Diallyl phthalate

Structural formula
General
Surname	Diallyl phthalate
other names	Diallyl phthalate Benzene-1,2-dicarboxylic acid diprop-2-enyl ester DAP 1,2-Benzene dicarboxylic acid di-2-propenyl ester
Molecular formula	C 14 H 14 O 4
Brief description	colorless to yellowish liquid with a pleasant odor
External identifiers / databases
CAS number 131-17-9 EC number 205-016-3 ECHA InfoCard 100,004,562 PubChem 8560 Wikidata Q2161731
properties
Molar mass	246.26 g mol −1
Physical state	liquid
density	1.12 g cm −3
Melting point	−70 ° C
boiling point	290 ° C
Vapor pressure	0.002 hPa (20 ° C)
solubility	very sparingly soluble in water (0.18 g l −1 at 20 ° C)
Refractive index	1.519 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 302-410 P: 273-501
Toxicological data	3300 mg kg −1 ( LD 50 ,  rabbit ,  transdermal ) 656 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

Diallyl phthalate is a chemical compound from the group of phthalic acid esters .

Extraction and presentation

Diallyl phthalate is conventionally made by esterifying phthalic anhydride with allyl alcohol or allyl chloride .

properties

Diallyl phthalate is a flammable, hardly inflammable, oily, colorless to yellowish liquid with a pleasant odor, which is very sparingly soluble in water. It contains two unsaturated groups in the molecule and can therefore polymerize directly to form crosslinked products.

use

Diallyl phthalate can be used for the production ( polymerisation ) of allyl resins by means of peroxidic catalysts . In many cases, polyester molding compounds are also added instead of styrene . For the actual diallyl phthalate molding compositions, however, the monomeric diallyl phthalate is prepolymerized on one of the two double bonds by a special process. Like other resins, this prepolymer is used to prepare curable molding compounds either in the melt flow or liquid resin process (resin solution). The prepolymerized product can then be polymerized further at the second double bond. Diallyl phthalate polymers are used for a variety of purposes because of their excellent properties ( radar hoods , components for nuclear and rocket technology, ...).

Risk assessment

Compared to phthalic acid esters with saturated alcohols , diallyl phthalate is relatively toxic. In the case of single and repeated oral administration, liver cell necrosis and fibrotic lesions in the periportal region are the most common. Diallyl phthalate is moderately irritating to the skin and mucous membranes.

Diallyl phthalate was not found to be mutagenic in bacteria. A clastogenic potential was observed in mammalian cells at doses, some of which were cytotoxic . In a carcinogenicity study, diallyl phthalate was not found to be carcinogenic in male rats and female mice. The results in female rats and male mice were assessed as questionably positive.

In 2012, diallyl 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. Diallyl phthalate uptake was caused by concerns about its classification as a CMR substance, consumer use and widespread use. The re-evaluation took place from 2013 and was carried out by Spain . A final report was then published.

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on diallyl phthalate in the GESTIS substance database of the IFA , accessed on January 14, 2017(JavaScript required) .
2. ↑ Data sheet Diallyl phthalate, 97% from Sigma-Aldrich , accessed on January 14, 2017 ( PDF ).
3. ↑ Entry on diallyl phthalate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 14, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Hans-Georg Elias: Macromolecules Volume 3: Industrial Polymers and Syntheses . John Wiley & Sons, 2009, ISBN 3-527-62652-2 , pp. 230 ( limited preview in Google Book search).
5. ↑ Entry on Diallyl phthalate in the Hazardous Substances Data Bank , accessed January 14, 2017.
6. ↑ ^{a b} AVK - Industrial Association for Reinforced Plastics: Handbook fiber composite plastics / composites basics, processing, applications . Springer-Verlag, 2014, ISBN 978-3-658-02755-1 , pp. 59 ( limited preview in Google Book search).
7. ^ Fritz Weigel: Chemistry for mechanical engineers and electrical engineers Textbook for students of mechanical engineering and electrical engineering from the 1st semester . Springer-Verlag, 2013, ISBN 978-3-322-85458-2 , p. 124 ( limited preview in Google Book search).
8. ↑ ^{a b} The MAK Collection for Occupational Health and Safety . Wiley-VCH Verlag & Co. KGaA, 2002, ISBN 978-3-527-60041-0 , diallyl phthalate [MAK Value Documentation in German language, 1994].
9. ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
10. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Diallyl phthalate , accessed on March 26, 2019.