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炭酸ジフェニル

Diphenyl carbonate

HCID 7597
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
102-09-0
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

DIPHENYL CARBONATE102-09-0Carbonic acid, diphenyl esterPhenyl carbonateCarbonic Acid Diphenyl EsterPhenyl carbonate ((PhO)2CO)Ph2CO3HSDB 5346(PhO)2COYWV401IDYNEINECS 203-005-8NSC 37087
名称をさらに表示
炭酸ジフェニルジフェニルカボネトジフェニルカーボネ-トジフェニルカルボナート炭酸フェニル炭酸ジフェニル, 99%ジフェニルカーボネートジフェニル=カルボナートフェノキシぎ酸フェニルジフェノキシケトンフェニルカルボナートジフェニル カルボナートビス(2-ピリジル)ケトン4-メチル-4-シクロヘキシルチオセミカルバゾン1-[ビス(2-ピリジニル)メチレン]-4-メチル-4-シクロヘキシルチオセミカルバジド1-{[ビス(ピリジン-2-イル)メチリデン]アミノ}-3-シクロヘキシル-3-メチルチオ尿素ビス(2-ピリジニル)ケトン4-メチル-4-シクロヘキシルチオセミカルバゾンDPCDiphenyl carbonate, 99.50%AURORA 16157DiphenylcarbonatPhenol carbonateDiphenyl carboteiphenylcarbonateDIFENILCARBONATO
BRN 1074863AI3-00063NSC-37087DIPHENYL CARBONATE [MI]CHEBI:34722DIPHENYL CARBONATE [HSDB]EC 203-005-8PHENYL CARBONATE [(PHO)2CO]

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補完中

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

Chemical ClassesOther Classes -> Other Aromatic Compounds
SpringerMaterials PropertiesCrystal structure
LogPlog Kow= 3.28
Density1.1215 @ 87 °C/4 °C
Color/Form · 2 件

Lustrous needles

WHITE, CRYSTALLINE SOLID

Solubility · 2 件

Practically insol in water; sol in hot alc, benzene, ether, glacial acetic acid

SOL IN ACETONE, CARBON TETRACHLORIDE, OTHER ORG SOLVENTS

Boiling Point302-306 °C
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Melting Point80-81 °C
Vapor Pressure0.0001 [mmHg]
Food Contact Substances · 2 件

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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 · 3 件

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

Hazards SummaryA tumorigen; Causes convulsions in lethal-dose feeding studies of rats; [RTECS] An irritant; Effects in high-dose animal studies include convulsions; [MSDSonline]
Hazard Classes and Categories · 3 件

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 · 1 件

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

化学と産業

用途と製造

Uses · 4 件

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.

Methods of ManufacturingEckenroth; Ber 27: 3410 (1894); Bischoff; Ber 35: 3434 (1902); Gomberg, Snow; J Am Chem Soc 47: 198 (1925).
Formulations/PreparationsGRADE: TECHNICAL
General Manufacturing InformationCarbonic acid, diphenyl ester: ACTIVE
応用分野 · 3 件

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 · 2 件

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

関連反応

212 件
反応記録を作成
HRID 4604 の反応式
HRID 4604反応物としてuspto-grants-1988_02
HRID 21852 の反応式
HRID 21852生成物としてuspto-grants-1995_06
HRID 65130 の反応式
HRID 65130生成物としてuspto-grants-1986_09
HRID 147801 の反応式
HRID 147801生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 156545 の反応式
HRID 156545生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 165721 の反応式
HRID 165721生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 182070 の反応式
HRID 182070反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 197504 の反応式
HRID 197504生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
1 / 27 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
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FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

Physical DescriptionWhite solid; [Hawley] White powder; [MSDSonline]

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.

Environmental Fate · 3 件

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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 件

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 · 1 件

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.

Artificial Pollution SourcesDiphenyl carbonate's production and use as a solvent for nitrocellulose(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 件

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 · 1 件

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).

Non-Human Toxicity ExcerptsQuestionable carcinogen with experimental neoplastigenic and tumorigenic data.
Environmental Abiotic Degradation · 1 件

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 · 1 件

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 · 1 件

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 · 2 件

/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)
一酸化炭素フェノールEfficient catalystsNiax* Catalyst C-31塩化カルボニル水素ビス(フェニルオキシ)カルシウム水酸化ナトリウム炭酸ビニレンテトラフェニルホスホニウムクロリド炭酸O-フェニルO-メチルphenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate3-tert-ブチルフェノールヘキサメチレンジイソシアナート

下流製品

ポリ(ビスフェノールAカルボナート)N-シアノカルボンイミド酸ジフェニル1,5-ジフェニルカルボノヒドラジド2,4-ビス[1-(4-ヒドロキシフェニル)-1-メチルエチル]フェノール4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one4,4'-(3,3,5-トリメチル-1,1-シクロヘキサンジイル)ビス(フェノール)1H-ベンズイミダゾール-7-カルボン酸, 1-[[2'-(2,5-ジヒドロ-5-オキソ-1,2,4-オキサジアゾール-3-イル)[1,1'-ビフェニル]-4-イル]メチル]-2-エトキシ-, メチルエステル

補足説明

定義ChEBI: A carbonate ester that is the diphenyl ester of carbonic acid.