CN103688326A - 双中心季铵盐离子液体及其制备方法和应用 - Google Patents
双中心季铵盐离子液体及其制备方法和应用 Download PDFInfo
- Publication number
- CN103688326A CN103688326A CN201180072283.5A CN201180072283A CN103688326A CN 103688326 A CN103688326 A CN 103688326A CN 201180072283 A CN201180072283 A CN 201180072283A CN 103688326 A CN103688326 A CN 103688326A
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- ammonium salt
- double
- center quaternary
- salt ionic
- 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.)
- Pending
Links
- -1 quaternary ammonium salt ion Chemical class 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 19
- 239000007788 liquid Substances 0.000 title description 16
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 94
- 239000002608 ionic liquid Substances 0.000 claims abstract description 70
- 239000003792 electrolyte Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
- 229910003002 lithium salt Inorganic materials 0.000 claims description 49
- 159000000002 lithium salts Chemical class 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 238000003756 stirring Methods 0.000 claims description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 32
- 239000003960 organic solvent Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000001816 cooling Methods 0.000 claims description 12
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 11
- 239000008346 aqueous phase Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 11
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 11
- 150000002466 imines Chemical class 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052744 lithium Inorganic materials 0.000 claims description 10
- 238000001291 vacuum drying Methods 0.000 claims description 10
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- BNFMNDYWEVGUMM-UHFFFAOYSA-N [chloro(methoxy)methoxy]ethane Chemical group CCOC(Cl)OC BNFMNDYWEVGUMM-UHFFFAOYSA-N 0.000 claims description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 150000001350 alkyl halides Chemical class 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000005342 ion exchange Methods 0.000 claims description 7
- KQEKZVSGPGHHLH-UHFFFAOYSA-N [bromo(methoxy)methoxy]ethane Chemical compound CCOC(Br)OC KQEKZVSGPGHHLH-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000004448 titration Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 241001468684 Diplocardia Species 0.000 claims description 2
- 239000002027 dichloromethane extract Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 229910005143 FSO2 Inorganic materials 0.000 abstract 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 16
- 238000000605 extraction Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 239000003643 water by type Substances 0.000 description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 14
- 239000012046 mixed solvent Substances 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 239000005486 organic electrolyte Substances 0.000 description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 description 5
- 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 5
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- 229910001290 LiPF6 Inorganic materials 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000255964 Pieridae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 239000002001 electrolyte material Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KVFIZLDWRFTUEM-UHFFFAOYSA-N potassium;bis(trifluoromethylsulfonyl)azanide Chemical compound [K+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F KVFIZLDWRFTUEM-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/035—Liquid electrolytes, e.g. impregnating materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/60—Liquid electrolytes characterised by the solvent
-
- 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
-
- 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
- Y02E60/13—Energy storage using capacitors
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Secondary Cells (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
PCT国内申请,说明书已公开。
Claims (1)
- PCT国内申请,权利要求书已公开。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2011/079107 WO2013029236A1 (zh) | 2011-08-30 | 2011-08-30 | 双中心季铵盐离子液体及其制备方法和应用 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN103688326A true CN103688326A (zh) | 2014-03-26 |
Family
ID=47755195
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201180072283.5A Pending CN103688326A (zh) | 2011-08-30 | 2011-08-30 | 双中心季铵盐离子液体及其制备方法和应用 |
Country Status (5)
Country | Link |
---|---|
US (1) | US9202632B2 (zh) |
EP (1) | EP2752861A4 (zh) |
JP (1) | JP5667328B2 (zh) |
CN (1) | CN103688326A (zh) |
WO (1) | WO2013029236A1 (zh) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016084792A1 (ja) * | 2014-11-28 | 2016-06-02 | カーリットホールディングス株式会社 | イオン液体、その製造方法及びその用途 |
CN105032484A (zh) * | 2015-06-24 | 2015-11-11 | 南京大学 | 一类双中心离子液体结构的固体酸催化剂及其制法和用途 |
TW201708206A (zh) * | 2015-07-22 | 2017-03-01 | 國立大學法人東京大學 | 非水系電解液 |
CN109478472B (zh) * | 2016-07-29 | 2022-02-22 | 大塚化学株式会社 | 电化学设备用电解质、电解液以及电化学设备 |
JP2018035121A (ja) * | 2016-09-02 | 2018-03-08 | 東ソー株式会社 | カチオン性ジェミニ型界面活性剤 |
TW201936564A (zh) * | 2017-11-21 | 2019-09-16 | 日商日東電工股份有限公司 | 離子化合物及包含其之組合物 |
EP3714017A2 (en) | 2017-11-21 | 2020-09-30 | Nitto Denko Corporation | Basic ionic liquids compositions and elements including the same |
WO2019113513A1 (en) | 2017-12-08 | 2019-06-13 | Baker Hughes, A Ge Company, Llc | Ionic liquid based well asphaltene inhibitors and methods of using the same |
EA202091413A1 (ru) | 2018-07-11 | 2020-09-24 | Бейкер Хьюз Холдингз Ллк | Скважинные ингибиторы асфальтенов на основе ионной жидкости и способы их применения |
CN114835573B (zh) * | 2021-02-01 | 2023-04-18 | 中国科学院化学研究所 | 一种合成羧酸盐类化合物的方法 |
JP7253098B2 (ja) * | 2021-09-02 | 2023-04-05 | 住友化学株式会社 | イオン液体及び複合電解質 |
WO2023033162A1 (ja) * | 2021-09-02 | 2023-03-09 | 住友化学株式会社 | イオン液体及び複合電解質 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002151360A (ja) * | 2000-11-08 | 2002-05-24 | Kuraray Co Ltd | 電気二重層キャパシタ |
CN101271989A (zh) * | 2008-04-30 | 2008-09-24 | 深圳新宙邦科技股份有限公司 | 锂离子电池室温离子液体电解质及其制备方法 |
CN102060715A (zh) * | 2010-12-22 | 2011-05-18 | 南京大学 | 双季铵羧酸盐功能化离子液体及其制法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4721512A (en) * | 1985-11-25 | 1988-01-26 | Ciba-Geigy Corporation | Process for aftertreating dyed cellulosic material |
EP0258923B1 (en) * | 1986-09-02 | 1993-10-06 | Akzo Nobel N.V. | Fabric softening composition and detergent-composition comprising the same |
US5130177A (en) * | 1990-02-01 | 1992-07-14 | Xerox Corporation | Conductive coating compositions |
GB9211760D0 (en) * | 1992-06-03 | 1992-07-15 | Gillette Co | Correction fluids |
US7476393B2 (en) * | 2002-11-29 | 2009-01-13 | L'oreal | Process for the preparation of a cationic nanoemulsion, and cosmetic composition |
JP2005104845A (ja) * | 2003-09-26 | 2005-04-21 | Tosoh Corp | 4級アンモニウム系常温溶融塩及び製造法 |
CN101228602A (zh) | 2005-07-29 | 2008-07-23 | 广荣化学工业株式会社 | 电化学元件 |
CN101962318A (zh) * | 2009-07-24 | 2011-02-02 | 中国科学院兰州化学物理研究所 | 哑铃型离子液体催化合成聚甲氧基二甲醚的方法 |
CN102020630A (zh) * | 2009-09-11 | 2011-04-20 | 中国科学院兰州化学物理研究所 | 双功能化离子液体催化甲醛环化反应合成三聚甲醛的方法 |
-
2011
- 2011-08-30 US US14/234,378 patent/US9202632B2/en not_active Expired - Fee Related
- 2011-08-30 EP EP11871719.8A patent/EP2752861A4/en not_active Withdrawn
- 2011-08-30 WO PCT/CN2011/079107 patent/WO2013029236A1/zh active Application Filing
- 2011-08-30 JP JP2014527453A patent/JP5667328B2/ja active Active
- 2011-08-30 CN CN201180072283.5A patent/CN103688326A/zh active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002151360A (ja) * | 2000-11-08 | 2002-05-24 | Kuraray Co Ltd | 電気二重層キャパシタ |
CN101271989A (zh) * | 2008-04-30 | 2008-09-24 | 深圳新宙邦科技股份有限公司 | 锂离子电池室温离子液体电解质及其制备方法 |
CN102060715A (zh) * | 2010-12-22 | 2011-05-18 | 南京大学 | 双季铵羧酸盐功能化离子液体及其制法 |
Non-Patent Citations (2)
Title |
---|
李永路等: "新型温控聚醚离子液体的合成及应用", 《中国科技论文在线》 * |
章正熙: "新型离子液体电解液的设计与开发及在锂二次电池中的应用研究", 《中国博士学位论文全文数据库 工程科技II辑》 * |
Also Published As
Publication number | Publication date |
---|---|
EP2752861A1 (en) | 2014-07-09 |
EP2752861A4 (en) | 2015-04-01 |
JP5667328B2 (ja) | 2015-02-12 |
US9202632B2 (en) | 2015-12-01 |
US20140158928A1 (en) | 2014-06-12 |
JP2014531415A (ja) | 2014-11-27 |
WO2013029236A1 (zh) | 2013-03-07 |
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