基本情報
- 標準SMILES
O=C(Oc1ccccc1)Oc1ccccc1- InChIKey
ROORDVPLFPIABK-UHFFFAOYSA-N- 分子式
- C13H10O3
- 平均分子量
- 214.22 g/mol
- 単同位体質量
- 214.06299418
概要
Diphenyl carbonate is a carbonate ester that is the diphenyl ester of carbonic acid.
名称と識別子
- 優先名称
- Diphenyl carbonate
- IUPAC
- diphenyl carbonate
- 現地名
- 炭酸ジフェニル
- 英語名
- Diphenyl carbonate
- 分子式
- C13H10O3
- 分子量
- 214.22
名称と別名
名称をさらに表示
データベース識別子
- CAS
102-09-0- PubChem CID
- 7597
- DTXSID
DTXSID3020540- ChEMBL
CHEMBL3188080- ChEBI
CHEBI:34722- UNII
- YWV401IDYN
- EC Number
- 203-005-8
- Nikkaji
- J5.004K
物性
構造計算による物性
- XLogP
- 3.3
- 極性表面積
- 35.5 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 4
- 重原子数
- 16
- 形式電荷
- 0
- 複雑度
- 193
実験および物理化学的性質
Color/Form
Lustrous needles
WHITE, CRYSTALLINE SOLID
Solubility
Practically insol in water; sol in hot alc, benzene, ether, glacial acetic acid
SOL IN ACETONE, CARBON TETRACHLORIDE, OTHER ORG SOLVENTS
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
物理化学的性質
- 融点
- 79 · 79-82 °C (lit.)
- 沸点
- 301 · 301-302 °C (lit.)
- 比重(密度)
- 1 · 1,3 g/cm3
- 蒸気圧
- 0.014 Pa · 0.014Pa at 20℃
- 屈折率
- 1.509 · 1.5090 (estimate)
- 闪点
- 168 °C · 168 °C
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- クロロホルム(微量)、メタノール(微量)
- 外見
- フレークまたは結晶性粉末
- 色
- 白い
- 水溶解度
- 不溶性
- Merck
- 14 · 14,7278
- BRN
- 1074863 · 1074863
- Henry's Law Constant
- 1.2 · 1.2×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
- 安定性
- 安定。強力な酸化剤とは相容れない。可燃性。
- InChI
- 1S/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
- SMILES
- O=C(Oc1ccccc1)Oc2ccccc2
- LogP
- 3.21 at · 3.21 at 25℃
- CAS データベース
- 102 · 102-09-0(CAS DataBase Reference)
- NISTの化学物質情報
- Diphenyl carbonate(102-09-0)
- EPAの化学物質情報
- Carbonic acid, diphenyl ester (102-09-0)
化学的性質
化学的特性white solid
化学性质ホスゲン法,エステル交換法,アルコキシスズ法により製造される.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 4.3% (11 of 253) of reports.
Warning
H302 (94.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 253 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]
危険有害性情報
Regulatory Information
Chemical: Carbonic acid, diphenyl ester
Status: Active Update: 04-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15019
Diphenyl carbonate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 4 (94.9%)
Acute toxicity (Oral) - Category 4
Hazardous to the aquatic environment (Acute) - Category 2
安全と保護具
Disposal Methods
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.
毒性情報
Environmental Fate
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).
Soil Adsorption/Mobility
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.
TSCA Test Submissions
Diphenyl carbonate (CAS # 102-09-0) was evaluated for acute oral toxicity in Sprague-Dawley albino rats (5/sex/group) administered doses of 0, 0.75, 1.5, and 3.0 g/kg by oral gavage, based on an initial range-finding study. All mortality occurred from 4 hours to 24 hours post-gavage and was consistent with an oral LD50 of 1.5 g/kg. During 14-day post-gavage observation, clinical signs of toxicity included clonic convulsions (1.5, 3.0 g/kg) and weight loss in 1 and 3 rats, respectively, dying by Day 1 of 3.0 and 1.5 g/kg groups; all surviving rats, including 5/10 mid-dose rats, gained weight. Among the solitary rats of 0.5, 1.0, 1.5, 2.0, and 4.0 gavaged doses in the range-finding study, pharmacotoxic signs observed during 14-day recovery included tremors, tachypnea, clonic convulsions, dyspnea, fasciculation, and hyperactivity. All lethalities in the range-finding study demonstrated distinct lesions upon necropsy with enlarged mandibular lymph nodes, pale renal medullae and spleen, blood accumulations in the brain, and mottled lungs. No gross lesions were identified on terminal necropsy of either survivors or lethalities in the LD50 study.
Environmental Bioconcentration
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.
Volatilization from Water/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).
Environmental Abiotic Degradation
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).
Probable Routes of Human Exposure
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).
Environmental Fate/Exposure Summary
Diphenyl carbonate's production and use as a solvent for nitrocellulose may result in its 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 its 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 it is produced or used. (SRC)
Antidote and Emergency Treatment
/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/
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- FG0500000
- ridadr
- 3077
- 毒性
- rat,LD50,oral,1500mg/kg (1500mg/kg),BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD,National Technical Information Service. Vol. OTS0540144,
- hs_code
- 29209010
- risk_code
- 22-20
- 化審法
- (3)-2490
- hazard_code
- Xn
- safety_code
- 22-24/25
- hazard_class
- 9
- packing_group
- III
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2
- ストレージクラス
- 13 - Non Combustible Solids
- 有毒物質データの
- 102-09-0(Hazardous Substances Data)
化学と産業
用途と製造
Uses
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); [HSDB]
In molten state as solvent for nitrocellulose
PLASTICIZER & SOLVENT; SYNTHESIS OF POLYCARBONATE RESINS
Used in place of carbon monoxide, as reagents for the conversion of amines into isocyanates.
応用分野
用途有機合成原料。
用途医薬?農薬原料
使用Estrogenic activity of Diphenyl Carbonate by yeast 2-hybrid assay was studied.
調製方法
製造方法Diphenyl carbonate is prepared by passing phosgene into a solution of phenol in aqueous sodium hydroxide in the presence of an inert solvent such as methylene chloride: The organic phase, which contains the diphenyl carbonate, is separated; the solvent is stripped off and the diphenyl carbonate is purified by distillation. The reaction is accelerated by tertiary amines and is analogous to the interfacial polycondensation of 2,2-bis(4'hydroxyphenyl)propane and phosgene described. Diphenyl carbonate is a white crystalline solid, m.p. 78C.
合成方法ホスゲン法,エステル交換法,アルコキシスズ法
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A carbonate ester that is the diphenyl ester of carbonic acid.
関連反応
関連ノート
読み込み中…