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
C12H14O4
Molar mass 222.24 g/mol
AppearanceColourless, oily liquid
Density 1.12 g/cm3 at 20 °C
Melting point −4 °C (25 °F; 269 K)
Boiling point 295 °C (563 °F; 568 K)
1080 mg/L at 25 °C
log P 2.42
Vapor pressure 0.002 mmHg (25 °C) [2]
−127.5·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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
1
1
0
Flash point 161.1 °C (322.0 °F; 434.2 K) [2]
Explosive limits 0.7%, lower [2]
Lethal dose or concentration (LD, LC):
8600 mg/kg (rat)
NIOSH (US health exposure limits):
PEL (Permissible)
None [2]
REL (Recommended)
TWA 5 mg/m3 [2]
IDLH (Immediate danger)
N.D. [2]
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. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.

Contents

Synthesis and applications

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

Synthesis-DEP.png

It finds some use as a specialist plasticiser in PVC, it has also been used as a blender and fixative in perfume. [3]

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. Thus there exists an alternative pathway of biodegradation which includes transesterification or demethylation by microorganisms, if the soil is also contaminated with methanol, that would produce another three intermediate compounds, ethyl methyl phthalate, dimethyl phthalate and monomethyl phthalate. This biodegradation has been observed in several soil bacteria. [4] Some bacteria with these abilities have specific enzymes involved in the degradation of phthalic acid esters such as phthalate oxygenase, phthalate dioxygenase, phthalate dehydrogenase and phthalate decarboxylase. [5] The developed intermediates of the transesterification or demethylation, ethyl methyl phthalate and dimethyl phthalate, enhance the toxic effect and are able to disrupt the membrane of microorganisms.

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. [5]

Toxicity

Little is known about the chronic toxicity of diethyl phthalate, but existing information suggests only a low toxic potential. [6] 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. [7] [8] [9] [10] Dose response experiments in fiddler crabs have shown that seven-day exposure to diethyl phthalate at 50 mg/L significantly inhibited the activity of chitobiase in the epidermis and hepatopancreas. [11] Chitobiase plays an important role in degradation of the old chitin exoskeleton during the pre-moult phase. [12]

Teratogenicity

When pregnant rats were treated with diethyl phthalate, it became evident that certain doses caused skeletal malformations, whereas the untreated control group showed no resorptions. The amount of skeletal malformations was highest at highest dose. [13] In a following study it was found that both phthalate diesters and their metabolic products were present in each of these compartments, suggesting that the toxicity in embryos and fetuses could be the result of a direct effect. [14]

Future investigation

Some data suggest that exposure to multiple phthalates at low doses significantly increases the risk in a dose additive manner. [15] [16] [17] 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. [18]

Related Research Articles

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<span class="mw-page-title-main">Phthalates</span> Any ester derived from phthalic acid

Phthalates, or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). Note that while phthalates are usually plasticizers, not all plasticizers are phthalates. The two terms are specific and unique and cannot be used interchangeably.

<span class="mw-page-title-main">Endocrine disruptor</span> Chemicals that can interfere with endocrine or hormonal systems

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Xenoestrogens are a type of xenohormone that imitates estrogen. They can be either synthetic or natural chemical compounds. Synthetic xenoestrogens include some widely used industrial compounds, such as PCBs, BPA, and phthalates, which have estrogenic effects on a living organism even though they differ chemically from the estrogenic substances produced internally by the endocrine system of any organism. Natural xenoestrogens include phytoestrogens which are plant-derived xenoestrogens. Because the primary route of exposure to these compounds is by consumption of phytoestrogenic plants, they are sometimes called "dietary estrogens". Mycoestrogens, estrogenic substances from fungi, are another type of xenoestrogen that are also considered mycotoxins.

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<span class="mw-page-title-main">Bis(2-ethylhexyl) phthalate</span> Organic compound used as a plasticizer to soften polymer matrix

Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, diisooctyl phthalate, DEHP; incorrectly — dioctyl phthalate, DIOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water.

<span class="mw-page-title-main">Benzyl butyl phthalate</span> Chemical compound

Benzyl butyl phthalate (BBP) is an organic compound historically used a plasticizer, but which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.

<span class="mw-page-title-main">2-Ethylhexanol</span> Chemical compound

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Diisobutyl phthalate (DIBP) is a phthalate ester having the structural formula C6H4(COOCH2CH 2)2. It is formed by the esterification of isobutanol and phthalic anhydride. This and other phthalates are used as plasticizers due to their flexibility and durability. They are found in many industrial and personal products, such as lacquers, nail polish and cosmetics. DIBP can be absorbed via oral ingestion and dermal exposure. When it comes to excretion, DIBP is first converted into the hydrolytic monoester monoisobutyl phthalate (MIBP). The primary excretory route is urine, with biliary excretion being noted in minor amounts. DIBP has lower density and freezing point than the related compound dibutyl phthalate (DBP).

<span class="mw-page-title-main">Dimethyl phthalate</span> Chemical compound

Dimethyl phthalate (DMP) is an organic compound and phthalate ester. it is a colourless and oily liquid that is soluble in organic solvents, but which is only poorly soluble in water.

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<span class="mw-page-title-main">Dibutyl phthalate</span> Chemical compound

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<span class="mw-page-title-main">Ecotoxicity</span>

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<span class="mw-page-title-main">Diisononyl phthalate</span> Chemical compound

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<span class="mw-page-title-main">Reproductive toxicity</span> A hazard associated with chemical substances

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Bis(2-ethylhexyl) terephthalate commonly abbreviated DEHT (Dioctyl terephthalate or DOTP), is an organic compound with the formula C6H4(CO2C8H17)2. It is a non-phthalate plasticizer, being the diester of terephthalic acid and the branched-chain 2-ethylhexanol, which is often generically referred to as octyl. This colorless viscous liquid is used for softening PVC plastics and is known for chemical similarity to general purpose phthalates such as DEHP and DINP, but without any negative regulatory pressure. It possesses very good plasticizing properties and may be used as a direct replacement for DEHP and DINP in many applications.

<span class="mw-page-title-main">Developmental toxicity</span>

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<span class="mw-page-title-main">Monobutyl phthalate</span> Chemical compound

Monobutyl phthalate (MBP) is an organic compound with the condensed structural formula CH3(CH2)3OOCC6H4COOH. It is a white solid that features both an butyl ester group and a carboxylic acid group. It is the major metabolite of dibutyl phthalate. Like many phthalates, MBP has attracted attention as a potential endocrine disruptor.

<span class="mw-page-title-main">Monobenzyl phthalate</span> Chemical compound

Monobenzyl phthalate (MBzP) also known as benzene-1, 2-dicarboxylic acid is an organic compound with the condensed structural formula C6H5CH2OOCC6H4COOH. It is the major metabolite of butyl benzyl phthalate(BBP), a common plasticizer. BBP can also be metabolized into monobutyl phthalate (MBP). Like many phthalates, BBP has attracted attention as a potential endocrine disruptor.

References

  1. ↑ "Chemical Information Profile for Diethyl Phthalate" (PDF). Integrated Laboratory Systems, Inc. Archived from the original (PDF) on 1 February 2009. Retrieved 3 March 2009.
  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0213". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ 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.
  4. ↑ 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.
  5. 1 2 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ Zou, Enmin; Fingerman, Milton (1999). "Effects of exposure to diethyl phthalate, 4-(tert)-octylphenol, and 2,4,5-trichlorobiphenyl on activity of chitobiase in the epidermis and hepatopancreas of the fiddler crab, Uca pugilator". Comparative Biochemistry and Physiology C. 122 (1): 115–120. doi:10.1016/S0742-8413(98)10093-2. PMID   10190035.
  12. ↑ M. A. Baars & S.S. Oosterhuis, "Free chitobiase, a marker enzyme for the growth of crustaceans", NIOZ Annual Report 2006 (PDF), Royal Netherlands Institute for Sea Research, Texel, pp. 62–64, archived from the original (PDF) on 2011-07-20
  13. ↑ A. R. Singh; W. H. Lawrence; J. Autian (1972). "Teratogenicity of Phthalate Esters in Rats". Journal of Pharmaceutical Sciences. 61 (1): 51–55. doi:10.1002/jps.2600610107. PMID   5058645.
  14. ↑ A. R. Singh; W. H. Lawrence; J. Autian (1975). "Maternal-Fetal transfer of 14C-Di-2-ethylhexyl phthalate and 14C-diethyl phthalate in rats". Journal of Pharmaceutical Sciences. 64 (8): 1347–1350. doi:10.1002/jps.2600640819. PMID   1151708.
  15. ↑ 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.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ 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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