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Diethyl phthalate ( CASNO:84-66-2 )
Identification and Related Records
- Diethyl phthalate
- CAS Registry number:
- Diethylester kyseliny ftalove [Czech]
o-Benzenedicarboxylic acid diethyl ester
1,2-Benzenedicarboxylic acid,esters,diethyl ester
4-09-00-03172 (Beilstein Handbook Reference)
Phthalic acid, diethyl ester
RCRA waste no. U088
Diethyl Phthalate [USAN]
o-Benzenedicarboxylic acid, diethyl ester
1,2-Benzenedicarboxylic acid, diethyl ester
Diethyl Phthalate 99%min
- Molecular Formula:
- Molecular Weight:
- Canonical SMILES:
Chemical and Physical Properties
- Water-white to colorless, odorless, oily liquid.
- Melting Point:
- -3 C
- Boiling Point:
- Refractive Index:
- Flash Point:
- 1 g/L (20℃)
- Insoluble Appearance:clear oily liquid
Hazard Symbols:9 (Packing Group: III) UN NO.
- Colorless oily liquid
Colorless to water-white, oily liquid.
- Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, alkalies.
- HS Code:
- Storage temp:
- Keep away from heat and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
- Spectral properties:
- Index of refraction: 1.5002 at 25 deg C/D
MAX ABSORPTION (ALCOHOL): 225 NM (LOG E= 3.9); 275 NM (LOG E= 3.1); SADTLER REFERENCE NUMBER: 375 (IR, PRISM); 117 (IR, GRATING)
Intense mass spectral peaks: 149 m/z (100%), 177 m/z (28%), 150 m/z (13%), 176 m/z (9%)
Intense mass spectral peaks: 222 m/z
IR: 4798 (Coblentz Society Spectral Collection)
Raman: 75 (Sadtler Research Laboratories Spectral Collection)
UV: 150 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 705 (Sadtler Research Laboratories Spectral Collection)
MASS: 22733 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 2-706 (Archives of Mass Spectral Data, John Wiley & Sons, New York)
- Computed Properties:
- Molecular Weight:222.23716 [g/mol]
Rotatable Bond Count:6
Topological Polar Surface Area:52.6
Heavy Atom Count:16
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 Ring Count:1
Effective Rotor Count:6
Conformer Sampling RMSD:0.8
CID Conformer Count:28
Safety and Handling
- Safety Statements:
- Skin, Eye, and Respiratory Irritations:
- DEP is slightly irritating to the eye and skin.
- Cleanup Methods:
- Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./
Environmental considerations-water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
Environmental considerations-air spill: Apply water spray or mist to knock down vapors.
- Fire Fighting Procedures:
- To fight fire, use water spray, mist, foam.
Use dry chemical, carbon dioxide, or foam extinguishers. Water or foam may cause frothing.
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.) Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.
Water or foam may cause frothing.
- Fire Potential:
- Grade: Technical
GRADE OF PURITY: TECHNICAL: 99+ %
- Exposure Standards and Regulations:
- Substances classified as plasticizers when migrating from food-packaging material includes diethyl phthalate.
Diethyl phthalate is an indirect food additive for use only as a component of adhesives.
- Reactivities and Incompatibilities:
- May attack some forms of plastics.
Strong oxidizers, strong acids, nitric acid, permanganates, water.
- Other Preventative Measures:
- If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.
Personnel protection: Keep upwind. Avoid breathing vapors.
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.
- Protective Equipment and Clothing:
- RUBBER GLOVES; GOGGLES OR FACE SHIELD.
Wear solvent-resistant protective gloves and clothing to prevent any reasonable probability of skin contact. ? Wear splash-proof chemical goggles and face shield unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.
Personnel protection: Wear appropriate chemical protective gloves, boots and goggles.
- The Diethyl phthalate, with the cas register number 84-66-2, is also called as diethyl-o-phthalate; ethyl phthalate; 'lgc' (2000); 1,2-benzenedicarboxylic acid diethyl ester; rarechem al bi 0044; phthalic acid, bis-ethyl ester; phthalic acid diethyl. The characteristics of this chemical could be summarized as: (1)ACD/LogP: 2.70; (2)ACD/LogD (pH 5.5): 2.7; (3)ACD/LogD (pH 7.4): 2.7 ; (4)ACD/BCF (pH 5.5): 66.38 ; (5)ACD/BCF (pH 7.4): 66.38 ; (6)ACD/KOC (pH 5.5): 701.19 ; (7)ACD/KOC (pH 7.4): 701.19 ; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 6 ; (10)Polar Surface Area: 52.6; (11)Index of Refraction: 1.507 ; (12)Molar Refractivity: 59.06 cm3 ; (13)Molar Volume: 198.2 cm3 ; (14)Polarizability: 23.41 ×10-24 cm3 ; (15)Surface Tension: 39.3 dyne/cm ; (16)Density: 1.121 g/cm3 ; (17)Flash Point: 155.8 °C ; (18)Enthalpy of Vaporization: 53.36 kJ/mol ; (19)Boiling Point: 294 °C at 760 mmHg? Vapour Pressure: 0.00167 mmHg at 25°C. This is a kind of colourless oily liquid, with little fragance. And it is complete soluble in ethanol and diethyl [ethyl] ether and soluble in? acetone, benzene and other organic solvent while insoluble in water. Besides, it is stable and combustible and then incompatible with strong oxidizing agents, strong acids, alkalies. While dealing with this chemical, avoid contact with skin and eyes, and you could also obtain more safety information from WGK Germany? 2. As for its usage, it is widely applied in many fields. It could be used as the fixative for spice and the plasticizer for alkyd resin, NBR, chloroprene rubber; it could also be as the rodenticide intermediate, such as diphacinone, pindone and Rozol and also the important dissolvant; it could also be used as dissolvant, plasticizer and lubricant for the analytical reagent and stationary liquid, cellulose and esters. When comes to its making method, it could be made from esterification of phthalic anhydride and alcohol. The specific way is below: prepare the phthalic anhydride and alcohol, and go through the reflux reaction with the existence of sulfuric acid(catalytic agent), and then get the crude products.? finally, have the distillation to get the ultimate products. As to its product categories, there are various, including phthalates; organics; analytical chemistry; environmental endocrine disruptors; functional materials; phthalates (environmental endocrine disruptors); phthalates (plasticizer); plasticizer. Additionally, you could convert the following data information into the molecular structure:
SMILES:O=C(OCC)c1ccccc1C(=O)OCC Below are the toxicity information of this chemical:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source guinea pig LD50 oral 8600mg/kg (8600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(3), Pg. 25, 1980. guinea pig LD50 subcutaneous 3gm/kg (3000mg/kg) ? "Industrial Hygiene and Toxicology," 2nd ed., Patty, F.A., ed., New York, John Wiley & Sons, Inc., 1958-63Vol. 2, Pg. 1904, 1963. guinea pig LD50 unreported 3gm/kg (3000mg/kg) ? Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(9), Pg. 26, 1990. human TCLo inhalation 1000mg/m3 (1000mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
LUNGS, THORAX, OR RESPIRATION: COUGH
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933. man TDLo oral 357uL/kg (0.357mL/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE
BEHAVIORAL: GENERAL ANESTHETIC
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 32, Pg. 1456, 1990. mouse LD50 intraperitoneal 2749mg/kg (2749mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
BLOOD: CHANGES IN SPLEEN
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 6, Pg. 342, 1947. mouse LD50 oral 6172mg/kg (6172mg/kg) ? Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 17(11), Pg. 51, 1973. mouse LD50 unreported 8600mg/kg (8600mg/kg) ? Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(7), Pg. 52, 1988.
- Octanol/Water Partition Coefficient:
- log Kow = 2.47
- Disposal Methods:
- [40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U088, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Good candidate for liquid injection incineration, with a temperature range of 650 to 1,600 deg C and a residence time of 0.1 to 2 seconds. Good candidate for rotary kiln incineration, with a temperature range of 820 to 1,600 deg C and a residence time of seconds. Also a good candidate for fluidized bed incineration, with a temperature range of 450 to 980 deg C and a residence time of seconds.
Atomize into an incinerator; combustion may be improved by mixing with a more flammable solvent. Recommendable methods: Incineration, landfill & use as boiler fuel. Peer-review: Adsorb on vermiculite or similar adsorbent and landfill. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
1. A gas-pipe the gas into the incinerator or lower into a pit and allow it to burn away. 2. A liquid-atomize into an incinerator. Combustion may be improved by mixing with a more flammable solvent. 3. A solid-make up packages in paper or other flammable material. Burn in the incinerator. Or the solid may be dissolved in a flammable solvent and sprayed into the fire chamber.
Use and Manufacturing
- Use and Manufacturing:
- Methods of Manufacturing
By reacting phthalic anhydride with ethanol followed by careful purificationU.S. Imports
(1978) 2.77X10+8 G (PRINCPL CUSTMS DISTS)
(1982) 2.32X10+8 G (PRINCPL CUSTMS DISTS)U.S. Production
(1977) 7.72X10+9 G
(1982) 7.72X10+9 G
(1985) 7.78X10+9 g
1,2-Benzenedicarboxylic acid, diethyl 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 >10 million - 50 million 1990 >10 million - 50 million 1994 >10 million - 50 million 1998 >10 million - 50 million 2002 >10 million - 50 millionConsumption Patterns
ALL PHTHALATE PLASTICIZERS: 89% IN POLYVINYL CHLORIDE RESINS; 3% IN OTHER VINYL RESINS; 3% IN CELLULOSE ESTER PLASTICS; 3% IN SYNTHETIC ELASTOMERS & OTHER POLYMERS; 2% IN OTHER APPLICATIONS (1974). /PHTHALATE ESTERS/
- In manufacture celluloid, solvent for cellulose acetate in manufacture varnishes & dopes, fixative for perfumes, denaturing alcohol.
Biomedical Effects and Toxicity
- Biomedical Effects and Toxicity:
- Absorption of diethyl phthalate and three other phthalates (dimethyl, dibutyl, and di(2-ethylhexyl)) was measured using human epidermal skin obtained from the abdominal skin of 11 cadavers (mostly females 55 years of age or older) and subcutaneous fat removed in vitro. Epidermal membranes were set up in glass diffusion cells, and their permeability to tritiated water was measured to establish the integrity of the skin. Lag time for absorption of diethyl phthalate was 6 hr, and the steady-state absorption rate was 12.8 ug/sq cm per hour.
Percutaneous absorption of diethyl phthalate was evaluated in vitro in flow-through diffusion cells using human breast skin. Neat chemical (16-21 mg/sq cm) was applied over 72 hr to the epidermal surface of the skin, which was either uncovered or covered. The absorption of diethyl phthalate through skin was 3.9% and 4.8% of the applied doses for covered and uncovered conditions, respectively. The interindividual variation was 4-fold, ranging from 1.6% (SD 1.2) (n = 3) to 8.7% (SD 3.9) (n = 6) among skin donors.
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; and 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
(14)C-Carboxy-labelled diethyl phthalate (2850 mg/kg body weight) was administered intraperitoneally to a group of 13 pregnant rats on either day 5 or day 10 of gestation. The results showed that radioactivity in the maternal blood peaked during the first 24 hr, then diminished quickly. A similar pattern was observed in amniotic fluid and fetal tissues. The reduction in concentration of (14)C from these tissues as a function of time was found to fit a first-order excretion curve. From this model curve, the half-life was calculated to be 2.22 days for diethyl phthalate. Radioactivity from (14)C-diethyl phthalate is transmitted across the placenta from mother to fetus for at least 15 days post-injection. (14)C radioactivity was widely distributed and was detected (
Male rats exposed to a single dermal application of (14)C-diethyl phthalate (5-8 mg/sq cm) excreted 24% of the administered dose in the urine and 1% of the dose in feces within 24 hr. The radioactivity was widely distributed, but diethyl phthalate and its metabolites are not likely to accumulate to any great extent in tissues, because very little of the (14)C radioactivity was found in the tissues 1 week after exposure to diethyl phthalate. The amounts of label found in the brain, lung, liver, spleen, small intestine, kidney, testis, spinal cord, and blood were each less than 0.5% of the administered dose. Adipose tissue, muscle, and skin accounted for 0.03%, 0.14%, and 0.06% of the administered (14)C radioactivity, respectively. Thirty-four per cent remained in the area of application, and 4.8% remained in the plastic cap used to protect the application site. Total recovery of the radiolabel in the urine, feces, tissues, and plastic cap after 7 days was 74 + or - 21%.
(14)C-diethyl phthalate was administered intraperitoneally (2,800 mg/kg) to pregnant rats on either day 5 or day 10 of gestation. Results showed that radioactivity from (14)C-diethyl phthalate is transmitted across the placenta from mother to fetus for at least 15 days postinjection. (14)C Radioactivity was widely distributed and was detected (
DEP is readily absorbed from the skin, intestinal tract, peritoneal cavity, and lung.
The pharmacokinetics of DEP after dermal application have been examined in rats. After 7 day, 34% of the dose remained at the application site. A substantial portion of the dose (25%) was unaccounted for. Urine was the primary source of excretion, with 24% of the dose excreted in the urine during the first day.
The human skin absorption rate of DEP has been reported as 12.75 ug/cm2/hr which is considered to be "slow." Using 12.75 ug/cm2/hr for the absorption rate, 720 cm2 for the skin surface area of both hands, and 60 kg for body weight, contact with the skin of both hands for one hour can be estimated to produce an absorbed dose of approximately 0.15 mg/kg.
... Abdominal skin (dermatomed at 350 microm) from male hairless guinea pigs (n=6) was used to measure diethyl phthalate (DEP) skin permeation parameters. In vitro methods were employed to determine permeability coefficient (k(p)), time lag (tau) and skin-buffer partition coefficient (K(SB)) for 2 mM DEP in HEPES buffered Hanks Balanced Salt Solution. Measurements (mean+/-standard deviations) are: k(p), 0.021+/-0.012 cm/h; tau, 0.67+/-0.18 h; K(SB), 4.74+/-0.68. The skin may be a significant route for the uptake of DEP. [Frasch HF, Barbero AM; Toxicol In Vitro 19 (2): 253-9 (2005)] PubMed Abstract
Cutaneous exposures to occupational chemicals may cause toxic effects. For any chemical, the potential for systemic toxicity from dermal exposure depends on its ability to penetrate the skin. Most laboratory studies measure chemical penetration from an aqueous solution through isolated human or laboratory animal skin, although most exposures are not from pure aqueous solutions. The US EPA Interagency Testing Committee (ITC) mandated by the Toxic Substances Control Act, has required industry to measure the in vitro penetration of 34 chemicals in their pure or neat form (if liquid). The goal of the present study was to measure skin permeability and lag time for three neat chemicals of industrial importance, representing the general types of chemicals to be studied by the ITC (non-volatile liquids, volatile liquids, and solids), and to examine interlaboratory variation from these studies. Steady state fluxes and lag times of diethyl phthalate (DEP, slightly volatile), 1,2-dichloroethane (DCE, highly volatile), and naphthalene (NAP, solid) were studied in two different laboratories using different analytical methods. One lab also measured fluxes and lag times from saturated aqueous vehicle. Static diffusion cells, dermatomed hairless guinea pig skin, and gas chromatography were used to measure skin penetration. In the two laboratories, the steady state fluxes (mean+/-SD; microg cm(-2)hour(-1)) of DEP applied neat were: 11.8+/-4.1 and 23.9+/-7.0; fluxes of DCE (neat) were 6280+/-1380 and 3842+/-712; fluxes of NAP from powder were 30.4+/-2.0 and 7.5+/-4.7. Compared with neat fluxes measured in the same laboratory, flux from saturated aqueous solution was higher with DEP (1.9 x) but lower with DCE (0.17 x) and NAP (0.45 x). The three chemicals studied including a dry powder, demonstrate the potential for significant dermal penetration. [Frasch HF et al; Cutan Ocul Toxicol 26 (2): 147-60 (2007)] PubMed Abstract
Labeled (14C)-DEP was applied topically, and the application sites were covered with cotton patches. Analysis of urine indicated that approximately 9 percent of the radioactivity was excreted after 24 hours, 14 percent after 48 hours, and 16 to 20 percent within 72 hours. After 3 days of topical exposure, tissue distribution was determined by autoradiography. Radioactivity was detected in the lung, heart, liver, kidney, gonads, spleen, and brain. It was not detected in the skin and subdermal fatty tissue at the site of application.
Environmental Fate and Exposure Potential
- Environmental Fate/Exposure Summary:
- The rate constant for the vapor-phase reaction of diethyl phthalate with photochemically-produced hydroxyl radicals has been estimated as 4.5X10-12 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 7.6X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 2.9 years and 106 days at pH values of 7 and 8, respectively(2). Diethyl 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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