Benzene

Topics: Benzene, Toluene, Aromatic hydrocarbon Pages: 37 (8571 words) Published: December 17, 2013
Benzene

1

Benzene
Benzene

Identifiers
[1]

CAS number

71-43-2

PubChem

241

ChemSpider

236

UNII

J64922108F

EC number

200-753-7

KEGG

C01407

ChEBI

CHEBI:16716

ChEMBL

CHEMBL277500

RTECS number

CY1400000

Jmol-3D images

Image 1

 

[2]
[3]

 
[4]

 

[5]

[6]

 
[7]

 
[8]

 

[9]

Properties
Molecular formula

CH

Molar mass

78.11 g mol−1

Appearance

Colorless liquid

Odor

aromatic, gasoline-like

6 6

Benzene

2
Density

0.8765(20) g/cm3

Melting point

5.5 °C, 278.7 K, 41.9 °F

Boiling point

80.1 °C, 353.3 K, 176.18 °F

Solubility in water

1.79 g/L (15 °C)

Solubility

soluble in alcohol, chloroform, CCl4, diethyl ether, acetone

log P

2.13

Vapor pressure

10 kPa

λmax

255 nm

Magnetic susceptibility

54.8 x 10−6 cm3/mol

Refractive index (nD)

1.50108

Viscosity

0.652 cP at 20 °C

Dipole moment

0D
Thermochemistry

Std enthalpy of
o
formation ΔfH 298

48.7 kJ/mol

Standard molar
o
entropy S 298

173.26 J/K mol

Specific heat capacity, C

136.0 J/K mol
Hazards

MSDS

External MSDS

EU classification






R-phrases

R45, R46, R11, R16, R36/38,R48/23/24/25, R65

S-phrases

S53, S45

Flammable (F)
Carc. Cat. 1
Muta. Cat. 2
Toxic (T)

NFPA 704

Flash point

−11.63 °C; 11.07 °F; 261.52 K

Autoignition temperature

497.78 °C; 928.00 °F; 770.93 K

Explosive limits

1.2–7.8%

LD

930 mg/kg (rat, oral)

50

Related compounds
Related compounds




toluene
borazine

Supplementary data page
Structure and
properties

n, ε , etc.
r

Benzene

3
Thermodynamic
data

Phase behaviour
Solid, liquid, gas

Spectral data

UV, IR, NMR, MS
  (verify)

[10]

 (what is:  / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C or 77 °F, 100 kPa)

Infobox references

Benzene is an organic chemical compound with the molecular formula C6H6. Its molecule is composed of 6 carbon atoms joined in a ring, with 1 hydrogen atom attached to each carbon atom. Because its molecules contain only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of crude oil, and is one of the most elementary petrochemicals. Benzene is an aromatic hydrocarbon and the second [n]-annulene ([6]-annulene), a cyclic hydrocarbon with a continuous pi bond. It is sometimes abbreviated Ph–H. Benzene is a colorless and highly flammable liquid with a sweet smell. It is mainly used as a precursor to heavy chemicals, such as ethylbenzene and cumene, which are produced on a billion kilogram scale. Because it has a high octane number, it is an important component of gasoline, composing a few percent of its mass. Most non-industrial applications have been limited by benzene's carcinogenicity.

History
Discovery
The word "benzene" derives historically from "gum benzoin", sometimes called "benjamin" (i.e., benzoin resin), an aromatic resin known to European pharmacists and perfumers since the 15th century as a product of southeast Asia.[11] An acidic material was derived from benzoin by sublimation, and named "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene. Michael Faraday first isolated and identified benzene in 1825 from the oily residue derived from the production of illuminating gas, giving it the name bicarburet of hydrogen.[12] In 1833, Eilhard Mitscherlich produced it via the distillation of benzoic acid (from gum benzoin) and lime. He gave the compound the name benzin.[13]

In 1836, the French chemist Auguste Laurent named the substance "phène";[14] this is the root of the word phenol, which is hydroxylated benzene, and phenyl, which is the radical formed by abstraction of a hydrogen atom (free radical H•) from benzene.

In 1845, Charles...

References: [16] Mansfield, Charles Blachford (1849) "Untersuchung des Steinkohlentheers" (http:/ / books. google. com/ books?id=kD4aAQAAMAAJ&
pg=PA162) (Investigation of coal tar), Annalen der Chemie und Pharmacie, vol
[17] Charles Mansfield filed for (November 11, 1847) and received (May 1848) a patent (no. 11,960) for the fractional distillation of coal tar.
[19] J. Loschmidt, Chemische Studien (Vienna, Austria-Hungary: Carl Gerold 's Sohn, 1861), pp. 30, 65 (http:/ / books. google. com/
books?id=ksw5AAAAcAAJ& pg=PA30).
[21] Rocke, A. J. (2010) Image and Reality: Kekule, Kopp, and the Scientific Imagination, University of Chicago Press, pp. 186–227, ISBN
0226723356.
[23] Claus, Adolph K.L. (1867) Theoretische Betrachtungen und deren Anwendungen zur Systematik der organischen Chemie (Theoretical
considerations and their applications to the classification scheme of organic chemistry), Freiburg, Germany, p
[24] Dewar, James (1867) "On the oxidation of phenyl alcohol, and a mechanical arrangement adapted to illustrate structure in the non-saturated
hydrocarbons," (http:/ / books
[25] Ladenburg, Albert (1869) "Bemerkungen zur aromatischen Theorie" (http:/ / books. google. com/ books?id=Epg8AAAAIAAJ& pg=PA140)
(Observations on the aromatic theory), Berichte der Deutschen Chemischen Gesellschaft 2: 140–142.
[26] Armstrong, Henry E. (1887) "An explanation of the laws which govern substitution in the case of benzenoid compounds," (http:/ / books.
[27] Thiele, Johannes (1899) "Zur Kenntnis der ungesättigten Verbindungen" (On our knowledge of unsaturated compounds), Justus Liebig’s
Annalen der Chemie,306: 87–266; see: "VIII
125–129. (http:/ / books. google. je/ books?id=NYw8AAAAIAAJ& pg=RA1-PA125) See further: Thiele (1901) "Zur Kenntnis der
ungesättigen Verbindungen," Justus Liebig’s Annalen der Chemie, 319: 129–143.
[30] Gillis, Jean "Auguste Kekulé et son oeuvre, realisee a Gand de 1858 a 1867," Memoires de l 'Academie Royale de Belgique, 37:1 (1866),
1–40.
environmentalhealthnews. org/ ehs/ newscience/ benzene-linked-to-neural-tube-birth-defects/ ). Environmentalhealthnews.org (2010-10-26).
environmentalhealthnews. org/ ehs/ newscience/ benzene-linked-to-sperm-abnormalities). Environmentalhealthnews.org (2010-02-16).
osha. gov/ pls/ oshaweb/ owadisp. show_document?p_table=INTERPRETATIONS& p_id=24730). Osha.gov (2003-10-16). Retrieved on
2010-10-09.
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