不限于锂离子，也可以为钠和钾的离子。
具体实施方式
实施例1水相法合成酒石酸硼酸锂盐
将2.3186g硼酸，1.5735g一水合氢氧化锂和75mL蒸馏水加入250mL三口烧瓶中，通入惰性气体进行保护，不断搅拌溶液。在90～95℃下缓慢滴加已配置好的酒石酸(5.6284g)水(75mL)溶液，滴加完毕后，反应半个小时，加入50mL环己烷，进行共沸除水。待水完全去除后，烧瓶内出现不溶于环己烷的固体，冷却。采用常压过滤得到产物，真空烘箱150℃进行干燥，得到白色固体，此即为聚合物型硼酸酯锂盐——酒石酸硼酸锂盐。
实施例2水相法合成柠檬酸硼酸锂盐
将1.2366g硼酸，0.8392g一水合氢氧化锂和75mL蒸馏水加入250mL三口烧瓶中，通入惰性气体进行保护，不断搅拌溶液。在90～95℃下缓慢滴加已配置好的柠檬酸(3.8428g)水(75mL)溶液，滴加完毕后，反应半个小时，加入50mL环己烷，进行共沸除水。待水完全去除后，烧瓶内出现不溶于环己烷的固体，冷却。采用常压过滤得到产物，真空烘箱150℃进行干燥，得到白色固体，此即为聚合物型硼酸酯锂盐——柠檬酸硼酸锂盐。
实施例3
首先将双三羟甲基丙烷(式1)进行硅烷化(式2)。
式1
式2
将4.2567gLiB(OCH3)4，16.1400g硅烷化的双三羟甲基丙烷和150mL无水乙腈加入三口烧瓶中，通入惰性气体进行保护，不断搅拌溶液。在85℃下反应进行冷凝回流。反应48h后冷却到常温，将含有产物的溶液进行旋转蒸发，得到白色固体。真空烘箱150℃进行干燥，此即为聚合物型硼酸酯锂盐。
实施例4
将2.0000g实施例1的酒石酸硼酸锂盐和2.0000gPVDF-HFP溶于15mL无水的DMF中，溶解，用300μm刮刀刮膜。真空烘箱中150℃烘干，得到厚度为30μm的干态聚合物电解质膜。将干态聚合物膜转移到手套箱中，用PC进行浸泡5min，m(酒石酸硼酸锂盐)∶m(PVDF-HFP)∶m(PC)＝1∶1∶2，得到厚度50μm湿态聚合物电解质膜。以磷酸铁锂做正极，石墨做负极，组装成锂离子电池。
Claims (4)
1.一类聚合物型硼酸酯锂盐具有结构如下：
，，，。
2.权利要求1的聚合物型硼酸酯锂盐，其制备方法，具体包括水相和有机相两种方法；
其中水相方法包括：在水中溶解度较好并且官能团活性较高的单体，工艺过程为：将摩尔比
为1:1的H3BO3和LiOH加入蒸馏水中，惰性气体保护，在搅拌加热状态下慢慢加入配置好的等摩尔比的单体水溶液，反应1h，共沸除水，即得到固体颗粒或粉末，过滤；其中有机相方法包括：在水中溶解度较差，以及反应活性较差的单体，将摩尔比为1:1的LiB(OH)4和硅烷基活化的单体加入有机溶剂中，惰性气体保护，加热搅拌，使有机溶剂回
流，反应48h，得到固体粉末或者颗粒，旋转蒸发，将过滤或者旋转蒸发后的产物进行烘干
即得到聚合物型硼酸酯锂盐。
3.权利要求1的聚合物型硼酸酯锂盐，其中结构式中的锂离子，也可以为钠和钾的离子。
4.权利要求1的聚合物型硼酸酯锂盐，在二次锂离子电池和钠硫电池中的应用。
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| CN104529753B (zh) * | 2014-12-22 | 2016-05-18 | 南通市飞宇精细化学品有限公司 | 一种柠檬酸硼的生产工艺 |
| CN111934006B (zh) * | 2020-07-23 | 2021-09-21 | 深圳技术大学 | 固有微孔聚铝/硼酸盐固态电解质和电池 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998028807A1 (de) * | 1996-12-23 | 1998-07-02 | Dilo Trading Ag | Verfahren und anode zur verbesserung der leistungsdichte von lithiumsekundärbatterien |
| CN1223263A (zh) * | 1997-11-12 | 1999-07-21 | 昭和电工株式会社 | 硼系化合物的制造方法 |
| JP2000173343A (ja) * | 1998-12-02 | 2000-06-23 | Japan Carlit Co Ltd:The | イオン伝導性高分子電解質 |
| US6590009B1 (en) * | 1998-08-11 | 2003-07-08 | Rhodia Chimie | Polymerization and/or crosslinking method under electron beam and/or gamma radiation |
| CN101326189A (zh) * | 2005-10-07 | 2008-12-17 | 凯密特尔有限责任公司 | 硼酸盐、其制备方法和用途 |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998028807A1 (de) * | 1996-12-23 | 1998-07-02 | Dilo Trading Ag | Verfahren und anode zur verbesserung der leistungsdichte von lithiumsekundärbatterien |
| CN1223263A (zh) * | 1997-11-12 | 1999-07-21 | 昭和电工株式会社 | 硼系化合物的制造方法 |
| US6590009B1 (en) * | 1998-08-11 | 2003-07-08 | Rhodia Chimie | Polymerization and/or crosslinking method under electron beam and/or gamma radiation |
| JP2000173343A (ja) * | 1998-12-02 | 2000-06-23 | Japan Carlit Co Ltd:The | イオン伝導性高分子電解質 |
| CN101326189A (zh) * | 2005-10-07 | 2008-12-17 | 凯密特尔有限责任公司 | 硼酸盐、其制备方法和用途 |
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