Topic: Wacker Process

Presented to: Dr.Abid Zia

Presented by: Neha Tariq
Wacker process

Refers to the oxidation of ethylene to acetaldehyde in

the presence of palladium(II) chloride as the catalyst.

WACKER PROCESS
Sources of oxygen

 Carbon monoxide (e.g., hydroformylation, acetic acid)

 Water
 Molecular oxygen

WACKER PROCESS
Net Reaction:

CH2=CH2 + PdCl2 + H2O  CH3C(=O)H + Pd(0) + 2HCl

Pd(0) + 2 CuCl2  PdCl2 + 2CuCl

2CuCl + 2HCl + 1/2O2  2CuCl2 + H2O

_________________________________________________

CH2=CH2 + 1/2O2  CH3C(=O)H

WACKER PROCESS
 The first reaction would be little of value since
palladium is expensive except that, in the presence of
Cu2+,palladium metal is oxidized back to Pd2+ before it
precipitates. The Cu+ produced is reoxidized by
molecular oxygen.

WACKER PROCESS
THE WACKER
PROCESS
Step a

Two Cl ions are displaced

and substituted with
alkene and H2O

WACKER PROCESS
Step b

Attack of a
nucleophile
(H2O) on the
alkene

WACKER PROCESS
Step c

Loss of Cl

WACKER PROCESS
Step d

-elimination

WACKER PROCESS
Step e

WACKER PROCESS
Step g

Regeneration of Pd(II)

WACKER PROCESS
 High Cl- concentration
-increase the solubility of Pd0
(avoid the precipitation of Pd black)
-facilitate the oxidation of Pd0 by Cu2+
-lower Pd2+ and loading Cu2+
-increase HCl formation
-increase chlorinated by products

WACKER PROCESS
Importance
 The wacker oxidation has been employed extensively
in organic synthesis.
 About 4 million pounds of aldehyde are produced
yearly by this method.
 Variants of the reaction yield aldehyde, allylic/vinylic
ethers, and allylic/vinylic amines.

WACKER PROCESS