CN102070661A - 一种高纯草酸二氟硼酸锂的制备方法 - Google Patents
一种高纯草酸二氟硼酸锂的制备方法 Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title abstract description 5
- 229910052744 lithium Inorganic materials 0.000 title abstract description 5
- YNQRWVCLAIUHHI-UHFFFAOYSA-L dilithium;oxalate Chemical compound [Li+].[Li+].[O-]C(=O)C([O-])=O YNQRWVCLAIUHHI-UHFFFAOYSA-L 0.000 claims abstract description 27
- 239000007787 solid Substances 0.000 claims abstract description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000013078 crystal Substances 0.000 claims abstract description 8
- 238000001953 recrystallisation Methods 0.000 claims abstract description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 64
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 26
- 235000006408 oxalic acid Nutrition 0.000 claims description 24
- PSHMSSXLYVAENJ-UHFFFAOYSA-N dilithium;[oxido(oxoboranyloxy)boranyl]oxy-oxoboranyloxyborinate Chemical compound [Li+].[Li+].O=BOB([O-])OB([O-])OB=O PSHMSSXLYVAENJ-UHFFFAOYSA-N 0.000 claims description 23
- 238000004821 distillation Methods 0.000 claims description 16
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000001291 vacuum drying Methods 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000009413 insulation Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- 229910003902 SiCl 4 Inorganic materials 0.000 claims description 4
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- DISYGAAFCMVRKW-UHFFFAOYSA-N butyl ethyl carbonate Chemical compound CCCCOC(=O)OCC DISYGAAFCMVRKW-UHFFFAOYSA-N 0.000 claims description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 claims description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 2
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229910003691 SiBr Inorganic materials 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 claims description 2
- -1 ethylene isopropyl ester Chemical class 0.000 claims description 2
- YYSONLHJONEUMT-UHFFFAOYSA-N pentan-3-yl hydrogen carbonate Chemical compound CCC(CC)OC(O)=O YYSONLHJONEUMT-UHFFFAOYSA-N 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000007086 side reaction Methods 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 7
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 16
- 238000002156 mixing Methods 0.000 description 7
- 229910013188 LiBOB Inorganic materials 0.000 description 5
- 239000008151 electrolyte solution Substances 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 3
- 229910013063 LiBF 4 Inorganic materials 0.000 description 3
- 229910013870 LiPF 6 Inorganic materials 0.000 description 3
- 239000005049 silicon tetrachloride Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 3
- 229910013872 LiPF Inorganic materials 0.000 description 2
- 101150058243 Lipf gene Proteins 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 229910013075 LiBF Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 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
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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Cited By (14)
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---|---|---|---|---|
CN103151561A (zh) * | 2013-03-05 | 2013-06-12 | 华南师范大学 | 一种电解质锂盐及含有该锂盐的电解液制备方法与应用 |
CN103374023A (zh) * | 2012-04-25 | 2013-10-30 | 兰州理工大学 | 草酸二氟硼酸锂和四氟硼酸锂的联产方法 |
CN103382577A (zh) * | 2013-07-29 | 2013-11-06 | 中国科学院青海盐湖研究所 | 一种[(CH3O)2CO]3Li2[C2BF2O4]2单晶及其制备方法与应用 |
CN104230970A (zh) * | 2013-06-21 | 2014-12-24 | 湖南省正源储能材料与器件研究所 | 一种草酸二氟硼酸锂电解质盐的制备方法 |
CN104387411A (zh) * | 2014-11-07 | 2015-03-04 | 周阳 | 一种草酸二氟硼酸锂盐的串联一锅法合成方法 |
CN104628754A (zh) * | 2015-02-01 | 2015-05-20 | 湖南省正源储能材料与器件研究所 | 一种锂离子电池电解质盐草酸二氟硼酸锂(LiODFB)的制备方法 |
CN105399761A (zh) * | 2015-10-22 | 2016-03-16 | 中国海洋石油总公司 | 一种二氟草酸硼酸锂的制备方法 |
WO2016154870A1 (en) | 2015-03-31 | 2016-10-06 | Bayerische Motoren Werke Aktiengesellschaft | Method of making lithium difluoro (oxalato) borate |
CN106749361A (zh) * | 2016-12-07 | 2017-05-31 | 湖南省正源储能材料与器件研究所 | 一种高纯度二氟草酸硼酸锂的高效制备方法 |
CN106946921A (zh) * | 2017-04-07 | 2017-07-14 | 上海如鲲新材料有限公司 | 乙二酸氟硼酯制备二氟草酸硼酸锂与双草酸硼酸锂的方法 |
CN108178726A (zh) * | 2017-12-27 | 2018-06-19 | 江西赣锋锂业股份有限公司 | 一种草酸锂的制备方法 |
CN111978339A (zh) * | 2020-08-20 | 2020-11-24 | 山东森诺威新能源有限公司 | 一种二氟草酸硼酸锂的制备方法 |
CN113968877A (zh) * | 2021-10-29 | 2022-01-25 | 湖南法恩莱特新能源科技有限公司 | 一种二氟草酸硼酸锂的制备方法 |
CN113980045A (zh) * | 2021-12-23 | 2022-01-28 | 江苏华盛锂电材料股份有限公司 | 一种一步法合成二氟草酸硼酸锂的方法 |
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EP1308449A2 (en) * | 2001-11-05 | 2003-05-07 | Central Glass Company, Limited | Process for synthesizing ionic metal complex |
CN101643481A (zh) * | 2009-08-28 | 2010-02-10 | 张家港市国泰华荣化工新材料有限公司 | 一种得到二氟草酸硼酸锂与双草酸硼酸锂的合成工艺 |
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2011
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EP1308449A2 (en) * | 2001-11-05 | 2003-05-07 | Central Glass Company, Limited | Process for synthesizing ionic metal complex |
CN101643481A (zh) * | 2009-08-28 | 2010-02-10 | 张家港市国泰华荣化工新材料有限公司 | 一种得到二氟草酸硼酸锂与双草酸硼酸锂的合成工艺 |
Non-Patent Citations (2)
Title |
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《Electrochemistry Communications》 20061231 S. S. Zhang An unique lithium salt for the improved electrolyte of Li-Ion battery 1423-1428 1-8 第8卷, * |
《电源技术》 20100331 邓凌峰等 锂离子电池电解质LiBC2O4F2的合成与电化学性能 237-240 1-8 第34卷, 第3期 * |
Cited By (17)
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---|---|---|---|---|
CN103374023A (zh) * | 2012-04-25 | 2013-10-30 | 兰州理工大学 | 草酸二氟硼酸锂和四氟硼酸锂的联产方法 |
CN103151561B (zh) * | 2013-03-05 | 2015-07-01 | 华南师范大学 | 一种电解质锂盐及含有该锂盐的电解液制备方法与应用 |
CN103151561A (zh) * | 2013-03-05 | 2013-06-12 | 华南师范大学 | 一种电解质锂盐及含有该锂盐的电解液制备方法与应用 |
CN104230970A (zh) * | 2013-06-21 | 2014-12-24 | 湖南省正源储能材料与器件研究所 | 一种草酸二氟硼酸锂电解质盐的制备方法 |
CN103382577A (zh) * | 2013-07-29 | 2013-11-06 | 中国科学院青海盐湖研究所 | 一种[(CH3O)2CO]3Li2[C2BF2O4]2单晶及其制备方法与应用 |
CN103382577B (zh) * | 2013-07-29 | 2016-04-06 | 中国科学院青海盐湖研究所 | 一种[(CH3O)2CO]3Li2[C2BF2O4]2单晶及其制备方法与应用 |
CN104387411A (zh) * | 2014-11-07 | 2015-03-04 | 周阳 | 一种草酸二氟硼酸锂盐的串联一锅法合成方法 |
CN104387411B (zh) * | 2014-11-07 | 2017-08-25 | 周阳 | 一种草酸二氟硼酸锂盐的串联一锅法合成方法 |
CN104628754A (zh) * | 2015-02-01 | 2015-05-20 | 湖南省正源储能材料与器件研究所 | 一种锂离子电池电解质盐草酸二氟硼酸锂(LiODFB)的制备方法 |
WO2016154870A1 (en) | 2015-03-31 | 2016-10-06 | Bayerische Motoren Werke Aktiengesellschaft | Method of making lithium difluoro (oxalato) borate |
CN105399761A (zh) * | 2015-10-22 | 2016-03-16 | 中国海洋石油总公司 | 一种二氟草酸硼酸锂的制备方法 |
CN106749361A (zh) * | 2016-12-07 | 2017-05-31 | 湖南省正源储能材料与器件研究所 | 一种高纯度二氟草酸硼酸锂的高效制备方法 |
CN106946921A (zh) * | 2017-04-07 | 2017-07-14 | 上海如鲲新材料有限公司 | 乙二酸氟硼酯制备二氟草酸硼酸锂与双草酸硼酸锂的方法 |
CN108178726A (zh) * | 2017-12-27 | 2018-06-19 | 江西赣锋锂业股份有限公司 | 一种草酸锂的制备方法 |
CN111978339A (zh) * | 2020-08-20 | 2020-11-24 | 山东森诺威新能源有限公司 | 一种二氟草酸硼酸锂的制备方法 |
CN113968877A (zh) * | 2021-10-29 | 2022-01-25 | 湖南法恩莱特新能源科技有限公司 | 一种二氟草酸硼酸锂的制备方法 |
CN113980045A (zh) * | 2021-12-23 | 2022-01-28 | 江苏华盛锂电材料股份有限公司 | 一种一步法合成二氟草酸硼酸锂的方法 |
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