Difference between revisions of "1,2-Dichloroethane"

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[[File:1,2-Dichloroethane.png|thumb|220x220px|Structure of 1,2-dichloroethane]]
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{{Chembox
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| Name = 1,2-Dichloroethane
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| Reference =
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| IUPACName = 1,2-Dichloroethane
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| PIN =
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| SystematicName =
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| OtherNames = DCA<br>DCE<br>Dutch liquid<br>Dutch oil<br>Ethane dichloride<br>Ethylene dichloride<br>Freon 150
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| ImageFileL1 = 1,2-Dichloroethane ball and stick structure.png
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| ImageSizeL1 = 140
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| ImageCaptionL1 = Ball and stick structure of 1,2-dichloroethane
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| ImageFileR1 = 1,2-Dichloroethane-0.png
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| ImageCaptionR1 = Structural formula of 1,2-dichloroethane
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| Section1 = {{Chembox Identifiers
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless liquid
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| BoilingPt =
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| BoilingPtC = 84
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 1.253 g/cm<sup>3</sup>
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| Formula = C<sub>2</sub>H4Cl<sub>2</sub>
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| HenryConstant =
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| LogP = 1.48
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| MolarMass = 98.954 g/mol
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| MeltingPt =
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| MeltingPtC = −35
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| Odor = Chloroform-like
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| pKa =
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| pKb =
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| Solubility = 0.87 g/100 ml (20 °C)
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| SolubleOther = Miscible with [[alcohol]]s, aromatics, [[ether]]s, , halocarbons, [[ketone]]s
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| Solvent =
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| VaporPressure = 78.9 mmHg at 25 °C
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| AutoignitionPt = 413 °C (775 °F; 686 K)
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| ExploLimits = 6.2-16 %
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| ExternalMSDS = [https://www.docdroid.net/y7TOVH9/12-dichloroethane-sa.pdf.html Sigma-Aldrich]
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| FlashPt = 13 °C (55 °F; 286 K)
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| LD50 = 670 mg/kg (rat, oral)
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| LC50 = 3,000 ppm (guinea pig, 7 hr)<br>1,000 ppm (rat, 7 hr)
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| MainHazards = Flammable<br>Toxic
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| OtherCompounds = [[Dichloromethane]]
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'''1,2-dichloroethane''', or '''ethylene dichloride''', is a common solvent and reagent, going by the abbreviations '''EDC''' and '''1,2-DCA'''. It is also used to make [[vinyl chloride]], the major precursor to [[polyvinyl chloride]], commonly known as PVC.
 
'''1,2-dichloroethane''', or '''ethylene dichloride''', is a common solvent and reagent, going by the abbreviations '''EDC''' and '''1,2-DCA'''. It is also used to make [[vinyl chloride]], the major precursor to [[polyvinyl chloride]], commonly known as PVC.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
Ethylene dichloride is a slightly reactive polar solvent. It is sometimes used as a precursor to [[ethylenediamine]] and [[1,1,1-trichloroethane]]<ref>http://en.wikipedia.org/wiki/1,2-Dichloroethane</ref>.
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Ethylene dichloride is a slightly reactive polar solvent. It is sometimes used as a precursor to [[ethylenediamine]].
  
 
===Physical===
 
===Physical===
−
Ethylene dichloride is colorless and has a high index of refraction, giving it a shiny appearance, similar to chloroform, which it also smells similarly to. It is a versatile solvent, though it does form [[Azeotrope|azeotropes]] with water and many other solvents.
+
Ethylene dichloride is colorless and has a high index of refraction, giving it a shiny appearance, similar to chloroform, which it also shares a similar smells. It is a versatile solvent, though it does form [[azeotrope]]s with water and many other solvents.
  
 
==Availability==
 
==Availability==
−
1,2-Dichloroethane is mostly bought from chemical suppliers rather than ordinary retail stores due to its inherent dangers. In some countries, however, it is sold in hobby stores with no questions asked as a solvent for fusing plastic parts to each other.
+
1,2-Dichloroethane is mostly bought from chemical suppliers rather than ordinary retail stores due to its inherent dangers. In some countries, however, it is sold in hobby stores with no questions asked as a solvent for fusing plastic parts to each other, most often mixed with various hydrocarbons. You can purify the compound from the mixture via fractional distillation.
  
 
==Preparation==
 
==Preparation==
−
1,2-Dichloroethane can be prepared by bubbling [[chlorine]] through [[ethene]] solution (Eg. dissolved in [[Carbon Tetrachloride]]) with a [[Iron(III) chloride]] catalyst, or bubbling [[oxygen]] through a solution of 1 molar part [[ethene]] to four molar parts [[Hydrochloric acid]] with a [[Copper(II) chloride]] catalyst. The first procedure produces pure 1,2-dichloroethane, while the second results in water as well<ref>http://en.wikipedia.org/wiki/1,2-Dichloroethane</ref>.
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The main industrial route involves the reaction of [[ethylene]] and [[chlorine]], in the presence of anh. [[iron(III) chloride]] catalyst:
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: H<sub>2</sub>C=CH<sub>2</sub> (g) + Cl<sub>2</sub> (g) → Cl-C<sub>2</sub>H<sub>4</sub>-Cl (l)
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 +
[[Carbon tetrachloride]] is used as reaction solvent.
 +
 
 +
A more accessible route involves bubbling oxygen through a solution containing ethylene and [[hydrochloric acid]]/[[hydrogen chloride]] (oxychlorination), in the presence of [[copper(II) chloride]] catalyst, process which yields dichloroethane, and water being produced as side product.
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: H<sub>2</sub>C=CH<sub>2</sub> + 2 HCl + ½  O<sub>2</sub> → Cl-C<sub>2</sub>H<sub>4</sub>-Cl + H<sub>2</sub>O
  
 
==Projects==
 
==Projects==
 
*Ethylenediamine synthesis
 
*Ethylenediamine synthesis
 
*Make PVC
 
*Make PVC
 +
*Extraction solvent
  
 
==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
−
Ethylene dichloride is toxic (by inhalation), flammable, and a [[carcinogen]]. All these hazards are amplified by the chemical's volatile nature. This chemical is also unstable when in the presence of [[aluminium]], [[zinc]], and [[iron]]<ref>http://en.wikipedia.org/wiki/1,2-Dichloroethane</ref>.
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Ethylene dichloride is toxic (by inhalation), flammable, and a [[carcinogen]]. All these hazards are amplified by the chemical's volatile nature. This chemical is also unstable when in the presence of [[aluminium]], [[zinc]] and [[iron]]<ref>http://en.wikipedia.org/wiki/1,2-Dichloroethane</ref>.
  
 
===Storage===
 
===Storage===
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Dichloroethane should be stored in closed bottles in dark well ventilated places.
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Dichloroethane should be stored in closed amber glass bottles, in dark well ventilated places.
  
 
===Disposal===
 
===Disposal===
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Dichloroethane can be neutralized with a strong alkali solution or with Fenton's reagent.
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Dichloroethane can be neutralized by reducing it with a metal powder, like iron, over the course of several days or with Fenton's reagent. Both processes release heat, which may volatilize some dichloroethane. This should be performed in a fume hood or outside.
  
 
==References==
 
==References==
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[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
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[[Category:Organochlorine compounds]]
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[[Category:Haloalkanes]]
 
[[Category:Solvents]]
 
[[Category:Solvents]]
 
[[Category:Polar solvents]]
 
[[Category:Polar solvents]]
 
[[Category:Volatile chemicals]]
 
[[Category:Volatile chemicals]]
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[[Category:Organochlorine compounds]]
 
−
[[Category:Haloalkanes]]
 
 
[[Category:Carcinogenic]]
 
[[Category:Carcinogenic]]
 
[[Category:Liquids]]
 
[[Category:Liquids]]

Latest revision as of 10:28, 27 December 2023

1,2-Dichloroethane
1,2-Dichloroethane ball and stick structure.png
Ball and stick structure of 1,2-dichloroethane
1,2-Dichloroethane-0.png
Structural formula of 1,2-dichloroethane
Names
IUPAC name
1,2-Dichloroethane
Other names
DCA
DCE
Dutch liquid
Dutch oil
Ethane dichloride
Ethylene dichloride
Freon 150
Properties
C2H4Cl2
Molar mass 98.954 g/mol
Appearance Colorless liquid
Odor Chloroform-like
Density 1.253 g/cm3
Melting point −35 °C (−31 °F; 238 K)
Boiling point 84 °C (183 °F; 357 K)
0.87 g/100 ml (20 °C)
Solubility Miscible with alcohols, aromatics, ethers, , halocarbons, ketones
Vapor pressure 78.9 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Flash point 13 °C (55 °F; 286 K)
Lethal dose or concentration (LD, LC):
670 mg/kg (rat, oral)
3,000 ppm (guinea pig, 7 hr)
1,000 ppm (rat, 7 hr)
Related compounds
Related compounds
 Dichloromethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,2-dichloroethane, or ethylene dichloride, is a common solvent and reagent, going by the abbreviations EDC and 1,2-DCA. It is also used to make vinyl chloride, the major precursor to polyvinyl chloride, commonly known as PVC.

Properties

Chemical

Ethylene dichloride is a slightly reactive polar solvent. It is sometimes used as a precursor to ethylenediamine.

Physical

Ethylene dichloride is colorless and has a high index of refraction, giving it a shiny appearance, similar to chloroform, which it also shares a similar smells. It is a versatile solvent, though it does form azeotropes with water and many other solvents.

Availability

1,2-Dichloroethane is mostly bought from chemical suppliers rather than ordinary retail stores due to its inherent dangers. In some countries, however, it is sold in hobby stores with no questions asked as a solvent for fusing plastic parts to each other, most often mixed with various hydrocarbons. You can purify the compound from the mixture via fractional distillation.

Preparation

The main industrial route involves the reaction of ethylene and chlorine, in the presence of anh. iron(III) chloride catalyst:

H2C=CH2 (g) + Cl2 (g) → Cl-C2H4-Cl (l)

Carbon tetrachloride is used as reaction solvent.

A more accessible route involves bubbling oxygen through a solution containing ethylene and hydrochloric acid/hydrogen chloride (oxychlorination), in the presence of copper(II) chloride catalyst, process which yields dichloroethane, and water being produced as side product.

H2C=CH2 + 2 HCl + ½ O2 → Cl-C2H4-Cl + H2O

Projects

  • Ethylenediamine synthesis
  • Make PVC
  • Extraction solvent

Handling

Safety

Ethylene dichloride is toxic (by inhalation), flammable, and a carcinogen. All these hazards are amplified by the chemical's volatile nature. This chemical is also unstable when in the presence of aluminium, zinc and iron[1].

Storage

Dichloroethane should be stored in closed amber glass bottles, in dark well ventilated places.

Disposal

Dichloroethane can be neutralized by reducing it with a metal powder, like iron, over the course of several days or with Fenton's reagent. Both processes release heat, which may volatilize some dichloroethane. This should be performed in a fume hood or outside.

References

  1. ↑ http://en.wikipedia.org/wiki/1,2-Dichloroethane

Relevant Sciencemadness threads

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