CN104072533A - 一类含低聚氧化乙烯单元的硅腈类化合物及其制备方法、在锂电池中的应用 - Google Patents
一类含低聚氧化乙烯单元的硅腈类化合物及其制备方法、在锂电池中的应用 Download PDFInfo
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- CN104072533A CN104072533A CN201410256272.8A CN201410256272A CN104072533A CN 104072533 A CN104072533 A CN 104072533A CN 201410256272 A CN201410256272 A CN 201410256272A CN 104072533 A CN104072533 A CN 104072533A
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- Prior art keywords
- nitrile compounds
- low polyoxyethylene
- silicon
- silicon nitrile
- polyoxyethylene glycol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 polyoxyethylene units Polymers 0.000 title claims abstract description 77
- 229910052744 lithium Inorganic materials 0.000 title claims abstract description 31
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 34
- 239000010703 silicon Substances 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 13
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 13
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 239000003792 electrolyte Substances 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000013067 intermediate product Substances 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 3
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- 230000007935 neutral effect Effects 0.000 claims description 2
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- 150000001875 compounds Chemical class 0.000 abstract description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 7
- 239000002001 electrolyte material Substances 0.000 abstract description 6
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- 238000007254 oxidation reaction Methods 0.000 abstract description 5
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- 150000003839 salts Chemical class 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- SIXOAUAWLZKQKX-UHFFFAOYSA-N carbonic acid;prop-1-ene Chemical compound CC=C.OC(O)=O SIXOAUAWLZKQKX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002210 silicon-based material Substances 0.000 abstract 1
- 239000008151 electrolyte solution Substances 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 13
- 229910001416 lithium ion Inorganic materials 0.000 description 13
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 12
- 229910002804 graphite Inorganic materials 0.000 description 9
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- 238000007599 discharging Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 7
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000006258 conductive agent Substances 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- 239000006183 anode active material Substances 0.000 description 5
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- 238000001228 spectrum Methods 0.000 description 5
- SNJNVEVAILOJBB-UHFFFAOYSA-N 2-ethoxypropanenitrile Chemical compound CCOC(C)C#N SNJNVEVAILOJBB-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
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- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910003002 lithium salt Inorganic materials 0.000 description 4
- 159000000002 lithium salts Chemical class 0.000 description 4
- 239000007773 negative electrode material Substances 0.000 description 4
- 230000005311 nuclear magnetism Effects 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- 230000008901 benefit Effects 0.000 description 3
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910013716 LiNi Inorganic materials 0.000 description 2
- 229910013870 LiPF 6 Inorganic materials 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
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- 238000010494 dissociation reaction Methods 0.000 description 2
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- 238000003475 lamination Methods 0.000 description 2
- 238000004502 linear sweep voltammetry Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical class CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- 229910013063 LiBF 4 Inorganic materials 0.000 description 1
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- 229910015645 LiMn Inorganic materials 0.000 description 1
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- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- JDZCKJOXGCMJGS-UHFFFAOYSA-N [Li].[S] Chemical compound [Li].[S] JDZCKJOXGCMJGS-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical class CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical class COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920005609 vinylidenefluoride/hexafluoropropylene copolymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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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CN201410256272.8A CN104072533B (zh) | 2014-06-10 | 2014-06-10 | 一类含低聚氧化乙烯单元的硅腈类化合物及其制备方法、在锂电池中的应用 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016054493A1 (en) | 2014-10-02 | 2016-04-07 | Silatronix, Inc. | Organosilicon-containing electrolyte compositions having enhanced electrochemical and thermal stability |
WO2019101489A1 (en) | 2017-11-21 | 2019-05-31 | Jennewein Biotechnologie Gmbh | Process for the purification of a sialic acid from a fermentation broth |
CN111883844A (zh) * | 2020-07-24 | 2020-11-03 | 香河昆仑化学制品有限公司 | 一种含有机硅化合物的电解液以及电池负极和电化学储能器件 |
CN112271336A (zh) * | 2020-11-25 | 2021-01-26 | 广州天赐高新材料股份有限公司 | 一种电解液及锂二次电池 |
CN112290088A (zh) * | 2019-07-23 | 2021-01-29 | 张家港市国泰华荣化工新材料有限公司 | 一种非水电解液及锂离子电池 |
CN114122400A (zh) * | 2021-11-03 | 2022-03-01 | 珠海冠宇电池股份有限公司 | 一种负极极片及含该负极极片的锂离子电池 |
CN116742116A (zh) * | 2023-08-16 | 2023-09-12 | 蜂巢能源科技股份有限公司 | 一种凝胶电解质及其制备方法和锂离子电池 |
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CN1656252A (zh) * | 2002-05-29 | 2005-08-17 | 电化学工业有限公司(国际) | 制造有机官能硅烷的电化学方法 |
CN101859913A (zh) * | 2010-05-19 | 2010-10-13 | 中国科学院广州能源研究所 | 含氰基高介电常数有机硅电解质材料 |
CN102074736A (zh) * | 2010-06-07 | 2011-05-25 | 中国科学院广州能源研究所 | 含聚醚链有机硅胺电解质材料及其在锂电池电解液中的应用 |
CN102924495A (zh) * | 2012-10-15 | 2013-02-13 | 中国科学院广州能源研究所 | 含聚醚链有机卤硅烷及其在非水系锂离子电池电解液中的应用 |
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2014
- 2014-06-10 CN CN201410256272.8A patent/CN104072533B/zh active Active
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CN1656252A (zh) * | 2002-05-29 | 2005-08-17 | 电化学工业有限公司(国际) | 制造有机官能硅烷的电化学方法 |
CN101859913A (zh) * | 2010-05-19 | 2010-10-13 | 中国科学院广州能源研究所 | 含氰基高介电常数有机硅电解质材料 |
CN102074736A (zh) * | 2010-06-07 | 2011-05-25 | 中国科学院广州能源研究所 | 含聚醚链有机硅胺电解质材料及其在锂电池电解液中的应用 |
CN102924495A (zh) * | 2012-10-15 | 2013-02-13 | 中国科学院广州能源研究所 | 含聚醚链有机卤硅烷及其在非水系锂离子电池电解液中的应用 |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102185154B1 (ko) * | 2014-10-02 | 2020-12-01 | 실라트로닉스, 인크. | 향상된 전기화학적 및 열적 안정성을 갖는 유기규소-함유 전해질 조성물 |
US9680185B2 (en) | 2014-10-02 | 2017-06-13 | Silatronix, Inc. | Organosilicon-containing electrolyte compositions having enhanced electrochemical and thermal stability |
WO2016054493A1 (en) | 2014-10-02 | 2016-04-07 | Silatronix, Inc. | Organosilicon-containing electrolyte compositions having enhanced electrochemical and thermal stability |
CN107004902A (zh) * | 2014-10-02 | 2017-08-01 | 塞勒创尼克斯公司 | 具有增强的电化学和热稳定性的含有机硅的电解液组合物 |
US9799918B2 (en) | 2014-10-02 | 2017-10-24 | Silatronix, Inc. | Organosilicon—containing electrolyte compositions having enhanced electrochemical and thermal stability |
KR20170063639A (ko) * | 2014-10-02 | 2017-06-08 | 실라트로닉스, 인크. | 향상된 전기화학적 및 열적 안정성을 갖는 유기규소-함유 전해질 조성물 |
US10790536B2 (en) | 2014-10-02 | 2020-09-29 | Silatronix, Inc. | Organosilicon-containing electrolyte compositions having enhanced electrochemical and thermal stability |
WO2019101489A1 (en) | 2017-11-21 | 2019-05-31 | Jennewein Biotechnologie Gmbh | Process for the purification of a sialic acid from a fermentation broth |
US11834691B2 (en) | 2017-11-21 | 2023-12-05 | Chr. Hansen HMO GmbH | Process for purification of a sialic acid from a fermentation broth |
CN112290088A (zh) * | 2019-07-23 | 2021-01-29 | 张家港市国泰华荣化工新材料有限公司 | 一种非水电解液及锂离子电池 |
CN111883844A (zh) * | 2020-07-24 | 2020-11-03 | 香河昆仑化学制品有限公司 | 一种含有机硅化合物的电解液以及电池负极和电化学储能器件 |
CN112271336A (zh) * | 2020-11-25 | 2021-01-26 | 广州天赐高新材料股份有限公司 | 一种电解液及锂二次电池 |
CN112271336B (zh) * | 2020-11-25 | 2021-08-27 | 广州天赐高新材料股份有限公司 | 一种电解液及锂二次电池 |
CN114122400A (zh) * | 2021-11-03 | 2022-03-01 | 珠海冠宇电池股份有限公司 | 一种负极极片及含该负极极片的锂离子电池 |
CN114122400B (zh) * | 2021-11-03 | 2024-05-28 | 珠海冠宇电池股份有限公司 | 一种负极极片及含该负极极片的锂离子电池 |
CN116742116A (zh) * | 2023-08-16 | 2023-09-12 | 蜂巢能源科技股份有限公司 | 一种凝胶电解质及其制备方法和锂离子电池 |
CN116742116B (zh) * | 2023-08-16 | 2023-11-03 | 蜂巢能源科技股份有限公司 | 一种凝胶电解质及其制备方法和锂离子电池 |
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