buta-1,3-diene
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1,3-Butadiene () is the
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to
synthetic rubber A synthetic rubber is an artificial elastomer. They are polymers synthesized from petroleum byproducts. About 32-million metric tons of rubbers are produced annually in the United States, and of that amount two thirds are synthetic. Synthetic rubb ...
. The molecule can be viewed as the union of two
vinyl group In organic chemistry, a vinyl group (abbr. Vi; IUPAC name: ethenyl group) is a functional group with the formula . It is the ethylene (IUPAC name: ethene) molecule () with one fewer hydrogen atom. The name is also used for any compound contai ...
s. It is the simplest
conjugated diene In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclatur ...
. Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from
motor vehicle A motor vehicle, also known as motorized vehicle or automotive vehicle, is a self-propelled land vehicle, commonly wheeled, that does not operate on rails (such as trains or trams) and is used for the transportation of people or cargo. The ...
s. The name butadiene can also refer to the
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Is ...
, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This
allene In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon centres (). Allenes are classified as cumulated dienes. The parent compound of this class is propadiene, which ...
has no industrial significance.


History

In 1863, the French chemist E. Caventou isolated butadiene from the
pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements '' ...
of
amyl alcohol An amyl alcohol is any of eight alcohols with the formula C5H12O. A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterification, by which is produced amyl acetate ...
. This hydrocarbon was identified as butadiene in 1886, after
Henry Edward Armstrong Henry Edward Armstrong FRS FRSE (Hon) (6 May 1848 – 13 July 1937) was a British chemist. Although Armstrong was active in many areas of scientific research, such as the chemistry of naphthalene derivatives, he is remembered today largely for h ...
isolated it from among the pyrolysis products of petroleum. In 1910, the Russian chemist Sergei Lebedev polymerized butadiene and obtained a material with rubber-like properties. This polymer was, however, found to be too soft to replace natural rubber in many applications, notably automobile tires. The butadiene industry originated in the years leading up to World War II. Many of the belligerent nations realized that in the event of war, they could be cut off from rubber plantations controlled by the
British Empire The British Empire was composed of the dominions, colonies, protectorates, mandates, and other territories ruled or administered by the United Kingdom and its predecessor states. It began with the overseas possessions and trading posts e ...
, and sought to reduce their dependence on natural rubber. In 1929, Eduard Tschunker and
Walter Bock Walter Bock (20 January 1895 – 25 October 1948)Death record Nr. 3271/Köln I for Ludwig Walter Robert Bock of Oct. 26, 1948, Landesarchiv NRW, Duisburg was a German chemist who developed styrene-butadiene copolymer by emulsion polymerization ...
, working for
IG Farben Interessengemeinschaft Farbenindustrie AG (), commonly known as IG Farben (German for 'IG Dyestuffs'), was a German chemical and pharmaceutical conglomerate. Formed in 1925 from a merger of six chemical companies— BASF, Bayer, Hoechst, Agf ...
in Germany, made a copolymer of
styrene Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...
and butadiene that could be used in automobile tires. Worldwide production quickly ensued, with butadiene being produced from
grain alcohol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a hyd ...
in the Soviet Union and the United States, and from coal-derived
acetylene Acetylene ( systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...
in Germany.


Production


Extraction from C4 hydrocarbons

In the United States, western Europe, and Japan, butadiene is produced as a byproduct of the
steam cracking Steam cracking is a petrochemical process in which saturated hydrocarbons are broken down into smaller, often unsaturated, hydrocarbons. It is the principal industrial method for producing the lighter alkenes (or commonly olefins), including et ...
process used to produce
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene ...
and other
alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic ...
s. When mixed with steam and briefly heated to very high temperatures (often over 900 °C), aliphatic hydrocarbons give up hydrogen to produce a complex mixture of unsaturated hydrocarbons, including butadiene. The quantity of butadiene produced depends on the hydrocarbons used as feed. Light feeds, such as
ethane Ethane ( , ) is an organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petroc ...
, give primarily
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene ...
when cracked, but heavier feeds favor the formation of heavier olefins, butadiene, and
aromatic hydrocarbon Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past groupin ...
s. Butadiene is typically isolated from the other four-carbon
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
s produced in steam cracking by extractive distillation using a
polar aprotic solvent A polar aprotic solvent is a solvent that lacks an acidic proton and is polar. Such solvents lack hydroxyl and amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Am ...
such as
acetonitrile Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula and structure . This colourless liquid is the simplest organic nitrile ( hydrogen cyanide is a simpler nitrile, but the cyanide anion is not clas ...
, ''N''-methyl-2-pyrrolidone,
furfural Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occur ...
, or
dimethylformamide Dimethylformamide is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...
, from which it is then stripped by
distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the he ...
.Sun, H.P. Wristers, J.P. (1992). Butadiene. In J.I. Kroschwitz (Ed.), ''Encyclopedia of Chemical Technology, 4th ed.'', vol. 4, pp. 663–690. New York: John Wiley & Sons.


From dehydrogenation of ''n''-butane

Butadiene can also be produced by the catalytic
dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. A ...
of normal butane (''n''-butane). The first such post-war commercial plant, producing 65,000
ton Ton is the name of any one of several units of measure. It has a long history and has acquired several meanings and uses. Mainly it describes units of weight. Confusion can arise because ''ton'' can mean * the long ton, which is 2,240 pounds ...
s per year of butadiene, began operations in 1957 in
Houston Houston (; ) is the most populous city in Texas, the most populous city in the Southern United States, the fourth-most populous city in the United States, and the sixth-most populous city in North America, with a population of 2,304,580 ...
, Texas.Beychok, M.R. and Brack, W.J., "First Postwar Butadiene Plant", ''Petroleum Refiner'', June 1957. Prior to that, in the 1940s the
Rubber Reserve Company Kenneth Stanley "Boots" Adams (August 31, 1899 – March 30, 1975) was an American business executive, University of Kansas booster, and civic philanthropist of Bartlesville, Oklahoma. Adams began his career with the Phillips Petroleum Company i ...
, a part of the United States government, constructed several plants in
Borger, Texas Borger ( ) is the largest city in Hutchinson County, Texas, United States. The population was 12,551 at the 2020 census. Borger is named for businessman Asa Philip "Ace" Borger, who also established the Hutchinson County seat of Stinnett ...
,
Toledo, Ohio Toledo ( ) is a city in and the county seat of Lucas County, Ohio, United States. A major Midwestern United States port city, Toledo is the fourth-most populous city in the state of Ohio, after Columbus, Cleveland, and Cincinnati, and according ...
, and El Segundo, California, to produce synthetic rubber for the war effort as part of the United States Synthetic Rubber Program.Herbert, Vernon, "Synthetic Rubber: A Project That Had to Succeed", Greenwood Press, 1985, Total capacity was 68 KMTA (Kilo Metric Tons per Annum). Today, butadiene from ''n''-butane is commercially produced using the Houdry Catadiene process, which was developed during World War II. This entails treating butane over alumina and
chromia In Greek mythology, Chromia (; Ancient Greek: , ''Khrōmía'') was the daughter of Itonus, son of Amphictyon, himself son of Deucalion. She was also, in some traditions, the mother of Aetolus, Paeon, Epeius and Eurycyda by Endymion. The poem ''E ...
at high temperatures.


From ethanol

In other parts of the world, including South America, Eastern Europe, China, and India, butadiene is also produced from
ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
. While not competitive with steam cracking for producing large volumes of butadiene, lower capital costs make production from ethanol a viable option for smaller-capacity plants. Two processes were in use. In the single-step process developed by Sergei Lebedev, ethanol is converted to butadiene, hydrogen, and water at 400–450 °C over any of a variety of metal oxide catalysts:Kirshenbaum, I. (1978). Butadiene. In M. Grayson (Ed.), ''Encyclopedia of Chemical Technology, 3rd ed.'', vol. 4, pp. 313–337. New York: John Wiley & Sons. : This process was the basis for the
Soviet Union The Soviet Union,. officially the Union of Soviet Socialist Republics. (USSR),. was a List of former transcontinental countries#Since 1700, transcontinental country that spanned much of Eurasia from 1922 to 1991. A flagship communist state, ...
's synthetic rubber industry during and after World War II, and it remained in limited use in Russia and other parts of eastern Europe until the end of the 1970s. At the same time this type of manufacture was canceled in Brazil. As of 2017, no butadiene was produced industrially from ethanol. In the other, two-step process, developed by the Russian emigre chemist Ivan Ostromislensky, ethanol is
oxidized Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...
to acetaldehyde, which reacts with additional ethanol over a
tantalum Tantalum is a chemical element with the symbol Ta and atomic number 73. Previously known as ''tantalium'', it is named after Tantalus, a villain in Greek mythology. Tantalum is a very hard, ductile, lustrous, blue-gray transition metal that ...
-promoted porous
silica Silicon dioxide, also known as silica, is an oxide of silicon with the chemical formula , most commonly found in nature as quartz and in various living organisms. In many parts of the world, silica is the major constituent of sand. Silica is ...
catalyst at 325–350 °C to yield butadiene: : This process was one of the three used in the United States to produce "government rubber" during World War II, although it is less economical than the butane or butene routes for the large volumes. Still, three plants with a total capacity of 200,000 tons per year were constructed in the U.S. (
Institute, West Virginia Institute is an unincorporated community on the Kanawha River in Kanawha County, West Virginia, United States. Interstate 64 and West Virginia Route 25 pass by the community, which has grown to intermingle with nearby Dunbar. As of 2018, the commu ...
,
Louisville, Kentucky Louisville ( , , ) is the largest city in the Commonwealth of Kentucky and the 28th most-populous city in the United States. Louisville is the historical seat and, since 2003, the nominal seat of Jefferson County, on the Indiana border ...
, and Kobuta, Pennsylvania) with start-ups completed in 1943, the Louisville plant initially created butadiene from acetylene generated by an associated calcium carbide plant. The process remains in use today in China and India.


From butenes

1,3-Butadiene can also be produced by
catalytic Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. A ...
of normal
butene Butene, also known as butylene, is an alkene with the formula . The word ''butene'' may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for ...
s. This method was also used by the U.S. Synthetic Rubber Program (USSRP) during
World War II World War II or the Second World War, often abbreviated as WWII or WW2, was a world war that lasted from 1939 to 1945. It involved the vast majority of the world's countries—including all of the great powers—forming two opposing ...
. The process was much more economical than the alcohol or n-butane route but competed with
aviation gasoline Avgas (aviation gasoline, also known as aviation spirit in the UK) is an aviation fuel used in aircraft with spark-ignited internal combustion engines. ''Avgas'' is distinguished from conventional gasoline (petrol) used in motor vehicles, whi ...
for available butene molecules (butenes were plentiful thanks to catalytic cracking). The USSRP constructed several plants in Baton Rouge and
Lake Charles, Louisiana Lake Charles (French: ''Lac Charles'') is the fifth-largest incorporated city in the U.S. state of Louisiana, and the parish seat of Calcasieu Parish, located on Lake Charles, Prien Lake, and the Calcasieu River. Founded in 1861 in Calcas ...
;
Houston Houston (; ) is the most populous city in Texas, the most populous city in the Southern United States, the fourth-most populous city in the United States, and the sixth-most populous city in North America, with a population of 2,304,580 ...
, Baytown, and
Port Neches, Texas Port Neches is a city in Jefferson County, Texas, United States. The population was 13,692 at the 2020 census, up from 13,040 at the 2010 census. It is part of the Beaumont–Port Arthur metropolitan area. History The area known as Port Neche ...
; and
Torrance, California Torrance is a city in the Los Angeles metropolitan area located in Los Angeles County, California, United States. The city is part of what is known as the South Bay region of the metropolitan area. Torrance has of beachfront on the Pacific O ...
. Total annual production was 275 KMTA. In the 1960s, a
Houston Houston (; ) is the most populous city in Texas, the most populous city in the Southern United States, the fourth-most populous city in the United States, and the sixth-most populous city in North America, with a population of 2,304,580 ...
company known as "Petro-Tex" patented a process to produce butadiene from normal
butene Butene, also known as butylene, is an alkene with the formula . The word ''butene'' may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for ...
s by oxidative
dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. A ...
using a proprietary catalyst. It is unclear if this technology is practiced commercially. After World War II, the production from butenes became the major type of production in USSR.


For laboratory use

1,3-Butadiene is inconvenient for laboratory use because it is gas. Laboratory procedures have been optimized for its generation from nongaseous precursors. It can be produced by the retro- Diels-Alder reaction of
cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light a ...
. Sulfolene is a convenient solid storable source for 1,3-butadiene in the laboratory. It releases the diene and sulfur dioxide upon heating.


Uses

Most butadiene is used to make synthetic rubbers for the manufacture of tyres, grommets and elastic bands. The conversion of butadiene to synthetic rubbers is called
polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many fo ...
, a process by which small molecules (monomers) are linked to make large ones (polymers). The mere polymerization of butadiene gives polybutadiene, which is a very soft, almost liquid material. The polymerization of butadiene ''and'' other monomers gives
copolymer In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...
s, which are more valued. The polymerization of butadiene and
styrene Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...
and/or
acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecula ...
, such as acrylonitrile butadiene styrene (ABS), nitrile-butadiene (NBR), and
styrene-butadiene Styrene-butadiene or styrene-butadiene rubber (SBR) describe families of synthetic rubbers derived from styrene and butadiene (the version developed by Goodyear is called Neolite). These materials have good abrasion resistance and good aging st ...
(SBR). These copolymers are tough and/or elastic depending on the ratio of the monomers used in their preparation. SBR is the material most commonly used for the production of automobile tyres. Precursors to still other synthetic rubbers are prepared from butadiene. One is
chloroprene Chloroprene is the common name for 2-chlorobuta-1,3-diene (IUPAC name) with the chemical formula CH2=CCl−CH=CH2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene ...
. Smaller amounts of butadiene are used to make
adiponitrile Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.M. T. Musser, "Adip ...
, a precursor to some nylons. The conversion of butadiene to adiponitrile entails the addition of hydrogen cyanide to each of the double bonds in butadiene. The process is called
hydrocyanation In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of ...
. Butadiene is used to make the solvent sulfolane. Butadiene is also useful in the synthesis of
cycloalkanes In organic chemistry, the cycloalkanes (also called naphthenes, but distinct from naphthalene) are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing ...
and cycloalkenes, as it reacts with double and triple carbon-carbon bonds through Diels-Alder reactions. The most widely used such reactions involve reactions of butadiene with one or two other molecules of butadiene, i.e., dimerization and trimerization respectively. Via dimerizatiion butadiene is converted to 4-vinylcyclohexene and cyclooctadiene. In fact, vinylcyclohexene is a common impurity that accumulates when butadiene is stored. Via trimerization, butadiene is converted to cyclododecatriene. Some of these processes employ nickel- or titanium-containing catalysts.


Structure, conformation, and stability

The most stable
conformer Conformer is a clear acrylic shell fitted after an enucleation if the final artificial eye is not available at the time of surgery to hold the shape of the eye socket and allow the eyelids to blink over the shell without rubbing the suture line. ...
of 1,3-butadiene is the ''s''-''trans'' conformation, in which the molecule is planar, with the two pairs of double bonds facing opposite directions. This conformation is most stable because orbital overlap between double bonds is maximized, allowing for maximum conjugation, while steric effects are minimized. Conventionally, the ''s-trans'' conformation is considered to have a C2-C3 dihedral angle of 180°. In contrast, the ''s''-''cis'' conformation, in which the dihedral angle is 0°, with the pair of double bonds facing the same direction is approximately 16.5 kJ/mol (3.9 kcal/mol) higher in energy, due to steric hindrance. This geometry is a local energy maximum, so in contrast to the ''s-trans'' geometry, it is not a conformer. The ''gauche'' geometry, in which the double bonds of the ''s-cis'' geometry are twisted to give a dihedral angle of around 38°, is a second conformer that is around 12.0 kJ/mol (2.9 kcal/mol) higher in energy than the ''s-trans'' conformer. Overall, there is a barrier of 24.8 kJ/mol (5.9 kcal/mol) for isomerization between the two conformers. This increased rotational barrier and strong overall preference for a near-planar geometry is evidence for a delocalized π system and a small degree of partial double bond character in the C–C single bond, in accord with resonance theory. Despite the high energy of the ''s-cis'' conformation, 1,3-butadiene needs to assume this conformation (or one very similar) before it can participate as the four-electron component in concerted cycloaddition reactions like the Diels-Alder reaction. Similarly, a combined experimental and computational study has found that the double bond of ''s-trans-''butadiene has a length of 133.8 pm, while that for ethylene has a length of 133.0 pm. This was taken as evidence of a π-bond weakened and lengthened by delocalization, as depicted by the resonance structures shown below. A qualitative picture of the
molecular orbital In chemistry, a molecular orbital is a mathematical function describing the location and wave-like behavior of an electron in a molecule. This function can be used to calculate chemical and physical properties such as the probability of findin ...
s of 1,3-butadiene is readily obtained by applying Hückel theory. (The article on Hückel theory gives a derivation for the butadiene orbitals.) 1,3-Butadiene is also thermodynamically stabilized. While a monosubstituted double bond releases about 30.3 kcal/mol of heat upon hydrogenation, 1,3-butadiene releases slightly less (57.1 kcal/mol) than twice this energy (60.6 kcal/mol), expected for two isolated double bonds. That implies a stabilization energy of 3.5 kcal/mol. Similarly, the hydrogenation of the terminal double bond of 1,4-pentadiene releases 30.1 kcal/mol of heat, while hydrogenation of the terminal double bond of conjugated (''E'')-1,3-pentadiene releases only 26.5 kcal/mol, implying a very similar value of 3.6 kcal/mol for the stabilization energy. The ~3.5 kcal/mol difference in these heats of hydrogenation can be taken to be the resonance energy of a conjugated diene.


Reactions

The industrial uses illustrate the tendency of butadiene to polymerize. Its susceptibility to 1,4-addition reactions is illustrated by its hydrocyanation. Like many dienes, it undergoes Pd-catalyzed reactions that proceed via allyl complexes. It is a partner in Diels-Alder reactions, e.g. with maleic anhydride to give
tetrahydrophthalic anhydride Tetrahydrophthalic anhydride is an organic compound with the formula C6H8C2O3. The compound exists as two isomers, this article being focused on the more common cis isomer. It is a precursor to other compounds including the dicarboxylic acid tetr ...
. Like other dienes, butadiene is a ligand for low-valent metal complexes, e.g. the derivatives Fe(butadiene)(CO)3 and Mo(butadiene)3.


Environmental health and safety

Butadiene is of low acute toxicity.
LC50 In toxicology, the median lethal dose, LD50 (abbreviation for " lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is ...
is 12.5–11.5 vol% for inhalation by rats and mice. Long-term exposure has been associated with cardiovascular disease. There is a consistent association with leukemia, as well as a significant association with other cancers. IARC has designated 1,3-Butadiene as a
Group 1 Group 1 may refer to: * Alkali metal, a chemical element classification for Alkali metal * Group 1 (racing), a historic (until 1981) classification for Touring car racing, applied to standard touring cars. Comparable to modern FIA Group N * Group On ...
carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...
('carcinogenic to humans'), and the Agency for Toxic Substances Disease Registry and the US EPA also list the chemical as a carcinogen.Health Effects https://www.osha.gov/SLTC/butadiene/index.html The American Conference of Governmental Industrial Hygienists (ACGIH) lists the chemical as a suspected carcinogen. The Natural Resource Defense Council (NRDC) lists some disease clusters that are suspected to be associated with this chemical. Some researchers have concluded it is the most potent carcinogen in cigarette smoke, twice as potent as the runner up
acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecula ...
1,3-Butadiene is also a suspected human teratogen. Prolonged and excessive exposure can affect many areas in the human body; blood, brain, eye, heart, kidney, lung, nose and throat have all been shown to react to the presence of excessive 1,3-butadiene. Animal data suggest that women have a higher sensitivity to possible carcinogenic effects of butadiene over men when exposed to the chemical. This may be due to estrogen receptor impacts. While these data reveal important implications to the risks of human exposure to butadiene, more data are necessary to draw conclusive risk assessments. There is also a lack of human data for the effects of butadiene on reproductive and development shown to occur in mice, but animal studies have shown breathing butadiene during pregnancy can increase the number of birth defects, and humans have the same hormone systems as animals.EPA website
/ref> 1,3-Butadiene is recognized as a Highly Reactive Volatile Organic Compound (HRVOC) for its potential to readily form
ozone Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lo ...
, and as such, emissions of the chemical are highly regulated by TCEQ in parts of the Houston-Brazoria-Galveston Ozone Non-Attainment Areabr>


Data sheet


See also

*
Cyclobutadiene Cyclobutadiene is an organic compound with the formula . It is very reactive owing to its tendency to dimerize. Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is ...
* Polybutadiene * Hydroxyl-terminated polybutadiene


References


External links


1,3-Butadiene
– Agency for Toxic Substances and Disease Registry

– CDC - NIOSH Pocket Guide to Chemical Hazards

{{DEFAULTSORT:Butadiene, 1, 3- Alkadienes Hazardous air pollutants Monomers IARC Group 1 carcinogens U.S. Synthetic Rubber Program Commodity chemicals Petrochemicals Conjugated dienes