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Benzene

Benzene

Benzene, also known as C₆H₆, PhH, and benzol, is an organic chemical compound which is a colorless and flammable liquid with a pleasant, sweet smell. Benzene is a known carcinogen. It is a component of gasoline. It is an important industrial solvent and precursor in the production of drugs, plastics, gasoline, synthetic rubber, and dyes. Benzene is a natural constituent of crude oil, but it is usually synthesized from other compounds present in petroleum. Benzene is an aromatic hydrocarbon, and the second [n]-annulene ([6]-annulene).

History

Benzene was discovered in 1825 by the English scientist Michael Faraday, who isolated it from oil gas and gave it the name bicarburet of hydrogen. In 1833, the German chemist Eilhard Mitscherlich produced it via the distillation of benzoic acid (from gum benzoin) and lime. Mitscherlich gave the compound the name benzin. In 1845, the English chemist Charles Mansfield, working under August Wilhelm von Hofmann, isolated benzene from coal tar. Four years later, Mansfield began the first industrial-scale production of benzene, based on the coal-tar method.

Structure

The formula of benzene (C₆H₆) caused a mystery for some time after its discovery, as no explanation had been found that could account for all the bonds — carbon usually forms four single bonds and hydrogen one. The chemist Friedrich August Kekulé von Stradonitz was the first to deduce the ring structure of benzene. An often-repeated story claims that after years of studying carbon bonding, benzene and related molecules, he dreamt one night of a snake eating its own tail (see Ouroboros), and that upon waking he was inspired to deduce the ring structure of benzene. However, the story first appeared in the Berichte der Durstigen Chemischen Gesellschaft (Journal of the Thirsty Chemical Society), a parody of the Berichte der Deutschen Chemischen Gesellschaft which appeared annually in the late 19th century on the occasion of the congress of German chemists; as such, it is probably to be treated with circumspection. While his (more formal) claims were well publicized and accepted, by the early 1920s Kekulé's biographer came to the conclusion that Kekulé's understanding of the tetravalent nature of carbon bonding depended on the previous research of Archibald Scott Couper (1831-1892); further, the Austrian chemist Josef Loschmidt (1821-1895) had earlier posited a cyclic structure for benzene as early as 1862. The cyclic nature of benzene was finally confirmed by the eminent crystallographer Kathleen Lonsdale. Benzene presents a special problem in that, to account for all the bonds, there must be alternating double carbon bonds: Benzene with alternating double bonds Using X-ray diffraction, researchers discovered that all of the carbon-carbon bonds in benzene are of the same length, and it is known that a single bond is longer than a double bond. In addition, the bond length (the distance between the two bonded atoms) in benzene is greater than a double bond, but shorter than a single bond. There seems in effect to be a bond and a half between each carbon. This is explained by electron delocalization. In order to picture this, we must consider the position of electrons in the bonds of benzene. One representation is that the structure exists as a superposition of the forms below, rather than either form individually. This type of structure is called a resonance hybrid. Benzene, mesomeric structures In reality, neither form really exists. Delocalisation must be explained using a higher level of theory than single and double bonds. The single bonds are formed with electrons in line between the carbon atoms - this is called σ (sigma) symmetry. Double bonds consist of a sigma bond and another, π (pi) bond. This second bond has electrons orbiting in paths above and below the plane of the ring at each bonded carbon atom. The π-bonds are formed from atomic p-orbitals above and below the plane of ring. The following diagram shows the positions of these p-orbitals: atomic p-orbitals Since they are out of the plane of the atoms, these orbitals can interact with each other freely, and become delocalised. This means that instead of being tied to one atom of carbon, each electron is shared by all six in the ring. Thus there are not enough electrons to form double bonds on all the carbon atoms, but the "extra" electrons strengthen all of the bonds on the ring equally. The resulting molecular orbital has π symmetry. Benzene orbital delocalisation This delocalisation of electrons is known as aromaticity, and gives benzene great stability. This is the fundamental property of aromatic chemicals which differentiates them from non-aromatics. To reflect the delocalised nature of the bonding, benzene may be depicted as a circle inside a hexagon in chemical structure diagrams: Benzene structure with a circle inside the hexagon As is common in diagrams of organic structures, the carbon atoms in the diagram above have been left unlabeled. Benzene occurs sufficiently often as a component of organic molecules that there is a Unicode symbol with the code 232C to represent it: ⌬ Note: Many fonts do not have this Unicode character, so your browser may not be able to display it correctly.

Substituted benzenes

Many important chemicals are essentially benzene, with one or more of the hydrogen atoms replaced with another functional group:

Alkyl substituents (alkylbenzenes)

- Ethylbenzene C₆H₅-CH₂-CH₃
- Mesitylene C₆H₃(-CH₃)₃
- Toluene C₆H₅-CH₃
- Xylene C₆H₄(-CH₃)₂

Other substituents

- Aniline C₆H₅-NH₂
- Acetylsalicylic acid C₆H₄(-O-C(=O)-CH₃)(-COOH)
- Benzoic acid C₆H₅-COOH
- Biphenyl (C₆H₅)₂
- Chlorobenzene C₆H₅-Cl
- Nitrobenzene C₆H₅-NO₂
- Paracetamol C₆H₄(-NH-C(=O)-CH₃)(-OH)
- Phenacetin C₆H₄(-NH-C(=O)-CH₃)(-O-CH₂-CH₃)
- Phenol C₆H₅-OH
- Picric acid C₆H₂(-OH)(-NO₂)₃
- Salicylic acid C₆H₄(-OH)(-COOH)
- Trinitrotoluene C₆H₂(-CH₃)(-NO₂)₃

Fused aromatic rings

- Anthracene
- Benzofuran
- Indole
- Isoquinoline
- Naphthalene
- Phenanthrene
- Polycyclic aromatic hydrocarbons (PAH)
- Quinoline

Heterocyclic analogs

In heterocycles, carbon atoms in the benzene ring are replaced with another element:
- Pyrazine
- Pyridazine
- Pyridine
- Pyrimidine See Simple aromatic ring for analogs of benzene.

Production

Benzene may result whenever carbon-rich materials undergo incomplete combustion. It is produced naturally in volcanoes and forest fires, and is also a component of cigarette smoke. Up until World War II, most benzene was produced as a byproduct of coke production in the steel industry. However, in the 1950s, increased demand for benzene, especially from the growing plastics 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. Three chemical processes contribute equally to industrial benzene production: catalytic reforming, toluene hydrodealkylation, and steam cracking.

Catalytic reforming

In catalytic reforming, a mixture of hydrocarbons with boiling points between 60-200°C is blended with hydrogen gas, then exposed to a 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 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.

Toluene hydrodealkylation

Toluene hydrodealkylation converts toluene to benzene. In this 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. Under these conditions, toluene undergoes dealkylation according to the chemical equation: :C₆H₅CH₃ + H₂ → C₆H₆ + CH₄ Typical reaction yields exceed 95%. Sometimes, xylene and heavier aromatics are used in place of toluene, with similar efficiency.

Steam cracking

Steam cracking is the process used to produce ethylene and other olefins from aliphatic hydrocarbons. Depending on the feedstock used to produce the olefins, steam cracking can produce a benzene-rich liquid byproduct called pyrolysis gasoline. Pyrolysis gasoline can be blended with other hydrocarbons as a gasoline additive, or distilled to separate it into its components, including benzene.

Uses

In the 19th and early 20th centuries, benzene was used as an aftershave 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, other solvents replaced benzene in applications that directly exposed the user to benzene. As a gasoline additive, benzene increases the octane rating and reduces knocking. As a result, gasoline often contained several percent benzene before the 1950s, when tetraethyl lead replaced it as the most widely used antiknock additive. However, 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 entering the groundwater have led to stringent regulation of gasoline's benzene content, with values around 1% typical. European gasoline specifications now contain the same 1% limit on benzene content. By far the largest use of benzene is as an intermediate to make other chemicals. The most widely produced derivatives of benzene are styrene, which is used to make polymers and plastics, phenol for resins and adhesives (via cumene), and cyclohexane, which is used in Nylon manufacture. Smaller amounts of benzene are used to make some types of rubbers, lubricants, dyes, detergents, drugs, explosives and pesticides. In laboratory research, toluene is now often substituted for benzene because of health concerns.

Reactions of benzene

Electrophilic aromatic substitution

Electrophilic aromatic substitution is a general method of substituting aromatic rings such as benzene. Benzene is nucleophilic enough, so that in the presence of strong electrophiles such as acylium ions or alkyl carbocations, reaction will occur to ultimately give substituted benzenes. Electrophilic aromatic substitution

Friedel-Crafts acylation

The Friedel-Crafts acylation is a specific example of electrophilic aromatic substitution. The reaction is the acylation of an aromatic ring (such as benzene) with an acyl chloride using a strong Lewis acid catalyst. Lewis acid

Friedel-Crafts alkylation

Like the Friedel-Crafts acylation, the Friedel-Crafts alkylation involves the alkylation of an aromatic ring (such as benzene) and an alkyl halide using a strong Lewis acid catalyst. alkyl halide

Health effects

Breathing very high levels of benzene can result in death, while high 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, irritation of the stomach, dizziness, sleepiness, convulsions, rapid heart rate, and death. The major effect of benzene from chronic (long term) exposure is to the blood. Benzene damages the bone marrow and can cause a decrease in red blood cells leading to anemia. It can also cause excessive bleeding and depress the immune system, increasing the chance of infection. Some women who breathed high levels of benzene for many months had irregular menstrual periods and a decrease in the size of their ovaries. It is not known whether benzene exposure affects the developing 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 US Department of Health and Human Services (DHHS) classifies benzene as a human carcinogen. Long-term exposure to high levels of benzene in the air can cause leukemia, a potentially fatal cancer of the blood-forming organs. In particular, Acute Myeloid Leukemia (AML) may be caused by benzene. Several tests can show if you have been exposed to benzene. There is a test for measuring benzene in the breath; this test must be done shortly after exposure. Benzene can also be measured in the blood; however, since benzene disappears rapidly from the blood, measurements are accurate only for recent exposures. In the body, benzene is metabolized. Certain metabolites can be measured in the urine. However, this test must be done shortly after exposure and is not a reliable indicator of how much benzene you have been exposed to, since the same metabolites may be present in urine from other sources. The US Environmental Protection Agency has set the maximum permissible level of benzene in drinking water at 0.005 milligrams per liter (0.005 mg/L). The EPA requires that spills or accidental releases into the environment of 10 pounds (4.5 kg) or more of benzene be reported to the EPA. The US 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.

Benzene exposure

Workers in various industries that make or use benzene may be at risk for being exposed to high levels of this carcinogenic chemical. Industries that involve the use of benzene include the rubber industry, oil refineries, chemical plants, shoe manufacturers, and 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. 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, from an explosion at a China National Petroleum Corporation (CNPC) factory in the city of Jilin on 13 November.

References

- Archibald Scott Couper, On a New Chemical Theory, Philosophical Magazine 16, 104-116 (1858)
- Josef Loschmidt, Chemische Studien I, Carl Gerold's Sohn, Vienna (1861),
- Josef Loschmidt, Chemische Studien I, Aldrich Chemical Co, Milwaukee (1989), catalog no. Z-18576-0, and (1913) catalog no. Z-18577-9
- Kathleen Lonsdale, "The Structure of the Benzene Ring in Hexamethylbenzene," Proceedings of the Royal Society 123A: 494 (1929).
- Kathleen Lonsdale, "An X-Ray Analysis of the Structure of Hexachlorobenzene, Using the Fourier Method," Proceedings of the Royal Society 133A: 536 (1931).

External links

- [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc00/icsc0015.htm International Chemical Safety Card 0015]
- [http://www.cdc.gov/niosh/npg/npgd0049.html NIOSH Pocket Guide to Chemical Hazards]
- [http://www-cie.iarc.fr/htdocs/monographs/suppl7/benzene.html IARC Monograph: "Benzene"]
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- [http://www.hazard.com/msds/f2/bqv/bqvjq.html Benzene Material Safety Data Sheet]
- [http://www.atsdr.cdc.gov/HEC/CSEM/benzene/ Case Studies in Environmental Medicine: Benzene Toxicity]
- [http://www.compchemwiki.org/index.php?title=Benzene Computational Chemistry Wiki]
- [http://classes.yale.edu/chem125a/125/history99/5Valence/Couper/Couper.html Couper and Carbon bonds]
- [http://ntp.niehs.nih.gov/index.cfm?objectid=0707525C-0F07-05BF-A16CAC7B0ECC97B5 Dept. of Health and Human Services: TR-289: Toxicology and Carcinogenesis Studies of Benzene]
- [http://classes.yale.edu/chem125a/125/history99/5Valence/Kekule/Kekule.html Kekule, Couper and dreams of Benzene]
- [http://www.physicstoday.org/pt/vol-54/iss-3/captions/p45cap4.html Loschmidt's Benzene structure]
- [http://www.sgipt.org/th_schul/pa/kek/pak_kek0.htm Kekulés Traum] (Kekulé's dream, in German) Category:Annulenes Category:Simple_aromatic_rings Category:IARC Group 1 carcinogens Category:Solvents Category:Aromatic hydrocarbons ja:????

Carbon

:Alternative meaning: Carbon (API) :For the portable music player, see Rio Carbon Carbon is a chemical element in the periodic table that has the symbol C and atomic number 6. An abundant nonmetallic, tetravalent element, carbon has several allotropic forms:
- Diamond (hardest known natural mineral). Structure: each atom is bonded tetrahedrally to four others, making a 3-dimensional network of puckered six-membered rings of atoms.
- Graphite (one of the softest substances). Structure: each atom is bonded trigonally to three other atoms, making a 2-dimensional network of flat six-membered rings; the flat sheets are loosely bonded.
- Fullerenes. Structure: comparatively large molecules formed completely of carbon bonded trigonally, forming spheroids (of which the best-known and simplest is the buckminsterfullerene or buckyball).
- Chaoite A mineral supposedly formed in meteorite impacts.
- Lonsdaleite (a corruption of diamond). Structure: similar to diamond, but forming a hexagonal crystal lattice.
- Amorphous carbon (a glassy substance). Structure: an assortment of carbon molecules in a non-crystalline, irregular, glassy state.
- Carbon nanofoam (an extremely light magnetic web). Structure: a low-density web of graphite-like clusters, in which the atoms are bonded trigonally in six- and seven-membered rings.
- Carbon nanotubes (tiny tubes). Structure: each atom is bonded trigonally in a curved sheet that forms a hollow cylinder.
- Aggregated diamond nanorods, the most recently discovered allotrope. Lamp black consists of small graphitic areas. These areas are randomly distributed, so the whole structure is isotropic. 'Glassy carbon' is isotropic and contains a high proportion of closed porosity. Unlike normal graphite, the graphitic layers are not stacked like pages in a book, but have a more random arrangement. Carbon fibers are similar to glassy carbon. Under special treatment (stretching of organic fibers and carbonization) it is possible to arrange the carbon planes in direction of the fiber. Perpendicular to the fiber axis there is no orientation of the carbon planes. The result are fibers with a higher specific strength than steel. Carbon occurs in all organic life and is the basis of organic chemistry. This nonmetal also has the interesting chemical property of being able to bond with itself and a wide variety of other elements, forming nearly 10 million known compounds. When united with oxygen it forms carbon dioxide which is absolutely vital to plant growth. When united with hydrogen, it forms various compounds called hydrocarbons which are essential to industry in the form of fossil fuels. When combined with both oxygen and hydrogen it can form many groups of compounds including fatty acids, which are essential to life, and esters, which give flavor to many fruits. The isotope carbon-14 is commonly used in radioactive dating.

Notable characteristics

Carbon is a remarkable element for many reasons. Its different forms include one of the softest (graphite) and one of the hardest (diamond) substances known to humankind. Moreover, it has a great affinity for bonding with other small atoms, including other carbon atoms, and its small size makes it capable of forming multiple bonds. Because of these properties, carbon is known to form nearly ten million different compounds, the large majority of all chemical compounds. Carbon compounds form the basis of all life on Earth and the carbon-nitrogen cycle provides some of the energy produced by the sun and other stars. Moreover, carbon has the highest melting/sublimation point of all elements. At atmospheric pressure it has no actual melting point as its triple point is at 10 MPa (100 bar) so it sublimates above 4000 K. Thus it remains solid at higher temperatures than the highest melting point metals like tungsten or rhenium, regardless of its allotropic form. Carbon was not created in the Big Bang due to the fact that it needs a triple collision of alpha particles (helium nuclei) to be produced. The universe initially expanded and cooled too fast for that to be possible. It is produced, however, in the interior of stars in the horizontal branch, where stars transform a helium core into carbon by means of the triple-alpha process. It was also created in a multi atomic state.

Applications

Carbon is a vital component of all known living systems, and without it life as we know it could not exist (see alternative biochemistry). The major economic use of carbon is in the form of hydrocarbons, most notably the fossil fuels methane gas and crude oil (petroleum). Crude oil is used by the petrochemical industry to produce, amongst others, gasoline and kerosene, through a distillation process, in refineries. Crude oil forms the raw material for many synthetic substances, many of which are collectively called plastics.

Other uses

- The isotope Carbon-14 was discovered in February 27 1940 and is used in radiocarbon dating.
- Some smoke detectors use tiny amounts of a radioactive isotope of carbon as source of ionizing radiation. (Most smoke detectors of this type use an isotope of americium.)
- Graphite is combined with clays to form the 'lead' used in pencils.
- Diamond is used for decorative purposes, and also as drill bits and other applications making use of its hardness.
- Carbon is added to iron to make steel.
- Carbon is used as a neutron moderator in nuclear reactors.
- Graphite carbon in a powdered, caked form is used as charcoal for cooking, artwork and other uses.
- Activated charcoal is used in medicine (as powder or compounded in tablets or capsules) to absorb toxins or poisons from the digestive system. The chemical and structural properties of fullerenes, in the form of carbon nanotubes, has promising potential uses in the nascent field of nanotechnology. Nanoparticles might however be toxic.

History and Etymology

Carbon was discovered in prehistory and was known to the ancients, who manufactured it by burning organic material in insufficient oxygen (making charcoal). Diamonds have long been considered rare and beautiful. One of the last-known allotropes of carbon, fullerenes, were discovered as byproducts of molecular beam experiments in the 1980s. The name comes from French charbone, which in turn came from Latin carbo, meaning charcoal. In German and Dutch, the names for carbon are Kohlenstoff and koolstof respectively, both literally meaning "coal-stuff".

Allotropes

The allotropes of carbon are the different molecular configurations (allotropes) that pure carbon can take. The three relatively well-known allotropes of carbon are amorphous carbon, graphite, and diamond. Several exotic allotropes have also been synthesized or discovered, including fullerenes, carbon nanotubes, lonsdaleite and aggregated diamond nanorods. In its amorphous form, carbon is essentially graphite but not held in a crystalline macrostructure. It is, rather, present as a powder which is the main constituent of substances such as charcoal, lamp black (soot) and activated carbon. activated carbon, so that two phases can coexist. ]] At normal pressures carbon takes the form of graphite, in which each atom is bonded to three others in a plane composed of fused hexagonal rings, just like those in aromatic hydrocarbons. The two known forms of graphite, alpha (hexagonal) and beta (rhombohedral), both have identical physical properties, except for their crystal structure. Graphites that naturally occur have been found to contain up to 30% of the beta form, when synthetically-produced graphite only contains the alpha form. The alpha form can be converted to the beta form through mechanical treatment and the beta form reverts back to the alpha form when it is heated above 1000 °C. Because of the delocalization of the pi-cloud, graphite conducts electricity. The material is soft and the sheets, frequently separated by other atoms, are held together only by van der Waals forces, so easily slip past one another. At very high pressures carbon forms an allotrope called diamond, in which each atom is bonded to four others. Diamond has the same cubic structure as silicon and germanium and, thanks to the strength of the carbon-carbon bonds, is together with the isoelectronic boron nitride (BN) the hardest substance in terms of resistance to scratching. The transition to graphite at room temperature is so slow as to be unnoticeable. Under some conditions, carbon crystallizes as Lonsdaleite, a form similar to diamond but hexagonal. Fullerenes have a graphite-like structure, but instead of purely hexagonal packing, also contain pentagons (or possibly heptagons) of carbon atoms, which bend the sheet into spheres, ellipses or cylinders. The properties of fullerenes (also called "buckyballs" and "buckytubes") have not yet been fully analyzed. All the names of fullerenes are after Buckminster Fuller, developer of the geodesic dome, which mimics the structure of "buckyballs". A nanofoam allotrope has been discovered which is ferromagnetic. Carbon allotropes include:
- Amorphous carbon
- Carbon nanofoam (discovered in 1997)
- Carbon nanotube
- Diamond
- Fullerene
- Graphite
- Lonsdaleite
- Aggregated diamond nanorods (synthesised in 2005) The system of carbon allotropes spans a range of extremes. Between diamond and graphite:
- Graphite is soft and is used in pencils
- Diamond is the hardest mineral known to man (although aggregated diamond nanorods are now believed to be even harder), but graphite is one of the softest.
- Diamond is the ultimate abrasive, but graphite is a very good lubricant.
- Diamond is an excellent electrical insulator, but graphite is a conductor of electricity.
- Diamond is usually transparent, but graphite is opaque.
- Diamond crystallizes in the cubic system but graphite crystallizes in the hexagonal system. Between amorphous carbon and nanotubes:
- Amorphous carbon is among the easiest materials to synthesize, but carbon nanotubes are extremely expensive to make.
- Amorphous carbon is completely isotropic, but carbon nanotubes are among the most anisotropic materials ever produced.

Occurrence

There are nearly ten million carbon compounds known to science. Many thousands of these are vital to life processes. They are also many organic-based reactions of economic importance. Carbon is abundant in the sun, stars, comets, and in the atmospheres of most planets. Some meteorites contain microscopic diamonds that were formed when the solar system was still a protoplanetary disk. In combination with other elements, carbon is found the earth's atmosphere and dissolved in all water bodies. With smaller amounts of calcium, magnesium, and iron, it is a major component of very large masses carbonate rock (limestone, dolomite, marble etc.). When combined with hydrogen, carbon forms coal, petroleum, and natural gas which are called hydrocarbons. Graphite is found in large quantities in New York and Texas, the United States; Russia; Mexico; Greenland and India. Natural diamonds occur in the mineral kimberlite found in ancient volcanic "necks," or "pipes". Most diamond deposits are in Africa, notably in South Africa, Namibia, Botswana, the Republic of the Congo and Sierra Leone. There are also deposits in Arkansas, Canada, the Russian Arctic, Brazil and in Northern and Western Australia.

Organic compounds

The most prominent oxide of carbon is carbon dioxide, CO₂. This is a minor component of the Earth's atmosphere, produced and used by living things, and a common volatile elsewhere. In water it forms trace amounts of methanoic acid, HCO₂H, but as most compounds with multiple single-bonded oxygens on a single carbon it is unstable. Through this intermediate, though, resonance-stabilized carbonate ions are produced. Some important minerals are carbonates, notably calcite. Carbon disulfide, CS₂, is similar. The other oxides are carbon monoxide, CO, and the uncommon carbon suboxide, C₃O₂. Carbon monoxide is formed by incomplete combustion, and is a colorless, odorless gas. The molecules each contain a triple bond and are fairly polar, resulting in a tendency to bind permanently to haemoglobin molecules, so that the gas is highly poisonous. Cyanide, CN-, has a similar structure and behaves a lot like a halide ion; the nitride cyanogen, (CN)₂, is related. With reactive metals, such as tungsten, carbon forms either carbides, C^-, or acetylides, C₂^2- to form alloys with very high melting points. These anions are also associated with methane and acetylene, both very weak acids. All in all, with an electronegativity of 2.5, carbon prefers to form covalent bonds. A few carbides are covalent lattices, like carborundum, SiC, which resembles diamond.

Carbon chains

Carbon has the ability to form long chains with interconnecting C-C bonds. This property is called Catenation. Carbon-Carbon bonds are fairly strong, and abnormaly stable. This property is important as it allows carbon to form a huge number of compounds; if fact, there are more known carbon-containing compounds than all the other compounds of the chemical elements combined! The simplest form of an organic molecule is the hydrocarbon - a large family of organic molecules that, by definition, are composed of hydrogen atoms bonded to a chain of carbon atoms. Chain length, side chains and functional groups all affect the properties of organic molecules.

Carbon cycle

Under terrestrial conditions, conversion of one isotope to another is very rare. Therefore, for practical purposes, the amount of carbon on Earth is constant. Thus processes that use carbon must obtain it from somewhere, and dispose of it somewhere. The paths that carbon follows in the environment are called the carbon cycle. For example, plants draw carbon dioxide out of the environments and use it to build biomass. Some of this biomass is eaten by animals, where some of it is exhaled as carbon dioxide. The carbon cycle is considerably more complicated than this short loop; for example, some carbon dioxide is dissolved in the oceans; dead plant or animal matter may become sedimentary rock, and so forth.

Isotopes

Carbon has two stable, naturally-occurring isotopes: carbon-12, or ¹²C, (98.89%) and carbon-13, or ¹³C, (1.11%), and one unstable, naturally-occurring, radioisotope; carbon-14 or ¹⁴C. There are 15 known isotopes of carbon and the shortest-lived of these is ⁸C which decays through proton emission and alpha decay. It has a half-life of 1.98739x10^-21 s. In 1961 the International Union of Pure and Applied Chemistry adopted the isotope carbon-12 as the basis for atomic weights. Carbon-14 has a half-life of 5730 y and has been used extensively for radiocarbon dating carbonaceous materials.

Precautions

Carbon is relatively safe. Inhalation of fine soot in large quantities can be dangerous. Carbon may catch fire at very high temperatures and burn vigorously (as in the Windscale fire). There are a tremendous number of carbon compounds; some are lethally poisonous (cyanide, CN^-), and some are essential to life (dextrose).

References

- [http://lbruno.home.cern.ch/lbruno/documents/Bibliography/LHC_Note_78.pdf On Graphite Transformations at High Temperature and Pressure Induced by Absorption of the LHC Beam], J.M. Zazula, 1997
- WebElements.com and EnvironmentalChemistry.com per the guidelines at [http://en.wikipedia.org/wiki/Wikipedia:WikiProject_Elements Wikipedia's WikiProject Elements]

External links

- [http://periodic.lanl.gov/elements/6.html Los Alamos National Laboratory – Carbon]
- [http://www.webelements.com/webelements/elements/text/C/index.html WebElements.com – Carbon]
- [http://education.jlab.org/itselemental/ele006.html It's Elemental – Carbon]
- [http://www.vincentherr.com/cf/ – Carbon Fullerene and other Allotropes] models by Vincent Herr
- [http://invsee.asu.edu/nmodules/Carbonmod/everywhere.html Extensive Carbon page at asu.edu]
- [http://electrochem.cwru.edu/ed/encycl/art-c01-carbon.htm Electrochemical uses of carbon]
- [http://www.compchemwiki.org/index.php?title=Carbon Computational Chemistry Wiki] Category:Chemical elements Category:Nonmetals Category:Materials ko:탄소 ms:Karbon ja:炭素 simple:Carbon th:คาร์บอน

Hydrogen

|- | Critical temperature || 32.19 K |- | Critical pressure || 1.315 MPa |- | Critical density || 30.12 g/L (Bohr radius) Hydrogen (Latin: hydrogenium, from Greek: hydro: water, genes: forming) is a chemical element in the periodic table that has the symbol H and atomic number 1. At standard temperature and pressure it is a colorless, odorless, nonmetallic, univalent, highly flammable diatomic gas. Hydrogen is the lightest and most abundant element in the universe. It is present in water, all organic compounds (rare exceptions exist, like buckminsterfullerene) and in all living organisms. Hydrogen is able to react chemically with most other elements. Stars in their main sequence are overwhelmingly composed of hydrogen in its plasma state. The element is used in ammonia production, as a lifting gas, as an alternative fuel, and more recently as a power source of fuel cells. Despite its ubiquity in the universe, hydrogen is surprisingly hard to produce in large quantities on the Earth. In the laboratory, the element is prepared by the reaction of acids on metals such as zinc. The electrolysis of water is a simple method of producing hydrogen, but is economically inefficient for mass production. Large-scale production is usually achieved by steam reforming natural gas. Scientists are now researching new methods for hydrogen production; if they succeed in developing a cost-efficient method of large-scale production, hydrogen may become a viable alternative to greenhouse-gas-producing fossil fuels. One of the methods under investigation involves use of green algae; another promising method involves the conversion of biomass derivatives such as glucose or sorbitol at low temperatures using a catalyst. Yet another method is the "steaming" of Carbon, whereby hydrocarbons are broken down with heat to release hydrogen.

Basic features

Hydrogen is the lightest chemical element; its most common isotope comprises just one negatively charged electron, distributed around a positively charged proton (the nucleus of the atom). The electron is bound to the proton by the Coulomb force, the electrical force that one stationary, electrically charged nanoparticle exerts on another. The hydrogen atom has special significance in quantum mechanics as a simple physical system for which there is an exact solution to the Schrödinger equation; from that equation, the experimentally observed frequencies and intensities of the hydrogen's spectral lines can be calculated. Spectral lines are dark or bright lines in an otherwise uniform and continuous spectrum, resulting from an excess or deficiency of photons in a narrow frequency range, compared with the nearby frequencies. At standard temperature and pressure, hydrogen forms a diatomic gas, H₂, with a boiling point of only 20.27 K and a melting point of 14.02 K. Under extreme pressures, such as those at the center of gas giants, the molecules lose their identity and the hydrogen becomes a liquid metal. Under the extremely low pressure in space—virtually a vacuum—the element tends to exist as individual atoms, simply because there is no way for them to combine. However, clouds of H₂ and singular hydrogen atoms are said to form in H I and H II regions and are associated with star formation, however the existence of singular hydrogen atoms is disputed.. Hydrogen plays a vital role in powering stars through the proton–proton and carbon–nitrogen cycle. These are nuclear fusion processes, which release huge amounts of energy in stars and other hot celestial bodies as hydrogen atoms combine into helium atoms. H₂ is highly soluble in water, alcohol, and ether. It has a high capacity for adsorption, in which it is attached to and held to the surface of some substances. It is an odorless, tasteless, colorless, and highly flammable gas that burns at concentrations as low as 4% H₂ in air. It reacts violently with chlorine and fluorine, forming hydrohalic acids that can damage the lungs and other tissues. When mixed with oxygen, hydrogen explodes on ignition. A unique property of hydrogen is that its flame is completely invisible in air. This makes it difficult to tell if a leak is burning, and carries the added risk that it is easy to walk into a hydrogen fire inadvertently. See also: hydrogen atom.

Applications

Large quantities of hydrogen are needed in the chemical and petrolium industries, notably in the Haber process for the production of ammonia, which by mass ranks as the world's fifth most highly produced industrial compound. Hydrogen is used in the hydrogenation of fats and oils (into items such as margarine), and in the production of methanol. Hydrogen is used in hydrodealkylation, hydrodesulfurization, and hydrocracking. The element has several other important uses.
- The element is used in the manufacture of hydrochloric acid, in welding processes, and in the reduction of metallic ores.
- It is an ingredient in rocket fuels.
- It is used as the rotor coolant in electrical generators at power stations, because it has the highest thermal conductivity of any gas.
- Liquid hydrogen is used in cryogenic research, including superconductivity studies.
- Since hydrogen is 14.5 times lighter than air, it was once widely used as a lifting agent in balloons and airships. However, this use was curtailed when the Hindenburg disaster convinced the public that the gas was too dangerous for this purpose.
- Deuterium, an isotope of hydrogen (hydrogen-2), is used in nuclear fission applications as a moderator to slow neutrons, and in nuclear fusion reactions. Deuterium compounds have applications in chemistry and biology in studies of reaction isotope effects.
- Tritium (hydrogen-3), produced in nuclear reactors, is used in the production of hydrogen bombs, as an isotopic label in the biosciences, and as a radiation source in luminous paints. There are no "hydrogen wells" or "hydrogen mines" on Earth, so hydrogen cannot be considered a primary energy source like fossil fuels or uranium. Hydrogen can however be burned in internal combustion engines, an approach advocated by BMW's experimental hydrogen car. However, it is currently difficult and dangerous to store and handle in sufficient quantity for motor fuel use. Hydrogen fuel cells are being investigated as mobile power sources with lower emissions than hydrogen-burning internal combustion engines. The low emissions of hydrogen in internal combustion engines and fuel cells are currently offset by the pollution created by hydrogen production. This may change if the substantial amounts of electricity required for water electrolysis can be generated primarily from low pollution sources such as nuclear energy or wind. Research is being conducted on hydrogen as a replacement for fossil fuels. It could become the link between a range of energy sources, carriers and storage. Hydrogen can be converted to and from electricity (solving the electricity storage and transport issues), from bio-fuels, and from and into natural gas and diesel fuel. All of this can theoretically be achieved with zero emissions of CO₂ and toxic pollutants.

History

Hydrogen was first produced by Theophratus Bombastus von Hohenheim (1493–1541)—also known as Paracelsus—by mixing metals with acids. He was unaware that the explosive gas produced by this chemical reaction was hydrogen. In 1671, Robert Boyle described the reaction between two iron fillings and dilute acids, which results in the production of gaseous hydrogen. In 1766, Henry Cavendish was the first to recognize hydrogen as a discrete substance, by identifying the gas from this reaction as "inflammable" and finding that the gas produces water when burned in air. Cavendish stumbled on hydrogen when experimenting with acids and mercury. Although he wrongly assumed that hydrogen was a compound of mercury—and not of the acid—he was still able to accurately describe several key properties of hydrogen. Antoine Lavoisier gave the element its name and proved that water is composed of hydrogen and oxygen. One of the first uses of the element was for balloons. The hydrogen was obtained by mixing sulfuric acid and iron. Harold C. Urey discovered Deuterium, an isotope of hydrogen, by repeated distilling the same sample of water. For this discovery, Urey received the Nobel prize for in 1934. In the same year, the third isotope, tritium, was discovered. Because of its relatively simple structure, hydrogen has often been used in models of how an atom works.

Electron energy levels

The ground state energy level of the electron in a Hydrogen atom is 13.6 eV, which is equivalent to an ultraviolet photon of roughly 92 nm. With the Bohr Model the energy levels of Hydrogen can be calculated fairly accurately. This is done by modeling the electron as revolving around the proton, much like the earth revolving around the sun. Except the sun holds earth in orbit with the force of gravity, but the proton holds the electron in orbit with the force of electromagnetism. Another difference between the Earth-Sun system and the Electron-Proton system is that, in this model, due to quantum mechanics the electron is allowed to only be at very specific distances from the proton. Modeling the hydrogen atom in this fashion yields the correct energy levels and spectrum.

Occurrence

quantum mechanics.]] Hydrogen is the most abundant element in the universe, making up 75% of normal matter by mass and over 90% by number of atoms. This element is found in great abundance in stars and gas giant planets. It is very rare in the Earth's atmosphere (1 ppm by volume), because being the lightest gas causes it to escape Earth's gravity, though when compounds are considered, it is the tenth most abundant element on Earth. The most common source for this element on Earth is water, which is composed two parts hydrogen to one part oxygen (H₂O). Other sources include most forms of organic matter (currently all known life forms) including coal, natural gas, and other fossil fuels. Methane (CH₄) is an increasingly important source of hydrogen. Throughout the Universe, hydrogen is mostly found in the plasma state whose properties are quite different to molecular hydrogen. As a plasma, hydrogen's electron and proton are not bound together, resulting in very high electrical conductivity, even when the gas is only partially ionised. The charged particles are highly influenced by magnetic and electric fields, for example, in the Solar Wind they interact with the Earth's magnetosphere giving rise to Birkeland currents and the aurora. Hydrogen can be prepared in several different ways: steam on heated carbon, hydrocarbon decomposition with heat, reaction of a strong base in an aqueous solution with aluminium, water electrolysis, or displacement from acids with certain metals. Commercial bulk hydrogen is usually produced by the steam reforming of natural gas. At high temperatures (700–1100 °C), steam reacts with methane to yield carbon monoxide and hydrogen. :CH₄ + H₂O → CO + 3 H₂ Additional hydrogen can be recovered from the carbon monoxide through the water-gas shift reaction: :CO + H₂O → CO₂ + H₂

Compounds

The lightest of all gases, hydrogen combines with most other elements to form compounds. Hydrogen has an electronegativity of 2.2, so it forms compounds where it is the more nonmetallic and where it is the more metallic element. The former are called hydrides, where hydrogen either exists as H^- ions or just as a solute within the other element (as in palladium hydride). The latter tend to be covalent, since the H⁺ ion would be a bare nucleus and so has a strong tendency to pull electrons to itself. These both form acids. Thus even in an acidic solution one sees ions like hydronium (H₃O⁺) as the protons latch on to something. Although exotic on earth, one of the most common ions in the universe is the H₃⁺ ion. Hydrogen combines with oxygen to form water, H₂O, and releases a lot of energy in doing so, burning explosively in air. Deuterium oxide, or D₂O, is commonly referred to as heavy water. Hydrogen also forms a vast array of compounds with carbon. Because of their association with living things, these compounds are called organic compounds, and the study of the properties of these compounds is called organic chemistry. organic chemistry

Forms

Under normal conditions, hydrogen gas is a mix of two different kinds of molecules which differ from one another by the relative spin of the nuclei. These two forms are known as ortho- and para-hydrogen (this is different from isotopes, see below). In ortho-hydrogen the nuclear spins are parallel (form a triplet), while in para they are antiparallel (form a singlet). At standard conditions hydrogen is composed of about 25% of the para form and 75% of the ortho form (the so-called "normal" form). The equilibrium ratio of these two forms depends on temperature, but since the ortho form has higher energy (is an excited state), it cannot be stable in its pure form. In low temperatures (around boiling point), the equilibrium state is comprised almost entirely of the para form. The conversion process between the forms is slow, and if hydrogen is cooled down and condensed rapidly, it contains large quantities of the ortho form. It is important in preparation and storage of liquid hydrogen, since the ortho-para conversion produces more heat than the heat of its evaporation, and a lot of hydrogen can be lost by evaporation in this way during several days after liquefying. Therefore, some catalysts of the ortho-para conversion process are used during hydrogen cooling. The two forms have also slightly different physical properties. For example, the melting and boiling points of parahydrogen are about 0.1 K lower than of the "normal" form.

Isotopes

Hydrogen is the only element that has different names for its isotopes. (During the early study of radioactivity, various heavy radioactive isotopes were given names, but such names are no longer used, although one element, radon, has a name that originally applied to only one of its isotopes.) The symbols D and T (instead of ²H and ³H) are sometimes used for deuterium and tritium, although this is not officially sanctioned. (The symbol P is already in use for phosphorus and is not available for protium.) ;¹H The most common isotope of hydrogen, this stable isotope has a nucleus consisting of a single proton; hence the descriptive, although rarely used, name protium. The spin of a protium atom is 1/2+. ;²H The other stable isotope is deuterium, with an extra neutron in the nucleus. Deuterium comprises 0.0184%–0.0082% of all hydrogen (IUPAC); ratios of deuterium to protium are reported relative to the VSMOW standard reference water. The spin of a deuterium atom is 1+. ;³H The third naturally occurring hydrogen isotope is the radioactive tritium. The tritium nucleus contains two neutrons in addition to the proton. It decays through beta decay and has a half-life of 12.32 years. Tritium occurs naturally due to cosmic rays interacting with atmospheric gases. Like ordinary hydrogen, tritium reacts with the oxygen in the atmosphere to form T₂O. This radioactive "water" molecule constantly enters the Earth's seas and lakes in the form of slightly radioactive rain, but its half-life is short enough to prevent a buildup of hazardous radioactivity. The spin of a tritium atom is 1/2+. ;⁴H Hydrogen-4 was synthesized by bombarding tritium with fast-moving deuterium nuclei. It decays through neutron emission and has a half-life of 9.93696x10^-23 seconds. The spin of a hydrogen-4 atom is 2-. ;⁵H In 2001 scientists detected hydrogen-5 by bombarding a hydrogen target with heavy ions. It decays through neutron emission and has a half-life of 8.01930x10^-23 seconds. ;⁶H Hydrogen-6 decays through triple neutron emission and has a half-life of 3.26500^-22 seconds. ;⁷H In 2003 hydrogen-7 was created ([http://physicsweb.org/articles/news/7/3/3 article]) at the RIKEN laboratory in Japan by colliding a high-energy beam of helium-8 atoms with a cryogenic hydrogen target and detecting tritons—the nuclei of tritium atoms—and neutrons from the breakup of hydrogen-7, the same method used to produce and detect hydrogen-5.

References

# # # # # #
- [http://www.riken.go.jp/engn/r-world/research/lab/wako/ribeam/ RIKEN Beam Science Laboratory, Japan - Heavy hydrogen research]
- [http://chartofthenuclides.com/default.html Nuclides and Isotopes] Fourteenth Edition: Chart of the Nuclides, General Electric Company, 1989 ;Book references:
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External links

- [http://www.hydropole.ch/Hydropole/Intro/Phasediag.gif Hydrogen phase diagram.]
- [http://www.compchemwiki.org/index.php?title=Hydrogen Computational Chemistry Wiki] Category:Nonmetals Category:Fuels Category:Chemical elements ko:수소 ms:Hidrogen ja:水素 simple:Hydrogen th:ไฮโดรเจน

Phenyl

In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula :-C₆H₅ where the six carbon atoms are arranged in a cyclic manner. This hydrophobic and aromatic hydrocarbon unit can be found in many organic compounds. It can be thought of as being derived from benzene (C₆H₆). One of the simplest phenyl containing compounds is phenol. Presence of a phenyl group typically results in an ¹H-NMR shift around 7.4ppm. The phenylene group is formally a benzene di-radical. For example, poly(p-phenylene) is a polymer built up from phenylene repeating units. This functional group differs from the benzyl functional group in that benzyls have an extra CH₂. Category:Functional groups

Chemical compound

A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. For example, dihydrogen monoxide (water, ₂) is a compound composed of two hydrogen atoms for every oxygen atom. In general, this fixed ratio must be fixed due to some sort of physical property, rather than an arbitrary man-made selection. This is why materials such as brass, the superconductor YBCO, the semiconductor aluminium gallium arsenide, or chocolate are considered mixtures or alloys rather than compounds. A defining characteristic of a compound is that it has a chemical formula. Formulas describe the ratio of atoms in a substance, and the number of atoms in a single molecule of the substance (thus the formula for ethene is ₂₄ rather than ₂). The formula does not indicate that a compound is composed of molecules; for example, sodium chloride (table salt, ) is an ionic compound. Compounds may have a number of possible phases. Most compounds can exist as solids. Molecular compounds may also exist as liquids or gases. All compounds will decompose to smaller compounds or individual atoms if heated to a certain temperature (called the decomposition temperature). Every chemical compound that has been described in the literature carries a unique numerical identifier, its CAS number.

Types of compounds

- Acids
- Bases
- Ionic compounds
- Salts
- Oxides
- Organic compounds

Color

Color or colour is the perception of the frequency (or wavelength) of light, and can be compared to how pitch (or a musical note) is the perception of the frequency or wavelength of sound. It is a perception which in humans derives from the ability of the fine structures of the eye to distinguish (usually three) differently filtered analyses of a view. The perception of color is influenced by biology (some people are born seeing colors differently or not at all; see color blindness), long-term history of the observer, and also by short-term effects such as the colors nearby. (This is the basis of many optical illusions.) The science of color is sometimes called chromatics. It includes the perception of color by the human eye, the origin of color in materials, color theory in art, and the physics of color in the electromagnetic spectrum.

Physics of color

The colors of the visible light spectrum.

color	wavelength interval	frequency interval
red	~ 625-740 nm	~ 480-405 THz
orange	~ 590-625 nm	~ 510-480 THz
yellow	~ 565-590 nm	~ 530-510 THz
green	~ 500-565 nm	~ 600-530 THz
cyan	~ 485-500 nm	~ 620-600 THz
blue	~ 440-485 nm	~ 680-620 THz
violet	~ 380-440 nm	~ 790-680 THz
Continuous optical spectrum Image:Spectrum441pxWithnm.png Designed for monitors with gamma 1.5.
Computer "spectrum" Image:Computerspectrum.png The bars below show the relative intensities of the three colors mixed to make the color immediately above.

Color, frequency, and energy of light.

Color	$\lambda \,\!$ /nm	$\nu \,\!$ /10¹⁴ Hz	$\nu_b \,\!$ /10⁴ cm^-1	$E \,\!$ /eV	$E \,\!$ /kJ mol^-1
Infrared	>1000	<3.00	<1.00	<1.24	<120
Red	700	4.28	1.43	1.77	171
Orange	620	4.84	1.61	2.00	193
Yellow	580	5.17	1.72	2.14	206
Green	530	5.66	1.89	2.34	226
Blue	470	6.38	2.13	2.64	254
Violet	420	7.14	2.38	2.95	285
Near ultraviolet	300	10.0	3.33	4.15	400
Far ultraviolet	<200	>15.0	>5.00	>6.20	>598

Electromagnetic radiation is a mixture of radiation of different wavelengths and intensities. When this radiation has a wavelength inside the human visibility range (approximately from 380 nm to 740 nm), it is known as light within the (human) visible spectrum. The light's spectrum records each wavelength's intensity. The full spectrum of the incoming radiation from an object determines the visual appearance of that object, including its perceived color. As we will see, there are many more spectra than color sensations; in fact one may formally define a color to be the whole class of spectra which give rise to the same color sensation, although any such definition would vary widely among different species and also somewhat among individuals intraspecifically. A surface that diffusely reflects all wavelengths equally is perceived as white, while a dull black surface absorbs all wavelengths and does not reflect (for mirror reflection this is different: a proper mirror also reflects all wavelengths equally, but is not perceived as white, while shiny black objects do reflect). The familiar colors of the rainbow in the spectrum—named from the Latin word for appearance or apparition by Isaac Newton in 1671—contains all those colors that consist of visible light of a single wavelength only, the pure spectral or monochromatic colors. The frequencies are approximations and given in terahertz (THz). The wavelengths, valid in vacuum, are given in nanometers (nm). A list of other objects of similar size is available.

Important note

The color table should not be interpreted as a definite list – the pure spectral colors form a continuous spectrum, and how it is divided into distinct colors is a matter of taste and culture. Similarly, the intensity of a spectral color may alter its perception considerably; for example, a low-intensity orange-yellow is brown, and a low-intensity yellow-green is olive-green.

Spectral versus non-spectral colors

Most light sources are not pure spectral sources; rather they are created from mixtures of various wavelengths and intensities of light. To the human eye, however, there is a wide class of mixed-spectrum light that is perceived the same as a pure spectral color. In the table above, for instance, when your computer screen is displaying the "orange" patch, it is not emitting pure light at a fixed wavelength of around 600 nm (which is something most computer screens are unable to do). Rather, it is emitting a mixture of about two parts red to one part green light. Were you to print this page on a color printer, the orange patch on the paper, when lit with white light, would reflect yet another, more continuous spectrum. We cannot see those differences (although many animals can), and the reason has to do with the pigments that make up our color vision cells (see below). A useful quantification of this property is the dominant wavelength, which matches a wavelength of spectral light to a non-spectral source that evokes the same color perception. Dominant wavelength is the formal background for the popular concept of hue. In addition to the many light sources that can appear to be pure spectral colors but are actually mixtures, there are many color perceptions that by definition cannot be pure spectral colors due to desaturation or because they are purples (which are a mixture of red and violet light, from either end of the spectrum). Some examples of necessarily non-spectral colors are the achromatic colors (black, gray and white) and other colors such as pink, tan and magenta. See metamerism (color) for a basic introduction as to why color matching challenges exist.

Physical basis of color

A light wave can be analyzed as a superposition of sine waves, each of which has a specific frequency and wavelength. The eye gives limited information about the relative intensities of these sine waves (but not their phases — the eye is even more blind to phase than the ear, which can detect phase relationships of sounds only in certain very specific contexts). To understand which particular color perception will arise from a particular physical spectrum requires knowledge of the physiology of the retina. The human eye is also insensitive to polarization in most cases (though see Haidinger's brush), whereas some fish and mollusks can perceive it.

Color vision

Though the exact status of color is a matter of current philosophical dispute, color is arguably a psychophysical phenomenon that exists only in our minds. (See Qualia, for some of that dispute.) A "red" apple does not give off "red light", and it is misleading to think of things that we see, or of light itself, as objectively colored at all. Rather, the apple simply absorbs light of various wavelengths shining on it to different degrees, in such a way that the unabsorbed light which it reflects is perceived as red. An apple is perceived to be red only because normal human color vision perceives light with different mixes of wavelengths differently—and we have language to describe that difference. language In 1931, an international group of experts called the Commission Internationale d'Eclairage (CIE) developed a mathematical color model. The premise used by the CIE is that color is the combination of three things: a light source, an object, and an observer. The CIE tightly controlled each of these variables in an experiment that produced the measurements for the system. Although Aristotle and other ancient scientists speculated on the nature of light and color vision, it was not until Newton that light was correctly identified as the source of the color sensation. Goethe studied the theory of colors, and in 1801 Thomas Young proposed his trichromatic theory which was later refined by Hermann von Helmholtz. That theory was confirmed in the 1960s and will be described below. Hermann von Helmholtz The retina of the human eye contains three different types of color receptor cells, or cones. One type, relatively distinct from the other two, is most responsive to light that we perceive as violet, with wavelengths around 420 nm (cones of this type are sometimes called short-wavelength cones, S cones, or, most commonly but quite misleadingly, blue cones). The other two types are closely related genetically, chemically and in response. Each type is most responsive to light that we perceive as green or greenish. One of these types (sometimes called long-wavelength cones, L cones, or, misleadingly, red cones) is most sensitive to light we perceive as yellowish-green, with wavelengths around 564 nm; the other type (sometimes called middle-wavelength cones, M cones, or misleadingly green cones) is most sensitive to light perceived as green, with wavelengths around 534 nm. The term "red cones" for the long-wavelength cones is deprecated as this type is actually maximally responsive to light we perceive as greenish, albeit longer wavelength light than that which maximally excites the mid-wavelength/"green" cones. The sensitivity curves of the cones are roughly bell-shaped, and overlap considerably. The incoming signal spectrum is thus reduced by the eye to three values, sometimes called tristimulus values, representing the intensity of the response of each of the cone types. Because of the overlap between the sensitivity ranges, some combinations of responses in the three types of cone are impossible no matter what light stimulation is used. For example, it is not possible to stimulate only the mid-wavelength/"green" cones: the other cones must be stimulated to some degree at the same time, even if light of some single wavelength is used (including that to which the target cones are maximally sensitive). The set of all possible tristimulus values determines the human color space. It has been estimated that humans can distinguish roughly 10 million different colors, although the identification of a specific color is highly subjective, since even the two eyes of a single individual perceive colors slightly differently. This is discussed in more detail below. The rod system (which vision in very low light relies on exclusively) does not by itself sense differences in wavelength; therefore it is not normally implicated in color vision. But experiments have conclusively shown that in certain marginal conditions a combination of rod stimulation and cone stimulation can result in color discriminations not based on the mechanisms described above. While the mechanisms of color vision at the level of the cones in the retina are well described in terms of tristimulus values (see above), color processing and perception above that base level are organized differently. A dominant theory of the higher neural mechanisms of color vision proposes three opponent processes, or opponent channels, constructed out of the raw input from the cones: a red-green channel, a blue-yellow channel, and a black-white ("luminance") channel. This theory tries to account for the structure of our subjective color experience (see discussion below). Blue and yellow are considered complementary colors, or opposites: you could not experience a bluish yellow (or a greenish red), any more than you could experience a dark brightness or a hot coldness. The four "polar" colors proposed as extremes in the two opponent processes other than black-white have some natural claim to being called primary colors. This is in competition with various sets of three primary colors proposed as "generators" of all normal human color experience (see below).

Clinical issues

If one or more types of a person's color-sensing cones are missing or less responsive than normal to incoming light, that person has a smaller or skewed color space and is said to be color deficient. Another term frequently used is color blind, although this can be misleading; only a small fraction of color deficient individuals actually see completely in black and white, and most simply have anomalous color perception. Some kinds of color deficiency are caused by anomalies in the number or nature of cones of the various types, as just described. Others (like central or cortical achromatopsia) are caused by neural anomalies in those parts of the brain where visual processing takes place. Some animals may have more than three different types of color receptor (most marsupials, birds, reptiles, and fish; see tetrachromat, below) or fewer (most mammals; these are called dichromats and monochromats). Humans and other old-world primates are actually rather unusual in possessing three kinds of receptors. An unusual and elusive neurological condition sometimes affecting color perception is synaesthesia.

Tetrachromat

A normal human is a trichromat (from Greek: tri=three, chroma=color). In theory it may be possible for a person to have four, rather than three, distinct types of cone cell. If these four types are sufficiently distinct in spectral sensitivity and the neural processing of the input from the four types is developed, a person may be a tetrachromat (tetra=four). Such a person might have an extra and slightly different copy of either the medium- or long-wave cones. It is not clear whether such people exist or that the human brain could actually process the information from such an extra cone type separately from the standard three. However, strong evidence suggests that such people do exist, they are all female by genetic imperative, and their brains gladly adapt to use the additional information. For many species, tetrachromacy is the normal case, although the cone cells of animal tetrachromats have a very different (more evenly-spaced) spectral sensitivity distribution than those of possible human tetrachromats.

Color perception

There is an interesting phenomenon which occurs when an artist uses a limited color palette: the eye tends to compensate by seeing any grey or neutral color as the color which is missing from the color wheel. E.g.: in a limited palette consisting of red, yellow, black, and white, a mixture of yellow and black will appear as a variety of green, a mixture of red and black will appear as a variety of purple, and pure grey will appear bluish. When the eye shifts attention after viewing a color for some time, then an afterimage of the complement of that color (the color opposite to it in the color wheel) is perceived by the eye for some time wherever it moves. This effect of color perception was utilised by Vincent van Gogh, a Post-Impressionist painter.

Effect of luminosity

Note that the color experience of a given light mixture may vary with absolute luminosity, because both rods and cones are active at once in the eye, with each having different color curves, and rods taking over gradually from cones as the brightness of the scene is reduced. This effect leads to a change in color rendition with absolute illumination levels that can be summarised in the "Kruithof curve".

Cultural influences

Different cultures have different terms for colors, and may also assign some color names to slightly different parts of the spectrum, or have a different color ontology: for instance, the Han character 青 (pronounced qīng in Mandarin and aoi in Japanese) has a meaning that covers both blue and green; blue and green are traditionally considered shades of 青; In more contemporary terms, they are 藍 (lán) and 綠 (lǜ) respectively. Similarly, languages are selective when deciding which hues are split into different colors on the basis of how light or dark they are. Apart from the black-grey-white continuum, English splits some hues into several distinct colors according to lightness: such as red and pink or orange and brown. To English speakers, these pairs of colors, which are objectively no more different that light green and dark green, are conceived as totally different. An Italian will make the same red-pink and orange-brown distinctions, but will also make a further distinction between blu and azzurro, which English speakers would simply call dark and light blue. To Italian speakers, blu and azzurro are as separate as red and pink or orange and brown. Color terms evolve. It is argued that there are a limited number of universal "basic color terms" which begin to be used by individual cultures in a relatively fixed order. For example, a culture would start with only two terms, meaning roughly 'dark' (covering black, dark colors and cold colors such as blue ) and 'bright' (covering white, light colors and warm colors such as red), before adding more specific color names, in the order of red; green and/or yellow; blue; brown; and orange, pink, purple, and/or gray. Older arguments for this theory also stipulated that the acquisition and use of basic color terms further along the evolutionary order indicated a more complex culture with more highly developed technology. A somewhat dated example of a universal color categories theory is Basic Color Terms: Their Universality and Evolution (1969) by Brent Berlin and Paul Kay. A more recent example of a linguistic determinism theory might be Is color categorisation universal? New evidence from a stone-age culture (1999) by Jules Davidoff et al. The idea of linguistically determined color categories is often used as evidence for the Sapir-Whorf hypothesis (Language, Thought, and Reality (1956) by Benjamin Lee Whorf). Additionally, different colors are often associated with different emotional states, values, or groups, but these associations can vary between cultures. In one system, red is considered to motivate action; orange and purple are related to spirituality; yellow cheers; green creates cosiness and warmth; blue relaxes; and white is associated with either purity or death. These associations are described more fully in the individual color pages, and under color psychology. See also: National colors

Color constancy

The trichromatric theory discussed above is strictly true only if the whole scene seen by the eye is of one and the same color, which of course is unrealistic. In reality, the brain compares the various colors in a scene, in order to eliminate the effects of the illumination. If a scene is illuminated with one light, and then with another, as long as the difference between the light sources stays within a reasonable range, the colors of the scene will nevertheless appear constant to us. This was discovered by Edwin Land in the 1970s and led to his retinex theory of color constancy.

Contrast

Note: the following comparison requires an all-digital display setup (commonly, a laptop or DVI-connected LCD) to avoid errors caused by an unfortunate interaction between frequency response and gamma curves. Compare the visibility of the RGB primary and secondary colors against a white background:

red

green

blue

red+green

green+blue

red+blue

red+green+blue

zero light

Again, compare variations on gray backgrounds—#7f7f7f, #5f5f5f & #9f9f9f—the eight RGB primaries are equidistant from #7f7f7f in a 3-d geometrical representation of RGB color space—a reminder of the importance of background color for color perception. Background = #7f7f7f

red

green

blue

red+green

green+blue

red+blue

red+green+blue

zero light

And let's look at black again, for completeness. (Note that your monitor background probably is not perfectly black, as you can see by switching off the monitor.) Background = #000000

red

green

blue

red+green

green+blue

red+blue

red+green+blue

zero light

Measurement and reproduction of color

monitor Two different light spectra which have the same effect on the three color receptors in the human eye will be perceived as the same color. This is exemplified by the white light that is emitted by fluorescent lamps, which typically has a spectrum consisting of a few narrow bands, while daylight has a continuous spectrum. The human eye cannot tell the difference between such light spectra just by looking into the light source, although reflected colors from objects can look different. (This is often exploited e.g. to make fruit or tomatoes look more brightly red in shops.) Similarly, most human color perceptions can be generated by a mixture of three colors called primaries. This is used to reproduce color scenes in photography, printing, television, and other media. There are a number of methods or color spaces for specifying a color in terms of three particular primary colors. Each method has its advantages and disadvantages depending on the particular application. No mixture of colors, though, can produce a fully pure color perceived as completely identical to a spectral color, although one can get very close for the longer wavelengths, where the chromaticity diagram above has a nearly straight edge. For example, mixing green light (530 nm) and blue light (460 nm) produces cyan light that is slightly desaturated, because response of the red color receptor would be greater to the green and blue light in the mixture than it would be to a pure cyan light at 485 nm that has the same intensity as the mixture of blue and green. Because of this, and because the primaries in color printing systems generally are not pure themselves, the colors reproduced are never perfectly saturated colors, and so spectral colors cannot be matched exactly. However, natural scenes rarely contain fully saturated colors, thus such scenes can usually be approximated well by these systems. The range of colors that can be reproduced with a given color reproduction system is called the gamut. The CIE chromaticity diagram can be used to describe the gamut. Another problem with color reproduction systems is connected with the acquisition devices, like cameras or scanners. The characteristics of the color s