 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Dibutyl benzene-1,2-dicarboxylate | |
| Other names Dibutyl phthalate Di-n-butyl phthalate Butyl phthalate, dibasic (2:1) n-Butyl phthalate 1,2-Benzenedicarboxylic acid dibutyl ester o-Benzenedicarboxylic acid dibutyl ester DBP Palatinol C Elaol Dibutyl 1,2-benzene-dicarboxylate | |
| Identifiers | |
| |
3D model (JSmol) | |
| 1914064 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| DrugBank | |
| ECHA InfoCard | 100.001.416 |
| EC Number |
|
| 262569 | |
| KEGG |
|
| RTECS number |
|
| UNII | |
| |
| |
| Properties | |
| C16H22O4 | |
| Molar mass | 278.348 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | aromatic |
| Density | 1.05 g/cm3 at 20 °C |
| Melting point | −35 °C (−31 °F; 238 K) |
| Boiling point | 340 °C (644 °F; 613 K) |
| 13 mg/L (25 °C) | |
| logP | 4.72 |
| Vapor pressure | 0.00007 mmHg (20 °C)[1] |
| −175.1·10−6 cm3/mol | |
| Pharmacology | |
| P03BX03 (WHO) | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | N), Harmful (Xi) |
| GHS labelling: | |
  | |
| Danger | |
| H360Df,H400 | |
| P201,P202,P273,P281,P308+P313,P391,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 157 °C (315 °F; 430 K) (closed cup) |
| 402 °C (756 °F; 675 K) | |
| Explosive limits | 0.5 - 3.5% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 5289 mg/kg (oral, mouse) 8000 mg/kg (oral, rat) 10,000 mg/kg (oral, guinea pig)[2] |
LC50 (median concentration) | 4250 mg/m3 (rat) 25000 mg/m3 (mouse, 2 hr)[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 5 mg/m3[1] |
REL (Recommended) | TWA 5 mg/m3[1] |
IDLH (Immediate danger) | 4000 mg/m3[1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Dibutyl phthalate (DBP) is anorganic compound ofphthalate which is commonly used as aplasticizer because of its low toxicity and wide liquid range. With thechemical formula C6H4(CO2C4H9)2, it is a colorless oil, although impurities often render commercial samples yellow.[3] Dibutyl phthalate has highdielectric constant.
DBP is produced by the reaction ofn-butanol withphthalic anhydride.[3] DBP is an important plasticizer that enhances the utility of some major engineering plastics, such as PVC. Such modified PVC is widely used in plumbing for carrying sewage and other corrosive materials.[3]
Hydrolysis of DBP leads tophthalic acid and1-butanol.[4]Monobutyl phthalate (MBP) is its major metabolite.[5]
Biodegradation by microorganisms represents one route for remediation of DBP. For example,Enterobacter species can biodegrade municipal solid waste—where the DBP concentration can be observed at 1500 ppm—with ahalf-life of 2–3 hours. In contrast, the same species can break down 100% ofdimethyl phthalate after a span of six days.[6] The white rot fungusPolyporus brumalis degrades DBP.[7]DBP is leached from landfills.[8]
As reflected by itsoctanol-water partition coefficient of around 4, it is lipophilic, which means that it is not readily mobilized (dissolved by) water. Nonetheless, dissolved organic compounds (DOC) increase its mobility inlandfills.[9][10]
DBP has a lowvapor pressure of 2.67 x 10−3 Pa. Thus DBP does not evaporate readily (hence its utility as a plasticizer).[11] TheHenry's Law constant is 8.83 x 10−7 atm-m3/mol.[4]
DBP is regarded as anendocrine disruptor.[12]
The use of this substance in cosmetics, including nail polishes, is banned in theEuropean Union underDirective 76/768/EEC 1976.[13]
The use of DBP has been restricted in the European Union for use in children's toys since 1999.[14]
An EU Risk Assessment has been conducted on DBP and the outcome has now been published in the EU Official Journal. To eliminate a potential risk to plants in the vicinity of processing sites and workers through inhalation, measures are to be taken within the framework of the IPPC Directive (96/61/EC) and the Occupational Exposure Directive (98/24/EC)[15] Also includes the 2004 addendum.
Based on urine samples from people of different ages, the European CommissionScientific Committee on Health and Environmental Risks (SCHER) concluded that total exposures to DBP should be further reduced.[16]
UnderEuropean UnionDirective 2011/65/EU[17] revision 2015/863,[18] DBP is limited to max 1000 ppm concentration in any homogenous material.
Dibutyl phthalate (DBP) is one of the sixphthalic acid esters found on the Priority Pollutant List, which consists of pollutants regulated by theUnited States Environmental Protection Agency (U.S. EPA).[19]
DBP was added to theCalifornia Proposition 65 (1986) list of suspectedteratogens in November 2006. It is a suspectedendocrine disruptor.[12] It was used in many consumer products, e.g.,nail polish, but such usages has declined since around 2006. It was banned in children's toys, in concentrations of 1000 ppm or greater, under section 108 of theConsumer Product Safety Improvement Act of 2008 (CPSIA).
Phthalates are noncorrosive with low acute toxicity.[3]
{{cite journal}}:Cite journal requires|journal= (help)