Acetyl chloride: How do you make Acetyl Chloride? | Properties | Uses

Laboratory Method

Preparation of Acetyl chloride

By the Reaction of acetic acid and PCl₅ or PCl₃: In the laboratory acetyl chloride is made by reaction of phosphorus tri chloride or penta chloride on Glacial acetic acid.

3CH₃COOH + PCl₃ → 3CH₃COCl + H₃PO₃

CH₃COOH + PCl₅ → CH₃COCl + POCl₃ + HCl

A distillation flask of 500 ml capacity contains approximately 40 ml of glacial acetic acid. With the help of a cork with hole in the flask, a dropping funnel is attached and the distillation flask attaches to the condenser and receiver.

The receiver has a lateral tube filled with anhydrous calcium chloride that absorbs the hydrogen chloride produced in the reaction and does not allow the water vapor of the outside air to reach inside.

The point funnel fills approximately 25 ml of phosphorus tri chloride. The distillation flask is heated to about 45°C by placing it on a water heater. By doing this, all the hydrogen chloride gas formed in the reaction is removed. After that heat the flask to about 55°C.

At this temperature, acetyl chloride is distilled and collected in the receptor. Re-distillation gives pure acetyl chloride.

• 
  Daily use Chemical Compounds and Their Properties
  
• 
  Hard Water and Soft Water : Permutit and Anion Exchange Resins
  
• 
  Properties of Water :- Purification, Sources and Uses
  
• 
  Hydrogen Chloride : Preparation, Properties and Uses
  
• 
  Washing Soda and Baking Soda : Difference and Properties
  
• 
  Electric Cell, Terminal Potential difference, EMF and Internal Resistance
  
• 
  Electrochemistry : Electrolytic cell, Mechanism and Cell Structure
  
• 
  Dalton's law of partial pressure || Numeric Example
  

The point funnel fills approximately 25 ml of phosphorus tri chloride. The distillation flask is heated to about 45°C by placing it on a water heater. By doing this, all the hydrogen chloride gas formed in the reaction is removed. After that heat the flask to about 55°C.

At this temperature, acetyl chloride is distilled and collected in the receptor. Re-distillation gives pure acetyl chloride.

By the Reaction of acetic acid and Thionyl chloride: Acetyl chloride is also obtained by the action of acetic acid and thionyl chloride.

CH₃COOH + SOCl₂ → CH₃COCl + SO₂ + HCl

Industrial Production:

By the action of calcium acetate and sulfuryl chloride: acetyl chloride is obtained by distillation of anhydrous calcium acetate with sulfuryl chloride.

(CH₃COO)₂Ca + SO₂Cl₂ → 2CH₃COCl + CaSO₄

Physical Properties

It is a colorless and pungent liquid. Its boiling point is 52°C and relative density is 1.104. It decomposes quickly by water, so it absorbs the water vapor of the air and decomposes to form hydrogen chloride.

For this reason, leaving it open in the air, the smoke of hydrogen chloride gas comes out. It is soluble in ether, acetone and acetic acid.

Acetyl Chloride Chemical Properties

Water decomposition: It decomposes quickly by water and forms acetic acid and hydrogen chloride.

CH₃COCl + HOH → CH₃COOH + HCl

Acetylation: When oxygen in a compound is displaced by the hydrogen atom acetyl group(-COCH₃) attached to nitrogen or sulphur atoms, this reaction is called acetylation. Acetylation is mainly done by reaction with acetyl chloride.

Example:

Reaction with Alcohol: It makes ester by reacting with alcohol.

CH₃COOCl + HOC₂H₅ → CH₃COOC₂H₅ + HCl

Reaction with Ammonia: It reacts with ammonia to produce acetamide.

CH₃COCl + HNH₂ → CH₃CONH₂ + HCl

Action from primary and secondary amines: It forms N –
substituted amide by acting with these amines.

CH₃COCl + HNHC₂H₅ → CH₃CONHC₂H₅ + HCl

CH₃COCl + HN(C₂H₅)₂ → CH₃CON(C₂H₅)₂ +HCl

Action from hydrazine hydroxyl amine and urea: It makes acetyl derivative by acting separately from them.

CH₃COCl + HNHNH₂ → CH₃CONHOH₂ + HCl

CH₃COCl + HNHOH → CH₃CONHOH + HCl

CH₃COCl + HNHCONH₂ → CH₃CONHCONH₂ + HCl

• 
  Importance of Biomolecules in Life || What are the 4 main biomolecules?
  
• 
  Resonance effect or mesomeric effect || What is resonance effect with example?
  
• 
  Valency of Elements || How to Find Valency || What is the Valency of the atom?
  
• 
  Glucose Structure: Physical and chemical properties, Glucose Chemical Reaction
  
• 
  Introduction of Inductive-Effect || How does Inductive Effect Work?
  
• 
  IUPAC Name : How to find the IUPAC name of compounds.
  
• 
  What is Urea || How to make Urea Fertilizer, || Urea uses
  
• 
  Sodium Chloride Properties || Why Sodium Chloride is Soluble in Water
  

Reaction with anhydrous sodium acetate: It forms acetic anhydride when heated with anhydrous sodium acetate.

CH₃COCl + CH₃COONa → (CH₃CO)₂O + NaCl

Reduction: It is reduced by hydrogen in the presence of palladium containing barium sulphate to form acetaldehyde. This reaction is called Rosenmund Reduction.

CH₃COCl + H₂ → CH₃CHO + HCl

It is reduced by lithium aluminium hydride (LiAlH4) to form ethanol.

CH₃COCl → CH₃CH₂OH + HCl

The above reduction can also be done by H₂ / Ni, Na / alcohol or NaBH₄.

Friedel-Crafts reaction: It reacts with benzene in the presence of anhydrous aluminium chloride to form acetophenone.

C₆H₅H + ClCOCH₃ → C₆H₅COCH₃ + HCl

Grignard reagent: It reacts with Grignard reagents to form methyl ketone.

CH₃COCl + ClMgCH₃ → CH₃COCH₃ + MgCl₂

Reaction with Ether: It reacts with di ethyl ether in the presence of anhydrous zinc chloride to form ethyl chloride and ethyl acetate.

CH₃COCl + C₂H₅OC₂H₅ → C₂H₅Cl + CH₃COOC₂H₅

Acetyl Chloride Uses

To find the number of -OH and -NH₂ groups in carbonic compounds.

In the making of acetic anhydride, acetamide, acetaldehyde and other carbonic compounds

As acetylating reagent in the manufacture of dyes and medical

As reagent in the laboratory.