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디페닐 카르보네이트

Diphenyl carbonate

HCID 7597
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
102-09-0
표준 SMILES
O=C(Oc1ccccc1)Oc1ccccc1
InChIKey
ROORDVPLFPIABK-UHFFFAOYSA-N
분자식
C13H10O3
평균 분자량
214.22 g/mol
단동위원소 질량
214.06299418

개요

Diphenyl carbonate is a carbonate ester that is the diphenyl ester of carbonic acid.

이름 및 식별자

우선 이름
Diphenyl carbonate
IUPAC
diphenyl carbonate
현지명
디페닐 카르보네이트
영어명
Diphenyl carbonate
분자식
C13H10O3
분자량
214.22

이름 및 동의어

DIPHENYL CARBONATE102-09-0Carbonic acid, diphenyl esterPhenyl carbonateCarbonic Acid Diphenyl EsterPhenyl carbonate ((PhO)2CO)Ph2CO3HSDB 5346(PhO)2COYWV401IDYNEINECS 203-005-8NSC 37087
이름 더 보기
디페닐카르보네이트디페닐카르보네이트DPCDiphenyl carbonate, 99.50%AURORA 16157DiphenylcarbonatPhenol carbonateDiphenyl carboteiphenylcarbonateDIFENILCARBONATO
BRN 1074863AI3-00063NSC-37087DIPHENYL CARBONATE [MI]CHEBI:34722DIPHENYL CARBONATE [HSDB]EC 203-005-8PHENYL CARBONATE [(PHO)2CO]

데이터베이스 식별자

CAS
102-09-0
PubChem CID
7597
DTXSID
DTXSID3020540
ChEMBL
CHEMBL3188080
ChEBI
CHEBI:34722
UNII
YWV401IDYN
EC Number
203-005-8
Nikkaji
J5.004K

물성

구조 계산 물성보충 중

XLogP
3.3
극성 표면적
35.5 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
4
무거운 원자 수
16
형식 전하
0
복잡도
193

실험 및 물리화학적 성질

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

Lustrous needles

WHITE, CRYSTALLINE SOLID

Solubility · 2건

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 · 2건

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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]

유해성 정보

Regulatory Information · 3건

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 · 3건

Acute Tox. 4 (94.9%)

Acute toxicity (Oral) - Category 4

Hazardous to the aquatic environment (Acute) - Category 2

안전 및 보호

Disposal Methods · 1건

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.

독성 정보

화학 및 산업

용도 및 제조

Uses · 4건

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

응용 분야

용도Estrogenic activity of Diphenyl Carbonate by yeast 2-hybrid assay was studied.

제조 방법 · 1건

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.

상·하류 제품 정보

상류 원료

일산화탄소(가스)페놀

관련 반응

212건
반응 기록 만들기
HRID 4604 반응식
HRID 4604반응물로uspto-grants-1988_02
HRID 21852 반응식
HRID 21852생성물로uspto-grants-1995_06
HRID 65130 반응식
HRID 65130생성물로uspto-grants-1986_09
HRID 147801 반응식
HRID 147801생성물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 156545 반응식
HRID 156545생성물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 165721 반응식
HRID 165721생성물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 182070 반응식
HRID 182070반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 197504 반응식
HRID 197504생성물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
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FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

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

물리화학적 성질

녹는점
79 · 79-82 °C (lit.)
끓는 점
301 · 301-302 °C (lit.)
밀도
1 · 1,3 g/cm3
증기압
0.014 Pa · 0.014Pa at 20℃
굴절률
1.509 · 1.5090 (estimate)
인화점
168 °C · 168 °C
저장 조건
Sealed in dry,Room Temperature
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
플레이크 또는 결정성 분말
색상
하얀색
수용성
불용성
Merck
14 · 14,7278
BRN
1074863 · 1074863
Henry's Law Constant
1.2 · 1.2×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
안정적인. 강한 산화제와 호환되지 않습니다. 가연성.
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℃
NIST
Diphenyl carbonate(102-09-0)
EPA
Carbonic acid, diphenyl ester (102-09-0)

화학적 성질

white solid

Environmental Fate · 3건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 2건

/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/

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
FG0500000
ridadr
3077
독성
rat,LD50,oral,1500mg/kg (1500mg/kg),BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD,National Technical Information Service. Vol. OTS0540144,
HS 번호
29209010
risk_code
22-20
hazard_code
Xn
safety_code
22-24/25
포장분류
III
위험 등급
9
기존화학 물질
2017-3-7253
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2
스토리지 클래스
13 - Non Combustible Solids
유해 물질 데이터
102-09-0(Hazardous Substances Data)
Efficient catalysts
Niax* Catalyst C-31
포스겐
수소
칼슘 페산화물
수산화나트륨
바이닐렌 카보네이트
테트라페닐 인 클로라이드
Methyl phenyl carbonate
phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate
M-삼차-뷰틸페놀
헥사메틸렌디이소시아네이트

하류 제품

폴리(비스페놀 A 탄산)Diphenyl N-cyanocarbonimidate1,5-디페닐카보노히드라지드2,4-bis[1-(4-hydroxyphenyl)isopropyl]phenol4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-oneBisphenol TMC1H-BenziMidazole-7-carboxylic acid, 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]Methyl] -2-ethoxy-, Methyl ester

추가 설명

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