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84-74-2

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Identification

Name
Dibutyl phthalate
CAS
84-74-2
Synonyms
1,2-benzenedicarboxylic acid dibutyl ester
ARALDITE RESIN
Benzenedicarboxylic acid dibutyl ester
BUTYL PHTHALATE
DBP
DBP(R)
DIBUTYL 1,2-BENZENEDICARBOXYLATE
DIBUTYL PHTHALATE
DI-N-BUTYL PHTHALATE
DL-N-BUTYL PHTHALATE
N-BUTYL PHTHALATE
O-BENZENEDICARBOXYLIC ACID DIBUTYL ESTER
PHTHALIC ACID, BIS-BUTYL ESTER
PHTHALIC ACID DIBUTYL ESTER
PHTHALIC ACID DI-N-BUTYL ESTER
ai-3-00283
benzene-1,2-dicarboxylicaciddibutylester
Benzene-o-dicarboxylic acid, di-n-butyl ester
benzene-o-dicarboxylicaciddi-n-butylester
Bufa
EINECS(EC#)
201-557-4
Molecular Formula
C16H22O4
MDL Number
MFCD00282537
Molecular Weight
278.34
MOL File
84-74-2.mol

Chemical Properties

Appearance
clear liquid
Melting point 
-35 °C
mp 
-35 °C
Boiling point 
340 °C(lit.)

bp 
340 °C(lit.)

density 
1.043 g/mL at 25 °C(lit.)

vapor density 
9.6 (vs air)

vapor pressure 
1 mm Hg ( 147 °C)

refractive index 
n20/D 1.492(lit.)

Fp 
340 °F

storage temp. 
2-8°C
solubility 
Very soluble in alcohol, ether, acetone, benzene
form 
Liquid
color 
APHA: ≤10
Specific Gravity
1.049 (20/20℃)
Relative polarity
0.272
explosive limit
0.47%, 236°F
Water Solubility 
Slightly soluble. 0.0013 g/100 mL
FreezingPoint 
-35℃
Merck 
14,3035
BRN 
1914064
Henry's Law Constant
6.3 x 10-5 atm?m3/mol (quoted, Petrasek et al., 1983)
Exposure limits
NIOSH REL: TWA 5 mg/m3, IDLH 4,000 mg/m3; OSHA PEL: TWA 5 mg/m3; ACGIH TLV: TWA 5 mg/m3.
InChIKey
DOIRQSBPFJWKBE-UHFFFAOYSA-N
Contact allergens
It is mainly used as a nonreactive epoxy diluent.
Uses
Di-n-butyl phthalate has been used as an insect repellant.
CAS DataBase Reference
84-74-2(CAS DataBase Reference)
NIST Chemistry Reference
Dibutyl phthalate(84-74-2)
EPA Substance Registry System
84-74-2(EPA Substance)

Hazard Information

Chemical Properties
clear liquid
Uses
A phthalate metabolite with genotoxic effect.
Uses
Plasticizer
Uses
Plasticizer; solvent for oil-soluble dyes, insecticides and other organics; antifoam agent; textile fiber lubricant; fragrance fixative; insect repellent.
Definition
ChEBI: A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol.
General Description
N-BUTYL PHTHALATE(84-74-2) is a colorless oily liquid. N-BUTYL PHTHALATE(84-74-2) 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 N-BUTYL PHTHALATE(84-74-2) is a liquid N-BUTYL PHTHALATE(84-74-2) can easily penetrate the soil and contaminate groundwater and nearby streams. N-BUTYL PHTHALATE(84-74-2) is combustible though N-BUTYL PHTHALATE(84-74-2) may take some effort to ignite. N-BUTYL PHTHALATE(84-74-2) is used in paints and plastics and as a reaction media for chemical reactions.
Reactivity Profile
N-BUTYL PHTHALATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Avoid contact with strong oxidizing agents and strong bases. Will not polymerize. [USCG, 1999]. Can generate electrostatic charges. [Handling Chemicals Safely 1980. p. 250].
Air & Water Reactions
Insoluble in water.
Fire Hazard
Combustible.
Description
Dibutyl phthalate is included as an insect repellent in some aerosol sprays used to treat flystrike in sheep. It is colorless oily liquid with a very weak aromatic odor.
Physical properties
Colorless to pale yellow, oily, viscous liquid with a mild, aromatic odor
Production Methods
Dibutyl phthalate is produced from n-butanol and phthalic anhydride in an ester formation reaction.
Health Hazard
The toxicity of this compound is very low. Inhumans, oral intake of dibutyl phthalate at adose level of 150 mg/kg may cause nausea,vomiting, dizziness, hallucination, distortedvision, lacrimation, and conjunctivitis withprompt recovery. It metabolizes to monobutylester and phthalic acid and is excreted in urine.The inhalation toxicity should be insignificantbecause of its negligible low vapor pressure[<0.1 torr at 20°C (68°F)]. However, expo sure to its mist or aerosol can cause irritationof eyes and mucous membranes
LD50 value, oral (mice): 5300 mg/kg.
Pharmaceutical Applications
Dibutyl phthalate is used in pharmaceutical formulations as a plasticizer in film-coatings. It has been evaluated as a pore-forming agent in novel delivery systems.It is also used extensively as a solvent, particularly in cosmetic formulations such as antiperspirants, hair shampoos, and hair sprays. In addition to a number of industrial applications, dibutyl phthalate is used as an insect repellent, although it is not as effective as dimethyl phthalate.
Safety
Dibutyl phthalate is generally regarded as a relatively nontoxic material, although it has occasionally been reported to cause hypersensitivity reactions. It is widely used in topical cosmetic and some oral pharmaceutical formulations.
LD50 (mouse, IV): 0.72g/kg
LD50 (mouse, oral): 5.3g/kg
LD50 (rat, oral): 8.0g/kg
LD50 (rat, IP): 3.05mL/kg
Source
Detected in distilled water-soluble fractions of new and used motor oil at concentrations of 38 to 43 and 15 to 23 μg/L, respectively (Chen et al., 1994). Leaching from flexible plastics in contact with water. Laboratory contaminant.
Environmental Fate
Biological. Under aerobic conditions using a freshwater hydrosol, mono-n-butyl phthalate and phthalic acid were produced. Under anaerobic conditions, phthalic acid was not present (Verschueren, 1983). In anaerobic sludge, di-n-butyl phthalate degraded as follows: monobutyl phthalate to phthalic acid to protocatechuic acid followed by ring cleavage and mineralization (Shelton et al., 1984). Engelhardt et al. (1975) reported that a variety of microorganisms were capable of degrading of di-n-butyl phthalate and suggested the following degradation scheme: di-n-butyl phthalate to mono-n-butyl phthalate to phthalic acid to 3,4-dihydroxybenzoic acid and other unidentified products. Di-n-butyl phthalate was degraded to benzoic acid by tomato cell suspension cultures (Lycopericon lycopersicum) (Pogány et al., 1990).
In a static-culture-flask screening test, di-n-butyl phthalate showed significant biodegradation with rapid adaptation. The ester (5 and 10 mg/L) was statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum. After 7 days, 100% biodegradation was achieved (Tabak et al., 1981).
Soil. Under aerobic conditions using a fresh-water hydrosol, mono-n-butyl phthalate and phthalic acid were produced. Under anaerobic conditions, however, phthalic acid was not formed (Verschueren, 1983).
Photolytic. An aqueous solution containing titanium dioxide and subjected to UV radiation (l >290 nm) produced hydroxyphthalates and dihydroxyphthalates as intermediates (Hustert and Moza, 1988).
Chemical/Physical. Pyrolysis of di-n-butyl phthalate in the presence of polyvinyl chloride at 600°C gave the following compounds: indene, methylindene, naphthalene, 1- methylnaphthalene, 2-methylnaphthalene, biphenyl, dimethylnaphthalene, acenaphthene, fluorene, methylacenaphthene, methylfluorene and six unidentified compounds (Bove and Dalven, 1984).
Under alkaline conditions, di-n-butyl phthalate will initially hydrolyze to n-butyl hydrogen phthalate and n-butanol. The monoester will undergo further hydrolysis forming o-phthalic acid and n-butanol (Kollig, 1993).
storage
Dibutyl phthalate should be stored in a well-closed container in a cool, dry, location. Containers may be hazardous when empty since they can contain product residues such as vapors and liquids.
Purification Methods
Wash DBP with H2O (to free it from alcohol), then dilute NaOH (to remove any butyl hydrogen phthalate or acid), aqueous NaHCO3 (charcoal), then distilled water. Dry it (CaCl2), distil it at 10torr or less, and store it in a desiccator over P2O5. [Beilstein 9 II 586, 9 III 4102, 9 IV 3175.]
Toxicity evaluation
Acute oral LD50 for rats: >6,000 mg/kg
Incompatibilities
Dibutyl phthalate reacts violently with chlorine. It also reacts with oxidizing agents, acids, bases, and nitrates.
Regulatory Status
Included in the FDA Inactive Ingredients Database (oral capsules, delayed action, enteric coated, and controlled release tablets). Included in nonparenteral medicines licensed in the UK (oral capsules, tablets, granules; topical creams and solutions).

Safety Data

Hazard Codes 
T,N,F
Risk Statements 
R61:May cause harm to the unborn child.
R50:Very Toxic to aquatic organisms.
R62:Possible risk of impaired fertility.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable.
Safety Statements 
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37:Wear suitable protective clothing and gloves .
S16:Keep away from sources of ignition-No smoking .
RIDADR 
UN 3082 9/PG 3

WGK Germany 
2

RTECS 
TI0875000

Autoignition Temperature
756 °F
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29173100
Safety Profile
Moderately toxic by intraperitoneal and intravenous routes. Mildly toxic by ingestion. Human systemic eye effects by ingestion, hallucinations, dstorted perceptions, nausea or vomiting, and kidney, ureter, or bladder changes. Experimental teratogenic and reproductive effects. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidizing materials. Violent reaction with Cl2. Incompatible with chlorine. To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also ESTERS, PHTHALIC ACID, and n BUTYL ALCOHOL.
Hazardous Substances Data
84-74-2(Hazardous Substances Data)
Toxicity
Acute oral LD50 for rats 8,000 mg/kg (RTECS, 1985).

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