Propylene carbonate

Last updated
Propylene carbonate [1] [2]
Propylene Carbonate V.1.svg
Propylene-carbonate-3D-vdW.png
Sample of propylene carbonate.jpg
Names
Preferred IUPAC name
4-Methyl-1,3-dioxolan-2-one
Other names
(RS)-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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H8O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/p-1 Yes check.svgY
    Key: ZEBXBLIKXVICMJ-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/C5H8O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/p-1
    Key: ZEBXBLIKXVICMJ-REWHXWOFAP
  • CC1COC(=O)O1
Properties
C4H6O3
Molar mass 102.089 g·mol−1
AppearanceColorless 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
Structure
4.9 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling: [3]
GHS-pictogram-exclam.svg
Warning
H319
P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
1
1
Flash point 132 °C (270 °F; 405 K)
455 °C (851 °F; 728 K)
Safety data sheet (SDS) MSDS by Mallinckrodt Baker
Related compounds
Related compounds
 Ethylene carbonate
Dimethyl carbonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol. [4] This colorless and odorless liquid is useful as a polar, aprotic solvent. [5] Propylene carbonate is chiral, but is used as the racemic mixture in most contexts.

Contents

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 [5] (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. [6]

Applications

As a solvent

Propylene carbonate is used as a polar, aprotic solvent. [7] 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. [8]

Electrolyte

Due to its high relative permittivity (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. [9]

Other

Propylene carbonate can also be found in some adhesives, paint strippers, and in cosmetics. [10] 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. [11]

Propylene carbonate product may be converted to other carbonate esters by transesterification as well (see Carbonate ester#Carbonate transesterification). [5]

In electrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging. [12]

In Grignard reaction propylene carbonate (or most other carbonate esters) might be used to create tertiary alcohols. [13]

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. [14] 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. [15]

See also

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. 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 the cell.

<span class="mw-page-title-main">Ethylene glycol</span> Organic compound ethane-1,2-diol

Ethylene glycol is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is toxic in high concentrations. This molecule has been observed in outer space.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.

<span class="mw-page-title-main">Propylene oxide</span> Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula C3H6O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

<span class="mw-page-title-main">Dimethoxyethane</span> Chemical compound

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.

In organic chemistry a halohydrin is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups. The term only applies to saturated motifs, as such compounds like 2-chlorophenol would not normally be considered halohydrins. Megatons of some chlorohydrins, e.g. propylene chlorohydrin, are produced annually as precursors to polymers.

<span class="mw-page-title-main">Lithium fluoride</span> Chemical compound

Lithium fluoride is an inorganic compound with the chemical formula LiF. It is a colorless solid that transitions to white with decreasing crystal size. Its structure is analogous to that of sodium chloride, but it is much less soluble in water. It is mainly used as a component of molten salts. Partly because Li and F are both light elements, and partly because F2 is highly reactive, formation of LiF from the elements releases one of the highest energies per mass of reactants, second only to that of BeO.

<span class="mw-page-title-main">Diethylenetriamine</span> Chemical compound

Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.

Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. It is related to tetrahydrofuran (THF) by replacement of the methylene group (CH2) at the 2-position with an oxygen atom. The corresponding saturated 6-membered C4O2 rings are called dioxanes. The isomeric 1,2-dioxolane (wherein the two oxygen centers are adjacent) is a peroxide. 1,3-dioxolane is used as a solvent and as a comonomer in polyacetals.

<span class="mw-page-title-main">Carbonate ester</span> Chemical group (R–O–C(=O)–O–R)

In organic chemistry, a carbonate ester 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 R−O−C(=O)−O−R' and they are related to esters, ethers and also to the inorganic carbonates.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.

<span class="mw-page-title-main">Ethylene carbonate</span> Chemical compound

Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the cyclic 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.

<span class="mw-page-title-main">Diethyl carbonate</span> Chemical compound

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

<span class="mw-page-title-main">Propylene glycol methyl ether</span> Chemical compound

Propylene glycol methyl ether is an organic solvent with a wide variety of industrial and commercial uses. Similar to other glycol ethers, it is used as a carrier/solvent in printing/writing inks and paints/coatings. It also finds use as an industrial and commercial paint stripper. It is used as an antifreeze in diesel engines.

<span class="mw-page-title-main">Tetramethylurea</span> Chemical compound

Tetramethylurea is the organic compound with the formula (Me2N)2CO. It is a substituted urea. This colorless liquid is used as an aprotic-polar solvent, especially for aromatic compounds and is used e. g. for Grignard reagents.

<span class="mw-page-title-main">Glycerol-1,2-carbonate</span> Organic chemical compound

Glycerol-1,2-carbonate is formally the cyclic ester of carbonic acid with glycerol and has aroused great interest as a possible product from the "waste materials" carbon dioxide CO2 and glycerol (especially from biodiesel production) with a wide range of applications.

References

  1. 1 2 Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. ISBN   1-4398-5511-0.
  2. ↑ Propylene carbonate at Sigma-Aldrich.
  3. ↑ GHS: GESTIS 070730
  4. ↑ WebBook page for propylene carbonate.
  5. 1 2 3 Hans-Josef Buysch. "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197. ISBN   978-3527306732..
  6. ↑ Synthesis of propylene carbonate from urea http://pubs.acs.org/doi/abs/10.1021/ie049948i
  7. ↑ Dieter Stoye. "Solvents". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437. ISBN   978-3527306732..
  8. ↑ 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. S2CID   93629501.
  9. ↑ Doron Aurbach (1999). Nonaqueous Electrochemistry. CRC Press. ISBN   978-0824773342.
  10. ↑ Propylene carbonate in the Consumer Product Information Database.
  11. ↑ Schendel, R. "Comparison of Fluor Solvent and Selexol Processes" (PDF). Retrieved 4 April 2016.
  12. ↑ 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.
  13. ↑ Payne, Richard; Theodorou, Ignatius E. (September 1972). "Dielectric properties and relaxation in ethylene carbonate and propylene carbonate". The Journal of Physical Chemistry. 76 (20): 2892–2900. doi:10.1021/j100664a019. ISSN   0022-3654.
  14. ↑ "Environmental Profile for Propylene Carbonate". U.S. Environmental Protection Agency. 1998.
  15. ↑ 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.
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