JP6046257B2 - トリフルオロメチル基含有環状炭酸エステルの製造方法 - Google Patents
トリフルオロメチル基含有環状炭酸エステルの製造方法 Download PDFInfo
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- JP6046257B2 JP6046257B2 JP2015526854A JP2015526854A JP6046257B2 JP 6046257 B2 JP6046257 B2 JP 6046257B2 JP 2015526854 A JP2015526854 A JP 2015526854A JP 2015526854 A JP2015526854 A JP 2015526854A JP 6046257 B2 JP6046257 B2 JP 6046257B2
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- trifluoromethyl group
- cyclic carbonate
- containing cyclic
- formula
- triphosgene
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title claims description 23
- 150000005676 cyclic carbonates Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 13
- 229910001416 lithium ion Inorganic materials 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 4
- JBTUPCMIRXTEFB-UHFFFAOYSA-N ethenyl trifluoromethyl carbonate Chemical compound FC(F)(F)OC(=O)OC=C JBTUPCMIRXTEFB-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QMASYWGIMXQPEJ-UHFFFAOYSA-N 3,3,3-trifluoropropane-1,2-diol Chemical compound OCC(O)C(F)(F)F QMASYWGIMXQPEJ-UHFFFAOYSA-N 0.000 description 2
- BUQNFEVHFMWPEC-UHFFFAOYSA-N C(O)(O)=O.FC(C(C(C)O)O)(F)F Chemical compound C(O)(O)=O.FC(C(C(C)O)O)(F)F BUQNFEVHFMWPEC-UHFFFAOYSA-N 0.000 description 2
- BJISPRXSOKGLAC-UHFFFAOYSA-N C(O)(O)=O.FC(C(C(CC)O)O)(F)F Chemical compound C(O)(O)=O.FC(C(C(CC)O)O)(F)F BJISPRXSOKGLAC-UHFFFAOYSA-N 0.000 description 2
- NZPWOVXFZLFZCM-UHFFFAOYSA-N C(O)(O)=O.FC(C(CCO)O)(F)F Chemical compound C(O)(O)=O.FC(C(CCO)O)(F)F NZPWOVXFZLFZCM-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JVFRFBXBGRJPBM-UHFFFAOYSA-N 1,1,1-trifluorobutane-2,3-diol Chemical compound CC(O)C(O)C(F)(F)F JVFRFBXBGRJPBM-UHFFFAOYSA-N 0.000 description 1
- XTXWVKJSYMMVQB-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,3-diol Chemical compound CCC(O)C(O)C(F)(F)F XTXWVKJSYMMVQB-UHFFFAOYSA-N 0.000 description 1
- SCLIIHMYYAHRGK-UHFFFAOYSA-N 4,4,4-trifluorobutane-1,3-diol Chemical compound OCCC(O)C(F)(F)F SCLIIHMYYAHRGK-UHFFFAOYSA-N 0.000 description 1
- HDNHNLSKEVEZRY-UHFFFAOYSA-N CCC(C(C(F)(F)F)O1)OC1=O Chemical compound CCC(C(C(F)(F)F)O1)OC1=O HDNHNLSKEVEZRY-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/02—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2
- C07D317/04—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- 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)
- Organic Chemistry (AREA)
- Secondary Cells (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
リチウムイオン電池は、エネルギー密度が高い、出力電圧が高い、サイクル寿命が長い、記憶効果がなく、環境汚染が小さいなどの利点があるため、最も注目されて潜在的発展性を有する二次電池である。現在、リチウムイオン電池の電解液で使用される溶媒は、通常、炭酸エステル類で、このような溶媒は、リチウムイオン電池の充放電容量とサイクル寿命を向上させることができる。しかし、これらの溶媒は、引火点が低いために、近年、リチウムイオン電池による火災または爆発に関する報道がよく見られる。リチウムイオン電池の安全性問題が注目され、リチウムイオン電池の高エネルギー化、大型化への発展を制限するネックにもなっている。例えば、線形炭酸エステルなどの燃えやすい有機溶媒を使用するのは、リチウムイオン電池による火災または爆発の主な原因の一つである。
最近の研究によって、トリフルオロメチル基含有環状炭酸エステルを溶媒とすると、よりよくSEI膜を形成することができ、有効に溶媒のさらなる分解を阻止し、且つリチウムイオン電池の安全性を向上させ、リチウムイオン電池のサイクル寿命を延ばすことが見出されてきた。
前記酸結合剤とトリホスゲンのモル比は6〜10:1である。
酸結合剤は、トリエチルアミン、ジエチルアミン、エチレンジアミン、ジプロピルアミン、トリプロピルアミン、プロピレンジアミン、n−ブチルアミン、ピリジンから選ばれる一種または複数種の物質である。
前記酸結合剤とトリホスゲンのモル比は6〜8:1であることが好ましい。
1)劇毒のホスゲンを反応原料としないため、工業化生産が容易である。
2)収率が高く、製品の純度が99.9%超であるため、リチウムイオン電池の電解液に使用されるときの要求を満足する。
実施例1
実施例2
実施例3
実施例4
実施例5
Claims (4)
- トリフルオロメチル基含有飽和二価アルコールとトリホスゲンをモル比3〜10:1で反応釜に入れ、撹拌しながら酸結合剤を滴下し、反応釜内の温度を0℃〜80℃とし、撹拌しながら1〜12時間反応させ、得られたトリフルオロメチル基含有環状炭酸エステルを減圧下で精密蒸留し、トリフルオロメチル基含有環状炭酸エステルを得る工程を有するトリフルオロメチル基含有環状炭酸エステルの製造方法であって、
前記酸結合剤と前記トリホスゲンのモル比は6〜10:1であり、
前記反応は溶媒非存在下で行うことを特徴とするトリフルオロメチル基含有環状炭酸エステルの製造方法。 - 前記酸結合剤は、トリエチルアミン、ジエチルアミン、エチレンジアミン、ジプロピルアミン、トリプロピルアミン、プロピレンジアミン、n−ブチルアミン、ピリジンから選ばれる一種または複数種の物質であることを特徴とする請求項1に記載のトリフルオロメチル基含有環状炭酸エステルの製造方法。
- 前記酸結合剤と前記トリホスゲンの好適なモル比は6〜8:1であることを特徴とする請求項1に記載のトリフルオロメチル基含有環状炭酸エステルの製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201210286320.9 | 2012-08-13 | ||
CN2012102863209A CN102807549A (zh) | 2012-08-13 | 2012-08-13 | 一种三氟甲基环状碳酸酯的制备方法 |
PCT/CN2012/083398 WO2014026432A1 (zh) | 2012-08-13 | 2012-10-24 | 一种三氟甲基环状碳酸酯的制备方法 |
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JP2015531761A JP2015531761A (ja) | 2015-11-05 |
JP6046257B2 true JP6046257B2 (ja) | 2016-12-14 |
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JP (1) | JP6046257B2 (ja) |
KR (1) | KR101691522B1 (ja) |
CN (1) | CN102807549A (ja) |
WO (1) | WO2014026432A1 (ja) |
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CN113620923B (zh) * | 2021-07-16 | 2023-03-14 | 扬州工业职业技术学院 | 一种低温电解液添加剂的制备方法及应用 |
CN115433154B (zh) * | 2022-11-08 | 2023-04-11 | 江苏华盛锂电材料股份有限公司 | 一种亚甲基碳酸乙烯酯的制备方法 |
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CA2087390A1 (en) * | 1992-02-12 | 1993-08-13 | Jack E. Richman | Preparation of fluorinated functional compounds |
JPH08287950A (ja) * | 1995-04-18 | 1996-11-01 | Sumitomo Chem Co Ltd | 非水電解液とこれを用いたリチウム二次電池 |
JP2008150418A (ja) | 2006-12-14 | 2008-07-03 | Dic Corp | ポリエステルポリオールの精製方法 |
JP2008192504A (ja) | 2007-02-06 | 2008-08-21 | Daikin Ind Ltd | 非水系電解液 |
JP5082520B2 (ja) * | 2007-03-16 | 2012-11-28 | ダイキン工業株式会社 | 含フッ素ジオール化合物の製造方法 |
CN101279987A (zh) * | 2007-04-05 | 2008-10-08 | 江西麒麟化工有限公司 | 泰诺福韦生产工艺 |
CN100558721C (zh) * | 2007-06-01 | 2009-11-11 | 张家港市华盛化学有限公司 | 氟代环状碳酸酯的制备方法 |
ES2494854T3 (es) * | 2007-12-03 | 2014-09-16 | Asahi Glass Company, Limited | Método para la producción de un compuesto de carbonato |
JP2010262801A (ja) * | 2009-05-01 | 2010-11-18 | Sony Corp | 二次電池および電解質 |
TW201105646A (en) * | 2009-05-28 | 2011-02-16 | Solvay Fluor Gmbh | Process for the preparation of 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones |
JP5321685B2 (ja) * | 2009-09-18 | 2013-10-23 | ダイキン工業株式会社 | リチウム二次電池の非水電解液用溶媒 |
WO2012067248A1 (ja) * | 2010-11-19 | 2012-05-24 | 三菱化学株式会社 | 4-アルキニル-1,3-ジオキソラン-2-オン誘導体の製造法 |
-
2012
- 2012-08-13 CN CN2012102863209A patent/CN102807549A/zh active Pending
- 2012-10-24 WO PCT/CN2012/083398 patent/WO2014026432A1/zh active Application Filing
- 2012-10-24 JP JP2015526854A patent/JP6046257B2/ja active Active
- 2012-10-24 KR KR1020157003410A patent/KR101691522B1/ko active IP Right Grant
Also Published As
Publication number | Publication date |
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CN102807549A (zh) | 2012-12-05 |
KR20150034771A (ko) | 2015-04-03 |
WO2014026432A1 (zh) | 2014-02-20 |
KR101691522B1 (ko) | 2016-12-30 |
JP2015531761A (ja) | 2015-11-05 |
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