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2-Chloro-1,3-butadiene

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Name

2-Chloro-1,3-butadiene

EINECS 204-818-0
CAS No. 126-99-8 Density 0.923 g/cm3
PSA 0.00000 LogP 1.92490
Solubility N/A Melting Point -130 °C
Formula C4H5Cl Boiling Point 59.399 °C at 760 mmHg
Molecular Weight 88.5367 Flash Point -8.827 °C
Transport Information UN 1993 Appearance clear colorless liquid
Safety 16-45-53-36/37-7 Risk Codes 10-20/22-36-48/20-36/37/38-11-45-39/23/24/25-23/24/25
Molecular Structure Molecular Structure of 126-99-8 (2-Chloro-1,3-butadiene) Hazard Symbols FlammableF, ToxicT
Synonyms

2-Chlorobutadiene;Chloroprene;NSC 18589;b-Chloroprene;

Article Data 78

2-Chloro-1,3-butadiene Synthetic route

689-97-4

3-buten-1-yne

A

25790-55-0

4-chloro-1,2-butadiene

B

126-99-8

chloroprene

Conditions
ConditionsYield
With hydrogenchloride; calcium chloride
With hydrogenchloride; calcium chloride
689-97-4

3-buten-1-yne

126-99-8

chloroprene

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride; pyrographite; mercury at 90℃;
689-97-4

3-buten-1-yne

A

126-99-8

chloroprene

B

926-57-8

1,3-dichloro-2-butene

Conditions
ConditionsYield
With hydrogenchloride; ammonium chloride; copper(l) chloride at 30℃;
With hydrogenchloride; ammonium chloride; copper(l) chloride at 30℃;
With hydrogenchloride; ammonium chloride; copper(l) chloride at 30℃;
4461-41-0

2-chloro-but-2-ene

126-99-8

chloroprene

Conditions
ConditionsYield
With chlorine at 500 - 515℃; Leiten durch ein Kohlerohr;
75-01-4

chloroethylene

126-99-8

chloroprene

Conditions
ConditionsYield
at 500℃;
at 500℃; Pyrolysis;
1790-22-3

1,2,4-trichlorobutane

A

310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

B

126-99-8

chloroprene

Conditions
ConditionsYield
With sodium hydroxide at 190℃;
10403-60-8

2,2,3-trichloro-butane

126-99-8

chloroprene

Conditions
ConditionsYield
at 400 - 510℃; beim Leiten durch Roehren aus Pyrexglas, Quarz, nichtrostendem Stahl oder Kupfer;
With pyrographite; barium(II) chloride at 300℃;
With water; silica gel; magnesium sulfate; magnesium chloride at 280 - 300℃;
With pyrographite; barium(II) chloride at 300℃;
at 400 - 510℃; beim Leiten durch Roehren aus Pyrexglas, Quarz, nichtrostendem Stahl oder Kupfer;
10403-60-8

2,2,3-trichloro-butane

A

51157-81-4

1,1-dichloro-but-2-ene

B

126-99-8

chloroprene

Conditions
ConditionsYield
at 400 - 510℃;
at 400 - 510℃;
7013-11-8

2,3-dichlorobut-1-ene

126-99-8

chloroprene

Conditions
ConditionsYield
at 530℃; Leiten durch ein Quarzrohr;
7013-11-8

2,3-dichlorobut-1-ene

A

689-97-4

3-buten-1-yne

B

126-99-8

chloroprene

Conditions
ConditionsYield
at 530℃; im Quarzrohr;

2-Chloro-1,3-butadiene Chemical Properties

The Molecular formula of Chloroprene(126-99-8): C4H5Cl
The Molar mass of Chloroprene(126-99-8): 88.5365 g/mol
The Structure:
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
Flash point: -15.6°C
Solubility in water: 0.026 g/100 mL, liquid.
Other names: Chloroprene; 2-Chloro-1,3-butadiene
Chloroprene(126-99-8) has the formula CH2=CCl-CH=CH2, which is colorless liquid. It is the common name for the organic compound 2-chloro-1,3-butadiene.

2-Chloro-1,3-butadiene Uses

Chloroprene(126-99-8) is the monomer for the production of the polymer polychloroprene, a type of synthetic rubber.

2-Chloro-1,3-butadiene Production

Chloroprene(126-99-8) is, chemically, a chlorovinyl ester of hydrochloric acid and can be manufactured by polymerizing acetylene to vinyl acetylene using a weak solution containing ammonium chloride (NH4Cl), cuprous chloride (Cu2Cl2), and potassium chloride (KCl) as catalyst. The off-gas from the reactor has its water condensed out and is then fractionated. Aqueous hydrochloric acid at 35 to 45℃ is then reacted with the vinyl acetylene in the presence of cupric chloride to give chloroprene (2-chloro-1,3-butadiene).
            2HC≡CH → CH2=CHC≡CH
       CH2=CHC≡CH + HCl → CH2=CHClC=CH2
The contact time is about 15 seconds with a 20 percent conversion per pass. An overall yield of approximately 65 percent can be achieved.
Chloroprene(126-99-8) is also made by chlorination of butadiene at 300℃ followed by dehydrochlorination, using sodium hydroxide at 100℃. Addition of the chlorine to the butadiene occurs at either 1,2 or 1,4 because the intermediate allyl carbocation is delocalized.
      CH2=CHCH=CH2 + Cl2 → CH2ClCH=CHCH2Cl
     CH2ClCH=CHCH2Cl + Cl2 → CH2=CHC(Cl)=CH2

2-Chloro-1,3-butadiene Toxicity Data With Reference

RTECS number: EL9625000

2-Chloro-1,3-butadiene Safety Profile

Hazard Codes: F,T
Risk Statements: 10-20/22-36-48/20-36/37/38-11-45-39/23/24/25-23/24/25
10: Flammable 
20/22: Harmful by inhalation and if swallowed
36:  Irritating to the eyes 
48/20:  Harmful: danger of serious damage to health by prolonged exposure through inhalation 
36/37/38:  Irritating to eyes, respiratory system and skin 
11:  Highly Flammable 
45:  May cause cancer 
39/23/24/25:  Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
23/24/25:  Toxic by inhalation, in contact with skin and if swallowed
Safety Statements: 16-45-53-36/37-7
16:  Keep away from sources of ignition - No smoking 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
53:  Avoid exposure - obtain special instruction before use 
36/37:  Wear suitable protective clothing and gloves 
7:  Keep container tightly closed
HazardClass: 3.1
PackingGroup: I

2-Chloro-1,3-butadiene Specification

The 1,4-dichloro isomer can be isomerized to the 1,2-dichloro isomer by heating with cuprous chloride.
        CH2ClCH=CHCH2Cl → CH3CH2CCl=CHCl

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