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Encyclopedia > Butadiene
Butadiene
CH2=CH-CH=CH2
General
Systematic name 1,3-butadiene
Other names biethylene, erythrene,
divinyl, vinylethylene
Molecular formula C4H6
SMILES C=CC=C
Molar mass 50.09 g/mol
Appearance colourless gas
CAS number [106-99-0]
Properties
Density and phase 0.64 g/cm3, liquid
Solubility in water  ? g/100 ml (? °C)
Melting point -108.9 °C (164.3 K)
Boiling point -4.4 °C (268.8 K)
Structure
Molecular shape  ?
Coordination geometry  ?
Crystal structure  ?
Dipole moment  ? D
Hazards
MSDS External MSDS
Main hazards Flammable, Irritative
Flash point -85 °C
R/S statement R: ? S: ?
RTECS number  ?
Supplementary data page
Structure & properties n, εr, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related alkene/diene 1,2-butadiene,
isoprene,
chloroprene
Related compounds
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

Butadiene can refer to either one of two hydrocarbon chemical compounds which are alkenes that are isomers of each other. They are both dienes having the chemical formula C4H6 and are both gases at room temperature and pressure. IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII alpha-numeric strings. ... Molar mass is the mass of one mole of an element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... A substance is soluble in a fluid if it dissolves in the fluid. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change state from a liquid to a gas throughout the bulk of the liquid. ... In chemistry, hybridisation is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... The coordination geometry of an atom is the geometrical pattern formed by its neighbors in a molecule or a crystal. ... Rose des Sables (Sand Rose), formed of gypsum crystals In mineralogy and crystallography, a crystal structure is a unique arrangement of atoms in a crystal. ... A dipole (Greek: dyo = two and polos = pivot) is a pair of electric charges or magnetic poles of equal magnitude but opposite polarity (opposite electronic charges), separated by some (usually small) distance. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... ... Worker safety and health is the prevention and reduction of the number of occupational safety and health hazards at the places of employment, providing safe and healthful working conditions. ... There is a live album by the Rolling Stones called Flashpoint The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... ... ... The refractive index of a material is the factor by which the phase velocity of electromagnetic radiation is slowed relative to vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... ... ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Mass spectrometry is a technique for separating ions by their mass-to-charge (m/z) ratios. ... An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon-carbon double bond. ... Dienes are hydrocarbons which contain two double bonds. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... Chemical Structure of Chloroprene Chloroprene is the common name for the organic compound 2-chloro-1,3-butadiene, which has the chemical formula C4H5Cl. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... // Definition In chemistry, a hydrocarbon is any chemical compound that consists only of carbon (C) and hydrogen (H). ... ... An alkene in organic chemistry is an unsaturated hydrocarbon containing at least one carbon-carbon double bond. ... In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ... Dienes are hydrocarbons which contain two double bonds. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... A gas is one of the phases of matter. ... Temperature is the physical property of a system which underlies the common notions of hot and cold; the material with the higher temperature is said to be hotter. ... Pressure is the application of force to a surface, and the concentration of that force in a given area. ...


1,3-butadiene is a simple conjugated diene having the chemical structure shown at right. It is an important industrial chemical used as a monomer in the production of synthetic rubber. When the word butadiene is used, most of the time it refers to 1,3-butadiene. In linguistics, grammatical conjugation is the creation of derived forms of a verb from the word root by inflection (regular alteration according to rules of grammar). ... In chemistry, a monomer (from Greek mono one and meros part) is a small molecule that may become chemically bonded to other monomers to form a polymer. ... Synthetic rubber is a type of artificially-made polymer material which acts as an elastomer. ...


The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene. However, this allene is difficult to prepare and has no industrial significance. The remainder of this article concerns 1,3-butadiene. Dienes are hydrocarbons which contain two double bonds. ... Propyl allene is the simplest allene. ...

Contents


History

Throughout the later 19th century, many chemists attempted to determine the makeup of natural rubber, with the goal of reproducing it. In 1860, the British chemist Charles Greville Williams analyzed rubber by destructive distillation and obtained a large quantity of a light oil which he termed isoprene. In 1873, the French chemist Georges Bouchardat found that isoprene, when heated with hydrochloric acid for several hours, produced a rubber-like substance. Alternative meaning: Nineteenth Century (periodical) (18th century — 19th century — 20th century — more centuries) As a means of recording the passage of time, the 19th century was that century which lasted from 1801-1900 in the sense of the Gregorian calendar. ... 1860 is the leap year starting on Sunday. ... Look up chemist on Wiktionary, the free dictionary. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... 1873 was a common year starting on Wednesday (see link for calendar). ... The chemical substance hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride (HCl) gas. ...


In 1882, another British chemist Sir William Augustus Tilden distilled isoprene from turpentine. Tilden found a number of ways to prepare rubber materials from isoprene, but none were commercially practical, and so by the 1890s he abandoned synthetic rubber research. 1882 was a common year starting on Sunday (see link for calendar). ... Turpentine is a fluid obtained by distillation from resin obtained from trees, mainly various species of pine (Pinus). ... The 1890s were sometimes referred to as the Mauve Decade, because William Henry Perkins aniline dye allowed the widespread use of that colour in fashion, and also as the Gay Nineties, under the then-current usage of the word gay which referred simply to merriment and frivolity, with no...


Before doing so, however, Tilden determined the structure of isoprene, opening the door to producing rubbers from chemicals with similar structures, the simplest of which is butadiene. In 1910, the Russian chemist Sergey Lebedev prepared a butadiene polymer with rubber-like properties. This polymer was, however, too soft to replace natural rubber in many roles, especially automobile tires. 1910 was a common year starting on Saturday (see link for calendar). ...


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, and sought to remove their dependence on natural rubber. In 1929, Eduard Tschunker and Walter Bock, working for I.G. Farben in Germany, made a copolymer of styrene and butadiene that could be used in automobile tires. Worldwide production quickly ensued, with butadiene being produced from grain alcohol in the Soviet Union and the United States and from coal-derived acetylene in Germany. World War II was a truly global conflict with many facets: immense human suffering, fierce indoctrinations, and the use of new, extremely devastating weapons such as the atom bomb World War II, also known as the Second World War, was a mid-20th-century conflict that engulfed much of the... The British Empire in 1897, marked in pink, the traditional colour for Imperial British dominions on maps The British Empire was the worlds global power for some time , a product of the European Age of Exploration that began with the global maritime empires of Portugal and Spain in the... 1929 was a common year starting on Tuesday (link will take you to calendar). ... IG Farben (short for Interessen-Gemeinschaft Farbenindustrie AG) was a German conglomerate of companies formed in 1925 and even earlier during World War I. IG Farben held nearly a total monopoly on the chemical production, later during the time of Nazi Germany. ... Styrene (also vinyl benzene, ethenylbenzene, phenethylene, cinnamene, diarex HF 77, styrolene, styrol, styropol) is an organic compound which is an aromatic hydrocarbon having the chemical formula C8H8. ... A small variety of cars, the most popular kind of automobile. ... Firestone tire A tire (U.S. spelling) or tyre (UK spelling) is a roughly toroidal piece of material placed on the circumference of a wheel, either for the purpose of cushioning or to protect the wheel from wear and tear. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ... Coal is a fossil fuel extracted from the ground by deep mining, coal mining (open-pit mining or strip mining). ... The chemical compound acetylene, also called ethyne, was discovered in 1836 by Edmund Davy, in England; its chemical formula is C2H2 and its structure is: Acetylene is a colorless and extremely flammable gas at standard temperature and pressure, with a melting point of -80. ...


Production

In the United States, western Europe, and Japan, butadiene is produced as a byproduct of the steam cracking process used to produce ethylene. Butadiene is isolated from the other hydrocarbons produced in steam cracking by extraction into a solvent such as acetonitrile or dimethylformamide, from which it is then stripped by distillation. World map showing Europe (geographically) When considered a continent, Europe is the worlds second-smallest continent in terms of area, with an area of 10,600,000 km² (4,140,625 square miles), making it larger than Australia only. ... In petroleum geology and chemistry, cracking is the process whereby complex organic molecules (e. ... Ethylene or ethene is the simplest alkene hydrocarbon, consisting of two carbon atoms and four hydrogens. ... // Definition In chemistry, a hydrocarbon is any chemical compound that consists only of carbon (C) and hydrogen (H). ... In chemistry, liquid-liquid extraction is a useful method to separate components (compounds) of a mixture. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Acetonitrile is an organic molecule, often used as a solvent, with the chemical formula of CH3CN. Also known as methyl cyanide, it is the simplest of the organic nitriles. ... Dimethylformamide, also known under the names N,N-dimethylformamide and DMF, is a clear, water-miscible liquid and common solvent that is often used in chemical reactions. ... Strathisla whisky distillery in Keith, Scotland Distillation is a means of separating liquids through differences in their vapor pressures. ...


In other parts of the world, including eastern Europe, China, and India, butadiene is also produced from ethanol via the intermediate crotonaldehyde. Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ...


Uses

Most butadiene is polymerized to produce synthetic rubber. While polybutadiene itself is a very soft, almost liquid material, polymers prepared from mixtures of butadiene with styrene or acrylonitrile, such as ABS, are both tough and elastic. Styrene-butadiene rubber is the material most commonly used for the production of automobile tires. A polymer is not a generic term used to describe a substantially long molecule. ... Polybutadiene is a synthetic rubber that has a high resistance to wear and is used especially in the manufacture of tires. ... Acrylonitrile (CH2=CH-C≡N), is a pungent smelling, extremely flammable organic liquid. ... Monomers in ABS polymer Acrylonitrile butadiene styrene, or ABS, (chemical formula ) is a common thermoplastic used to make light, rigid, molded products such as pipes, golf club heads (used for its good shock absorbance), automotive body parts, enclosures and toys including LEGO bricks. ...


Smaller amounts of butadiene are used to make nylon via the intermediate adiponitrile, other synthetic rubber materials such as chloroprene, and the solvent sulfolane. This article covers the material nylon. ... Chemical Structure of Chloroprene Chloroprene is the common name for the organic compound 2-chloro-1,3-butadiene, which has the chemical formula C4H5Cl. ...


Safety

Contact with liquid butadiene can result in irritation of the skin, eyes, and mucous membranes. Since it often stored as a refrigerated liquid, frostbite is another possible consequence of exposure. When inhaled, butadiene is a mild depressant and can result in drowsiness, although very high concentrations are necessary to produce unconsciousness or death. Model of the layers of human skin In zootomy and dermatology, skin is an organ of the integumentary system; which is composed of a layer of tissues that protect underlying muscles and organs. ... This article refers to the sight organ. ... The mucous membranes (or mucosae; singular: mucosa) are linings of ectodermic origin, covered in epithelium, and are involved in absorption and secretion. ... Frostbite - or Congelatio in medical terminology - is the medical condition where damage is caused to skin and other tissues due to extreme cold. ...


In some animals, long-term exposure to butadiene can result in cancer of the liver or kidneys. Butadiene is a potent carcinogen in mice, but only a weak carcinogen in rats. Studies of workers in chemical plants using butadiene have shown no conclusive increase in cancer risk for whatever amount of butadiene these workers may have been exposed to, so butadiene remains classified as only a potential human carcinogen. When normal cells are damaged or old they undergo apoptosis; cancer cells, however, avoid apoptosis. ... The liver is an organ in vertebrates, including humans. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ...


  Results from FactBites:
 
Butadiene - Wikipedia, the free encyclopedia (685 words)
Butadiene can refer to either one of two hydrocarbon chemical compounds which are alkenes that are isomers of each other.
In the United States, western Europe, and Japan, butadiene is produced as a byproduct of the steam cracking process used to produce ethylene.
Butadiene is isolated from the other hydrocarbons produced in steam cracking by extraction into a solvent such as acetonitrile or dimethylformamide, from which it is then stripped by distillation.
Acrylonitrile butadiene styrene - Wikipedia, the free encyclopedia (184 words)
It is a copolymer made by polymerizing styrene and acrylonitrile in the presence of polybutadiene.
The butadiene, a rubbery substance, provides resilience even at low temperatures.
ABS can be used between -25°C and +60°C. Production of 1 kg of ABS requires the equivalent of about 2 kg of oil for raw materials and energy.
  More results at FactBites »

 
 

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