Buy Quality Vinylene carbonate (872-36-6) from LEAPChem
Nov. 2019/1/24 14:31:33 By LEAP Chem
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Basic Information of Vinylene carbonate
Chemical Name: Vinylene carbonate
Cas No.: 872-36-6
Molecular Formula: C3H2O3
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. In the second stage, monochlorethylene is converted in a dehydrochlorination reaction (e.g. with triethylamine) at 40-60 °C into vinylene carbonate. The reaction mixture can optionally be diluted with ethylene carbonate, vinylene carbonate or methyl tert-butyl ether.
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 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. In there, it promotes the formation of a film insoluble in the electrolyte as a solid interface between the negative electrode and the electrolyte (SEI, solid electrolyte interphase). 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. Recent publications suggest that the cyclic sultone 3-fluoro-1,3-propanesultone (FPS) is compared to vinylene carbonate superior in the SEI formation.
Already the first work on vinylene carbonate describes its bulk polymerization a colorless polymer, which is water soluble after hydrolysis. 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 monomeric vinylene carbonate. 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. It can also be copolymerized with other vinyl monomers such as vinyl pyrrolidone or vinyl propionate.
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