WO2014026432A1 - Procédé pour préparer un carbonate cyclique de trifluorométhyle - Google Patents

Procédé pour préparer un carbonate cyclique de trifluorométhyle Download PDF

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Publication number
WO2014026432A1
WO2014026432A1 PCT/CN2012/083398 CN2012083398W WO2014026432A1 WO 2014026432 A1 WO2014026432 A1 WO 2014026432A1 CN 2012083398 W CN2012083398 W CN 2012083398W WO 2014026432 A1 WO2014026432 A1 WO 2014026432A1
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WO
WIPO (PCT)
Prior art keywords
trifluoromethyl
cyclic carbonate
triphosgene
reaction
stirring
Prior art date
Application number
PCT/CN2012/083398
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English (en)
Chinese (zh)
Inventor
张先林
杨志勇
陆海媛
吴国栋
周立新
Original Assignee
江苏华盛精化工股份有限公司
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 江苏华盛精化工股份有限公司 filed Critical 江苏华盛精化工股份有限公司
Priority to JP2015526854A priority Critical patent/JP6046257B2/ja
Priority to KR1020157003410A priority patent/KR101691522B1/ko
Publication of WO2014026432A1 publication Critical patent/WO2014026432A1/fr

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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

Definitions

  • the present invention relates to a process for preparing a trifluoromethyl cyclic carbonate suitable for use in the field of lithium ion battery electrolytes.
  • Lithium-ion batteries have the advantages of high energy density, high output voltage, long cycle life, no memory effect, and low environmental pollution. They are the most attractive and promising secondary batteries.
  • the solvent used for the lithium ion battery electrolyte is usually a carbonate type, which can improve the charge and discharge capacity and cycle life of the lithium ion battery, but their flash point is low, and in recent years, the fire caused by the lithium ion battery Even the reports of the explosion are not uncommon. The safety of lithium-ion batteries has received widespread attention.
  • Fluorinated solvents generally have a high flash point or even no flash point, so the use of a fluorinated solvent is beneficial to improve the safety of lithium ion batteries.
  • Fluorinated cyclic carbonate compounds have the advantages of stable physicochemical properties, high dielectric constant and flash point, good compatibility with electrolyte salts and other organic solvents, and are the preferred alternatives for lithium ion battery electrolyte solvents.
  • the preparation method comprises the following steps: adding a trifluoromethyl saturated diol to a triphosole ratio of 1:3 to 10, adding to the reaction kettle, adding an acid binding agent under stirring, and adjusting the temperature in the reaction vessel by 0°. C ⁇ 80 ° C, stirring reaction l ⁇ 12h, to obtain a trifluoromethyl cyclic carbonate, by distillation under reduced pressure, to obtain a trifluoromethyl cyclic carbonate (purity of 99.9% or more);
  • the molar ratio of the acid binding agent to the triphosgene is 6-10:1; the trifluoromethyl saturation
  • n 0 or 1.
  • the acid binding agent is selected from one or more of the following: triethylamine, diethylamine, ethylenediamine- Amine, tripropylamine, propylenediamine, n-butylamine, pyridine.
  • the acid binding agent and The invention has the following advantages:
  • the chromatographic conditions were Agilent 7890A, split ratio 50: 1, inlet temperature 280 °C, detector temperature 300 °C, column HP-5 (30m X 0.25m X 0.25 ⁇ m), temperature program 100 °C (2min) - 10 °C /min-250 °C (2min) - 15 °C /min-280 °C (5min), standard calibration retention time, area normalization method.
  • Example 1 To a 1000 mL three-necked flask, 384 g (3 mol) of trifluoropropanediol and 297 g (lmol) of triphosgene were added, and 606 g (6 mol) of triethylamine was added dropwise thereto with stirring in an ice water bath at 0 ° C, and the mixture was filtered for 12 hours, and the filtrate was depressurized. The lower distillation was carried out, and 304 g of 85-88 ° C / 15 mmHg fraction was collected.
  • the collected fraction was detected by gas chromatography Agilent 7890A (RT 3.685 ), and the purity of the trifluoromethyl ethylene carbonate in the fraction was 99.94 Wt.%. The yield of the trifluoromethylethylene carbonate product was 64.96%.
  • Example 2 To a 2000 mL three-necked flask, 710 g (5 mol) of 4,4,4-trifluoro-1,3-butanediol and 297 g (1 mol) of triphosgene were added, and 584 g (8 mol) of diethylamine was added dropwise with stirring, 50 5 ° reaction at °C After filtration, the filtrate was rectified under reduced pressure, and 470 g of a fraction of 90 ° C to 95 ° C / 12 mmHg was collected.
  • the collected fractions were detected by gas chromatography Agilent 7890A (RT 4.235), and the fractions were 4, 4, 4-trifluoro- 1, 3-butanediol carbonate purity was 99.91 Wt.%.
  • the yield of the 4,4,4-trifluoro-1,3-butanediol carbonate product was 92.15%.
  • Example 3 To a 2000 mL three-necked flask, 1,80 g (10 mol) of 1,1,1-trifluoro-2,3-pentanediol and 297 g (lmol) of triphosgene were added, and 730 g (10 mol) of n-butylamine was added dropwise with stirring. After reacting at °C for 2 hours, the mixture was filtered, and the filtrate was rectified under reduced pressure to collect 521 g of a fraction of 100 ° C to 120 ° C / 10 mmHg.
  • Example 4 To a 1000 mL three-necked flask, 256 g (2 mol) of trifluoropropanediol and 148.5 g (0.5 mol) of triphosgene were added, and a mixture of 101 g (lmol) of triethylamine and 148 g (2 mol) of propylenediamine was added dropwise with stirring at 20 °C.
  • Example 5 To a 2000 mL three-necked flask, 1420 g (10 mol) of 4,4,4-trifluoro-2,3-butanediol and 297 g (lmol) of triphosgene were added, and 292 g (4 mol) of diethylamine and n-butyl are added dropwise with stirring. Amine 219g (3mol), reacted at 50 ⁇ 60 °C for 3 hours, filtered, and the filtrate was rectified under reduced pressure to collect 465 g of 92 ° C ⁇ 96 ° C / 10 mmHg fraction, and the collected fractions were detected by gas chromatography Agilent 7890A (RT4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Secondary Cells (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

La présente invention concerne un procédé pour préparer un carbonate cyclique de trifluorométhyle, qui comprend les étapes de : ajout d'alcool dihydrique saturé de trifluorométhyle et de triphosgène à un rapport molaire de 1:3 à 1:10 dans une cuve de réaction, ajout d'un agent de liaison d'acide goutte à goutte sous agitation, ajustement de la température dans la cuve à une température comprise entre 0 °C et 80 °C, agitation de la réaction pendant 1 à 12 h pour obtenir le carbonate cyclique de trifluorométhyle, et conduite d'une distillation sous pression réduite pour obtenir le carbonate cyclique de trifluorométhyle. La solution technique décrite n'utilise pas de phosgène toxique en tant que matériau de réaction et peut être aisément utilisée en production industrielle. Le procédé de préparation a un rendement élevé et une pureté de produit supérieure à 99,9 %, et satisfait aux exigences pour l'utilisation en tant qu'électrolyte de batterie lithium-ion.
PCT/CN2012/083398 2012-08-13 2012-10-24 Procédé pour préparer un carbonate cyclique de trifluorométhyle WO2014026432A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2015526854A JP6046257B2 (ja) 2012-08-13 2012-10-24 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
KR1020157003410A KR101691522B1 (ko) 2012-08-13 2012-10-24 트리플루오로메틸 환상 탄산에스테르의 제조방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
WO2014026432A1 true WO2014026432A1 (fr) 2014-02-20

Family

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Application Number Title Priority Date Filing Date
PCT/CN2012/083398 WO2014026432A1 (fr) 2012-08-13 2012-10-24 Procédé pour préparer un carbonate cyclique de trifluorométhyle

Country Status (4)

Country Link
JP (1) JP6046257B2 (fr)
KR (1) KR101691522B1 (fr)
CN (1) CN102807549A (fr)
WO (1) WO2014026432A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (5)

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Publication number Priority date Publication date Assignee Title
CN1075313A (zh) * 1992-02-12 1993-08-18 明尼苏达州采矿制造公司 氟化功能化合物的制备
JP2008230970A (ja) * 2007-03-16 2008-10-02 Daikin Ind Ltd 含フッ素ジオール化合物の製造方法
CN101883752A (zh) * 2007-12-03 2010-11-10 旭硝子株式会社 碳酸酯化合物的制造方法
CN102421768A (zh) * 2009-05-28 2012-04-18 苏威氟有限公司 用于制备4-氟-4-r-5-r’-1，3-二氧杂环戊-2-酮的方法
CN102484283A (zh) * 2009-09-18 2012-05-30 大金工业株式会社 锂二次电池的非水电解液用溶剂

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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
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
JP2010262801A (ja) * 2009-05-01 2010-11-18 Sony Corp 二次電池および電解質
WO2012067248A1 (fr) * 2010-11-19 2012-05-24 三菱化学株式会社 Procédé pour la production d'un dérivé de 4-alcynyl-1,3-dioxolan-2-one

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1075313A (zh) * 1992-02-12 1993-08-18 明尼苏达州采矿制造公司 氟化功能化合物的制备
JP2008230970A (ja) * 2007-03-16 2008-10-02 Daikin Ind Ltd 含フッ素ジオール化合物の製造方法
CN101883752A (zh) * 2007-12-03 2010-11-10 旭硝子株式会社 碳酸酯化合物的制造方法
CN102421768A (zh) * 2009-05-28 2012-04-18 苏威氟有限公司 用于制备4-氟-4-r-5-r’-1，3-二氧杂环戊-2-酮的方法
CN102484283A (zh) * 2009-09-18 2012-05-30 大金工业株式会社 锂二次电池的非水电解液用溶剂

Also Published As

Publication number Publication date
JP2015531761A (ja) 2015-11-05
KR20150034771A (ko) 2015-04-03
JP6046257B2 (ja) 2016-12-14
KR101691522B1 (ko) 2016-12-30
CN102807549A (zh) 2012-12-05

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