Chloroprene



Chloroprene
IUPAC name 2-Chloro-1,3-butadiene
Other names Chloroprene
Identifiers
CAS number 126-99-8
RTECS number EL9625000
SMILES C=C(Cl)C=C
Properties
Molecular formula C4H5Cl
Molar mass 88.5365 g/mol
Appearance Colorless liquid.
Density 0.9598 g/cm3, liquid.
Melting point

-130 °C, 143 K, -202 °F

Boiling point

59.4 °C, 333 K, 139 °F

Solubility in water 0.026 g/100 mL, liquid.
Hazards
Main hazards Highly flammable, toxic.
NFPA 704
3
2
0
 
R-phrases R45, R11, R20/22,
R36/37/38, R48/20
S-phrases S45
Flash point -15.6°C
Related Compounds
Related Dienes Isoprene
Related compounds Vinyl chloride
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Chloroprene is the common name for the DuPont gave it when the company first developed it and currently used by DuPont Dow.

Production of chloroprene

Chloroprene is produced in three steps from dehydrochlorination of 3,4-dichloro-1-butene.

distillation.

Acetylene process

Until the 1960s, chloroprene production was dominated by the “acetylene process,” which was modeled after the original synthesis of vinyl acetylene.[2] In this process, cuprous chloride, rearranges to the targeted 2-chloro-1,3-butadiene.[1] The conversion is shown here:


This process had disadvantages in that it is very energy-intensive and has high investment costs. Furthermore, the intermediate vinyl acetylene is unstable.

References

  1. ^ a b Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry, 2006 John Wiley-VCH: Weinheim.DOI: 10.1002/14356007.a06_233.pub2
  2. ^ J. Am. Chem. Soc. 53: 4203 - 4225. doi:10.1021/ja01362a042.
  • Polychloroprene (CR), chloroprene rubber
 
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