ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Acyclic hydrocarbons > 1,3-BUTADIENE
1,3-BUTADIENE Chemical Properties
- Melting point:−109 °C(lit.)
- Boiling point:−4.5 °C(lit.)
- Density 0.62 g/mL at 20 °C(lit.)
- vapor density 1.9 (15 °C, vs air)
- vapor pressure 1863 mm Hg ( 21 °C)
- refractive index 1.4292
- Flash point:−105 °F
- storage temp. 0-6°C
- solubility water: soluble0.5g/L at 20°C
- form Colorless gas
- explosive limit12%
- Odor Threshold0.23ppm
- Water Solubility 735mg/L(25 ºC)
- FreezingPoint -108.91℃
- Merck 14,1509
- BRN 605258
- Henry's Law Constant(x 10-2 atm?m3/mol): 6.3 at 25 °C (Hine and Mookerjee, 1975)
- Exposure limitsTLV-TWA 10 ppm (～22 mg/m3) (ACGIH), 1000 ppm (OSHA and NIOSH); IDLH 20,000 ppm (NIOSH); A2–Suspected Human Carcinogen (ACGIH).
- Stability:Stable. Extremely flammable. May form explosive mixtures with air. Incompatible with strong oxidizing agents, copper, copper alloys. May contain stabilizer.
- CAS DataBase Reference106-99-0(CAS DataBase Reference)
- IARC1 (Vol. Sup 7, 54, 71, 97, 100F) 2012
- EPA Substance Registry System1,3-Butadiene (106-99-0)
- Hazard Codes F+,T,F,N
- Risk Statements 45-46-12-67-65-63-48/20-36/38-11-62-51/53-38
- Safety Statements 53-45-62-46-36/37-26-61-33-16
- RIDADR UN 1010 2.1
- WGK Germany 2
- RTECS EI9275000
- F 4.5-31
- Autoignition Temperature788 °F
- Hazard Note Extremely Flammable/Carcinogen
- DOT Classification2.1 (Flammable gas)
- HazardClass 2.1
- PackingGroup II
- HS Code 29012410
- ToxicityLC50 (inhalation) for mice 270 gm/m3/2-h, rats 285 gm/m3/4-h (quoted, RTECS, 1985).
1,3-BUTADIENE Usage And Synthesis
- Description1,3-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.
- Physical propertiesColorless gas with a mild, aromatic or gasoline-like odor. Experimentally determined detection and recognition odor threshold concentrations were 1.0 mg/m3 (0.45 ppmv) and 2.4 mg/m3 (1.1 ppmv), respectively (Hellman and Small, 1974).
- Uses1,3-Butadiene is a petroleum product obtainedby catalytic cracking of naphtha orlight oil or by dehydrogenation of buteneor butane. It is used to produce butadiene–styrene elastomer (for tires), syntheticrubber, thermoplastic elastomers, foodwrapping materials, and in the manufactureof adiponitrile. It is also used forthe synthesis of organics by Diels–Aldercondensation.
- UsesSynthetic elastomers (styrene-butadiene, polybutadiene, neoprene, nitriles), ABS resins, chemical intermediate.
1,3-Butadiene can undergo a four-component coupling reaction with aryl Grignard reagents, and alkyl fluorides in the presence of nickel catalyst to form 1,6-octadiene carbon compound substituted with alkyl and aryl groups at the 3- and 8-positions.
1,3-Butadiene is a useful diene for Diels Alder reaction.
It may be used in the synthesis of the following:
- 1-Silyl-substituted 1,3-butadienes, by [RuHCl(CO)(PCy3)2]-catalyzed silylative coupling of terminal (E)-1,3-dienes with vinylsilanes.
- Synthetic rubber and thermoplastic resins.
- Disilylated dimers by reacting with chlorosilanes.
- Octa-2,7-dien-1-ol via palladium catalyzed-hydrodimerization.
- UsesOne major use of 1,3-butadiene has been in the
making of synthetic rubber. Among the types of
synthetic rubber made with 1,3-butadiene are
styrene-butadiene and nitrile-butadiene rubbers.
Cis-polybutadiene is also an extender and substitute
for rubber, and trans-polybutadiene is a
type of rubber with unusual properties.
1,3-Butadiene is also used extensively for various polymerizations in manufacturing plastics. It combines with activated olefins in the Diels-Alder reaction to give hydroaromatic hydrocarbons. 1,3-Butadiene undergoes 1,4 cyclization with reactants containing sulfur, oxygen, and nitrogen.
- DefinitionChEBI: A butadiene with unsaturation at positions 1 and 3.
- Production MethodsExcept for a small amount of butadiene produced by the oxydehydrogenation of n-butane, most of butadiene is produced commercially as a by-product of ethylene production during the steam cracking of hydrocarbon streams. It is separated and purificated from other components by extractive distillation, using acetonitrile and dimethylformamide as solvents.
- General DescriptionButadiene, 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 ReactionsHighly 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 ProfileA 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].
- HazardA 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 HazardThe toxicity of 1,3-butadiene has been foundto be very low in humans and animals. It isan asphyxiant. In humans, low toxic effectsmay be observed at exposure to 2000 ppmfor 7 hours. The symptoms may be hallucinations,distorted perception, and irritation ofeyes, nose, and throat. Higher concentrationsmay result in drowsiness, lightheadedness,and narcosis. High dosages of 1,3-butadienewas toxic to animals by inhalation and skincontact. General anesthetic effects and respiratorydepression were noted. Concentrationsof 25–30% may be lethal to rats and rabbits.Contact with the liquefied gas can cause burnand frostbite.
Exposure to 1,3-butadiene caused cancersin the stomach, lungs, and blood in ratsand mice. It is suspected to be a humancarcinogen. It is a mutagen and a teratogen.
- Fire HazardBehavior 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.
- Materials Uses1,3-Butadiene is noncorrosive and may be used with any common metals. Steel is recommended for tanks and piping in butadiene service by some authorities. If used with plastics, compatibility must be confirmed. Welded rather than threaded connections are similarly recommended because 1,3-butadiene tends to leak through even extremely small openings. If threaded connections are used, Schedule 80 pipe should be used. Before being exposed to 1,3-butadiene that is not inhibited, iron surfaces should be treated with an appropriate reducing agent such as sodium nitrite because polymerization is accelerated by oxygen (even if present as in ferrous oxide), as well as by heat.
- Safety ProfileConfirmed 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
- Physiological effectsIf inhaled in high concentrations, 1,3-butadiene
has an anesthetic or mild narcotic action, which
appears to vary with individuals. Inhalation of a
I percent concentration in air has been reported
to have had no effect on the respiration or blood
pressure of individuals. However, such exposure
may cause the pulse rate to quicken and
give a sensation of prickling and dryness in the
nose and mouth. Inhalation in higher concentrations
has brought on blurring of vision and nausea
in some persons. Inhalation in excessive
amounts leads to progressive anesthesia, irritation
of eyes, lungs, and nasal passages. Exposure
to a 25 percent concentration for 23 minutes
proved fatal in one instance. No cumulative
action on the blood, lungs, liver, or kidneys has
been reported. Because 1,3-butadiene liquid
evaporates rapidly, prolonged contact between
liquid butadiene and the skin causes freezing of
the tissue. Delayed skin bums may result if liquid
butadiene is allowed to remain trapped in
clothing or in shoes.
OSHA has concluded that there is strong evidence that workplace exposure to 1,3-butadiene poses an increased risk of death from cancers of the Iymphokematopoietic system. ACGIH has classified 1,3-butadiene as a "suspected human carcinogen" . The National Toxicology Program has classified 1,3-butadiene as showing clear evidence of carcinogenicity.
- Carcinogenicity1,3-Butadiene is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans, including epidemiological and mechanistic studies. 1,3-Butadiene was first listed in the Fifth Annual Report on Carcinogens in 1989 as reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. The listing was revised to known to be a human carcinogen in the Ninth Report on Carcinogens in 2000.
- SourceSchauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of 1,3-butadiene was 177 mg/kg of pine burned. Emission rates of 1,3-butadiene were not measured during the combustion of oak and eucalyptus.
- Environmental FateSurface Water. The estimated volatilization half-life of 1,3-butadiene in a model river 1 m deep,
flowing 1 m/sec and a wind speed of 3 m/sec is 3.8 h (Lyman et al., 1982).
Photolytic. The following rate constants were reported for the reaction of 1,3-butadiene and OH radicals in the atmosphere: 6.9 x 10-11 cm3/molecule·sec (Atkinson et al., 1979) and 6.7 x 10-11 cm3/molecule·sec (Sablji? and Güsten, 1990). Atkinson and Carter (1984) reported a rate constant of 6.7–8.4 x 10-11 cm3/molecule·sec for the reaction of 1,3-butadiene and ozone in the atmosphere. Photooxidation reaction rate constants of 2.13 x 10-13 and 7.50 x 10-18 cm3/molecule·sec were reported for the reaction of 1,3-butadiene and NO3 (Benter and Schindler, 1988; Sablji? and Güsten, 1990). The half-life in air for the reaction of 1,3-butadiene and NO3 radicals is 15 h (Atkinson et al., 1984a).
Chemical/Physical. Will polymerize in the presence of oxygen if no inhibitor is present (Hawley, 1981).
- storage1,3-Butadiene is stored in a cool and wellventilatedlocation separated from combustibleand oxidizing substances. Smallamounts of stabilizers, such as o-dihydroxybenzene,p-tert-butylcatechol, or aliphaticmercaptans, are added to prevent its polymerizationor peroxides formation. The cylindersare stored vertically and protected againstphysical damage.
- Waste DisposalDisposal of l,3-butadiene by venting, incineration, using a suitable flare system, or by other means may be subject to permitting by federal, state, provincial, or local regulations. Persons involved with disposal of 1,3-butadiene should check with the environmental authorities having jurisdiction to determine the applicability of permitting regulations to disposal activities.
- GRADES AVAILABLE1,3-Butadiene is available for commercial and
industrial use in various grades having much the
same component proportions from one producer
All grades contain approximately lIS ppm of a polymerization inhibitor, such as tertiary- butylcathechol. Distillation or washing with dilute caustic solution is used for removing the inhibitor when necessary.
1,3-BUTADIENE Preparation Products And Raw materials
- Raw materialsTolueneNitrogenAcetonitrilePETROLEUM ETHERCalcium carbideN-BUTANE
- Preparation ProductsSulfolane1,6-HEXANEDIAMINEPOLYSTYRENE-B-POLYBUTADIENE-B-POLYSTYRENEDOWEX(R) 1X84-VINYLCYCLOHEXENE DIOXIDEFUSEL OIL1-BUTENEN-Hydroxymethyl-3,4,5,6-tetrahydrophthalimide2-(2-CHLOROETHOXY)-BENZENESULFONAMIDECaptan1,4-DicyanobutaneMenadionecis-1,2,3,6-Tetrahydrophthalic anhydride3,6-DihydroxypyridazineCross-linking agent1,2,5,6,9,10-Hexabromocyclododecane2-BUTANOLDodecanedioic acid5-ETHYLIDENE-2-NORBORNENEN,N,N',N'-TETRAMETHYL-2-BUTENE-1,4-DIAMINEMethacrylonitrilemodified filling agent SBRCYCLODODECANECIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE; >98%3-MethylcyclopentadecanonePOLYBUTADIENE DIACRYLATEABS Resins1,4-HEXADIENE3-SULFOLENEPolyvinylpyrrolidonebutadiene resin emulsion LHYJ-DS50Cyclododeca-1,5,9-triene2,4,4-TRIMETHYL-1-PENTENETi(Co)Ziegler catalystCarboxy styrene-butadiene latexIRONEbutadiene-styrene latexVITAMIN K41,2,3,4-Tetrabromobutane
- Acrylonitrile acrylonitrile-butadiene rubber Irisone Retinoic acid BCP Hexachlor-1,3-butadien,hexachlor-1,3-butadien(czech 2,5-Dimethyl-3,4-diphenylcyclopentadienone 1,2,3,4-Tetrachloro-5,5-dimethoxycyclopentadiene LITHIUM CYCLOPENTADIENIDE BETA-CAROTENE 1-METHOXY-1,3-CYCLOHEXADIENE 1,2,3,4,5-Pentamethylcyclopentadiene Colchicine Vitamin A TETRAPHENYLCYCLOPENTADIENONE 1,2,3,4-TETRAPHENYL-1,3-CYCLOPENTADIENE 1,3-CYCLOHEXADIENE DIPHENYLFULVENE
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