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Diethyl phthalate

CAS No.
84-66-2
Chemical Name:
Diethyl phthalate
Synonyms
Diethyl ester;ETHYL PHTHALATE;Diethy phthalate;PHTHALOL;TETRATHIONATE;Diethyl phthlate;Diethyl-o-phthalate;PHTHALIC ACID, BIS-ETHYL ESTER;Anozol;DIETHYLPHTALATE
CBNumber:
CB3349654
Molecular Formula:
C12H14O4
Molecular Weight:
222.24
MDL Number:
MFCD00009111
MOL File:
84-66-2.mol
MSDS File:
SDS
Last updated:2024-10-28 16:48:35

Diethyl phthalate 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 n20/D 1.502(lit.)
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 Gravity 1.118
Odor water-wh. oily liq., odorless, bitter taste
Viscosity 11.53mm2/s
explosive limit 0.75%, 187°F
Water Solubility 1 g/L (20 ºC)
Merck 14,7371
BRN 1912500
Henry's Law Constant At 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 limits TLV-TWA air 5 mg/m3 (ACGIH). .
Dielectric constant 7.1(45℃)
Stability Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, alkalies.
LogP 2.2 at 41℃
Indirect Additives used in Food Contact Substances DIETHYL PHTHALATE
FDA 21 CFR 175.105; 175.300; 175.320; 178.3910; 181.27
CAS DataBase Reference 84-66-2(CAS DataBase Reference)
EWG's Food Scores 3
FDA UNII UF064M00AF
NIST Chemistry Reference Diethyl phthalate(84-66-2)
EPA Substance Registry System Diethyl phthalate (84-66-2)
Cosmetics Info Diethyl Phthalate

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Warning
Hazard statements  H361
Precautionary statements  P201-P202-P280-P308+P313-P405-P501a
Safety Statements  24/25
RIDADR  UN 3082 9 / PGIII
OEB B
OEL TWA: 5 mg/m3
WGK Germany  2
RTECS  TI1050000
Autoignition Temperature 854 °F
TSCA  Yes
HS Code  29173400
Toxicity LD50 i.p. in rats: 5.06 ml/kg (Singh)
NFPA 704
1
1 0

Diethyl phthalate price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 524972 Diethyl phthalate 99.5% 84-66-2 1l $111 2024-03-01 Buy
Sigma-Aldrich 53008 Diethyl phthalate PESTANAL?, analytical standard 84-66-2 5ml $124 2024-03-01 Buy
Sigma-Aldrich 1193505 Diethyl Phthalate United States Pharmacopeia (USP) Reference Standard 84-66-2 200mg $491 2024-03-01 Buy
TCI Chemical P0296 Diethyl Phthalate >99.0%(GC) 84-66-2 25mL $18 2024-03-01 Buy
TCI Chemical P0296 Diethyl Phthalate >99.0%(GC) 84-66-2 500mL $22 2024-03-01 Buy
Product number Packaging Price Buy
524972 1l $111 Buy
53008 5ml $124 Buy
1193505 200mg $491 Buy
P0296 25mL $18 Buy
P0296 500mL $22 Buy

Diethyl phthalate Chemical Properties,Uses,Production

Description

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.

Chemical Properties

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.

Physical properties

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.

Uses

Diethyl phthalate is a Plasticizer for cellulose ester plastic films and sheets; in molded plastics; manufacturing varnishes; cosmetics.

Uses

Diethyl 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.

Uses

Diethyl phthalate is an intermediate of the rodenticides dimouse, murine, and chlorpyrone, and is also an important solvent. Diethyl phthalate is used as a plasticizer for plastics. Diethyl phthalate is used as an analytical reagent, a gas chromatography stationary solution, a solvent for cellulose and esters, a plasticizer and a lubricant. Diethyl phthalate is used as plasticizer, solvent, lubricant, fixative, foaming agent for colored or rare metal mine flotation, gas chromatography fixative, alcohol denaturant, spray insecticide. This product is mixed with cellulose acetate, cellulose acetate butyrate, polyvinyl acetate, nitrocellulose, ethyl cellulose, polymethyl methacrylate, polystyrene, polyvinyl butyral, vinyl chloride-vinyl acetate Most resins such as copolymers have good compatibility. It is mainly used as a plasticizer for cellulose resin, but the product has high volatility, which limits its wide application.

Production Methods

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.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 2629, 1993 DOI: 10.1016/S0040-4039(00)77642-8

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

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).

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors of unburned chemical may form in fire.

Flammability and Explosibility

Non flammable

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.

Contact allergens

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.

Safety Profile

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.

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.

85-44-9
64-17-5
84-66-2
Synthesis of Diethyl phthalate from Phthalic anhydride and Ethanol
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