Oxidation: by Muhammad Umar Mushtaq

OXIDATION
By
Muhammad Umar Mushtaq
INTRODUCTION
Oxidation is the addition of oxygen to an organic

compound or, conversely, the removal of hydrogen.
 Reaction control is the major issue during oxidation

reactions. Only partial oxidation is required for
conversion of one organic compound into another or
complete oxidation to carbon dioxide and water will
ensue.
DEHYDROGENATION
 From primary alcohol to an aldehyde
 From secondary alcohol to ketone

INTRODUCTION OF OXYGEN ATOM
 From aldehyde to carboxylic acid
 From hydrocarbon to alcohol

APPLICATION
 As examples of oxidation processes, two processes are
available for the manufacture of phenol, and both involve
oxidation.
 The major process involves oxidation of cumene to cumene

hydroperoxide, followed by decomposition to phenol and
acetone.
 Phenol is also made by the oxidation of toluene to benzoic

acid, followed by decomposition of the benzoic acid to
phenol.
APPLICATION
 Benzoic acid is synthesized by liquid-phase toluene oxidation
over a cobalt naphthenate catalyst with air as the oxidizing agent.
 Maleic acid and anhydride are recovered as by-products of the

oxidation of xylenes and naphthalenes to form phthalic acids, and
are also made specifically by the partial oxidation of benzene over
a vanadium pentoxide (V2O5) catalyst.
APPLICATION
 Several oxidative routes are available to change cyclohexane to
cyclohexanone, cyclohexanol, and ultimately to adipic acid.
 Acetaldehyde is manufactured by one of several possible processes:

 the hydration of acetylene, no longer a significant process.
 The Wacker process,in which ethylene is oxidized directly with air or

99% oxygen) in the presence of a catalyst such as palladium chloride
with a copper chloride promoter
 Passing ethyl alcohol over a copper or silver gauze catalyst gives a 25

percent conversion to acetaldehyde, with recirculation making a 90 to 95
percent yield possible
 A process in which lower molecular weight paraffin hydrocarbons are

oxidized noncatalytically to produce mixed compounds, among them
acetaldehyde and acetic acid.
OXIDIZING AGENTS
The most common oxidation agent is air, but oxygen is frequently used.
Other Chemical oxidizing agents include:
 Permanganates (Neutral solution, Acid solution)

 Dichromates (Chromic acid solution)
 Hypochlorous acid and salts
 Sodium chloride and chlorine dioxide
 Chlorates
 Peroxides
 Nitric acid and nitrogen tetraoxide
 Copper salt
 Fuming sulfuric acid
 Ozone
LIQUID-PHASE OXIDATION
 In the case of liquid-phase reactions in which oxidation is secured

by means of atmospheric oxygen—for example, the oxidation of
liquid hydrocarbons to fatty acids—special means must be
provided to secure adequate mixing and contact of the two
immiscible phases of gaseous oxidizing agent and the liquid being
oxidized.
 Although temperature must be controlled and heat removed, the

requirements are not severe, since the temperatures are generally
low and the rate of heat generation controllable by regulation of
the rate of air admission.
 .
LIQUID-PHASE OXIDATION
 Heat may be removed and temperature controlled by circulation

of either the liquid being oxidized or a special cooling fluid
through the reaction zone and then through an external heat
exchanger
 Mixing may be obtained by the use of special distributor inlets for

the air, designed to spread the air throughout the liquid.
VAPOR-PHASE OXIDATION PROCESSES
 The vapor-phase oxidation processes result in the concentration of

reaction heat in the catalyst zone, from which it must be removed
in large quantities at high-temperature levels.
 Removal of heat is essential to prevent destruction of apparatus,

catalyst, or raw material, and maintenance of temperature at the
proper level is necessary to ensure the correct rate and degree of
oxidation.
 With plant-scale operation removal of heat constitutes a major

problem. With limited oxidation, however, it may become
necessary to supply heat even to oxidations conducted on a plant
scale.
FORMALIN(VAPOR -PHASE
OXIDATION)
FORMALIN
Catalyst: copper,Silver or zinc oxide catalysts on wire gauze are used.

ACETIC ACID PRODUCTION
(LIQUID- PHASE OXIDATION)
The technology of acetic acid production mainly

includes ethylene oxidizing method, butane
oxidizing method, ethanol oxidizing method, etc.
PROCESSING STEPS
 Acetaldehyde is converted to acetic acid by liquid phase catalytic oxidation at a
relatively low temperature around 55 oC and at a pressure of 4.0 kgs./cm2g.

The oxygen for the reaction is supplied by atmospheric air. The heat of reaction
is removed by cooling water.
 The vent gases mainly consisting of Nitrogen are first scrubbed with crude acid
and then washed with water to remove any traces of acid carried by vent gases.
 The over flow from the reactor is sent to a stripping column where unconverted
acetaldehyde is recovered.
 The stripped crude acid along with liquid from wash column is sent to a
distillation column to get pure acetic acid from the bottom.
BATCH PROCESS

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OXIDATION

Oxidation is the addition of oxygen to an organic

 Reaction control is the major issue during oxidation

 From primary alcohol to an aldehyde

 From secondary alcohol to ketone

 From aldehyde to carboxylic acid

 From hydrocarbon to alcohol

 The major process involves oxidation of cumene to cumene

 Phenol is also made by the oxidation of toluene to benzoic

 Maleic acid and anhydride are recovered as by-products of the

 Acetaldehyde is manufactured by one of several possible processes:

 The Wacker process,in which ethylene is oxidized directly with air or

 Passing ethyl alcohol over a copper or silver gauze catalyst gives a 25

 A process in which lower molecular weight paraffin hydrocarbons are

Other Chemical oxidizing agents include:

 Permanganates (Neutral solution, Acid solution)

 In the case of liquid-phase reactions in which oxidation is secured

 Although temperature must be controlled and heat removed, the

 Heat may be removed and temperature controlled by circulation

 Mixing may be obtained by the use of special distributor inlets for

 The vapor-phase oxidation processes result in the concentration of

 Removal of heat is essential to prevent destruction of apparatus,

 With plant-scale operation removal of heat constitutes a major

Catalyst: copper,Silver or zinc oxide catalysts on wire gauze are used.

The technology of acetic acid production mainly

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