Benzene

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Benzene (also known as benzol or [6]-annulene) is a Benzene
colorless, flammable, sweet-smelling liquid. It is a natural
constituent of crude oil (/entry/Petroleum) but is usually
synthesized from other compounds present in petroleum
(/entry/Petroleum). Chemically, it is classified as an aromatic
hydrocarbon (/entry/Hydrocarbon), which is a group of organic (/entry/File:Benzene_structure.png)
compounds (/entry/Organic_chemistry). Its chemical formula is
General
C (/entry/Carbon)6H (/entry/Hydrogen)6. If inhaled or ingested in
relatively large amounts, it can cause serious health problems, Systematic name Benzene
including cancer, and may even lead to premature death. On
Other names Benzol
the other hand, through years of patient effort, scientists have
found that it is a valuable solvent and an important precursor in Molecular formula
C6H6
the production of a wide range of materials, including drugs, (/entry/Chemical_formula)
plastics (/entry/Plastic), synthetic rubber (/entry/Rubber), and
c1ccccc1
dyes (/entry/Dye). SMILES
C1=CC=CC=C1

Contents History InChI=1/C6H6

InChI /c1-2-4-6-5-3-1/h1-
1 History Benzene has been the 6H
2 Structure subject of studies by
Molar mass (/entry/Molar_mass) 78.11 g/mol
3 Substituted benzene many famous scientists,
derivatives including Michael Faraday Appearance Colorless liquid
4 Production (/entry/Michael_Faraday)
CAS number [71-43-2]
4.1 Catalytic reforming and Linus Pauling
4.2 Toluene (/entry/Linus_Pauling). In Properties
hydrodealkylation
1825, Faraday reported
4.2.1 Toluene Density (/entry/Density) and
its isolation from oil gas 0.8786 g/cm, liquid
disproportionation phase
and gave it the name
4.3 Steam cracking bicarburet of hydrogen. In Solubility in water 1.79 g/L (25 C)
5 Uses 1833, Eilhard Mitscherlich
Melting point
produced it by the 5.5 C (278.6 K)
5.1 Early uses (/entry/Melting_point)
5.2 Current uses of distillation
benzene (/entry/Distillation) of Boiling point (/entry/Boiling_point) 80.1 C (353.2 K)

6 Reactions of benzene benzoic acid Viscosity (/entry/Viscosity) 0.652 cP at 20 C

7 Health effects (/entry/Benzoic_acid)
8 See also (from gum benzoin) and Structure
9 References lime (calcium oxide).
10 External links Molecular shape Planar
Mitscherlich named the
11 Credits
compound benzin. In Symmetry group D6h

1845, Charles Mansfield,

Dipole moment
working under August 0D
(/entry/Dipole#Molecular_dipoles)
Wilhelm von Hofmann, isolated benzene from coal tar. Four
years later, Mansfield began the first industrial-scale production Hazards

of benzene, based on the coal-tar method. MSDS External MSDS

Structure
Scientists who were familiar with the chemical formula of Flammable (F)
benzene (C6H6) were mystified about its molecular structure. Carc. Cat. 1
They knew that each molecule of benzene contained six carbon EU classification (/entry/Carcinogen)
atoms, but the substance did not behave as though each Muta. Cat. 2
molecule was an open-ended chain. Friedrich August Kekul Toxic (T)

von Stradonitz
(/entry/Friedrich_August_Kekul%C3%A9_von_Stradonitz) is 3
NFPA 704 2 0
usually credited with being the first to deduce the ring structure
of benzene, in 1865. It is reported that after he had spent a long (/entry/File:NFPA_704.sv
time mentally wrestling over the matter, he had a dream of a R45, R46, R11,
snake (/entry/Snake) swallowing its own tail. This image R-phrases R36/38,
inspired him to think of a ring structure for benzene. R48/23/24/25, R65

When Kekul made his formal claims, they were well-publicized S-phrases S53, S45
and accepted. It now appears that a lesser known scientist,
Flash point 11 C
Josef Loschmidt (1821-1895), had posited a cyclic structure for
benzene in a booklet published in 1861. Whether Kekul Autoignition temperature 561 C
actually had the dream or whether he borrowed from
RTECS number CY1400000
Loschmidt's publication are matters of debate. It is entirely
possible that the two scientists thought of benzene's ring Related compounds
structure independentlya type of occurrence that is not
Related cyclohexane
unusual in science. The cyclic nature of benzene was finally
hydrocarbons naphthalene
confirmed by the crystallographer Kathleen Lonsdale.
(/entry/Hydrocarbon) (/entry/Naphthalene)
Benzene presents a special problem in that, to account for all
toluene
the bonds, there must be alternating single and double covalent
Related compounds (/entry/Toluene)
bonds (/entry/Covalent_bond) between carbon atoms, which
borazine
may be represented as:
Except where noted otherwise, data are given for

materials in their standard state (at 25C, 100 kPa)

(/entry/File:Benz1.png)

Using the technique known as X-ray diffraction, researchers discovered that all the carbon-carbon (C-C) bonds in
benzene have the same length (140 picometers (pm)). The length of each C-C bond is greater than that of a double
bond (134 pm) but shorter than a single bond (147 pm). The bond length of 140 pm, which is intermediate in length, is
explained by the concept of "electron delocalization": the electrons for C-C bonding are distributed equally among the
six carbon atoms. (One representation is that the structure exists as a superposition of two "resonance structures,"
rather than either form individually.)

This delocalization of electrons is known as aromaticity (/entry/Aromaticity), which gives benzene great stability. This
enhanced stability is a fundamental property of a class of molecules called "aromatic molecules," differentiating them
from molecules that are not aromatic. To reflect the delocalized nature of the bonding, benzene is often depicted with
a circle inside a hexagonal arrangement of carbon atoms (which are not labeled):

(/entry/File:Benz4.png)

Substituted benzene derivatives

Many important chemicals are derived from benzene, wherein one or more hydrogen atoms are replaced with other
functional groups (/entry/Functional_group). Examples of simple benzene derivatives are phenol (/entry/Phenol)
(C6H5OH, or PhOH), toluene (/entry/Toluene) (C6H5CH3, or PhMe), and aniline (/entry/Aniline) ((C6H5NH2, or PhNH2).
The linking of two benzene rings gives biphenyl (C6H5-C6H5). When two or more aromatic rings are "fused" together,
(that is, when a side of one ring is shared with another), the resultant compounds are called fused aromatic
hydrocarbons, such naphthalene (/entry/Naphthalene) (with two fused rings) and anthracene (/entry/Anthracene) (with
three fused rings). The limit of the fusion process is the hydrogen-free material graphite (/entry/Graphite).

Some aromatic compounds are called heterocyclic. In these cases, one or more carbon atoms in the benzene ring
are replaced with other elements. The most important heterocyclic derivatives are rings containing nitrogen
(/entry/Nitrogen) atoms as well as carbon atoms. Examples of heterocyclic compounds are pyridine (/entry/Pyridine)
(C5H5N) and pyrimidine (/entry/Pyrimidine) (C4H4N2). (Two other heterocyclic compounds, pyridazine and pyrazine
have the same chemical formula as pyrimidine, but the relative positions of the two N atoms in each ring are
different.)

Production
Trace amounts of benzene may result whenever carbon (/entry/Carbon)-rich materials undergo incomplete
combustion (/entry/Combustion). It is produced in volcanoes (/entry/Volcano) and forest fires (/entry/Fire), and is also
a component of cigarette smoke.

Up until World War II (/entry/World_War_II), benzene was produced mainly as a byproduct of coke production in the
steel (/entry/Steel) industry. In the 1950s, however, as the demand for benzene increased, especially from the
growing plastics (/entry/Plastic) industry, necessitating its production from petroleum. Today, most benzene comes
from the petrochemical industry, with only a small fraction being produced from coal.

The industrial production of benzene relies on three major chemical processes: catalytic reforming, toluene
(/entry/Toluene) hydrodealkylation, and steam cracking. Another process, called toluene disproportionation, may be
used when the goal is to produce aromatics called xylenes (there are three types of xylenes) along with benzene.

Catalytic reforming
In catalytic reforming, a mixture of hydrocarbons (/entry/Hydrocarbon) with boiling points between 60-200 C is
blended with hydrogen (/entry/Hydrogen) gas, exposed to a catalyst (/entry/Catalyst) (such as platinum
(/entry/Platinum) chloride or rhenium (/entry/Rhenium) chloride), and heated at 500-525 C at pressures between 8
and 50 atmospheres (atm). Under these conditions, aliphatic hydrocarbons form rings and lose hydrogen to become
aromatic hydrocarbons. The aromatic products are extracted from the reaction mixture with any of a number of
solvents (/entry/Solvent), such as diethylene glycol or sulfolane, and benzene is separated from the other aromatics
by distillation.

Toluene hydrodealkylation
In the method known as toluene hydrodealkylation, toluene (/entry/Toluene) (C6H5CH3) is converted to benzene.
Toluene is mixed with hydrogen, then passed over a catalyst (of chromium (/entry/Chromium), molybdenum
(/entry/Molybdenum), or platinum (/entry/Platinum) oxide (/entry/Oxide)), at 500-600 C and 40-60 atm pressure.
Sometimes, higher temperatures are used instead of a catalyst. Under these conditions, toluene undergoes
dealkylation according to the chemical equation (/entry/Chemical_equation):

C6H5CH3 (/entry/Toluene) + H2 (/entry/Hydrogen) C6H6 + CH4 (/entry/Methane)

The typical reaction yield exceeds 95 percent. Sometimes, xylene (/entry/Xylene) and heavier aromatics are used in
place of toluene, with similar efficiency.

Toluene disproportionation
If benzene and xylenes are needed, then the method known as toluene disproportionation (TDP) may be an attractive
alternative. During the reaction, some toluene molecules lose their methyl groups to produce benzene molecules (as
above), while other toluene molecules gain methyl groups to produce xylene molecules (each of which has two
methyl groups).

Steam cracking
Steam cracking is the process for producing ethylene (/entry/Ethylene) and other olefins ("unsaturated hydrocarbons")
from aliphatic hydrocarbons (/entry/Hydrocarbon). Depending on the feedstock used to produce the olefins, steam
cracking can produce a benzene-rich liquid byproduct called pyrolysis gasoline. The latter may be blended with other
hydrocarbons as a gasoline additive, or distilled to separate it into its components, including benzene.

Uses
Early uses
In the nineteenth and early twentieth centuries, benzene was used as an after-shave lotion because of its pleasant
smell. In addition, prior to the 1920s, benzene was frequently used as an industrial solvent, especially for degreasing
metal. As its toxicity became obvious, benzene has been supplanted by other solvents.

In 1903, Lugwig Roselius popularized the use of benzene to decaffeinate coffee (/entry/Coffee). This discovery led to
the production of Sanka (-ka for kaffein). This process was later discontinued.

As a gasoline (/entry/Gasoline) additive, benzene increases the octane rating and reduces engine knock.
Consequently, before the 1950s, gasoline often contained several percent benzene. Thereafter, tetraethyl lead
replaced benzene 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 countries. In the United States (/entry/United_States), concern
over the negative health effects of benzene and the possibility of it entering groundwater (/entry/Groundwater) have
led to stringent regulations regarding the benzene content of gasolinethe values are now typically around one
percent. European petrol (gasoline) specifications now contain the same one percent limit on benzene content.

Current uses of benzene

Today, benzene is mainly used as an intermediate to make a variety of other chemicals.

The most widely produced derivatives of benzene include:

styrene, which is used to make polymers and plastics,

phenol (/entry/Phenol), for the production of resins and adhesives, and
cyclohexane, which is used in the manufacture of nylon (/entry/Nylon).

Smaller amounts of benzene are used to make some types of rubbers (/entry/Rubber), lubricants
(/entry/Lubricant), dyes (/entry/Dye), detergents, drugs (/entry/Drug), explosives (/entry/Explosive), and
pesticides (/entry/Pesticide).

In laboratory research, toluene (/entry/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.

Reactions of benzene
Benzene can participate in several types of reactions, some of which are given below.

(/entry/File:OChem-Mech-

ElectrophilicAromaticSubstitution-General.png)
 A general method of derivatizing benzene is known as "electrophilic aromatic substitution." The benzene ring
attracts cations, so that hydrogen atoms on the ring can be replaced by acyl or alkyl group to produce
substituted derivatives. A generalized reaction is shown on the right, where "Y+" is the cation form of the acyl or
alkyl group, and "B" is a base that eventually extracts H+ from the ring.

(/entry/File:Friedel-

Crafts_acylation_of_benzene_by_ethanol_chloride.png)

A method called Friedel-Crafts acylation is a specific example of electrophilic aromatic substitution. In this
reaction, an "acyl" group replaces a hydrogen atom on the benzene ring. The reaction is carried out in the
presence of a catalyst (/entry/Catalyst) such as aluminum chloride.

Likewise, in the
method called Friedel- (/entry/File:Friedel-craft-alk.png)
Crafts alkylation, an
"alkyl" group replaces
a hydrogen atom on the benzene ring (or other aromatic ring). The reaction is carried out with an alkyl halide
(/entry/Alkyl_halide) in the presence of a catalyst.

Nitration: When benzene is warmed with a combination of concentrated sulphuric and nitric acid, the reaction
produces nitrobenzene (C6H5NO2). This reaction, called nitration, is another example of "electrophilic aromatic
substitution." It involves the action of "nitronium" ions (NO2+).

Hydrogenation: Benzene and its derivatives can be converted to cyclohexane (C6H12) and its derivatives by
treatment with hydrogen at high pressures. The reaction, called hydrogenation, involves the addition of
hydrogen atoms to the aromatic ring.

Benzene is an excellent ligand in the organometallic (/entry/Complex_(chemistry)) chemistry of some metals.

Important examples include the sandwich complex, Cr(C6H6)2, and half-sandwich complex, [RuCl2(C6H6)]2.

Health effects
Benzene exposure has serious health effects. Breathing high levels of the substance can result in death
(/entry/Death), while low levels can cause drowsiness, dizziness, rapid heart rate, headaches, tremors, confusion,
and unconsciousness. Eating or drinking foods containing high levels of benzene can cause vomiting, stomach
irritation, dizziness, sleepiness, convulsions, rapid heart rate, and death.

The major effect of benzene from chronic (long-term) exposure is on the blood (/entry/Blood). Benzene damages the
bone marrow (/entry/Bone_marrow) and can cause a decrease in the production of red blood cells, leading to anemia
(/entry/Anemia). It can also cause excessive bleeding and may depress the immune system (/entry/Immune_system),
increasing the chances of infection (/entry/Infection).

It has been reported that some women who breathed high levels of benzene for many months had irregular menstrual
(/entry/Menstruation) periods and a decrease in the size of their ovaries. It is not known whether benzene exposure
affects the developing fetus (/entry/Fetus) in pregnant women or fertility in men.

Animal studies have shown low birth weights, delayed bone formation, and bone marrow damage when pregnant
animals breathed benzene.

The U.S. Department of Health and Human Services (DHHS) classifies benzene as a human carcinogen
(/entry/Carcinogen). Long-term exposure to high levels of benzene in the air can cause leukemia, a potentially fatal
cancer (/entry/Cancer) of the blood-forming organs. In particular, acute myeloid leukemia (AML) may be caused by
benzene.

There are several tests to indicate whether a person has been exposed to benzene. One of these is a breath test,
which must be done shortly after exposure. Another test measures benzene in the blood; but because benzene
disappears rapidly from the blood, measurements are accurate only for recent exposures.

Once benzene enters the digestive system, it is metabolized (/entry/Metabolism), and certain metabolites can be
measured in the urine. This test, like the others, must be done shortly after exposure. It is not a reliable indicator of
how much benzene a person has been exposed to, because the same metabolites in urine may be derived from other
sources.

The U.S. Environmental Protection Agency (EPA) has set the maximum permissible level of benzene in drinking water
at 0.005 milligrams per liter (0.005 mg/L). EPA requires that spills or accidental releases into the environment of 10
pounds (4.5 kg) or more of benzene should be reported to the agency.

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.

In March 2006, the official Food Standards Agency in Britain (/entry/United_Kingdom) conducted a survey of 150
brands of soft drinks. It found that four contained benzene at levels higher than the limits specified by the World
Health Organization. The affected batches were removed from sale.

In recent history, there have been many examples of the harmful health effects of benzene and its derivatives. For
instance, in 1981 in Madrid, people who had ingested benzene-contaminated olive oil suffered from toxic oil
syndrome, which caused localized immune suppression. In addition, chronic fatigue syndrome has been highly
correlated with people who eat "denatured" food that has been treated with solvents to remove fat, or food that
contains benzoic acid (/entry/Benzoic_acid).

Workers in various industries that make or use benzene may be at risk of exposure to high levels of this carcinogenic
chemical. Industries that involve the use of benzene include rubber (/entry/Rubber) manufacturers, oil refineries,
chemical plants, shoe manufacturers, and gasoline (/entry/Gasoline)-related industries. In 1987, OSHA estimated that
about 237,000 workers in the United States were potentially exposed to benzene, and it is not known if this number
has substantially changed since then.

Water and soil contamination are important pathways for the transmission of benzene. In the United States alone,
there are approximately 100,000 different sites that have benzene contamination in the soil or groundwater. In 2005,
after an explosion at the China National Petroleum Corporation (CNPC) factory in Jilin, China, benzene leaked into
the Songhua River. As the river supplies water to the city of Harbin, with a population of almost nine million, water
supply to the city was cut off.

See also
Organic chemistry (/entry/Organic_chemistry)
Solvent (/entry/Solvent)
Toluene (/entry/Toluene)

References
Couper, Archibald Scott. 1858. On a New Chemical Theory. Philosophical Magazine 16:104-116.
Lonsdale, Kathleen. 1929. The Structure of the Benzene Ring in Hexamethylbenzene. Proceedings of the Royal
Society 123A:494.
Lonsdale, Kathleen. An X-Ray Analysis of the Structure of Hexachlorobenzene, Using the Fourier Method.
Proceedings of the Royal Society 133A:536.
McMurry, John. 2004. Organic Chemistry. 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052
(http://www.amazon.com/dp/0534420052?tag=encyclopediap-
 20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0534420052&adid=0NQQZXQ96PDAJGB1J8XS).
Morrison, Robert T., and Robert N. Boyd. 1992. Organic Chemistry. 6th ed. Englewood Cliffs, NJ: Prentice Hall.
ISBN 0136436692 (http://www.amazon.com/dp/0136436692?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0136436692&adid=0NQQZXQ96PDAJGB1J8XS).
Solomons, T.W. Graham, and Fryhle, Craig B. 2004. Organic Chemistry. 8th ed. Hoboken, NJ: John Wiley. ISBN
0471417998 (http://www.amazon.com/dp/0471417998?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0471417998&adid=0NQQZXQ96PDAJGB1J8XS).
Associated Press. May 19, 2006. FDA: Too Much Benzene In Some Drinks.
(http://www.cbsnews.com/stories/2006/05/19/health/main1638170.shtml) CBS News. Retrieved August 17,
2007.

External links
All links retrieved June 9, 2016.

Benzene Material Safety Data Sheet (http://www.hazard.com/msds/f2/bqv/bqvjq.html)

NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/niosh/npg/npgd0049.html)
Dept. of Health and Human Services: TR-289: Toxicology and Carcinogenesis Studies of Benzene
(http://ntp.niehs.nih.gov/index.cfm?objectid=0707525C-0F07-05BF-A16CAC7B0ECC97B5)

Functional groups (/entry/Functional_group)

Chemical class: Alcohol (/entry/Alcohol) Aldehyde (/entry/Aldehyde) Alkane (/entry/Alkane) Alkene (/entry/Alkene) Alkyne
(/entry/Alkyne) Amide (/entry/Amide) Amine (/entry/Amine) Azo compound (/entry/Azo_compound) Benzene derivative
Carboxylic acid (/entry/Carboxylic_acid) Cyanate Ester (/entry/Ester) Ether (/entry/Ether) Haloalkane (/entry/Haloalkane)
Imine Isocyanide Isocyanate Ketone (/entry/Ketone) Nitrile (/entry/Nitrile) Nitro compound Nitroso compound Peroxide
Phosphoric acid (/entry/Phosphoric_acid) Pyridine derivative (/entry/Pyridine) Sulfone Sulfonic acid Sulfoxide Thioether
Thiol Toluene derivative (/entry/Toluene)

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