The OMEGA process ("Only MEG Advantage")
is a chemical process discovered by the
Shell Global Solutions
Shell plc is a British multinational oil and gas company headquartered in London, England. Shell is a public limited company with a primary listing on the London Stock Exchange (LSE) and secondary listings on Euronext Amsterdam and the New Yo ...
company that is used to produce
ethylene glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...
from
ethylene. This process comprises two steps, the controlled oxidation of ethylene to
ethylene oxide
Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sw ...
, and the net hydrolysis of ethylene oxide to
monoethylene glycol (MEG).
The first chemical plant using the OMEGA process was started in South Korea. Subsequent OMEGA plants have been started in Saudi Arabia and Singapore.
Shell claims that this process, compared to conventional ones, does not produce higher glycols, uses less steam and water, and generates less waste.
[
]
Ethylene oxidation
To produce ethylene oxide, ethylene is oxidized with dioxygen in the presence of a silver catalyst. Some ethylene is over-oxidized to carbon dioxide and water, which is wasteful; early processes only gave ~ 65% selectivity for ethylene oxide as a result. In the OMEGA process, over-oxidation is reduced by including ethyl chloride
Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet ...
as a moderator.[
]
Ethylene oxide hydrolysis
Conventionally, monoethylene glycol (HOC2H4OH) is produced by the controlled hydrolysis of ethylene oxide (C2H4O). The monoethylene glycol product is also able to react with ethylene oxide to give diethylene glycol
Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, and hygroscopic liquid with a sweetish taste. It is a four carbon dimer of ethylene glycol. It is miscible in water, alcohol, ...
, and so on; sequential reaction with ethylene oxide is how poly(ethylene glycol)
Polyethylene glycol (PEG; ) is a polyether compound derived from petroleum with many applications, from industrial manufacturing to medicine. PEG is also known as polyethylene oxide (PEO) or polyoxyethylene (POE), depending on its molecular we ...
is produced. Due to monoethylene glycol's high boiling point, purification by distillation is energy intensive.
: C2H4O + H2O → HOC2H4OH
In the OMEGA process, the ethylene oxide reacts with carbon dioxide
Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is trans ...
(CO2) to yield ethylene carbonate
Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the cyclic carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a tran ...
(C3H4O3). Ethylene carbonate is subsequently hydrolyzed to monoethylene glycol and carbon dioxide. The carbon dioxide is released in this step again and can be fed back into the process circuit. This process is 99.5% selective for monoethylene glycol.[
: C2H4O + CO2 → C3H4O3
: C3H4O3 + H2O → HOC2H4OH + CO2
This part of the OMEGA process was originally developed by Mitsubishi Chemicals, and it has been exclusively licensed to Shell.][
]
See also
* Carbonate ester
In organic chemistry, a carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is and they ...
References
{{Reflist
Chemical processes
Carbonate esters
Diols