Ethylene carbonate

Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid.[2]

Ethylene carbonate
Skeletal formula of ethylene carbonate
Ball-and-stick model of the ethylene carbonate molecule
Names
IUPAC name
1,3-dioxolan-2-one
Other names
ethylene glycol carbonate[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.283
Properties
C3H4O3
Molar mass 88.062 g·mol−1
Appearance White to yellow solid
Density 1.3210 g/cm3
Melting point 34 to 37 °C (93 to 99 °F; 307 to 310 K)
Boiling point 243.0 °C (469.4 °F; 516.1 K)
Soluble
Hazards
Safety data sheet External MSDS
Irritant (XI)
R-phrases (outdated) R41
S-phrases (outdated) S26 S39
Flash point 150 °C (302 °F; 423 K)
465 °C (869 °F; 738 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Production and reactions

Ethylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide. The reaction is catalyzed by a variety of cations and complexes:[3]

(CH2)2O + CO2 → (CH2O)2CO

Ethylene carbonate can also be produced from the reaction of urea and ethylene glycol using zinc oxide as a catalyst at a temperature of 150 °C and a pressure of 3 kPa:[4]

(NH2)2CO + HO−CH2CH2−OH → (CH2O)2CO + 2 NH3

Ethylene carbonate (and propylene carbonate) may be converted to dimethyl carbonate (a useful solvent and a mild methylating agent) via transesterification by methanol:

C2H4CO3 + 2 CH3OH → CH3OCO2CH3 + HOC2H4OH

Dimethyl carbonate may itself be similarly transesterified to diphenyl carbonate, a phosgene-substitute:[3]

CH3OCO2CH3 + 2 PhOH → PhOCO2Ph + 2 MeOH

Applications

Ethylene carbonate is used as a polar solvent with a molecular dipole moment of 4.9 D,[5][6] only 0.1 D lower than that of propylene carbonate.

It can be used as a high permittivity component of electrolytes in lithium batteries and lithium-ion batteries. Other components like diethyl carbonate, ethyl methyl carbonate, dimethyl carbonate and methyl acetate can be added to those electrolytes in order to decrease the viscosity and melting point.[7]

Ethylene carbonate is also used as plasticizer, and as a precursor to vinylene carbonate, which is used in polymers and in organic synthesis.

See also

External links

References

  1. ^ "CID 7303 -- PubChem Compound Summary". pubchem.ncbi.nlm.nih.gov. Retrieved 2008-03-15.
  2. ^ JEFFSOL ETHYLENE CARBONATE catalog entry at www.huntsman.com. Accessed on 2010-02-18.
  3. ^ a b Hans-Josef Buysch. "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197.
  4. ^ Bhalchandra M. Bhanage; Shin-ichiro Fujita (2003). "Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis". Green Chemistry. 5 (4): 429–432. doi:10.1039/b304182d.
  5. ^ Ralph P. Seward; Ernest C. Vieira (1958). "The Dielectric Constants of Ethylene Carbonate and of Solutions of Ethylene Carbonate in Water, Methanol, Benzene and Propylene Carbonate". J. Phys. Chem. 62 (1): 127–128. doi:10.1021/j150559a041.
  6. ^ Richard Payne; Ignatius E. Theodorou (1972). "Dielectric properties and relaxation in ethylene carbonate and propylene carbonate". J. Phys. Chem. 76 (20): 2892–2900. doi:10.1021/j100664a019.
  7. ^ E. R. Logan; J. R. Dahn (2018). "A Study of the Physical Properties of Li-Ion Battery Electrolytes Containing Esters". J. Electrochem. Soc. 165 (2): A21–A30. doi:10.1149/2.0271802jes.
Butylene carbonate

Butylene carbonate usually refers to 1,2-Butylene carbonate, but it may also refer to:

cis-2,3-Butylene carbonate

trans-2,3-Butylene carbonate

C3H4O3

The molecular formula C3H4O3 may refer to:

Acetic formic anhydride

Ethylene carbonate

Glucic acid

Glycidic acid

Pyruvic acid

Carbonate

In chemistry, a carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula of CO2−3. The name may also refer to a carbonate ester, an organic compound containing the carbonate group C(=O)(O–)2.

The term is also used as a verb, to describe carbonation: the process of raising the concentrations of carbonate and bicarbonate ions in water to produce carbonated water and other carbonated beverages – either by the addition of carbon dioxide gas under pressure, or by dissolving carbonate or bicarbonate salts into the water.

In geology and mineralogy, the term "carbonate" can refer both to carbonate minerals and carbonate rock (which is made of chiefly carbonate minerals), and both are dominated by the carbonate ion, CO2−3. Carbonate minerals are extremely varied and ubiquitous in chemically precipitated sedimentary rock. The most common are calcite or calcium carbonate, CaCO3, the chief constituent of limestone (as well as the main component of mollusc shells and coral skeletons); dolomite, a calcium-magnesium carbonate CaMg(CO3)2; and siderite, or iron(II) carbonate, FeCO3, an important iron ore. Sodium carbonate ("soda" or "natron") and potassium carbonate ("potash") have been used since antiquity for cleaning and preservation, as well as for the manufacture of glass. Carbonates are widely used in industry, e.g. in iron smelting, as a raw material for Portland cement and lime manufacture, in the composition of ceramic glazes, and more.

Carbonate ester

A carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R1O(C=O)OR2 and they are related to esters R1O(C=O)R and ethers R1OR2 and also to the inorganic carbonates.

Monomers of polycarbonate (e.g. Lexan) are linked by carbonate groups. These polycarbonates are used in eyeglass lenses, compact discs, and bulletproof glass. Small carbonate esters like dimethyl carbonate, ethylene carbonate, propylene carbonate are used as solvents. Dimethyl carbonate is also a mild methylating agent.

Carbon–oxygen bond

A carbon–oxygen bond is a polar covalent bond between carbon and oxygen. Oxygen has 6 valence electrons and prefers to either share two electrons in bonding with carbon, leaving the 4 nonbonding electrons in 2 lone pairs :O: or to share two pairs of electrons to form the carbonyl functional group. =O: Simple representatives of these two bond types are the _OH in alcohols such as the ethanol in beverages and fuels and the C=O in ketones (as well as many other related carbonyl compounds).

Diethyl carbonate

Diethyl carbonate (sometimes abbreviated DEC) is a carbonate ester of carbonic acid and ethanol with the formula OC(OCH2CH3)2. At room temperature (25 °C) diethyl carbonate is a clear liquid with a low flash point.

Diethyl carbonate is used as a solvent such as in erythromycin intramuscular injections. It can be used as a component of electrolytes in lithium batteries. It has been proposed as a fuel additive to support cleaner diesel fuel combustion because its high boiling point might reduce blended fuels' volatility, minimize vapor buildup in warm weather that can block fuel lines.

Dual carbon battery

A dual carbon battery is one that uses carbon for both the cathode and the anode.

Episulfide

Episulfides are a class of organic compounds that contain a saturated heterocyclic ring consisting of two carbon atoms and one sulfur atom. It is the sulfur analogue of an epoxide or aziridine. They are also known as thiiranes, olefin sulfides, thioalkylene oxides, and thiacyclopropanes. Episulfides are less common and generally less stable than epoxides. The most common derivative is ethylene sulfide (C2H4S).

Ethylene oxide

Ethylene oxide, called oxirane by IUPAC, is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

The reactivity that is responsible for many of ethylene oxide's hazards also make it useful. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used for making many consumer products as well as non-consumer chemicals and intermediates. These products include detergents, thickeners, solvents, plastics, and various organic chemicals such as ethylene glycol, ethanolamines, simple and complex glycols, polyglycol ethers, and other compounds. Although it is a vital raw material with diverse applications, including the manufacture of products like polysorbate 20 and polyethylene glycol (PEG) that are often more effective and less toxic than alternative materials, ethylene oxide itself is a very hazardous substance. At room temperature it is a flammable, carcinogenic, mutagenic, irritating, and anaesthetic gas.As a toxic gas that leaves no residue on items it contacts, ethylene oxide is a surface disinfectant that is widely used in hospitals and the medical equipment industry to replace steam in the sterilization of heat-sensitive tools and equipment, such as disposable plastic syringes. It is so flammable and extremely explosive that it is used as a main component of thermobaric weapons; therefore, it is commonly handled and shipped as a refrigerated liquid to control its hazardous nature.

Lithium-ion battery

A lithium-ion battery or Li-ion battery (abbreviated as LIB) is a type of rechargeable battery. Lithium-ion batteries are commonly used for portable electronics and electric vehicles and are growing in popularity for military and aerospace applications. The technology was largely developed by John Goodenough, Stanley Whittingham, Rachid Yazami and Akira Yoshino during the 1970s–1980s, and then commercialized by a Sony and Asahi Kasei team led by Yoshio Nishi in 1991.

In the batteries lithium ions move from the negative electrode through an electrolyte to the positive electrode during discharge, and back when charging. Li-ion batteries use an intercalated lithium compound as the material at the positive electrode and typically graphite at the negative electrode.

The batteries have a high energy density, no memory effect (other than LFP cells) and low self-discharge. They can however be a safety hazard since they contain a flammable electrolyte, and if damaged or incorrectly charged can lead to explosions and fires. Samsung were forced to recall Galaxy Note 7 handsets following lithium-ion fires, and there have been several incidents involving batteries on Boeing 787s.

Chemistry, performance, cost and safety characteristics vary across LIB types. Handheld electronics mostly use lithium polymer batteries (with a polymer gel as electrolyte) with lithium cobalt oxide (LiCoO2) as cathode material, which offers high energy density but presents safety risks, especially when damaged. Lithium iron phosphate (LiFePO4), lithium ion manganese oxide battery (LiMn2O4, Li2MnO3, or LMO), and lithium nickel manganese cobalt oxide (LiNiMnCoO2 or NMC) offer lower energy density but longer lives and less likelihood of fire or explosion. Such batteries are widely used for electric tools, medical equipment, and other roles. NMC in particular is a leading contender for automotive applications.

Research areas for lithium-ion batteries include life extension, energy density, safety, cost reduction, and charging speed, among others. Research has been under way in the area of non-flammable electrolytes as a pathway to increased safety based on the flammability and volatility of the organic solvents used in the typical electrolyte. Strategies include aqueous lithium-ion batteries, ceramic solid electrolytes, polymer electrolytes, ionic liquids, and heavily fluorinated systems.

Lithium hexafluorophosphate

Lithium hexafluorophosphate is an inorganic compound with the formula LiPF6. It is a white crystalline powder. It is used in commercial secondary batteries, an application that exploits its high solubility in non aqueous, polar solvents. Specifically, solutions of lithium hexafluorophosphate in carbonate blends of ethylene carbonate, dimethyl carbonate, diethyl carbonate and/or ethyl methyl carbonate, with a small amount of one or many additives like vinylene carbonate, serve as state-of-the-art electrolytes in lithium-ion batteries. This application also exploits the inertness of the hexafluorophosphate anion toward strong reducing agents, such as lithium metal.

The salt is relatively stable thermally, but loses 50% weight at 200 °C (392 °F). It hydrolyzes near 70 °C (158 °F) according to the following equation:

LiPF6 + H2O → HF + PF5 + LiOHOwing to the Lewis acidity of the Li+ ions, LiPF6 also catalyses the tetrahydropyranylation of tertiary alcohols.In lithium-ion batteries, LiPF6 reacts with Li2CO3 in the following way, which could be catalysed by small amounts of HF:

LiPF6 + Li2CO3 → POF3 + CO2 + 3 LiFA recent research also proposed, based on nuclear magnetic resonance results and density functional theory calculations, that LiPF6 could react in a mixture of ethylene carbonate and dimethyl carbonate with alumina powder or alumina coated lithium-ion batteries cathode materials to form lithium difluorophosphate and alumina oxyfluoride via the reaction:

2 Al2O3 (s) + x LiPF6 (solv) → 2 Al2O3-xF2x (s) + x LiPO2F2 (solv)Since lithium difluorophosphate is known to improve the performance of lithium-ion batteries, this suggest a new mechanism of action for alumina coatings in lithium-ion batteries.

OMEGA process

The OMEGA process ("Only MEG Advantage") is a process by Shell Global Solutions that is used to produce ethylene glycol from ethylene. This process comprises two steps, the controlled oxidation of ethylene to ethylene oxide, and the net hydrolysis of ethylene oxide to monoethylene glycol (MEG). The first chemical plant using the OMEGA process was started in South Korea. Subsequent OMEGA plants have been started in Saudi Arabia and Singapore. Shell claims that this process, compared to conventional ones, does not produce higher glycols, uses less steam and water, and generates less waste.

Potassium thiocyanate

Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides. The compound has a low melting point relative to most other inorganic salts.

Tetraethylammonium chloride

Tetraethylammonium chloride (TEAC) is a quaternary ammonium compound with the chemical formula C8H20N+Cl−, sometimes written as Et4N+Cl−. In appearance, it is a hygroscopic, colorless, crystalline solid. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.

Tetraethylammonium iodide

Tetraethylammonium iodide is a quaternary ammonium compound with the chemical formula C8H20N+I−. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.

Thiirane

Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S. It is the smallest sulfur-containing heterocycle and the simplest episulfide. Like many organosulfur compounds, this species has a stench. Thiirane is also used to describe any derivative of the parent ethylene sulfide.

Vidarabine

Vidarabine or 9-β-D-arabinofuranosyladenine (ara-A) is an antiviral drug which is active against herpes simplex and varicella zoster viruses.

Vinylene carbonate

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.

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