84-66-2 Usage
Description
Diethyl phthalate (DEP) is a member of the group of esters of phthalic acid known as phthalates, used ubiquitously as solvents and plasticizers worldwide. DEP can increase the flexibility of plastics and is also contained in deodorant formulations, perfumes, emollients, and insect repellents. It can cross-react with dimethyl phthalate.
Uses
Used in Plastics Industry:
Diethyl phthalate is used as a plasticizer for cellulose ester plastic films and sheets, molded plastics, and manufacturing varnishes. It is also used as a plasticizer for plastics, providing flexibility and compatibility with various resins such as cellulose acetate, cellulose acetate butyrate, polyvinyl acetate, nitrocellulose, ethyl cellulose, polymethyl methacrylate, polystyrene, polyvinyl butyral, and vinyl chloride-vinyl acetate copolymers.
Used in Cosmetics Industry:
Diethyl phthalate is used in cosmetics as a fixative for perfumes and a plasticizer for cellulose resin in various cosmetic products.
Used in Manufacturing Celluloid:
Diethyl phthalate has been used as a substitute for camphor in the manufacture of celluloid, providing flexibility and enhancing the product's properties.
Used as a Solvent:
Diethyl phthalate is used as a solvent for cellulose acetate in the manufacture of varnishes and dopes, as well as an important solvent in various applications.
Used in Analytical Chemistry:
Diethyl phthalate is used as an analytical reagent, a gas chromatography stationary solution, and a solvent for cellulose and esters.
Used as a Lubricant and Foaming Agent:
Diethyl phthalate is used as a lubricant, foaming agent for colored or rare metal mine flotation, and a gas chromatography fixative.
Used in Insect Repellents:
Diethyl phthalate is used as a fixative in insect repellents, providing long-lasting protection against insects.
Used as an Alcohol Denaturant:
Diethyl phthalate is used as an alcohol denaturant, modifying the properties of ethanol for various applications.
Used in Rodenticide Production:
Diethyl phthalate is an intermediate of the rodenticides dimouse, murine, and chlorpyrone, contributing to their effectiveness in controlling rodent populations.
Production Methods
Diethyl phthalate is produced by the reaction of phthalic anhydride with ethanol in the presence of sulfuric acid.
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
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.
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
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 84-66-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 4 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 84-66:
(4*8)+(3*4)+(2*6)+(1*6)=62
62 % 10 = 2
So 84-66-2 is a valid CAS Registry Number.
InChI:InChI:1S/C12H14O4/c1-3-15-11(13)9-7-5-6-8-10(9)12(14)16-4-2/h5-8H,3-4H2,1-2H3
84-66-2Relevant articles and documents
Synthesis and characterization of butylamine-functionalized Cr(III)–MOF–SO3H: Synergistic effect of the hydrophobic moiety on Cr(III)–MOF–SO3H in esterification reactions
Alavijeh, Masoumeh Karimi,Amini, Mostafa M.
, (2019)
Mesoporous solid acid catalysts with partially hydrophobic moieties, [Cr3O(BDC–SO3H)3?x(BDC–SO3NH3Bu)x]n, were prepared from [Cr3O(BDC–SO3H)3]n (MIL-101(Cr)–SO3H) and BuNH2 for the first time and then characterized by the Brunauer–Emmet–Teller (BET) technique, powder X-ray diffraction, field emission electron microscopy, Fourier transform infrared spectroscopy, and thermal and elemental analyses. The nitrogen adsorption–desorption study showed that the specific surface area and total pore volume of MIL-101(Cr)–SO3H decreased after the reaction with butylamine and formation of [Cr3O(BDC–SO3H)3?x(BDC–SO3NH3Bu)x]n. The prepared materials were used as catalysts to investigate the impact of hydrophobic moieties in esterification yields of phthalic anhydride with several alcohols as a probe reaction. The presence of butylamine as a hydrophobic group on MIL-101(Cr)–SO3H increases the esterification yield significantly for hydrophilic alcohols under solvent-free conditions. Moreover, results showed that [Cr3O(BDC–SO3H)3?x(BDC–SO3NH3Bu)x]n can be recovered and reused for several consecutive reactions without significant loss in catalyst activity.
Room temperature depolymerization of lignin using a protic and metal based ionic liquid system: an efficient method of catalytic conversion and value addition
Mehta, Mohit J.,Kulshrestha, Akshay,Sharma, Shweta,Kumar, Arvind
, p. 1240 - 1247 (2021/02/26)
Lignin is one of the most abundant biopolymer which can be utilized to synthesize various chemicalsviaits depolymerization. However, depolymerization of lignin generally occurs under very harsh conditions. Herein, we report the efficient depolymerization of ligninviadissolution in a mixed ionic liquid system: ethyl ammonium nitrate (EAN) + prolinium tetrachloromanganate(ii) [Pro]2[MnCl4] at 35 °C and under atmospheric pressure conditions. The high dissolution of lignin in ethyl ammonium nitrate provided a large number of H-bonding sites leading to the cracking of lignin and subsequent oxidative conversion by [Pro]2[MnCl4]viathe formation of metal-oxo bonding between Mn and lignin molecules. The extracted yield of vanillin was found to be 18-20% on lignin weight basisviaGC-MS analysis. The depolymerization of lignin was confirmed by SEM, FT-IR and PXRD analysis. Since lignin contains UV-absorbing functional groups, the regenerated biomass after the recovery of the depolymerized products was further utilized to synthesize a UV-shielding material. The constructed films from such a material exhibited a high SPF value of 22 and were found to be very effective by limiting the UV degradation of rhodamine B thus making the lignin valorization process economically viable and environmentally sustainable.
Lignin-fueled photoelectrochemical platform for light-driven redox biotransformation
Boonmongkolras, Passarut,Choi, Eun-Gyu,Han, Seunghyun,Kim, Jinhyun,Kim, Kayoung,Kim, Yong Hwan,Lee, Sahng Ha,Lee, Yang Woo,Park, Chan Beum,Shin, Byungha,Trang, Nguyen Vu Thien,Wang, Ding
supporting information, p. 5151 - 5160 (2020/08/25)
The valorization of lignin has significant potential in producing commodity chemicals and fuels from renewable resources. However, the catalytic degradation of lignin is kinetically challenging and often requires noble metal catalysts to be used under harsh and toxic conditions. Here, we report the bias-free, solar reformation of lignin coupled with redox biotransformation in a tandem structure of a BiVO4 photoanode and perovskite photovoltaic. The tandem structure compensates for the potential gap between lignin oxidation and biocatalytic reduction through artificial Z-schematic absorption. We found that the BiVO4-catalyzed photoelectrochemical oxidation of lignin facilitated the fragmentation of higher molecular weight lignin into smaller carboxylated aliphatic and aromatic acids. Lignin oxidation induced photocurrent generation at the photoanode, which enabled efficient electroenzymatic reactions at the cathode. This study successfully demonstrates the oxidative valorization of lignin as well as biocatalytic reductions (e.g., CO2-to-formate and α-ketoglutarate-to-l-glutamate) in an unbiased biocatalytic PEC platform, which provides a new strategic approach for photo-biocatalysis using naturally abundant renewable resources.
