![]() | |
![]() | |
Names | |
---|---|
IUPAC name
1,4-Dichlorobut-2-ene
| |
Other names
trans-1,4-Dichlorobutene
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.437 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
UN number | 2920 2927 2922 |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C4H6Cl2 | |
Molar mass | 124.99 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.13 g/mL |
Melting point | 1 °C (34 °F; 274 K) |
Boiling point | 125.5 °C (257.9 °F; 398.6 K) |
Hazards [1] | |
GHS labelling: | |
![]() ![]() ![]() ![]() | |
Danger | |
H301, H311, H314, H330, H350, H410 | |
P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
1,4-Dichlorobut-2-ene are organochlorine compounds with the formula ClCH2CH=CHCH2L. Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene. [2]
Chloroprene is a monomer for the production of synthetic rubbers such as Neoprene. It is produced from butadiene in a three-step process. The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene (both isomers). In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst. Finally, dehydrochlorination ( elimination of hydrogen chloride) of 3,4-dichlorobut-1-ene with dilute sodium hydroxide solution in the presence of polymerization inhibitors gives crude chloroprene. [3]
1,4-Dichlorobut-2-ene is a precursor to various heterocycles. [4]
The (E)-isomer is also one of the starting materials for the poriferic natural product sceptrin. [5]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
![]() | |
![]() | |
Names | |
---|---|
IUPAC name
1,4-Dichlorobut-2-ene
| |
Other names
trans-1,4-Dichlorobutene
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.437 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
UN number | 2920 2927 2922 |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C4H6Cl2 | |
Molar mass | 124.99 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.13 g/mL |
Melting point | 1 °C (34 °F; 274 K) |
Boiling point | 125.5 °C (257.9 °F; 398.6 K) |
Hazards [1] | |
GHS labelling: | |
![]() ![]() ![]() ![]() | |
Danger | |
H301, H311, H314, H330, H350, H410 | |
P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P281, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
1,4-Dichlorobut-2-ene are organochlorine compounds with the formula ClCH2CH=CHCH2L. Cis and trans isomers exist. These compounds are intermediates in the industrial production of chloroprene. They are main impurity in technical grade chloroprene. [2]
Chloroprene is a monomer for the production of synthetic rubbers such as Neoprene. It is produced from butadiene in a three-step process. The first step is the liquid- or vapour-phase chlorination of butadiene to a mixture of 3,4-dichlorobut-1-ene and 1,4-dichlorobut-2-ene (both isomers). In the second step, the mixture of 1,4-dichlorobut-2-ene and 3,4-dichlorobut-1-ene is isomerized to 3,4-dichlorobut-1-ene by heating to temperatures of 60–120 °C in the presence of a catalyst. Finally, dehydrochlorination ( elimination of hydrogen chloride) of 3,4-dichlorobut-1-ene with dilute sodium hydroxide solution in the presence of polymerization inhibitors gives crude chloroprene. [3]
1,4-Dichlorobut-2-ene is a precursor to various heterocycles. [4]
The (E)-isomer is also one of the starting materials for the poriferic natural product sceptrin. [5]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)