Bis (2-ethylhexyl) phthalate

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Structural formula
Structural formula of diethylhexyl phthalate

Mixture of stereoisomers (mixture of three isomers)
Structural formula without indication of stereochemistry
General
Surname Bis (2-ethylhexyl) phthalate
other names
  • DEHP
  • Diethylhexyl phthalate
  • Di (2-ethylhexyl) phthalate
  • Di- sec -octyl phthalate
  • Bis-2-ethylhexyl phthalate
Molecular formula C 24 H 38 O 4
Brief description

colorless, neutral, oily and odorless liquid

External identifiers / databases
CAS number 117-81-7
EC number 204-211-0
ECHA InfoCard 100,003,829
PubChem 8343
Wikidata Q418492
properties
Molar mass 390.56 g mol −1
Physical state

liquid

density

0.99 g cm −3

Melting point

approx. −50 ° C

boiling point

385 ° C

solubility

almost insoluble in water (<0.1 g · l −1 ),
soluble in oils and in many organic solvents

Refractive index

1.4853 (20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
08 - Dangerous to health

danger

H and P phrases H: 360FD
P: 201-280-308 + 313
Authorization procedure under REACH

of particular concern : toxic for reproduction ( CMR ), serious effects on human health and the environment are considered probable; subject to approval

MAK
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

Bis (2-ethylhexyl) phthalate (also diethylhexyl phthalate , DEHP ) is one of the most important phthalate- based plasticizers , more precisely the diester of phthalic acid and racemic 2-ethylhexanol . In 2010, the market share of global plasticizer consumption was just under 54%.

Isomerism

The three stereoisomers of DEHP

A structural isomer of DEHP is di- n -octyl phthalate (DOP). DEHP has a stereocenter at each branch point of the two 2-ethylhexyl residues, so there are three DEHP stereoisomers :

  • ( R , R ) -DEHP,
  • ( S , S ) -DEHP and
  • meso -DEHP.

In technology, DEHP is used almost exclusively as a mixture of these three stereoisomers. As a rule, such stereoisomers have different physiological and thus also toxicological properties.

use

DEHP is widely used as a plasticizer for PVC plastics and as an additive in paints, cosmetic products and pesticides .

Analytics

For a reliable qualitative and quantitative determination of DEHP, the coupling of gas chromatography with mass spectrometry can be used after appropriate sample preparation . DEHP can also be detected in paper cups . The method is also suitable for the determination of DEHP in hair samples .

Problem

When this fabric is incorporated into polymer fabrics, they become more elastic and pliable. DEHP does not form a chemical compound and can therefore escape from plastics over time and z. B. migrate from food packaging into the food . In order to prove the effectiveness of the plasticizers, researchers at the University of Leipzig supplied mice with drinking water that contained DEHP. They found that the mice gained significantly in weight, especially the females.

Diisononyl phthalate is used as a substitute for the manufacture of PVC products . According to studies by the University of Erlangen, the average intake of DEHP is significantly higher than the limit set by the European Commission . This can have negative health consequences for the testes, kidneys and liver. The IARC classified DEHP as possibly carcinogenic in 2013.

Since October 28, 2008 DEHP has been on the so-called "candidate list" of the ECHA . If DEHP is contained in an article, there is an obligation to inform the customer. It is already forbidden to use DEHP in toys and baby items, as the substance is listed in Appendix 1 of the Consumer Goods Ordinance .

In EU Regulation No. 143/2011 of February 17, 2011, bis (2-ethylhexyl) phthalate (DEHP) is classified as toxic to reproduction and January 21, 2015 is defined as the date from which the substance is placed on the market and used within is banned in the EU without authorization.

On March 31, 2015, DEHP were added to the RoHS substance list with Directive (EU) 2015/863 . Since July 22, 2019, electrical and electronic equipment containing parts with more than 0.1% by weight DEHP in the homogeneous material may no longer be sold in the EU.

DEHP metabolites have already been detected in the urine of dolphins .

Individual evidence

  1. a b c d e f g h i Entry on bis (2-ethylhexyl) phthalate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  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. 3-52.
  3. Entry on bis (2-ethylhexyl) phthalate 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 .
  4. Entry in the SVHC list of the European Chemicals Agency , accessed on July 7, 2017.
  5. Entry in the register of substances subject to authorization of the European Chemicals Agency , accessed on July 7, 2017.
  6. Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 117-81-7 or bis (2-ethylhexyl) phthalate ), accessed on November 2, 2015.
  7. Market study plasticizers , Ceresana, May 2011.
  8. ^ EJ Ariëns: Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. In: European Journal of Clinical Pharmacology . 26, 1984, pp. 663-668, doi: 10.1007 / BF00541922 .
  9. Z. Haned, p Moulay, S. Lacorte: Migration of Plasticizers from poly (vinyl chloride) and multilayer infusion bags using selective extraction and GC-MS. In: J Pharm Biomed Anal. 156, Jul 15, 2018, pp. 80–87. PMID 29694937
  10. MV Russo, P. Avino, I. Notardonato: Fast analysis of phthalates in freeze-dried baby foods by ultrasound-vortex-assisted liquid-liquid microextraction coupled with gas chromatography-ion trap / mass spectrometry. In: J Chromatogr A. 1474, Nov 25, 2016, pp. 1-7. PMID 28314431
  11. YN Park, MS Choi, SU Rehman, MC Gye, HH Yoo: Simultaneous GC-MS determination of seven phthalates in total and migrated portions of paper cups. In: Environ Sci Pollut Res Int. 23 (10), May 2016, pp. 10270-10275. PMID 27053047
  12. J. Martín, M. Möder, A. Gaudl, E. Alonso, T. Reemtsma: Multi-class method for biomonitoring of hair samples using gas chromatography-mass spectrometry. In: Anal Bioanal Chem. 407 (29), Nov 2015, pp. 8725-8734. PMID 26427497
  13. Nora Klöting, Nico Hesselbarth a. a .: Di- (2-Ethylhexyl) -Phthalate (DEHP) Causes Impaired Adipocyte Function and Age Serum Metabolites. In: PLOS ONE. 10, 2015, p. E0143190, doi: 10.1371 / journal.pone.0143190 .
  14. IARC Monograph 101 - DEHP, 2013
  15. ECHA: List of candidates for inclusion in the list of substances subject to authorization.
  16. Regulation (EU) No. 143/2011 of the Commission of February 17, 2011 amending Annex XIV of Regulation (EC) No. 1907/2006 of the European Parliament and of the Council on the Registration, Evaluation, Authorization and Restriction of Chemicals (REACH )
  17. ↑ Commission Delegated Directive (EU) 2015/863 of March 31, 2015 amending Annex II of Directive 2011/65 / EU of the European Parliament and of the Council with regard to the list of restricted substances , accessed on July 2, 2019
  18. 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 .

literature

  • Armin Gärtner: Plasticizers (DEHP) in medical products. In: mt medical technology. 3/2007, TUEV Media Verlag Cologne, pp. 92-103.
  • Hermann Fromme, Wolfgang Körner, Ludwig Gruber, Dieter Heitmann, Martin Schlummer, Wolfgang Völkel, Gabriele Bolte: Exposure of the population to phthalates. In: Hazardous substances, keeping air clean. Volume 70, No. 3, 2010, pp. 77-81, ISSN  0949-8036 .
  • Gerhard Volland, Thomas Gabrio, Roman Wodarz, Dagmar Hansen, Volker Mann, Sibylle Hildenbrand: Influence of di (2-ethylhexyl) phthalate (DEHP) in house dust and indoor air on daily DEHP intake. In: Hazardous substances, keeping air clean. Volume 70, No. 3, 2010, pp. 83-88, ISSN  0949-8036 .

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