propylene carbonate
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Propylene carbonate (often abbreviated PC) is an
organic compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of atoms, molecules and ions: their composition, structure, ...
with the formula C4H6O3. It is a cyclic
carbonate ester A carbonate ester (organic carbonate or organocarbonate) is an ester An ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the s ...

carbonate ester
derived from
propylene glycol Propylene glycol ( IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula A chemical formula is a way of presenting information about the chemical pro ...
. This colorless and odorless liquid is useful as a
polar Polar may refer to: Geography Polar may refer to: * Geographical pole, either of two fixed points on the surface of a rotating body or planet, at 90 degrees from the equator, based on the axis around which a body rotates *Polar climate, the clim ...
,
aprotic solventA protic solvent is a solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a ...
. Propylene carbonate is
chiral that is chiral Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand," a familiar chiral object. An object or a system is ''chiral'' if it is disting ...
, but is used as the
racemic mixture In chemistry, a racemic mixture, or racemate (), is one that has equal Amount of substance, amounts of left- and right-handed enantiomers of a Chirality (chemistry), chiral molecule. The first known racemic mixture was racemic acid, which Louis Past ...
in most contexts.


Preparation

Although many organic carbonates are produced using
phosgene Phosgene is the organic chemical compound with the formula In science Science (from the Latin word ''scientia'', meaning "knowledge") is a systematic enterprise that Scientific method, builds and Taxonomy (general), organizes knowledge ...

phosgene
, propylene and ethylene carbonates are exceptions. They are mainly prepared by the
carbonation Carbonation is the chemical reaction of carbon dioxide to give carbonates, bicarbonates, and carbonic acid. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds com ...
of the
epoxide An epoxide is a cyclic ether Ethers are a class of organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to ...

epoxide
s (epoxypropane, or
propylene oxide Propylene oxide is an organic compound with the molecular formula CH3CHCH2O. This colourless volatility (chemistry), volatile liquid with an odour resembling ether, is produced on a large scale industrially. Its major application is its use for the ...

propylene oxide
here): :CH3CHCH2O + CO2 → CH3C2H3O2CO The process is particularly attractive since the production of these epoxides consumes carbon dioxide. Thus this reaction is a good example of a green process. The corresponding reaction of
1,2-propanediol Propylene glycol (IUPAC nomenclature, IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. Containing two alcohol groups, it is classe ...
with phosgene is complex, yielding not only propylene carbonate but also oligomeric products. Propylene carbonate can also be synthesized from
urea Urea, also known as carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amidogen, –NH2 groups joined by a carbonyl (C=O) functional group. Urea serves an important role in the metabolism of nitrogen-containing ...

urea
and
propylene glycol Propylene glycol ( IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula A chemical formula is a way of presenting information about the chemical pro ...
over .


Applications


As a solvent

Propylene carbonate is used as a polar,
aproticA polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine groups. These solvents do not serve as proton donors in hydrogen bonding, although they can be proton acceptors. Many solvents, inc ...
solvent. It has a high
molecular dipole moment In electromagnetism Electromagnetism is a branch of physics involving the study of the electromagnetic force, a type of physical interaction that occurs between electric charge, electrically charged particles. The electromagnetic force is c ...
(4.9 D), considerably higher than those of
acetone Acetone, or propanone, is an organic compound with the chemical formula, formula (methyl group, CH3)2carbonyl, CO. It is the simplest and smallest ketone. It is a colourless, highly volatile and flammable liquid with a characteristic pungent odo ...
(2.91 D) and
ethyl acetate Ethyl acetate ( systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carb ...

ethyl acetate
(1.78 D). It is possible, for example, to obtain
potassium Potassium is a chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance consisting only of atoms that all have the same ...

potassium
,
sodium Sodium is a chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table of the chemical elements In chemistry, an element is a pure substance consisting only of atoms that all have the same num ...

sodium
, and other
alkali metal The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names f ...
s by
electrolysis In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds composed of atoms ...

electrolysis
of their
chloride The chloride ion is the anion An ion () is a particle, atom or molecule with a net electric charge, electrical charge. The charge of the electron is considered negative by convention. The negative charge of an ion is equal and opposite ...

chloride
s and other salts dissolved in propylene carbonate. Due to its high
dielectric constant The dielectric constant (or relative permittivity) is the permittivity, electric permeability of a material expressed as a ratio with the vacuum permittivity, electric permeability of a vacuum. A dielectric is an insulating material, and the diele ...
of 64, it is frequently used as a high-
permittivity In electromagnetism Electromagnetism is a branch of physics involving the study of the electromagnetic force, a type of physical interaction that occurs between electric charge, electrically charged particles. The electromagnetic force is car ...
component of
electrolyte An electrolyte is a medium containing ions that is conductivity (electrolytic), electrically conducting through the movement of ions, but not conducting Electron, electrons. This includes most soluble Salt (chemistry), salts, acids, and Base (chemi ...
s in
lithium batteries Lithium batteries are Primary Cell, primary Battery (electricity), batteries that have metallic lithium as an anode. These types of batteries are also referred to as lithium-metal batteries. They stand apart from other batteries in their high c ...

lithium batteries
, usually together with a low-viscosity solvent (e.g.
dimethoxyethane Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aproticA polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents la ...

dimethoxyethane
). Its high polarity allows it to create an effective
solvation Solvation (or dissolution) describes the interaction of solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usuall ...

solvation
shell around lithium ions, thereby creating a conductive
electrolyte An electrolyte is a medium containing ions that is conductivity (electrolytic), electrically conducting through the movement of ions, but not conducting Electron, electrons. This includes most soluble Salt (chemistry), salts, acids, and Base (chemi ...
. However, it is not used in
lithium-ion batteries A lithium-ion battery or Li-ion battery is a type of rechargeable battery A rechargeable battery, storage battery, or secondary cell, (or archaically accumulator) is a type of electrical battery which can be charged, discharged into a load ...
due to its destructive effect on
graphite Graphite (), archaically referred to as plumbago, is a crystalline form of the element carbon Carbon (from la, carbo "coal") is a chemical element Image:Simple Periodic Table Chart-blocks.svg, 400px, Periodic table, The periodic table ...
. Propylene carbonate can also be found in some
adhesive adhesive dispensed from a tube Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that molecular binding , binds them together and resists their separat ...
s,
paint stripper Paint stripper, or paint remover, is a chemical product designed to remove paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is ...
s, and in cosmetics. It is also used as plasticizer. Propylene carbonate is also used as a solvent for removal of CO2 from natural gas and synthesis gas where H2S is not also present. This use was developed by El Paso Natural Gas Company and Fluor Corporation in the 1950s for use at the Terrell County Gas Plant in West Texas, now owned by Occidental Petroleum.


Other

Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification).. In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging. In Grignard reaction propylene carbonate (or most other carbonate esters) might be used to create tertiary alcohols.


Safety

Clinical studies indicate that propylene carbonate does not cause skin irritation or sensitization when used in cosmetic preparations, whereas moderate skin irritation is observed when used undiluted. No significant toxic effects were observed in rats fed propylene carbonate, exposed to the vapor, or exposed to the undiluted liquid. In the US, propylene carbonate is not regulated as a volatile organic compound (VOC) because it does not contribute significantly to the formation of smog and because its vapor is not known or suspected to cause cancer or other toxic effects.


See also

* Ethylene carbonate * Trimethylene carbonate


References

{{Authority control Ester solvents Plasticizers Carbonate esters