Benzene

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]

1.2 Ring formula

1
1.1

History

The empirical formula for benzene was long known,

but its highly polyunsaturated structure, with just one
hydrogen atom for each carbon atom, was challenging to
determine. Archibald Scott Couper in 1858 and Joseph
Loschmidt in 1861[21] suggested possible structures that
contained multiple double bonds or multiple rings, but too
little evidence was then available to help chemists decide
on any particular structure.

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]

In 1865, the German chemist Friedrich August Kekul

published a paper in French (for he was then teaching
in Francophone Belgium) suggesting that the structure
contained a six-membered ring of carbon atoms with alternating single and double bonds. The next year he
published a much longer paper in German on the same
subject.[22][23] Kekul used evidence that had accumulated in the intervening yearsnamely, that there always
appeared to be only one isomer of any monoderivative
of benzene, and that there always appeared to be exactly three isomers of every disubstituted derivative
now understood to correspond to the ortho, meta, and
para patterns of arene substitutionto argue in support
of his proposed structure.[24] Kekul's symmetrical ring
could explain these curious facts, as well as benzenes 1:1

Michael Faraday rst isolated and identied benzene in

1825 from the oily residue derived from the production
of illuminating gas, giving it the name bicarburet of hydrogen.[11][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 phne";[14] this is the root of the word phenol,
which is hydroxylated benzene, and phenyl, which is the
1

2
carbon-hydrogen ratio.[25]

Historic benzene formulae (from left to right) by Claus

(1867),[26] Dewar (1867),[27] Ladenburg (1869),[28] Armstrong
(1887),[29] Thiele (1899)[30] and Kekul (1865). Dewar benzene and prismane are dierent chemicals that have Dewars
and Ladenburgs structures. Thiele and Kekul's structures are
used today.

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

The various representations of benzene

X-ray diraction shows that all six carbon-carbon bonds

The cyclic nature of benzene was nally conrmed by the in benzene are of the same length, at 140 picometres
crystallographer Kathleen Lonsdale in 1929.[36][37]
(pm). The CC bond lengths are greater than a double bond (135 pm) but shorter than a single bond (147
pm). This intermediate distance is consistent with
1.3 Early applications
electron delocalization: the electrons for CC bonding
are distributed equally between each of the six carbon
In the 19th and early-20th centuries, benzene was used as atoms. Benzene has 8 hydrogen atoms fewer than the
an after-shave lotion because of its pleasant smell. Prior corresponding parent alkane, hexane. The molecule is
to the 1920s, benzene was frequently used as an indus- planar.[39] The MO description involves the formation
trial solvent, especially for degreasing metal. As its tox- of three delocalized orbitals spanning all six carbon
icity became obvious, benzene was supplanted by other atoms, while in VB theory the aromatic properties of
solvents, especially toluene (methyl benzene), which has benzene originate from spin coupling of all six orsimilar physical properties but is not as carcinogenic.
bitals.[40][41][42][43] It is likely that this stability contributes
In 1903, Ludwig Roselius popularized the use of benzene to the peculiar molecular and chemical properties known
to decaeinate coee. This discovery led to the produc- as aromaticity. To indicate the delocalized nature of the

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

Many important chemical compounds are derived from

benzene by replacing one or more of its hydrogen atoms
with another functional group. Examples of simple benzene derivatives are phenol, toluene, and aniline, abbreviated PhOH, PhMe, and PhNH2 , respectively. Linking
benzene rings gives biphenyl, C6 H5 C6 H5 . Further loss
of hydrogen gives fused aromatic hydrocarbons, such as
naphthalene and anthracene. The limit of the fusion process is the hydrogen-free allotrope of carbon, graphite.
In heterocycles, carbon atoms in the benzene ring are replaced with other elements. The most important derivatives are the rings containing nitrogen. Replacing one
CH with N gives the compound pyridine, C5 H5 N. Although benzene and pyridine are structurally related, benzene cannot be converted into pyridine. Replacement of a
second CH bond with N gives, depending on the location
of the second N, pyridazine, pyrimidine, and pyrazine.

Production

Four chemical processes contribute to industrial benzene

production: catalytic reforming, toluene hydrodealkylation, toluene disproportionation, and steam cracking. According to the ATSDR Toxicological Prole for benzene,
between 1978 and 1981, catalytic reformats accounted
for approximately 4450% of the total U.S benzene production.
Until World War II, most benzene was produced as
a by-product of coke production (or coke-oven light
oil) in the steel industry. However, in the 1950s, increased demand for benzene, especially from the growing
polymers industry, necessitated the production of benzene from petroleum. Today, most benzene comes from
the petrochemical industry, with only a small fraction be-

4.1 Catalytic reforming

In catalytic reforming, a mixture of hydrocarbons with
boiling points between 60200 C is blended with
hydrogen gas and then exposed to a bifunctional platinum
chloride or rhenium chloride catalyst at 500525 C and
pressures ranging from 850 atm. Under these conditions, aliphatic hydrocarbons form rings and lose hydrogen to become aromatic hydrocarbons. The aromatic
products of the reaction are then separated from the reaction mixture (or reformate) by extraction with any one
of a number of solvents, including diethylene glycol or
sulfolane, and benzene is then separated from the other
aromatics by distillation. The extraction step of aromatics
from the reformate is designed to produce aromatics with
lowest non-aromatic components. Recovery of the aromatics, commonly referred to as BTX (benzene, toluene
and xylene isomers), involves such extraction and distillation steps. There are a good many licensed processes
available for extraction of the aromatics.
In similar fashion to this catalytic reforming, UOP and
BP commercialized a method from LPG (mainly propane
and butane) to aromatics.

4.2 Toluene hydrodealkylation

Toluene hydrodealkylation converts toluene to benzene.
In this hydrogen-intensive process, toluene is mixed with
hydrogen, then passed over a chromium, molybdenum,
or platinum oxide catalyst at 500600 C and 4060 atm
pressure. Sometimes, higher temperatures are used instead of a catalyst (at the similar reaction condition). Under these conditions, toluene undergoes dealkylation to
benzene and methane:
C6 H5 CH3 + H2 C6 H6 + CH4
This irreversible reaction is accompanied by an equilibrium side reaction that produces biphenyl (aka diphenyl)
at higher temperature:
2C
6H
6H
2+C
6H
5C
6H
5
If the raw material stream contains much non-aromatic
components (parans or naphthenes), those are likely
decomposed to lower hydrocarbons such as methane,
which increases the consumption of hydrogen.

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

Where a chemical complex has similar demands for

both benzene and xylene, then toluene disproportionation
(TDP) may be an attractive alternative to the toluene hydrodealkylation. In the broad sense, 2 toluene molecules
are reacted and the methyl groups rearranged from one
toluene molecule to the other, yielding one benzene
molecule and one xylene molecule.
Given that demand for para-xylene (p-xylene) substantially exceeds demand for other xylene isomers, a renement of the TDP process called Selective TDP (STDP)
may be used. In this process, the xylene stream exiting
the TDP unit is approximately 90% paraxylene. In some
current catalytic systems, even the benzene-to-xylenes
ratio is decreased (more xylenes) when the demand of
xylenes is higher.

4.4

Steam cracking

Steam cracking is the process for producing ethylene and

other alkenes from aliphatic hydrocarbons. Depending
on the feedstock used to produce the olens, steam cracking can produce a benzene-rich liquid by-product called
pyrolysis gasoline. Pyrolysis gasoline can be blended
with other hydrocarbons as a gasoline additive, or routed
through an extraction process to recover BTX aromatics
(benzene, toluene and xylenes).

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

Currently, the production of and demand for benzene in

the Middle East register the greatest increases worldwide.
In laboratory research, toluene is now often used as a substitute for benzene. The solvent-properties of the two are
similar, but toluene is less toxic and has a wider liquid
range.
Major commodity chemicals and polymers derived from
benzene. Clicking on the image loads the appropriate
article

5.1 Component of gasoline

As a gasoline (petrol) additive, benzene increases the
octane rating and reduces knocking. As a consequence,
gasoline often contained several percent benzene before
the 1950s, when tetraethyl lead replaced it as the most
widely used antiknock additive. With the global phaseout of leaded gasoline, benzene has made a comeback as
a gasoline additive in some nations. In the United States,
concern over its negative health eects and the possibility of benzenes entering the groundwater have led to
stringent regulation of gasolines benzene content, with
limits typically around 1%.[46] European petrol specications now contain the same 1% limit on benzene content.
The United States Environmental Protection Agency introduced new regulations in 2011 that lowered the benzene content in gasoline to 0.62%.[47]

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.

Benzene is used mainly as an intermediate to make other

chemicals. About 80% of benzene is consumed in the
production of three chemicals, ethylbenzene, cumene,
and cyclohexane. Its most widely produced derivative is Electrophilic aromatic substitution of benzene
ethylbenzene, precursor to styrene, which is used to make
polymers and plastics. Cumene is converted phenol for
resins and adhesives. Cyclohexane is used in the manu- The most widely practiced example of this reaction is the
facture of Nylon. Smaller amounts of benzene are used to ethylation of benzene.

Approximately 24,700,000 tons were produced in

1999.[49] Highly instructive but of far less industrial
signicance is the Friedel-Crafts alkylation of benzene
(and many other aromatic rings) using an alkyl halide
in the presence of a strong Lewis acid catalyst. Similarly, the Friedel-Crafts acylation is a related example of
electrophilic aromatic substitution. The reaction involves
the acylation of benzene (or many other aromatic rings)
with an acyl chloride using a strong Lewis acid catalyst
such as aluminium chloride or Iron(III) chloride.
O
O
+
H3C

AlCl3

CH3

+ HCl

Cl

Friedel-Crafts acylation of benzene by acetyl chloride

A bottle of benzene. The warnings show benzene is a toxic and
ammable liquid.

6.1

Sulfonation, chlorination, nitration

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

Via hydrogenation, benzene and its derivatives convert to

cyclohexane and derivatives. This reaction is achieved
by the use of high pressures of hydrogen at high temperatures in the presence of a nely divided nickel, which
serves as a catalyst. In the absence of the catalyst, benzene is impervious to hydrogen. This reaction is practiced
on a very large scale industrially.

6.3

Metal complexes

Benzene is an excellent ligand in the organometallic

chemistry of low-valent metals. Important examples include the sandwich and half-sandwich complexes, respectively, Cr(C6 H6 )2 and [RuCl2 (C6 H6 )]2 .

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]

8.2 Exposure through smoking

Light refraction of benzene (above) and water (below)

See also : Benzene in soft drinks#Environmental

exposure to benzene
Vapors from products that contain benzene, such as glues,
paints, furniture wax, and detergents, can also be a source
of exposure, although many of these have been modied
or reformulated since the late 1970s to eliminate or reduce the benzene content. Air around hazardous waste
sites or gas stations may contain higher levels of benzene. Because petroleum hydrocarbon products are complex mixtures of chemicals, risk assessments for these

Exposure of the general population to benzene occurs

mainly through breathing, the major sources of benzene
being tobacco smoke (about 50%) as well as automobile service stations, exhaust from motor vehicles and industrial emissions (about 20% altogether). According to
the CDC, The mean number of cigarettes per day (cpd)
among daily smokers in 1993 was 19.6 (21.3 cpd for men
and 17.8 cpd for women) and in 2004 was 16.8 (18.1
cpd for men and 15.3 cpd for women).[64] According
to the August 2007 Public Health Statement, the average
smoker smokes 32 cpd, which in turn the average smoker
would take in about 1.8 milligrams (mg) of benzene per
day. This amount is about 10 times the average daily intake of benzene by nonsmokers.[65]

8.3 Exposure from soft drinks

In March 2006, the ocial Food Standards Agency in
Britain conducted a survey of 150 brands of soft drinks.
It found that four contained benzene levels above World
Health Organization limits. The aected batches were
removed from sale.[66] (See also benzene in soft drinks).

8.6

Exposure monitoring

8.4

Case examples

ing apparatus providing maximum worker protection

is permitted [NIOSH 2004[70] ].[71] In September 1995,
NIOSH issued a new policy for developing recommended
exposure limit (RELs) for substances, including carcinogens. 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 REL (10-hour) of 0.1 ppm.[72] The NIOSH
STEL (15 min) is 1 ppm.

Water and soil contamination are important pathways of

concern for transmission of benzene. In the US alone, approximately 100,000 sites have soil or groundwater contaminated with benzene.

In 2005, the water supply to the city of Harbin in China

with a population of almost nine million people, was cut
o because of a major benzene exposure. Benzene leaked
into the Songhua River, which supplies drinking water to American Conference of Governmental Industrial Hythe city, after an explosion at a China National Petroleum gienists (ACGIH) adopted Threshold Limit Values
Corporation (CNPC) factory in the city of Jilin on 13 (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.
November.

8.5

Benzene exposure limits

The United States Environmental Protection Agency has

set a maximum contaminant level (MCL) for benzene
in drinking water at 0.005 mg/L (5 ppb), as promulgated via the U.S. National Primary Drinking Water
Regulations.[67] This regulation is based on preventing
benzene leukemogenesis. The maximum contaminant
level goal (MCLG), a nonenforceable health goal that
would allow an adequate margin of safety for the prevention of adverse eects, is zero benzene concentration in
drinking water. The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or
more of benzene be reported.
The U.S. Occupational Safety and Health Administration
(OSHA) has set a permissible exposure limit of 1 part
of benzene per million parts of air (1 ppm) in the workplace during an 8-hour workday, 40-hour workweek. The
short term exposure limit for airborne benzene is 5 ppm
for 15 minutes.[68] These legal limits were based on studies demonstrating compelling evidence of health risk to
workers exposed to benzene. The risk from exposure
to 1 ppm for a working lifetime has been estimated as
5 excess leukemia deaths per 1,000 employees exposed.
(This estimate assumes no threshold for benzenes carcinogenic eects.) OSHA has also established an action
level of 0.5 ppm to encourage even lower exposures in the
workplace.[69]
The U.S. National Institute for Occupational Safety and
Health (NIOSH) revised the Immediately Dangerous to
Life and Health (IDLH) concentration for benzene to 500
ppm. The current NIOSH denition for an IDLH condition, as given in the NIOSH Respirator Selection Logic,
is one that poses a threat of exposure to airborne contaminants when that exposure is likely to cause death or immediate or delayed permanent adverse health eects or prevent escape from such an environment [NIOSH 2004].
The purpose of establishing an IDLH value is (1) to ensure that the worker can escape from a given contaminated environment in the event of failure of the respiratory protection equipment and (2) is considered a maximum level above which only a highly reliable breath-

8.6 Exposure monitoring

Airborne exposure monitoring for benzene must be conducted in order to properly assess personal exposures and
eectiveness of engineering controls. Initial exposure
monitoring should be conducted by an industrial hygienist or person specically trained and experienced in sampling techniques. Contact an AIHA Accredited Laboratory for advice on sampling methods.[73]
Each employer with a place of employment where occupational exposures to benzene occur shall monitor each
of these workplaces and work operations to determine accurately the airborne concentrations of benzene to which
employees may be exposed.[74] Representative 8-hour
TWA employee exposures need to be determined on the
basis of one sample or samples representing the full shift
exposure for each job classication in each work area.
Unless air samples are taken frequently, the employer
does not know the concentration and would not know how
much of a protection factor is needed.[75]
In providing consultation on work safety during oil cleanup operations following the Deepwater Horizon accident,
OSHA has worked with a number of other government
agencies to protect Gulf cleanup workers. OSHA partnered with the NIOSH to issue Interim Guidance for
Protecting Deepwater Horizon Response Workers and
Volunteers and recommend measures that should be
taken to protect workers from a variety of dierent health
hazards that these workers face.[76] OSHA conceded that
it recognizes that most of its PELs are outdated and inadequate measures of worker safety. In characterizing
worker exposure, OSHA instead relies on more up-todate recommended protective limits set by organizations
such as NIOSH, the ACGIH, and the American Industrial Hygiene Association (AIHA), and not on the older,
less protective PELS. Results of air monitoring are compared to the lowest known Occupational Exposure Limit
for the listed contaminant for purposes of risk assessment
and protective equipment recommendations.[77]

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

Even if it is not a common substrate for the metabolism

of organisms, benzene can be oxidized by both bacteria
and eukaryotes. In bacteria, dioxygenase enzyme can add
an oxygen molecule to the ring, and the unstable product
is immediately reduced (by NADH) to a cyclic diol with
two double bonds, breaking the aromaticity. Next, the
diol is newly reduced by NADH to catechol. The catechol is then metabolized to acetyl CoA and succinyl CoA,
used by organisms mainly in the Krebs Cycle for energy
production.
The pathway for the metabolism of benzene is complex
and begins in the liver. Several key enzymes are involved. These include cytochrome P450 2E1 (CYP2E1),
quinine oxidoreductase (NQ01), GSH, and myeloperoxidase (MPO). CYP2E1 is involved at multiple steps:
converting benzene to oxepin (benzene oxide), phenol
to hydroquinone, and hydroquinone to both benzenetriol
and catechol. Hydroquinone, benzenetriol and catechol
are converted to polyphenols. In the bone marrow, MPO
converts these polyphenols to benzoquinones. These intermediates and metabolites induce genotoxicity by multiple mechanisms including inhibition of topoisomerase
II (which maintains chromosome structure), disruption
of microtubules (which maintains cellular structure and
organization), generation of oxygen free radicals (unstable species) that may lead to point mutations, increasing oxidative stress, inducing DNA strand breaks, and
altering DNA methylation (which can aect gene expression). NQ01 and GSH shift metabolism away from toxicity. NQ01 metabolizes benzoquinone toward polyphenols (counteracting the eect of MPO). GSH is involved
with the formation of phenylmercapturic acid.[52][82]

EXPOSURE TO BENZENE

of function or gain of function. For example, mutations in

CYP2E1 increase activity and result in increased generation of toxic metabolites. NQ01 mutations result in loss
of function and may result in decreased detoxication.
Myeloperoxidase mutations result in loss of function and
may result in decreased generation of toxic metabolites.
GSH mutations or deletions result in loss of function and
result in decreased detoxication. These genes may be
targets for genetic screening for susceptibility to benzene
toxicity.[83]

8.9 Molecular toxicology

The paradigm of toxicological assessment of benzene is
shifting towards the domain of molecular toxicology as
it allows understanding of fundamental biological mechanisms in a better way. Glutathione seems to play an important role by protecting against benzene-induced DNA
breaks and it is being identied as a new biomarker for exposure and eect.[84] Benzene causes chromosomal aberrations in the peripheral blood leukocytes and bone marrow explaining the higher incidence of leukemia and multiple myeloma caused by chronic exposure. These aberrations can be monitored using uorescent in situ hybridization (FISH) with DNA probes to assess the effects of benzene along with the hematological tests as
markers of hematotoxicity.[85] Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may inuence
susceptibility to the toxic eects of benzene exposure.
Individuals carrying variant of NAD(P)H:quinone oxidoreductase 1 (NQO1), microsomal epoxide hydrolase
(EPHX) and deletion of the glutathione S-transferase T1
(GSTT1) showed a greater frequency of DNA singlestranded breaks.[86]

8.10 Biological oxidation and carcinogenic

activity
One way of understanding the carcinogenic eects of
benzene is by examining the products of biological oxidation. Pure benzene, for example, oxidizes in the body to
produce an epoxide, benzene oxide, which is not excreted
readily and can interact with DNA to produce harmful
mutations.

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

Benzene in soft drinks

BTEX
Benzene in Kekul's article

10

[5] http://chemister.ru/Database/properties-en.php?dbid=
1&id=644
[6] Seidell, Atherton; Linke, William F. (1952). [Google
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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

Industrial Union Department v.

Petroleum Institute

[4] Coker, A. Kayode; Ludwig, Ernest E. (2007). Ludwigs

Applied Process Design for Chemical And Petrochemical
Plants 1. Elsevier. p. 114. ISBN 0-7506-7766-X. Retrieved 2012-05-31.

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[11] Faraday, M. (1825). On new compounds of carbon

and hydrogen, and on certain other products obtained
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443450, Faraday discusses bicarburet of hydrogen
(benzene). On pages 449450, he shows that benzenes
empirical formula is C6 H6 , although he doesn't realize
it because he (like most chemists at that time) used the
wrong atomic mass for carbon (6 instead of 12).
[12] Kaiser, R. (1968). Bicarburet of Hydrogen. Reappraisal of the Discovery of Benzene in 1825 with the
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[13] Mitscherlich, E. (1834). "ber das Benzol und die Suren
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types of acids)". Annalen der Pharmacie 9 (1): 3948.
doi:10.1002/jlac.18340090103. In a footnote on page 43,
Liebig, the journals editor, suggested changing Mitscherlichs original name for benzene (namely, benzin) to
benzol, because the sux "-in suggested that it was
an alkaloid (e.g., Chinin (quinine)), which benzene isn't,
whereas the sux "-ol suggested that it was oily, which
benzene is. Thus on page 44, Mitscherlich states: Da
diese Flssigkeit aus der Benzosure gewonnen wird, und
wahrscheinlich mit den Benzoylverbindungen im Zusammenhang steht, so gibt man ihr am besten den Namen Benzol, da der Name Benzon schon fr die mit dem Bittermandell isomerische Verbindung von Liebig und Whler
gewhlt worden ist. (Since this liquid [benzene] is obtained from benzoic acid and probably is related to benzoyl compounds, the best name for it is benzol, since

10

10

the name benzon has already been chosen, by Liebig

and Whler, for the compound thats isomeric with the oil
of bitter almonds [benzaldehyde].)
[14] Laurent, Auguste (1836) Sur la chlorophnise et les
acides chlorophnisique et chlorophnsique, Annales de
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prcdens (, j'claire), puisque la benzine se trouve
dans le gaz de l'clairage. (I give the name of phne
(, I illuminate) to the fundamental radical of the
preceding acid, because benzene is found in illuminating
gas.)
[15] Kekul, August (1872). Ueber einige Condensationsproducte des Aldehyds. Liebigs Ann. Chem. 162 (1): 77
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[16] Hofmann, A. W. (1845) Ueber eine sichere Reaction
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[17] Manseld, Charles Blachford (1849) Untersuchung des
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[18] Charles Manseld led for (November 11, 1847) and received (May 1848) a patent (no. 11,960) for the fractional
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On insolinic
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empirical formulas of organic compounds that appear in
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[22] Kekul, F. A. (1865). Sur la constitution des substances
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atoms of benzene could form a chane ferme (a closed
chain, a loop).
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clockwise or counterclockwise; however, no such isomers
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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

TEXT AND IMAGE SOURCES, CONTRIBUTORS, AND LICENSES

Text and image sources, contributors, and licenses

Text

Benzene Source: http://en.wikipedia.org/wiki/Benzene?oldid=636523427 Contributors: Paul Drye, Mav, Bryan Derksen, Tarquin, Ed
Poor, RK, XJaM, Fcueto, Arvindn, William Avery, SimonP, Ktsquare, DrBob, Heron, Montrealais, Ewen, Pit, Fred Bauder, Dominus,
Shyamal, Shellreef, Kku, Cyde, Alo, Shimmin, Julesd, EdH, MichaK, Timwi, Stone, Dysprosia, Wik, Taxman, Paul-L, Sabbut, Jeeves,
Ortonmc, Jeq, Mjmcb1, Northgrove, Chuunen Baka, Gentgeen, Nufy8, Robbot, Peak, Sverdrup, Bkell, Mervyn, Hadal, Zxmaster, Isopropyl, ElBenevolente, Giftlite, DocWatson42, Timpo, Iridium77, Subsolar, Dratman, Bensaccount, Unconcerned, Tom-, Eequor, Solipsist,
Bobblewik, Kandar, Wmahan, Antandrus, Onco p53, Chiu frederick, Andux, DragonySixtyseven, H Padleckas, Atemperman, TreyHarris,
Nickptar, Edsanville, Grunt, Guppynsoup, Spiy sperry, Rich Farmbrough, Guanabot, Cacycle, Michall, Wk muriithi, Exabyte, ESkog,
Martinman11, Zaslav, Joanjoc, Hayabusa future, Root4(one), ~K, Mdhowe, Davidruben, R. S. Shaw, La goutte de pluie, Kjkolb, Rje,
Egonw, HasharBot, Dtsang, SemperBlotto, Craigy144, Benjah-bmm27, ABCD, Walkerma, Snowolf, Shinjiman, Ayeroxor, Wimvandorst,
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12.2

Images

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12.3

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12.3

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