CN102952092B - 唑烷类离子液体及其制备方法和应用 - Google Patents
唑烷类离子液体及其制备方法和应用 Download PDFInfo
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- CN102952092B CN102952092B CN201110253190.4A CN201110253190A CN102952092B CN 102952092 B CN102952092 B CN 102952092B CN 201110253190 A CN201110253190 A CN 201110253190A CN 102952092 B CN102952092 B CN 102952092B
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- Prior art keywords
- oxazolidine
- ionic liquid
- organic solvent
- lithium
- lithium salt
- 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.)
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 73
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000003792 electrolyte Substances 0.000 claims abstract description 23
- 229910003002 lithium salt Inorganic materials 0.000 claims description 42
- 159000000002 lithium salts Chemical class 0.000 claims description 42
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 39
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- -1 alkyl oxazolidine halide Chemical class 0.000 claims description 33
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 30
- 239000003960 organic solvent Substances 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 150000004820 halides Chemical class 0.000 claims description 15
- 239000008367 deionised water Substances 0.000 claims description 12
- 229910021641 deionized water Inorganic materials 0.000 claims description 12
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001350 alkyl halides Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 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
- 239000008151 electrolyte solution Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910003473 lithium bis(trifluoromethanesulfonyl)imide Inorganic materials 0.000 claims description 8
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000005342 ion exchange Methods 0.000 claims description 7
- 150000002917 oxazolidines Chemical class 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- QNANOJUKEFSKKT-UHFFFAOYSA-N 1-(bromomethoxy)-2-methoxyethane Chemical compound COCCOCBr QNANOJUKEFSKKT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical group COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 claims description 4
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000002027 dichloromethane extract Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 101710134784 Agnoprotein Proteins 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910005143 FSO2 Inorganic materials 0.000 abstract 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 14
- 239000012046 mixed solvent Substances 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000005486 organic electrolyte Substances 0.000 description 8
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 7
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical class [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 229910013063 LiBF 4 Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910013870 LiPF 6 Inorganic materials 0.000 description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 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 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- CBPHUQIHJKGXHY-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrochloride Chemical compound Cl.COCCOC CBPHUQIHJKGXHY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021135 KPF6 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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CN201110253190.4A CN102952092B (zh) | 2011-08-30 | 2011-08-30 | 唑烷类离子液体及其制备方法和应用 |
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CN201110253190.4A CN102952092B (zh) | 2011-08-30 | 2011-08-30 | 唑烷类离子液体及其制备方法和应用 |
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CN102952092A CN102952092A (zh) | 2013-03-06 |
CN102952092B true CN102952092B (zh) | 2014-11-05 |
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Families Citing this family (1)
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CN103819668A (zh) * | 2014-01-16 | 2014-05-28 | 昆山京昆油田化学科技开发公司 | 一种离子液体聚合物的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060210876A1 (en) * | 2005-03-17 | 2006-09-21 | Takashi Kuboki | Electrochemical device |
CN1950338A (zh) * | 2004-03-05 | 2007-04-18 | 霍尼韦尔国际公司 | 杂环胺的离子液体 |
CN101085762A (zh) * | 2007-07-05 | 2007-12-12 | 上海交通大学 | 一种含n-腈基烷基-n-烷基吗啉阳离子的离子液体及其制备方法 |
CN102015666A (zh) * | 2008-04-29 | 2011-04-13 | 默克专利有限公司 | 反应性离子液体 |
-
2011
- 2011-08-30 CN CN201110253190.4A patent/CN102952092B/zh not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1950338A (zh) * | 2004-03-05 | 2007-04-18 | 霍尼韦尔国际公司 | 杂环胺的离子液体 |
US20060210876A1 (en) * | 2005-03-17 | 2006-09-21 | Takashi Kuboki | Electrochemical device |
CN101085762A (zh) * | 2007-07-05 | 2007-12-12 | 上海交通大学 | 一种含n-腈基烷基-n-烷基吗啉阳离子的离子液体及其制备方法 |
CN102015666A (zh) * | 2008-04-29 | 2011-04-13 | 默克专利有限公司 | 反应性离子液体 |
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Effective date of registration: 20151210 Address after: 523000, Dongguan City, Guangdong Province town of solid soil Jinqiao village Jinqiao Industrial Zone, Dongguan City Long Electronic Co., Ltd. Patentee after: DONGGUAN JIUZHI ELECTRONIC Co.,Ltd. Address before: 518109 Guangdong province Shenzhen city Longhua District Office of Longsheng big wave gold dragon road community e-commerce incubator business exhibition Tao Plaza A block 295-2 Patentee before: Shenzhen Qichuangmei Technology Co.,Ltd. Effective date of registration: 20151210 Address after: 518109 Guangdong province Shenzhen city Longhua District Office of Longsheng big wave gold dragon road community e-commerce incubator business exhibition Tao Plaza A block 295-2 Patentee after: Shenzhen Qichuangmei Technology Co.,Ltd. Address before: 518100, Guangdong Province, Shenzhen, Nanshan District Nanhai Road, sea king building, block A, 22 floor Patentee before: OCEAN'S KING LIGHTING SCIENCE & TECHNOLOGY Co.,Ltd. Patentee before: Shenzhen Haiyangwang Illumination Technology Co.,Ltd. |
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CB03 | Change of inventor or designer information |
Inventor after: Cheng Jiawei Inventor after: Ping Xine Inventor after: Wang Guoquan Inventor before: Zhou Mingjie Inventor before: Liu Daxi Inventor before: Wang Yaobing |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20141105 Termination date: 20170830 |
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CF01 | Termination of patent right due to non-payment of annual fee |