UNIVERSITI TEKNOLOGI MARA

FAKULTI KEJURUTERAAN KIMIA

INTERGRATED PROJECT
IPO200
NAME

: 1. AL AKMAL BIN KAMARUZAMAN (201381722)

2. ABDUL HAFIZ BIN ABDUL LATIF (201382012)
3. AHMAD SIDDIQ BIN MOHD SANI (201347436)
4. AINI SHAFINAZ BINTI AHMAD AZMI (2013211436)
5. AININA BINTI KAMALRULZAMAN (2013623026)

FALKULTI
SEMESTER
PROGRAMME / CODE

: KEJURUTERAAN KIMIA
:2
: EH 2202A

SUBMIT TO

: PN NURLIZAH

INTRODUCTION
PROCESS SELECTION
RAW MATERIAL
RAW MATERIAL SUPPLY &
PRODUCTION RATE
IDENTIFICATION CHEMICAL
COMPONENT & COMPOSITION

Checked by :

---------------------------

Date :

INTRODUCTION

Acetone is a colourless, mobile, flammable organic compound with the formula (CH)CO. t
is also the simplest example of the ketones. The characteristic of acetone is, it is miscible with
water, serves as an important solves and the choice of solvent for cleaning purposes in the
laboratory. However, more than 3 billion kilograms are produced annually. It is mainly used
as a precursor to polymers. Acetone is widely used is our daily life as the active ingredient in
nail polish remover, paint thinner, sanitary cleaner. Before the World War II, acetone was
produced from calcium acetate which was imported from Germany, Austria and United States.
Some acetone was produced at the plant at Kings Lynn using potato as substrate but
production was relatively inefficient. Therefore, other method was used to produce acetone
such as ABE fermentation, Cumene method and dry distillation of acetates.
Acetone is a product from cumene process when the raw materials are benzene and propylene.
Cumene process is named as the intermediate material during the process which is isopropyl
benzene (cumene). Phenol and acetone is most valuable material product from cumene
process after converts the cheap materials, benzene and propylene. Oxygen from air and small
amounts of radical initiator is required for other reactants. Most of the worldwide production
of acetone is now based on this process.
ABE fermentation is one of the process to produce acetone that uses bacterial fermentation.
The process is anaerobic (done in the absence of oxygen), similar to how yeast ferments
sugars to produce ethanol for wine, beer, or fuel. During the planned market era, because of
the cheap price of grain and the unavailability of self-made chemical synthesis equipment,
acetone and butanol were mainly produced by the fermentative method to meet the domestic
requirements, and the balance between supply and demand could be approximately reached.
The ABE fermentation is a batch process.

I.

PROCESS SELECTION

The most common method used in production of acetone in industry is acetone-butanolethanol (ABE) fermentation and cumene process. Based on this process, we have decided to
choose the best process in production of acetone. This process requires many advantages and
disadvantages in producing acetone. Acetone has a higher usage in industry, therefore the
process that has more production rate within time required of acetone will be considered.
Firstly, ABE fermentation process produces these solvents in a ratio of 3-6-1, or 3 parts
acetone, 6 parts butanol and 1 part ethanol. In Russia maize, wheat and rye served as the raw
material for AB fermentation but was substituted to other substance. The ABE fermentation
have low reactor productivity and costly. One of the raw materials used for this process is
Clostridium acetobutylicum. It produced yields of around 25 to 26% based on dry-weight
corn equivalent. As the price of raw material increased, the fermentation route was unable to
compete with the synthetic route. The temperature during the process is between the range 60120C. The problem of this process are low solvent concentrations, yield and productivity;
unfavourable solvents contents or ratio; high cost for product purification and wastes
treatment.
As a conclusion, ABE fermentation is suitable for the production of butanol since it produce
more butanol compare to acetone at the end of the process.

Besides that, cumene process is one of the industrial processesto produce acetone and phenol
from benzene and propylene. This process converts two relatively cheap starting materials
which is benzene and propylene into two more valuable materials such as acetone and phenol.
In this cumene process, we decided to only focus on the production rate of acetone which is
useful in industry and has high demand.
The first step of cumene process is the alkylation of benzene. Thus, the propylene is added to
benzene and reacted using 1% by mass of phosphoric acid as a catalyst. Cumeneis yielded in
this process and it will oxidize when it mixed with oxygen. The oxidation reaction will
produce cumenehydroperoxide. At the acidifier, cumenehydroperoxide is converted to acetone
and phenol in the presence of sulphuric acid. Acetone is purified by centrifugal separator,
physically and extractive distillation. The unit heats, vaporizes and superheats the feed is
235oC at pressure 2.2 bar. The exit pressure is 1.9 bar and the reaction occurs at 350oC.

Acetone produces by cumene will up to 83% in this process. Besides, 99.9 mol% purity of
acetone is obtained from this process through purification treatment. Thus, the production rate
is 15,000 up to 300,000 metric tons/year which is the overall yield of acetone is 97.7%. There
are many catalyst uses in this process such as phosphoric acid, sulphuric acid, AlCl3, inorganic
and organic acids, silicates, metallic oxides such as Al 2O3 and TiO2, phosphorous compound
such as PCl3, and sulfonated phenol formaldehyde resins and sulfonated styrene resins.
As conclusion, we decided to choose cumene process as a process in production of acetone.
This is because the cumene process has higher percentage yield of acetone compare to ABE
fermentation. Therefore, the raw material use in cumene process is cheaper. The temperature
and pressure use is suitable for production of acetone. Thus, the acetone produces is high
purities than ABE fermentation which is cumene process required purification process. The
batch ABE fermentation process suffered from a number of major shortcomings such as the
price of raw materials increased. Besides that, ABE fermentation process resulted in relatively
low solvent yields and in the production of solvent ratios which were not always desirable.
The fermentation process was quite complex and hard to handling, treatment and processing.
Therefore, cumene process is the best process in production of acetone and phenol where this
material is useful in industry of worldwide.

II.

Raw Material

Cumene Process: The properties of the process to produce acetone.

Since 1970s, the producer of acetone has adapted the new process to produce the acetone,
which is the cumene process. Eventhough this process will produce acetone and phenol as a
product, it still consider better than the old process to produce acetone. For example the
acetone -butanol-ethanol fermentation. The raw material for this process is called cumene
which is the common name for the isopropylbenzene. In simpler words, the cumene is
produce by the Friedel-Crafts Alkylation method of benzene with propylene (IUPAC name:
Propene). It will attach the alkyl halide to the aromatic ring of benzene and remove the halide
only if strong lewis acid is present.

Benzene

Propylen
e

C 9 H 12

The molecular mass of isopropylbenze is 120.19 g/mol and molecular formula of

. It
only dissolve in organic solvent such as ethanol and do not dissolve in water. According to
Alfa Aesar (2013, pp 13-14) the boling point of cumene is 154 celcius while the melting
point is -96.

The next step in the production is the oxidation of isopropylbenzene to produce cumene
peroxide. In alkyl group that attach to the benzene, there is one carbon that attach to only one
hydrogen, therefore it rich in electron and the adding of oxygen will occur at the carbon. The
reason the oxygen can be inserted is because the carbon-hydrogen bond is weaker than the
carbon-carbon bond. (In unit 1 from PFD)

The cumene peroxide will be hydrolysis (In unit 2 from PFD). The hydrogen will goes to the
electron that rich in electron which is the O-O bonding. However, it will cause the oxygen to
bear positive charges which against the law. Therefore the phenyl or one of the methyl group
have to migrate to overcome the oxygen positive charges. The phenyl will be the one that has
highest migrating amplitude because it is the largest in size, more electron donating. The
phenyl will bond to the oxygen atom that has the neutral charge as the positive oxygen pulling
the electron from it. Therefore the molecule can set off and there will be carbocation that
would be form as a result from the migrating of the phenyl ring. During this process, the
pressure is between 1 to 7 atm and the temperature is keep mild between 70 to 80 celcius.

The oxygen has a lone pair after the water goes off. Therefore it will form the double bond
with the carbon. However, the problem is the it will cause the oxygen to have . positive
charge, therefore the carbon will donate the electron and become the carbocation. Then it will
undergo further hydrolysis, therefore the carbon will get the hydroxide ion and the oxygen
will get the hydrogen ion. The oxygen now have the positive charge so it must leave to have a
neutral charge and form the phenol. The carbon the will have the positive charge, in order to
be neutral it must remove one hydrogen. Therefore the hydroxide ion will separate leaving
only oxygen to form the double bond with carbon. It is the acetone that been produced. To
further increase the purity of the acetone, it will be put through distillation column.

III. Raw Material supply & production rate

Acetone is used for solvent, chemical intermediate, medical, cosmetics uses,

domestic, other niche uses and used in laboratory. As it has many uses, it is estimated in 2010,
about 6 million tonnes were produced worldwide. To achieve this marketability and demand,
an enough production rate must be obtain. There is about 0.62 tonnes of acetone are produced
per ton of phenol. 0.872 tonnes and 0.47 tonnes will produce 1.31 tonnes of cumene. By
calculation, 694.44 tonnes per hour of acetone need to be produce to meet the world demand.
Production of acetone is through cumene process but it is coproduced with phenol. In this
process, propylene and benzene react in the presence of acid-based catalyst. The cumene is
oxidised in the liquid phase to cumenehydroperoxide and then cleaved in the presence of
sulphuric acid to phenol and acetone. Basically the raw material for production of acetone is
propylene and benzene. Benzene can be obtain from Nantong Runfeng Petro-Chemical Co.,
Ltd with $1000 3000 per tonne. While propylene can be obtain from Henan Rhonda Imp. &
Exp. Trading Co., Ltd with $1000 1370 per tonne.

http://www.icis.com/resources/news/2007/11/01/9074860/acetone-production-andmanufacturing-process/
http://core.theenergyexchange.co.uk/agile_assets/652/PANDIA_SI_GROUP.pdf
http://en.wikipedia.org/wiki/Acetone#Production
http://www.alibaba.com/showroom/propylene.html

IV. Identification of chemical component & compositions

1. Oxidizer
2. Acidifier
3. Seperator
4. Wash Tower
5. Acetone column
6. Distillation Column

Chemical compound & composition

Compound (wt % )
Cumene
Acetone

% Composition
76
8

Further Reaction

Phenol
Acetophenone
methyl styrene
Catalyst

14
0.4
1.6

H2SO4 / acidified bentonite clay (more economical) 500ppm by

mass
This process is clasiified as exorthermic reaction.
Since process
From unit 1 2 H= -117kJmo
From 2 3 H=-252kJmo

Source:http://essentialchemicalindustry.org/chemicals/phenol.html
http://enggyd.blogspot.com/2010/07/cumene-peroxidationprocess.html