Chloroprene
Encyclopedia : C : CH : CHL : Chloroprene
| Chloroprene | |
|---|---|
| |
| General | |
| Systematic name | 2-chloro-1,3-butadiene |
| Other names | Chloroprene |
| Molecular formula | C4H5Cl |
| SMILES | C=C([Cl])C=C |
| Molar mass | 88.5365 g/mol |
| Appearance | Colorless liquid. |
| CAS number | |
| Properties | |
| Density and phase | 0.9598 g/cm3, liquid. |
| Solubility in water | 0.026 g/100ml, liquid. |
| Melting point | -130°C (? K) |
| Boiling point | 59.4°C (? K) |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Highly flammable, toxic. |
| NFPA 704 | |
| Flash point | -15.6°C |
| R/S statement | R: R45, R11, R20/22, R36/37/38, R48/20. S: S53, S45. |
| RTECS number | EL9625000 |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related Dienes | ? |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
Chloroprene is the common name for the organic compound 2-chloro-1,3-butadiene, which has the chemical formula C4H5Cl. The chemical structure is shown at right. It is used as monomer for the production of the polymer polychloroprene, a type of synthetic rubber. Polychloroprene is better known to the public as Neoprene, the trade name DuPont gave it when the company first developed it and currently used by DuPont Dow.
Production of chloroprene
The acetylene process was used to produce chloroprene until the 1960s. In this process, acetylene and hydrogen chloride were used as shown here:
This process had disadvantages in that it was very energy-intensive and had high investment costs.
The modern chloroprene process which is currently used by nearly all makers uses butadiene differently. 1,3-Butadiene undergoes addition of chlorine across one of its double bonds in its molecule to give 3,4-dichloro-1-butene. Then this compound undergoes an elimination of a hydrogen atom in the #3 position and the chlorine atom in the #4 position as HCl forming a double bond between the #3 and #4 carbon atoms in the molecule, yielding chloroprene.
References
[Polychloroprene (CR), chloroprene rubber]
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