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1,3-butadiene

1,3-Butadiene
1,3-Butadiene
1,3-Butadiene
1,3-Butadiene-3d.png
Names
Preferred IUPAC name
Buta-1,3-diene
Other names
Biethylene
Erythrene
Divinyl
Vinylethylene
Bivinyl
Butadiene
Identifiers
106-99-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:39478 YesY
ChEMBL ChEMBL537970 YesY
ChemSpider 7557 YesY
ECHA InfoCard 100.003.138
EC Number 271-039-0
KEGG C16450 YesY
PubChem 7845
RTECS number EI9275000
UNII JSD5FGP5VD YesY
UN number 1010
Properties
C4H6
Molar mass 54.0916 g/mol
Appearance Colourless gas
or refrigerated liquid
Odor mildly aromatic or gasoline-like
Density 0.6149 g/cm3 at 25 °C, solid
0.64 g/cm3 at −6 °C, liquid
Melting point −108.9 °C (−164.0 °F; 164.2 K)
Boiling point −4.4 °C (24.1 °F; 268.8 K)
0.735 g/100 mL
Solubility very soluble in acetone
soluble in ether, ethanol
Vapor pressure 2.4 atm (20°C)
1.4292
Viscosity 0.25 cP at 0 °C
Hazards
Main hazards Flammable, irritative, carcinogen
Safety data sheet See: data page
ECSC 0017
R-phrases R45 R46 R12
S-phrases S45 S53
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −85 °C (−121 °F; 188 K) liquid flash point
420 °C (788 °F; 693 K)
Explosive limits 2–12%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
548 mg/kg (rat, oral)
115,111 ppm (mouse)
122,000 ppm (mouse, 2 hr)
126,667 ppm (rat, 4 hr)
130,000 ppm (rat, 4 hr)
250,000 ppm (rabbit, 30 min)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 1 ppm ST 5 ppm
REL (Recommended)
potential occupational carcinogen
IDLH (Immediate danger)
2000 ppm
Related compounds
Related alkenes
and dienes
Isoprene
Chloroprene
Related compounds
Butane
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

1,3-Butadiene is a simple conjugated diene with the formula C4H6. It is an important industrial chemical used as a monomer in the production of synthetic rubber. The molecule can be viewed as two vinyl groups (CH2=CH2) joined together. The word butadiene usually refers to 1,3-butadiene which has the structure H2C=CH−CH=CH2.

Although 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 EPA lists it as the "mobile source air toxic" with the highest normalized risk factor, exceeding that of formaldehyde, the second riskiest air toxic emitted by motor vehicles, by a factor of more than 20.

The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. However, this allene is difficult to prepare and has no industrial significance. This diene is also not expected to act as a diene in a Diels–Alder reaction due to its structure. To effect a Diels-Alder reaction only a conjugated diene will suffice. The rest of this article concerns only 1,3–butadiene.

In 1863, the French chemist E. Caventou 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, and obtained a material with rubber-like properties. This polymer was, however, found to be too soft to replace natural rubber in many applications, notably automobile tires.


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