Chemical Properties
colourless oily liquid
Uses
A phthalate metabolite with genotoxic effect.
Definition
ChEBI: The diethyl ester of benzene-1,2-dicarboxylic acid.
Uses
Ethyl phthalate used in manufacture of celluloid; solvent for cellulose acetate in manufacture of varnishes and dopes; denaturing alcohol. Vehicle for fragrance and cosmetic ingredients.
General Description
A 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.
Reactivity Profile
DIETHYL PHTHALATE(84-66-2) 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].
Air & Water Reactions
Insoluble in water.
Health Hazard
Symptoms unlikely from any form of exposure.
Fire Hazard
Special Hazards of Combustion Products: Irritating vapors of unburned chemical may form in fire.
Description
Diethylphtalate 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.
Physical properties
Clear, colorless, oily liquid with a mild, chemical odor. Bitter taste.
Production Methods
Diethyl phthalate is produced by the reaction of phthalic anhydride with ethanol in the presence of sulfuric acid.
Flammability and Explosibility
Nonflammable
Pharmaceutical Applications
Diethyl 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.
Safety
Diethyl 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
Potential Exposure
Tumorigen,Mutagen; Reproductive Effector; Human Data; PrimaryIrritant. This material is used as a plasticizer, dye carrier,and wetting agent; as a solvent for cellulose esters; as avehicle in pesticidal sprays; as a fixative and solvent in perfumery; as an alcohol denaturant; and as a plasticizer insolid rocket propellants.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Source
Leaching from PVC piping in contact with water (quoted, Verschueren, 1983).
Environmental Fate
Biological. 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).
storage
Diethyl phthalate is stable when stored in a well-closed container in a cool, dry place.
Shipping
The name of this material is not on the DOT listof materials for label and packaging standards. However,based on regulations, it may be classified as anEnvironmentally hazardous substances, liquid, n.o.s. It fallsin Hazard Class 9 and Packing Group III.[20,21]
Purification Methods
Wash 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.]
Incompatibilities
Incompatible with strong oxidizing materials, acids, and permanganates.
Regulatory Status
Included 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.
