Oil & Gas Processing

Technology
Acetone Production
Bhinitha Chandrasagaran
KKE 18005
 What is Acetone?
◆ Acetone (IUPAC name
Propan-2-one) is the
organic compound with the
formula (CH3)2CO. It is the
Simplest Ketone.
◆ Acetone serves as an
important solvent in the lab
as well as in the industry.
Properties of Acetone
 Uses of Acetone in our daily life
◆ Lacquers for automotive/furniture finishes.
◆ Cellulose acetate films and fibers.
◆ Photographic films and plates casting.
◆ Coatings and inks.
◆ Resin thinners and clean-up operations.
◆ General purpose cements.
◆ Degreasing and degumming agents.
◆ Paint, varnish, lacquer strippers.
◆ Nail polish removers.
 Acetone Production

Roughly 75% of the available acetone

is used to produce other chemicals,
and 12% is used as a solvent.
Applications range from surface
coatings, films and adhesives to
cleaning fluids and pharmaceutical
applications.
Hazard Associated When Using Acetone
KEY PLAYERS IN THE GLOBAL ACETONE
MARKET
◆ INEOS Phenol, ◆ Players are strategically
◆ Royal Dutch Shell PLC, increasing their capacities
worldwide through plant
◆ Sasol,
expansion and new acetone
◆ The Dow Chemical plant installation mainly in
Company, the Asia Pacific, to address
◆ Mitsui Chemicals, Inc., the growing regional
◆ Hindustan Organic demand for acetone.
Chemicals Limited,
◆ Honeywell International
 GLOBAL CONSUMPTION

◆ The global consumption of

acetone was estimated to
be approximately 6.1 million
tons in 2015 and is
projected to register a CAGR
of 5.0%, reaching a market
value of US$ 7.3 Bn by the
end of the forecast period
(2016-2026).
Project Demand for Acetone Production

The project demand of Acetone Supply

150
Quantity (metric tonnes)

2017, 137.7

100

50

0
2011 2012 2013 2014 2015 2016 2017 2018
Years

QUANTITY(Mt.Tons)
 Technology

◆ Acetone is produced using different methods:-

 Cumene Process for Phenol and Acetone

 By the direct oxidation of propylene using air
 By the dehydrogenation of isopropyl alcohol
 Oxidation of Butanol
 Co product of Glycerin- H2O2 process
CUMENE PROCESS
TECHNOLOGY- CUMENE PROCESS

◆ This process converts two relatively cheap starting materials, benzene

and propylene, into two more valuable ones, phenol and acetone. Other
reactants required are oxygen from air and small amounts of a radical
initiator (catalyst). Cumene process is a process of producing phenol
(C6H5-OH) and acetone (CH3-CO-CH3) from benzene (C6H6) and propene
(C3H6).
◆ It is known that cumene can be oxidized to cumene hydroperoxide and
that cumene hydroperoxide can be decomposed by various means to
provide phenol and acetone. The use of clays in catalysis is known.
◆ The present invention provides a method to produce phenol and acetone
by the decomposition of cumene hydroperoxide in the presence of a
catalyst comprising a montmorillonite acidic clay which has been
modified by a heterophony acid, or by titanium, zirconium or aluminum,
at a temperature of 20° to 150°C and a pressure of 0.1 to 7 MPa
CUMENE HYDROGEN PEROXIDE PROCESS
 ADVANTAGES AND DISADVANTAGES
Advantages of Cumene Hydroperoxide
- Heterogeneous catalytic solid acids have -
several advantages in that they are
environmentally acceptable, non- -
corrosive, non-toxic, non-volatile, easy to
handle and can be recycled
Disadvantages of Cumene Hydroperoxide
The cumene process is technically very
hard to scale industrially.
Difficulties in achieving >99.9% purity
phenol and acetone required by today's
market place due to entrainment or
breakthrough of said acids.
 ISSUES
Technical Economical Environmental

Cumene  The cumene process is  Economically, the  Many of these acid

Hydroperoxide technically very hard to
Process scale industrially.
 Difficulties in achieving
>99.9% purity phenol
and acetone required
by today's market
place due to  In addition, by-products
entrainment or
breakthrough of said
acids.
cumene process
requires the use of
expensive metals such
as Titanium as active
sites on the K-10 clay to
ensure proper process.
such as 2-phenyl-2-  Production of benzene
propanol are produced
along with the product
and must somehow be
removed and
processed.
catalysts require
substantial expenditure
for production of phenol
and acetone, there are
disposal problems with
spent acids or their
salts.
as intermediate which is
carcinogenic and might
endanger the live of
workers handling this.
OXIDATION OF
PROPYLENE
TECHNOLOGY- Oxidation of Propylene

◆ Acetone can also be produced by the direct oxidation of

propylene using air. In this process the catalysis consists of a
solution of copper chloride containing small quantities of
palladium chloride. The reaction takes place under a moderate
pressure and at 100°C. It is exothermic by 61 kcal/mole of
acetone produced. The overall reaction is as follows:

◆ 2𝐶𝐻3 − 𝐶𝐻 = 𝐶𝐻2 + 𝑂2 → 2𝐶𝐻3 − 𝐶𝑂 − 𝐶𝐻3

Propylene Oxygen Acetone
OXIDATION OF PROPYLENE PROCESS
 ADVANTAGES AND DISADVANTAGES

Advantages of Catalytic Oxidation of Propylene Disadvantages of Catalytic Oxidation of Propylene

- Does not form co-products or use expensive -
reagents
- The required energy for catalytic oxidation is
lower than that for thermal oxidation due to the -
presence of catalyst resulting in lower operating -
and/or capital cost
A high concentration of HCl aqueous solution is
used and hence choice of expensive corrosion
resistant material is required.
Pure feed of Propylene (99%) should be used
If oxygen dissolved in excess is discharged into
the gas phase, it is mixed with propylene to have
a possibility of troubles such as explosion
 ISSUES

Technical Economical Environmental

Catalytic Oxidation  Low conversion of  A high concentration of  If oxygen dissolved in
Process acetone which is lower HCl aqueous solution is excess is discharged into
than 99% used and hence choice the gas phase, it is
 Since oxygen molecule of expensive corrosion mixed with propylene to
is not directly reacted resistant material is have a possibility of
with propylene, but a required. troubles such as
complicated oxidation- explosion
reduction system is
utilized.
DEHYDROGENATION OF
ISOPROPYL ALCOHOL
(IPA)
TECHNOLOGY-Dehydrogenation of IPA

◆ In this process, an aqueous solution of isopropyl alcohol

is fed into the reactor, where the stream is vaporized and
reacted over a solid catalyst. The reactions occurring
within the reactor are as follows:
𝐶𝑢/𝐶
◆ 𝐶𝐻3 − 𝐶𝐻𝑂𝐻 − 𝐶𝐻3 𝐶𝐻3 − 𝐶𝑂 − 𝐶𝐻3 + 𝐻2
Isopropyl alcohol acetone hydrogen
◆ The primary advantage of this process is that the acetone
produced is free from trace aromatic compounds,
particularly benzene. For this reason, acetone produced
from IPA is favored by the pharmaceutical industry.
DEHYDROGENATION OF ISO PROPYL ALCOHOL
(IPA) PROCESS
 ADVANTAGES AND DISADVANTAGES

Advantages of Dehydrogenation of ISA Disadvantages of Dehydrogenation of ISA

- High purity Acetone is obtained (98%- - Optimization of the dehydrogenation
99%) plant is still being researched
- Highest quality products where only worldwide.
phenol/acetone process commercially
proven to produce pharmaceutical
grade acetone
- Low environmental impact of air and
water emissions
- Low Energy Consumption
 ISSUES

Technical Economical Environmental

Catalytic  High purity Acetone is  The integration and  In the dehydrogenation
Dehydrogenation obtained (98%-99%) process are well known of IPA, high purity
Process by process engineers, Acetone is obtained, and
therefore there is no the conversion of
need for extra acetone is high and has
professional manpower. no by-products, which
are significantly not
hazardous to health
 FUTURE ALTERNATIVES-ABE (ACETONE-
BUTANOL-ETHANOL) FERMENTATION

◆In acetone-butanol fermentation, acetone and butanol are produced from

glucose using strains of Clostridia, which are strictly anaerobic bacteria.
Further, ethanol is also produced. The ABE fermentation produces solvents
in a ratio of 3 parts acetone, 6 parts butanol to 1 part ethanol.

◆Clostridium acetobutylicum is the most well-studied and widely used

species.

Cumene process
Primary product is phenol
Acetone is by product
Purity of acetone is low
---
Conversion to acetone is low
Worldwide production method
Unconverted benzene present along
with acetone is dangerous to some
process
To purify acetone large number of
separation processes are required
which increase the production cost
Conclusion
Propylene oxidation process
Acetone is the primary product
Purity is high
Propylene used should be 99% pure
Conversion to acetone is low
Not used worldwide
Not a dangerous compound present
along with acetone
Less separation process required and Less separation process required and
production cost is low
Isopropyl alcohol dehydrogenation
process
Acetone is the primary product
Purity is high
Aqueous solution of the isopropyl
alcohol can be used
Conversion to acetone is high
Worldwide production method
Not a dangerous compound present
along with acetone
production cost is low
 CONCLUSION
◆ Major disadvantage of the production of acetone from cumene process
is that some amount of reactant benzene is present along with desired
product which is toxic.
◆ The disadvantage of production of acetone from propylene oxidation
process is that propylene required for the process should be 99 % pure.
◆ So the favorite process for the production of acetone is dehydrogenation
of isopropyl alcohol.
◆ 100 years after the first industrial exploitation of the Clostridial acetone-
butanol fermentation this process is still of high interest, commercially
as well as scientifically. It still poses many questions, holds a lot of
secrets, and many aspects have yet to be understood. Future
generations of scientists will have enough to do to understand and
optimize the underlying metabolic processes
 References
◆ Data, R. U. S. A., & Trousof, P. E. (1981). United States Patent (19) OF THE, (19).
◆ Venner, R. (2013). Recent Advances in Cumene / Phenol / Acetone Technology: Energy Efficient
Versalis / Lummus Cumene - Phenol Technology for Minimizing Operating Costs Lummus
Chemical Processes, (November).
◆ Sauer, M. (2016). Industrial production of acetone and butanol by fermentation-100 years later.
FEMS Microbiology Letters, 363(13), 1–4. https://doi.org/10.1093/femsle/fnw134
◆ Product, X., & Summary, S. (2012). Xylenes Product Stewardship Summary, (67). Retrieved from
http://s00.static-shell.com/content/dam/shell-
new/local/business/chemicals/downloads/pdf/responsible-chemistry/xylenes-product-
stewardship-summary-december-2012.pdf
◆ Tice, R., & Brevard, B. (1998). Cumene Hydroperoxide [80-15-9]. Review of toxicological literature,
(September), 1–64. Retrieved from
https://ntp.niehs.nih.gov/ntp/htdocs/chem_ background/exsumpdf/cumenehydroperoxide_ 508.
pdf%0Ahttp://ntp.niehs.nih.gov/ntp/htdocs/Chem_ Background/ExSumPdf/
CumeneHydroperoxide.pdf - 968.7KB (PDF)
Thanks!
Any questions?