Dibutyl Phthalate

Compound Structure:

Synonyms:

dibutyl phthalate;84-74-2;Di-n-butyl phthalate;n-Butyl phthalate;Butyl phthalate;Genoplast B;Palatinol C;Celluflex ; Dibutyl 1,2-benzenedicarboxylate;Phthalic acid dibutyl ester;dibutyl benzene-1,2-dicarboxylate;1,2-Benzenedicarboxylic acid, dibutyl ester

Compound ID:

NMPC-018

PubChem ID:

3026

Molecular Formula:

C16H22O4

Canonical SMILES:

CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC

InChIKey:

DOIRQSBPFJWKBE-UHFFFAOYSA-N

About the compound:

Dibutyl phthalate (DBP) is an organic compound extensively utilized as a plasticizer due to its minimal toxicity and broad liquid range. Its chemical structure is denoted by the formula C6H4(CO2C4H9)2, and in its pure form, it appears as a colorless oil. However, commercial samples of DBP often exhibit a yellowish hue due to the presence of impurities. DBP is synthesized through a chemical reaction involving n-butanol and phthalic anhydride. It plays a critical role as a plasticizer, particularly in enhancing the properties of key engineering plastics like PVC (polyvinyl chloride). PVC that has been modified with DBP finds extensive use in plumbing systems, especially for transporting sewage and other corrosive materials, due to its improved utility. When DBP undergoes hydrolysis, it breaks down into phthalic acid and 1-butanol. A significant metabolite of DBP is monobutyl phthalate (MBP). The biodegradation of DBP, particularly through microbial action, is a vital process for its environmental remediation. Certain microorganisms, such as species of Enterobacter, are capable of biodegrading DBP in municipal solid waste, where its concentration might reach as high as 1500 ppm. In these conditions, DBP has a half-life of about 2-3 hours. Interestingly, these microorganisms can completely degrade dimethyl phthalate over a period of six days. Additionally, the white rot fungus Polyporus brumalis is known for its ability to degrade DBP. Another environmental concern is the leaching of DBP from landfills, highlighting the importance of understanding and managing its lifecycle in various ecosystems.

Safety and Hazard

GHS Hazard Statements

H360Df: May damage the unborn child; Suspected of damaging fertility [Danger Reproductive toxicity]

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Properties:

Chemical and Physical Properties

Property Name	Property Value
Molecular Weight	278.34 g/mol
XLogP3	4.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	10
Exact Mass	278.15180918 g/mol
Monoisotopic Mass	278.15180918 g/mol
Topological Polar Surface Area	52.6Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	271
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes
Physical appearance	N-butyl phthalate is a colorless oily liquid. It is insoluble in water. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Since it is a liquid it can easily penetrate the soil and contaminate groundwater and nearby streams. It is combustible though it may take some effort to ignite. It is used in paints and plastics and as a reaction media for chemical reactions. Tastes strong and bitter
Boiling Point	644 °F at 760 mmHg (NTP, 1992)
Melting Point	-31 °F (NTP, 1992)
Density	1.049 at 68 °F (USCG, 1999)
Solubility	less than 1 mg/mL at 68 °F (NTP, 1992)
Vapor Pressure	1 mmHg at 297 °F ; 1.1 mmHg at 302 °F (NTP, 1992)

Source: PubChem

Source Species:

Anacardium occidentale
Annona senegalensis
Crateva adansonii
Musa sapientum
Nymphaea lotus
Spondias mombin
Terminalia superba
Musa acuminata
Grewia mollis

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