CN104529992A - Preparation method for 4,5-difluoro-1,3-dioxolan-2-one - Google Patents
Preparation method for 4,5-difluoro-1,3-dioxolan-2-one Download PDFInfo
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- CN104529992A CN104529992A CN201410687629.8A CN201410687629A CN104529992A CN 104529992 A CN104529992 A CN 104529992A CN 201410687629 A CN201410687629 A CN 201410687629A CN 104529992 A CN104529992 A CN 104529992A
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- preparation
- difluorinated ethylene
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- dichloro
- difluorinated
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- 238000002360 preparation method Methods 0.000 title claims description 18
- DSMUTQTWFHVVGQ-UHFFFAOYSA-N 4,5-difluoro-1,3-dioxolan-2-one Chemical compound FC1OC(=O)OC1F DSMUTQTWFHVVGQ-UHFFFAOYSA-N 0.000 title abstract 3
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000011230 binding agent Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical class O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 33
- 238000004821 distillation Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- -1 inorganic base compound Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 238000003682 fluorination reaction Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- VAYTZRYEBVHVLE-UHFFFAOYSA-N 1,3-dioxol-2-one Chemical compound O=C1OC=CO1 VAYTZRYEBVHVLE-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000007701 flash-distillation Methods 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 238000000199 molecular distillation Methods 0.000 claims description 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 7
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 5
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 5
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- BETICXVUVYXEJX-UHFFFAOYSA-N 4,5-Dichloro-1,3-dioxolan-2-one Chemical compound ClC1OC(=O)OC1Cl BETICXVUVYXEJX-UHFFFAOYSA-N 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000002000 Electrolyte additive Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical group ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 abstract 1
- 239000012025 fluorinating agent Substances 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HIGQQEOWQNDHJD-UHFFFAOYSA-N 4,4-dichloro-1,3-dioxolan-2-one Chemical compound ClC1(Cl)COC(=O)O1 HIGQQEOWQNDHJD-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07D317/08—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
- C07D317/42—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a manufacture method of a lithium ion battery electrolyte additive 4,5-difluoro-1,3-dioxolan-2-one. The method comprises: diluting 4,5-dichloro-1,3-dioxolan-2-one in an organic ether solvent, performing fluorine-chloride substitution reaction on 4,5-dichloro-1,3-dioxolan-2-one and a fluorinating agent under the initiation of an acid binding agent, so as to prepare 4,5-difluoro-1,3-dioxolan-2-one. The method is mild in conditions, simple to operate and high in selectivity, and is suitable for industrialized production.
Description
Technical field
The present invention relates to a kind of synthesis of lithium-ion battery electrolytes additive two fluoro carbonic ester, refer more particularly to a kind of synthetic method of difluorinated ethylene carbonate.
Background technology
Difluorinated ethylene carbonate can be used as electrolyte for lithium ion battery additive or mixed additive, there is use temperature wide ranges, physical and chemical stability is good, resistance to pressure is excellent, and there is high flash point, the safety performance of lithium ion battery can be promoted and extend the service life cycle of lithium ion battery.
The preparation method of difluorinated ethylene carbonate mainly contains preparation method and Potassium monofluoride that simple substance fluoride and NSC 11801 carry out and the preparation method that dichloro-NSC 11801 is reacted.
US Patent No. 20120177987 discloses one and utilizes simple substance fluoride and NSC 11801 substitution reaction to prepare many fluorinated ethylene carbonates, and reacted constituent is complicated, and yield is not high, separating difficulty is large, and using simple substance fluoride toxicity large, equipment requirements is high, and safety and environmental protection is strict.
US Patent No. 2011048053 describes and uses acetonitrile as solvents to utilize KF and dichloro-ethylene carbonate Lipase absobed difluorinated ethylene carbonate, the method reaction for up to 18 hours, low conversion rate, effect is not satisfactory, is not suitable for large-scale industrial production.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, a kind of synthetic method of preparation 4,5-difluorinated ethylene carbonate of gentleness is provided.
In order to solve the problem, the invention provides a kind of following technical scheme:
A kind of 4, the preparation method of 5-difluorinated ethylene carbonate, it is characterized in that: 4,5-dichloro-NSC 11801 and fluorizating agent are diluted in organic solvent, by this mixture holding temperature at-10 ~ 100 DEG C, then acid binding agent is dripped, after the reaction of generation fluorine chlorine terminates, carry out solid-liquid separation, air distillation precipitation, further evaporated under reduced pressure purification obtains 4, the 5-difluorinated ethylene carbonates that purity is greater than 99.90%.
Reaction equation is as follows:
In a preferred embodiment of the invention: the mol ratio of described 4,5-dichloro-NSC 11801, fluorination reagent and acid binding agent is 1:0.6:1.4 ~ 1:5:0.5.
In a preferred embodiment of the invention: described fluorination reagent is organic amine hydrofluoride.
In a preferred embodiment of the invention: described acid binding agent can be inorganic base compound, pyridine compounds and their, any one in aminated compounds, organic amine compound.
In a preferred embodiment of the invention: described organic solvent is organic ethers.
In a preferred embodiment of the invention: the weight of described organic solvent is 1 ~ 5 times of 4,5-dichloro-NSC 11801 weight.
In a preferred embodiment of the invention: use 4,5-dichloro-NSC 11801 be vinylene carbonate and sulfuryl chloride under high voltage mercury lamp or the effect of initiator Diisopropyl azodicarboxylate issue raw free radical and replace and produce, or under the effect of purple light, pass into chlorine by NSC 11801 and synthesize.
In a preferred embodiment of the invention: the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: described solid-liquid separating method is press filtration mode.
In a preferred embodiment of the invention: it is characterized in that described distillation precipitation is flash distillation precipitation.
In a preferred embodiment of the invention: described molecular distillation is carried out in Graphite Tower.
Wherein with Et
3nnHF is fluorination reagent, and ether is that the reaction equation of solvent is as follows:
Beneficial effect of the present invention is: the reaction times is 2 ~ 4 hours, and the reaction times is very fast, and selectivity is good.Use organic amine to make acid binding agent and initiator, reaction conversion ratio is high.Use organic ether to make solvent, be easy to solid-liquid separation and rectifying of purifying further.Utilize Graphite Tower rectifying, prevent product acid attack and decomposition.Mild condition of the present invention, has economy, practicality.
Embodiment
Below in conjunction with specific embodiment, the present invention will be further described:
Embodiment 1
Take 157g (1mol) dichloro-NSC 11801, the borontrifluoride hydrogen salt of 64g fluorizating agent pyridine (
) be dissolved in the reaction vessel of 400ml ether, acid binding agent pyridine 120g is dripped at-10 DEG C, time for adding 1 hour, drip end 10 ~ 20 DEG C insulation 2 hours, filter, filtrate is sloughed ether through air distillation and is obtained difluorinated ethylene carbonate crude product, then underpressure distillation obtains the difluorinated ethylene carbonate 99g of purity 99.92%, yield 80.58%.
Embodiment 2
Take 157g (1mol) dichloro-NSC 11801,65g fluorizating agent triethylamine trihydrofluoride salt (Et
3n3HF) be dissolved in the reaction vessel of 400ml tetrahydrofuran (THF), acid binding agent triethylamine 145g is dripped at-5 DEG C, time for adding 1 hour, drip end 10 ~ 20 DEG C insulation 2 hours, filter, filtrate is sloughed solvent through air distillation and is obtained difluorinated ethylene carbonate crude product, then underpressure distillation obtains the difluorinated ethylene carbonate 105.5g of purity 99.94%, yield 85%.
Embodiment 3
Take 1570g (10mol) dichloro-NSC 11801,660g fluorizating agent triethylamine trihydrofluoride salt (Et
3n3.5HF) be dissolved in the reaction vessel of 4500ml methyl tertiary butyl ether, acid binding agent triethylamine 1500g is dripped at-5 DEG C, time for adding 2.5 hours, drip end 10 ~ 30 DEG C insulation 4 hours, filter, filtrate is sloughed solvent through air distillation and is obtained difluorinated ethylene carbonate crude product, then underpressure distillation obtains the difluorinated ethylene carbonate 1100g of purity 99.96%, yield 88.7%.
Embodiment 4
Take 3140g (20mol) dichloro-NSC 11801,1340g fluorizating agent triethylamine tetrafluoride hydrogen salt (Et
3n4HF) be dissolved in the reaction vessel of 9500ml methyl tertiary butyl ether, acid binding agent triethylamine 3000g is dripped at-5 DEG C, time for adding 3 hours, drip end 10 ~ 30 DEG C insulation 4 hours, filter, filtrate is sloughed solvent through air distillation and is obtained difluorinated ethylene carbonate crude product, then underpressure distillation obtains the difluorinated ethylene carbonate 2200g of purity 99.96%, yield 86%.
Claims (10)
1. one kind 4, the preparation method of 5-difluorinated ethylene carbonate, it is characterized in that: 4,5-dichloro-NSC 11801 and fluorizating agent are diluted in organic solvent, this solution is maintained to-10 ~ 100 DEG C, then acid binding agent is dripped, reaction terminates, solid-liquid separation, distillation precipitation, distilation obtains cell-grade 4, the 5-difluorinated ethylene carbonate that purity is greater than 99.95% under a high vacuum.
2. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: the mol ratio of described 4,5-dichloro-NSC 11801, fluorination reagent and acid binding agent is 1:0.6:1.4 ~ 1:5:0.5.
3. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: described fluorination reagent is organic amine hydrofluoride.
4. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: described acid binding agent can for inorganic base compound, pyridine compounds and their, any one in aminated compounds, organic amine compound.
5. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: described organic solvent is organic ethers.
6. the preparation method of a kind of 4,5-difluorinated ethylene carbonate according to claim 1 or 5, is characterized in that: the weight of described organic solvent is 1 ~ 5 times of 4,5-dichloro-NSC 11801 weight.
7. according to claim 1 a kind of 4, the preparation method of 5-difluorinated ethylene carbonate, it is characterized in that: use 4,5-dichloro-NSC 11801 be vinylene carbonate and sulfuryl chloride under high voltage mercury lamp or the effect of initiator Diisopropyl azodicarboxylate issue raw free radical and replace and produce, or under the effect of purple light, pass into chlorine by NSC 11801 and synthesize.
8. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: described solid-liquid separating method is press filtration mode.
9. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: it is characterized in that described distillation precipitation is flash distillation precipitation.
10. the preparation method of a kind of 4,5-difluorinated ethylene carbonates according to claim 1, is characterized in that: described molecular distillation is carried out in Graphite Tower.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410687629.8A CN104529992A (en) | 2014-11-26 | 2014-11-26 | Preparation method for 4,5-difluoro-1,3-dioxolan-2-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410687629.8A CN104529992A (en) | 2014-11-26 | 2014-11-26 | Preparation method for 4,5-difluoro-1,3-dioxolan-2-one |
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| CN104529992A true CN104529992A (en) | 2015-04-22 |
Family
ID=52845664
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|---|---|---|---|
| CN201410687629.8A Pending CN104529992A (en) | 2014-11-26 | 2014-11-26 | Preparation method for 4,5-difluoro-1,3-dioxolan-2-one |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105719421A (en) * | 2016-04-27 | 2016-06-29 | 丛静华 | Big data mining based integrated forest fire prevention informatization system |
| CN106083806A (en) * | 2016-06-27 | 2016-11-09 | 天津市职业大学 | A kind of method preventing chlorocarbonic acid vinyl acetate from decomposing |
| CN106905290A (en) * | 2017-03-08 | 2017-06-30 | 江苏理文化工有限公司 | A kind of preparation method of difluoroethylene carbonate |
| CN107903240A (en) * | 2017-11-13 | 2018-04-13 | 张家港瀚康化工有限公司 | The preparation method of difluoroethylene carbonate |
| CN110684006A (en) * | 2019-10-27 | 2020-01-14 | 淮安瀚康新材料有限公司 | Preparation method of high-purity difluoroethylene carbonate |
| CN110903274A (en) * | 2019-12-18 | 2020-03-24 | 江苏华盛锂电材料股份有限公司 | 4, 5-difluoroethylene carbonate and preparation method thereof |
| CN113896705A (en) * | 2021-11-09 | 2022-01-07 | 青岛科技大学 | Synthetic method for co-production of 1-fluoro-2-chloroethylene carbonate and 1,2-difluoroethylene carbonate |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105719421A (en) * | 2016-04-27 | 2016-06-29 | 丛静华 | Big data mining based integrated forest fire prevention informatization system |
| CN105719421B (en) * | 2016-04-27 | 2017-11-28 | 丛静华 | A kind of integrated forest fire protection information system excavated based on big data |
| CN106083806A (en) * | 2016-06-27 | 2016-11-09 | 天津市职业大学 | A kind of method preventing chlorocarbonic acid vinyl acetate from decomposing |
| CN106083806B (en) * | 2016-06-27 | 2019-04-19 | 天津市职业大学 | A kind of method for preventing the decomposition of chloroethylene carbonate |
| CN106905290A (en) * | 2017-03-08 | 2017-06-30 | 江苏理文化工有限公司 | A kind of preparation method of difluoroethylene carbonate |
| CN106905290B (en) * | 2017-03-08 | 2019-06-07 | 江苏理文化工有限公司 | A kind of preparation method of difluoroethylene carbonate |
| CN107903240A (en) * | 2017-11-13 | 2018-04-13 | 张家港瀚康化工有限公司 | The preparation method of difluoroethylene carbonate |
| CN110684006A (en) * | 2019-10-27 | 2020-01-14 | 淮安瀚康新材料有限公司 | Preparation method of high-purity difluoroethylene carbonate |
| CN110903274A (en) * | 2019-12-18 | 2020-03-24 | 江苏华盛锂电材料股份有限公司 | 4, 5-difluoroethylene carbonate and preparation method thereof |
| CN110903274B (en) * | 2019-12-18 | 2022-12-16 | 江苏华盛锂电材料股份有限公司 | 4, 5-difluoroethylene carbonate and preparation method thereof |
| CN113896705A (en) * | 2021-11-09 | 2022-01-07 | 青岛科技大学 | Synthetic method for co-production of 1-fluoro-2-chloroethylene carbonate and 1,2-difluoroethylene carbonate |
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Application publication date: 20150422 |