College of Science Departement of Chemistry Industrial Chemistry Two Group-4 PPT On Production of Ethylene Oxide Group Members 1

COLLEGE OF SCIENCE
DEPARTEMENT OF CHEMISTRY
INDUSTRIAL CHEMISTRY TWO
GROUP-4 PPT ON PRODUCTION OF ETHYLENE OXIDE
GROUP MEMBERS
NAME ID
1, FIKERE’AB HABTAMU 1201706
2,WELELAW MARIE 1203237
3, REDIET BOGALE 1202751
4, EPHEREM ADDISE 1201563

5,SORE ADDISU 1202999
Submitted to Dr Tehetena
ETHYLENE OXIDE
 HISTORY OF ETHYLENE OXIDE PRODUCTION
• Production of ethylene oxide began in 1914 by the chlorohydrin process, the
main method used until 1937, in which ethylene chlorohydrin is converted to
ethylene oxide by reaction with calcium oxide. The production of ethylene
chlorohydrin resulted in the formation of two main organochlorine by-
products, 1,2-dichloroethane and bis(2-chloroethyl)ether. Ethylene
chlorohydrin was produced in either the same or a separate unit and was
pumped over to the ethylene oxide production sector. The chlorohydrin
process for the production of ethylene oxide was inefficient, because most of
the chlorine that was used was lost as calcium chloride. Since 1931, that
process has gradually been replaced by the direct vapour-phase oxidation
process, in which ethylene is oxidized to ethylene oxide with air or oxygen
and a silver catalyst at 10–30 atm (1–3 MPa) and 200–300 ºC.
production of ethylene oxide
1
 ETHYLENE OXIDE
production of ethylene oxide 2

 Application of ethylene oxide
Ethylene oxide is an important raw material used in the manufacture of chemical
derivatives that are the basis for major consumer goods in virtually all
industrialized countries. Figure 1 gives an overview of global industry demand for
ethylene oxide by application. More than half of the ethylene oxide produced
worldwide is used in the manufacture of monoethylene glycol Other derivatives of
ethylene oxide include: diethylene glycol, which is used in the production of
polyurethanes, polyesters, softeners (cork, glue, casein and paper), plasticizers and
solvents and in gas drying; triethylene glycol, which is used in the manufacture of
lacquers, solvents, plasticizers and humectants (moisture-retaining agents) and in
gas drying; poly(ethylene) glycols, which are reacted with other materials and used
in cosmetics, ointments, pharmaceutical preparations, lubricants (finishing of
textiles, ceramics), solvents (paints and drugs) and plasticizers (adhesives and
printing inks)
4
Manufacture of ethylene oxide
 Ethylene oxide has been produced commercially by two basic
routes: the ethylene chlorohydrin and direct oxidation
processes. The chlorohydrin process was first introduced
during World War I in Germany. The process involves the
reaction of ethylene with hypochlorous acid followed by
dehydrochlorination of the resulting chlorohydrin with lime to
produce ethylene oxide and calcium chloride. The chlorohydrin
process is not economically competitive and was quickly
replaced by the direct oxidation process as the dominant
technology. At the present time, all the ethylene oxide
production in the world is achieved by the direct oxidation
process. production of ethylene oxide
5
 The direct oxidation technology, as the name implies, utilizes
the catalytic oxidation of ethylene with oxygen over a silver-
based catalyst to yield ethylene oxide. The process can be
divided into two categories depending on the source of the
oxidizing agent: the air-based process and the oxygen-based
process. In the first, air or air enriched with oxygen is fed
directly to the system. In the second, a high purity oxygen
stream(>95 mol %) from an air separation unit is employed as
the source of the oxidizing agent.

Chlorohydrin process of production of ethylene oxide
 Although the chlorohydrin process is almost entirely
superseded in the industry by the direct oxidation of ethylene,
the knowledge of this method is still important for educational
reasons and because it is still used in the production of
propylene oxide.The process consists of three major steps:
synthesis of ethylene chlorohydrin, dehydrochlorination of
ethylene chlorohydrin to ethylene oxide and purification of
ethylene oxide. Those steps are carried continuously. In the
first column, hypochlorination of ethylene is carried out as
shown in the next slide.

 Cl2 + H2O → HOCl + HCl
 CH2=CH2 + HOCl → HO–CH2CH2–Cl
 CH2=CH2 + Cl2 → Cl–CH2CH2–Cl
To suppress the conversion of ethylene into the ethylene dichloride (the last reaction), the
concentration of ethylene is maintained at about 4–6%, and the solution is heated by steam to
the boiling point.Next, aqueous solution of ethylene chlorohydrin enters the second column,
where it reacts with a 30% solution of calcium hydroxide at 100 °C (212 °F).
 2 OH–CH2CH2–Cl + Ca(OH)2 → 2 (CH2CH2)O + CaCl2 + 2H2O
The produced ethylene oxide is purified by rectification. The chlorohydrin process allows to
reach 95% conversion of ethylene chlorohydrin. The yield of ethylene oxide is about 80% of
the theoretical value; for 1 tonne (0.98 long tons; 1.1 short tons) of ethylene oxide, about 200
kg (440 lb) of ethylene dichloride is produced. But, the major drawbacks of this process are
high chlorine consumption and effluent load. This process is now obsolete.

Direct Oxidation Processes
 Compared to the chlorohydrin process, direct oxidation eliminates the need
for large volumes of chlorine. Also, there are no chlorinated hydrocarbon by-
products to be sold, processing facilities can be made simpler, and operating
costs are lower. The main disadvantage of the direct oxidation process is the
lower yield or selectivity of ethylene oxide per unit of feed ethylene
consumed. The main inefficiency in the process results from the loss of 20-
25% of the ethylene to carbon dioxide and water. Consequently, operating
conditions must be carefully controlled to maximize selectivity. It is
characterized by high selectivity with respect to the ethylene oxide product
and long lifetime of the catalyst (3 years).Older factories typically use air for
oxidation whereas newer plants and processes, such as METEOR and Japan
Catalytic, favor oxygen.
 Chemical Equation

10
• Ethylene to air ratio: 3 – 10 %
• Side reaction products: CO2, H2O
• Catalyst: – Silver oxide on alumina
• Operating temperature and pressure: 250 – 300 oC and
120 – 300 psi
• Supressing agent for side reactions: – Ethylene
dichloride
• Reaction is exothermic.

 Direct oxidation process of ethylene oxide

REFERENCE
 Kirk-Othmer Encyclopedia of Chemical Technology (4th
Edition)
 https://en.wikipedia.org/wiki/Ethylene_oxide
 https://pubs.acs.org/doi/pdf/10.1021/ie50492a013
 Industrial Organic Chemistry, Third Completely Revised
Edition

15

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COLLEGE OF SCIENCE

3, REDIET BOGALE 1202751

4, EPHEREM ADDISE 1201563

production of ethylene oxide 2

production of ethylene oxide 6

production of ethylene oxide 7

production of ethylene oxide 8

production of ethylene oxide

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