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CHE 322 - Wacker Process

The document discusses the Wacker process which is the oxidation of ethylene to ethanal using Pd(II) catalysts and water. It is an important industrial process. The reaction involves ethylene coordinating to palladium which allows nucleophilic attack by water, producing ethanal. Copper is used to recycle the Pd(II) catalyst.

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33 views14 pages

CHE 322 - Wacker Process

The document discusses the Wacker process which is the oxidation of ethylene to ethanal using Pd(II) catalysts and water. It is an important industrial process. The reaction involves ethylene coordinating to palladium which allows nucleophilic attack by water, producing ethanal. Copper is used to recycle the Pd(II) catalyst.

Uploaded by

onkgopotsemahilo
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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CHE 322

GROUP THEORY AND


ORGANOMETALLIC CHEMISTRY

Dr. N. Makuve
72919513
[email protected]
Office 237/237
ASSESSMENT

SECAT ON MOODLE
Catalysis by Organometallic Compounds

Alkene hydrogenation

Hydroformylation

Monsanto acetic acid process

Wacker process
Introduction
• The Wacker process is the oxidation of ethene by
divalent palladium to ethanal in the presence of water.

• The Wacker-Hoechst process is an example of


a homogeneous catalyst system illustrating nucleophilic
addition to alkenes.
Introduction
• Palladium chloride is the catalyst and palladium
activates coordinating ethene toward a nucleophilic
attack by water.

• Thus, the reaction is highly exothermic as one might


expect for an oxidation reaction.
Wacker process

• The Wacker process is the oxidation of olefins using


Pd(II) catalysts and is an important industrial example of
Pd(II) catalysis to produce acetaldehyde from ethylene
and water.
Ethanal
Ethanal Uses
• The Wacker process is one of the important industrial processes by
which ethylene is converted to acetaldehyde.

• This process involves the addition of oxygen to an alkene, and


the equation for the overall process can be shown as
• The reaction proceeds by the formation of a complex in which C2H4
is attached to the palladium.

• In that complex, water reacts with the coordinated C2H4 to


produce a σ-bonded CH2CH2OH (Ethyl alcohol).
• The aldehyde is formed as H+ is lost, and the palladium is
recovered.
• Reoxidation of palladium directly by oxygen is extremely slow.

• The invention of Smidt (Wacker Chemie) involved copper as the


intermediate in the recycle of divalent palladium.

• Involved copper(I/II) as the catalyst in the recycle of divalent palladium:

2Cu2+ + Pd(0) → 2Cu+ + Pd2+

2Cu+ + 1/2O2+ 2H+ → 2Cu2+ + H2O


Deprotonation of the bound water
followed by hydroxide attack onto
the bound olefin leads to β-
hydroxyl palladium intermediate
7-12

Simultaneous dissociation of
chloride and β-hydride elimination
generates the palladium–enol
complex 7-13

Insertion of the bound olefin


into the Pd–H bond results in
formation of the α-
hydroxypalladium
intermediate 7-14

Homogeneous Metal Catalysis; P.W.N.M. van Leeuwen, in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2016

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