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Dibutyl phthalate

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Dibutyl phthalate
Names
Preferred IUPAC name
Dibutyl benzene-1,2-dicarboxylate
Other names
Dibutyl phthalate
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.416 Edit this at Wikidata
EC Number
  • 201-557-4
KEGG
RTECS number
  • TI0875000
UNII
  • InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 ☒N
    Key: DOIRQSBPFJWKBE-UHFFFAOYSA-N ☒N
  • CCCCOC(=O)c1ccccc1C(=O)OCCCC
Properties
C16H22O4
Molar mass 278.348 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
P03BX03 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 N), Harmful (Xi)
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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
2
1
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]
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 their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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. DBP is also a putative endocrine disruptor[3]

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.[4]

The use of DBP has been restricted in the European Union for use in children's toys since 1999.[5]

United States

DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor.[3] 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.[6]

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.[7]

Biodegradation

The white rot fungus Polyporus brumalis degrades DBP.[8]

See also

References

  1. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0187". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Dibutyl Phthalate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b Williams MJ, Wiemerslage L, Gohel P, Kheder S, Kothegala LV, Schiöth HB (2016). "Dibutyl Phthalate Exposure Disrupts Evolutionarily Conserved Insulin and Glucagon-Like Signaling in Drosophila Males". Endocrinology. doi:10.1210/en.2015-2006. PMID 27100621.
  4. ^ EU Council Directive 76/768/EEC of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic products
  5. ^ Ban of phthalates in childcare articles and toys, press release IP/99/829, 10 November 1999
  6. ^ "Eastman Announces Discontinuation of Manufacture of DEP and DBP Plasticizers". Eastman. 16 March 2011.
  7. ^ "Phthalates in school supplies". GreenFacts Website. Retrieved 10 June 2009.
  8. ^ Ishtiaq Ali, Muhammad (2011). Microbial degradation of polyvinyl chloride plastics (PDF) (Ph.D.). Quaid-i-Azam University. p. 48.

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