ChemicalBook > Product Catalog > Flavors and fragrances > Synthetic fragrances > Carboxylic acids and esters > Aromatic carboxylic acid ester > Diethyl phthalate
Diethyl phthalate Chemical Properties
- Melting point:−3 °C(lit.)
- Boiling point:298-299 °C(lit.)
- Density 1.12 g/mL at 25 °C(lit.)
- vapor density 7.66 (vs air)
- vapor pressure 1 mm Hg ( 100 °C)
- refractive index n
- Flash point:>230 °F
- storage temp. 2-8°C
- solubility Practically insoluble in water, miscible with ethanol (96 per cent).
- form Liquid
- color APHA: ≤15
- Specific Gravity1.118
- explosive limit0.75%, 187°F
- Water Solubility 1 g/L (20 ºC)
- Merck 14,7371
- BRN 1912500
- Henry's Law ConstantAt 25 °C: 5.01, 4.54, 4.78, 4.94, 2.21, and 2.44 (x 10-5 atm?m3/mol)at pH values of 2.96, 2.98, 6.18, 6.19, 8.98, and 9.00, respectively (Hakuta et al., 1977).
- Exposure limitsTLV-TWA air 5 mg/m3 (ACGIH). .
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, alkalies.
- CAS DataBase Reference84-66-2(CAS DataBase Reference)
- NIST Chemistry ReferenceDiethyl phthalate(84-66-2)
- EPA Substance Registry SystemDiethyl phthalate (84-66-2)
Diethyl phthalate Usage And Synthesis
- DescriptionDiethylphtalate is a plasticizer which increases the flexibility of plastics. It is also contained in deodorant formulations, perfumes, emollients and insect repellents. It can cross react with dimethyl phtalate.
- Chemical PropertiesDiethyl phthalate is a clear, colorless, oily liquid. It is practically odorless, or with a very slight aromatic odor and a bitter, disagreeable taste. It is miscible with ethanol and ethyl ether. Diethyl phthalate is soluble in acetone, benzene, carbon tetrachloride, alcohols, ketones, esters, and aromatic hydrocarbons and partly miscible with aliphatic solvents. Diethyl phthalate, when exposed to heat, decomposes and emits acrid smoke and irritating fumes. It is incompatible with strong oxidisers, strong acids, nitric acid, permanganates, and water and attacks some forms of plastics. Diethyl phthalate is produced in the reaction of phthalic anhydride with ethanol in the presence of concentrated sulphuric acid catalyst.
- Physical propertiesClear, colorless, oily liquid with a mild, chemical odor. Bitter taste.
- UsesDiethyl phthalate has been used as a substitute for camphor in the manufacture of celluloid, as a solvent for cellulose acetate in the manufacture of varnishes and dopes, as a ftxative for perfumes, and for denaturing ethanol.
Diethyl phthalate is a Plasticizer for cellulose ester plastic films and sheets; in molded plastics; manufacturing varnishes; cosmetics.
- UsesEthyl phthalate used in manufacture of celluloid; solvent for cellulose acetate in manufacture of varnishes and dopes; denaturing alcohol. Vehicle for fragrance and cosmetic ingredients.
- DefinitionChEBI: The diethyl ester of benzene-1,2-dicarboxylic acid.
- Production MethodsDiethyl phthalate is produced by the reaction of phthalic anhydride with ethanol in the presence of sulfuric acid.
- Synthesis Reference(s)Tetrahedron Letters, 34, p. 2629, 1993 DOI: 10.1016/S0040-4039(00)77642-8
- General DescriptionA clear, colorless liquid without significant odor. More dense than water and insoluble in water. Hence sinks in water. Primary hazard is to the environment. Spread to the environment should be immediately stopped. Easily penetrates soil, contaminates groundwater and nearby waterways. Flash point 325°F. Severely irritates eyes and mildly irritates skin. Used in the manufacture of perfumes, plastics, mosquito repellents and many other products.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileDiethyl 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. Can generate electrostatic charges. [Handling Chemicals Safely 1980. p. 250].
- Health HazardDiethyl phthalate exhibited low to very lowacute toxicity in laboratory animals. Inges tion produced somnolence and hypotension.Inhalation of its vapors may result in lacrima tion, coughing, and irritation of the throatin humans. The oral LD50 value in mice is6170 mg/kg. Diethyl phthalate administeredto pregnant rats at 5% concentration in thefeed showed no adverse effect upon embryoor fetal growth, viability, or the incidence ofmalformations (Price et al. 1988).
- Fire HazardSpecial Hazards of Combustion Products: Irritating vapors of unburned chemical may form in fire.
- Pharmaceutical ApplicationsDiethyl phthalate is used as a plasticizer for film coatings on tablets, beads, and granules at concentrations of 10–30% by weight of polymer.
Diethyl phthalate is also used as an alcohol denaturant and as a solvent for cellulose acetate in the manufacture of varnishes and dopes. In perfumery, diethyl phthalate is used as a perfume fixative at a concentration of 0.1–0.5% of the weight of the perfume used.
- Contact allergensThis plasticizer increases the fexibility of plastics. It is also contained in deodorant formulations, perfumes, emollients, and insect repellents. It can cross-react with dimethyl phthalate.
- Safety ProfilePoison by intravenous route. Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. Human systemic effects by inhalation: lachrymation, respiratory obstruction, and other unspecified respiratory system effects. An eye irritant and systemic irritant by inhalation. An experimental teratogen. Other experimental reproductive effects. Narcotic in hgh concentrations. Combustible when exposed to heat or flame. To fight fire, use water spray, mist, foam. When heated to decomposition it emits acrid smoke and irritating fumes.
- SafetyDiethyl phthalate is used in oral pharmaceutical formulations and is generally regarded as a nontoxic and nonirritant material at the levels employed as an excipient. However, if consumed in large quantities it can act as a narcotic and cause paralysis of the central nervous system.
Although some animal studies have suggested that high concentrations of diethyl phthalate may be teratogenic, other studies have shown no adverse effects.
LD50 (guinea pig, oral): 8.6g/kg
LD50 (mouse, IP): 2.7g/kg
LD50 (mouse, oral): 6.2g/kg
LD50 (rat, IP): 5.1g/kg
LD50 (rat, oral): 8.6g/kg
- SourceLeaching from PVC piping in contact with water (quoted, Verschueren, 1983).
- Environmental FateBiological. A proposed microbial degradation mechanism is as follows: 4-hydroxy-3-
methylbenzyl alcohol to 4-hydroxy-3-methylbenzaldehyde to 3-methyl-4-hydroxybenzoic acid to
4-hydroxyisophthalic acid to protocatechuic acid to β-ketoadipic acid (Chapman, 1972). In
anaerobic sludge, diethyl phthalate degraded as follows: monoethyl phthalate to phthalic acid to
protocatechuic acid followed by ring cleavage and mineralization (Shelton et al., 1984).
Photolytic. An aqueous solution containing titanium dioxide and subjected to UV radiation (λ >290 nm) produced hydroxyphthalates and dihydroxyphthalates as intermediates (Hustert and Moza, 1988).
Chemical/Physical. Under alkaline conditions, diethyl phthalate will initially hydrolyze to ethyl hydrogen phthalate and ethanol. The monoester will undergo hydrolysis forming o-phthalic acid and ethanol (Kollig, 1993). A second-order rate constant of 2.5 x 10-2/M?sec was reported for the hydrolysis of diethyl phthalate at 30 °C and pH 8 (Wolfe et al., 1980). At 30 °C, hydrolysis halflives of 8.8 and 18 yr were reported at pH values 9 and 10-12, respectively (Callahan et al., 1979).
- storageDiethyl phthalate is stable when stored in a well-closed container in a cool, dry place.
- Purification MethodsWash the ester with aqueous Na2CO3, then distilled water, dry (CaCl2), and distil it under reduced pressure. Store it in a vacuum desiccator over P2O5. [Beilstein 9 IV 3172.]
- IncompatibilitiesIncompatible with strong oxidizing materials, acids, and permanganates.
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (oral capsules, delayed action, enteric coated, and sustained action tablets). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Diethyl phthalate Preparation Products And Raw materials
- Dimethyl phthalate Benzyl butyl phthalate Phthalic acid Bis(2-methoxyethyl) phthalate Diallyl phthalate Dicyclohexyl phthalate DI-N-HEXYL PHTHALATE DIPHENYL PHTHALATE DI-N-PENTYL PHTHALATE-D4 Dinonyl phthalate BIS(2-ETHOXYETHYL)PHTHALATE BIS(2-N-BUTOXYETHYL)PHTHALATE BIS(4-METHYL-2-PENTYL)PHTHALATE Diethyl malonate DIETHYL PHOSPHATE Diisooctyl phthalate Diethyl carbonate Mefenpyr-diethyl
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