DIPHENYL CARBONATE

Diphenyl carbonate 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.

Diphenyl carbonate is produced from phenol and carbonyl dichloride using a new nitrogen containing catalyst without the use of organic solvent.

Diphenyl carbonate 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.

CAS Number: 102-09-0

EC Number: 203-005-8

Molecular Weight: 214.22

Molecular Formula: C13H10O3

Synonyms: 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

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.

Diphenyl carbonate is an essential and nontoxic precursor for the polycarbonate (PC) production. 

With the development of carbonate industry, the need for Diphenyl carbonate will be increasing. 

Kim and Lee (1999) suggested a transesterification way of dimethyl carbonate (DMC) and phenol to manufacture Diphenyl carbonate. 

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 Diphenyl carbonate and the byproduct ethyl acetate (EtAc) was proposed. 

The advantages of this process include higher equilibrium constant and no azeotropes.

Diphenyl carbonate is produced from phenol and carbonyl dichloride using a new nitrogen containing catalyst without the use of organic solvent. 

Transesterification of Diphenyl carbonate 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 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.

Diphenyl carbonate 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, Diphenyl carbonate can be prepared directly from phenol, carbon monoxide, and oxygen in a simpler (one-step) energetically favorable reaction. 

Development of the one-step Diphenyl carbonate 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.

Diphenyl carbonate 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. Diphenyl carbonate 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 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 Diphenyl carbonate.  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 Diphenyl carbonate.  On the basis of the results obtained, possible reaction mechanisms were discussed. 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. Benefits of Diphenyl carbonate: High Diphenyl carbonate 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 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. Manufacture of Diphenyl carbonate: Release to the environment of Diphenyl carbonate can occur from industrial use: manufacturing of Diphenyl carbonate. 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: Carbonic acid, diphenyl ester Diphenyl carbonate Diphenyl carbonate diphenyl carbonate Phenyl carbonate Phenyl carbonate ((PhO)2CO) CAS names: Carbonic acid, diphenyl ester IUPAC names: Diphenyl Carbonate Diphenyl carbonate diphenyl carbonate Diphenyl carbonate Diphenylcarbonat DPC Preferred IUPAC name: Diphenyl carbonate Trade names: 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 name: Phenyl carbonate, di-