Cumene

Cumene  | Skeletal formula of cumene | Ball-and-stick model of the cumene molecule

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Names
Preferred IUPAC name

(Propan-2-yl)benzene[1]

Other names

* Isopropylbenzene
* Cumol
* (1-Methylethyl)benzene

Identifiers

CAS Number

* 98-82-8 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1236613
ChEBI |

* CHEBI:34656 Y

ChEMBL |

* ChEMBL1398949

ChemSpider |

* 7128 Y

EC Number |

* 202-704-5

KEGG |

* C14396 Y

PubChem CID

* 7406

RTECS number |

* GR8575000

UNII |

* 8Q54S3XE7K Y

UN number | 1918

InChI

* InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 Y

Key: RWGFKTVRMDUZSP-UHFFFAOYSA-N Y

* 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
Main hazards | flammable
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H226, H302, H304, H312, H314, H332, H335, H341, H412, H441Script error: No such module "Preview warning".Category:GHS errors

GHS precautionary statements

| P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P308+313, P310, P312, P321, P322, P330, P363, P405
NFPA 704 (fire diamond)  |

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).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

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).

## Contents

* 1 Production
* 2 Autoxidation
* 3 Applications
* 4 See also
* 5 References
* 6 External links

## Production

Commercial production of cumene is by Friedel–Crafts alkylation of benzene with propylene. The original route for manufacturing of cumene was by alkylation of benzene in the liquid phase using sulfuric acid as a catalyst, but because of the complicated neutralization and recycling steps required, together with corrosion problems, this process has been largely replaced. As an alternative, solid phosphoric acid (SPA) supported on alumina was used as the catalyst.

Reaction of benzene with propene to cumene in the presence of phosphoric acid supported on silica & promoted with boron trifluoride

Since the mid-1990s, commercial production has switched to zeolite-based catalysts. In this process, the efficiency of cumene production is generally 70-75%. The remaining components are primarily polyisopropyl benzenes. In 1976, an improved cumene process that uses aluminum chloride as a catalyst was developed. The overall conversion of cumene for this process can be as high as 90%.

The addition of two equivalents of propylene gives diisopropylbenzene (DIPB). Using transalkylation, DIPB is comproportionated with benzene to give cumene.[5]

## Autoxidation

Depending on the conditions, autoxidation of cumene gives dicumyl peroxide or cumene hydroperoxide. Both reactions exploit the weakness of the tertiary C-H bond. The tendency of cumene to form peroxides by autoxidation poses safety concerns.[6] Tests for peroxides are routinely conducted before heating or distilling.

## Applications

Cumene is frequently found as an ingredient in thread locking fluids.[7][8]

## See also

* Pseudocumene

## References

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. ↑ 3.0 3.1 3.2 NIOSH Pocket Guide to Chemical Hazards. "#0159". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0159.html.
4. ↑ 4.0 4.1 4.2 "Cumene". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/idlh/98828.html.
5. ↑ Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Kirk-Othmer Encyclopedia of Chemical Technology". Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0471238961.
6. ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
7. ↑ "LOCTITE 242 MS TL Safety Data Sheet". https://pim.henkelgroup.net/henkel/sds/A/135354/US/EN.
8. ↑ "Wurth Blue Thread Locker Safety Data Sheet". https://ehs.wuerth.com/ehs4customers/export/04093831.PDF.

## External links

* National Pollutant Inventory - Cumene fact sheet
* Cumene Production from Benzene and Propylene Using Aluminum Chloride Catalyst

* v
* t
* e

Hydrocarbons

Saturated
aliphatic
hydrocarbons|

| Alkanes
CnH2n \+ 2|

| Linear alkanes|

* Methane
* Ethane
* Propane
* Butane
* Pentane
* Hexane
* Heptane
* Octane
* Nonane
* Decane

|

Branched alkanes|

* Isobutane
* Isopentane
* 3-Methylpentane
* Neopentane
* Isohexane
* Isoheptane
* Isooctane
* Isononane
* Isodecane

Cycloalkanes|

* Cyclopropane
* Cyclobutane
* Cyclopentane
* Cyclohexane
* Cycloheptane
* Cyclooctane
* Cyclononane
* Cyclodecane

Alkylcycloalkanes|

* Methylcyclopropane
* Methylcyclobutane
* Methylcyclopentane
* Methylcyclohexane
* Isopropylcyclohexane

Bicycloalkanes|

* Housane (bicyclo[2.1.0]pentane)
* Norbornane (bicyclo[2.2.1]heptane)
* Decalin (bicyclo[4.4.0]decane)

Polycycloalkanes|

* Adamantane
* Diamondoid
* Perhydrophenanthrene
* Sterane
* Cubane
* Prismane
* Dodecahedrane
* Basketane
* Churchane
* Pagodane
* Twistane

Other|

* Spiroalkanes

Unsaturated
aliphatic
hydrocarbons|

| Alkenes
CnH2n|

| Linear alkenes|

* Ethene
* Propene
* Butene
* Pentene
* Hexene
* Heptene
* Octene
* Nonene
* Decene

|

Branched alkenes|

* Isobutene
* Isopentene
* Isohexene
* Isoheptene
* Isooctene
* Isononene
* Isodecene

Alkynes
CnH2n − 2|

| Linear alkynes|

* Ethyne
* Propyne
* Butyne
* Pentyne
* Hexyne
* Heptyne
* Octyne
* Nonyne
* Decyne

|

Branched alkynes|

* Isopentyne
* Isohexyne
* Isoheptyne
* Isooctyne
* Isononyne
* Isodecyne

Cycloalkenes|

* Cyclopropene
* Cyclobutene
* Cyclopentene
* Cyclohexene
* Cycloheptene
* Cyclooctene
* Cyclononene
* Cyclodecene

Alkylcycloalkenes|

* Methylcyclopropene
* Methylcyclobutene
* Methylcyclopentene
* Methylcyclohexene
* Isopropylcyclohexene

Bicycloalkenes|

* Norbornene

Cycloalkynes|

* Cyclopropyne
* Cyclobutyne
* Cyclopentyne
* Cyclohexyne
* Cycloheptyne
* Cycloctyne
* Cyclononyne
* Cyclodecyne

Dienes|

* Propadiene
* Butadiene
* Pentadiene
* Hexadiene
* Heptadiene
* Octadiene
* Nonadiene
* Decadiene

Other|

* Alkatriene
* Alkadiyne
* Cumulene
* Cyclooctatetraene
* Cyclododecatriene
* Enyne

Aromatic
hydrocarbons|

| PAHs|

| Acenes|

* Naphthalene
* Anthracene
* Tetracene
* Pentacene
* Hexacene
* Heptacene

|

Other|

* Azulene
* Fluorene
* Helicenes
* Circulenes
* Butalene
* Phenanthrene
* Chrysene
* Pyrene
* Corannulene
* Kekulene

Alkylbenzenes|

* Toluene
* Xylene
* Ethylbenzene
* Cumene
* Styrene
* Mesitylene
* Pseudocumene
* Hemellitene
* Cymene
* Hexamethylbenzene

Other|

* Benzene
* Cyclopropenylidene

Other|

* Annulenes
* Annulynes
* Alicyclic compounds
* Petroleum jelly

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Original source: https://en.wikipedia.org/wiki/Cumene. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Cumene&oldid=440545"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H302]: Harmful if swallowed
*[H304]: May be fatal if swallowed and enters airways
*[H312]: Harmful in contact with skin
*[H314]: Causes severe skin burns and eye damage
*[H332]: Harmful if inhaled
*[H335]: May cause respiratory irritation
*[H341]: Suspected of causing genetic defects
*[H412]: Harmful to aquatic life with long lasting effects
*[P201]: Obtain special instructions before use
*[P202]: Do not handle until all safety precautions have been read and understood
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P281]: Use personal protective equipment as required
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+312]: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P308+313]: IF exposed or concerned: Get medical advice/attention
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P363]: Wash contaminated clothing before reuse
*[P405]: Store locked up
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