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Bis(2-ethylhexyl) phthalate

Bis(2-ethylhexyl) phthalate
Bis(2-ethylhexyl) phthalate
Names
Preferred IUPAC name
Bis(2-ethylhexyl) benzene-1,2-dicarboxylate
Other names
Bis(2-ethylhexyl) phthalate
Di-sec octyl phthalate
DEHP
Octyl phthalate
Identifiers
117-81-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17747 N
ChEMBL ChEMBL402794 N
ChemSpider 8040 YesY
ECHA InfoCard 100.003.829
KEGG C03690 YesY
UNII C42K0PH13C YesY
Properties
C24H38O4
Molar mass 390.56 g·mol−1
Appearance colorless, oily liquid
Density 0.99 g/mL (20°C)
Melting point −50 °C (−58 °F; 223 K)
Boiling point 385 °C (725 °F; 658 K)
0.00003% (23.8°C)
Vapor pressure <0.01 mmHg (20°C)
Hazards
Main hazards Carcinogen, irritant, teratogen
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 216 °C; 420 °F; 489 K (open cup)
Explosive limits 0.3%-?
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 34,000 mg/kg (oral, rabbit)
26,000 mg/kg (oral, guinea pig)
30,600 mg/kg (oral, rat)
30,000 mg/kg (oral, mouse)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 5 mg/m3
REL (Recommended)
 Ca TWA 5 mg/m3 ST 10 mg/m3
IDLH (Immediate danger)
 Ca [5000 mg/m3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, DEHP; dioctyl phthalate, DOP), is an organic compound with the formula C8H4(C8H17COO)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. Accounting for an almost 54% market share in 2010, DEHP is a High Production Volume Chemical.

Due to its suitable properties and the low cost, DEHP is widely used as a plasticizer in manufacturing of articles made of PVC. Plastics may contain 1% to 40% of DEHP. It is also used as a hydraulic fluid and as a dielectric fluid in capacitors. DEHP also finds use as a solvent in glowsticks.

Approximately three billion kilograms are produced annually worldwide. It is estimated that at least 241 million pounds of dioctyl phthalates were produced in the US in 1999, so DEHP is a High Production Volume Chemical. Four companies operating five facilities are the primary U.S. producers of DEHP: Aristech Chemical Company in Neville Island, Pennsylvania; Hatco Chemical Company in Fords, New Jersey; Teknor Apex Company in Brownsville, Tennessee and Hebronville, Massachusetts; and Tennessee Eastman Company in Kingsport, Tennessee.

Industrial production entails the reaction of phthalic anhydride with 2-ethylhexanol:


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