*** Welcome to piglix ***

Chloroprene

Chloroprene
Chloroprene
Chloroprene
Names
IUPAC name
2-Chlorobuta-1,3-diene
Other names
Chloroprene, 2-chloro-1,3-butadiene, Chlorobutadiene, β-Chloroprene
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.381
KEGG
PubChem CID
RTECS number EL9625000
Properties
C4H5Cl
Molar mass 88.5365 g/mol
Appearance Colorless liquid
Odor pungent, ether-like
Density 0.9598 g/cm3
Melting point −130 °C (−202 °F; 143 K)
Boiling point 59.4 °C (138.9 °F; 332.5 K)
0.026 g/100 mL
Solubility soluble in alcohol, diethyl ether
miscible in ethyl ether, acetone, benzene
Vapor pressure 188 mmHg (20 °C)
1.4583
Hazards
Main hazards Highly flammable, toxic.
R-phrases R45, R11, R20/22,
R36/37/38, R48/20
S-phrases S53, S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −15.6 °C (3.9 °F; 257.5 K)
Explosive limits 1.9%–11.3%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
450 mg/kg (rat, oral)
3207 ppm (rat, 4 hr)
1052 ppm (rabbit, 8 hr)
350 ppm (cat, 8 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 25 ppm (90 mg/m3) [skin]
REL (Recommended)
Ca C 1 ppm (3.6 mg/m3) [15-minute]
IDLH (Immediate danger)
300 ppm
Related compounds
Related Dienes
Butadiene
Isoprene
Related compounds
Vinyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Chloroprene is the common name for the organic compound 2-chlorobuta-1,3-diene, which has the formula CH2=CCl−CH=CH2. This colorless liquid is the 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 given by DuPont.

Chloroprene is produced in three steps from 1,3-butadiene: (i) chlorination, (ii) isomerization of part of the product stream, and (iii) dehydrochlorination of 3,4-dichlorobut-1-ene.

Chlorine adds to 1,3-butadiene to afford a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene. The 1,4-dichloro isomer is subsequently isomerized to 3,4 isomer, which in turn is treated with base to induce dehydrochlorination to 2-chlorobuta-1,3-diene. This dehydrohalogenation entails loss of a hydrogen atom in the 3 position and the chlorine atom in the 4 position thereby forming a double bond between carbons 3 and 4. In 1983, approximately 2,000,000 kg was produced in this manner. The chief impurity in chloroprene prepared in this way is 1-chlorobuta-1,3-diene, which is usually separated by distillation.

Until the 1960s, chloroprene production was dominated by the "acetylene process," which was modeled after the original synthesis of vinylacetylene. In this process, acetylene is dimerized to give vinyl acetylene, which is then combined with hydrogen chloride to afford 4-chloro-1,2-butadiene (an allene derivative), which in the presence of copper(I) chloride, rearranges to the targeted 2-chlorobuta-1,3-diene:

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


...
Wikipedia

...