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| Names | |||
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| 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 | |||
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3D model (JSmol) | |||
| ChemSpider |
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| ECHA InfoCard | 100.003.248 | ||
| UNII | |||
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| 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) | |||
Refractive index (nD) | 1.4189 | ||
| Structure | |||
| 4.9D | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Irritant | ||
| GHS labelling:[3] | |||
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| Warning | |||
| H319 | |||
| P305+P351+P338 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 132 °C (270 °F; 405 K) | ||
| 455 °C (851 °F; 728 K) | |||
| Safety data sheet (SDS) | MSDS by SMC Global | ||
| Related compounds | |||
Related compounds | Ethylene carbonate Dimethyl carbonate | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Propylene carbonate (often abbreviatedPC) is anorganic compound with the formula C4H6O3. It is a cycliccarbonate ester derived frompropylene glycol.[4] This colorless and odorless liquid is useful as apolar,aprotic solvent.[5] Propylene carbonate ischiral, but is used as theracemic mixture in most contexts.
The namecarbonate indicates acarbonate ester, an organic compound containing thecarbonate groupO=C(−O−)2, not a salt ofcarbonic acid, (H2CO3),characterized by the presence of thecarbonate ion, apolyatomic ion with the formulaCO2−3.
Although many organic carbonates are produced usingphosgene, propylene and ethylene carbonates are exceptions. They are mainly prepared by thecarbonation of theepoxides[5] (epoxypropane, orpropylene oxide here):
The corresponding reaction of1,2-propanediol with phosgene is complex, yielding not only propylene carbonate but also oligomeric products.
Propylene carbonate can also be synthesized fromurea andpropylene glycol overzinc acetate.[6]
Propylene carbonate is used as a polar,aprotic solvent.[7] It has a highmolecular dipole moment (4.9D), considerably higher than those ofacetone (2.91D) andethyl acetate (1.78D).[1] It is possible, for example, to obtainpotassium,sodium, and otheralkali metals byelectrolysis of theirchlorides and other salts dissolved in propylene carbonate.[8]
Due to its highrelative permittivity (dielectric constant) of 64, it is frequently used as a high-permittivity component ofelectrolytes inlithium batteries, usually together with a low-viscosity solvent (e.g.dimethoxyethane). Its high polarity allows it to create an effectivesolvation shell around lithium ions, thereby creating a conductiveelectrolyte. However, it is not used inlithium-ion batteries due to its destructive effect ongraphite.[9]
Propylene carbonate can also be found in someadhesives,paint strippers, and incosmetics.[10] It is also used asplasticizer. 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 byEl Paso Natural Gas Company andFluor 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 bytransesterification as well (seeCarbonate ester#Carbonate transesterification).[5]
Inelectrospray ionization mass spectrometry, propylene carbonate is doped into low surface tension solutions to increase analyte charging.[12]
InGrignard reaction propylene carbonate (or most other carbonate esters) might be used to createtertiary alcohols.[13]
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 avolatile organic compound (VOC) because it does not contribute significantly to the formation ofsmog and because its vapor is not known or suspected to cause cancer or other toxic effects.[15]
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