Bis(2-ethylhexyl) terephthalate

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Bis(2-ethylhexyl) terephthalate
Bis(2-ethylhexyl) terephthalate.svg
Bis(2-ethylhexyl) terephthalate 3D BS.png
Names
IUPAC name
Bis(2-ethylhexyl) benzene-1,4-dicarboxylate
Other names
Dioctyl Terephthalate (archaic); [1] Bis(2-ethylhexyl) terephthalate; Di(ethylhexyl) terephthalate; 1,4-Benzenedicarboxylic acid bis(2-ethylhexyl) ester
Identifiers
3D model (JSmol)
AbbreviationsDEHT, DOTP
ChemSpider
ECHA InfoCard 100.026.524 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 229-176-9
MeSH C053316
PubChem CID
UNII
  • InChI=1S/C24H38O4/c1-5-9-11-19(7-3)17-27-23(25)21-13-15-22(16-14-21)24(26)28-18-20(8-4)12-10-6-2/h13-16,19-20H,5-12,17-18H2,1-4H3
  • O=C(OCC(CC)CCCC)c1ccc(C(=O)OCC(CC)CCCC)cc1
Properties
C24H38O4
Molar mass 390.564 g·mol−1
AppearanceClear viscous liquid
Density 0.984 g/mL
Melting point -63.5 °C
Boiling point 400 °C (752 °F; 673 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Non-toxic
Lethal dose or concentration (LD, LC):
5000 mg/kg (rats, orally) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

Production

One method of manufacture entails the transesterification of dimethyl terephthalate with 2-ethylhexanol:

C6H4(CO)2(OCH3)2 + 2 C8H17OH → C6H4(CO2 C8H17)2 + 2CH3OH

A second method of manufacture is a direct esterification of terephthalic acid with 2-ethylhexanol:

C6H4(CO2H)2 + 2 C8H17OH → C6H4(CO2 C8H17)2 + 2H2O

Use

DEHT is a general purpose plasticizer that is considered safer than ortho-phthalate plasticizers due to its reduced toxicity profile. The terephthalates exhibit none of the peroxisome proliferation of liver enzymes that some ortho-phthalates have shown in several studies. [3] It has uses in applications like extrusion, calendering, injection molding, rotational molding, dip molding, slush molding and coating. [4]

Alternative plasticizers

Several plasticizers offer similar technical properties to DEHT. These alternatives include phthalates such as DINP, DOP, DPHP, DIDP as well as non-phthalates such as DINCH and citrate esters.

Possible Health Effects

According to a panel appointed by the French Agency for the Safety of Health Products (ANSM), there is very little clinical assessment data regarding the toxicity, migration from Medical Devices, and population exposure of alternative plasticizers (e.g. DEHT/DOTP) and their metabolites. [5] The French government report concludes: "The presently available information indicates that DEHTP is not expected to pose any health or environmental risks. DEHTP is not considered as toxic for reproduction and no alert was found on potential endocrine disruption properties of the substance." [6]

Researchers from Korea state that: "DEHT, a phthalate [ sic ] ester stoichiometrically eqivaluent [ sic ] to DEHP, has been shown to have potential reproductive and developmental toxicity." [7] The NOAELs quoted are actually quite high, indicating the potential for reproductive toxicity is low. The same paper further states: "The ability of DEHT to induce anti-androgenic effects in male offspring was assessed by giving pregnant rats 750 mg/kg/d DEHT; no changes were observed." And further: "Results of a uterotrophic assay in which immature females were given up to 2,000 mg/kg/d DEHT indicate that this compound does not possess estrogenic activity."

Related Research Articles

<span class="mw-page-title-main">Polyethylene terephthalate</span> Polymer

Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.

<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">Phthalic acid</span> Aromatic organic compound with formula C6H4(COOH)2

In organic chemistry, phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2 and structure HO(O)C−C6H4−C(O)OH. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others being isophthalic acid and terephthalic acid.

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

<span class="mw-page-title-main">Plasticizer</span> Substance added to a material to make it softer and more flexible

A plasticizer is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.

<span class="mw-page-title-main">Terephthalic acid</span> Chemical compound

Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

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

Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(COOCH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.

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

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH3(C6H4(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.

<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

2-Ethylhexanol is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

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

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.

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

Diisononyl phthalate (DINP) is a phthalate used as a plasticizer. DINP is typically a mixture of chemical compounds consisting of various isononyl esters of phthalic acid, and is commonly used in a large variety of plastic products.

<span class="mw-page-title-main">1,2-Cyclohexane dicarboxylic acid diisononyl ester</span> Chemical compound

1,2-Cyclohexane dicarboxylic acid diisononyl ester (DINCH) is a mixture of organic compounds with the formula C6H10(CO2C9H19)2. DINCH is colorless oil. It is used as a plasticizer for the manufacture of flexible plastic articles in sensitive application areas such as toys, medical devices, and food packaging. It is of interest as an alternative for phthalate plasticizers, which are implicated as endocrine disruptors.

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

Diisodecyl phthalate (DIDP) is a commonly used plasticizer used in the production of plastic and plastic coating to increase flexibility. It is a mixture of compounds derived from the esterification of phthalic acid and isomeric decyl alcohols.

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

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.

<span class="mw-page-title-main">Tritan copolyester</span> Brand of copolymer

Tritan, a copolymer offered by the Eastman Chemical Company since 2007, is a transparent plastic intended to replace polycarbonate, because of health concerns about Bisphenol A (BPA). Tritan is a copolymer made from three monomers: dimethyl terephthalate (DMT), cyclohexanedimethanol (CHDM), and 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (CBDO). Tritan (PCTG) is made without using any bisphenols or phthalates.

Antiandrogens in the environment have become a topic of concern. Many industrial chemicals, including phthalates and pesticides, exhibit antiandrogen activity in animal experiments. Certain plant species have also been found to produce antiandrogens. In animal studies, environmental antiandrogens can harm reproductive organ development in fetuses exposed in utero as well as their offspring.

<span class="mw-page-title-main">Bis(2-ethylhexyl)tetrabromophthalate</span> Chemical compound

Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).

References

  1. ↑ DEHT: Trade names
  2. ↑ DEHT toxicity
  3. ↑ OECD SIDS Initial Assessment Report for SIAM 17 (2003)
  4. ↑ "Archived copy". Archived from the original on 2012-03-22. Retrieved 2011-04-11.{{cite web}}: CS1 maint: archived copy as title (link)
  5. ↑ Bui, Thuy T.; Giovanoulis, Georgios; Cousins, Anna Palm; Magnér, Jörgen; Cousins, Ian T.; de Wit, Cynthia A. (2016-01-15). "Human exposure, hazard and risk of alternative plasticizers to phthalate esters". Science of the Total Environment. 541: 451–467. Bibcode:2016ScTEn.541..451B. doi:10.1016/j.scitotenv.2015.09.036. PMID   26410720.
  6. ↑ French RMOA - DEHTP
  7. ↑ Kwon, Bareum; Ji, Kyunghee (2016). "Estrogenic and Androgenic Potential of Phthalates and Their Alternatives". Korean Journal of Environmental Health Sciences. 42 (3): 169–188. doi: 10.5668/JEHS.2016.42.3.169 .
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