Diethyl phthalate

Last updated
Diethyl phthalate [1]
Diethyl phthalate 200.svg
Diethyl phthalate 3D ball.png
Names
Preferred IUPAC name
Diethyl benzene-1,2-dicarboxylate
Other names
Diethyl phthalate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.409 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3 Yes check.svgY
    Key: FLKPEMZONWLCSK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3
    Key: FLKPEMZONWLCSK-UHFFFAOYAV
  • CCOC(=O)c1ccccc1C(=O)OCC
Properties
C6H4(COOC2H5)2
Molar mass 222.240 g·mol−1
AppearanceColourless, oily liquid
Density 1.12 g/cm3 (20 °C (68 °F; 293 K)) [2]
Melting point −3 °C (27 °F; 270 K) [2]
Boiling point 298–299 °C (568–570 °F; 571–572 K) [2]
1.080 g/L
log P 2.42
Vapor pressure
  • 0.27 pascals (0.002 mmHg) (25 °C (77 °F; 298 K) [3]
  • 190 pascals (1.4 mmHg) (163 °C (325 °F; 436 K)) [2]
−127.5×10−6 cm3/mol
Viscosity 9.500 Pa·s [2]
Hazards
GHS labelling: [2]
H402
P273, P501
NFPA 704 (fire diamond)
[4]
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point 170 °C (338 °F; 443 K) [2] 101.3 kPa
457 °C (855 °F; 730 K) [2]
Explosive limits 0.7%, lower (187 °C (369 °F; 460 K) [2]
Lethal dose or concentration (LD, LC):
  • 5591 mg/kg (rat, oral)
  • >11181 mg/kg (rat, dermal)
≥4.64 mg/L (rat, vapor, 6h)
NIOSH (US health exposure limits): [5]
PEL (Permissible)
None
REL (Recommended)
5 mg/m3 (TWA)
IDLH (Immediate danger)
N.D.
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diethyl phthalate (DEP) is a phthalate ester with the formula C6H4(COOC2H5)2 (or C12H14O4). It is a colourless liquid without significant odour but with a bitter disagreeable taste.

Contents

Synthesis

Diethyl phthalate is produced by the reaction of ethanol with phthalic anhydride, in the presence of a strong acid catalyst:

Synthesis-DEP.png

Applications

It has been used as a plasticizer for cellulose acetate in many applications, the most common being scotch tape, film, eyewear frames, and biodegradable plastics; concentrations vary from 10% to 25% by weight. [6] It is compatible as a plasticizer with most cellulose derivatives including nitrocellulose, as well as polystyrene (styrofoam), polymethyl methacrylate (Plexiglass), polyvinyl acetate (white glue), polyvinyl butyral, and polyvinyl chloride (PVC), though the less volatile and less migration-prone dibutyl phthalate or a heavier phthalate was often preferred for long-chain or higher molecular weight polymers. [7] [6]

It has been used in double-base propellants with high percentages of nitroglycerin. In these compositions, nitroglycerin acts as the plasticizer. The specific function of diethyl phthalate is not given. [8] In ammonium perchlorate composite propellant, it has effects on viscosity similar to dibutyl phthalate and dioctyl adipate, but a higher density and lower fuel value than either. [9]

It has also been used as a blender and fixative in perfume. [10]

Biodegradation

Biodegradation by microorganisms

Biodegradation of DEP in soil occurs by sequential hydrolysis of the two diethyl chains of the phthalate to produce monoethyl phthalate, followed by phthalic acid. This reaction occurs very slowly in an abiotic environment. Another pathway exists when methanol is also present. This biodegradation has been observed in several soil bacteria. [11]

Biodegradation by mammals

Recent studies show that DEP, a phthalic acid ester (PAE), is enzymatically hydrolyzed to its monoesters by pancreatic cholesterol esterase (CEase) in pigs and cows. These mammalian pancreatic CEases have been found to be nonspecific for degradation in relation to the diversity of the alkyl side chains of PAEs. [12]

Toxicity

Little is known about the chronic toxicity of diethyl phthalate, but existing information suggests only a low toxic potential. [13] Studies suggest that some phthalates affect male reproductive development via inhibition of androgen biosynthesis. In rats, for instance, repeated administration of DEP results in loss of germ cell populations in the testis. However, diethyl phthalate does not alter sexual differentiation in male rats. [14] [15] [16] [17]

Cumulative

Some data suggest that exposure to multiple phthalates at low doses significantly increases the risk in a dose additive manner. [18] [19] [20] Therefore, the risk from a mixture of phthalates or phthalates and other anti-androgens may not be accurately assessed studying one chemical at a time. The same may be said about risks from several exposure routes together. Humans are exposed to phthalates by multiple exposure routes (predominantly dermal), while toxicological testing is done via oral exposure. [21]

References

  1. ↑ "Chemical Information Profile for Diethyl Phthalate" (PDF). Integrated Laboratory Systems, Inc. Archived (PDF) from the original on 1 February 2009. Retrieved 3 March 2009.
  2. 1 2 3 4 5 6 7 8 9 Sigma-Aldrich Co., Diethyl phthalate.
  3. ↑ NIOSH Pocket Guide to Chemical Hazards. "#0213". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ "SDS - Diethyl phthalate". fisherschi.com. Thermo-Fisher Scientific. 24 December 2021. Retrieved 11 November 2025.
  5. ↑ "NIOSH Pocket Guide to Chemical Hazards".
  6. 1 2 Wypych, George (2012). Handbook of plasticizers (2nd ed.). Toronto: ChemTec Pub. p. 278. ISBN   978-1-895198-50-8 . Retrieved 11 November 2025.
  7. ↑ {{cite report |title=Plasticizers |last1=Godwin |first1=A.D |page=159 |publisher=Exxon Chemical Company, Basic Chemicals and Intermediates Technology |location=Baytown, TX |url=http://kinampark.com/PL/files/Godwin%2C%20Plasticizer.pdf
  8. ↑ Kaye, Seymour M. (1 January 1978). "P - Propellants, Solid". Encyclopedia of Explosives and Related Items. Volume 8 (PDF). Dover, NJ: Army Armament Research And Development Center - Large Caliber Weapon Systems Lab. p. P-407. ADA057762, PATR 2700.
  9. ↑ Muthiah, Rm.; Somasundaran, U. I.; Verghese, T. L.; Thornas, V. A. (1 April 1989). "Energetics and Compatibility of Plasticizers in Composite Solid Propellants". Defence Science Journal. 39 (2): 147–155. doi: 10.14429/DSJ.39.4759 . S2CID   95997828.
  10. ↑ Api, A.M. (February 2001). "Toxicological profile of diethyl phthalate: a vehicle for fragrance and cosmetic ingredients". Food and Chemical Toxicology. 39 (2): 97–108. doi:10.1016/s0278-6915(00)00124-1. PMID   11267702.
  11. ↑ Cartwright, C.D. (March 2000). "Biodegradation of diethyl phthalate in soil by a novel pathway". FEMS Microbiology Letters. 186 (1): 27–34. doi: 10.1016/S0378-1097(00)00111-7 . PMID   10779708.
  12. ↑ Saito, T.; Peng, H.; Tanabe, R.; Nagai, K.; Kato, K. (December 2010). "Enzymatic hydrolysis of structurally diverse phthalic acid esters by porcine and bovine pancreatic cholesterol esterases". Chemosphere. 81 (1): 1544–1548. Bibcode:2010Chmsp..81.1544S. doi:10.1016/j.chemosphere.2010.08.020. PMID   20822795. S2CID   6958344.
  13. ↑ J. Autian (1973). "Toxicity and health threats of phthalate esters: review of the literature". Environmental Health Perspectives. 4: 3–25. doi:10.2307/3428178. JSTOR   3428178. PMC   1474854 . PMID   4578674.
  14. ↑ Antonia M. Calafat; Richard H. McKee (2006). "Integrating Biomonitoring Exposure Data into the Risk Assessment Process: Phthalates [Diethyl Phthalate and Di(2-ethylhexyl) Phthalate] as a Case Study". Environmental Health Perspectives. 114 (11): 1783–1789. doi:10.1289/ehp.9059. PMC   1665433 . PMID   17107868.
  15. ↑ Paul M. D. Foster; et al. (1980). "Study of the testicular effects and changes in zinc excretion produced by some n-alkyl phthalates in the rat". Toxicology and Applied Pharmacology . 54 (3): 392–398. doi:10.1016/0041-008X(80)90165-9. PMID   7394794.
  16. ↑ P. M. D. Foster; et al. (1981). "Studies on the testicular effects and zinc excretion produced by various isomers of monobutyl-o-phthalate in the rat". Chemico-Biological Interactions. 34 (2): 233–238. doi:10.1016/0009-2797(81)90134-4. PMID   7460085.
  17. ↑ L. Earl Gray Jr; et al. (2000). "Perinatal Exposure to the Phthalates DEHP, BBP, and DINP, but Not DEP, DMP, or DOTP, Alters Sexual Differentiation of the Male Rat". Toxicological Sciences . 58 (2): 350–365. doi:10.1093/toxsci/58.2.350. PMID   11099647.
  18. ↑ L. Earl Gray Jr; et al. (2006). "Adverse effects of environmental antiandrogens and androgens on reproductive development in mammals". International Journal of Andrology. 29 (1): 96–104. doi:10.1111/j.1365-2605.2005.00636.x. PMID   16466529.
  19. ↑ Kembra L. Howdeshell; et al. (2008). "A Mixture of Five Phthalate Esters Inhibits Fetal Testicular Testosterone Production in the Sprague-Dawley Rat in a Cumulative, Dose-Additive Manner". Toxicological Sciences. 105 (1): 153–165. doi: 10.1093/toxsci/kfn077 . PMID   18411233.
  20. ↑ Kembra L. Howdeshell; et al. (2008). "Mechanisms of action of phthalate esters, individually and in combination, to induce abnormal reproductive development in male laboratory rats". Environmental Research. 108 (2): 168–176. Bibcode:2008ER....108..168H. doi: 10.1016/j.envres.2008.08.009 . PMID   18949836.
  21. ↑ Shanna H. Swan (2008). "Environmental phthalate exposure in relation to reproductive outcomes and other health endpoints in humans". Environmental Research. 108 (2): 177–184. Bibcode:2008ER....108..177S. doi:10.1016/j.envres.2008.08.007. PMC   2775531 . PMID   18949837.
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