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Vinylene carbonate

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CAS:872-36-6
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Vinylene carbonate Basic information
Product Name:Vinylene carbonate
Synonyms:Vinylene carbonate, 97+%, stab. with BHT;Vinylene carbonate contains <=2% BHT as stabilizer, 97%;The ethylene carbonate;Vinylene carbonate contains 80 ppm BHT as stabilizer, 99%;WITH HYDROQUINONE;Vinylene carbonate 99.5%, acid <200 ppm, H2O <100 ppm;Vinylene carbonate, 97%, stabilized;Vinylene carbote
CAS:872-36-6
MF:C3H2O3
MW:86.05
EINECS:212-825-5
Product Categories:Fine Chemical;fine chemicals;Other
Mol File:872-36-6.mol
Vinylene carbonate Structure
Vinylene carbonate Chemical Properties
Melting point 19-22 °C(lit.)
Boiling point 162 °C(lit.)
density 1.360 g/mL at 20 °C
vapor pressure 3.35hPa at 25℃
refractive index n20/D 1.421(lit.)
Fp 163 °F
storage temp. 2-8°C
solubility 11.5 g/100 mL
form Liquid
color Colorless to pale yellow
Specific Gravity1.355
Water Solubility 11.5 g/100 mL
Sensitive Moisture Sensitive
BRN 105683
InChI1S/C3H2O3/c4-3-5-1-2-6-3/h1-2H
InChIKeyVAYTZRYEBVHVLE-UHFFFAOYSA-N
SMILESO=C1OC=CO1
LogP-0.36 at 20℃
CAS DataBase Reference872-36-6(CAS DataBase Reference)
NIST Chemistry Reference1,3-Dioxol-2-one(872-36-6)
EPA Substance Registry System1,3-Dioxol-2-one (872-36-6)
Safety Information
Hazard Codes Xi,N,T
Risk Statements 43-36-51/53-48/22-41-38-24-22
Safety Statements 37/39-26-24-61-45-36/37/39
RIDADR UN2810 - class 6.1 - PG 3 - EHS - Toxic, liquids, organic, n.o.s., HI: all
WGK Germany 3
RTECS FG3325000
TSCA TSCA listed
HazardClass 6.1
HS Code 29209090
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Dermal
Acute Tox. 4 Oral
Aquatic Chronic 2
Eye Dam. 1
Skin Irrit. 2
Skin Sens. 1
STOT RE 2 Oral
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Vinylene carbonate Usage And Synthesis
Chemical Propertiesclear colorless to light yellow liquid
UsesVinylene carbonate is used as an additive to electrolyte solutions for anode side Lithiumion batteries. It also acts as a sealant to seal at least a portion of the silicon-polyvinyl acid interface. It is further used for great improvement of high temperature performance of the battery.
ApplicationVinylene carbonate (VC) can be used as an electrolytic additive for ionic liquid electrolyte for the formation of lithium-ion batteries. It can also be used in the formation of hybrid solid electrolyte interphase (SEI) for the fabrication of lithium-based batteries.
PreparationVinylene carbonate is produced by the known method by eliminating hydrogen chloride from chloroethylene glycol carbonate by means of tertiary amines, in particular triethylamine. Chloroethylene glycol carbonate is obtained by free radical chlorination of ethylene glycol carbonate by means of chlorine or sulphuryl chloride. This synthesis was published for the first time in 1953 by Newman and Addor (JACS, 1953, page 1263; JACS 1955, page 3789).
General DescriptionThis product has been enhanced for energy efficiency. Carbonate building block offered as a solution in ethyl acetate for more convenient handling. Vinylene carbonate may also be used as a dienophile in Diels-Alder reactions.
Flammability and ExplosibilityNon flammable
Synthesis
Chloroethylene carbonate

3967-54-2

Vinylene carbonate

872-36-6

General procedure for the synthesis of vinylidene carbonate from chlorinated ethylene carbonate (CEC): 61.3 kg (500 mmol) of chlorinated ethylene carbonate, 151 kg (1500 mmol) of triethylamine, 120 kg of ethyl acetate, and 61.3 g of p-tert-butyl catechol were added to a mixer and stirred until completely dissolved. The mixed solution was injected into a horizontal tubular reactor at a flow rate of 0.05 m/s, and the reaction temperature was controlled at 25-30 °C for 100 min. After completion of the reaction, the solid triethylamine hydrochloride was removed by filtration. The filtrate was washed with 30% sodium hydroxide solution and then indirectly heated by steam (0.25 MPa), and the evaporated triethylamine was recovered by a condenser. The treated filtrate was added to the coolant of the dechlorination section and distilled under reduced pressure to recover ethyl acetate. Subsequently, distillation was carried out with a controlled pressure of 0.098 MPa and the fractions at 160-165 °C were collected to give vinylidene carbonate in 96.5% yield and 99.5% GC purity.

Purification MethodsPurify it by zone melting, or distillation, and stabilize it with 0.5% of 2,6-di-tert-butyl-p-cresol. [Beilstein 19 III/IV 1597, 19/4 V 72.]
Toxics Screening LevelThe initial threshold screening level (ITSL) for vinylene carbonate (CAS # 872-36-6) is 0.1 μg/m3 based on an annual averaging time.
References[1] Patent: CN104844556, 2017, B. Location in patent: Paragraph 0029; 0030
[2] Patent: CN106699720, 2017, A. Location in patent: Paragraph 0017
[3] Patent: CN106632225, 2017, A. Location in patent: Paragraph 0017; 0018; 0019; 0020; 0021
[4] Patent: US2009/176997, 2009, A1. Location in patent: Page/Page column 2-3
[5] Patent: WO2006/119911, 2006, A1. Location in patent: Page/Page column 4
Tag:Vinylene carbonate(872-36-6) Related Product Information
Vinyl acetate Chloroethylene carbonate Polycarbonate Dimethyl carbonate Lithium carbonate Sodium carbonate Zinc carbonate Ammonium carbonate Fluoroethylene carbonate Ethylene carbonate 4-Vinyl-1,3-dioxolan-2-one ALLYL PHENYL CARBONATE 97 VINYLTRIISOPROPENOXYSILANE Vinyltriacetoxysilane Calcium carbonate Propylene carbonate Barium carbonate PHENYL FORMATE

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