ASSIGNMENT

Submitted to: Ms Zahra khan

Submitted by: M Anees ur Rehman BEC-Sp11-040

Context: Iodoform Chemical & Physical Properties

Date: 17 April 2012

IODOFORMS
Iodoform is usually made via the haloform reaction, which can be done on any methyl ketone, and molecular iodine, which forms the triiodo methyl ketone in situ. When the triiodo methyl ketone is treated with hydroxide, iodoform is formed along with the carboxylate. Using acetone (C3H6O) as a starting material, the overall reaction is: C3H6O + 3I2 + NaOH --> CHI3 (Iodoform) + NaC2H3O2 + 3HI.

PREPARATION OF IODOFORM
Industrial preparation:
Iodoform is prepared on large scale by electrolysis of a solution containing ethanol, sodium carbonate and potassium iodide. The iodine set free, combine with ethanol in presence of alkali to form iodoform. The electrolysis carried out in presence of and the temperature is maintained at 60-70C.

K+ + e > K

2I > I2 + 2e

K + H2O > KOH + 1/2 H2 KOH is neutralised by CO2: C2H5OH + 4 I2 + 3Na2CO3 > CHI3 + HCOONa + 5 NaI + 3CO2 + 2H2O

Laboratory preparation :
From Ethanol: CH3CH2OH + I2 > CH3CHO + 2HI Acetaldehyde CH3CHO + 3I2 > Cl3CHO + 3 HI

Iodol Cl3CHO + KOH > CHI3 + HCOOK Tri-iodoacetal dehyde Iodoform Pot.formate From Acetone: CH3COCH3 + 3I2 > Cl3COCH3 + 3 HI Tri - iodoacetone

CI3COCH3 + KOH > CHI3 + CH3COOK Iodoform Pot.acetate

PHYSICAL PROPERTIES
As Iodine is toxic, it may be fatal if swallowed or inhaled. Harmful by inhalation and through skin absorption. Readily absorbed through skin. Very destructive of mucous membranes and upper respiratory tract, eyes and skin. Iodoform is harmful by ingestion, inhalation and through skin contact. Eye, skin and respiratory irritant. Physical properties of iodoform are as under: Molecular weight | 393.732 g/mol Phase | solid (at STP) Melting point | 119.5 C Boiling point | 218 C Density | 4.008 g/cm^3 Vapor pressure | 0.034 mmHg (at 25 C) Refractive index | 1.786 Specific heat capacity c_p | gas | 0.1905 J/(g K) Specific heat of formation Delta_fH | gas | 0.6375 kJ/g

| Solid | -0.46 kJ/g Specific heat of vaporization | 0.119 kJ/g | Specific heat of combustion | 1.72 kJ/g | Specific heat of fusion | 0.04175 kJ/g | Critical temperature | 858 K | Critical pressure | 5.63 MPa | (At STP)

Chemical Reactions of iodoform

KOH CHI3 > HCOOK Hydrolysis Potassium formate Reduction CHI3 > CH2I2 Red P/HI Methylene iodide Heating CHI3 > CH CH Ag powder Acetylene CHI3 > C6H5NC Carbylamine reaction Phenol C6H5NH2 + KOH (alc.) isocyanide CHI3 > Iodine vapours, Heating alone 4CHI3 + 3O2 > 4CO (Less stable than CHCl3) CHI3 > + 6I2 + 2H2O With AgNO3 Yellow precipitate of AgI (This reaction is not given by chloroform)