Chloroacetyl chloride

 

Chloroacetyl chloride

Chemical formula	C2H2Cl2O
OTP appearance	pale yellow liquid
Molar Mass(g/mol)	112.94
Density(g/cc)	1.42
Melting Point(°C)	-22
Boiling Point(°C)	106
Solubility in water(g/L)	Reacts
NFPA 704	1 3 0

Uses

Other

• Key (bifunctional) chemical reagent

Natural occurrence

• does nor occur naturally

Production

Synthesis

chlorinating chloroacetic acid

Various methods of chlorinating chloroacetic acid include:

• Via dichlorocarbonyl

  ClCH₂COOH + COCl₂

  {dimethyl formamide

  →

  }

  ClCH₂COCl + HCl + CO₂

• Via thionyl chloride

  ClCH₂COOH + SOCl₂ → ClCH₂COCl + HCl + SO₂

• Via chlorine

  ClCH₂COOH + Cl₂

  {H₂SO₄

  →

  }

  ClCH₂COCl + HCl

chlorination of ethenone

cold

Bubble ethenone and chlorine gas through liquid sulfur dioxide

CH₂CO + Cl₂

{SO₂(l)

→

-32°C}

ClCH₂COCl

hot

Combine ethenone and chlorine gas in an oil-cooled reaction chamber keeping the temperature between 180 and 190°C. This is best accomplished by keeping the oil between 120 and 140°C.

CH₂CO + Cl₂

{

→

180-190°C}

ClCH₂COCl

See Also

• Chloroacetic acid
• Acetyl chloride
• Agreda, Victor H; Zoeller (1993) "Acetic Acid and its Derivatives"; pp299-300.
  Marcel Dekker
  ISBN: 0-8247-8792-7