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Cumene information


Cumene
Skeletal formula of cumene
Ball-and-stick model of the cumene molecule
Names
Preferred IUPAC name
(Propan-2-yl)benzene[1]
Other names
  • Isopropylbenzene
  • Cumol
  • (1-Methylethyl)benzene
Identifiers
CAS Number
  • 98-82-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1236613
ChEBI
  • CHEBI:34656 checkY
ChEMBL
  • ChEMBL1398949
ChemSpider
  • 7128 checkY
ECHA InfoCard 100.002.458 Edit this at Wikidata
EC Number
  • 202-704-5
KEGG
  • C14396 checkY
PubChem CID
  • 7406
RTECS number
  • GR8575000
UNII
  • 8Q54S3XE7K checkY
UN number 1918
CompTox Dashboard (EPA)
  • DTXSID1021827 Edit this at Wikidata
InChI
  • InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 checkY
    Key: RWGFKTVRMDUZSP-UHFFFAOYSA-N checkY
  • InChI=1/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3
    Key: RWGFKTVRMDUZSP-UHFFFAOYAJ
SMILES
  • CC(C)c1ccccc1
Properties
Chemical formula
C9H12
Molar mass 120.195 g·mol−1
Appearance colorless liquid
Odor sharp, gasoline-like
Density 0.862 g cm−3, liquid
Melting point −96 °C (−141 °F; 177 K)
Boiling point 152 °C (306 °F; 425 K)
Solubility in water
negligible
Solubility soluble in acetone, ether, ethanol
Vapor pressure 4.5 mmHg (25°C)[2]
Magnetic susceptibility (χ)
-89.53·10−6 cm3/mol
Refractive index (nD)
1.4915 (20 °C)
Viscosity 0.777 cP (21 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
flammable
GHS labelling:
Pictograms
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word
Warning
Hazard statements
H226, H302, H304, H312, H314, H332, H335, H341, H412, H441
Precautionary statements
P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
Flash point 43 °C (109 °F; 316 K)
Autoignition
temperature
424 °C (795 °F; 697 K)
Explosive limits 0.9-6.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
12750 mg/kg (oral, mouse)
1400 mg/kg (oral, rat)[4]
LC50 (median concentration)
200 ppm (mouse, 7 hr)[4]
LCLo (lowest published)
8000 ppm (rat, 4 hr)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 50 ppm (245 mg/m3) [skin][3]
REL (Recommended)
TWA 50 ppm (245 mg/m3) [skin][3]
IDLH (Immediate danger)
900 ppm[3]
Related compounds
Related compounds
ethylbenzene
toluene
benzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone (known as the cumene process).

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 139, 597. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, D.C.: Taylor and Francis. 1989.
  3. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0159". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b c "Cumene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

and 24 Related for: Cumene information

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Cumene

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Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined...

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Cumene process

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The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term...

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Cumene hydroperoxide

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Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH. An oily liquid, it is classified as an organic hydroperoxide. Products of...

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Phenol

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for its production, but the cumene process is the dominant technology. Accounting for 95% of production (2003) is the cumene process, also called Hock process...

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Petrochemical

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styrene as a monomer cumene – isopropylbenzene; a feedstock in the cumene process phenol – hydroxybenzene; often made by the cumene process acetone – dimethyl...

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Reaction intermediate

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reactive intermediates. It is also used more widely for chemicals such as cumene which are traded within the chemical industry but are not generally of value...

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Organic peroxides

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in major commercial processes. In the cumene process, acetone and phenol are produced by decomposition of cumene hydroperoxide (Me = methyl): C6H5CMe2(O2H)...

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Hydroperoxide

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vs tert-BuOH (b.p. 82-83 °C) CH3OOH (b.p. 46 °C) vs CH3OH (b.p. 65 °C) cumene hydroperoxide (b.p. 153 °C) vs cumyl alcohol (b.p. 202 °C) Hydroperoxides...

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Acetophenone

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useful resins and fragrances. Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In...

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Benzene

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manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene...

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Propylene oxide

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dehydrated to give styrene, a useful monomer. Cumene hydroperoxide derived from oxygenation of cumene (isopropylbenzene), which affords cumyl alcohol...

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Isopropyl alcohol

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above methods, as acetone is itself normally prepared from propene via the cumene process. IPA cost is primarily driven by raw material (acetone or propylene)...

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Naphtha

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reddish brown liquid that is a mixture of hydrocarbons (toluene, xylene, and cumene, etc.), could also be intended in some contexts. In older usage,[when?]...

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Acetone

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acetone is produced via the cumene process; as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated...

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Propylene

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production of important chemicals such as propylene oxide, acrylonitrile, cumene, butyraldehyde, and acrylic acid. In the year 2013 about 85 million tonnes...

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Dicumyl peroxide

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It is synthesized as a by-product in the autoxidation of cumene, which mainly affords cumene hydroperoxide. Alternatively, it can be produced by the addition...

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Calcium acetate

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starting material for the synthesis of acetone before the development of the cumene process: Ca(CH3COO)2 → CaCO3(s) + (CH3)2CO A saturated solution of calcium...

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Methylaluminoxane

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as a solution in (aromatic) solvents, commonly toluene but also xylene, cumene, or mesitylene, Used in large excess, it activates precatalysts for alkene...

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Hydroquinone

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industrially in two main ways. The most widely used route is similar to the cumene process in reaction mechanism and involves the dialkylation of benzene with...

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Cyclohexylbenzene

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analogous to the cumene process begins with cyclohexylbenzene, which is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide. Via...

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Hydrotrope

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estimated to be 1.42 ug/Kg bw/day. Calcium xylene sulfonate and sodium cumene sulfonate have been shown to cause temporary, slight eye irritation in animals...

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Alkylation

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fundamental benzene-based feedstocks such as ethylbenzene (precursor to styrene), cumene (precursor to phenol and acetone), linear alkylbenzene sulfonates (for detergents)...

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Ethylbenzene hydroperoxide

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organic synthesis. It is chiral. Together with tert-butyl hydroperoxide and cumene hydroperoxide, ethylbenzene hydroperoxide is important commercially. The...

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Ketone

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aerobic oxidation of cyclohexane. Acetone is prepared by air-oxidation of cumene. For specialized or small scale organic synthetic applications, ketones...

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