1,3-BUTADIENE Chemical Properties,Uses,Production
Description
1,3-Butadiene is a simple conjugated diene. It 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. It is an important industrial chemical used as a monomer in the production
of synthetic rubber. Most butadiene is polymerised 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 tyres. Smaller amounts of butadiene are used to make nylon via the intermediate adiponitrile, other synthetic rubber materials such as chloroprene, and the
solvent sulpholane. Butadiene is used in the industrial production of cyclododecatriene
via a trimerisation reaction.
Chemical Properties
1,3-Butadiene is a simple conjugated diene. It is a colorless gas with a mild aromatic or
gasoline-like odor 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. It is an important industrial chemical used as a monomer in the production of
synthetic rubber. 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. Styrenebutadiene rubber is the material most commonly used for the production of automobile
tires. Smaller amounts of butadiene are used to make nylon via the intermediate adiponitrile, other synthetic rubber materials such as chloroprene, and the solvent sulfolane.
Butadiene is used in the industrial production of cyclododecatriene via a trimerization
reaction.
Chemical Properties
colourless gas, or pressurised liquid (odour TLV 1.6 ppm)
Uses
Synthetic elastomers (styrene-butadiene,
polybutadiene, neoprene, nitriles), ABS resins,
chemical intermediate.
Definition
ChEBI: A butadiene with unsaturation at positions 1 and 3.
General Description
Butadiene, inhibited is a colorless gas with an aromatic odor. 1,3-BUTADIENE is shipped as a liquefied gas under its vapor pressure. Contact with the liquid can cause frostbite. 1,3-BUTADIENE is easily ignited. Its vapors are heavier than air and a flame can flash back to the source of leak very easily. 1,3-BUTADIENE can asphyxiate by the displacement of air. 1,3-BUTADIENE must be shipped inhibited as butadiene is liable to polymerization. If polymerization occurs in the container, 1,3-BUTADIENE may violently rupture. Under prolonged exposure to fire or intense heat the containers may rupture violently and rocket. 1,3-BUTADIENE is used to make synthetic rubber and plastics, and to make other chemicals.
Air & Water Reactions
Highly flammable. In contact with air, butadiene may form violently explosive peroxides, which can be exploded by mild heat or shock. Solid butadiene absorbs enough oxygen at sub atmospheric pressures to make 1,3-BUTADIENE explode violently when heated just above its melting point [Ind. Eng. Chem. 51:733 1959].
Reactivity Profile
A colorless gas, 1,3-BUTADIENE can react with oxidizing reagents. Upon long exposure to air 1,3-BUTADIENE forms explosive peroxides. They are sensitive to heat or shock; sudden polymerization may occur [Scott, D. A., Chem. Eng. News, 1940, 18, p.404]. Butadiene polyperoxides are insoluble in liquefied butadiene (m. p. -113° C, b. p. -2.6° C) and progressively separate leading to local concentration build up. Self-heating from a spontaneous decomposition will lead to explosion [Hendry, D. G. et al., Ind. Eng. Chem., 1968, 7, p. 136, 1145]. Explodes on contact with aluminum tetrahydroborate, potentially explosive reaction with chlorine dioxide (peroxide) and crotonaldehyde (above 180° C). Reaction with sodium nitrite forms a spontaneously flammable product [Sax, 9th ed., 1996, p. 539].
Hazard
A confirmed carcinogen. Irritant in high
concentration. Highly flammable gas or liquid,
explosive limits in air 2–11%. May form explosive
peroxides on exposure to air. Must be kept inhibited
during storage and shipment. Inhibitors often used
are di-n-butylamine or phenyl-β-naphthylamine.
Storage is usually under pressure or in insulated
tanks <35F (<1.67C).
Health Hazard
Slight anesthetic effect at high concentrations; causes ``frostbite'' from skin contact; slight irritation to eyes and nose at high concentrations.
Health Hazard
The symptoms of poisoning include distorted blurred vision, vertigo, general tiredness, decreased blood pressure, headache, and nausea. Exposures to very high concentrations of 1,3-butadiene are known to cause CNS depression, decreased pulse rate,
drowsiness, fatigue, vertigo, ataxia, unconsciousness, coma, respiratory paralysis, and
death. Several studies show butadiene exposure increases the risk of cardiovascular
diseases and cancer. There is a lack of human data on the effects butadiene. Animal
studies have shown breathing butadiene during pregnancy can increase the number
of birth defects.
Fire Hazard
Behavior in Fire: Vapors heavier than air and may travel a considerable distance to a source of ignition and flashback. Containers may explode in a fire due to polymerization.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic and
neoplastigenic data. An experimental
teratogen. Mutation data reported.
Inhalation of high concentrations can cause
unconsciousness and death. Human
systemic effects by inhalation: cough,
hallucinations, dstorted perceptions,
changes in the visual field and other
1,3-BUTADIENE Preparation Products And Raw materials
Raw materials
Preparation Products
Cross-linking agent
Carboxy styrene-butadiene latex
Methacrylonitrile
1-BUTENE
CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98%
modified filling agent SBR
5-ETHYLIDENE-2-NORBORNENE
Muscone
N,N,N',N'-TETRAMETHYL-2-BUTENE-1,4-DIAMINE
2-(2-CHLOROETHOXY)-BENZENESULFONAMIDE
CYCLODODECANE
VITAMIN K4
Sulfolane
butadiene-styrene latex
Polyvinylpyrrolidone
4-VINYLCYCLOHEXENE DIOXIDE
3-SULFOLENE
Captan
Menadione
cis-1,2,3,6-Tetrahydrophthalic anhydride
Maleic hydrazide
1,4-Dicyanobutane
1,2,3,4-Tetrabromobutane
POLYBUTADIENE DIACRYLATE
1,6-HEXANEDIAMINE
1,2,5,6,9,10-Hexabromocyclododecane
POLYSTYRENE-B-POLYBUTADIENE-B-POLYSTYRENE
DOWEX(R) 1X8
Dodecanedioic acid
2,4,4-TRIMETHYL-1-PENTENE
ABS Resins
2-BUTANOL
FUSEL OIL
Cyclododeca-1,5,9-triene
IRONE
butadiene resin emulsion LHYJ-DS50
Ti(Co)Ziegler catalyst
1,4-HEXADIENE
N-Hydroxymethyl-3,4,5,6-tetrahydrophthalimide
