Dimethyl phthalate

Structural formula
General
Surname	Dimethyl phthalate
other names	Dimethyl phthalate; Benzene-1,2-dicarboxylic acid dimethyl ester; DIMETHYL PHTHALATE ( INCI ) ;
Molecular formula	C 10 H 10 O 4
Brief description	light-sensitive, colorless, almost odorless liquid
External identifiers / databases
EC number	205-011-6
ECHA InfoCard	100.004.557
PubChem	8554
ChemSpider	13837329
Wikidata	Q423551
Drug information
ATC code	P03 BX02
properties
Molar mass	194.19 g mol −1
Physical state	liquid
density	1.19 g cm −3
Melting point	6 ° C
boiling point	282 ° C
Vapor pressure	0.008 hPa (20 ° C); 1.33 hPa (100 ° C);
solubility	slightly soluble in water (4.3 g l −1 )
Refractive index	1.5138 (20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
MAK	Switzerland: 5 mg m −3 (measured as inhalable dust )
Toxicological data	6800 mg kg −1 ( LD 50 , rat , oral ) ; > 23800 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

Dimethyl phthalate (DMP) is a phthalic acid ester made from methanol and phthalic acid and belongs to the group of phthalates in addition to diethylhexyl phthalate , di-isononyl phthalate , diethyl phthalate and dibutyl phthalate .

Presentation and extraction

The industrial production of dimethyl phthalate takes place in a two-stage synthesis from phthalic anhydride and methanol . The first step is rapid alcoholysis to form the phthalic acid half-ester. The second esterification step is slower as an equilibrium reaction and requires the use of acidic catalysts and, in order to complete the conversion, the distillative separation of the water formed.

properties

Dimethyl phthalate is a light-sensitive, colorless, less volatile, highly viscous (dynamic viscosity of 1.7 mPa · s at 20 ° C.) And almost odorless liquid that is sparingly soluble in water. It decomposes in the heat, producing carbon monoxide and carbon dioxide as well as irritating vapors and gases.

Dimethyl phthalate is considered a difficultly flammable liquid. Flammable vapor-air mixtures can form above the flash point . The compound has a flash point of 146 ° C. The explosion range begins at 0.9 vol.% As the lower explosion limit (LEL). The lower explosion point is 134 ° C. The ignition temperature is 555 ° C. The substance therefore falls into temperature class T1.

use

DMP is used as a plasticizer , as a repellent against insects, where it is particularly effective against Anopheles , and as a solvent in glow sticks ("glow stick").

Individual evidence

↑ Entry on DIMETHYL PHTHALATE in the CosIng database of the EU Commission, accessed on February 11, 2020.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry for CAS no. 131-11-3 in the GESTIS substance database of the IFA , accessed on June 28, 2018(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. 3-208.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 131-11-3 or dimethyl phthalate ), accessed on November 2, 2015.
↑ ^a ^b P.M. Lorz, FK Towae, W. Enke, R. Jäckh, N. Bhargava, W. Hillesheim: Phthalic Acid and Derivatives in Ullmann's Encyclopedia of Industrial Chemistry, 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007 .a20_181.pub2 .
↑ ^a ^b E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.
↑ Wolfgang Legrum: Fragrances, between stink and fragrance , Vieweg + Teubner Verlag (2011) p. 75, ISBN 978-3-8348-1245-2 .
↑ Military Preventive Medicine: Mobilization and Deployment, Vol 1.Chapter 22: Personal Protection Measures Against Arthropods, p. 508.

[CosIng-1] Entry on DIMETHYL PHTHALATE in the CosIng database of the EU Commission, accessed on February 11, 2020.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry for CAS no. 131-11-3 in the GESTIS substance database of the IFA , accessed on June 28, 2018(JavaScript required) .

[CRC90_3_208-3] 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. 3-208.

[4] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 131-11-3 or dimethyl phthalate ), accessed on November 2, 2015.

[Ullmann-5] P.M. Lorz, FK Towae, W. Enke, R. Jäckh, N. Bhargava, W. Hillesheim: Phthalic Acid and Derivatives in Ullmann's Encyclopedia of Industrial Chemistry, 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi : 10.1002 / 14356007 .a20_181.pub2 .

[Brandes-6] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[Legrum-7] Wolfgang Legrum: Fragrances, between stink and fragrance , Vieweg + Teubner Verlag (2011) p. 75, ISBN 978-3-8348-1245-2 .

[8] Military Preventive Medicine: Mobilization and Deployment, Vol 1.Chapter 22: Personal Protection Measures Against Arthropods, p. 508.