Dibutyl phthalate

Dibutyl phthalate
Names
IUPAC name
Dibutyl phthalate
Other names
Di-n-butyl phthalate, Butyl phthalate, n-Butyl phthalate, 1,2-Benzenedicarboxylic acid dibutyl ester, o-Benzenedicarboxylic acid dibutyl ester, DBP, Palatinol C, Elaol, Dibutyl-1,2-benzene-dicarboxylate
Identifiers
84-74-2 YesY
ChEBI CHEBI:34687 N
ChEMBL ChEMBL272485 N
ChemSpider 13837319 N
EC Number 201-557-4
6295
Jmol interactive 3D Image
KEGG C14214 N
PubChem 3026
RTECS number TI0875000
UNII 2286E5R2KE YesY
Properties
C16H22O4
Molar mass 278.35 g·mol−1
Appearance Colorless to faint yellow oily 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)
log P 4.72
Vapor pressure 0.00007 mmHg (20°C)[1]
Pharmacology
ATC code P03BX03
Hazards
Main hazards N), Harmful (Xi)
R-phrases R50 R61 R62
S-phrases S45 S53 S61
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 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform 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
1
2
0
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):
5289 mg/kg (oral, mouse)
8000 mg/kg (oral, rat)
10,000 mg/kg (oral, guinea pig)[2]
4250 mg/m3 (rat)
25000 mg/m3 (mouse, 2 hr)[2]
US health exposure limits (NIOSH):
TWA 5 mg/m3[1]
TWA 5 mg/m3[1]
4000 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. It is soluble in various organic solvents, e.g. in alcohol, ether and benzene. DBP is also used as an ectoparasiticide.

Legislative control

European Union

The use of this substance in cosmetics, including nail polishes, is banned in the European Union under Directive 76/768/EEC 1976.[3]

The use of DBP has been restricted in the European Union for use in children's toys since 1999.[4]

United States

DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. It was used in some nail polishes; all major producers began eliminating this chemical from nail polishes in the Fall of 2006.

DBP was permanently banned in children's toys, in concentrations of 1000 ppm or greater, under section 108 of the Consumer Product Safety Improvement Act of 2008 (CPSIA).

Production

DBP is produced by the reaction of n-butanol with phthalic anhydride. It is or was produced in the United States by Eastman Chemical Company, but the company announced in March 2011 that it would end production and exit the DBP and DEP (diethyl phthalate) market in December 2011.[5]

Exposure

Based on urine samples from people of different ages, the European Commission Scientific Committee on Health and Environmental Risks (SCHER) concluded that total exposures to individual phthalates in the general population are below tolerable daily intakes (TDI), except in the case of DBP for which efforts to further reduce exposures are needed.[6]

Biodegradation

The white rot fungus Polyporus brumalis degrades DBP. [7]

See also

References

  1. 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0187". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 "Dibutyl Phthalate". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ EU Council Directive 76/768/EEC of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic products
  4. ↑ Ban of phthalates in childcare articles and toys, press release IP/99/829, 10 November 1999
  5. ↑ "Eastman Announces Discontinuation of Manufacture of DEP and DBP Plasticizers". Eastman. 16 March 2011.
  6. ↑ "Phthalates in school supplies". GreenFacts Website. Retrieved 2009-06-10.
  7. ↑ Ishtiaq Ali, Muhammad (2011). Microbial degradation of polyvinyl chloride plastics (PDF) (Ph.D.). Quaid-i-Azam University. p. 48.

External links

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