Ethylene oxide structure, properties, risks and uses

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Jonah Lester

The ethylene oxide It is an organic compound of the epoxide family. At room temperature it is gaseous, colorless and, although it is almost odorless, it has a mild sweet odor, similar to that of ethers..

It is a very versatile chemical building block, since it is used in a wide variety of industrial applications for the manufacture of other chemical compounds with multiple uses. This is due to its high reactivity, that is, its ease of reacting with other substances..

Ethylene oxide spatial structure. Black balls: carbon atoms; white balls: hydrogen atoms; red ball: oxygen atom. Benjah-bmm27 [Public domain]. Source: Wikimedia Commons.

One of its main applications is as a raw material in the manufacture of antifreeze components for vehicle radiators. Its derivatives are used as ingredients in industrial or household cleaners, cosmetic products and shampoos, plasticizers, pharmaceutical preparations or ointments..

It is a widely used disinfectant, for example, in the sterilization of medical and dental equipment, as it is capable of destroying viruses, bacteria, fungi and spores, especially in dry conditions. In addition, it has been used to fumigate food products for packaging, although this use is questioned.

Despite its usefulness, it must be handled with extreme caution, as it can cause eye and skin irritation. Inhaling ethylene oxide for long periods can affect the nervous system. Therefore, people who are exposed to its vapors or solutions should use protective equipment and clothing..

Article index

  • 1 Structure
  • 2 Properties
    • 2.1 Other names
    • 2.2 Physical state
    • 2.3 Molecular weight
    • 2.4 Flash point
    • 2.5 Density
    • 2.6 Solubility
    • 2.7 Autoignition temperature
    • 2.8 Other properties
  • 3 Production
  • 4 Risks
    • 4.1 For health
    • 4.2 Fire
  • 5 Uses
    • 5.1 Industrial applications
    • 5.2 Medical applications
    • 5.3 Libraries and museums
    • 5.4 Agriculture and food
  • 6 References

Structure

Its molecular formula is CtwoH4O. It belongs to the group of epoxies, being the simplest and most important of these. It is shaped like a three-membered ring.

Structure of ethylene oxide. Source: Wikimedia Commons

Due to its triangular ring structure, ethylene oxide is very reactive, which is due to the ease with which the ring opens. On average, the bond angles are 60º, which makes your bonds weak. The molecule is less stable than that of a linear ether and tends to react easily with other chemical compounds..

Properties

Other names

- Oxirano.

- Epoxyethane.

Physical state

At room temperature and under atmospheric pressure, it is a gas. Below 10.6 ºC and under atmospheric pressure, it is a liquid. Below -111 ºC it is a solid.

Molecular weight

44.05 g / mol.

Flashpoint

Less than 0ºF (-17.8ºC).

Density

Its density is lower than that of water, being 0.882 at 10 ºC. In turn, its vapors are heavier than air.

Solubility

It is soluble in water, benzene, acetone, ethanol, and ether. It is miscible with carbon tetrachloride.

Autoignition temperature

428.9 ºC.

Other properties

- If subjected to heating or contamination, it can polymerize exothermically (producing large amounts of heat). If polymerization occurs inside a container, it can rupture violently.

- May react with oxidizing materials.

- It is extremely toxic, carcinogenic and a good generator of mutations in bacteria and mammalian cells..

Production

On an industrial scale it is prepared by oxidizing ethylene with oxygen (Otwo) from air. The speed of this reaction increases with the presence of silver metal (Ag) and the action of temperature. The reaction is shown below:

Ag, 250ºC

2 CtwoH4 +  ORtwo  -> 2CtwoH4OR

Ethylene Ethylene oxide

Risks

To health

- It has been reported to cause neurological disorders and can cause death. The lowest concentration that can generate toxic effects by inhalation is 12,500 ppm / 10 seconds (ppm means: parts per million).

- It is a strong irritant to the skin, eyes and respiratory tract..

- Exposure to high concentration ethylene oxide vapors can cause eye irritation, inflammation of the eye membrane, and corneal damage..

- The development of cataracts has been associated with exposure to its vapors and splashes. Concentrated solutions cause severe damage to the eyes.

- Contact of aqueous solutions of ethylene oxide with the skin causes irritation and can lead to severe dermatitis with blisters and burns..

- Inhalation can affect the nervous system, causing headaches and nausea, among other symptoms..

Fire

- When exposed to a flame or heat there is a danger of explosion. When heated, dangerous fumes are generated.

- Vapor forms explosive mixtures with air in a wide range of concentrations.

- Avoid handling it with equipment that contains metals such as copper, silver, mercury, magnesium, aluminum or iron oxides, as well as avoiding agents such as ammonia, oxidizing agents, organic acids or bases, among others. All these materials can accelerate their polymerization and / or explosion.

Applications

Industrial applications

It is used as an intermediary in the production of other chemicals, which in turn are used in the manufacture of polyester fibers for clothing, upholstery, carpets and pillows..

Ethylene oxide produces the ethylene glycol used in vehicle engine antifreeze. Ethylene glycol is also used in the manufacture of fiberglass and plastic packaging films..

Other chemicals produced from ethylene oxide include non-ionic surfactants used in detergents and dishwashing formulas..

Medical applications

It is used as a sterilizing agent for medical equipment, such as surgical instruments, needles and hypodermic injectors or prostheses.

It is also used to sterilize hemodialysis machines, laboratory equipment, dental instruments, veterinary instruments, thermometers, surgical clothing or first aid equipment, among others..

Sterilization room. Source: pixabay.com

Although there are several methods available for the sterilization of medical equipment, in some uses no available treatment can replace ethylene oxide..

This is the case of the sterilization of certain materials sensitive to heat and radiation, as well as some instruments and devices that require sterilization at the site of use in hospitals..

Libraries and museums

In these places, ethylene oxide is used to control pests such as fungi and insects. However, this use is not so common and is used when other alternatives are not effective..

Agriculture and food

It has been used as a pesticide, fungicide, fumigant, herbicide, insecticide, rodenticide, among other variants. Significantly reduces the population of bacteria and fungi in spices.

However, due to safety and environmental concerns, the use of ethylene oxide for food fumigation has been banned in the European Union and the United States..

References

  1. U.S. National Library of Medicine. (2019). Ethylene Oxide. Recovered from pubchem.ncbi.nlm.nih.gov
  2. Chemical Safety Facts. (2019). Ethylene Oxide. Recovered from chemicalsafetyfacts.org
  3. Morrison, Robert Thornton; and Boyd, Robert Neilson. 1992. Organic Chemistry. Prentice-Hall.
  4. Moerman, F. and Mager, K. (2016). Cleaning and Disinfection in Dry Food Processing Facilities. In Handbook of Hygiene Control in the Food Industry (Second Edition). Recovered from sciendirect.com.
  5. Eastmond, David A. and Balakrishnan, Sharada. (2010). Genotoxicity of Pesticides. In Hayes' Handbook of Pesticide Toxicology (Third edition). Recovered from sciencedirect.com
  6. Atungulu, G.G. and Pan, Z. (2012). Microbial decontamination of nuts and spices. In Microbial Decontamination in the Food Industry. Recovered from sciencedirect.com

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