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1,3-Butadiene

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Name

1,3-Butadiene

EINECS 203-450-8
CAS No. 106-99-0 Density 0.638 g/cm3
Solubility Soluble in alcohol, ether, acetone, benzene, ethylene dichloride, amyl acetate, furfural and acetic acid copper ammonia solution, insoluble in water Melting Point -108.9 °C
Formula C4H6 Boiling Point -4.4 °C
Molecular Weight 54.09 Flash Point
Transport Information UN 1010 2.1 Appearance colourless gas
Safety 53-45-62-46-36/37-26-61-33-16 Risk Codes 45-46-12-67-65-63-48/20-36/38-11-62-51/53-38
Molecular Structure Molecular Structure of 106-99-0 (1,3-Butadiene) Hazard Symbols HighlyF+,ToxicT,FlammableF,DangerousN
Synonyms

Biethylene;Bivinyl;Butadiene;Butadiene-1,3;Divinyl;Erythrene;Vinylethylene;a,g-Butadiene;

 

1,3-Butadiene History

In 1863, a French chemist isolated a previously unknown hydrocarbon from the pyrolysis of amyl alcohol. This hydrocarbon was identified as butadiene in 1886, after Henry Edward Armstrong isolated it from among the pyrolysis products of petroleum.
In 1910, the Russian chemist Sergei Lebedev polymerized butadiene(106-99-0), and obtained a material with rubber-like properties. This polymer was, however, too soft to replace natural rubber in many roles, especially automobile tires.
The butadiene(106-99-0) 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 IG Farben in Germany, made a copolymer of styrene and butadiene(106-99-0) 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.

1,3-Butadiene Consensus Reports

Reported in EPA TSCA Inventory. Community Right-To-Know List.

1,3-Butadiene Standards and Recommendations

DOT Classification:  2.1; Label: Flammable Gas
OSHA PEL: TWA 1 ppm; STEL 5 ppm
ACGIH TLV: TWA 2 ppm; Suspected Human Carcinogen
DFG MAK: Confirmed Human Carcinogen
NIOSH REL: Reduce to lowest feasible level

1,3-Butadiene Analytical Methods

For occupational chemical analysis use OSHA: #ID-56 or NIOSH: 1,3-Butadiene, 1024.

1,3-Butadiene Specification

1,3-Butadiene is a colorless gas with an aromatic odor has an isomer 1,2-butadiene. They also can called butadiene. But most of the time this name refers to 1,3-butadiene. This chemical is easily liquefied, flammable and aggregate. 1,3-Butadiene is the important momer in the manufacture of synthetic rubber and synthetic resin.

Preparation: 1. From ethanol: Use ethanol as raw material, magnesium oxide and silica as main catalysts. Then add active additive at the 360 ~ 370 °C. Finally, after the catalytic dehydrogenation and dehydration, the 1,3-Butadiene is obtained.
2 CH3CH2OH → CH2=CH-CH=CH2 + 2 H2O + H2

2. Extraction from C4 hydrocarbons: The by-product C4 cut fraction can be obtained by ethylene splitting decomposition. Use solvent extraction to extract 1,3-butadiene. According to the different solvents, this method can be divided into acetonitrile extraction and N, N-dimethylformamide extraction.

3. 1,3-Butadiene also can be largely produced from oil gas that is obtained by the catalytic dehydrogenation from butene or butene-butane mixture. Besides, it can also be directly obtained by cracking naphtha and light oil.

Uses: In terms of synthetic rubber, 1,3-butadiene is used in the production of butadiene styrene rubber and butadiene rubber, ethylene-propylene rubber, nitrile rubber, neoprene, SBR, etc.; in synthetic resin, it is used in the production of ABS, BS, SBS, MBS, epoxidation polybutadiene resins, liquid butadiene oligomer, etc.; in organic chemical production, it is used to synthesize sulfolane, 1,4-butanediol, adiponitrile, synthetic anthraquinone, 1,4-hexadiene , cyclooctadiene, cyclododecatriene, etc. 1,3-Butadiene is also used as raw material to make plasticizers, curing agents and flame retardants and so on.

Safty: 1,3-Butadiene may cause cancer, heritable genetic damage, lung damage if swallowed and skin dryness or cracking. Moreover, it is irritating to eyes and skin and has danger of serious damage to health by prolonged exposure through inhalation. This chemical is also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. Damage to the central nervous system will start to occur at acute high exposure. If you want to contact this product, you must wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Structure Descriptors:
1.Smiles:C(C=C)=C
2.InChI:InChI=1/C4H6/c1-3-4-2/h3-4H,1-2H2

Toxicity:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TCLo inhalation 2000ppm/7H (2000ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 69, 1944.
human TCLo inhalation 8000ppm (8000ppm) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: COUGH
Industrial Medicine. Vol. 17, Pg. 199, 1948.
mouse LC50 inhalation 270gm/m3/2H (270000mg/m3)   Archives of Environmental Health. Vol. 18, Pg. 878, 1969.
mouse LD50 oral 3210mg/kg (3210mg/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-288, Pg. 1984,
rabbit LCLo inhalation 25pph/23M (250000ppm) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 69, 1944.
rat LC50 inhalation 285gm/m3/4H (285000mg/m3) BEHAVIORAL: GENERAL ANESTHETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Russian Pharmacology and Toxicology Vol. 31, Pg. 162, 1968.
rat LD50 oral 5480mg/kg (5480mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 14, 1986.

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