関: benzole、C6H6

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a colorless liquid hydrocarbon; highly inflammable; carcinogenic; the simplest of the aromatic compounds (同)benzine, benzol

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/05 06:52:57」(JST)

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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, comprising a few percent of its mass. Most non-industrial applications have been limited by benzene's carcinogenicity.

1 History
- 1.1 Discovery
- 1.2 Ring formula
- 1.3 Early applications
2 Structure
3 Benzene derivatives
4 Production
- 4.1 Catalytic reforming
- 4.2 Toluene hydrodealkylation
- 4.3 Toluene disproportionation
- 4.4 Steam cracking
- 4.5 Other sources
5 Uses
- 5.1 Component of gasoline
6 Reactions
- 6.1 Sulfonation, chlorination, nitration
- 6.2 Hydrogenation
- 6.3 Metal complexes
7 Health effects
8 Exposure to benzene
- 8.1 Inhalation
- 8.2 Exposure through smoking
- 8.3 Exposure from soft drinks
- 8.4 Case examples
- 8.5 Benzene exposure limits
- 8.6 Exposure monitoring
- 8.7 Biomarkers of exposure
- 8.8 Biotransformations
- 8.9 Molecular toxicology
- 8.10 Biological oxidation and carcinogenic activity
- 8.11 Summary
9 See also
10 References
11 External links

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 "flowers of benzoin", or benzoic acid. The hydrocarbon derived from benzoic acid thus acquired the name benzin, benzol, or benzene.^[10]

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.^[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 "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.

Historic benzene formulae as proposed by Kekulé.^[15]

In 1845, Charles Mansfield, working under August Wilhelm von Hofmann, isolated benzene from coal tar.^[16] Four years later, Mansfield began the first industrial-scale 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]

Ring formula

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.

In 1865, the German chemist Friedrich August Kekulé 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] Kekulé used evidence that had accumulated in the intervening years—namely, 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 substitution—to argue in support of his proposed structure.^[24] Kekulé's symmetrical ring could explain these curious facts, as well as benzene's 1:1 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 Kekulé (1865). Dewar benzene and prismane are different chemicals that have Dewar's and Ladenburg's structures. Thiele and Kekulé'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 Kekulé's honor, celebrating the twenty-fifth anniversary of his first benzene paper. Here Kekulé 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 Kekulé'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 Kekulé'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.^{[citation needed]}) Kekulé'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]

The cyclic nature of benzene was finally confirmed by the crystallographer Kathleen Lonsdale in 1929.^[36]^[37]

Early applications

In the 19th and early-20th centuries, benzene was used as an after-shave lotion because of its pleasant smell. Prior to the 1920s, benzene was frequently used as an industrial solvent, especially for degreasing metal. As its toxicity became obvious, benzene was supplanted by other solvents, especially toluene (methyl benzene), which has similar physical properties but is not as carcinogenic.

In 1903, Ludwig Roselius popularized the use of benzene to decaffeinate coffee. This discovery led to the production of Sanka. This process was later discontinued. Benzene was historically used as a significant 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 significant contaminant until the late 1970s when leukemia deaths were found associated with Goodyear's Pliofilm 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.

Structure

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]

The various representations of benzene

X-ray diffraction shows that all six carbon-carbon bonds in benzene are of the same length, at 140 picometres (pm). The C–C bond lengths are greater than a double bond, (135 pm), but shorter than a single bond, (147 pm). This intermediate distance is consistent with electron delocalization: the electrons for C–C bonding are distributed equally between each of the six carbon atoms. Benzene has 8 hydrogen atoms fewer than the corresponding parent alkane, hexane. The molecule is planar.^[39] The MO description involves the formation of three delocalized π orbitals spanning all six carbon atoms, while in VB theory the aromatic properties of benzene originate from spin coupling of all six π orbitals.^[40]^[41]^[42]^[43] It is likely that this stability contributes to the peculiar molecular and chemical properties known as aromaticity. To indicate the delocalized nature of the bonding, benzene is often depicted with a circle inside a 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 sufficiently 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

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, C₆H₅–C₆H₅. 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, C₅H₅N. 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 Profile for benzene, between 1978 and 1981, catalytic reformats accounted for approximately 44–50% 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 being produced from coal.

Catalytic reforming

In catalytic reforming, a mixture of hydrocarbons with boiling points between 60–200 °C is blended with hydrogen gas and then exposed to a bifunctional platinum chloride or rhenium chloride catalyst at 500–525 °C and pressures ranging from 8–50 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.

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 500–600 °C and 40–60 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:

C₆H₅CH₃ + H₂ → C₆H₆ + CH₄

This irreversible reaction is accompanied by an equilibrium side reaction that produces biphenyl (aka diphenyl) at higher temperature:

2 C
6H
6 H
2 + C
6H
5–C
6H
5

If the raw material stream contains much non-aromatic components (paraffins or naphthenes), those are likely decomposed to lower hydrocarbons such as methane, which increases the consumption of hydrogen.

A typical reaction yield exceeds 95%. Sometimes, xylenes and heavier aromatics are used in place of toluene, with similar efficiency.

This is often called "on-purpose" methodology to produce benzene, compared to conventional BTX (benzene-toluene-xylene) extraction processes.

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 refinement 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.

Steam cracking

Steam cracking is the process for producing ethylene and other alkenes from aliphatic hydrocarbons. Depending on the feedstock used to produce the olefins, 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).

Other sources

Trace amounts of benzene may result whenever carbon-rich materials undergo incomplete combustion. It is produced in volcanoes and forest fires, and is also a component of cigarette smoke. Benzene is a principal product from the combustion of PVC (polyvinyl chloride).

Uses

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 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 manufacture of Nylon. Smaller amounts of benzene are used to make some types of rubbers, lubricants, dyes, detergents, drugs, explosives, and pesticides.

In both the US and Europe, 50% of benzene is used in the production of ethylbenzene/styrene, 20% is used in the production of cumene, and about 15% of benzene is used in the production of cyclohexane (eventually to nylon).^{[citation needed]}

Currently, the production of and demand for benzene in the Middle East register the greatest increases worldwide. It will probably see its share of the global supply and demand expand by 3.7 and 3.3 percentage points, respectively, until 2018. However, the Asia-Pacific region will continue to dominate the market and account for almost half of the global demand.^[46]

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

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 effects and the possibility of benzene's entering the groundwater have led to stringent regulation of gasoline's benzene content, with limits typically around 1%.^[47] European petrol specifications 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%.^[48]

Reactions

The most common reactions of benzene involve substitution of a proton by other groups.^[49] Electrophilic aromatic substitution is a general method of derivatizing benzene. Benzene is sufficiently nucleophilic that it undergoes substitution by acylium ions and alkyl carbocations to give substituted derivatives.

Electrophilic aromatic substitution of benzene

The most widely practiced example of this reaction is the ethylation of benzene.

Approximately 24,700,000 tons were produced in 1999.^[50] Highly instructive but of far less industrial significance 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.

Friedel-Crafts acylation of benzene by acetyl chloride

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 in achieved with chlorine to give chlorobenzene in the presence of a catalyst such as aluminium trichloride.

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 finely 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.

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(C₆H₆)₂ and [RuCl₂(C₆H₆)]₂.

Health effects

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

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.^[51]^[52] The specific 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).^[53]

The American Petroleum Institute (API) stated in 1948 that "it is generally considered that the only absolutely safe concentration for benzene is zero."^[54] The US Department of Health and Human Services (DHHS) classifies 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.^[55] IARC rated benzene as "known to be carcinogenic to humans" (Group 1).

Human exposure to benzene is a global health problem.^[vague] 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 sexes of multiple species of laboratory animals exposed via various routes.^[56]^[57]

Some women who inhaled high levels of benzene for many months had irregular menstrual periods and a decrease in the size of their ovaries. Benzene exposure has been linked directly to the neural birth defects spina bifida and anencephaly.^[58] Men exposed to high levels of benzene are more likely to have an abnormal amount of chromosomes in their sperm, which impacts fertility and fetal development.^[59]

Exposure to benzene

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 modified 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 products, in general, focus on specific toxic constituents. The petroleum constituents of primary interest to human health have been the aromatic hydrocarbons (i.e., benzene, ethylbenzene, toluene, and xylenes). In the U.S., OSHA requires that a mixture "shall be assumed to present a carcinogenic hazard if it contains a component in concentrations of 0.1% or greater, which is considered to be a carcinogen.^[60]^[61]

Outdoor air may contain low levels of benzene from automobile service stations, wood smoke, tobacco smoke, the transfer of gasoline, exhaust from motor vehicles, and industrial emissions.^[62] About 50% of the entire nationwide (United States) exposure to benzene results from smoking tobacco or from exposure to tobacco smoke.^[63]

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 five 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.^[64]

Exposure through smoking

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)."^[65] 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.^[66]

Exposure from soft drinks

In March 2006, the official 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 affected batches were removed from sale.^[67] (See also benzene in soft drinks).

Case examples

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.^{[citation needed]}

In 2005, the water supply to the city of Harbin in China with a population of almost nine million people, was cut off because of a major benzene exposure. Benzene leaked into the Songhua River, which supplies drinking water to the city, after an explosion at a China National Petroleum Corporation (CNPC) factory in the city of Jilin on 13 November.^{[citation needed]}

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.^[68] 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 effects, 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.^[69] 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 benzene's carcinogenic effects.) OSHA has also established an action level of 0.5 ppm to encourage even lower exposures in the workplace.^[70]

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 definition 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 effects 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 breathing apparatus providing maximum worker protection is permitted [NIOSH 2004^[71]].^[72] 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.^[73] The NIOSH STEL (15 min) is 1 ppm.

American Conference of Governmental Industrial Hygienists (ACGIH) adopted Threshold Limit Values (TLVs) for benzene at 0.5 ppm TWA and 2.5 ppm STEL.

Exposure monitoring

Airborne exposure monitoring for benzene must be conducted in order to properly assess personal exposures and effectiveness of engineering controls. Initial exposure monitoring should be conducted by an industrial hygienist or person specifically trained and experienced in sampling techniques. Contact an AIHA Accredited Laboratory for advice on sampling methods.^[74]

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.^[75] 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 classification 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.^[76]

In providing consultation on work safety during oil clean-up 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 different health hazards that these workers face.^[77] 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-to-date 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.^[78]

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 first 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 μg/g creatinine for muconic acid and 25 μg/g creatinine for phenylmercapturic acid in an end-of-shift urine specimen.^[79]^[80]^[81]^[82]

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 affect gene expression). NQ01 and GSH shift metabolism away from toxicity. NQ01 metabolizes benzoquinone toward polyphenols (counteracting the effect of MPO). GSH is involved with the formation of phenylmercapturic acid.^[53]^[83]

Genetic polymorphisms in these enzymes may induce loss 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 detoxification. 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 detoxification. These genes may be targets for genetic screening for susceptibility to benzene toxicity.^[84]

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 identified as a new biomarker for exposure and effect.^[85] 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 fluorescent in situ hybridization (FISH) with DNA probes to assess the effects of benzene along with the hematological tests as markers of hematotoxicity.^[86] Benzene metabolism involves enzymes coded for by polymorphic genes. Studies have shown that genotype at these loci may influence susceptibility to the toxic effects 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 single-stranded breaks.^[87]

Biological oxidation and carcinogenic activity

One way of understanding the carcinogenic effects 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.

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 fires, synthesis of chemicals such as phenol, production of synthetic fibers, and fabrication of rubbers, lubricants, pesticides, medications, and dyes. The major sources 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 by-products called metabolites.^[88]

OSHA regulates levels of benzene in the workplace.^[89] 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.^[90]

References

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^ Arnold, D.; Plank, C.; Erickson, E.; Pike, F. (1958). "Solubility of Benzene in Water". Industrial & Engineering Chemistry Chemical & Engineering Data Series 3 (2): 253. doi:10.1021/i460004a016.
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^ 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 Scribner's Sons. p. 101. ISBN 0684181959.
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^ Faraday, M. (1825). "On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat". Philosophical Transactions of the Royal Society 115: 440–466. doi:10.1098/rstl.1825.0022. JSTOR 107752. On pages 443–450, Faraday discusses "bicarburet of hydrogen" (benzene). On pages 449–450, he shows that benzene's empirical formula is C₆H₆, 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).
^ Kaiser, R. (1968). "Bicarburet of Hydrogen. Reappraisal of the Discovery of Benzene in 1825 with the Analytical Methods of 1968". Angewandte Chemie International Edition in English 7 (5): 345–350. doi:10.1002/anie.196803451.
^ Mitscherlich, E. (1834). "Über das Benzol und die Säuren der Oel- und Talgarten (On benzol and oily and fatty types of acids)". Annalen der Pharmacie 9 (1): 39–48. doi:10.1002/jlac.18340090103. In a footnote on page 43, Liebig, the journal's editor, suggested changing Mitscherlich's original name for benzene (namely, "benzin") to "benzol", because the suffix "-in" suggested that it was an alkaloid (e.g., Chinin (quinine)), which benzene isn't, whereas the suffix "-ol" suggested that it was oily, which benzene is. Thus on page 44, Mitscherlich states: "Da diese Flüssigkeit aus der Benzoësäure gewonnen wird, und wahrscheinlich mit den Benzoylverbindungen im Zusammenhang steht, so gibt man ihr am besten den Namen Benzol, da der Name Benzoïn schon für die mit dem Bittermandelöl isomerische Verbindung von Liebig und Wöhler gewählt 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 the name "benzoïn" has already been chosen, by Liebig and Wöhler, for the compound that's isomeric with the oil of bitter almonds [benzaldehyde].)
^ Laurent, Auguste (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique," Annales de Chemie et de Physique, vol. 63, pp. 27–45, see p. 44: "Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage." (I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acid, because benzene is found in illuminating gas.)
^ Kekulé, August (1872). "Ueber einige Condensationsproducte des Aldehyds". Liebigs Ann. Chem. 162 (1): 77–124. doi:10.1002/jlac.18721620110.
^ Hofmann, A. W. (1845) "Ueber eine sichere Reaction auf Benzol" (On a reliable test for benzene), Annalen der Chemie und Pharmacie, vol. 55, pp. 200–205; on pp. 204–205, Hofmann found benzene in coal tar oil.
^ Mansfield, Charles Blachford (1849) "Untersuchung des Steinkohlentheers" (Investigation of coal tar), Annalen der Chemie und Pharmacie, vol. 69, pp. 162–180.
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^ Cernicharo, José et al. (1997), "Infrared Space Observatory's Discovery of C₄H₂, C₆H₂, and Benzene in CRL 618", Astrophysical Journal Letters 546 (2): L123–L126, Bibcode:2001ApJ...546L.123C, doi:10.1086/318871
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External links

Wikimedia Commons has media related to Benzene.

Look up benzene in Wiktionary, the free dictionary.

Benzene at The Periodic Table of Videos (University of Nottingham)
Benzene (www.eco-usa.net)
International Chemical Safety Card 0015
USEPA Summary of Benzene Toxicity
NIOSH Pocket Guide to Chemical Hazards
CID 241 from PubChem
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 profile
Benzene in the ChemIDplus database
NLM Hazardous Substances Databank – Benzene

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Related Pictures

★リンクテーブル★

リンク元	「ベンゼン」「benzole」
拡張検索	「p-dimethylaminoazobenzene」「p-chloronitrobenzene」「hexachlorobenzene」「hydroxybenzene」

「ベンゼン」

Benzene
	IUPAC name Benzene
	Systematic name Cyclohexa-1,3,5-triene
	Other names 1,3,5-Cyclohexatriene, Benzol, Phene
Identifiers
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
	SMILES c1ccccc1 ;
	InChI InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H ; Key: UHOVQNZJYSORNB-UHFFFAOYSA-N InChI=1/C6H6/c1-2-4-6-5-3-1/h1-6H; Key: UHOVQNZJYSORNB-UHFFFAOYAH ;
Properties
Molecular formula	C6H6
Molar mass	78.11 g mol−1
Appearance	Colorless liquid
Odor	Aromatic, gasoline-like
Density	0.8765(20) g/cm3
Melting point	5.53 °C (41.95 °F; 278.68 K)
Boiling point	80.1 °C (176.2 °F; 353.2 K)
Solubility in water	1.53 g/L (0 °C); 1.81 g/L (9 °C); 1.79 g/L (15 °C); 1.84 g/L (30 °C); 2.26 g/L (61 °C); 3.94 g/L (100 °C); 21.7 g/kg (200 °C, 6.5 MPa); 17.8 g/kg (200 °C, 40 MPa)
Solubility	Soluble in alcohol, CHCl3, CCl4, diethyl ether, acetone, acetic acid
Solubility in ethanediol	5.83 g/100 g (20 °C); 6.61 g/100 g (40 °C); 7.61 g/100 g (60 °C)
Solubility in ethanol	20 °C, solution in water:; 1.2 mL/L (20% v/v)
Solubility in acetone	20 °C, solution in water:; 7.69 mL/L (38.46% v/v); 49.4 mL/L (62.5% v/v)
Solubility in diethylene glycol	52 g/100 g (20 °C)
log P	2.13
Vapor pressure	12.7 kPa (25 °C); 24.4 kPa (40 °C); 181 kPa (100 °C)
λmax	255 nm
Magnetic susceptibility	54.8·10−6 cm3/mol
Refractive index (nD)	1.5011 (20 °C); 1.4948 (30 °C)
Viscosity	0.7528 cP (10 °C); 0.6076 cP (25 °C); 0.4965 cP (40 °C); 0.3075 cP (80 °C)
Structure
Molecular shape	Tetrahedral
Dipole moment	0 D
Thermochemistry
Specific; heat capacity C	134.8 J/mol·K
Std molar; entropy So298	173.26 J/mol·K
Std enthalpy of; formation ΔfHo298	48.7 kJ/mol
Std enthalpy of; combustion ΔcHo298	3267.6 kJ/mol
Hazards
MSDS	External MSDS
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H225, H304, H315, H319, H340, H350, H372
GHS precautionary statements	P201, P210, P301+310, P305+351+338, P308+313, P331
EU classification	F T; Carc. Cat. 1; Muta. Cat. 2
R-phrases	R45, R46, R11, R16, R36/38,R48/23/24/25, R65
S-phrases	S53, S45
NFPA 704	3 2 0
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%
LD50	930 mg/kg (rat, oral)
Related compounds
Related compounds	Toluene; Borazine
Supplementary data page
Structure and; properties	n, εr, etc.
Thermodynamic; data	Phase behaviour; Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: benzene
同: ベンゾール benzol
関

臨床関連

ベンゼン中毒

法令

特定化学物質等障害予防規則

「benzole」

　　[★]

ベンゾール

関: benzene

「p-dimethylaminoazobenzene」

　　[★]

p-ジメチルアミノアゾベンゼン、パラジメチルアミノアゾベンゼン

「p-chloronitrobenzene」

　　[★] パラクロロニトロベンゼン

「hexachlorobenzene」

　　[★]

ヘキサクロロベンゼン

「hydroxybenzene」

　　[★] ヒドロキシベンゼン

[handbook13-1] Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.

[2] Arnold, D.; Plank, C.; Erickson, E.; Pike, F. (1958). "Solubility of Benzene in Water". Industrial & Engineering Chemistry Chemical & Engineering Data Series 3 (2): 253. doi:10.1021/i460004a016.

[3] Breslow, R.; Guo, T. (1990). "Surface tension measurements show that chaotropic salting-in denaturants are not just water-structure breakers". Proceedings of the National Academy of Sciences of the United States of America 87 (1): 167–9. Bibcode:1990PNAS...87..167B. doi:10.1073/pnas.87.1.167. PMC 53221. PMID 2153285.

[4] Coker, A. Kayode; Ludwig, Ernest E. (2007). Ludwig's Applied Process Design for Chemical And Petrochemical Plants 1. Elsevier. p. 114. ISBN 0-7506-7766-X. Retrieved 2012-05-31.

[chemister-5] ttp://chemister.ru/Database/properties-en.php?dbid=1&id=644

[sioc-6] Seidell, Atherton; Linke, William F. (1952). [Google Books Solubilities of Inorganic and Organic Compounds]. Van Nostrand. Retrieved 2014-05-29.

[nist-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)

[sigma-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 Scribner's Sons. p. 101. ISBN 0684181959.

[rocke-10] Rocke, A. J. (1985). "Hypothesis and Experiment in the Early Development of Kekule's Benzene Theory". Annals of Science 42 (4): 355–81. doi:10.1080/00033798500200411.

[11] Faraday, M. (1825). "On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat". Philosophical Transactions of the Royal Society 115: 440–466. doi:10.1098/rstl.1825.0022. JSTOR 107752. On pages 443–450, Faraday discusses "bicarburet of hydrogen" (benzene). On pages 449–450, he shows that benzene's empirical formula is C₆H₆, 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 Analytical Methods of 1968". Angewandte Chemie International Edition in English 7 (5): 345–350. doi:10.1002/anie.196803451.

[13] Mitscherlich, E. (1834). "Über das Benzol und die Säuren der Oel- und Talgarten (On benzol and oily and fatty types of acids)". Annalen der Pharmacie 9 (1): 39–48. doi:10.1002/jlac.18340090103. In a footnote on page 43, Liebig, the journal's editor, suggested changing Mitscherlich's original name for benzene (namely, "benzin") to "benzol", because the suffix "-in" suggested that it was an alkaloid (e.g., Chinin (quinine)), which benzene isn't, whereas the suffix "-ol" suggested that it was oily, which benzene is. Thus on page 44, Mitscherlich states: "Da diese Flüssigkeit aus der Benzoësäure gewonnen wird, und wahrscheinlich mit den Benzoylverbindungen im Zusammenhang steht, so gibt man ihr am besten den Namen Benzol, da der Name Benzoïn schon für die mit dem Bittermandelöl isomerische Verbindung von Liebig und Wöhler gewählt 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 the name "benzoïn" has already been chosen, by Liebig and Wöhler, for the compound that's isomeric with the oil of bitter almonds [benzaldehyde].)

[14] Laurent, Auguste (1836) "Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique," Annales de Chemie et de Physique, vol. 63, pp. 27–45, see p. 44: "Je donne le nom de phène au radical fondamental des acides précédens (φαινω, j'éclaire), puisque la benzine se trouve dans le gaz de l'éclairage." (I give the name of "phène" (φαινω, I illuminate) to the fundamental radical of the preceding acid, because benzene is found in illuminating gas.)

[August_Kekul.C3.A9-15] Kekulé, August (1872). "Ueber einige Condensationsproducte des Aldehyds". Liebigs Ann. Chem. 162 (1): 77–124. doi:10.1002/jlac.18721620110.

[16] Hofmann, A. W. (1845) "Ueber eine sichere Reaction auf Benzol" (On a reliable test for benzene), Annalen der Chemie und Pharmacie, vol. 55, pp. 200–205; on pp. 204–205, Hofmann found benzene in coal tar oil.

[17] Mansfield, Charles Blachford (1849) "Untersuchung des Steinkohlentheers" (Investigation of coal tar), Annalen der Chemie und Pharmacie, vol. 69, pp. 162–180.

[18] Charles Mansfield filed for (November 11, 1847) and received (May 1848) a patent (no. 11,960) for the fractional distillation of coal tar.

[19] Hoffman, Augustus W. (1856). "On insolinic acid". Proceedings of the Royal Society 8: 1–3. doi:10.1098/rspl.1856.0002. "The existence and mode of formation of insolinic acid prove that to the series of monobasic aromatic acids, C_n2H_n2-8O₄, the lowest known term of which is benzoic acid, ...." [Note: The empirical formulas of organic compounds that appear in Hoffmann's article (p. 3) are wrong because he uses the incorrect atomic masses of carbon (6 instead of 12) and oxygen (8 instead of 16).]

[Cernicharo_546-20] Cernicharo, José et al. (1997), "Infrared Space Observatory's Discovery of C₄H₂, C₆H₂, and Benzene in CRL 618", Astrophysical Journal Letters 546 (2): L123–L126, Bibcode:2001ApJ...546L.123C, doi:10.1086/318871

[21] J. Loschmidt, Chemische Studien (Vienna, Austria-Hungary: Carl Gerold's Sohn, 1861), pp. 30, 65.

[22] Kekulé, F. A. (1865). "Sur la constitution des substances aromatiques". Bulletin de la Societe Chimique de Paris 3: 98–110. On p. 100, Kekulé suggests that the carbon atoms of benzene could form a "chaîne fermée" (a closed chain, a loop).

[23] Kekulé, F. A. (1866). "Untersuchungen über aromatische Verbindungen] (Investigations of aromatic compounds)". Liebigs Annalen der Chemie und Pharmacie 137 (2): 129–36. doi:10.1002/jlac.18661370202.

[24] Rocke, A. J. (2010) Image and Reality: Kekule, Kopp, and the Scientific Imagination, University of Chicago Press, pp. 186–227, ISBN 0226723356.

[25] Critics pointed out a problem with Kekulé's original (1865/1866) structure for benzene: Whenever benzene underwent substitution at the ortho position, two distinguishable isomers should have resulted, depending on whether the double bond at the ortho position extended clockwise or counterclockwise; however, no such isomers were observed. In 1872, Kekulé suggested that benzene had two complementary structures and that these forms rapidly interconverted, so that if there were a double bond between any pair of carbon atoms at one instant, that double bond would become a single bond at the next instant (and vice-versa). To provide a mechanism for the conversion process, Kekulé proposed that the valency of an atom is determined by the frequency with which it collided with its neighbors in a molecule. As the carbon atoms in the benzene ring collided with each other, each carbon atom would collide twice with one neighbor during a given interval and then twice with its other neighbor during the next interval. Thus, a double bond would exist with one neighbor during the first interval and the other neighbor during the next interval. See pages 86–89 of Auguste Kekulé (1872) "Ueber einige Condensationsprodukte des Aldehyds" (On some condensation products of aldehydes), Liebig's Annalen der Chemie und Pharmacie, 162(1): 77–124, 309–320.

[26] 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. 207

[27] Dewar, James (1867) "On the oxidation of phenyl alcohol, and a mechanical arrangement adapted to illustrate structure in the non-saturated hydrocarbons," Proceedings of the Royal Society of Edinburgh 6: 82–86.

[28] Ladenburg, Albert (1869) "Bemerkungen zur aromatischen Theorie" (Observations on the aromatic theory), Berichte der Deutschen Chemischen Gesellschaft 2: 140–142.

[29] Armstrong, Henry E. (1887) "An explanation of the laws which govern substitution in the case of benzenoid compounds," Journal of the Chemical Society, 51, 258–268; see p. 264.

[30] 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. Die aromatischen Verbindungen. Das Benzol." (VIII. The aromatic compounds. Benzene.), pp. 125–129. See further: Thiele (1901) "Zur Kenntnis der ungesättigen Verbindungen," Justus Liebig’s Annalen der Chemie, 319: 129–143.

[31] Read, John (1995). From alchemy to chemistry. New York: Dover Publications. pp. 179–180. ISBN 9780486286907.

[32] English translation Wilcox, David H.; Greenbaum, Frederick R. (1965). "Kekule's benzene ring theory: A subject for lighthearted banter". Journal of Chemical Education 42 (5): 266–67. Bibcode:1965JChEd..42..266W. doi:10.1021/ed042p266.

[33] Kekulé, F. A. (1890). "Benzolfest: Rede". Berichte der Deutschen Chemischen Gesellschaft 23: 1302–11. doi:10.1002/cber.189002301204.

[34] Benfey O. T. (1958). "August Kekulé and the Birth of the Structural Theory of Organic Chemistry in 1858". Journal of Chemical Education 35: 21–23. Bibcode:1958JChEd..35...21B. doi:10.1021/ed035p21.

[35] 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.

[36] Lonsdale, K. (1929). "The Structure of the Benzene Ring in Hexamethylbenzene". Proceedings of the Royal Society 123A: 494.

[37] Lonsdale, K. (1931). "An X-Ray Analysis of the Structure of Hexachlorobenzene, Using the Fourier Method". Proceedings of the Royal Society 133A (822): 536–553. Bibcode:1931RSPSA.133..536L. doi:10.1098/rspa.1931.0166.

[38] David Cooper (2002). Valence Bond Theory. Elsevier. pp. 125–131. ISBN 0-080-54349-9.

[39] Moran D, Simmonett AC, Leach FE, Allen WD, Schleyer PV, Schaefer HF (2006). "Popular Theoretical Methods Predict Benzene and Arenes To Be Nonplanar". Journal of the American Chemical Society 128 (29): 9342–3. doi:10.1021/ja0630285. PMID 16848464.

[40] Cooper, David L.; Gerratt, Joseph; Raimondi, Mario (1986). "The electronic structure of the benzene molecule". Nature 323 (6090): 699. Bibcode:1986Natur.323..699C. doi:10.1038/323699a0.

[41] Pauling, Linus (1987). "Electronic structure of the benzene molecule". Nature 325 (6103): 396. Bibcode:1987Natur.325..396P. doi:10.1038/325396d0.

[42] Messmer, Richard P.; Schultz, Peter A. (1987). "The electronic structure of the benzene molecule". Nature 329 (6139): 492. Bibcode:1987Natur.329..492M. doi:10.1038/329492a0.

[43] Harcourt, Richard D. (1987). "The electronic structure of the benzene molecule". Nature 329 (6139): 491. Bibcode:1987Natur.329..491H. doi:10.1038/329491b0.

[44] "Unicode Character 'BENZENE RING' (U+232C)". fileformat.info. Retrieved 2009-01-16.

[45] "Unicode Character 'BENZENE RING WITH CIRCLE' (U+23E3)". fileformat.info. Retrieved 2009-01-16.

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[StranksEtAl1970-49] Stranks, D. R.; M. L. Heffernan; K. C. Lee Dow; P. T. McTigue; G. R. A. Withers (1970). Chemistry: A structural view. Carlton, Victoria: Melbourne University Press. p. 347. ISBN 0-522-83988-6.

[50] Welch, Vincent A.; Fallon, Kevin J. and Gelbke, Heinz-Peter (2005) “Ethylbenzene” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, doi:10.1002/14356007.a10_035.pub2

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