Diethyl phthalate

Structural formula
General
Surname	Diethyl phthalate
other names	Diethyl phthalate; Benzene-1,2-dicarboxylic acid diethyl ester; DEP;
Molecular formula	C 12 H 14 O 4
Brief description	colorless, almost odorless liquid
External identifiers / databases
EC number	201-550-6
ECHA InfoCard	100.001.409
PubChem	6781
Wikidata	Q419811
properties
Molar mass	222.24 g mol −1
Physical state	liquid
density	1.11 g cm −3
Melting point	−40.5 ° C , other source −3.2 ° C
boiling point	302 ° C
Vapor pressure	44 m Pa (20 ° C)
solubility	poor in water (1 g l −1 at 25 ° C); soluble in ethanol , acetone , diethyl ether , benzene , many aromatic and aliphatic solvents and vegetable oils;
Refractive index	1.5000 (21 ° C)
safety instructions
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	8600 mg kg −1 ( LD 50 , rat , oral )
	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

Diethyl phthalate is an organic compound from the group of phthalates , which is in the form of a colorless liquid.

Extraction and presentation

Diethyl phthalate can be prepared by reacting phthalic anhydride with ethanol in the presence of concentrated sulfuric acid as a catalyst.

properties

Diethyl phthalate is a colorless, almost odorless liquid. It has a viscosity of 12-14 mPa · s at 20 ° C. The vapors are eight times as heavy as air.

As a plasticizer, diethyl phthalate attacks some plastics.

use

Diethyl phthalate is used as formulation aids for pesticides and as a fixer for fragrances and the denaturing of ethanol (also in fragrances and cosmetics, which then as denat Alcohol. Declared) are used. It is also a very good gelling, lightfast plasticizer for cellulose esters . It is also used as a plasticizer for lacquer binders based on cellulose and in enteric coatings for pharmaceuticals. Furthermore, it is contained in cosmetic products due to its film-forming, softening and hair conditioning properties . In addition, diethyl phthalate is used for desensitization of explosives . Another possible use for DEP is its use as a carrier in the dyeing process of cellulose acetate or triacetate fibers .

Risk assessment

In 2012, diethyl phthalate was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Diethyl phthalate uptake was caused by concerns about its classification as a CMR substance, consumer use , high (aggregated) tonnage and widespread use, and as a potential endocrine disruptor . The reassessment took place from 2014 and was carried out by Germany . A final report was then published. Diethyl phthalate metabolites have already been detected in the urine of dolphins .

Web links

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diethyl phthalate in the GESTIS substance database of the IFA , accessed on June 27, 2019(JavaScript required) .
↑ Donald Mackay , Wan Ying Shiu, Kuo-Ching Ma: Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Oxygen, Nitrogen, and Sulfur-Containing Compounds . CRC Press, 1995, ISBN 978-1-56670-035-1 , pp. 648 ( limited preview in Google Book search).
↑ SS Chang, JA Horman, AB Bestul: Heat capacities and related thermal data for diethyl phthalate crystal, glass, and liquid to 360 K. In: Journal of Research of the National Bureau of Standards Section A: Physics and Chemistry. 71A, 1967, p. 293, doi : 10.6028 / jres.071A.036 .
↑ ^a ^b ^c Concise International Chemical Assessment Document (CICAD) for Diethyl phthalate , accessed on November 18, 2014.
↑ 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. 3-170.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 84-66-2 or diethyl phthalate ), accessed on November 2, 2015.
^ European Chemicals Agency (ECHA): Substance Evaluation Report and Conclusion Document .
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): diethyl phthalate , accessed on March 26, 2019.
↑ Leslie B. Hart, Barbara Beckingham, Randall S. Wells, Moriah Alten Flagg, Kerry Wischusen, Amanda Moors, John Kucklick, Emily Pisarski, E. d. Wirth: Urinary Phthalate Metabolites in Common Bottlenose Dolphins (Tursiops truncatus) From Sarasota Bay, FL, USA. In: GeoHealth. 2, 2018, p. 313, doi : 10.1029 / 2018GH000146 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diethyl phthalate in the GESTIS substance database of the IFA , accessed on June 27, 2019(JavaScript required) .

[Donald_Mackay,_Wan_Ying_Shiu,_Kuo-Ching_Ma-2] Donald Mackay , Wan Ying Shiu, Kuo-Ching Ma: Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals Oxygen, Nitrogen, and Sulfur-Containing Compounds . CRC Press, 1995, ISBN 978-1-56670-035-1 , pp. 648 ( limited preview in Google Book search).

[DOI10.6028/jres.071A.036-3] SS Chang, JA Horman, AB Bestul: Heat capacities and related thermal data for diethyl phthalate crystal, glass, and liquid to 360 K. In: Journal of Research of the National Bureau of Standards Section A: Physics and Chemistry. 71A, 1967, p. 293, doi : 10.6028 / jres.071A.036 .

[inchem-4] Concise International Chemical Assessment Document (CICAD) for Diethyl phthalate , accessed on November 18, 2014.

[CRC90_3_170-5] 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. 3-170.

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 84-66-2 or diethyl phthalate ), accessed on November 2, 2015.

[7] European Chemicals Agency (ECHA): Substance Evaluation Report and Conclusion Document .

[8] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): diethyl phthalate , accessed on March 26, 2019.

[DOI10.1029/2018GH000146-9] Leslie B. Hart, Barbara Beckingham, Randall S. Wells, Moriah Alten Flagg, Kerry Wischusen, Amanda Moors, John Kucklick, Emily Pisarski, E. d. Wirth: Urinary Phthalate Metabolites in Common Bottlenose Dolphins (Tursiops truncatus) From Sarasota Bay, FL, USA. In: GeoHealth. 2, 2018, p. 313, doi : 10.1029 / 2018GH000146 .