Poly Halogen Compounds – Uses and its Environmental Effects

Poly Halogen Compounds – Uses and its Environmental Effects

Carbon compounds containing more than one halogen atoms are called poly halogen compounds. Some of the important poly halogen compounds are described below. They are classified as

(a) gem – dihalides

Poly Halogen Compounds img 1

(b) vic – dihalides

For Example

Poly Halogen Compounds img 2

Preparation

Poly Halogen Compounds

(a) gem – dihalides

Ethylidene dichloride (1, 1 – Dichloro ethane) is prepared by

(i) Treating acetaldehyde with PCl5

Poly Halogen Compounds img 3

(ii) Adding hydrogen chloride to acetylene

Poly Halogen Compounds img 4

(b) vic – dihalides

Ethylene dichloride (1, 2 – Dichloro ethane) is prepared by the following methods.

(i) Addition of chlorine to ethylene

Poly Halogen Compounds img 5

(ii) Action of PCl5 (or HCl) on ethylene glycol

Poly Halogen Compounds img 6

Properties

Physical Properties

  1. They are sweet smelling, colourless liquids having relatively high boiling points.
  2. The boiling point of ethylidene chloride is less than that of ethylene dichloride.

Chemical Properties

1. Hydrolysis with aqueous NaOH or KOH

Gem-Dihalides, on hydrolysis with aqueous KOH give an aldehyde or a ketone vic-Dihalides, on hydrolysis with aqueous KOH gives glycols.

Poly Halogen Compounds img 7

This reaction can be used to distinguish the gem – Dihalides and vic – Dihalides.

Poly Halogen Compounds

Reaction with Zinc (Dehalogenation)

Gem – Dihalides and vic – Dihalides on treatment with zinc dust in methanol give alkenes.

Poly Halogen Compounds img 8

Reaction with Alcoholic KOH (Dehydrohalogenation)

gem – Dihalides and vic – Dihalides on treatment with alcoholic KOH give alkynes.

Poly Halogen Compounds img 9

Methylene chloride (Di chloromethane)

Preparation

Methylene chloride is prepared by the following methods

1. Reduction of Chloroform

(a) Reduction of chloroform in the presence of Zn + HCl gives methylene chloride

Poly Halogen Compounds img 10

(b) Reduction of chloroform using H2/Ni

Poly Halogen Compounds img 11

2. Chlorination of Methane 

Chlorination of methane gives methylene chloride

Poly Halogen Compounds img 12

Poly Halogen Compounds

Uses of methylene chloride

Methylene chloride is used as

  1. Aerosol spray propellant
  2. Solvent in paint remover
  3. Process solvent in the manufacture of drugs
  4. A metal cleaning solvent

Trihaloalkane

Trihaloalkanes are compounds obtained by replacing three hydrogen atoms of a hydrocarbon by three halogen atoms.

Example

Poly Halogen Compounds img 13

1. Chloroform

Chloroform is an important trihaloalkane. Dumas named CHCl3 as chloroform as it gives formic acid on hydrolysis.

Preparation:

Chloroform is prepared in the laboratory by the reaction between ethyl alcohol with bleaching powderfollowed by the distillation of the product chloroform. Bleaching powder act as a source of chlorine and calcium hydroxide. This reaction is called haloform reaction. The reaction proceeds in three steps as shown below.

Step – 1:

Oxidation

Poly Halogen Compounds img 14

Step – 2:

Chlorination

Poly Halogen Compounds img 15

Step – 3:

Hydrolysis

Poly Halogen Compounds img 16

Poly Halogen Compounds

Properties

Physical properties

(i) Chloroform is a colourless liquid with peculiar sickly smell and a burning taste
(ii) The vapours of chloroform when inhaled it causes unconsciousness (depress the central nervous system) and hence it is used as an anaesthetic.

Chemical Properties

1. Oxidation

Chloroform undergoes oxidation in the presence of light and air to form phosgene (carbonyl chloride)

Poly Halogen Compounds img 17

Since phosgene is very poisonous, its presence makes chloroform unfit for use as anaesthetic.

2. Reduction

Chloroform undergoes reduction with zinc and HCl in the presence of ethyl alcohol to form methylene chloride.

Poly Halogen Compounds img 18

3. Nitration

Chloroform reacts with nitric acid to form chloropicrin.(Trichloro nitro methane)

Poly Halogen Compounds img 19

It used as an insecticide and soil sterilising agent.

4. Carbylamine Reaction

Chloroform reacts with aliphatic or aromatic primary amine and alcoholic caustic potash, to give foul smelling alkyl isocyanide (carbylamines).

Poly Halogen Compounds img 20

This reaction is used to test primary amine.

Tetra Haloalkane

Carbon tetrachloride is a good example for tetra haloalkane Carbon tetrachloride

Preparation

1. Chlorination of methane

The reaction of methane with excess of chlorine in the presence of sunlight will give carbon tetrachloride as the major product.

Poly Halogen Compounds img 21

2. Action of carbondisulphide with chlorine gas

Carbon disulphide reacts with chlorine gas in the presence of anhydrous AlCl3 as catalyst giving carbon tetrachloride

Poly Halogen Compounds img 22

Poly Halogen Compounds

Physical properties

  1. Carbon tetrachloride is a colourless liquid with its specific smell
  2. It is insoluble in water and soluble in organic solvents

Chemical properties

(i) Hydrolysis

Carbon tetrachloride reacts with hot water or with hot water vapour producing the poisonous gas, phosgene.

Poly Halogen Compounds img 23

(ii) Reduction

Carbon tetrachloride is reduced by iron powder in dilute HCl medium to form chloroform

Poly Halogen Compounds img 24

Freons (CFC)

The chloro floro derivatives of methane and ethane are called freons.

Nomenclature

Freon is represented as Freon-cba
Where c = number of carbon atoms – 1
b = number of hydrogen atoms + 1
a = total number of florine atoms

Example

Poly Halogen Compounds img 25

Freon – 12 is prepared by the action of hydrogen fluoride on carbon tetrachloride in the presence of catalylic amount of antimony pentachloride. This is called swartz reaction.

Poly Halogen Compounds img 26

Poly Halogen Compounds

Physical properties

(i) Freons are highly stable, unreactive, non corrosive, non toxic, easily liquefible gases.

Uses:

  1. Freons are a used as refrigerants in refrigerators and air conditioners.
  2. It is used as a propellant for aerosols and foams
  3. It is used as propellant for foams to spray out deodorants, shaving creams, and insecticides.

DDT (p, p’-dichloro diphenyl trichloro ethane)

DDT, the fist chlorinated organic pesticide was prepared in 1873, and in 1939 Paul Muller discovered the effectiveness of DDT as an insecticide. He was awarded Noble prize in medicine and physiology in 1948 for this discovery.

DDT can be prepared by heating a mixture of chlorobenzene with chloral (Trichloro acetaldehyde) in the presence of Conc.H2SO4.

Poly Halogen Compounds img 27

Uses:

  1. DDT is used to control certain insects which carries diseases like malaria and yellow fever
  2. It is used in farms to control some agricultural pests
  3. It is used in building construction as pest control
  4. It is used to kill various insects like housefly and mosquitoes due to its high and specific toxicity.

Find free online Chemistry Topics covering a broad range of concepts from research institutes around the world.

Leave a Comment