PHENYL CARBONATE
Diphenyl carbonate
CAS: 102-09-0
Molecular Formula: C13H10O3
PHENYL CARBONATE - Names and Identifiers
| Name | Diphenyl carbonate |
| Synonyms | DPC AURORA 16157 Phenol carbonate PHENYL CARBONATE Phenyl carbonate DIPHENYL CARBONATE Diphenyl carbonate LABOTEST-BB LT01417418 phenylcarbonate((pho)2co) CARBONIC ACID DIPHENYL ESTER |
| CAS | 102-09-0 |
| EINECS | 203-005-8 |
| InChI | InChI=1/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H |
| InChIKey | ROORDVPLFPIABK-UHFFFAOYSA-N |
PHENYL CARBONATE - Physico-chemical Properties
| Molecular Formula | C13H10O3 |
| Molar Mass | 214.22 |
| Density | 1,3 g/cm3 |
| Melting Point | 79-82 °C (lit.) |
| Boling Point | 301-302 °C (lit.) |
| Flash Point | 168 °C |
| Water Solubility | Insoluble |
| Solubility | Insoluble in water, soluble in hot ethanol, benzene, ether, carbon tetrachloride, glacial acetic acid and other organic solvents. |
| Vapor Presure | 0.014Pa at 20℃ |
| Appearance | White solid |
| Color | White |
| Merck | 14,7278 |
| BRN | 1074863 |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents. Flammable. |
| Refractive Index | 1.5090 (estimate) |
| MDL | MFCD00003037 |
| Physical and Chemical Properties | Character white crystalline solid. melting point 83 ℃ boiling point 302 ℃ relative density 1.1215 (liquid) solubility insoluble in water, soluble in hot ethanol, benzene, ether, carbon tetrachloride, glacial acetic acid and other organic solvents. |
| Use | It is mainly used for the synthesis of engineering plastics such as polycarbonate and poly (p-hydroxybenzoate), and can also be used as a plasticizer and solvent for nitrocellulose |
PHENYL CARBONATE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R20 - Harmful by inhalation |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | 3077 |
| WGK Germany | 1 |
| RTECS | FG0500000 |
| TSCA | Yes |
| HS Code | 29209010 |
| Hazard Class | 9 |
| Packing Group | III |
PHENYL CARBONATE - Upstream Downstream Industry
| Raw Materials | Phenol Sodium hydroxide |
| Downstream Products | Polycarbonate urea-15N2 |
PHENYL CARBONATE - Nature
Open Data Verified Data
white crystalline solid. Melting point 83. The relative density of liquid was 1. 1215. Boiling point 302 °c. Insoluble in water, soluble in hot ethanol, benzene, ether, carbon tetrachloride, acetic acid and other organic solvents. Can be thermal alkali decomposition and ammonolysis. It can be halogenated and nitrated.
Last Update：2024-01-02 23:10:35
PHENYL CARBONATE - Preparation Method
Open Data Verified Data
- phosgene method phosgene and phenol are condensed in NaOH medium to produce diphenyl carbonate. After the completion of the reaction, the product was obtained by removing gas (residual phosgene and hydrogen chloride gas), standing for stratification, washing with water, dehydration, distillation under reduced pressure and crystallization.
- The transesterification synthesis of diphenyl carbonate from phenol and dimethyl carbonate is generally carried out in two steps: the first step is the conversion of phenol to methyl phenyl carbonate, and the second step is its further interaction with phenol to obtain diphenyl carbonate. The yield of this route is low, and it is necessary to develop high efficiency agent and improve the process flow.
- oxidative carbonylation of phenol the next step is the direct synthesis of diphenyl carbonate from phenol, carbon monoxide and oxygen in the presence of a catalyst. This method has the characteristics of simple process, cheap and easy to get raw materials and no pollution. However, it has not achieved industrialization and is in the process of research and development.
Last Update：2022-01-01 10:33:56
PHENYL CARBONATE - Introduction
White crystal. Insoluble in water, soluble in hot ethanol, benzene, ether, carbon tetrachloride, glacial acetic acid and other organic solvents. Can be decomposed and ammoniacated by thermal alkali. It can be halogenated and nitrated.
Last Update：2022-10-16 17:11:32
PHENYL CARBONATE - Use
Open Data Verified Data
important environmental protection chemical products, can be used for the synthesis of many important medicines, pesticides and other organic compounds and polymer materials, such as aliphatic monoisocyanate and p-Hydroxybenzoic acid polyester. Also useful as plasticizers and solvents for polyamides, polyesters.
Last Update：2022-01-01 10:33:56
PHENYL CARBONATE - Safety
Open Data Verified Data
This product has low toxicity. Has an allergic effect on the skin. Attention should be paid to prevent phosgene leakage in the production process, and the production site should be well ventilated. The operator should wear protective gear.
This product is packed with galvanized iron drum, or polypropylene woven bag lined with kraft paper. Store in a ventilated and dry warehouse. According to the provisions of the storage and transportation of toxic chemicals.
Last Update：2022-01-01 10:33:57
PHENYL CARBONATE - Reference Information
| LogP | 3.21 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | diphenyl carbonate (C13H10O3) is white crystalline solid, insoluble in water, soluble in hot ethanol, benzene, ether, carbon tetrachloride, glacial acetic acid and other organic solvents. |
| application | diphenyl carbonate is mainly used to synthesize methyl isocyanate in pesticides to prepare carbamate insecticide carbofuran. In addition, it is mainly used in the plastic industry to manufacture polyaryl carbonate and p-hydroxybenzoic acid polyester, monoisocyanate and diisocyanate. Plastic plasticizers can also be prepared. Used as solvent and heat carrier in chemical production. |
| uses | diphenyl carbonate is mainly used to synthesize methyl isocyanate in pesticides to prepare carbamate insecticide carbofuran. In addition, it is mainly used in the plastic industry to manufacture polyaryl carbonate and p-hydroxybenzoic acid polyester, monoisocyanate and diisocyanate. Plastic plasticizers can also be prepared. Used as solvent and heat carrier in chemical production. |
| production method | diphenyl carbonate has two synthesis methods. (1) phenol and phosgene synthesis method first add 16% ~ 17% sodium hydroxide solution to the reaction pot, then add phenol, and add a small amount of tertiary amine catalyst in the presence of inert solvent; Then add liquid phosgene when it is cooled to about 10 ℃, control the reaction temperature to 20~30 ℃, and the diphenyl carbonate generated by the reaction continuously precipitate into solid small particles. During the reaction, the reaction temperature is controlled by adjusting the adding speed of phosgene and controlling the amount of ice salt. The reaction is completed when the material pH = 6.5~7. First, drive away the remaining phosgene and hydrogen chloride gas, and remove the mother liquor after the material is left standing and layered to obtain crude diphenyl carbonate; then after many times of salt water and cold water washing and separation, then vacuum dehydration and solvent recovery, Finally, after decompression distillation and drum crystallization, the required white flake fine diphenyl carbonate is obtained. my country's patent introduction, lime is used to replace caustic soda and react with phenol to generate phenol calcium salt, and then at room temperature, normal pressure high-speed quantitative phosgenation reaction can be used to produce diphenyl carbonate. Compared with the previous phosgene synthesis method, the unit consumption and cost are significantly reduced, the process conditions are mild, the phosgene temperature is increased from 15~20 ℃ to 20~45 ℃, the frozen brine can be omitted, the phosgene time is reduced from 4~10h to 1~2h, the production efficiency is significantly improved, and various side reactions are effectively inhibited. (2) Ethylene carbonate method This method can obtain diphenyl carbonate by exchanging dimethyl carbonate with phenol in the presence of TiO2/SiO2 catalyst. Dimethyl carbonate and excess phenol were transesterified at 200~250 ℃ and 0.39 MPa nitrogen pressure for 3 hours. The main products were diphenyl carbonate, a small amount of methyl phenyl carbonate and diphenyl ether. 1. The phosgene method is obtained by the reaction of phenol and phosgene. The dissolved phenol is added to 16-20% sodium hydroxide solution to prepare sodium phenol solution. Stir and cool, start to introduce phosgene at about 10 ℃, control the phosgene reaction to proceed at 20-30 ℃, the reaction tail gas contains hydrogen chloride and unreacted phosgene, which is introduced into the absorption tower, and is destroyed by dilute alkali solution and discharged from high altitude. At the later stage of the reaction, the reaction solution was taken to test the pH, and the light gas was stopped until neutral. Remove phosgene and hydrochloric acid gas from the pan, filter, wash with water, and melt and dehydrate under reduced pressure to obtain crude products. The crude product is distilled under reduced pressure, the narrow fraction is collected, and the liquid product is condensed by the tablet to obtain refined diphenyl carbonate. Polymerized grade products have high purity requirements, and the melting point should be ≥ 78 ℃. Raw material consumption quota: phenol 963kg/t, sodium hydroxide (30%)577kg/t, phosgene (≥ 98%)592kg/t. 2. The transesterification method synthesizes diphenyl carbonate by exchanging phenol and dimethyl carbonate, which is usually carried out in two steps: the first step is to convert phenol into methyl phenyl carbonate, and the second step is to further interact with phenol to obtain diphenyl carbonate. The yield of this route is low, and it is necessary to develop efficient catalysts and improve the process flow. 3. Phenol oxidative carbonylation method uses phenol, carbon monoxide and oxygen to directly synthesize diphenyl carbonate in the next step in the presence of catalyst. This method has the characteristics of simple process, cheap and easy to obtain raw materials and no pollution. However, industrialization has not been realized and is in the process of research and development. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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Raw Materials for PHENYL CARBONATE
Downstream Products for PHENYL CARBONATE