VINYLENE CARBONATE

Vinylene carbonate is used as an additive to electrolyte solutions for anode side Lithiumion 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.

CAS Number: 872-36-6 
EC Number: 212-825-5
Chemical formula: C3H2O3
Molar mass: 86.05 g·mol−1

SYNONYMS:
2H-1,3-Dioxol-2-one, 1,3-Dioxolene-2-one, Vinyl carbonate, VINYLENE CARBONATE, 1,3-Dioxol-2-one, 872-36-6, 1X0ZZF9WFV, NSC-20980, NSC-47201, DTXSID1074888, LBG-84922, RefChem:901949, DTXCID8048573, 212-825-5, Vinyl carbonate, 2H-1,3-dioxol-2-one, Carbonic acid, cyclic vinylene ester, MFCD00005380, C3H2O3, Vinylene carbonate (stabilized with BHT), WLN: T5OVOJ, 25747-73-3, Vinylene Carbonate (Contains Up to 2% BHT), EINECS 212-825-5, NSC 20980, NSC 47201, BRN 0105683, starbld0011148, UNII-1X0ZZF9WFV, EC 212-825-5, SCHEMBL35245, SCHEMBL992934, SCHEMBL15049055, VAYTZRYEBVHVLE-UHFFFAOYSA-, Carbonic acid, cyclicvinylene ester, BB_SC-06550, NSC20980, NSC47201, BBL027517, STL373475, AKOS015855830, CS-W013752, MSK181984-100B, SB66334, SY001314, CYCLIC VINYLENE ESTER CARBONIC ACID, DB-056985, NS00005704, V0015, Vinylene carbonate, purum, >=97.0% (GC), EN300-120679, 872V366, A842047, F386738, Vinylene carbonate Solution in Acetone, 100ug/mL, Q2802973, InChI=1/C3H2O3/c4-3-5-1-2-6-3/h1-2H, Vinylene carbonate, contains <=2% BHT as stabilizer, 97%, Vinylene carbonate, 99.5%, acid <200 ppm, H2O <100 ppm, Vinylene carbonate, contains 80 ppm BHT as stabilizer, 99%, 1,3-Dioxol-2-one, VC, 1,3-DIOXOL-2-ONE, vinyl carbonate, Vinylene carbote, The ethylene carbonate, Vinylene carbonate, 99%, water ≤50 ppm, stabilized with 90 ppm BHT, 1,3-Dioxo-2-one, WITH HYDROQUINONE, Vinylene carbonat, VINYLENE CARBONATE, 2H-1,3-dioxol-2-one

Vinylene Carbonate is a clear colorless to light yellow liquid
Vinylene carbonate, as well as the majority of 1,2 substituted ethylene compounds, has a low activity in the reactions of copolymerization.
The structure of the vinylene carbonate radical determines its tendency toward reactions of chain transfer to a solvent or an impurity; this leads to a significant decrease in the copolymerization rate and the molecular weight of a copolymer produced.

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.
Vinylene carbonate has been reported in Microbispora with data available.
Vinylene carbonate is a product of high purity (min. 99.99%) with free chlorine content below 15 ppm.

Vinylene Carbonate is used mainly for the production of electrolytes for lithium-ion batteries (Li-Ion).
Vinylene Carbonate is also a raw material/intermediate in the organic synthesis of membrane materials.
Vinylene carbonate is of particular importance for the dynamically developing sector of Li-Ion batteries and accumulators.

As a specialist additive for electrolytes, Vinylene Carbonate promotes the creation of membranes in the process of film formation.
Additives of this type improve stability by preventing the formation of dendrites and degradation of electrolyte solution.

Vinylene carbonate is an important product for the broadly understood consumer electronics industry, especially for the production of electrolytes for lithium-ion batteries (Li-Ion), where it is used as an additive promoting the formation of membranes and precursor for polymerisation.

Owing to the presence of unsaturated bonding in Vinylene Carbonate's structure the product can be also used in the polymerisation process to obtain membranes and protective and separating coatings, which is of crucial importance, e.g. in the production of capsule coatings (pharmaceutical industry) or fixing agents (colourant and pigment industry).

Vinylene carbonate is produced as a colourless clear liquid having a characteristic odour, stabilised by adding antioxidants and free radical scavengers (BHT 70-110 ppm) to avoid polymerisation.
Vinylene carbonate dissolves in ethanol, tetrahydrofuran, ethylene carbonate, propylene carbonate and dimethyl carbonate and diethyl carbonate (electrolytic solvents used in lithium-ion accumulators).

Vinylene carbonate (VC), chemically known as 1,3-dioxol-2-one, is the simplest unsaturated cyclic carbonic acid ester with the molecular formula C₃H₂O₃ and a molar mass of 86.05 g/mol.
Vinylene Carbonate features a five-membered ring structure consisting of a carbonate group integrated with a vinylene (C=C) moiety, rendering it highly reactive as a dienophile in Diels-Alder reactions and as a monomer for polymerization.

Vinylene Carbonate appears as a colorless to pale yellow liquid at room temperature, with a density of 1.36 g/mL at 20 °C, a melting point of 19–22 °C, a boiling point of 162 °C, and limited solubility in water (11.5 g/100 mL).
Its vapor pressure is low (3.35 hPa at 25 °C), and Vinylene Carbonate is moisture-sensitive, requiring storage at 2–8 °C to maintain stability.

Synthesized industrially through the dehydrochlorination of chloroethylene carbonate—itself derived from the free-radical chlorination of ethylene carbonate—vinylene carbonate serves as a key intermediate in organic synthesis.
This process, first detailed in mid-1950s research, involves treating monohaloethylene carbonate with a base like triethylamine to eliminate HCl, yielding high-purity Vinylene Carbonate suitable for specialized applications.

Beyond its role in forming polycarbonates and other polymers via radical or anionic polymerization, Vinylene Carbonate exhibits versatility as a synthon in transition metal-catalyzed C–H functionalizations, enabling the construction of complex heterocycles such as indazolo[2,3-a]quinolines.
However, its primary industrial significance lies in electrochemistry, where Vinylene Carbonate acts as a reactive additive rather than a bulk material.

Vinylene Carbonate is the smallest unsaturated cyclic carbonic acid ester.
Vinylene Carbonate is used as an additive for electrolyte solutions for Lithium-ion and Sodium-ion batteries.
Vinylene carbonate, or 1,3-dioxol-2-one, abbreviated VC, is the simplest unsaturated cyclic carbonic acid ester.

Vinylene carbonate can also be considered the cyclic carbonate of the hypothetical (Z)-ethene-1,2-diol.
The activated double bond in this five-membered oxygen-containing heterocycle makes Vinylene Carbonate a reactive monomer for homopolymerization and copolymerization, and a dienophile in Diels-Alder reactions.

In highly pure form, vinylene carbonate is a colorless, stable solid below room temperature.
Vinylene carbonate (VC) is a cyclic carbonate with the chemical formula C_4H_4O_3.
Vinylene Carbonate was first synthesized in the early 20th century and has since gained attention in various chemical applications.

Vinylene Carbonate is characterized by its distinctive structure, which includes a carbonyl group attached to a vinylene group, making it an interesting subject of study in both academic and industrial chemistry.
Ethylene carbonate has been the common starting material for vinylene carbonate since its first description in 1953.

In a UV-initiated photochlorination reaction with chlorine or sulfuryl chloride at 60–70 °C in bulk, monochloroethylene carbonate is formed in the first stage, which in the second stage is converted to vinylene carbonate or MTBE, by dehydrochlorination e.g. with triethylamine, possibly diluted with ethylene carbonate, at 40–60 °C.

Instead of in the liquid phase, dehydrochlorination can also be carried out in the gas phase over a zinc chloride-impregnated contact in a fluidized bed reactor at 350–500 °C with average yields of 69% of theory.
This seemingly simple reaction pathway yields only 70 to 80% of theory of impure end product due to a large number of side reactions.

For example, the chlorination of ethylene carbonate in bulk or solution produces, among other things, 2-chloroacetaldehyde, polychlorinated ethylene carbonates, and, via ring opening, other chlorine-containing compounds, the separation of which from the end product by distillation using a thin-film evaporator, fractional recrystallization, or zone melting is very complex.

The content of byproducts can also be reduced by stirring with sodium borohydride or urea at elevated temperature.
The pronounced thermolability of vinylene carbonate is also problematic; it decomposes within minutes at temperatures above 80 °C.

High-purity vinylene carbonate can be obtained in yields exceeding 70% of theory by optimizing the chlorination conditions to suppress byproduct formation and by combining several gentle purification processes.
The polymerization tendency of liquid VC is suppressed by the addition of inhibitors such as butylhydroxytoluene (BHT).

USES and APPLICATIONS of VINYLENE CARBONATE:
Vinylene carbonate (VC) was tested as an additive to electrolyte solutions for Li-ion batteries.
For the model electrodes, synthetic graphite was chosen as the anode material, while LiMn2O4 spinel and LiNiO2 were chosen as the cathode materials.
The test solution was 1 M LiAsF6 in a 1:1 mixture of ethylene and dimethyl carbonates (EC–DMC).

Vinylene Carbonate, chronopotentiometry, impedance spectroscopy, electrochemical quartz crystal microbalance (EQCM), FTIR and X-ray photoelectron spectroscopies have been used in this study.
It was found that Vinylene Carbonate is a reactive additive that reacts on both the anode and the cathode surfaces.

The influence of this additive on the behavior of Li–graphite anodes is very positive, since Vinylene Carbonate improves their cyclability, especially at elevated temperatures, and reduces the irreversible capacity.
The spectroscopic studies indicate that Vinylene Carbonate polymerizes on the lithiated graphite surfaces, thus forming poly alkyl Li-carbonate species that suppress both solvent and salt anion reduction.

The presence of Vinylene Carbonate in solutions reduces the impedance of the LiMn2O4 and LiNiO2 cathodes at room temperature.
However, we have not yet found any pronounced impact of Vinylene Carbonate on the cycling behavior of the cathodes, either at room temperature or at elevated temperatures.

Thus, Vinylene Carbonate can be considered as a desirable additive for the anode side in Li-ion batteries, one which has no adverse effect on the cathode side.
Vinylene carbonate is used as an additive to electrolyte solutions for anode side Lithiumion 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) can be used as an electrolytic additive for ionic liquid electrolyte for the formation of lithium-ion batteries.

Vinylene Carbonate can also be used in the formation of hybrid solid electrolyte interphase (SEI) for the fabrication of lithium-based batteries.
Vinylene Carbonate 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.
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, the smallest unsaturated cyclic carbonic acid ester, finds application as an additive in electrolyte solutions for Lithium-ion and Sodium-ion batteries.

Moreover, vinylene carbonate exhibits biocompatible properties, rendering it suitable for various biomedical applications.
While sharing a polymer structure akin to polyvinylene (PV), vinylene carbonate demonstrates superior stability at elevated temperatures compared to PV.

This enhanced thermal stability expands Vinylene Carbonate's potential uses in demanding environments.
Vinylene Carbonate is mainly used as organic synthesis intermediates or as addition in electrolyte for lithium ion batteries (LIB).
Adding Vinylene Carbonate in electrolyte can greatly increase the battery capacity and cycle life.

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, Vinylene Carbonate, 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.
3-Fluor-1,3-propanesultone: Since 1,3-propane sultone, on which FPS is based, is classified as a particularly dangerous carcinogenic substance, a significant hazard potential must also be assumed for FPS.

The most notable application of vinylene carbonate is as an electrolyte additive in lithium-ion batteries (LIBs), where it preferentially reduces at the anode surface to form a robust, thin solid electrolyte interphase (SEI) layer.

This SEI, composed of poly(vinylene carbonate) and inorganic components, passivates the electrode, suppresses electrolyte decomposition, and enhances Coulombic efficiency, cycle life, and high-temperature stability—critical for applications in electric vehicles and portable electronics.

Studies show that even low concentrations (1–5 wt%) of Vinylene Carbonate significantly improve capacity retention by mitigating lithium dendrite growth and oxidative instability at high voltages.
Despite these benefits, Vinylene Carbonate is acutely toxic upon dermal or oral exposure, causing skin and eye irritation, and poses environmental risks as an aquatic chronic hazard, necessitating careful handling with protective equipment.

Vinylene carbonate (VC) is an important additive in lithium-ion batteries, which plays a crucial role in various battery performance aspects.
Vinylene Carbonate can be considered as the "blood" of the battery.
With the continuous development of lithium-ion batteries, users have increasingly higher requirements for their performance.

The use of additives in the battery electrolyte is an important solution to achieve better performance.
Among the additives in lithium-ion battery electrolytes, Vinylene carbonate (VC) is the most extensively studied and ideal organic film-forming additive.

It has been reported that Vinylene Carbonate can undergo free radical polymerization on the surface of the carbon negative electrode, forming polyalkyl carbonate compounds.
This effectively inhibits the co-insertion reaction of solvent molecules and has no side effects on the positive electrode.

Practical applications have shown that Vinylene carbonate can significantly extend the cycle life of lithium-ion batteries and improve their storage stability, making it an important electrolyte additive for lithium-ion batteries.
Vinylene Carbonate (C3H2O3) is often utilized as solvents for lithium-ion battery electrolytes.

Vinylene Carbonate is electrochemically active and decomposes at low anodic potentials on lithium metal anodes, forming polymeric species that often yield a desirable solid-electrolyte interphase.
Vinylene Carbonate is frequently used as a co-solvent with other carbonate solvents in lithium-ion battery electrolyte formulations to improve the performance and stability of the battery.

Vinylene carbonate also participates in ring-opening polymerization to generate poly(vinylene carbonate), a polymer with potential in non-electrolyte applications such as coatings and adhesives.
This polymerization can be initiated radically or via other methods, yielding materials with hydrolyzable carbonate linkages that enable post-polymerization modifications.

Telechelic polyolefins end-capped with vinylene carbonate units, prepared through ring-opening metathesis polymerization followed by cross-metathesis, serve as precursors for non-isocyanate polyurethanes suitable for coatings, adhesives, foams, and sealants, offering a sustainable alternative to traditional isocyanate-based systems.

Beyond direct reactivity, vinylene carbonate acts as a precursor for substituted derivatives via organocatalytic methods, enhancing its versatility in green chemistry routes.
For example, imidazolium salt catalysts facilitate the synthesis of aryl-substituted vinylene carbonates from benzoins and diphenyl carbonate, achieving yields up to 99% under mild conditions (100–130°C), with recyclability of the catalyst.

These transformations align with sustainable practices, as demonstrated in the organocatalytic upcycling of poly(bisphenol A carbonate) waste to vinylene carbonates using dimethyl carbonate as a carbonyl source, promoting CO₂-derived circular economy approaches without halogenated reagents.

Vinylene carbonate (VC) is a new type of film forming additive and overcharge protection additive for lithium-ion batteries.
Vinylene Carbonate can form a layer of solid electrolyte interface film (SEI film) by electrochemical reaction on the negative electrode surface during the initial charge and discharge of lithium-ion batteries, and effectively inhibit the embedding of solvent molecules.

Vinylene Carbonate has good performance at high and low temperature, and excellent anti-bloating function.
Vinylene carbonate can improve the capacity and cycle life of the lithium-ion battery.
In addition, Vinylene Carbonate can also be used as a monomer for the preparation of polyvinyl carbonate.

-The application of vinylene carbonate in Li-ion batteries:
Vinylene carbonate is a monomer used for producing important technical products, e.g., polyvinylene carbonate, polyvinylene glycol, and polyvinylene acetal.
From polyvinylene carbonate and its derivatives, one can obtain high strength fibers, films and organic glass resistant to destructive effects, prophylactic drugs against ionizing radiation, and selective sorbents of boron and other rare elements.

APPLICATIONS of VINYLENE CARBONATE:
ELECTROLYTE ADDITIVE IN BATTERIES
Vinylene carbonate (VC) serves as a key electrolyte additive in lithium-ion batteries, typically incorporated at concentrations of 1–5 wt% into carbonate-based solvents such as ethylene carbonate/dimethyl carbonate (EC/DMC) mixtures, to promote the formation of a stable solid electrolyte interphase (SEI) on graphite anodes via reductive polymerization.

This low-concentration addition enhances interfacial stability without significantly altering bulk electrolyte properties.
The mechanism relies on Vinylene Carbonate's preferential electrochemical reduction at lower potentials than the primary solvents, initiating ring-opening and polymerization to yield a protective passivation layer enriched in lithium carbonate (Li₂CO₃) and poly(Vinylene Carbonate) components.

This process can be approximated by the reaction:
VC+2e−+2Li+→poly(VC)+Li2CO3VC+2e − +2Li + →poly(VC)+Li2CO3
The resulting SEI exhibits high ionic conductivity, mechanical flexibility, and resistance to further electrolyte decomposition, thereby minimizing continuous growth and capacity fade.

Key benefits include extended cycle life exceeding 1000 cycles under high-voltage conditions (e.g., up to 4.5 V), reduced iron (Fe) dissolution from lithium iron phosphate (LFP) cathodes during elevated-temperature operation, and suppression of gas evolution from side reactions.
In LFP/graphite pouch cells cycled at 70 °C, Vinylene Carbonate addition at 5 wt% significantly lowered Fe migration to the anode and curtailed electrolyte breakdown, preserving over 80% capacity retention after 500 cycles.

Recent 2024–2025 investigations further highlight Vinylene Carbonate's role in enhancing pouch cell longevity under thermal stress, with reduced gas production (e.g., C₂H₄) during abuse conditions and improved performance in silicon-blended anodes.
Beyond graphite, Vinylene Carbonate supports SEI stabilization on silicon anodes, enabling high-capacity retention in full cells, and extends to sodium-ion batteries where it forms analogous protective layers.

For high-voltage nickel-manganese-cobalt (NMC) cathodes operating above 4.2 V, Vinylene Carbonate contributes to a cohesive cathode electrolyte interphase (CEI), mitigating surface reconstruction and capacity decay at ultrahigh potentials up to 5.2 V.

As a thermal additive, Vinylene Carbonate bolsters safety by passivating interfaces above 60 °C, reducing exothermic reactions in full cells.
In 2024, Vinylene Carbonate captured the largest market segment among battery electrolyte additives at 34.9% share, propelled by surging demand for electric vehicles requiring durable, high-performance cells.

KEY FEATURES of VINYLENE CARBONATE:
Vinylene Carbonate is a new type of film forming additive and overcharge protection additive for lithium-ion batteries.
Vinylene Carbonate can form a layer of solid electrolyte interface film (SEI film) by electrochemical reaction on the negative electrode surface during the initial charge and discharge of lithium-ion batteries, and effectively inhibit the embedding of solvent molecules.

Vinylene Carbonate has good performance at high and low temperature, and excellent anti-bloating function.
Vinyl carbonate can improve the capacity and cycle life of the lithium-ion battery.
In addition, Vinylene Carbonate can also be used as a monomer for the preparation of polyvinyl carbonate.

PROPERTIES of VINYLENE CARBONATE:
The vinylene carbonate (VC) is a cyclic, reactive, unsaturated carbonate ester.
The role of Vinylene Carbonate as an additive was studied and the solid electrolyte interfacial layer resulting from its reduction was characterized by infrared spectroscopy.

The best use of Vinylene Carbonate is, as a component of surface coatings.
Although there are reports on the additive characteristics of Vinylene Carbonate, as yet a scanty of study on the electrical properties of thin films obtained from VC has been appeared in the literature.

The vinylene compounds have applications in the electrical and optical devices.
So the investigations of the structural and electrical properties of thin films grown from Vinylene Carbonate are of necessity for its application in various devices.

From this point of view, the studies of the structural and electrical properties of plasma polymerized vinylene carbonate (PPVC) thin films have been undertaken.
In this paper, the structural characteristics by Fourier transform infrared (FTIR) analysis and the current density voltage (J–V) characteristics at different temperatures of the PPVC are presented.

INDUSTRIAL PROCESSES of VINYLENE CARBONATE:
Vinylene carbonate (VC) is primarily produced on an industrial scale through two main routes: catalytic dehydrogenation of ethylene carbonate and chlorination-dehydrochlorination of ethylene carbonate.
These processes are optimized for continuous operation and high throughput to meet demand as an electrolyte additive in lithium-ion batteries.

Building on laboratory methods for initial optimization, industrial production emphasizes scalability, yield enhancement, and minimization of by-products.
One established method involves the continuous vapor-phase dehydrogenation of ethylene carbonate over supported metal catalysts, such as zinc oxide-chromium oxide on alumina, ferric oxide on alumina, or silver on alumina, at temperatures of 200–550 °C, preferably 300–400 °C.

The process operates in a flow reactor with ethylene carbonate vapor passed over the catalyst bed at rates of 1–3 grams per milliliter of catalyst per hour, often with an inert diluent like nitrogen to facilitate separation of the product via distillation.
This one-step approach avoids chlorinated intermediates, enabling high-purity Vinylene Carbonate with substantial yields suitable for large-scale output.

The more commonly adopted industrial route is chlorination followed by dehydrochlorination.
Ethylene carbonate is first chlorinated, typically using chlorine gas under UV initiation at 60–70 °C, to form monochloroethylene carbonate, which is then dehydrochlorinated with a tertiary amine such as triethylamine.

To suppress side reactions like polymerization or decomposition, the dehydrochlorination is conducted in aromatic solvents like chlorobenzene or, more efficiently, in ethylene carbonate itself as the solvent, at 40–80 °C for 1–4 hours.
This yields crude VC at over 80% efficiency, with purified product exceeding 73% after vacuum distillation.

Patents highlight the use of such solvents to enhance selectivity and simplify purification, making the process economically viable for commercial production.
Recent advancements focus on greener variants of the dehydrochlorination step, employing amine-mediated elimination in minimal or solvent-free conditions to reduce environmental impact from harsh chlorinated solvents.

For instance, conducting the reaction in vinylene carbonate as the medium at 30–60 °C, with optional free radical scavengers, achieves yields of 73–74% while minimizing waste and side products.
Further optimizations, such as precise control of amine stoichiometry in organic solvents, have pushed crude yields above 95%, promoting sustainability in battery-grade Vinylene Carbonate manufacturing.

Global production of Vinylene Carbonate is geared toward its role as a battery electrolyte additive, with the market valued at approximately USD 0.23 billion in 2024 and projected to reach USD 0.84 billion by 2033, driven by rising demand for high-performance lithium-ion batteries.
Production primarily occurs in facilities in Asia and North America, emphasizing high-purity grades (>99%) for electrochemical applications.

A key challenge in Vinylene Carbonate production and handling is its propensity to polymerize under heat, light, or contamination, which can reduce yields and complicate downstream processing.
This is managed by incorporating stabilizers like butylated hydroxytoluene (BHT) at levels of 80–200 ppm during synthesis and storage, effectively inhibiting radical-initiated polymerization and ensuring product stability for industrial transport and use.

 
PREPARATION METHOD of VINYLENE CARBONATE:
The current methods for preparing Vinylene carbonate mainly involve the following steps:
Using vinyl carbonate as the raw material, introduce chlorine gas under ultraviolet light to undergo a substitution reaction and prepare vinyl chlorocarbonate.

In the presence of an organic solvent, react the vinyl chlorocarbonate obtained in step 1 with triethylamine to eliminate hydrogen chloride and generate Vinylene carbonate.

Distill and purify the mixture obtained in step 2.
The organic solvent mentioned in step 2 is dimethyl carbonate.

Vinylene carbonate is a cyclic carbonate with a five-membered ring and a C-C double bond within the ring.
Vinylene Carbonate has been shown to possess unique properties and can be added to aqueous electrolyte solutions to enhance their discharge capacity.

SYNTHESIS of VINYLENE CARBONATE:
Laboratory methods
Vinylene carbonate can be synthesized on a laboratory scale through the classic two-step process involving photochlorination of ethylene carbonate followed by dehydrochlorination.

This method, first reported in the early 1960s, remains a standard laboratory approach.
In the first step, ethylene carbonate undergoes selective photochlorination using chlorine gas under ultraviolet irradiation to form 4-chloro-1,3-dioxolan-2-one as the monochloro intermediate, typically conducted at 60–70°C in bulk or solvent-free conditions to minimize over-chlorination.

The reaction proceeds as follows:
(CH2O)2CO+Cl2−[hv](CH2O)(CHClO)CO+HCl
(CH2O)2CO+Cl2−>hv(CHClO)CO+HCl

Subsequently, the intermediate is treated with a base such as triethylamine in a solvent like dichloromethane or ethylene carbonate at 20–40°C to eliminate hydrogen chloride, yielding vinylene carbonate with overall efficiencies of 70–80%.
The dehydrochlorination step is represented by:
(CH2O)(CHClO)CO+Et3N−(CHCH)O2CO+Et3NH+Cl−
(CH2O)(CHClO)CO+Et3N−>(CH=CH)O2CO+Et3NH+Cl−

This method is widely adopted in research due to its straightforward setup and accessible reagents, though careful control of chlorination selectivity is essential to avoid dichloro by-products.
An alternative organocatalytic route enables the preparation of substituted vinylene carbonates directly from aromatic aldehydes and diphenyl carbonate.

This one-pot process involves an N-heterocyclic carbene (NHC)-catalyzed Benzoin condensation of the aldehyde to form an α-hydroxy ketone intermediate, followed by transcarbonation with diphenyl carbonate, using 4-dimethylaminopyridine (DMAP) as a co-catalyst at 90°C for 16 hours, affording yields of 20–99% depending on the aldehyde substituent.
The approach is particularly useful for accessing diversely functionalized analogs in small-scale syntheses without halogenated intermediates.

Purification of vinylene carbonate from reaction mixtures is achieved via distillation under reduced pressure (boiling point approximately 162°C at 760 mmHg, lower under vacuum) to isolate the product from salts and unreacted materials, followed by recrystallization from solvents like diethyl ether or ethyl acetate to attain high purity (>99%).
These techniques ensure the removal of impurities that could affect subsequent reactivity in research applications.

PROPERTIES of VINYLENE CARBONATE:
Vinylene carbonate is a colorless or slightly yellow transparent liquid.
Melting point of Vinylene Carbonate is 19-22 ℃, Boiling point: 162℃, Relative density (25℃): 1.355g/ml, Flash point: 73℃, Refractive index: 1.42-1.422, Water solubility: 11.5g/100ml.

CHEMICAL PROPERTIES of VINYLENE CARBONATE:
Vinylene carbonate features a molecular structure where a carbonate group is directly bonded to a vinylene group.
This configuration imparts unique chemical properties, including Vinylene Carbonate's reactivity and stability.
Vinylene Carbonate is known for undergoing polymerization and can participate in various chemical reactions such as esterification and polymerization.
Vinylene Carbonate's physical properties include a relatively low melting point and good solubility in organic solvents, which are beneficial for its use in different applications.

POLYMERIZATION AND MATERIALS of VINYLENE CARBONATE:
Vinylene carbonate (VC) serves as a reactive monomer in radical polymerization, yielding poly(vinylene carbonate) (PVC) with the repeating unit [–CH=CH–OCO₂–]ₙ, which forms the basis for solid polymer electrolytes (SPEs) in lithium-ion batteries.
This polymerization typically proceeds via free-radical initiation, such as with azobisisobutyronitrile (AIBN), in bulk or solution conditions above 40 °C, producing partially soluble, lightly colored polymers that exhibit good film-forming properties.

In battery applications, in-situ polymerization of Vinylene Carbonate with lithium salts creates flexible cross-linked networks directly within the cell, enhancing interfacial compatibility and enabling ionic conductivities on the order of 10⁻⁴ S/cm at room temperature.

Cross-linked PVC variants, particularly rigid-flexible composites incorporating garnet-type Li₆.₄Ga₀.₂La₃Zr₂O₁₂ (LLZO), have been developed for all-solid-state batteries, where the polymer matrix provides flexibility and the ceramic filler boosts mechanical strength and lithium-metal anode stability.

These poly(Vinylene Carbonate)-LLZO composites achieve ionic conductivities exceeding 10⁻⁴ S/cm while suppressing dendrite growth, supporting stable cycling over hundreds of cycles at moderate rates.
The in-situ reaction can be represented as:
Vinylene Carbonate+initiator (e.g., AIBN)+Li salt→cross-linked PVC-LLZO SPE

PVC-based materials exhibit a high dielectric constant (approximately 10–15) that facilitates lithium-ion dissociation and transport, alongside thermal stability up to 150 °C, making them suitable for elevated-temperature operation.
Recent advances include self-adaptive PVC electrolytes designed for high-temperature safety in solid-state lithium-metal batteries, maintaining performance above 100 °C without pressure buildup and enabling zero-strain cathodes through adaptive network restructuring.

Additionally, PVC integrated into polyacrylate blends has shown promise for high-voltage lithium-metal batteries, with enhanced interphase stability and capacity retention over 500 cycles at 4.5 V.
Commercially, PVC-derived electrolytes are emerging in solid-state battery prototypes, supported by patents such as CN105826603A for in-situ polymerized systems with improved compatibility.

ORGANIC SYNTHESIS of VINYLENE CARBONATE:
Vinylene carbonate was first synthesized and reported in 1953 by Newman and Addor via dehydrochlorination of chloroethylene carbonate, marking its initial exploration in organic chemistry.
Despite this early discovery, Vinylene Carbonate's applications in synthetic organic chemistry remain niche, with limited commercial production outside of battery-related uses due to the dominance of electrochemical demands.

A key role for vinylene carbonate in organic synthesis is as a dienophile in Diels-Alder reactions, where its electron-deficient C=C double bond reacts with dienes to form bicyclic carbonates.
These adducts serve as versatile intermediates for further derivatization, such as ring-opening or functional group manipulation to access complex polycyclic structures.

For instance, vinylene carbonate reacts with cyclopentadiene under thermal conditions (170–175°C) to yield the endo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol cyclic carbonate in 40–55% yield, with stereochemistry confirmed by NMR coupling constants (J = 14 Hz at 4.9 ppm).
Substituted analogs, such as 4-benzyloxymethyl-1,3-dioxol-2-one, similarly undergo cycloaddition with cyclopentadiene to produce endo-selective bicyclic products, highlighting the compound's utility in stereocontrolled synthesis.

IDENTITY AND PROPERTIES of VINYLENE CARBONATE:
Nomenclature and structure
Vinylene carbonate has the molecular formula C3H2O3C3H2O3.
Vinylene Carbonate is the simplest unsaturated cyclic carbonate, consisting of a five-membered 1,3-dioxol-2-one ring with a carbon-carbon double bond positioned between the two carbon atoms adjacent to the oxygen atoms.

The preferred IUPAC name for this compound is 2H-1,3-dioxol-2-one.
Other common names include vinylene carbonate (often abbreviated as VC) and 1,3-dioxolene-2-one.

Key identifiers for vinylene carbonate are the CAS Registry Number 872-36-6 and the EC Number 212-825-5, with a molar mass of 86.05 g/mol.
This molecule can be viewed as the cyclic ester of carbonic acid incorporating a vinylene (or vinylidene) group.
Vinylene carbonate serves as a dehydrogenated analog of ethylene carbonate.

PHYSICAL PROPERTIES of VINYLENE CARBONATE:
Vinylene carbonate is typically observed as a clear, colorless to light yellow liquid at room temperature.
Vinylene Carbonate has a melting point ranging from 19 to 22 °C and a boiling point of 162 °C, though it decomposes above approximately 160 °C.
The density of vinylene carbonate is 1.36 g/cm³ at 20 °C, with a refractive index of 1.421 (n20/D).

Vinylene carbonate exhibits solubility of approximately 11.5 g/100 mL in water and is miscible with common organic solvents such as acetone and ethanol.
To prevent unwanted polymerization, commercial preparations of vinylene carbonate are stabilized with butylated hydroxytoluene (BHT) at concentrations of 0.1% to 2%.
Vinylene Carbonate's flash point is 73 °C (closed cup).

CHEMICAL REACTIVITY of VINYLENE CARBONATE:
Vinylene carbonate exhibits high reactivity owing to its conjugated double bond adjacent to the carbonate carbonyl group, which activates the molecule toward cycloaddition and polymerization reactions.
As a dienophile, Vinylene Carbonate readily participates in Diels-Alder cycloadditions with various dienes, including cyclopentadiene, forming bicyclic adducts that can be further hydrolyzed to diols such as 7-oxabicyclo[2.2.1]hept-5-ene-2,3-diol derivatives.

This reactivity stems from the electron-deficient double bond, facilitating [4+2] cycloaddition under mild conditions.
Vinylene Carbonate undergoes radical polymerization, initiated by free radical sources, to yield poly(vinylene carbonate), a polymer featuring a 1,3-dioxolan-2-one ring integrated into the backbone.

The polymerization proceeds via addition across the double bond, represented approximately by:
nceC3H2O3→[−ceCH2−CH<O−C(=O)−O]n
where the < indicates the cyclic connection of -O-C(=O)-O- bridging the adjacent CH₂ and CH groups, with the repeating unit having the formula (C₃H₄O₃)n.

Bulk polymerization often results in crosslinked products due to chain transfer reactions, while solution polymerization in solvents like N,N-dimethylformamide produces soluble, lower-molecular-weight chains.

Vinylene carbonate is susceptible to hydrolysis and ring-opening in the presence of water or bases, particularly hydroxides, where it acts as a water scavenger by rapidly consuming impurities.
This base-driven process, with an activation energy lower than that of ethylene carbonate (~64 kJ/mol), leads to ring scission and formation of vinylene glycol-derived fragments (e.g., –CH₂O– and –CH(OR)₂ units) alongside CO₂ evolution, though polycarbonates may also form concurrently.

Electrochemical reduction of vinylene carbonate occurs at relatively low potentials, approximately 0.8 V vs. Li/Li⁺, initiating decomposition to generate solid electrolyte interphase (SEI) components such as polycarbonates on electrode surfaces.
Thermal decomposition begins at elevated temperatures above 80 °C, with significant breakdown between 150–500 °C yielding primarily CO₂ and ethylene oxide through surface-mediated pathways.

CHARACTERISTICS of VINYLENE CARBONATE:
Vinylene carbonate is usually produced as a yellow to brown liquid during industrial production.
Through suitable processing and purification steps, a solid melting at 20–22 °C with chlorine contents below 10 ppm can be obtained.
Liquid vinylene carbonate quickly turns yellow, even in the absence of light, and must be stabilized by adding radical scavengers.

In solid form, the high-purity substance, Vinylene Carbonate, is stable over long periods 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 for rechargeable lithium-ion batteries, such as dimethyl carbonate, diethyl carbonate, etc.

PREPARATION of VINYLENE CARBONATE:
Vinylene 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).

SYNTHESIS of VINYLENE CARBONATE:
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 METHODS of VINYLENE CARBONATE:
Purify Vinylene Carbonate by zone melting, or distillation, and stabilize it with 0.5% of 2,6-di-tert-butyl-p-cresol.

SYNTHESIS of VINYLENE CARBONATE:
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.

POLYMERISATION of VINYLENE CARBONATE:
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.

PROPERTIES of VINYLENE CARBONATE:
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 10 ppm can be obtained.

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.

PREPARATION of VINYLENE CARBONATE:
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.
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).

BENEFITS of VINYLENE CARBONATE:
*Enhancing Battery Performance: 
The incorporation of vinylene carbonate in lithium-ion batteries leads to better performance metrics, including higher capacity retention and extended cycle life.
The stable SEI layer formed by Vinylene Carbonate helps to prevent degradation of the electrode materials, leading to more reliable and longer-lasting batteries.

*Improving Polymer Properties: 
When used in polymerization, Vinylene Carbonate contributes to the creation of polymers with superior mechanical and chemical properties.
This can result in materials that are more durable and resistant to environmental factors, which is crucial for many industrial applications.

ADVANTAGES IN CHEMICAL REACTIONS of VINYLENE CARBONATE:
Vinylene Carbonate’s unique chemical properties allow it to participate in a range of reactions, offering flexibility in organic synthesis.
Its ability to form stable intermediates and final products makes Vinylene Carbonate a valuable compound in the development of new chemical processes and products.

*Synthesis of cis-4,5-Dihydroxy-1,2-cyclohexene
When cyclopentadiene is used as the diene, the vicinal norbornene diol bicyclo[2.2.1]hept-5-ene-2,3-diol is formed after hydrolysis.
The Swern oxidation to the 1,2-ketone bicyclo[2.2.1]hept-5-ene-2,3-dione proceeds with a yield of 73%.

*Synthesis of norbornenedione
Under UV irradiation, ketones react with vinylene carbonate to form bicyclic exo-oxetanes.

*VC addition to ketones
With phosphorus(V) sulfide, vinylene carbonate reacts to the corresponding vinylenethionocarbonate (2-thiono-1,3-dioxol-4-ene), which gives ketene in quantitative yield upon UV irradiation.
The reaction is a good alternative to the decomposition of α-diazoketones.

VINYLENE CARBONATE: REACTIVITY, POLYMERIZATION BEHAVIOR, AND THE LIMITS OF ITS POLYMER-BASED MATERIALS:
Already in the first publication on vinylene carbonate Diels-Alder reactions were described using the example of the addition to 2,3-dimethylbutadiene to form the bicyclic carbonate and subsequent hydrolysis to form cis-4,5-dihydroxy-1,2-cyclohexene.

CIS-4,5-DIHYDROXY-1,2-CYCLOHEXENE SYNTHESIS
With cyclopentadiene as the diene, hydrolysis yields the vicinal norbornenediol bicyclo[2.2.1]hept-5-ene-2,3-diol.
The Swern oxidation to the 1,2-ketone bicyclo[2.2.1]hept-5-ene-2,3-dione proceeds in the variant with trifluoroacetic anhydride instead of oxalyl chloride in a yield of 73% of theory.

NORBORNENEDIONE
Under UV irradiation, ketones react with vinylene carbonate to form bicyclic exo-oxetanes.

VINYLENE CARBONATE ADDITION TO KETONES
Vinylene carbonate reacts with phosphorus(V) sulfide to give the corresponding vinylenethionocarbonate (2-thiono-1,3-dioxol-4-ene) which, upon UV irradiation, yields ketene in quantitative yield.
The reaction represents a good alternative to the decomposition of α-diazoketones.

CHAINS MADE OF VINYL CARBONATE
Vinylene carbonate is used more extensively as an electrolyte additive for lithium-ion batteries, where it promotes the formation of a solid electrolyte interphase (SEI), an insoluble film forming a solid interface between the negative electrode and the electrolyte.
This polymer film enables ionic conduction but prevents electrolyte reduction at the negative (graphite) electrode and contributes significantly to the long-term stability of lithium-ion batteries.
Recent publications suggest that the cyclic sultone 3-fluoro-1,3-propanesultone (FPS) has superior properties to vinylene carbonate as an SEI former.

3-Fluoro-1,3-propanesultone
Since the 1,3-propanesultone underlying FPS is classified as a particularly dangerous carcinogenic substance, a considerable hazard potential must also be assumed for FPS.

Polymers
The very first paper on vinylene carbonate describes the bulk polymerization to colorless polymers that were water-soluble after hydrolysis.
Later publications suggest that the first authors had only prepared oligomers with low molar mass.
The purity of the monomeric vinylene carbonate is crucial for the production of polymers with higher molar mass and useful properties.
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, or copolymerized with other vinyl monomers such as vinylpyrrolidone or vinyl propionate.

POLYMERIZATION OF VINYLENE CARBONATE:
Polyvinyl carbonate is readily soluble in acetone and dimethylformamide.
However, the resulting solutions tend to decompose even at room temperature.
Patent literature describes tensile-strength fibers, clear, colorless, and mechanically robust films, membranes for reverse osmosis, and supports for affinity chromatography made of polyvinyl carbonate.

Besides its instability in solutions, the hydrolysis tendency of polyvinyl carbonate is problematic even in weakly alkaline environments.
This process involves the cleavage of the cyclic carbonate ring to form polyhydroxymethylene (PHM) with the repeating unit –(CHOH)–, whose behavior is much more similar to cellulose than to the related polyvinyl alcohol with the repeating unit –(CH₂-CHOH)–.

HYDROLYSIS OF POLYVINYL CARBONATE TO POLYHYDROXYMETHYLENE:
Polyhydroxymethylene films, obtained by alkaline hydrolysis of polyvinyl carbonate films using sodium methoxide in methanol, are crystalline and exhibit high tensile strength.
Similar to cellulose, polyhydroxymethylene can be dissolved in hot sodium hydroxide solution and, by crosslinking, converted into a highly swellable polymer that can absorb up to 10,000 times its weight in water.
Polyhydroxymethylene is soluble in anhydrous hydrazine and can be spun into cellulose-like fibers in water.

Similar to cellulose, polyhydroxymethylene reacts with carbon disulfide in alkaline solutions to form a xanthate, which can be precipitated in dilute sulfuric acid to yield water-insoluble polyhydroxymethylene.
The lack of recent literature, especially patent literature, on poly-Vinylene Carbonate and PHM suggests that the properties of the obtained homo- and copolymers and the molded parts produced from them could not meet the expectations set therein.

PHYSICAL and CHEMICAL PROPERTIES of VINYLENE CARBONATE:
Chemical Formula:C3H2O3
Molar Mass:86.05 g/mol
Appearance:Colourless liquid
Density:1.35
Melting Point:22 °C
Boiling Point:178 °C
CAS:872-36-6
EC Number:212-825-5
XLogP3:0.3
Hydrogen Bond Donor Count:0

Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:0
Exact Mass:86.000393922 Da
Monoisotopic Mass:86.000393922 Da
Topological Polar Surface Area:35.5 Ų
Heavy Atom Count:6
Formal Charge:0
Complexity:84.2
Isotope Atom Count:0
Defined Atom Stereocenter Count:0

Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Physical State:Liquid
Storage Temperature:Refrigerated (0-10°C)
Store Under Inert Gas:Store under inert gas
Condition to Avoid:Moisture Sensitive,Heat Sensitive
Reaxys Registry Number:105683

PubChem Substance ID:87577815
MDL Number:MFCD00005380
Empirical Formula:C3H2O3
Color:Light yellow
Odor:No data available
Melting Point:15 °C
Boiling Point:168 °C
Flash Point:80 °C
Autoignition Temperature:355 °C
Water Solubility:515 g/l at 20.2 °C
Log Pow:-0.36 at 20 °C

Density:1.4 g/cm3
Oxidizing Properties:none
Surface Tension:73.4 mN/m at 19.9 °C
CBNumber:CB9119200
Molecular Formula:C3H2O3
Molecular Weight:86.05
MDL Number:MFCD00005380
MOL File:872-36-6.mol
Melting Point:19-22 °C
Boiling Point:162 °C
Density:1.360 g/mL at 20 °C

Vapor Pressure:3.35 hPa at 25 °C
Refractive Index:n20/D 1.421
Flash Point:163 °F
Storage Temp:2-8°C
Solubility:11.5 g/100 mL
Form:Liquid
Specific Gravity:1.355
Color:Colorless to pale yellow
Water Solubility:11.5 g/100 mL
Sensitive:Moisture Sensitive
BRN:105683

InChI:1S/C3H2O3/c4-3-5-1-2-6-3/h1-2H
InChIKey:VAYTZRYEBVHVLE-UHFFFAOYSA-N
SMILES:O=C1OC=CO1
LogP:-0.36 at 20℃
CAS DataBase Reference:872-36-6
EWG's Food Scores:1
FDA UNII:1X0ZZF9WFV
NIST Chemistry Reference:1,3-Dioxol-2-one
EPA Substance Registry System:1,3-Dioxol-2-one
UNSPSC Code:26111700
NACRES:NA.23

CAS:872-36-6
IUPAC Name:2H-1,3-dioxol-2-one
Molecular Formula:C3H2O3
Molecular Weight:86.05
Synonym:1,3-dioxol-2-one
Appearance:White to pale yellow
Assay from Supplier's CofA:≥97.0%
Stabilizer:BHT <2%
Form:Fused or crystalline low melting solid
Product Name:Vinylene Carbonate

Chemical Formula:C3H2O3
Synonym(s):1,3-Dioxol-2-one, Vinyl Carbonate, Carbonic Acid, Cyclic Vinylene Ester
SKU#:CM1041: 100g
Molecular Weight:86.05 g/mol
Appearance:Colorless and transparent liquid
Purity:99.98%
Degree of Solubility in Water:515 g/L at 20 °C
Melting Point:15-22 °C
Flash Point:80 °C
Boiling Point:168 °C
Density:1.36 g/mL at 25 °C
Vapor Pressure:335 Pa at 24 °C
Storage Condition:0-10 °C

FIRST AID MEASURES of VINYLENE CARBONATE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of VINYLENE CARBONATE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of VINYLENE CARBONATE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of VINYLENE CARBONATE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of VINYLENE CARBONATE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of VINYLENE CARBONATE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available