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VINYLENE CARBONATE

CAS NUMBER: 872-36-6

EC NUMBER: 212-825-5

MOLECULAR FORMULA: C3H2O3

MOLECULAR WEIGHT: 86.05

Vinylene Carbonate is the simplest unsaturated cyclic carbonic acid ester.
Vinylene Carbonate can also be considered as the cyclic carbonate of hypothetical (Z)-ethene-1,2-diol.
The Vinylene Carbonate double bond makes the molecule a reactive monomer for homopolymerization and copolymerization.
Vinylene Carbonate is a colorless, stable solid.

The starting material of vc is ethylene carbonate.
Vinylene Carbonate is produced in a photochlorination reaction.
The polymerization tendency of liquid Vinylene Carbonate is suppressed by the addition of inhibitors such as butylhydroxytoluene.
Vinylene Carbonate is produced industrially.

Vinylene Carbonate (VC) or 1,3-dioxol-2-one, is the simplest unsaturated cyclic carbonic acid ester.
Vinylene Carbonate can also be thought of as the cyclic carbonate of the hypothetical (Z)-ethene-1,2-diol.
The activated double bond in this five-membered oxygen-containing heterocycle makes the molecule a reactive monomer for homopolymerization and copolymerization and a dienophile in Diels-Alder reactions.

Below room temperature Vinylene Carbonate is a colorless stable solid.
Since its first description in 1953, ethylene carbonate has been commonly used as starting material for Vinylene Carbonate.
In the first stage, monochlorethylene carbonate is produced in a UV-initiated photochlorination reaction with chlorine or sulfuryl chloride at 60-70 °C in bulk.

The role of Vinylene Carbonate (VC) as a thermal additive to electrolytes in lithium ion batteries is studied in two aspects: the protection of liquid electrolyte species and the thermal stability of the solid electrolyte interphase (SEI) formed from Vinylene Carbonate on graphite electrodes at elevated temperatures.
The nuclear magnetic resonance (NMR) spectra indicate that Vinylene Carbonate can not protect LiPF6 salt from thermal decomposition.
However, the function of Vinylene Carbonate on SEI can be observed via impedance and electron spectroscopy for chemical analysis (ESCA).
These results clearly show Vinylene Carbonate-induced SEI comprises polymeric species and is sufficiently stable to resist thermal damage.
It has been confirmed that Vinylene Carbonate can suppress the formation of resistive LiF, and thus reduce the interfacial resistance.

-Quality Level: 100

-Description:Moisture: <10 ppm-Acid content: <10 ppm

-Assay: 99.5%

-Form: liquid

-Refractive index: n20/D 1.421 (lit.)

-Bp: 162 °C (lit.)

-Mp: 19-22 °C (lit.)

-Density: 1.355 g/mL at 25 °C (lit.)

-Featured Industry: Battery Manufacturing

-SMILES string: O=C1OC=CO1

Alkyl carbonates find applications as solvents for lithium ion battery electrolytes and the use of high quality battery grade electrolytes having extremely low water (<10 ppm) and acid (<10 ppm) contents are critical for achieving high electrochemical performance.

In the second stage, monochlorethylenecarbonate undergoes dehydrochlorination with a base such as triethylamine
Instead of in the liquid phase, the dehydrochlorination may also be carried out in the gas phase on a zinc chloride impregnated catalyst in a fluidized bed reactor at 350-500 °C.
The seemingly simple reaction yields only 70 to 80% of impure end product due to a variety of side reactions.
For example, in the chlorination of ethylene carbonate in substance or solution, 2-chloroacetaldehyde, polychlorinated ethylene carbonate and chlorinated ring-opening products are formed besides others.

The separation of the by-products from the final product by distillation by thin-film evaporator,fractional recrystallization or zone melting is very expensive.
The content of by-products can be reduced by stirring with sodium borohydride or urea at elevated temperature.
However, the purification is complicated by the pronounced thermolability of Vinylene Carbonate, as it decomposes at temperatures above 80 °C within minutes.
Highly pure Vinylene Carbonate can be obtained in yields of more than 70% by optimizing the chlorination conditions to suppress the formation of by-products and a combination of several gentle purification processes.
The tendency of the liquid Vinylene Carbonate to polymerize is suppressed by addition of inhibitors such as butylhydroxytoluene (BHT).

Vinylene Carbonate is usually a yellow to brown liquid.
Vinylene Carbonate can be obtained as a solid product with appropriate processing, control and purification steps. Liquid Vinylene Carbonate turns yellow quickly even in the absence of light
Vinylene Carbonate should be stabilized by the addition of radical scavengers.
Vinylene Carbonate is an extremely pure substance in its solid state.

Vinylene Carbonate is stable for a long time when stored below 10 °C.
Vinylene Carbonate is soluble in various solvents such as ethanol, tetrahydrofuran, ethylene carbonate, propylene carbonate.
Also, Vinylene Carbonate is soluble in other dipolar aprotic electrolyte solvents used for lithium-ion rechargeable batteries, such as dimethyl carbonate, diethyl carbonate and the like.
Vinylene Carbonate is widely used as an electrolyte additive for lithium-ion batteries.

The Vinylene Carbonate polymer contributes significantly to the long-term stability of lithium-ion batteries.
Vinylene Carbonate is used as solvents for lithium-ion battery electrolytes
Vinylene Carbonate is a component used in the high quality battery class.
Vinylene Carbonate has a very important role in the use of electrolytes.

Vinylene Carbonate is critical to achieve high electrochemical performance.
Vinylene Carbonate has a low water content.
Vinylene Carbonate is a chemical that should not be kept together with oxidizers.
Vinylene Carbonate is a reactive additive that reacts on both anode and cathode surfaces.

Vinylene Carbonate has a high influence on the behavior of Li-graphite anodes.
Vinylene Carbonate is very convenient as it reduces the irreversible capacity in batteries.
Vinylene Carbonate polymerizes on lithium graphite substrates.
Vinylene Carbonate forms polyalkyl Li-carbonate species that suppress both solvent and salt anion reduction.

The presence of Vinylene Carbonate in solutions reduces the impedance of their cathodes.
Vinylene Carbonate has no significant effect on the cycling behavior of the cathodes at room temperature or elevated temperatures.
Vinylene Carbonate can be considered as a desirable additive for the anode side of Li-ion batteries.
Vinylene Carbonate is a common compound used in many industries.

Polymers:
Already the first work on Vinylene Carbonate describes its bulk polymerization a colorless polymer, which hydrolyzes to a water-soluble product.
Subsequent publications suggest that the first authors produced only low molecular weight oligomers.
The preparation of higher molecular weight polymers with useful properties depends critically on the purity of the Vinylene Carbonate monomer.
Vinylene Carbonate can be homopolymerized in bulk, in solution, in suspension and in dispersion using radical initiators such as azobis(isobutyronitrile) (AIBN) or benzoyl peroxide.
Vinylene Carbonate can also be copolymerized with other vinyl monomers such as vinyl pyrrolidone or vinyl propionate

PolyVinylene Carbonate is readily soluble in acetone and dimethylformamide.
The solutions obtained, however, tend to decompose already at room temperature.
The patent literature describes the use of polyvinyl carbonate for strong fibers, clear, colorless and mechanically strong films, membranes for reverse osmosis and as support during affinity chromatography.
In addition to the instability in solutions, polyvinyl carbonate has the tendency towards hydrolysis in weakly alkaline medium.
This forms polyhydroxymethylene (PHM) via cleavage of the cyclic carbon ring, with the repeating unit –(CHOH)–.
Its behavior is much more similar to cellulose than to the structurally related polyvinyl alcohol with the repeating unit –(CH2–CHOH)–

For example, polyhydroxymethylene films obtained by alkaline hydrolysis of polyVinylene Carbonate films via sodium methoxide in methanol are crystalline and exhibit high tensile strengths.
Analogous to cellulose, polyhydroxymethylene can be dissolved in hot sodium hydroxide solution and converted by crosslinking into a highly swellable polymer which can take up to 10,000 times its weight in water.
Polyhydroxymethylene is soluble in anhydrous hydrazine and can be converted into cellulose-like fibers by spinning in water.
Similar to cellulose, polyhydroxymethylene reacts with carbon disulfide in the alkaline state to form a xanthate, from which water-insoluble polyhydroxymethylene is again obtained by precipitation in dilute sulfuric acid.

Vinylene Carbonate is a chemical that usually has a yellow to brown color.
Vinylene Carbonate is a non-oxidizing compound.
In addition, Vinylene Carbonate does not contain chemical groups that exhibit self-reactive properties such as organic salts of oxidizing acids, sulfonyl halides, sulfonyl cyanides or cyanates.
So Vinylene Carbonate is not self-reactive.

Industrially produced Vinylene Carbonate is usually a yellow to brown liquid.
By suitable process control and purification steps, a solid product with a melting point of 20-22 °C and a chlorine content below 10ppm can be obtained.
Liquid Vinylene Carbonate turns rapidly yellow even in the absence of light and must be stabilised by the addition of radical scavengers.
In solid form, the highly pure substance is long-term stable when stored below 10 °C.

Vinylene Carbonate has been evaluated to possess no oxidising and no explosive properties, based on structural grounds.
Furthermore, the substance does not contain chemical groups indicating self-reactive properties, such as aminonitriles, haloanilines, organic salts of oxidising acids, sulphonyl halides, sulphonyl cyanides, sulphonyl hydrazides, phosphites, strained rings, olefins or cyanates. Therefore, based on structural features it is concluded that the substance is not self-reactive

Why Vinylene Carbonate is a main addictive for lithium-ion batteries?
Vinylene Carbonate is used widely as an electrolyte additive for lithium-ion batteries where it promotes the formation of an insoluble film between the electrolyte and the negative electrode: the SEI (solid-electrolyte-interface).
This polymer film allows ionic conduction, but prevents the reduction of the electrolyte at the negative (graphite) electrode and contributes significantly to the long-term stability of lithium-ion batteries.

-Formula: C3H2O3
-CAS no. 872-36-6
-Gas Response Factor, 11.7 eV: 1.7
-Gas Response Factor, 10.6 eV: 3.5
-Gas Response Factor, 10.0 eV: 5
-ppm per mg/m⁻³, (20 °C, 1 bar): 0.28
-Molecular Weight, g/mole: 86
-Melting point, °C: 21
-Boiling point, °C: 162
-Density, g.cm⁻³: 1.36
-Ionisation Energy, eV: 10.08

Vinylene Carbonate is a chemical that should be kept away from heat and ignition sources.
Vinylene Carbonate is a chemical that is usually stored in a cold and dry environment.
Vinylene Carbonate can be stabilized by the addition of radical scavengers.

USES OF VINYLENE CARBONATE:

Vinylene Carbonate can be used when produced in a photochlorination reaction.
Vinylene Carbonate is used to suppress the polymerization tendency of liquid form by the addition of inhibitors such as butylhydroxytoluene.
Vinylene Carbonate is widely used industrially.
Vinylene Carbonate can be obtained and used as a solid product with appropriate processing, control and purification steps.

Vinylene Carbonate should be stabilized and used by the addition of radical scavengers.
Vinylene Carbonate is used as an extremely pure substance in solid form.

Vinylene Carbonate can be used for a long time when stored below 10 °C.
Vinylene Carbonate can be used in various solvents such as ethanol, tetrahydrofuran, ethylene carbonate, propylene carbonate.

In addition, Vinylene Carbonate can be used in other dipolar aprotic electrolyte solvents.
Vinylene Carbonate is widely used as an electrolyte additive for lithium-ion batteries.
Vinylene Carbonate polymer is used in the long-term stability of lithium-ion batteries.
Vinylene Carbonate is used as a solvent for lithium-ion battery electrolytes

Vinylene Carbonate can be used in high quality battery class.
Vinylene Carbonate is widely used in electrolytes.
Vinylene Carbonate is used to achieve high electrochemical performance.
Vinylene Carbonate can be used to reduce the irreversible capacity of batteries.

Liquid Vinylene Carbonate turns rapidly yellow even in the absence of light and must be stabilized by the addition of radical scavengers.
In solid form, the highly pure substance is long-term stable when stored below 10 °C.
Vinylene Carbonate dissolves in a variety of solvents such as ethanol, tetrahydrofuran, ethylene carbonate, propylene carbonate, and other dipolar aprotic electrolyte solvents used for lithium ion rechargeable batteries such as dimethyl carbonate, diethyl carbonate and the like.

The first publication on Vinylene Carbonate described its Diels-Alder reaction using the example of its addition reaction with 2,3-dimethylbutadiene to a bicyclic carbonate and subsequent hydrolysis to cis-4,5-dihydroxy-1,2-cyclohexene.
Vinylene Carbonate is used widely as an electrolyte additive for lithium-ion batteries where it promotes the formation of an insoluble film between the electrolyte and the negative electrode: the SEI (solid-electrolyte-interface).
This polymer film allows ionic conduction, but prevents the reduction of the electrolyte at the negative (graphite) electrode and contributes significantly to the long-term stability of lithium-ion batteries.
A 2013 publication suggests that the cyclic sultone 3-fluoro-1,3-propanesultone (FPS) is superior to Vinylene Carbonate in SEI formation.

Vinylene Carbonate can also be used for polymerization on lithium graphite substrates.
Vinylene Carbonate is used to form polyalkyl Li-carbonate species that suppress both solvent and salt anion reduction.
Vinylene Carbonate in solutions can be used to reduce the impedance of their cathodes.
Vinylene Carbonate is used in many industries.

APPLICATIONS OF VINYLENE CARBONATE:

-Photochlorination reactions

-Industrial product production

-Additives

-Stabilize processes

-Aprotic electrolyte solvents

-Lithium-ion batteries

-Polyalkyl Li-carbonate species

-Cathode impedance reduction

-Energy products

-Battery manufacturing

Vinylene Carbonate is used as an additive to electrolyte solutions for anode side Lithium-ion batteries.
Vinylene Carbonate also acts as a sealant to seal at least a portion of the silicon-polyvinyl acid interface.
Vinylene Carbonate is further used for great improvement of high temperature performance of the battery.

Vinylene Carbonate (VC) is an effective electrolyte additive to produce a stable solid electrolyte interphase (SEI) on graphite anodes, increasing the capacity retention of lithium-ion cells.
However, in combination with LiNi0.5Mn1.5O4 (LNMO) cathodes, VC drastically decreases cell performance.
In this study we use on-line electrochemical mass spectrometry (OEMS) and electrochemical impedance spectroscopy (EIS) with a micro-reference electrode to understand the oxidative (in-)stability of VC and its effect on the interfacial resistances of both anode and cathode.

We herein compare different Vinylene Carbonate concentrations corresponding to Vinylene Carbonate to graphite surface area ratios typically used in commercial-scale cells.
At low Vinylene Carbonate concentrations (0.09 wt%, corresponding to 1 wt% in commercial-scale cells), an impedance increase exclusively on the anode and an improved capacity retention is observed, whereas higher Vinylene Carbonate concentrations (0.17 wt – 2 wt%, corresponding to 2 wt - 23 wt% in commercial-scale cells) show an increase in both cathode and anode impedance as well as worse cycling performance and overcharge capacity during the first cycle.
By considering the onset potentials for Vinylene Carbonate reduction and oxidation in graphite/LNMO cells, we demonstrate that low amounts of Vinylene Carbonate can be reduced before Vinylene Carbonate oxidation occurs, which is sufficient to effectively passivate the graphite anode.

The effect of Vinylene Carbonate (Vinylene Carbonate) as electrolyte additive on the formation mechanisms of passivation films covering both electrodes in lithium-ion batteries was investigated by X-ray photoelectron spectroscopy (XPS).
LiCoO(2)/graphite coin cells using a LiPF(6)/ethylene carbonate:diethyl carbonate:dimethyl carbonate liquid electrolyte with or without VC were charged at 20 and 60 degrees C.
The identification of VC-derived products formed at the surface of the electrodes was carried out by a dual experimental/theoretical approach.

From a classical XPS core peak analysis completed by a detailed interpretation and simulation of valence spectra supported by ab initio calculations, and through direct synthesis of the Vinylene Carbonate polymer, we could evidence the formation of the radical polyVinylene Carbonate at the electrode/electrolyte interfaces.
We showed that the radical polymerization is the main reaction mechanism of VC contributing to the formation of the passivation layers at the surface of both electrodes.

PHYSICAL PROPERTIES OF VINYLENE CARBONATE:

Physical Description: Liquid

Melting Point: 21 °C

Boiling Point: 60 °C/18 mmHg

Exact Mass: 86.000393922

Monoisotopic Mass: 86.000393922

Molecular Weight: 86.05

CHEMICAL PROPERTIES OF VINYLENE CARBONATE:

Covalently-Bonded Unit Count: 1

Compound Is Canonicalized: Yes

XLogP3-AA: 0.3

Hydrogen Bond Donor Count: 0

Hydrogen Bond Acceptor Count: 3

Rotatable Bond Count: 0

Topological Polar Surface Area: 35.5 Å²

Heavy Atom Count: 6

Formal Charge: 0

Complexity: 84.2

Refractive Index: 1.42

STORAGE OF VINYLENE CARBONATE:

The Vinylene Carbonate should be kept in a still environment.
Vinylene Carbonate should be stored somewhere.
Vinylene Carbonate should be stored in tightly closed containers.

Vinylene Carbonate should be kept away from heat and ignition sources.
Vinylene Carbonate should be stored in a cold environment.
Vinylene Carbonate should be stored in a dry environment.

Vinylene Carbonate should not be stored with oxidizers.
Vinylene Carbonate can be stabilized and stored with the addition of radical scavengers.

Solid Vinylene Carbonate can be stored for a long time when stored below 10 °C.
Vinylene Carbonate should be kept between 0-10°C.

Vinylene Carbonate Must Be Stored Under Inert Gas
Vinylene Carbonate should be stored in a cool environment.
Vinylene Carbonate should be kept away from flash reagents.
Vinylene Carbonate should be stored in specially produced drums.

SYNONYMS:

1,3-Dioxol-2-one
Carbonic acid, cyclic vinylene ester
1,3-Dioxol-2-one, homopolymer
Vinylene Carbonate
Vinyleny carbonate
Carbonic acid vinylene
1,3-Dioxo-2-one
Vinylene Carbonate(VC)
1,3-Dioxol-2-one (9CI)
VAYTZRYEBVHVLE-UHFFFAOYSA-
Carbonic acid, cyclicvinylene ester
1,3-Dioxo-2-one
Vinylene carbote
1,3-DIOXOL-2-ONE
Vinylene carbonat
Vinylene Carbonate