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Speight, J. G. (2002). Chemical and Process Design Handbook.New York: McGRAW-HILL.

PRODUCTION OF PHENOL AND ACETONE FROM CUMENE

MAIN PROPERTIES OF PHENOL

Other name: Hydroxybenzene

Freezing point:

Boiling point:

Density:

Flashpoint:

MAIN PROPERTIES OF ACETONE

Other name: Dimethyl ketone, 2-propanone,

Melting point:

Boiling point:

Density:

OTHER INFORMATION for PHENOL:

Phenol gradually turns pink if it contains impurities or is exposed to heat or light

It has a distinctive sweet, tarry odor, and burning taste

Phenol has limited solubility in water between and

Above , phenol and water are miscible in all proportions

Phenol is very soluble in alcohol, benzene, chloroform, ether, and partially disassociated

organics in general, but it is less soluble in paraffinic hydrocarbons

OTHER INFORMATION for PHENOL:

Simplest Ketone and is a colorless liquid that is miscible in all proportions with water, alcohol, or

ether.

PROCESS

To date, the principal process used in the production of phenols is the cumene process.

In the last few years, there has been a steady trend away from iso-propyl alcohol and towards

cumene.

Cumene would require a balancing of the market with the coproduct phenol from this process

1)

Peroxidation of cumene (iso-propyl benzene) [oxidation of cumene to hydroperoxide] at

in the presence of air and a catalyst

2)

Decomposition of the peroxide at to in the presence of sulfuric acid.

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PHENOL-ACETONE FROM CUMENE PROCESS:

Cumene is oxidized to form cumene hydroperoxide that is then concentrated and cleaved to

produce phenol and acetone

By products of the oxidation reaction:

Acetophenone

Dimethyl benzyl alcoholWhich is dehydrated in the cleavage reaction

to produce alpha-methylstyrene

1.

The hydroperoxide is made by reaction of cumene with oxygen at to until to

percent of the hydroperoxide is formed.

2.

Concentration of the hydroperoxide to is followed by catalyzed rearrangement undermoderate pressure at to .

a.

During the reaction, the palladium chloride () catalyst is reduced to elemental

palladium to produce hydrogen chloride that catalyzes the rearrangement, and

reoxidation of the palladium is brought about by use of cupric chloride () that is

converted to cuprous chloride ().

b.

The cuprous chloride is reoxidized during the catalyst regeneration cycle.

c.

The overall yield is to percent.

d.

Byproducts: Acetophenone, 2-phenylpropan-2-ol, and-methylstyrene

3.

Acetone is distilled first at boiling point .

4.

Vacuum distillation recovers the unreacted cumene and yields -methylstyrene, which can behydrogenated back to cumene and recycled.

5.

Further distillation separates phenol, boiling point , and acetophenone, boiling point

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Industrial Use of Phenol:

Formaldehyde resins

Bisphenol A

Caprolactam

Aniline

Xylenols

Alkylphenols

Phenol-formaldehyde polymers (phenolic resins) Have a primary use as adhesive in plywood

formulations.

The use of phenol in detergent synthesis to make alkylphenols is an important aspect of phenol

utility

Industrial Use of Acetone:

It is a very important solvent and is widely used in the manufacture of plastics and lacquers.

It may be used as a solvent for acetylene.

It is the starting ingredient or intermediate for numerous organic syntheses.

Used in the production of methyl methacrylate, solvents, bisphenol A, aldol chemicals, and

pharmaceuticals. Methyl methacrylate is manufactured and then polymerized to poly(methyl

methacrylate), an important plastic known for its clarity and used as a glass substitute.

Aldol chemicals refer to a variety of substances desired from acetone involving an aldol

condensation in a portion of their synthesis. The most important of these chemicals is methyl

iso-butyl ketone (MIBK), a common solvent for many plastics, pesticides, adhesives, andpharmaceuticals.

Bisphenol A is manufactured by a reaction between phenol and acetone, the two products from

the cumene hydroperoxide rearrangement. Bisphenol A is an important diol monomer used in

the synthesis of polycarbonates and epoxy resins.

A product known as synthetic methyl acetone is prepared by mixing acetone (50%), methyl

acetate (30%), and methyl alcohol (20%) and is used widely for coagulating latex and in paint

removers and lacquers.

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PRODUCTION OF CUMENE FROM BENZENE AND PROPYLENE

MAIN PROPERTIES OF CUMENE:

Other name: iso-propyl benzene

Boiling point:

Density:

Flash point:

OTHER INFORMATION:

It is an important intermediate in the manufacture of phenol and acetone.

MANUFACTURING PROCESS:

1)

Reaction of Benzene with propylene over a catalyst such as a phosphoric acid derivative at

to and to psi

*** A refinery cut of mixed propylene-propane is frequently used instead of the more expensive pure

propylene.

*** Benzene is provided in substantial excess to avoid polyalkalation.

*** The yield is near quantitative (in excess of ) based on propylene

*** Excess Benzene stops the reaction at the monoalkylated stage and prevents the polymerization of

propylene.

2)

Cumene is separated by distillation, boiling point at .

*** Other catalysts that have been used are aluminum chloride and sulfuric acid