큐멘

Cumene

HCID 7406CAS 101316-43-2

기본 정보

표준 SMILES
CC(C)c1ccccc1
InChIKey
RWGFKTVRMDUZSP-UHFFFAOYSA-N
분자식
C9H12
평균 분자량
120.19 g/mol
단동위원소 질량
120.09390038

개요

Cumene can cause cancer according to The National Toxicology Program.

이름 및 식별자

우선 이름
Cumene
IUPAC
cumene
현지명
큐멘
영어명
Cumene
분자식
C9H12
분자량
120.19

이름 및 동의어

CUMENEIsopropylbenzene98-82-82-Phenylpropane(1-Methylethyl)benzeneCumolBenzene, (1-methylethyl)-IsopropylbenzolCumeenIsopropilbenzeneIsopropylbenzeen2-Fenilpropano
이름 더 보기
쿠멘큐멘(1-메틸에틸)벤젠메틸 에틸 벤젠아이소프로필벤젠큐몰프로판-2-일벤젠쿠메네i-propylbenzeneIsopropylbenzen(1-methylethyl)-benzenIsopropylbenzene:Cumene
2-Fenyl-propaan(propan-2-yl)benzeneIsopropyl-benzolBenzene, isopropylPropane, 2-phenylPropan-2-ylbenzeneRCRA waste number U055Phenol bottoms

데이터베이스 식별자

CAS
101316-43-2、98-82-8
PubChem CID
7406
DTXSID
DTXSID1021827
ChEMBL
CHEMBL1398949
ChEBI
CHEBI:34656
UNII
8Q54S3XE7K
EC Number
202-704-5、309-848-9
Nikkaji
J3.581E

물성

구조 계산 물성

XLogP
3.7
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
1
무거운 원자 수
9

실험 및 물리화학적 성질

Chemical Classes · 3건

Hazardous Air Pollutants (HAPs)

Flammable agents - 3rd degree

Volatile Organic Compound (VOC) and(or) Waste-water effluent contaminant

SolventsSolvents -> Aromatic Solvents
CosmeticsCosmetics ingredient -> Other (Specify)
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 4건

log Kow = 3.66

3.66

3.66

3.66

물리화학적 성질

녹는점
96 °C · −96 °C(lit.)
끓는 점
152 · 152-154 °C(lit.)
밀도
0.864 g/mL · 0.864 g/mL at 25 °C(lit.)
증기 밀도
4.1 · 4.1 (vs air)
증기압
8 mm · 8 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.491(lit.)
화학적 성질 · 1건

cumene is oxidized to its hydroperoxide, which is used to produce propene oxide. The alcohol produced is subsequently converted back to cumene over a copper-chromium oxide catalyst to be reused in the process. The advantage of this process is that cumene is easier to hydroperoxidate (more stable).

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P301+P316, P303+P361+P353, P304+P340, P318, P319, P331, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 3187) of reports.

Danger

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

유해성 정보

Regulatory Information · 6건

Chemical: Benzene, (1-methylethyl)-

Hazard Traits - Carcinogenicity; Dermatotoxicity; Endocrine Toxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Ocular Toxicity

Benzene, (1-methylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, (1-methylethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 03-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15387

Benzene, (1-methylethyl)-: HSNO Approval: HSR001184 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Benzene, (1-methylethyl)-: Environment tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 4건

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 31 °C explosive vapour/air mixtures may be formed.

Fire PotentialFlammable liquid.
Health Hazards · 3건

Narcotic action with long-lasting effects; depressant to central nervous system. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

· May cause toxic effects if inhaled or absorbed through skin.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4건

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 4건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 4건

Excerpt from NIOSH Pocket Guide for Cumene:

General First Aid:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants and acids. Cool. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection · 3건

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

10.0 [ppm]

독성 정보

Body Burden · 2건

Isopropylbenzene has been detected at 0.13 ug/hour(1) and detected but not quantified(2) in human expired air from non-smoking individuals.

Isopropylbenzene concentration in air samples from non-smoking married females residing in New Jersey and Pennsylvania, in both smoking and nonsmoking homes and nonsmoking workplaces(1).[Table#628]

TreatmentTreatment is mainly symptomatic and supportive. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration. (A600)
Target Organs · 2건

Endocrine

Eyes, skin, respiratory system, central nervous system

Health EffectsPetroleum distillates are aspiration hazards and may cause pulmonary damage, central nervous system depression, and cardiac effects such as cardiac arrhythmias. They may also affect the blood, immune system, liver, and kidney. (A600, L1297)
Ecotoxicity Values · 5건

LC50; Species: Daphnia magna (Water flea); Concentration: 0.6 ppm for 48 hr /Conditions of bioassay not specified/

LD50; Species: Agelaius phoeniceus (red-winged blackbird) oral 98 mg/kg

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 25.4 °C, dissolved oxygen 6.6 mg/L, hardness 44.3 mg/L calcium carbonate, alkalinity 42.1 mg/L calcium carbonate, and pH 7.58; Concentration: 6.32 mg/L for 96 hr (confidence limit 6.04-6.61 mg/L)

EC50; Species: Pimephales promelas (fathead minnow); Condtions: flow-through bioassay with measured concentrations, 25.4 °C, dissolved oxygen 6.6 mg/L, hardness 44.3 mg/L calcium carbonate, alkalinity 42.1 mg/L calcium carbonate, and pH 7.58; Concentration: 6.32 mg/L for 96 hr (confidence limit 6.04-6.61 mg/L); Effect: loss of equilibrium. Affected fish lost schooling behavior and swam in a corkscrew/spiral pattern. They were hyperactive and darkly colored, had increased respiration, and lost equilibrium prior to death.

For more Ecotoxicity Values (Complete) data for Isopropylbenzene (14 total), please visit the HSDB record page.

Environmental Fate · 4건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 700(SRC), determined from a structure estimation method(2), indicates that isopropylbenzene is expected to have low mobility in soil(SRC). Volatilization of isopropylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.15X10-2 atm-cu m/mole(3). Isopropylbenzene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.5 mm Hg at 25 °C(4). A biodegradation half-life of 2 days (rate constant = 0.322/day) was calculated for isopropylbenzene added to soil microcosms from a weathered petroleum spill site(5), indicating that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 700(SRC), determined from a structure estimation method(2), indicates that isopropylbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.15X10-2 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hrs and 4 days, respectively(SRC). According to a classification scheme(5), a BCF of 35.5(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Isopropylbenzene, incubated in a sediment/freshwater ecocore, exhibited a mineralization rate of 0.02/day, corresponding to a half-life of 34.6 days(7), indicating that biodegradation may be an important environmental fate process in water(SRC).

AQUATIC FATE: In an experiment to study the disappearance of organic compounds found in crude oil during an oil spill, isopropylbenzene was found to disappear (combination of evaporation and dissolution) within 90 minutes of being spilled into seawater(1). In a similar experiment, water samples taken from an oil spill in the Canadian Arctic waters in the Ragged Channel revealed that after 6 hours, isopropylbenzene could not be detected in the aromatic fraction(2). Isopropylbenzene has a reported volatilization half-life in water ranging from 3.2 to 5.8 hrs(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropylbenzene, which has a vapor pressure of 4.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropylbenzene 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 1.5 days(SRC), calculated from its rate constant of 6.5X10-12 cu cm/molecule-sec at 25 °C(3). Isopropylbenzene exhibits a UV absorption of 258 nm in cyclohexane(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

규제 정보

RCRA Requirements · 1건

U055; As stipulated in 40 CFR 261.33, when cumene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Cumene is included on this list. Effective date: 12/28/84; Sunset date: 12/28/94.

Atmospheric Standards · 2건

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cumene is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Cumene is included on this list.

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

State Drinking Water Guidelines · 4건

(CA) CALIFORNIA 770 ug/l

(FL) FLORIDA 700 ug/l

(MN) MINNESOTA 300 ug/l

(NH) NEW HAMPSHIRE 800 ug/l

안전 데이터

OEB
A
OEL
TWA: 50 ppm (245 mg/m3) [skin]
wgk
1
IDLA
900 ppm [10% LEL]
tsca
TSCA listed
rtecs
GR8575000

화학 및 산업

약리 정보

Mechanism of Action · 1건

The alkylbenzenes, incl isopropyl benzene, were investigated for their property as sensory irritants in mice. A model for the sensory irritating action of alkylbenzenes was proposed on the basis of their physical interaction with a receptor protein in a lipid layer.

Biological Half-Life · 1건

Groups of Fischer 344 rats (minimum 4/sex/group) were studied after being exposed to radiolabeled cumene (>98% purity) either by single intravenous dose (35 mg/kg); single oral gavage doses (33 or 1,350 mg/kg); single 6-hr nose-only inhalation (100, 500, or 1,500 ppm); or eight daily oral gavage doses (33 mg/kg), with the eighth dose being radiolabeled. ... Elimination of cumene from the blood appeared as monoexponential with a half-life calculated between 9 to 16 hr for the gavage doses. The pattern of cumene disappearance from the blood in the inhalation studies also appeared to be monoexponential with the half-lives increasing with dose, from 3.9 hr at 100 ppm, to 4.6 hr at 500 ppm, to 6.6 hr at 1,200 ppm.

Metabolism/Metabolites · 6건

Cumene is absorbed readily by the mammalian system and oxidized at the side chain, one of the metabolites being the dimethylphenylcarbinol glucuronide.

In rabbits, 90% of a 2 mL oral dose was accounted for as side-chain oxidation products of cumene, which were excreted as glucuronide conjugates. About 40% of the dose was excreted as the glucuronide of 2-phenyl-2-propanol, 25% as the glucuronide of 2-phenyl-1-propanol, and 25% as the ester-glucuronide of 2-phenyl-propionic acid.

In the rat, (14)C-labeled cumene was administered either orally or by inhalation and was rapidly absorbed by either route. About 90% of the radiolabeled compound was excreted within 72 hours, mostly as conjugated metabolites in urine. The major urinary metabolites were 2-phenylpropan-2-ol, 2-phenylpropane-1,2-diol, and 2-phenylpropionic acid. Small amounts were also excreted in the feces and breath. Cumene and metabolites were widely distributed in the body after administration, with the highest amounts in fat, followed by kidney, liver, and bone.

Human volunteers (five men and five women) were exposed head-only for 8-hr periods to cumene vapors. Every 10 days, each subject was exposed to one of three different concentrations of cumene, 240, 480, or 720 mg/cu m. Samples of exhaled air were collected (method not clear from text) during exposures for estimation of respiratory tract retention, and urine was collected from each subject during exposure and for 40 hr thereafter. The mean respiratory tract retention was reported to be 50% (range, 45 to 64%), even at the highest concentration, although no data is given to support derivation of these values. Excretion of cumene, estimated from urinary amounts of 2-phenyl-2-propanol, was maximal after 6 to 8 hr of exposure and approached zero at 40 hr postexposure. The plot of time against urinary excretion of this metabolite revealed a rapid early phase (half life 2 hr) and a slower later phase (half life 10 hr). Approximately 35% of the calculated absorbed dose was excreted as 2-phenyl-2-propanol during the 8 hr of exposure and 40 hr postexposure.

For more Metabolism/Metabolites (Complete) data for Isopropylbenzene (7 total), please visit the HSDB record page.

Volatile hydrocarbons are absorbed mainly through the lungs, and may also enter the body after ingestion via aspiration. (A600)

Absorption, Distribution and Excretion · 5건

Groups of Fischer 344 rats (minimum 4/sex/group) were studied after being exposed to radiolabeled cumene (>98% purity) either by single intravenous dose (35 mg/kg); single oral gavage doses (33 or 1,350 mg/kg); single 6-hr nose-only inhalation (100, 500, or 1,500 ppm); or eight daily oral gavage doses (33 mg/kg), with the eighth dose being radiolabeled. The inhalation studies indicated rapid absorption, with detectable levels of cumene appearing in the blood within 5 min of the beginning of exposure. The gavage studies showed that cumene was absorbed readily via this route, with maximum blood levels occurring at the earliest time point sampled (4 hr) for the lower dose and at 8 to 16 hr for the higher dose. Elimination of cumene from the blood appeared as monoexponential with a half-life calculated between 9 to 16 hr for the gavage doses. The pattern of cumene disappearance from the blood in the inhalation studies also appeared to be monoexponential with the half-lives increasing with dose, from 3.9 hr at 100 ppm, to 4.6 hr at 500 ppm, to 6.6 hr at 1,200 ppm. Analysis of tissues (presumably immediately after exposure) indicated that several tissues, including adipose, liver, and kidney, all had elevated tissue/blood ratios of cumene, regardless of the route of cumene administration, indicating thorough distribution of cumene throughout the body independent of administration route. In general, very similar rates of elimination were observed across routes and exposure concentrations, with urine being the major route of elimination (70%) at any dose administered by any route. Total body clearance was rapid and complete, less than 1% of the absorbed fraction being present in the body 72 hr after the highest exposure regime examined, 1,200 ppm for 6 hr.

In the rat, (14)C-labeled cumene was administered either orally or by inhalation and was rapidly absorbed by either route. About 90% of the radiolabeled compound was excreted within 72 hours, mostly as conjugated metabolites in urine. ... Small amounts were also excreted in the feces and breath. Cumene and metabolites were widely distributed in the body after administration, with the highest amounts in fat, followed by kidney, liver, and bone.

Human volunteers (five men and five women) /were exposed/ head only to one of three different concentrations of cumene vapors (240, 480, or 720 mg/cu m ([49, 98, or 147 ppm)) for 8 hr every 10 days. Exhaled breath samples (10 cu cm) were collected near the beginning and at the end of the exposure from a tube placed in the breathing zone. The total amount of cumene absorbed during exposure, calculated from retention, ventilation, and exposure duration, was nearly twice as high at all exposure levels in the males (466-1400 mg) as in the females (270-789 mg). The respiratory tract absorption ranged from 45% to 64% depending on the time of exposure, with the overall mean retention estimated at 50%.

90% of an oral dose of cumene /was recovered as metabolites/ from rabbit urine.

For more Absorption, Distribution and Excretion (Complete) data for Isopropylbenzene (8 total), please visit the HSDB record page.

Cellular LocationsMembrane

용도 및 제조

Uses · 6건

Cumene is used as a thinner for paints, lacquers, and enamels and as a component of high octane fuels. Cumene is also used in the manufacture of phenol, acetone, acetophenone, and methylstyrene.

In occupational settings, the main route of exposure to cumene is via inhalation during cumene manufacturing, processing, and use, primarily in the manufacture of phenol and acetone. [ACGIH]

Painting (Solvents) [Category: Paint]

Used primarily in the production of phenol and acetone

Used as a thinner for paints, enamels, and lacquers and as a solvent for fats and resins and as such has been suggested as a replacement for benzene.

Component of high octane aviation fuel used in WWII; in production of styrene /Former/

ImpuritiesSulfur compounds 2 ppm, Max; Olefinic materials 200-700 ppm
U.S. Exports · 4건

(1972) NEGLIGIBLE

(1975) 2.07X10+10 GRAMS

(1984) 2.24X10+9 g

Exports totaled 465 million lbs in 1998.

U.S. Imports · 2건

(1972) 2.02X10+11 GRAMS

(1975) 9.50X10+10 GRAMS

U.S. Production · 6건

2023: 4,000,000,000 - <5,500,000,000 lb

(1972) 1.04X10+12 GRAMS

(1975) 9.09X10+11 GRAMS

(1984) 1.70X10+12 g

(1988) 4.5X10+9 lb

For more U.S. Production (Complete) data for Isopropylbenzene (13 total), please visit the HSDB record page.

Consumption Patterns · 5건

For phenol; 34% for acetone; 1% for alpha-methylstyrene and misc applications (1972)

Oxidation for phenol/acetone production; 1.8% polymerization for alpha-methylstyrene; 0.2% exports (1985)

CHEMICAL PROFILE: Cumene. Demand: 1986: 3.7 billion lb; 1987: 4.0 billion lb; 1991 /projected/: 4.3 billion lb. (Includes exports; in addition, 328 billion lb were imported in 1986).

More than 95% of the cumene produced is used as feedstock for the production of phenol and acetone.

Demand: 1998, 6.7 billion lbs; 1999, 6.9 billion lbs; 2003, 8.0 billion lbs

응용 분야 · 3건

개요Cumene is a common name for isopropylbenzene, an organic compound. Cumene is a volatile colorless liquid at room temperature with a characteristic sharp, penetrating, aromatic odor. It is insoluble in water but is soluble in alcohol and many other organic solvents. Cumene is structurally a member of the alkyl aromatic family of hydrocarbons, which also includes toluene (methylbenzene) and ethylbenzene.Cumene can be found in crude oil, refined fuels, and is a part of processed highoctane gasoline. Cumene is manufactured by reacting benzene with propylene at elevated temperature and pressure in the presence of a catalyst. It is considered an environmental pollutant because it is a natural component of petroleum and is present in tobacco smoke. Cumene vapor can be absorbed by the respiratory tract. Sufficiently high levels of exposure to cumene causes central nervous system (CNS) depression leading to death, internal bleeding of numerous organs, as well as irritation of the eyes and respiratory system, skin, and mucous membranes. Cumene is a high production volume chemical.

용도Around 98% of cumene is used in the production of phenol and its coproduct, acetone, using cumene hydroperoxide as chemical intermediate. However, the demand for cumene is largely dependent on the performance of phenol’s derivatives, which have resulted in healthy growth rates in demand for cumene. It is also used as a starting material in the production of acetophenone, α-methylstyrene, diisopropylbenzene, and dicumylperoxide. Cumene is used as a thinner for paints, lacquers, and enamels. It is also used in the manufacture of acetophenone, methylstyrene, and other chemicals commonly found in home cleaning products. Minor uses of cumene include as a constituent of some petroleum-based solvents, such as naphtha; in gasoline blending diesel fuel and highoctane aviation fuel; and as a raw material for peroxides and oxidation catalysts such as polymerization catalysts for acrylic and polyester-type resins. It is also a good solvent for fats and resins and has been suggested as a replacement for benzene in many of its industrial applications.

일반 설명Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

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334건

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