ETHYLENE OXIDE

PRESENTED BY: GROUP #7

ANAS NOOR (CH-006)
UMAR SIDDIQUI (CH-016)
SYED ALI RAZA SANI (CH-019)
MUHAMMAD ZUBAIR KHAN (CH-023)

ETHYLENE OXIDE
INTRODUCTION:
- Ethylene Oxide (EO), sometimes referred to as Oxirane, is the simplest cyclic ether. It is
a colorless gas or liquid and has a sweet, etheric odor.
- The C-C bond is short and the bond angles strained . Because its highly strained ring
can be opened easily, EO is highly reactive.
- EO was first prepared in 1859 by Wurtz using potassium hydroxide solution to eliminate
hydrochloric acid from ethylene chlorohydrin. The chlorohydrin process developed from
Wurtz's discovery and industrial production of EO began in 1914. The direct catalytic
oxidation of ethylene, discovered in 1931 by Lefort, has gradually superseded the
chlorohydrin process. Currently, EO is produced by direct oxidation of ethylene with air or
oxygen.
- Methods to produce commercially:

ETHYLENE CHLOROHYDRIN METHOD

DIRECT OXIDATION PROCESS

- The highly reactive nature of EO, which helps make it a versatile and commercially

important chemical intermediate, also underlies some of the main hazards of EO in

particular, its flammability, reactivity, explosive vapor decomposability and toxicity.
Understanding the properties of EO is important to managing its use.

NOMENCLATURE OF ETHYLENE OXIDE:

- Chemical Abstracts Name: Oxirane

Chemical Abstracts Number: 75-21-8

PSUID Code: 1441
UN CODE: 1040
IUPAC Name: Oxirane

- Synonyms: Ethylene Oxide; 1,2-Epoxyethane;Dihydrooxirene; Oxacyclopropane;

Dimethylene Oxide; Oxidoethane; Epoxyethane; EO; ETO.
- Other Names: Ethene oxide; Oxane; Oxirene, Dihydro-; Oxyfume; Oxyfume 12; TGas; Aethylenoxid; Amprolene; Anprolene; Anproline; ENT-26263; E.O.; 1,2Epoxyaethan; Ethox; Ethyleenoxide; Etylenu tlenek; FEMA No. 2433; Merpol; NCIC50088; ,- Oxidoethane; Oxiraan; Oxiran; RCRA waste number U115; Sterilizing
gas ethylene oxide 100%; C2H4O.
- Structural Formula: CH2OCH2

PHYSICAL PROPERTIES AND STRUCTURE:

- Molar mass: 44.05 g mol1

- Appearance: Colorless gas

- Density: 0.882 g/mL, 7.360 lbs/gallon
- Melting point: 111.3 C
- Boiling point: 10.7 C
- Solubility in water: Miscible
- Main hazards: Carcinogenic
- Flash point: -20C
- Explosive limits: 3 to 100%
- Std enthalpy of formation Hfo298=
52.6 kJ mol1
- Std molar entropy So298= 243 J mol1 K1

USES OF ETHYLENE OXIDE:

`

Products derived from EO have many different uses. Some of these products (or uses)
include:
Monoethylene Glycol: Antifreeze for engines, production of polyethylene terephthalate
(polyester fibers, film, and bottles), and heat transfer liquids and deicing of aircraft and
runways.
Diethylene Glycol: Polyurethanes, polyesters, softeners (cork, glue, casein and paper),
plasticizers, gas drying and solvents.
Triethylene Glycol: Polyurethanes, lacquers, solvents, plasticizers, gas drying and
humectants (moisture-retaining agents).
Poly(ethylene) Glycols: Cosmetics, ointments, pharmaceutical preparations, lubricants
(finishing of textiles and ceramics), solvents (paints and drugs) and plasticizers (adhesives
and printing inks).
Ethylene Glycol Ethers: Brake fluids, detergents, solvents (paints and lacquers), and
extractants for SO2, H2S, CO2 and mercaptans from natural gas and refinery gas.
Ethanolamines: Chemicals for textile finishing, cosmetics, soaps, detergents and
natural gas purification.
Ethoxylation products of fatty alcohols, fatty amines, alkyl phenols, cellulose,
poly(propylene glycol): Detergents and surfactants (nonionic), biodegradable
detergents, emulsifiers and dispersants. EO also has direct uses as a sterilizing agent for
medical devices and equipment and as a fumigant for spices. In sterilization applications, it
is sometimes referred to as EtO.

CHEMICAL PROPERTIES
Solubility of Ethylene Oxide Gas:
The solubility of EO gas in various compounds has been measured and reported at atmospheric pressure
and 72-74F (22-23C) by Chaigneau. These compounds include water, alcohols, hydrocarbons, oils,
chlorocompounds, esters and waxes.
Solubility of Gases in Ethylene Oxide:
The solubility of gases in liquid EO vary, increasing in the order nitrogen, argon, methane and ethane.
Increasing temperature tends to increase the solubility.
Combustion/Flammability:
EO is a flammable, explosive chemical. Its fire and explosion characteristics are system dependent. Some
of the characteristics for EO/air mixtures are as follows:
The minimum value cited for the lower flammable limit of EO air mixtures is 2.6%.
The upper flammable limit is typically stated to be 100% because pure EO can violently
decompose with a
significant release of heat in the absence of air or oxygen.
Accordingly, the flammable range of EO-air mixtures is 2.6-100%.
The auto-ignition temperature of EO in air at 14.7 psia is 833F (445C) . This temperature
can be lower with the presence of certain impurities such as water, acetaldehyde, and rust.
Flammability of Ethylene Oxide and Water Mixtures:
Due to the flash characteristics of EO/water mixtures, it can be difficult to extinguish fires of these liquid
mixtures until the EO reaches a certain dilution. In closed systems such as sewers, 100 to 1 water to EO
dilution ratios (vol/vol) may be required to produce a mixture, the vapor of which will not support
combustion. In open systems, such as around an atmospheric spill, water/EO mixtures of less than 22 to 1
(vol/vol) can generate sufficient vapors to support combustion.
Ignition Energy and Static Electricity:
Liquid EO is an electrically conductive fluid that cannot accumulate static electricity charges in metal
containers having internal parts properly bonded and grounded. Bottom filling is therefore generally not
needed unless there are isolated internal areas that might accumulate a charge. If containers have nonconductive linings, such as glass or plastic, use of an uncoated grounded metal device in contact with the
contained liquid at all times provides effective grounding of the liquid.

Decomposition:
Pure EO vapor or EO vapor mixed with air or an insufficient amount of inert gases can decompose
explosively. The primary decomposition reaction is expressed by the following equation:
EO (C2H4O) => CO + CH4 + 1312 BTU/lb
The reaction can also produce ethane, ethylene, hydrogen, carbon and acetaldehyde.
Deflagration and Detonation of Ethylene Oxide in Piping:
Unpublished work by Union Carbide performed in 1956 provided some information on the topic of EO
vapor decomposition flame propagation, suggesting that at pressures up to 75 psia, EO decomposition
flames would not be expected to propagate indefinitely through vented, horizontal pipe with a diameter of
less than 2 inches. In the late 1990s, the American Chemistry Councils Ethylene Oxide Industry Council
(now the Ethylene Oxide/Ethylene Glycols Panel), sponsored work to revisit earlier Union Carbide data and
to obtain specific information in two areas: (1) decomposition flame speeds and the extent of flame
propagation in long lengths of 2-inch diameter pipe containing pure EO vapor; and (2) maximum flame
speeds in long lengths of 12-inch pipe containing pure EO vapor.
Reaction with Water:
The reaction of EO with water (i.e., hydrolysis) to produce high molecular weight glycols is widely practiced
within chemical process industries. Hydrolysis of EO to higher molecular weight glycols is also used in the
design of EO vent scrubbers where EO absorbed by water is reacted to glycols. Reactions of this type are
exothermic and require appropriately sized heat removal equipment. Adding or mixing water to EO
inventories in storage vessels or transportation containers has potentially severe consequences.
Polymerization:
EO has a tendency to polymerize, formation of EO polymer is a function of temperature,
temperature and exposure to catalysts or contaminants.

time at

USAGE AND PRODUCTION IN GLOBAL MARKET:

International companies that produce EO :
BASF WYANDOTTE
CELANESE
DOW CHEMICAL COMPANY
TEXAS EASTMAN
SHELL
OLIN
ICI
SUNOLIN
RELIANCE INDUSTRIES LIMITED
International companies that consume EO:
DOW CHEMICAL COMPANY
STERIGENICS
SHELL INTERNATIONAL CHEMICALS BV
JAPAN CATALYTIC CHEMICAL Co.
CLARIANT
AKZO NOBEL
SASOL GERMANY
Supplier in Pakistan:

International Petrochemical Pvt. Ltd, Lahore

THE BLOCK FLOW DIAGRAM (BFD)

Proceeding from left to right, the process continues except
for recycling of the CO2 removal process while the rest of
the system proceeds in the forward (left) direction.

PROCESS DESCRIPTION:
Overview:
Ethylene oxide (EO) was initially manufactured using ethylene chlorohydrin as an intermediate, but this route has
been superseded by the direct oxidation of ethylene with air or oxygen. Now, nearly all the world's EO capacity is
based on direct oxidation, with oxygen generally preferred over the air route in larger plants due to higher yields
and less downtime.
Ethylene oxide is produced by a gas phase reaction of ethylene and oxygen over a fixed bed silver-based catalyst
in multi-tubular reactors. The reaction is exothermic and EO is recovered from the gas stream, purified and stored.
The ethylene oxide units are equipped with advanced process control, gas detection and emergency shutdown
systems.
Specifics:
Ethylene, compressed oxygen and recycle gas are mixed and fed to a multi-tubular catalytic reactor. The mixture
is passed over a silver oxide catalyst supported on a porous carrier at 200-300 oC and 10-30 bar. The reaction is
highly exothermic and the heat removed can be used to generate steam.
The gases from the reactor are first cooled and passed through a scrubber where the ethylene oxide is absorbed
as a dilute aqueous solution. The EO can then go straight to glycol manufacture or purified by fractionation for use
in other ethylene oxide derivatives.
The selective oxidation, or epoxidation, to produce ethylene oxide takes place between adsorbed ethylene and
adsorbed oxygen. Neglecting the form of adsorbed oxygen (molecular or atomic), the basic reaction stoichiometry
can be described as:

C2H4 + 1/2O2 -> C2H4O

Since ethylene oxide is such a reactive species, due to its highly strained 3-member ring structure, care must be
taken to stop the oxidation after the ethylene oxide is formed and not to further oxidize the product to carbon
dioxide and water. In fact, care must also be taken to prevent the total oxidation, or combustion, of ethylene to
carbon dioxide and water.

C2H4O + 2 1/2O2 -> 2CO2 + 2H2O

Thus, the overall reaction is:

C2H4 + 3O2 -> 2CO2 + 2H2O

RAW MATERIALS:
OXYGEN, ETHYLENE OR ETHYLENE RICH HYDROCARBON.

THE PROCESS FLOW DIAGRAM (PFD)

Scrubbing zone top temperature: 230F; Pressure: 310 Psig
Flashing zone top temperature; 225F; Pressure: 30 Psig
Main stripping zone temperature: 230F; Pressure: 2 Psig

HAZARDS AND PRECAUTIONS:

- How can ethylene oxide harm workers?
In addition to eye pain and sore throat, exposure to EtO can cause difficult breathing and blurred vision. Exposure
can also cause dizziness, nausea, headache, convulsions, blisters and can result in vomiting and coughing. Both
human and animal studies show that EtO is a carcinogen that may cause leukemia and other cancers. EtO is also
linked to spontaneous abortion, genetic damage, nerve damage, peripheral paralysis, muscle weakness, as well
as impaired thinking and memory. In liquid form, EtO can cause severe skin irritation upon prolonged or confined
contact.
- What should employers know about ethylene oxide?
Employee exposure is limited to one part EtO per million parts of air (1 ppm) measured as an 8-hour timeweighted average (TWA). Employee exposure may not exceed the short-term excursion limit of 5 ppm EtO
averaged over any 15-minute sampling period. These limits are called permissible exposure limits (PELs). Most
occupational exposures to EtO are covered by the OSHA standard. The standard does not apply, however, when
employers can demonstrate that the processing, use, or handling of products containing EtO will not release
airborne concentrations of EtO at or above the standards action level of 0.5 ppm. The action level is calculated as
an 8-hour TWA and is the threshold for increased compliance activities (e.g., air monitoring, medical
examinations, labeling, employee information, and training).
- What must employers do when exposures exceed the standards permissible

exposure limits?

If employee exposures exceed either the PEL or the excursion limit, employers must take the following actions:
Use engineering controls and work practices to control employee exposure.
Establish and implement a written compliance program to reduce exposures to or below the TWA and exposure
limit.
Establish personal air monitoring as well as information and training programs for employees exposed to EtO at
or above the action level or above the excursion limit. Conduct training upon initial job assignment and annually.
Establish a regulated area wherever airborne concentrations of EtO are expected to exceed the 8-hour TWA or
the excursion limit.

 Establish a medical surveillance program for employees exposed to EtO at concentrations above the action
level of 0.5 ppm, measured as an 8-hour TWA, for more than 30 days per year.
Place warning labels on all containers that might cause employee exposures at or above the action level or
excursion limit.
Remember that employee rotation is prohibited as a means of compliance with the 8-hour TWA or exposure
limit.
Select, provide, and maintain appropriate personal protective equipment and ensure that employees use it to
prevent skin and eye contact.
- What are employers required to do concerning exposure monitoring?
To help protect workers, employers must conduct the following exposure monitoring:
Initial monitoring to determine the airborne concentrations of EtO that workers are exposed to (representative
sampling of employees exposures is permitted).
Periodic exposure monitoring if the airborne concentration of EtO is at or above the action level or above the
15-minute excursion limit.
Additional monitoring if there has been a change in workplace conditions, such as a change in the process or
materials used, and if the change could increase employee exposures.
Allow affected employees or their designated representatives to observe the monitoring.
Notify affected employees of the results of the monitoring within 15 working days of receiving the results.
- What should employees do to protect themselves from EtO exposure?
To protect against EtO exposure, follow these safety precautions:
Wear goggles and skin protection at all times in areas where there is a risk of splashes from liquid EtO.
Wear proper protective clothing and other approved personal protective equipment when working with EtO.
Discard clothing that has been degraded by EtO.
See a doctor if you are exposed to EtO.
Do not eat, drink, or smoke while working with EtO.

SOME VERY BAD ACCIDENTS HAVE OCCURRED BECAUSE OF THIS APPARENTLY

ORDINARY CHEMICAL:

THANK YOU ALL FOR

YOUR PATIENCE.