Propylene carbonate

Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol.[3] This colorless and odorless liquid is useful as a polar, aprotic solvent.[4] Propylene carbonate is chiral, but is used exclusively as the racemic mixture in most contexts.

Propylene carbonate[1][2]
Propylene Carbonate V.1
Propylene-carbonate-3D-vdW
Sample of propylene carbonate
Names
IUPAC name
4-Methyl-1,3-dioxolan-2-one
Other names
(R,S)-4-Methyl-1,3-dioxolan-2-one
Cyclic propylene carbonate
Carbonic acid propylene ester
Cyclic 1,2-propylene carbonate
Propylene glycol cyclic carbonate
1,2-Propanediol carbonate
4-Methyl-2-oxo-1,3-dioxolane
Arconate 5000
Texacar PC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.248
UNII
Properties
C4H6O3
Molar mass 102.089 g·mol−1
Appearance Colorless liquid
Density 1.205 g/cm3
Melting point −48.8 °C (−55.8 °F; 224.3 K)
Boiling point 242 °C (468 °F; 515 K)
Very soluble (240 g/L at 20°C)
1.4189
Hazards
Main hazards Xi
Safety data sheet MSDS by Mallinckrodt Baker
R-phrases (outdated) R36
S-phrases (outdated) S26 S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
1
1
Flash point 132 °C (270 °F; 405 K)
455 °C (851 °F; 728 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Preparation

Although many organic carbonates are produced using phosgene, propylene and ethylene carbonates are exceptions. They are mainly prepared by the carbonation of the epoxides[4] (epoxypropane, or 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 with phosgene is complex, yielding not only propylene carbonate but also oligomeric products.

Propylene carbonate can also be synthesized from urea and propylene glycol over zinc acetate.[5]

Applications

As a solvent

Propylene carbonate is used as a polar, aprotic solvent.[6] It has a high molecular dipole moment (4.9 D), considerably higher than those of acetone (2.91 D) and ethyl acetate (1.78 D).[1] It is possible, for example, to obtain potassium, sodium, and other alkali metals by electrolysis of their chlorides and other salts dissolved in propylene carbonate.[7]

Due to its high dielectric constant of 64, it is frequently used as a high-permittivity component of electrolytes in lithium batteries, usually together with a low-viscosity solvent (e.g. dimethoxyethane). Its high polarity allows it to create an effective solvation shell around lithium ions, thereby creating a conductive electrolyte. However, it is not used in lithium-ion batteries due to its destructive effect on graphite.[8]

Propylene carbonate can also be found in some adhesives, paint strippers, and in cosmetics.[9] 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.[10]

Other

Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification).[4]

In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging.[11]

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.[12] 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.[13]

See also

References

  1. ^ a b Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. ISBN 1439855110.
  2. ^ Propylene carbonate at Sigma-Aldrich.
  3. ^ WebBook page for propylene carbonate.
  4. ^ a b c Hans-Josef Buysch. "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197..
  5. ^ Synthesis of propylene carbonate from urea http://pubs.acs.org/doi/abs/10.1021/ie049948i
  6. ^ Dieter Stoye. "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437..
  7. ^ J. Jorné; C. W. Tobias (1975). "Electrodeposition of the alkali metals from propylene carbonate". J. Appl. Electrochem. 5 (4): 279–290. doi:10.1007/BF00608791.
  8. ^ Doron Aurbach (1999). Nonaqueous Electrochemistry. CRC Press. ISBN 978-0824773342.
  9. ^ Record in the Household Products Database of NLM.
  10. ^ Schendel, R. "Comparison of Fluor Solvent and Selexol Processes" (PDF). Retrieved 4 April 2016.
  11. ^ Teo C. A., Donald W. A. (May 2014). "Solution additives for supercharging proteins beyond the theoretical maximum proton-transfer limit in electrospray ionization mass spectrometry". Anal. Chem. 86 (9): 4455–62. doi:10.1021/ac500304r. PMID 24712886.
  12. ^ "Environmental Profile for Propylene Carbonate". U.S. Environmental Protection Agency. 1998.
  13. ^ Johnson, William L. "REVISION TO DEFINITION OF VOLATILE ORGANIC COMPOUNDS - EXCLUSION OF PROPYLENE CARBONATE AND DIMETHYL CARBONATE". US Environmental Protection Agency. US EPA. Retrieved 11 July 2015.
1,2-Butylene carbonate

1,2-Butylene carbonate is an organic compound with formula C5H8O3, or (H5C2)(C2H3)(CO3). It is a double ester with the carbonate functional group bonded to both free ends of the 1,2-butylene group. It is also a heterocyclic compound with a five-membered ring, and can be seen as a derivative of dioxolane, specifically 4-ethyl-1,3-dioxolan-2-one.

1,2-Butylene carbonate is a polar aprotic solvent, which has been considered for electric battery applications (as a cheaper alternative to ionic liquids) and many other uses.

Allyl cyanide

Allyl cyanide is an organic compound with the formula CH2CHCH2CN. Like other small alkyl nitriles, allyl cyanide is colorless and soluble in organic solvents. Allyl cyanide occurs naturally as an antifeedant and is used as a cross-linking agent in some polymers.

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

C4H6O3

The molecular formula C4H6O3 may refer to:

Acetic anhydride

Acetoacetic acid

Dioxanones

p-Dioxanone

Trimethylene carbonate

trans-4-Hydroxycrotonic acid

α-Ketobutyric acid

2-Methyl-3-oxopropanoic acid

Methyl pyruvate

Propylene carbonate

Succinic semialdehyde

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.

Dimethoxyethane

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries. Dimethoxyethane is miscible with water.

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.

Lithium battery

Lithium batteries are primary 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 charge density (long life) and high cost per unit. Depending on the design and chemical compounds used, lithium cells can produce voltages from 1.5 V (comparable to a zinc–carbon or alkaline battery) to about 3.7 V.

Disposable primary lithium batteries must be distinguished from secondary lithium-ion or a lithium-polymer, which are rechargeable batteries. Lithium is especially useful, because its ions can be arranged to move between the anode and the cathode, using an intercalated lithium compound as the cathode material but without using lithium metal as the anode material. Pure lithium will instantly react with water, or even moisture in the air; the lithium in lithium ion batteries is in a less reactive compound.

Lithium batteries are widely used in portable consumer electronic devices, and in electric vehicles ranging from full sized vehicles to radio controlled toys. The term "lithium battery" refers to a family of different lithium-metal chemistries, comprising many types of cathodes and electrolytes but all with metallic lithium as the anode. The battery requires from 0.15 to 0.3 kg of lithium per kWh. As designed these primary systems use a charged cathode, that being an electro-active material with crystallographic vacancies that are filled gradually during discharge.

The most common type of lithium cell used in consumer applications uses metallic lithium as anode and manganese dioxide as cathode, with a salt of lithium dissolved in an organic solvent.

Oxamic acid

Oxamic acid is the organic compound with the formula H2NC(O)CO2H. It is a white, water-soluble solid. It is the monoamide of oxalic acid. Oxamic acid inhibits Lactate dehydrogenase A. The active site of lactate dehydrogenase (LDH) is closed off once oxamic acid attaches to the LDH-NADH complex, effectively inhibiting it.Oxamic acid also has applications in polymer chemistry. It increases the water solubility of certain polymers, including polyester, epoxide, and acrylic upon binding with them.

Polar solvent

In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen (as in a hydroxyl group), a nitrogen (as in an amine group) or a fluorine (as in hydrogen fluoride). In general terms, any solvent that contains a labile H+ is called a protic solvent. The molecules of such solvents readily donate protons (H+) to reagents. Conversely, aprotic solvents cannot donate hydrogen.

Polylactic acid

Polylactic acid or polylactide (PLA) is a thermoplastic aliphatic polyester derived from renewable resources. In 2010, PLA had the second highest consumption volume of any bioplastic of the world, although it is still not a commodity polymer. Its widespread application has been hindered by numerous physical and processing shortcomings.The name "polylactic acid" does not comply with IUPAC standard nomenclature, and is potentially ambiguous or confusing, because PLA is not a polyacid (polyelectrolyte), but rather a polyester.

Polypropylene carbonate

Polypropylene carbonate (PPC), a copolymer of carbon dioxide and propylene oxide, is a thermoplastic material. Catalysts like zinc glutarate are used in polymerization.

Sodium-ion battery

The sodium-ion battery (NIB) is a type of rechargeable battery analogous to the lithium-ion battery but using sodium ions (Na+) as the charge carriers. Its working principle and cell construction are identical with that of the commercially widespread lithium-ion battery with the only difference being that the lithium compounds are swapped with sodium compounds: in essence, it consists of a cathode based on a sodium containing material, an anode (not necessarily a sodium-based material) and a liquid electrolyte containing dissociated sodium salts in polar protic or aprotic solvents. During charging, Na+ are extracted from the cathode and inserted into the anode while the electrons travel through the external circuit; during discharging, the reverse process occurs where the Na+ are extracted from the anode and re-inserted in the cathode with the electrons travelling through the external circuit doing useful work. Ideally, the anode and cathode materials should be able to withstand repeated cycles of sodium storage without degradation.

Solvent

A solvent (from the Latin solvō, "loosen, untie, solve") is a substance that dissolves a solute (a chemically distinct liquid, solid or gas), resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. The quantity of solute that can dissolve in a specific volume of solvent varies with temperature. Common uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene), as paint thinners (e.g. toluene, turpentine), as nail polish removers and glue solvents (acetone, methyl acetate, ethyl acetate), in spot removers (e.g. hexane, petrol ether), in detergents (citrus terpenes) and in perfumes (ethanol). Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within a cell. Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical syntheses and purification processes.

Surface-tension values

This is a table of surface tension values for some interfaces at the indicated temperatures. Note that the SI units millinewtons per meter (mN·m−1) are equivalent to the cgs units dynes per centimetre (dyn·cm−1).

Trans-2,3-Butylene carbonate

trans-2,3-Butylene carbonate is an organic compound with formula C5H8O3, or (H3C)2(C2H2)(CO3). It is an ester with a carbonate functional group bonded to both free ends of the trans-2,3-butylene group. It is also a heterocyclic compound with a five-membered ring containing two oxygen atoms, and can be viewed as a derivative of dioxolane, namely trans-4,5-dimethyl-1,3-dioxolan-2-one.

The compound is an aprotic polar solvent and has been proposed as an ingredient of the electrolyte of lithium batteries.

Trimethylene carbonate

Trimethylene carbonate or 1,3-propylene carbonate is a 6-membered cyclic carbonate ester. It is a colourless solid that upon heating or catalytic ring-opening converts to the poly(trimethylene carbonate). Such polymers are called aliphatic polycarbonates are of interest for potential biomedical applications. An isomeric derivative is propylene carbonate, a colourless liquid that does not spontaneously polymerize.

VOC exempt solvent

VOC exempt solvents are organic compounds that are exempt from restrictions placed on most volatile organic compounds (VOCs) in the United States. This class currently includes acetone, dimethyl carbonate, methyl acetate, parachlorobenzotrifluoride (Oxsol 100), tert-butyl acetate, and propylene carbonate.

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