Diethylphthalat Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE, ?LIGE FLüSSIGKEIT.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen oder beim Verbrennen unter Bildung giftiger Rauche und Gase (Phthals?ureanhydrid - s. ICSC 0315). Greift einige Kunststoffarten an.
ARBEITSPLATZGRENZWERTE
TLV: 5 mg/m?(als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt eine gesundheitssch?dliche Kontamination der Luft nicht oder nur sehr langsam ein
LECKAGE
Pers?nliche Schutzausrüstung: Atemschutzger?t mit Partikelfilter entsprechend der Arbeitsplatzkonzentration des Stoffes. Ausgelaufene Flüssigkeit m?glichst in abdichtbaren Beh?ltern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen.
S-S?tze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
Diethyl phthalate (DEP) is a member of the group of esters of phthalic acid known as phthalates, used ubiquitously as solvents and plasticisers worldwide. DEP can increases the flexibility of plastics. It is also contained in deodorant formulations, perfumes, emollients and insect repellents. It can cross react with dimethyl phtalate.
Chemische Eigenschaften
Diethyl 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.
Physikalische Eigenschaften
Clear, colorless, oily liquid with a mild, chemical odor. Bitter taste.
Virtually odorless when pure ("Perfumery
grade" of commercial Diethyl phthalate).
Very bitter taste in weak hydro-alcoholic
solution. Bitter taste perceptible below 20 ppm.
Verwenden
Diethyl phthalate is a Plasticizer for cellulose ester plastic films and sheets; in molded plastics; manufacturing varnishes; cosmetics.
Vorbereitung Methode
Diethyl phthalate is produced by the reaction of phthalic anhydride with ethanol in the presence of sulfuric acid.
Definition
ChEBI: The diethyl ester of benzene-1,2-dicarboxylic acid.
Allgemeine Beschreibung
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.
Air & Water Reaktionen
Insoluble in water.
Reaktivit?t anzeigen
Diethyl 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 Hazard
Diethyl 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).
Brandgefahr
Special Hazards of Combustion Products: Irritating vapors of unburned chemical may form in fire.
Pharmazeutische Anwendungen
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.
Kontakt-Allergie
This 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.
Sicherheitsprofil
Poison 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.
Sicherheit(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
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).
Lager
Diethyl phthalate is stable when stored in a well-closed container in a cool, dry place.
l?uterung methode
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.]
Inkompatibilit?ten
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.
Diethylphthalat Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
