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This article is about the chemical compound. For other radical formed by abstraction of a hydrogen atom (free
uses, see Benzene (disambiguation).
radical H) from benzene.
Not to be confused with Benzine.
Benzene is an organic chemical compound with the
molecular formula C6 H6 . 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
Historic benzene formulae as proposed by Kekul.[15]
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 PhH. Benzene is a
colorless and highly ammable 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, comprising a
few percent of its mass. Most non-industrial applications
have been limited by benzenes carcinogenicity.
In 1845, Charles Manseld, working under August Wilhelm von Hofmann, isolated benzene from coal tar.[16]
Four years later, Manseld began the rst industrialscale production of benzene, based on the coal-tar
method.[17][18] Gradually the sense developed among
chemists that substances related to benzene represent a
diverse chemical family. In 1855 August Wilhelm Hofmann used the word "aromatic" to designate this family
relationship, after a characteristic property of many of its
members.[19]
In 1997, benzene was detected in deep space.[20]
1
1.1
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.[9] An acidic material was derived from benzoin
by sublimation, and named owers of benzoin, or benzoic acid. The hydrocarbon derived from benzoic acid
thus acquired the name benzin, benzol, or benzene.[10]
2
carbon-hydrogen ratio.[25]
The new understanding of benzene, and hence of all aromatic compounds, proved to be so important for both
pure and applied chemistry that in 1890 the German
Chemical Society organized an elaborate appreciation in
Kekul's honor, celebrating the twenty-fth anniversary
of his rst benzene paper. Here Kekul spoke of the creation of the theory. He said that he had discovered the
ring shape of the benzene molecule after having a reverie
or day-dream of a snake seizing its own tail (this is a
common symbol in many ancient cultures known as the
Ouroboros or Endless knot).[31] This vision, he said, came
to him after years of studying the nature of carbon-carbon
bonds. This was 7 years after he had solved the problem of how carbon atoms could bond to up to four other
atoms at the same time. It is curious that a similar, humorous depiction of benzene had appeared in 1886 in the
Berichte der Durstigen Chemischen Gesellschaft (Journal
of the Thirsty Chemical Society), a parody of the Berichte
der Deutschen Chemischen Gesellschaft, only the parody
had monkeys seizing each other in a circle, rather than
snakes as in Kekul's anecdote.[32] Some historians have
suggested that the parody was a lampoon of the snake
anecdote, possibly already well known through oral transmission even if it had not yet appeared in print.[10] (Some
others have speculated that Kekul's story in 1890 was a
re-parody of the monkey spoof, and was a mere invention
rather than a recollection of an event in his life.) Kekul's
1890 speech[33] in which these anecdotes appeared has
been translated into English.[34] If the anecdote is the
memory of a real event, circumstances mentioned in the
story suggest that it must have happened early in 1862.[35]
2 STRUCTURE
tion of Sanka. This process was later discontinued. Benzene was historically used as a signicant component in
many consumer products such as Liquid Wrench, several
paint strippers, rubber cements, spot removers and other
hydrocarbon-containing products. Some ceased manufacture of their benzene-containing formulations in about
1950, while others continued to use benzene as a component or signicant contaminant until the late 1970s when
leukemia deaths were found associated with Goodyears
Pliolm production operations in Ohio. Until the late
1970s, many hardware stores, paint stores, and other retail outlets sold benzene in small cans, such as quart size,
for general-purpose use. Many students were exposed to
benzene in school and university courses while performing laboratory experiments with little or no ventilation in
many cases. This very dangerous practice has been almost totally eliminated.
2 Structure
Main article: Aromaticity
Benzene represents a special problem in that, to account
for the bond lengths quantitatively, there must either be
electron delocalization (molecular orbital theory) or a spin
coupling of the p-orbitals (valence bond theory):[38]
H
C6H6
Benzene
Molecular formula
Sigma Bonds
sp2 Hybridized orbitals
c
c
c
H
c
c
c
c
c
c
Kekul Structures H
(Isomers)
6 pz orbitals
delocalized pi
system
120
140
pm
Planar Hexagon
Bond Length 140 pm
Benzene ring
Simplied depiction
4.1
Catalytic reforming
bonding, benzene is often depicted with a circle inside a ing produced from coal.
hexagonal arrangement of carbon atoms.
As is common in organic chemistry, the carbon atoms
in the diagram above have been left unlabeled. Realizing each carbon has 2p electrons, each carbon donates
an electron into the delocalized ring above and below the
benzene ring. It is the side-on overlap of p-orbitals that
produces the pi clouds.
Derivatives of benzene occur suciently often as a component of organic molecules that there is a Unicode symbol in the Miscellaneous Technical block with the code
U+232C () to represent it with three double bonds,[44]
and U+23E3 () for a delocalized version.[45]
Benzene derivatives
Main articles:
Alkylbenzenes
Aromatic
hydrocarbons
and
Production
6 REACTIONS
A typical reaction yield exceeds 95%. Sometimes, make some types of rubbers, lubricants, dyes, detergents,
xylenes and heavier aromatics are used in place of drugs, explosives, and pesticides.
toluene, with similar eciency.
In both the US and Europe, 50% of benzene is used in the
This is often called on-purpose methodology to pro- production of ethylbenzene/styrene, 20% is used in the
duce benzene, compared to conventional BTX (benzene- production of cumene, and about 15% of benzene is used
toluene-xylene) extraction processes.
in the production of cyclohexane (eventually to nylon).
4.3
Toluene disproportionation
4.4
Steam cracking
4.5
Other sources
Trace amounts of benzene may result whenever carbonrich materials undergo incomplete combustion. It is produced in volcanoes and forest res, and is also a component of cigarette smoke. Benzene is a principal product
from the combustion of PVC (polyvinyl chloride).
Uses
6 Reactions
The most common reactions of benzene involve substitution of a proton by other groups.[48] Electrophilic aromatic substitution is a general method of derivatizing benzene. Benzene is suciently nucleophilic that it undergoes substitution by acylium ions and alkyl carbocations
to give substituted derivatives.
AlCl3
CH3
+ HCl
Cl
6.1
Using electrophilic aromatic substitution, many functional groups are introduced onto the benzene framework.
Sulfonation of benzene involves the use of oleum, a mixture of sulfuric acid with sulfur trioxide. Sulfonated benzene derivatives are useful detergents. In nitration, benzene reacts with nitronium ions (NO2 + ), which is a strong
electrophile produced by combining sulfuric and nitric
acids. Nitrobenzene is the precursor to aniline. Chlorination is achieved with chlorine to give chlorobenzene in
the presence of a catalyst such as aluminium trichloride.
6.2
Hydrogenation
6.3
Metal complexes
7 Health eects
Benzene increases the risk of cancer and other illnesses.
Benzene is a notorious cause of bone marrow failure.
Substantial quantities of epidemiologic, clinical, and
laboratory data link benzene to aplastic anemia, acute
leukemia, and bone marrow abnormalities.[50][51] The
specic hematologic malignancies that benzene is associated with include: acute myeloid leukemia (AML),
aplastic anemia, myelodysplastic syndrome (MDS), acute
lymphoblastic leukemia (ALL), and chronic myeloid
leukemia (CML).[52]
The American Petroleum Institute (API) stated in 1948
that it is generally considered that the only absolutely
safe concentration for benzene is zero.[53] The US Department of Health and Human Services (DHHS) classies benzene as a human carcinogen. Long-term exposure
to excessive levels of benzene in the air causes leukemia,
a potentially fatal cancer of the blood-forming organs,
in susceptible individuals. In particular, Acute myeloid
leukemia or acute nonlymphocytic leukemia (AML &
ANLL) is not disputed to be caused by benzene.[54] IARC
rated benzene as known to be carcinogenic to humans
(Group 1).
Human exposure to benzene is a global health problem.
Benzene targets liver, kidney, lung, heart and the brain
and can cause DNA strand breaks, chromosomal damage, etc. Benzene causes cancer in animals including humans. Benzene has been shown to cause cancer in both
EXPOSURE TO BENZENE
sexes of multiple species of laboratory animals exposed products, in general, focus on specic toxic constituents.
via various routes.[55][56]
The petroleum constituents of primary interest to huSome women who inhaled high levels of benzene for man health have been the aromatic hydrocarbons (i.e.,
many months had irregular menstrual periods and a de- benzene, ethylbenzene, toluene, and xylenes). In the
crease in the size of their ovaries. Benzene exposure has U.S., OSHA requires that a mixture shall be assumed to
been linked directly to the neural birth defects spina bi- present a carcinogenic hazard if it contains a component
0.1% or greater, which is considered
da and anencephaly.[57] Men exposed to high levels of in concentrations of[59][60]
to
be
a
carcinogen.
benzene are more likely to have an abnormal amount of
chromosomes in their sperm, which impacts fertility and Outdoor air may contain low levels of benzene from aufetal development.[58]
tomobile service stations, wood smoke, tobacco smoke,
the transfer of gasoline, exhaust from motor vehicles, and
industrial emissions.[61] About 50% of the entire nationwide (United States) exposure to benzene results from
8 Exposure to benzene
smoking tobacco or from exposure to tobacco smoke.[62]
8.1 Inhalation
Inhaled benzene is primarily expelled unchanged through
exhalation. In a human study 16.4 to 41.6% of retained
benzene was eliminated through the lungs within ve to
seven hours after a two- to three-hour exposure to 47 to
110 ppm and only 0.07 to 0.2% of the remaining benzene
was excreted unchanged in the urine. After exposure to
63 to 405 mg/m3 of benzene for 1 to 5 hours, 51 to 87%
was excreted in the urine as phenol over a period of 23 to
50 hours. In another human study, 30% of absorbed dermally applied benzene, which is primarily metabolized in
the liver, was excreted as phenol in the urine.[63]
8.6
Exposure monitoring
8.4
Case examples
8.5
8.7
Biomarkers of exposure
Several tests can determine exposure to benzene. Benzene itself can be measured in breath, blood or urine,
but such testing is usually limited to the rst 24 hours
post-exposure due to the relatively rapid removal of the
chemical by exhalation or biotransformation. Most persons in developed countries have measureable baseline
levels of benzene and other aromatic petroleum hydrocarbons in their blood. In the body, benzene is enzymatically converted to a series of oxidation products including
muconic acid, phenylmercapturic acid, phenol, catechol,
hydroquinone and 1,2,4-trihydroxybenzene. Most of
these metabolites have some value as biomarkers of human exposure, since they accumulate in the urine in proportion to the extent and duration of exposure, and they
may still be present for some days after exposure has
ceased. The current ACGIH biological exposure limits
for occupational exposure are 500 g/g creatinine for muconic acid and 25 g/g creatinine for phenylmercapturic
acid in an end-of-shift urine specimen.[78][79][80][81]
8.8
Biotransformations
EXPOSURE TO BENZENE
8.11 Summary
According to the Agency for Toxic Substances and Disease Registry (ATSDR) (2007), benzene is both an anthropogenically produced and naturally occurring chemical from processes that include: volcanic eruptions, wild
res, synthesis of chemicals such as phenol, production
of synthetic bers, and fabrication of rubbers, lubricants,
Genetic polymorphisms in these enzymes may induce loss pesticides, medications, and dyes. The major sources
9
of benzene exposure are tobacco smoke, automobile service stations, exhaust from motor vehicles, and industrial
emissions; however, ingestion and dermal absorption of
benzene can also occur through contact with contaminated water. Benzene is hepatically metabolized and excreted in the urine. Measurement of air and water levels
of benzene is accomplished through collection via activated charcoal tubes, which are then analyzed with a gas
chromatograph. The measurement of benzene in humans
can be accomplished via urine, blood, and breath tests;
however, all of these have their limitations because benzene is rapidly metabolized in the human body into byproducts called metabolites.[87]
OSHA regulates levels of benzene in the workplace.[88]
The maximum allowable amount of benzene in workroom air during an 8-hour workday, 40-hour workweek is
1 ppm. Because benzene can cause cancer, NIOSH recommends that all workers wear special breathing equipment when they are likely to be exposed to benzene at levels exceeding the recommended (8-hour) exposure limit
of 0.1 ppm.[89]
6-membered aromatic rings with one carbon replaced by another group: borabenzene, benzene, silabenzene, germabenzene, stannabenzene,
pyridine, phosphorine, arsabenzene, pyrylium salt
American
10
[5] http://chemister.ru/Database/properties-en.php?dbid=
1&id=644
[6] Seidell, Atherton; Linke, William F. (1952). [Google
Books Solubilities of Inorganic and Organic Compounds].
Van Nostrand. Retrieved 2014-05-29.
[7] Benzene in Linstrom, P.J.; Mallard, W.G. (eds.) NIST
Chemistry WebBook, NIST Standard Reference Database
Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-05-29)
[8] Sigma-Aldrich Co., Benzene. Retrieved on 2014-05-29.
[9] The word benzoin is derived from the Arabic expression
"luban jawi", or "frankincense of Java". Morris, Edwin T.
(1984). Fragrance: The Story of Perfume from Cleopatra to Chanel. Charles Scribners Sons. p. 101. ISBN
0684181959.
[10] Rocke, A. J. (1985).
Hypothesis and Experiment in the Early Development of Kekules Benzene Theory. Annals of Science 42 (4): 35581.
doi:10.1080/00033798500200411.
See also
References
10
10
REFERENCES
11
[49] Welch, Vincent A.; Fallon, Kevin J. and Gelbke, HeinzPeter (2005) Ethylbenzene in Ullmanns Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim,
doi:10.1002/14356007.a10_035.pub2
[50] Kasper, Dennis L.et al. (2004) Harrisons Principles of
Internal Medicine, 16th ed., McGraw-Hill Professional, p.
618, ISBN 0071402357.
[51] Merck Manual, Home Edition, Overview of Leukemia.
[52] Smith, Martyn T. (2010).
Advances in understanding benzene health eects and susceptibility.
Ann Rev Pub Health 31:
13348.
doi:10.1146/annurev.publhealth.012809.103646.
[53] American Petroleum Institute, API Toxicological Review,
Benzene, September 1948, Agency for Toxic Substances
and Disease Registry, Department of Health and Human
Services
[54] WHO. International Agency for Research on Cancer,
IARC Monographs on the Evaluation of Carcinogenic
Risks to Humans, Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs, Volumes 1 to
42, Supplement 7
[55] Hu J (2007). Benzene-induced cancers: abridged history and occupational health impact. Int J Occup Environ
Health 13 (2): 21321. doi:10.1179/oeh.2007.13.2.213.
PMC 3363002. PMID 17718179.
[56] Rana SV; Verma Y (2005). Biochemical toxicity of benzene. J Environ Biol 26 (2): 15768. PMID 16161967.
[59] OSHA
Hazard
Communication
Standard
1910.1200(d)(5)(ii), carcinogens under (d)(4) of
this section. Osha.gov. Retrieved on 2011-11-23.
[60] 10/16/2003 OSHA-recognized chemicals as carcinogens or potential carcinogens for Hazard Communication
purposes. Osha.gov (2003-10-16). Retrieved on 201010-09.
12
[64] Centers for Disease Control and Prevention (CDC), Atlanta, US (November 11, 2005). Cigarette Smoking
Among Adults United States, 2004. Morbidity and
Mortality Weekly Report 54 (44): 11211124. PMID
16280969.
[65] Public Health Statement. Benzene, Division of Toxicology and Environmental Medicine, August 2007
[66] FDA: Too Much Benzene In Some Drinks, CBS News,
May 19, 2006. Retrieved July 11, 2006.
[67] Drinking
Water
Contaminants|Organic
Chemicals|Benzene. Water.epa.gov. Retrieved on 2014-04-17.
[68] Chemical Sampling Information Benzene. Osha.gov. Retrieved on 2011-11-23.
[69] Benzene Toxicity: Standards and Regulations|ATSDR
Environmental Medicine & Environmental Health Education CSEM. Atsdr.cdc.gov (2000-06-30). Retrieved
on 2010-10-09.
[70] NIOSH respirator selection logic (October 2004). Cincinnati, OH: U.S. Department of Health and Human Services, Public Health Service, Centers for Disease Control,
National Institute for Occupational Safety and Health,
DHHS (NIOSH). Publication No. 2005-100.
[71] Documentation for Immediately Dangerous to Life or
Health Concentrations (IDLH): Introduction. Cdc.gov.
Retrieved on 2011-11-23.
[72] Public Health Statement for Benzene U.S. Department
of Health and Human Services, Public Health Service,
Centers for Disease Control, National Institute for Occupational Safety and Health. Atsdr.cdc.gov (2011-03-03).
Retrieved on 2011-11-23.
11
EXTERNAL LINKS
[80] ACGIH (2009). 2009 TLVs and BEIs. American Conference of Governmental Industrial Hygienists, Cincinnati,
Ohio.
[81] Baselt, R. (2008) Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster
City, CA, pp. 144148, ISBN 0962652377.
[82] Snyder, R; Hedli, C.C. (1996). An overview of benzene metabolism. Environ Health Perspect 104 (Suppl
6): 11651171. doi:10.1289/ehp.96104s61165. PMC
1469747. PMID 9118888.
[83] Dougherty, D; Garte, S; Barchowsky, A; Zmuda, J;
Taioli, E (2008). NQO1, MPO, CYP2E1, GSTT1 and
STM1 polymorphisms and biological eects of benzene
exposurea literature review. Toxicology Letters 182
(13): 717. doi:10.1016/j.toxlet.2008.09.008. PMID
18848868.
[84] Fracasso ME, Doria D, Bartolucci GB, Carrieri M,
Lovreglio P, Ballini A, Soleo L, Tranfo G, Manno M
(2010). Low air levels of benzene: Correlation between
biomarkers of exposure and genotoxic eects. Toxicol
Lett 192 (1): 228. doi:10.1016/j.toxlet.2009.04.028.
PMID 19427373.
[85] Eastmond, D.A.; Rupa, DS; Hasegawa, LS (2000). Detection of hyperdiploidy and chromosome breakage in interphase human lymphocytes following exposure to the
benzene metabolite hydroquinone using multicolor uorescence in situ hybridization with DNA probes. Mutat
Res 322 (1): 920. PMID 7517507.
[75] 01/10/1990 Use of Air-Purifying Respirators In Dangerous Concentrations of Gases Or Vapors. Osha.gov.
Retrieved on 2010-10-09.
[76] NIOSH/OSHA Interim Guidance for Protecting Deepwater Horizon Response Workers and Volunteers, Osha.gov
(2010-07-26)
11 External links
Benzene at The Periodic Table of Videos (University
of Nottingham)
International Chemical Safety Card 0015
USEPA Summary of Benzene Toxicity
NIOSH Pocket Guide to Chemical Hazards
CID 241 from PubChem
13
Dept. of Health and Human Services: TR-289:
Toxicology and Carcinogenesis Studies of Benzene
Video Podcast of Sir John Cadogan giving a lecture
on Benzene since Faraday, in 1991
Substance prole
Benzene in the ChemIDplus database
NLM Hazardous Substances Databank Benzene
14
12
12
12.1
Benzene Source: http://en.wikipedia.org/wiki/Benzene?oldid=636523427 Contributors: Paul Drye, Mav, Bryan Derksen, Tarquin, Ed
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Platonicmaria, Helpful Pixie Bot, HMSSolent, Bibcode Bot, Gauravjuvekar, Jayohen, Vagobot, Shawcity, Mark Arsten, Akileapen, ShishaTom, Deblovi, Guruleninn, Justincheng12345-bot, HatedHero, JesseAlanGordon, Scientic Alan 2, Qocheedy daiin, Xprofj, Ochemstudent21, Ssomme, Dexbot, Chrisvincent112, Pinto1978, Crispyrolls93, ComfyKem, Justin1207, Jackjayatherton, D Champagne28, Epicgenius, Chaosruiner, Frozenprakash, AmericanLemming, Jesper overgaard jensen, Dr.Jethwa, 1YlGC6dsynvm, CensoredScribe, Napy65,
Karu12345, Zenibus, Sararamiz, Anrnusna, S3HSIM, Argon borax, Monkbot, Paymoney, Ktlabe, JediChemist, Medgirl131, Maadhavan
Bhattacharjee, Sayamsethi, Andemosa, Y-S.Ko, Frederichgundogan and Anonymous: 560
12.2
Images
File:Benzen_acylowany.svg Source: http://upload.wikimedia.org/wikipedia/commons/8/8b/Benzen_acylowany.svg License: Public domain Contributors: Own work Original artist: Arrowsmaster
File:Benzene-xtal-3D-vdW.png Source: http://upload.wikimedia.org/wikipedia/commons/0/02/Benzene-xtal-3D-vdW.png License:
Public domain Contributors: Own work Original artist: Ben Mills
File:Benzene_Representations.svg Source: http://upload.wikimedia.org/wikipedia/commons/9/9a/Benzene_Representations.svg License: CC-BY-SA-3.0 Contributors: Own vector drawing based on layout of en:File:Benzol trans.png. Original artist: Vladsinger
File:Benzene_geometrie.svg Source: http://upload.wikimedia.org/wikipedia/commons/5/58/Benzene_geometrie.svg License: CC-BYSA-3.0 Contributors: Own work, d'aprs Benzen.svg Original artist: Haltopub
File:Benzol.JPG Source: http://upload.wikimedia.org/wikipedia/commons/8/8f/Benzol.JPG License: CC-BY-SA-3.0 Contributors:
Transferred from en.wikipedia
Original artist: de:benutzer:BDXX. Original uploader was DFS454 at en.wikipedia
File:Buckminsterfullerene-perspective-3D-balls.png
Source:
http://upload.wikimedia.org/wikipedia/commons/0/0f/
Buckminsterfullerene-perspective-3D-balls.png License: Public domain Contributors: ? Original artist: ?
12.3
Content license
15
12.3
Content license