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Diphenyl carbonate

Diphenyl carbonate structure

Diphenyl carbonate 

structure
  • CAS No:

    102-09-0

  • Formula:

    C13H10O3

  • Chemical Name:

    Diphenyl carbonate

  • Synonyms:

    Carbonic acid,diphenyl ester;Diphenyl carbonate;Phenyl carbonate ((PhO)2CO);Phenyl carbonate;NSC 37087;98287-56-0

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

Diphenyl carbonate is an acyclic carbonate ester.It is both as a monomer in combination with bisphenol A in the production of polycarbonate polymers and a product of the decomposition of polycarbonates.


Diphenyl carbonate is a carbonate ester that is the diphenyl ester of carbonic acid.

Diphenyl carbonate Basic Attributes

214.21700

214.22

203-005-8

YWV401IDYN

37087

DTXSID3020540

Lustrous needles|WHITE, CRYSTALLINE SOLID

2920909090

Characteristics

35.53000

3.3

white solid

1.1215 g/cm3 @ Temp: 87 °C

80-81 °C

302-306 °C

168 °C

1.576

H2O: Insoluble ;SOL IN ACETONE, CARBON TETRACHLORIDE, OTHER ORG SOLVENTS

1.50e-04 mmHg

CAN BE HALOGENATED & NITRATED IN CHARACTERISTIC MANNER; READILY UNDERGOES HYDROLYSIS & AMMONOLYSIS

Safety Information

NONH for all modes of transport

1

R22; R20

S22; S24/25

FG0500000

Xn

Stable. Incompatible with strong oxidizing agents. Flammable.

P260, P264, P270, P273, P301+P312, P309+P311, P330, P391, P405, P501

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H302 (99.07%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 225 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P301+P312, P309+P311, P330, P405, and P501

Toxicity

Diphenyl carbonate's production and use as a solvent for nitrocellulose(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,900(SRC), determined from a structure estimation method(2), indicates that diphenyl carbonate is expected to have slight mobility in soil(SRC). Volatilization of diphenyl carbonate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.5X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption(SRC). Diphenyl carbonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4X10-4 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,900(SRC), determined from a structure estimation method(2), indicates that diphenyl carbonate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.5X10-5 atm-cu m/mole(4), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), estimated volatilization half-lives for a model river and model lake are 12 hours and 10 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 126 days if adsorption is considered(8). Diphenyl carbonate is expected to undergo hydrolysis due to the presence of hydrolyzable functional groups(3). According to a classification scheme(5), an estimated BCF of 67(SRC), from its log Kow of 3.28(7) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diphenyl carbonate, which has an estimated vapor pressure of 4X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diphenyl carbonate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 96 hours(SRC), calculated from its rate constant of 4X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Diphenyl carbonate may also undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light greater than 290 nm(4).

The rate constant for the vapor-phase reaction of diphenyl carbonate with photochemically-produced hydroxyl radicals has been estimated as 4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 96 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diphenyl carbonate is expected to undergo hydrolysis due to the presence of hydrolyzable functional groups(2). Diphenyl carbonate may also undergo direct photolysis in the environment since this compound contains a functional group that can absorb light greater than 290 nm(2).

An estimated BCF of 67 was calculated for diphenyl carbonate(SRC), using a log Kow of 3.28(3) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for diphenyl carbonate can be estimated to be 3,900(SRC). According to a classification scheme(2), this estimated Koc value suggests that diphenyl carbonate is expected to have slight mobility in soil.

The Henry's Law constant for diphenyl carbonate is estimated as 8.5X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that diphenyl carbonate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 12 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 10 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 126 days if adsorption is considered(4). Diphenyl carbonate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is expected to occur(SRC), however this process is expected to be attenuated by adsorption. Diphenyl carbonate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4X10-4 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to diphenyl carbonate may occur through inhalation and dermal contact with this compound at workplaces where plastics are exposed to thermal stress(SRC). Diphenyl carbonate comprised 81% of the total emissions content resulting from pyrolysis (at 250 °C) of Lexan, which is a polycarbonate used for injection molding(1).

Drug Information

/SRP:/ Basic Treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Esters and related compounds/|/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use propaparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/

Diphenyl carbonate Use and Manufacturing

Methods of Manufacturing

Eckenroth; Ber 27: 3410 (1894); Bischoff; Ber 35: 3434 (1902); Gomberg, Snow; J Am Chem Soc 47: 198 (1925).

Uses

In molten state as solvent for nitrocellulose.

GRADE: TECHNICAL

Carbonic acid, diphenyl ester: ACTIVE

Computed Properties

Molecular Weight:214.22
XLogP3:3.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:214.062994177
Monoisotopic Mass:214.062994177
Topological Polar Surface Area:35.5
Heavy Atom Count:16
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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