Introduction to the Product and Market Introduction We will be investigating the production of Ethylene Glycol and then go on to design

a plant that will produce 50,000 t/y of Ethylene Glycol in Canada. Firstly we need to consider what the compound consists of and how it can be manufactured from feedstock and also look into some properties and uses of the compound.

Fig 1: Ethylene Glycol

This is the hydroxyl part of the molecule. The hydroxyl part of the molecule allows this compound to form hydrogen bonds this allows the compound to be soluble in water swell as other organic solvents as it can form hydrogen bonds with them. It also has a relatively high boiling point compared to other organic compounds.

Properties Molecular formula Molar mass Density Melting point Boiling point Freezing Point Solubility C2H6O2 62.07 g mol1 1.1132 g/cm 12.9 C, 260 K, 9 F 197.3 C, 470 K, 387 F -13c Soluble in water and other organic solvents

What is Ethylene Glycol and its history? Ethylene glycol was first discovered by the French scientist Charles-Adolphe Wurts through the saponification reaction with potassium hydroxide in 1860, this was merely a lab-based experiment and at the time there was no uses for this compound so no industrial manufacture was taken. In 1860 the same scientist synthesized the compound through the hydrolysis of ethylene oxide and after the world war German had began to manufacture this compound as an alternative to glycerol in the explosive industry. Since then the manufacture of

ethylene glycol has increased and is still on an increase with around a 5% increase of the production of ethylene glycol every year. Shell now have rights to the current improved method.[3] Ethylene glycol is a colourless and odourless liquid with a syrupy consistency, it also has low volatility as well as low viscosity.[2] It is considered to be slightly flammable, it can react vigorously with oxidising agents and when heated to decomposition it emits acidic smoke and irritating fumes that are hazardous. Ethylene glycol acts as a good solvent and properties such as a very low freezing point, which can be beneficial in order to manufacture items such as anti-freeze and engine coolant. Antifreeze in cars generally has around a 50% content of ethylene glycol and windscreen wash around 14% of ethylene glycol content.[2] The structure in Fig 1 shows the structure of ethylene glycol also known as ethane 1,2 - diol. It contains two hydroxyl groups and a molecular formula of C2H6O2.The chemistry behind the two-hydroxyl groups allows it to act as an intermediate for a range of reaction. It can react to form aldehydes, carboxylic acids, amines, ethers, nitrile and many more organic compounds. This molecule is manufactured in industry in a number of ways but the most famous process with the best selectivity around 99% is the OMEGA Process which is carried out by Shell PLC which opened up its first plant in May 2008, now there are around 5 plants around the globe owned by shell which produce this chemical.[1] Health and Environmental issues of Ethylene Glycol Your health is not likely to be affected if small amounts of ethylene glycol if in taken. It has more effect on health if larger amounts are ingested, it can cause serious illness or even death. If he ethylene glycol enters the body it forms chemicals that crystallize and these crystals can be deposited in the kidneys that can affect the kidneys function. The ethylene glycol also forms acidic chemicals that affect the pH of the body and this can have major effect on lungs, nervous system and heart. This chemical as announced by the DHHS states that it has not been classified as a carcinogen.[4] People can be exposed to the ethylene glycol through skin contact with antifreeze and other products that contain the chemical or possibly through accidental or intentional indigestion of this chemical as it is sweet tasting and brightly coloured so can be attractive. People who work industrially with ethylene glycol are more likely to be affected as they are touching and are regularly exposed to the chemical.[4] Precautions must be taken in order to reduce the risk of exposure and indigestion. One may reduce the risk if the products that contain this chemical such as antifreeze is kept out of reach and are not easily accessible. One should reduce contact of this chemical with skin when using ethylene glycol products and avoid spilling or draining the antifreeze or similar products that contain this chemical. If you are exposed to large amounts of this chemical or have ingested

large amounts of this chemical you should seek medical attention immediately.[4] As well as exposure to humans and living species the ethylene glycol can also effect the environment. The primary source of ethylene glycol in the environment is from run-off at airports where de-icers are used on aeroplane runways. It can enter the environment through product that contains this chemical such as anti-freeze and de-icers that contain a large volume of this chemical. Although this chemical is exposed to the environment it can break down in the air within 10days and can break down in water and soil within few weeks.[4] Production of ethylene glycol Ethylene glycol can be synthesized in many chemical reactions as shown below but the most common method used in industry industry is the famous OMEGA process where the ethylene oxide is converted to the ethylene carbonate before it is hydrolysed into the ethylene glycol. This process is very effective as it has a selectivity of around 99% which is higher than the other proposed methods. This process is a mere improvement of the hydrolysis reaction where ethylene glycol is manufactured by the hydration of ethylene oxide in the presence of a silver catalyst in acidic conditions. Industrial production of ethylene oxide is substantial with over 18 million tonnes being produced worldwide in 2011. There are a number of methods used in order to produce the ethylene glycol some, which are lab, based experiments and some that have been taken onto industrial manufacturing. These are a few methods that can be used in order to produce the ethylene glycol: 1. Hydrolysis of Ethylene Oxide 2. Ethylene Carbonate Process (OMEGA process) 3. Teijn Oxychloronation process 4. Halcon Acetoxylation process 5. Conversion of Biomass 6. Trans-esterification of Ethylene Carbonate and Methanol 7. Carboxylation of Formaldehyde 8. 2-Chloroethan-1-ol + Sodium Carbonate 9. Ethylene + Hydrogen Peroxide 10. Carbonylation of n-butanol and Hydrogenation of n-butyloxide We will discuss all the possible routes and compare them in detail in the later part of the project.

Uses of Ethylene Glycol The reactivity and solubility of ethylene glycol provide the basis for many applications. The widespread use of ethylene glycol as an antifreeze is based on its ability to lower the freezing point when mixed with water. The end uses for ethylene glycol are numerous we will discuss the different uses and also summarise the uses as shown below in FIG 2.[2] Use of Ethylene Glycol as: Chemical Intermediate for Resins In the plastic industry the ethylene glycol is an important chemical, it is used in the manufacture of polyester fibres and resins such as Polyethylene terephthalate(PET). This PET which is made from the reaction of ethylene glycol with terephthalic acid is used to make common items such as plastic bottles. The production of these materials accounts for 40% of the total ethylene glycol consumption.[5] Solvent Coupler Ethylene glycol can also be used as a solvent coupler, it can be used as a stabilizer against gel formation, heat transfer fluid within a process chiller, air conditioning, ventilating and ice rinks. [5] Freezing point Depression This chemical is used to manufacture antifreeze, de-icing fluids in aircraft runways which accounts to 50% of the total use of this chemical. It is also used in water-based formulations such as adhesives, latex paints and asphalt emulsions.[6] Solvent It is used as a medium for suspending conductive salt in electrolytic capacitors.[6] Humectant The ethylene glycol can be used as a humectant to produce items such as textile fibres, paper, leather, adhesives and glue.[6] Non-Supported uses of Ethylene Glycol There are also uses of this chemical where it is restricted by regulation by this chemical could also be used in the production of tobacco, generation of artificial smoke or mist, in fire extinguishing sprinkler systems an in the manufacture of munitions.[6]

Properities and Characteristics Chemical Intermediate for Resins

Application and Uses Polyester resins (fibers, containers and films) Resin esters as plasticizers (adhesives, lacquers and enamels) Alkyd-type resins (synthetic rubbers, adhesives,surface coatings)

Solvent Coupler Freezing Point Depression

Stabilizer against gel formation Deicing fluids (aircraft, runway) Heat transfer fluids (gas compressors, heating,ventilating, air conditioning, process chillers,ice rinks) All-weather automotive antifreeze and coolants Water-based formulations (adhesives, latex paints,asphalt emulsions) Medium for suspending conductive salt in electrolytic capacitors Textile fibers Paper Leather Adhesives Glue Solvents
FIG 2 : Shows the overview of uses of Ethylene Glycol

Solvent Humectant

Chemical Intermediate

This Pie Chart shows the Major Uses of Ethylene Glycol

Poly Ester Fibre PET Resin Antifreeze Other

References Used
1 - http://wwwstatic.shell.com/static/chemicals/downloads/innovation/omega_van_kleeck.pdf 2 - http://www.meglobal.biz/media/product_guides/MEGlobal_MEG.pdf 3- http://en.wikipedia.org/wiki/Ethylene_glycol 4- www.atsdr.cdc.gov/tfacts96.pdf 5- www.thechemco.com/chemical/ethylene-glycol/ 6- www.meglobal.biz/media/MEGlobal_fastfacts_MEG.pdf