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| CAS No.: | 126-99-8 |
|---|---|
| Name: | 2-Chloro-1,3-butadiene |
| Article Data: | 78 |
| Molecular Structure: | |
|
|
|
| Formula: | C4H5Cl |
| Molecular Weight: | 88.5367 |
| Synonyms: | 2-Chlorobutadiene;Chloroprene;NSC 18589;b-Chloroprene; |
| EINECS: | 204-818-0 |
| Density: | 0.923 g/cm3 |
| Melting Point: | -130 °C |
| Boiling Point: | 59.399 °C at 760 mmHg |
| Flash Point: | -8.827 °C |
| Appearance: | clear colorless liquid |
| Hazard Symbols: |
 F,  T
|
| Risk Codes: | 10-20/22-36-48/20-36/37/38-11-45-39/23/24/25-23/24/25 |
| Safety: | 16-45-53-36/37-7 |
| Transport Information: | UN 1993 |
| PSA: | 0.00000 |
| LogP: | 1.92490 |
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| Conditions | Yield |
|---|---|
| With hydrogenchloride; calcium chloride | |
| With hydrogenchloride; calcium chloride |
| Conditions | Yield |
|---|---|
| With hydrogenchloride | |
| With hydrogenchloride; pyrographite; mercury at 90℃; |
| Conditions | Yield |
|---|---|
| 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℃; |
| Conditions | Yield |
|---|---|
| With chlorine at 500 - 515℃; Leiten durch ein Kohlerohr; |
| Conditions | Yield |
|---|---|
| at 500℃; | |
| at 500℃; Pyrolysis; |
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 190℃; |
- 10403-60-8
2,2,3-trichloro-butane
- 126-99-8
chloroprene
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| at 400 - 510℃; | |
| at 400 - 510℃; |
| Conditions | Yield |
|---|---|
| at 530℃; Leiten durch ein Quarzrohr; |
| Conditions | Yield |
|---|---|
| at 530℃; im Quarzrohr; |
- Total:25 Page 1 of 1 1
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Chemistry
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.
Uses
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
Toxicity Data With Reference
Safety Profile
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
Specification
The 1,4-dichloro isomer can be isomerized to the 1,2-dichloro isomer by heating with cuprous chloride.
CH2ClCH=CHCH2Cl → CH3CH2CCl=CHCl