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Diisobutyl phthalate ( CASNO:84-69-5 )

Identification and Related Records
Name:
Diisobutyl phthalate
CAS Registry number:
84-69-5
Synonyms:
DIBP
1,2-benzenedicarboxylic acid bis(2-methylpropyl) ester
phthalic acid diisobutyl ester
DIBP
EINECS(EC#):
201-553-2
Molecular Formula:
C16H22O4
Molecular Weight:
278.34
Inchi:
InChI=1/C16H22O4/c1-11(2)9-19-15(17)13-7-5-6-8-14(13)16(18)20-10-12(3)4/h5-8,11-12H,9-10H2,1-4H3
InChIKey:
MGWAVDBGNNKXQV-UHFFFAOYSA-N
Canonical SMILES:
CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C
Chemical and Physical Properties
Appearance:
Clear, colorless, viscous liquid.
Density:
1.038
Melting Point:
-64℃
Boiling Point:
327℃
Refractive Index:
1.489-1.491
Flash Point:
185℃
Water:
Insoluble
Solubilities:
Insoluble
Color/Form:
Liquid
Stability:
Stable under normal temperatures and pressures.
HS Code:
29173400
Storage temp:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Spectral properties:
Index of refraction: 1.4900 at 25 deg C/D
Raman: 79 (Sadtler Research Laboratories IR Grating Collection)
IR: 367 (Sadtler Research Laboratories IR Grating Collection)
UV: 955 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 709 (Sadtler Research Laboratories Spectral Collection)
MASS: 71639 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
Computed Properties:
Molecular Weight:278.34348 [g/mol]
Molecular Formula:C16H22O4
XLogP3:4.1
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:8
Exact Mass:278.151809
MonoIsotopic Mass:278.151809
Topological Polar Surface Area:52.6
Heavy Atom Count:20
Formal Charge:0
Complexity:290
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
Feature 3D Acceptor Count:2
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:8
Conformer Sampling RMSD:0.8
CID Conformer Count:143
Safety and Handling
Hazard Codes:
Xn:Harmful
Risk Statements:
R50/53;R62;R63
Safety Statements:
S36/37;S61
HazardClass:
9
PackingGroup:
III
Transport:
UN 3082
Fire Fighting Procedures:
Alcohol foam. Water or foam may cause frothing.
Fire Potential:
Combustible
Formulations/Preparations:
The water based adhesive may contain typically up to 15% DIBP. ...
Exposure Standards and Regulations:
Diisobutyl phthalate is an indirect food additive for use only as a component of adhesives.
Other Preventative Measures:
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Octanol/Water Partition Coefficient:
log Kow = 4.11
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Use and Manufacturing
Use and Manufacturing:
U.S. Production

1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >1 million - 10 million 1990 >1 million - 10 million 1994 >1 million - 10 million 1998 >1 million - 10 million 2002 >500 thousand - 1 million
Usage:
Plasticizer.
Biomedical Effects and Toxicity
Biomedical Effects and Toxicity:
This study examined the extent of dermal absorption of a series of phthalate diesters in the rat. Those tested were dimethyl, diethyl, dibutyl, diisobutyl, dihexyl, di(2-ethylhexyl), diisodecyl, and benzyl butyl phthalate. Hair from a skin area (1.3 cm in diameter) on the back of male F344 rats was clipped, the 14(C)phthalate diester was applied in a dose of 157 mumol/kg, and the area of application was covered with a perforated cap. The rat was restrained and housed for 7 days in a metabolic cage that allowed separate collection of urine and feces. Urine and feces were collected every 24 hr, and the amount of (14)C excreted was taken as an index of the percutaneous absorption. At 24 hr, diethyl phthalate showed the greatest excretion (26%). As the length of the alkyl side chain increased, the amount of (14)C excreted in the first 24 hr decreased signficantly. The cumulative percentage dose excreted in 7 days was greatest for diethyl, dibutyl, and diisobutyl phthalate, about 50-60% of the applied (14)C; an intermediate (20-40%) for dimethyl, benzyl butyl, and dihexyl phthalate. Urine was the major route of excretion of all phthalate diesters except for diisodecyl phthalate. This compound was poorly absorbed and showed almost no urinary excretion. After 7 days, the percentage dose for each phthalate that remained in the body was minimal showed no specific tissue distribution. Most of the unexcreted dose remained in the area of application. These data show that the structure of the phthalate diester determines the degree of dermal absorption. Absorption maximized with diethyl phthalate and then decreased significantly as the alkyl side chain length increased. [Elsisi AE et al; Fundam Appl Toxicol 12 (1): 70-7 (1989)] PubMed Abstract
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
The rate constant for the vapor-phase reaction of diisobutyl phthalate with photochemically-produced hydroxyl radicals has been estimated as 9.3X10-12 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 42 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 4.1 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 5.3 years and 190 days at pH values of 7 and 8, respectively(2). Diisobutyl phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
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