DIPHENYL CARBONATE

DPC

CAS Number: 102-09-0
EC Number: 203-005-8
Molecular Weight: 214.22
Molecular Formula: C13H10O3

Diphenyl carbonate is the organic compound with the formula (C6H5O)2CO. 
Diphenyl carbonate is classified as an acyclic carbonate ester. 

Diphenyl carbonate is a colorless solid. 
Diphenyl carbonate is both a monomer in combination with bisphenol A in the production of polycarbonate polymers and a product of the decomposition of polycarbonates.

DPC is an essential and nontoxic precursor for the polycarbonate (PC) production. 
With the development of carbonate industry, the need for DPC will be increasing. 

Kim and Lee (1999) suggested a transesterification way of dimethyl carbonate (DMC) and phenol to manufacture DPC. 
However, the equilibrium constant for transesterifications of DMC and phenol was only 3 × 10− 4 at 180 °C in the research of Tundo and Selva (2002). 

To overcome this problem, diethyl carbonate (DEC) and phenyl ester (PA) transesterification to produce the product DPC and the byproduct ethyl acetate (EtAc) was proposed. 
The advantages of this process include higher equilibrium constant and no azeotropes.

DPC is produced from phenol and carbonyl dichloride using a new nitrogen containing catalyst without the use of organic solvent. 
Transesterification of DPC and bisphenol-A to produce PC is performed in the presence of an alkali metal compound catalyst controlling the amount of branching structures and the polymer molecular weight based on the kinetics. 
The first commercial plant based on this process started in 2000.

Diphenyl carbonate (DPC) is a carbonate ester of formula (C6H5O)2CO, which is mostly used as a critical comonomer in the manufacture of polycarbonate resin, an engineering thermoplastic with high impact resistance and excellent optical properties. 
Originally, polycarbonate was produced by interfacial (organic/aqueous) polycondensation of phosgene (COCl2) with disodium salt of a bisphenol, such as 2,2-bis(4-hydroxyphenyl)propane (bisphenol A). 
However, a phosgene-free route was desired because of environmental hazards and governmental restrictions associated with production and storage of extremely toxic phosgene (and chlorine used to synthesize Diphenyl carbonate) and the use of chlorinated solvents.

DPC is commonly produced by indirect methods, mainly by transesterification of dialkylcarbonates such as dimethyl carbonate produced either from CO, methanol, and oxygen using EniChem technology (SABIC IP) or via carbonylation of methyl nitrite from the reaction of NO with methanol or by methanolysis of ethylene carbonate or di-n-butyl carbonate from urea and n-butyl alcohol. 
Ideally, DPC can be prepared directly from phenol, carbon monoxide, and oxygen in a simpler (one-step) energetically favorable reaction. 
Development of the one-step DPC synthesis process conducted by GE team and other researchers, which resulted in tremendous increase in catalytic activity from tens to greater than 10 000 Pd turnover numbers and eventually in a viable technology process, is described.

This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 000 to < 1 000 000 tonnes per annum.
This substance is used at industrial sites and in manufacturing.

Diphenyl carbonate - is an acyclic carbonate ester. 
Diphenyl carbonate 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 phenol that is used as a precursor to other chemicals. 
Diphenyl carbonate is produced through the oxidation of benzene with phosphorus oxychloride, and is also obtained by the chlorination of phenol. 

In electrochemical impedance spectroscopy, Diphenyl carbonate has been shown to be an effective model system for multi-walled carbon nanotubes. 
The optimum concentration of diphenyl carbonate in the reaction solution was determined using analytical methods and reactive properties were observed in a solid catalyst system. 

The mechanism for this reaction is unknown. 
Diphenyl carbonate has been shown to react with dibutyltin oxide in the presence of hydroxyl groups to form diphenyl compounds, which are catalysts for various organic reactions.

Diphenyl carbonate (DPC) was synthesized from phenol and dense phase CO2 in the presence of CCl4 and K2CO3 using different catalysts of ZnCl2, ZnBr2, Lewis acid ionic liquids including 1-butyl-3-methylimidazolium chloride (BMIMCl) and bromide (BMIMBr). 
Diphenyl carbonate was found that K2CO3 was not required, ZnCl2 and ZnBr2 were similar in the catalytic performance, and the use of BMIMCl and BMIMBr was not effective for the production of DPC. 

For the reactions with ZnCl2 in CCl4, the effects of such reaction variables as temperature, CO2 pressure, the amount of ZnCl2, and the volume of CCl4 were studied in detail. 
Diphenyl carbonate was shown that the pressure was less influential while a larger amount of ZnCl2, a smaller volume of CCl4, and a low temperature of around 100°C were beneficial for the synthesis of DPC. 
On the basis of the results obtained, possible reaction mechanisms were discussed.

Production of Diphenyl carbonate:
World production capacity of diphenyl carbonate was 254,000 tonnes in 2002, and phosgenation of phenol is the most significant route.
Phosgenation of phenol can proceed under various conditions. 

The net reaction is as follows:
2 PhOH + COCl2 → PhOCO2Ph + 2 HCl

The use of phosgene can be avoided by the oxidative carbonylation of phenol with carbon monoxide:
2 PhOH + CO + [O] → PhOCO2Ph + H2O

Dimethyl carbonate can also be transesterified with phenol:
CH3OCO2CH3 + 2 PhOH → PhOCO2Ph + 2 MeOH

The kinetics and thermodynamics of this reaction are not favorable. 
For example, at higher temperatures, dimethyl carbonate undesirably methylates phenol to give anisole.
Despite this, diphenyl carbonate made from non-phosgene sources has become a widely used raw material for the synthesis of bisphenol-A-polycarbonate in a melt polycondensation process.

Benefits of Diphenyl carbonate:
High DPC product purity, suitable for high quality polycarbonate production
No use of chlorinated compounds, environmentally safe, no corrosion

High phenol conversion per pass, low recycle flows
Commercially available catalyst

Can be designed for high capacities
Extensive heat integration, low energy consumption
Low investment cost

Uses of Diphenyl carbonate:
Diphenyl carbonate is used in the synthesis of polycarbonate resins
As a reagent for the conversion of amines into isocyanates
As a plasticizer and solvent; as a solvent for nitrocellulose (in molten state).

In molten state as solvent for nitrocellulose

Plasticizer & solvent
Synthesis of polycarbonate resins

Diphenyl carbonate is used in place of carbon monoxide, as reagents for the conversion of amines into isocyanates.

Uses at industrial sites of Diphenyl carbonate:
Diphenyl carbonate is used in the following products: polymers.
Diphenyl carbonate has an industrial use resulting in manufacture of another substance (use of intermediates).

Diphenyl carbonate is used for the manufacture of: chemicals and plastic products.
Release to the environment of Diphenyl carbonate can occur from industrial use: for thermoplastic manufacture.

Applications of Diphenyl carbonate:
Polycarbonates can be prepared by transesterifying diphenyl carbonate with bisphenol A. 
Phenol is a co-product. 
These polycarbonates may be recycled by reversing the process: transesterifying the polycarbonate with phenol to yield diphenyl carbonate and bisphenol A.

D 2320 (OTTO) Diphenyl carbonate, 99% Cas 102-09-0 - used for the production of polycarbonates using. 
D 2320 (OTTO) Diphenyl carbonate, 99% Cas 102-09-0 - used for synthesis of many important organic compounds. 
As agrochemical intermediates, Dyestuff intermediate.

Manufacture of Diphenyl carbonate:
Release to the environment of Diphenyl carbonate can occur from industrial use: manufacturing of the substance.

Handling And Storage of Diphenyl carbonate:

Handling of Diphenyl carbonate:

Technical measures:
Avoid contact with strong oxidizing agents. 
Use with local exhaust ventilation. 

Precautions:
Do not rough handling containers, such as upsetting, falling, giving a shock, and dragging. 
Prevent leakage, overflow, andscattering. 

Not to generate steam and dust in vain. 
Seal the container after use. 

After handling, wash hands andface, andthen gargle. 
In places other than those specified, should not be smoking or eating and drinking. 

Should not bebrought:
contaminated protective equipment and gloves to rest stops. 
Deny unnecessary entry of non-emergency personnel tothehandling area. 

Safety handling precautions:
Avoid contact with skin, eyes or clothing. 
Use personal protective equipment as required. 

Storage of Diphenyl carbonate:

Safe storage conditions of Diphenyl carbonate:
Store away from sunlight in well-ventilated place at room temperature (preferablycool).
Keep container tightly closed. 

Safe packaging material Incompatible substances:
Glass 
Strong oxidizing agents

Ecological Information of Diphenyl carbonate:

Environmental Fate/Exposure Summary:
Diphenyl carbonate's production and use as a solvent for nitrocellulose may result in Diphenyl carbonate release to the environment through various waste streams. 
If released to air, an estimated vapor pressure of 4X10-4 mm Hg at 25 °C indicates diphenyl carbonate will exist solely as a vapor. 

Vapor-phase diphenyl carbonate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 96 hours. 
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. 

If released to soil, diphenyl carbonate is expected to be slightly mobile based upon an estimated Koc of 3,900. 
Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 8.5X10-5 atm-cu m/mole; however, this process is expected to be attenuated by adsorption. 

If released into water, diphenyl carbonate is expected to adsorb to suspended solids and sediment based upon Diphenyl carbonate Koc. 
Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. 

Estimated volatilization half-lives for a model river and model lake are 10 days and 12 hours, respectively. 
However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. 

The estimated volatilization half-life from a model pond is 126 days if adsorption is considered. 
Diphenyl carbonate is expected to undergo hydrolysis due to the presence of hydrolyzable functional groups. 

An estimated BCF of 67 suggests the potential for bioconcentration in aquatic organisms is moderate. 
Occupational exposure to diphenyl carbonate may occur through inhalation and dermal contact with this compound at workplaces where Diphenyl carbonate is produced or used.

Safety Information of Diphenyl carbonate:
Signal Word: Warning
Hazard Statements: H302 - H410
Precautionary Statements: P264 - P270 - P273 - P301 + P312 - P391 - P501
Hazard Classifications: Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 2
Storage Class Code: 13 - Non Combustible Solids
WGK: WGK 1
Flash Point(F): 334.4 °F - closed cup
Flash Point(C): 168 °C - closed cup
Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Accidental Release Measures of Diphenyl carbonate:
Personal precautions, protective equipment and emergency procedures:
For indoor, provide adequate ventilation process until the end of working. 

Deny unnecessary entry other thanthepeopleinvolved by, for example, using a rope. 
While working, wear appropriate protective equipments to avoid adheringit onskin, or inhaling the gas. 

Work from windward, and retract the people downwind. 
Environmental precautions:
To be careful not discharged to the environment without being properly handled waste water contaminated.

Methods and materials for contaminent and methods and materials for cleaning up:
Sweep up and gather scattered particles, and collect Diphenyl carbonate in an empty airtight container. 

Recoverly, neutralization:
No information available

Secondary disaster prevention measures:
Clean contaminated objects and areas thoroughly observing environmental regulations.

Disposal Methods of Diphenyl carbonate:
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.

Antidote and Emergency Treatment of Diphenyl carbonate:
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.

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.

First Aid Measures of Diphenyl carbonate:

Inhalation:
Remove to fresh air. 
If symptoms persist, call a physician. 

Skin contact:
Wash off immediately with soap and plenty of water. 
If symptoms persist, call a physician. 

Eye contact:

If in eyes: Rinse cautiously with water for several minutes. 
Remove contact lenses, if present and easy to do. 
Continuerinsing. 
Immediate medical attention is required.

Ingestion:
Rinse mouth. 
Never give anything by mouth to an unconscious person. 
Call a physician or poison control center immediately. 
Do not induce vomiting without medical advice. 

Protection of first-aiders:
Use personal protective equipment as required.

Fire Fighting Measures of Diphenyl carbonate:

Suitable extinguishing media:
Water spray (fog), Carbon dioxide (CO2), Foam, Extinguishing powder, Sand

Unsuitable extinguishing media:
No information available

Specific hazards arising from the chemical product:
Thermal decomposition can lead to release of irritating and toxic gases and vapors. 

Special extinguishing method:
No information available

Special protective actions for fire-fighters:
Use personal protective equipment as required. 
Firefighters should wear self-contained breathing apparatus andfull firefighting turnout gear.

Identifiers of Diphenyl carbonate:
CAS Number: 102-09-0
ChEBI: CHEBI:34722
ChemSpider: 7315
ECHA InfoCard: 100.002.733
KEGG: C14507
PubChem CID: 7597
UNII: YWV401IDYN
CompTox Dashboard (EPA): DTXSID3020540
InChI:
InChI=1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
Key: ROORDVPLFPIABK-UHFFFAOYSA-N check
InChI=1/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
Key: ROORDVPLFPIABK-UHFFFAOYAY
SMILES: O=C(Oc1ccccc1)Oc2ccccc2

Properties of Diphenyl carbonate:
Chemical formula: C13H10O3
Molar mass: 214.216 g/mol
Density: 1.1215 g/cm3 at 87 °C
Melting point: 83 °C (181 °F; 356 K)
Boiling point: 306 °C (583 °F; 579 K)
Solubility in water: insoluble
Solubility: soluble in ethanol, diethyl ether, carbon tetrachloride, acetic acid

Quality Level: 200
Assay: 99%
Form: crystals
bp: 301-302 °C (lit.)
mp: 79-82 °C (lit.)
SMILES string: O=C(Oc1ccccc1)Oc2ccccc2
InChI: 1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
InChI key: ROORDVPLFPIABK-UHFFFAOYSA-N

Molecular Weight: 214.22
XLogP3: 3.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 4
Exact Mass: 214.062994177
Monoisotopic Mass: 214.062994177
Topological Polar Surface Area: 35.5 Ų
Heavy Atom Count: 16
Complexity: 193
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Diphenyl carbonate:
Color: White
Melting Point: 78.0°C to 81.0°C
Boiling Point: 301.0°C to 302.0°C
Flash Point: 168°C
Assay Percent Range: 98.5% min. (GC)
Infrared Spectrum: Authentic
Linear Formula: (C6H5O)2CO
Beilstein: 06,158
Packaging: Plastic bottle
Merck Index: 15,3354
Quantity: 1kg
Solubility Information: Solubility in water: insoluble. Other solubilities: solulbe in acetone, hot alcohol, benzene, carbon, tetrachloride, ether, glacial acetic acid and, other organic solvents
Formula Weight: 214.22
Physical Form: Flakes or Crystalline Powder
Percent Purity: 99%
Chemical Name or Material: Diphenyl carbonate

Related Products of Diphenyl carbonate:
1-(3,5-dichloropyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
1,3-dimethyl-1H,4H,5H,6H-pyrazolo[3,4-b][1,4]thiazin-5-one
2-(3,5-dichlorophenyl)-2-(ethylamino)acetic acid hydrochloride
6,7-dichloro-2-methyl-2,3-dihydro-1-benzofuran-3-one
2-{[(3,4-dichlorophenyl)carbamoyl]amino}-3-(1H-indol-3-yl)propanoic acid

Names of Diphenyl carbonate:

Regulatory process names of Diphenyl carbonate:
Carbonic acid, diphenyl ester
Diphenyl carbonate
Diphenyl carbonate
diphenyl carbonate
Phenyl carbonate
Phenyl carbonate ((PhO)2CO)

CAS names of Diphenyl carbonate:
Carbonic acid, diphenyl ester

IUPAC names of Diphenyl carbonate:
Diphenyl Carbonate
Diphenyl carbonate
diphenyl carbonate
Diphenyl carbonate
Diphenylcarbonat
DPC

Preferred IUPAC name of Diphenyl carbonate:
Diphenyl carbonate

Trade names of Diphenyl carbonate:
Carbonic acid diphenyl ester
Diphenyl carbonate
DPC
EF-1032
EN-1052
HF-3200H
HI-1001BS
HM-1150S
HN-3104
HN-3104R
LB-3150G
NE-1010
NE-1030
NF-3017
NH-1000T
NH-1015
NH-1015V
NH-1017D
NH-1017SG
PC00-SC-1060U00
PC00-SC-1080F00
PC00-SC-1100R00
PC00-SC-1100UR0
PC00-SC-1220R00
PC00-SC-1220UR0
PC00-SC-1280UR0
SA-1220
TN-1045M
VB-1202F
WP-1041G
WP-1069
WR-7350

Other names of Diphenyl carbonate:
Phenyl carbonate, di-

Synonyms of Diphenyl carbonate:
DIPHENYL CARBONATE
102-09-0
Carbonic acid, diphenyl ester
Diphenylcarbonate
Phenyl carbonate
Phenyl carbonate ((PhO)2CO)
UNII-YWV401IDYN
Carbonic Acid Diphenyl Ester
Ph2CO3
(PhO)2CO
YWV401IDYN
CHEBI:34722
NSC 37087; Phenyl carbonate
MFCD00003037
HSDB 5346
EINECS 203-005-8
NSC 37087
BRN 1074863
phenoxy ketone
AI3-00063
Phenol carbonate
diphenyl-carbonate
Carbonic acid diphenyl
WLN: ROVOR
DSSTox_CID_540
EC 203-005-8
Cambridge id 6944698
DSSTox_RID_75649
DSSTox_GSID_20540
SCHEMBL18073
BIDD:ER0260
CHEMBL3188080
DTXSID3020540
ZINC134817
NSC37087
Tox21_200150
NSC-37087
STL185617
AKOS002275760
MCULE-5577922375
NCGC00248543-01
NCGC00257704-01
BS-14177
CAS-102-09-0
Diphenyl carbonate, ReagentPlus(R), 99%
FT-0625229
EN300-36556
A800511
Diphenyl carbonate 100 microg/mL in Acetonitrile
Diphenyl carbonate, Vetec(TM) reagent grade, 98%
Q413098
SR-01000246916
Q-201005
SR-01000246916-1
Z28228668
F3096-1220
102-09-0 [RN]
203-005-8 [EINECS]
Carbonate de diphényle 
Carbonic acid diphenyl ester
Carbonic acid, diphenyl ester
Diphenyl carbonate
Diphenylcarbonat 
Diphenylcarbonate
MFCD00003037
Phenyl carbonate
UNII-YWV401IDYN
YWV401IDYN
203-005-8MFCD00003037
2-HYDROXYIMINO-2-(2-PYRIDYLSULFONYL)ACETONITRILE
4-06-00-00629
Phenol carbonate
phenyl phenoxyformate
ROVOR
UNII:YWV401IDYN