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CAS NUMBER: 106-99-0
EC NUMBER: 203-450-8
MOLECULAR FORMULA: CH2=(CH)2=CH2
MOLECULAR WEIGHT: 54.09
IUPAC NAME: buta-1,3-diene
1,3-Butadiene is the organic compound with the formula (CH2=CH)2.
1,3-Butadiene is a colorless gas that is easily condensed to a liquid.
1,3-Butadiene is important industrially as a precursor to synthetic rubber.
The molecule can be viewed as the union of two vinyl groups.
1,3-Butadiene is the simplest conjugated diene.
Although 1,3-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 vehicles.
The name 1,3-Butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3.
This allene has no industrial significance
1,3-Butadiene is a synthetic, colorless gas that is practically insoluble in water and soluble in ethanol, ether, acetone and benzene.
1,3-Butadiene is used primarily as a monomer to manufacture many different types of polymers and copolymers and as a chemical intermediate in the production of industrial chemicals.
When heated, 1,3-Butadiene emits acrid fumes and is flammable.
In the presence of air, 1,3-Butadiene oxidizes to form explosive peroxides.
PRODUCTION:
-Extraction from C4 hydrocarbons:
1,3-Butadiene is typically isolated from the other four-carbon hydrocarbons produced in steam cracking by extractive distillation using a polar aprotic solvent such as acetonitrile, N-methyl-2-pyrrolidone, furfural, or dimethylformamide, from which it is then stripped by distillation
-From dehydrogenation of n-butane:
1,3-Butadiene can also be produced by the catalytic dehydrogenation of normal butane (n-butane).
Today, 1,3-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 at high temperatures
-From ethanol:
1,3-Butadiene is also produced from ethanol.
While not competitive with steam cracking for producing large volumes of 1,3-Butadiene, lower capital costs make production from ethanol a viable option for smaller-capacity plants.
-From butenes:
1,3-Butadiene can also be produced by catalytic dehydrogenation of normal butenes.
-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.
1,3-Butadiene can be produced by the retro-Diels-Alder reaction of cyclohexene.
Sulfolene is a convenient solid storable source for 1,3-butadiene in the laboratory.
1,3-Butadiene releases the diene and sulfur dioxide upon heating.
USES:
Most 1,3-Butadiene is used to make synthetic rubbers for the manufacture of tyres, grommets and elastic bands.
The conversion of 1,3-Butadiene to synthetic rubbers is called polymerization, a process by which small molecules (monomers) are linked to make large ones (polymers).
The mere polymerization of 1,3-Butadiene gives polybutadiene, which is a very soft, almost liquid material.
The polymerization of 1,3-Butadiene and other monomers gives copolymers, which are more valued. The polymerization of butadiene and styrene and/or acrylonitrile, such as acrylonitrile butadiene styrene (ABS), nitrile-butadiene (NBR), and styrene-butadiene (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.
Smaller amounts of butadiene are used to make adiponitrile, 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.
1,3-Butadiene is used to make the solvent sulfolane.
1,3-Butadiene is also useful in the synthesis of cycloalkanes 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 1,3-Butadiene with one or two other molecules of butadiene, i.e., dimerization and trimerization respectively.
Via dimerizatiion 1,3-Butadiene is converted to 4-vinylcyclohexene and cyclooctadiene.
In fact, vinylcyclohexene is a common impurity that accumulates when 1,3-Butadiene is stored.
Via trimerization, 1,3-Butadiene is converted to cyclododecatriene.
Some of these processes employ nickel- or titanium-containing catalysts
Reactions:
The industrial uses illustrate the tendency of 1,3-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.
1,3-Butadiene is a partner in Diels-Alder reactions, e.g. with maleic anhydride to give tetrahydrophthalic anhydride.
Like other dienes, butadiene is a ligand for low-valent metal complexes, e.g. the derivatives Fe(butadiene)(CO)3 and Mo(butadiene)3.
1,3-Butadiene is a chemical made from the processing of petroleum.
1,3-Butadiene is the 36th highest volume chemical produced in the United States.
1,3-Butadiene is a colorless gas with a mild gasoline-like odor.
About 75% of the manufactured 1,3-Butadiene is used to make synthetic rubber.
Synthetic rubber is widely used for tires on cars and trucks.
1,3-Butadiene is also used to make plastics including acrylics.
Small amounts are found in gasoline.
This substance is used by consumers, in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
APPLICATIONS:
-adhesives and sealants
-anti-freeze products
-coating products
-fillers
-putties
-plasters
-modelling clay
-finger paints
-non-metal-surface treatment products
-inks and toners
-leather treatment products
-lubricants and greases
-polishes and waxes
-polymers
-textile treatment products
-dyes
1,3-Butadiene is used in polymers.
Other release to the environment of 1,3-Butadiene is likely to occur from indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners)
1,3-Butadiene is a colorless gas with an aromatic odor.
1,3-Butadiene is shipped as a liquefied gas under its vapor pressure.
1,3-Butadiene is used to make synthetic rubber and plastics, and to make other chemicals.
1,3-Butadiene is used in the fuels and polymers.
1,3-Butadiene is used in extraction agents and fuels.
1,3-Butadiene is used in formulation of mixtures and/or re-packaging.
1,3-Butadiene is used for the manufacture of chemicals.
PHYSICAL PROPERTIES:
-Molecular Weight: 54.09
-XLogP3: 2
-Exact Mass: 54.0469501914
-Monoisotopic Mass: 54.0469501914
-Topological Polar Surface Area: 0 Ų
-Physical Description: Butadiene is a colorless gas with an aromatic odor
-Color: Colorless
-Form: Gas
-Odor: Mild aromatic or gasoline-like odor
-Boiling Point: -4.4 °C
-Melting Point: -108.9 °C
-Flash Point: -105 °F
-Solubility: 0.01 M
-Density: 0.6149 g/cu cm
-Vapor Density: 1.87
-Vapor Pressure: 2.4 atm
-LogP: 1.99
-Autoignition Temperature: 414 °C
-Viscosity: 101.325 kPa
-Corrosivity: Non-corrosive
-Surface Tension: 13.4 dynes/cm
CHEMICAL PROPERTIES:
-Hydrogen Bond Donor Count: 0
-Hydrogen Bond Acceptor Count: 0
-Rotatable Bond Count: 1
-Heavy Atom Count: 4
-Formal Charge: 0
-Complexity: 21
-Isotope Atom Count: 0
-Defined Atom Stereocenter Count: 0
-Undefined Atom Stereocenter Count: 0
-Defined Bond Stereocenter Count: 0
-Undefined Bond Stereocenter Count: 0
-Covalently-Bonded Unit Count: 1
-Compound Is Canonicalized: Yes
1,3-Butadiene is a colorless gas at room temperature with a gasoline-like odor.
1,3-Butadiene is used to produce synthetic rubber products, such as tires, resins, and plastics, and other chemicals.
1,3-Butadiene is a colorless gas with a mild gasoline odor and is used to make synthetic rubber.
Although it is non-corrosive, 1,3-Butadiene is highly flammable. Commercially, it is available as liquefied gas, which is produced by extracting it from crude butylene concentration stream
Uses & Benefits:
1,3-Butadiene is used as a monomer to produce polymers that are used in commercial and consumer applications, not as a formulated ingredient.
Many consumer goods and materials are made of synthetic rubbers (or elastomers), latexes and plastics produced using 1,3-butadiene.
Elastomers made using 1,3-Butadiene as a “building block” include styrene-butadiene rubber (SBR), polybutadiene rubber (PBR), polychloroprene (neoprene) and nitrile rubber (NR).
Tires:
1,3-Butadiene is used to make synthetic rubber, and SBR is the primary material combined with natural rubber to make tires.
The physical and chemical properties of these rubber polymers provide performance-enhancing components to tires, such as rolling resistance, wear and traction.
Synthetic Turf:
Recycled tire crumb rubber is part of the infill material used in synthetic turf for cushioning and traction.
Paper Coatings:
Styrene-butadiene latex (SB latex) is used to produce paper coatings and products with high-gloss, opacity and brightness, including coated manila and white cardboard, art paper and data recording paper such as pressure-sensitive paper and thermal paper used in catalogues, magazines and advertising flyers.
Carpet:
SB latex is used in back coatings in tufted carpets.
The back coatings hold the tufts in place, anchoring the pile fibers and providing improved stability and resistance to fraying or tuft loss at the cut edges of the carpet.
Gloves and Wetsuits:
Neoprene, one of the earliest synthetic rubber products ever made, is used in gloves, wetsuits and waders (waterproof garments that cover the legs and body used by anglers when fishing), as well as foam.
Neoprene foam is a soft, flexible and durable form-fitting sponge rubber.
1,3-Butadiene provides thermal and moisture insulation and is resistant to ozone, sunlight, and oxidation. Neoprene foam is used in knee and elbow pads, and as joint filler in masonry.
Automotive Parts:
Nitrile rubber, also known as nitrile-butadiene rubber (NBR), is an oil-resistant synthetic rubber used in hoses, automotive gaskets and seals, as well as gloves and other products where oil resistance is required.
Toys:
Acrylonitrile butadiene styrene, also known as ABS plastic, is a heat- and impact-resistant lightweight material that can be used to make materials for toys like building blocks, as well as musical instruments like clarinets and recorders.
ABS plastic’s durable, shock-absorbent properties also make it an ideal for luggage and laptop cases.
Other Consumer Products:
Chewing gum is a rubber that has been flavored and sweetened.
Originally, it was made of natural rubber, but today the rubber used to make chewing gum is usually synthetic.
Along with butadiene, plasticizers and lanolin are some of the ingredients used to make the rubber for chewing gum.
Plastics for food packaging and frames for eye glasses are also made from butadiene.
1,3-Butadiene is a “building block” chemical used to make synthetic rubber.
1,3-Butadiene is a colorless gas and has a mild gasoline odor.
1,3-Butadiene is also used to create the rubber used to make elevator belts, hoses and tubes.
Tires, footwear and sports goods also use synthetic rubber.
1,3-Butadiene is produced through the processing of petroleum and is mainly used in the production of synthetic rubber, but is also found in smaller amounts in plastics and fuel.
Exposure to 1,3-Butadiene mainly occurs in the workplace, including the following industries: synthetic elastomer (rubber and latex) production, petroleum refining, secondary lead smelting, water treatment, agricultural fungicides, production of raw material for nylon, and the use of fossil fuels.
1,3-Butadiene (one-three-byoo-tah-DYE-een) is a colorless gas with a mild, slightly sweet odor.
1,3-Butadiene occurs naturally in petroleum, from which it is extracted at refineries.
1,3-Butadiene is a simple conjugated diene.
1,3-Butadiene 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.
1,3-Butadiene is a colorless, flammable gas with a characteristic odor that condenses readily under pressure.
1,3-Butadiene is an unsaturated hydrocarbon of great industrial importance.
The product has a strong tendency to polymerize, therefore a stabilizer (TBC) is added during the production process.
1,3-Butadiene is recommended to avoid storage temperatures above 25°C
WHAT IS 1,3-BUTADIENE USED FOR?
1,3-Butadiene is used as a synthetic rubber, for example, in vehicle tires, as an additive in the rubberized backing of carpeting, or in the soles of sports shoes to ensure elasticity and durability.
1,3-Butadiene is also needed in the electronics industry, in household appliances and in the construction sector.
In addition, 1,3-Butadiene is an important intermediate for the production of rubber and plastics for applications such as paper finishing, disposable gloves, latex mattresses, conveyor belts, etc.
1,3-Butadiene is an essential component of styrene-butadiene rubber and polybutadiene rubber (in vehicle tires, shoe soles), acrylonitrile-butadiene-styrene and adiponitrile (in electronic devices and housings) and in products of the consumer goods and construction industry (e.g. latex mattresses, disposable gloves).
1,3-Butadiene is a simple conjugated diene.
1,3-Butadiene is a colourless gas with a mild aromatic or gasoline-like odour and incompatible with phenol, chlorine dioxide, copper, and crotonaldehyde.
The gas is heavier than air and may travel along the ground; distant ignition is possible.
1,3-Butadiene is an important industrial chemical used as a monomer in the production of synthetic rubber.
Most 1,3-Butadiene is polymerised to produce synthetic rubber.
SYNONYMS:
1,3-BUTADIENE
Buta-1,3-diene
BUTADIENE
106-99-0
Divinyl
Vinylethylene
Biethylene
Erythrene
Bivinyl
Pyrrolylene
Butadieen
Butadien
Buta-1,3-dien
Buta-1,3-dieen
alpha,gamma-Butadiene
Buta-1,3-dien
1,3 butadiene
1,3-butadien
CH2=CHCH=CH2
.alpha.,.gamma.-Butadiene
1,3-Butadiene (ca. 15% in Toluene)
25339-57-5
1,3-Butadiene (ca. 15% in Hexane)
Butadiene monomer
Butadieen
Butadien
POLYBUTADIENE
EINECS 203-450-8
Buta-1,3-dieen
Poly(butadiene)
1,3-Butadiene 95%
2-Butene-1,4-diylradical
alpha,<<gamma>>-Butadiene
1,3-Butadiene, >=99%
1,3-Butadiene, >=99.6%
[(E)-2-Butene-1,4-diyl]radical
