Propylene carbonate

Structural formula
	Structural formula without stereochemistry
General
Surname	Propylene carbonate
other names	4-methyl-1,3-dioxolan-2-one; Propylene glycol carbonate; Carbonic acid propylene glycol ester;
Molecular formula	C 4 H 6 O 3
Brief description	colorless to yellowish liquid with a fruity odor
External identifiers / databases
EC number	203-572-1
ECHA InfoCard	100.003.248
PubChem	7924
ChemSpider	7636
Wikidata	Q415979
properties
Molar mass	102.09 g mol −1
Physical state	liquid
density	1.21 g ml −1
Melting point	−49 ° C
boiling point	242 ° C
Vapor pressure	4 Pa (20 ° C); 1.3 hPa (50 ° C);
solubility	good in water (240 g l −1 at 20 ° C)
Refractive index	1.4189 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 319
	P: 305 + 351 + 338
Toxicological data	29 g kg −1 ( LD 50 , rat , oral )
Thermodynamic properties
ΔH f 0	−613.2 kJ / mol (l) ; −563.7 kJ / mol (g)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Propylene carbonate (4-methyl-1,3-dioxolan-2-one) is a clear, colorless, easily mobile, almost odorless liquid. As a carbonate , it is an ester of bivalent carbonic acid , here with the dihydric alcohol 1,2-propanediol . It is used as a polar solvent, among other things, but has many more uses.

It is increasingly replacing cresols, which are more questionable in terms of ecology and occupational safety .

Manufacturing

Propylene carbonate is a by-product of the synthesis of polypropylene carbonate from propylene oxide and carbon dioxide . It can also be made from propylene glycol and urea with zinc iron mixed oxide catalyst.

properties

Propylene carbonate has a very high dipole moment, which makes it suitable as a solvent.

( R ) -propylene carbonate (left) and ( S ) -propylene carbonate (right). As a rule, these compounds are used as a 1: 1 mixture.

Stereoisomerism

Propylene carbonate has a stereogenic center. Hence there are two stereoisomers, ( R ) - and ( S ) -4-methyl-1,3-dioxolan-2-one. Propylene carbonate is usually used in industry as a 1: 1 mixture ( racemate ) of ( R ) - and ( S ) -4-methyl-1,3-dioxolan-2-one. In enantioselective synthesis, however, the pure enantiomers ( R ) - or ( S ) -4-methyl-1,3-dioxolan-2-one are sometimes used.

Safety-related parameters

Propylene carbonate forms flammable vapor-air mixtures at higher temperatures. The compound has a flash point of 135 ° C. The lower explosion limit is 2.3 vol.% (98 g / m ³ ). The ignition temperature is 430 ° C. The substance therefore falls into temperature class T2.

use

Solvents, for example in inks , paints, universal cleaners , tar removers , nail polish removers

Degreasing of metals

Extractant for aromatic hydrocarbons

Electrolyte in batteries with high energy density

Electrolyte systems for electrochemical investigations and galvanic deposition of strongly electropositive metals (e.g. alkali metals , lanthanoids ) and conductive plastics such as polymethylthiophene ( electropolymerization )

Core sand binders in the foundry industry and as a swelling agent for special clay minerals e.g. B. in paints, cosmetics or lubricants

Intermediate product in chemical-organic synthesis / reactant

Plasticizers for plastics

Liquid in liquid thermometers

literature

N. Holstein, Electrochemical deposition of Sm-Co alloys from aprotic electrolytes, Shaker Verlag , 2000, ISBN 3-8265-7748-5 .
R. Schmitz, Electronic and ionic conductivity of poly (3-methylthophene) films, Shaker Verlag, 1999, ISBN 90-423-0085-X .
B. Schäffner, SP Verevkin, A. Börner: Organic carbonates. Green solvents for synthesis and catalysis , Chemie in Unserer Zeit , 2009 , 43 , pp. 12–21; doi: 10.1002 / ciuz.200900468 .
B. Schäffner, F. Schäffner, SP Verevkin, A. Börner: Organic Carbonates as Solvents in Synthesis and Catalysis , Chemical Reviews , 2010 , 110 , pp. 4554-4581; doi: 10.1021 / cr900393d .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on propylene carbonate in the GESTIS substance database of the IFA , accessed on March 24, 2019(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-444.
↑ Entry on Propylene carbonate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Buysch, H.-J .: Carbonic Esters in Ullmann's Encyclopedia of Industrial Chemistry, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.a05_197 .
↑ CRC-Handbook "Standard Thermodynamic Properties of Chemical Substances" 90th edition (2009-2010), pp. 5-26 ( Memento of April 26, 2015 in the Internet Archive ).
↑ Entry on propylene carbonate . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed March 22, 2010.
↑ Amarell precision thermometers and hydrometers accessed on August 21, 2020.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on propylene carbonate in the GESTIS substance database of the IFA , accessed on March 24, 2019(JavaScript required) .

[CRC90_3_444-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-444.

[CLP_100.003.248-3] Entry on Propylene carbonate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Ullmann-4] Buysch, H.-J .: Carbonic Esters in Ullmann's Encyclopedia of Industrial Chemistry, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007.a05_197 .

[5] CRC-Handbook "Standard Thermodynamic Properties of Chemical Substances" 90th edition (2009-2010), pp. 5-26 ( Memento of April 26, 2015 in the Internet Archive ).

[6] Entry on propylene carbonate . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD, accessed March 22, 2010.

[7] Amarell precision thermometers and hydrometers accessed on August 21, 2020.