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Ethylene glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula (CH2OH)2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste but is toxic in high concentrations. This molecule has been observed in outer space.
Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation
This reaction can be catalyzed by either acids or bases or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. The separation of these oligomers and water is energy-intensive. World production of ethylene glycol was ~20 Mt in 2010.
A higher selectivity is achieved by the use of Shell's OMEGA process. In the OMEGA process, the ethylene oxide is first converted with carbon dioxide (CO2) to ethylene carbonate. This ring is then hydrolyzed with a base catalyst in a second step to produce mono-ethylene glycol in 98% selectivity. The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from ethylene oxide production, where a part of the ethylene is completely oxidized.
Ethylene glycol is produced from carbon monoxide in countries with large coal reserves and less stringent environmental regulations. The oxidative carbonylation of methanol to dimethyl oxalate provides a promising approach to the production of C
1-based ethylene glycol. Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%) by hydrogenation with a copper catalyst:
Because the methanol is recycled, only carbon monoxide, hydrogen, and oxygen are consumed. One plant with a production capacity of 200000 tons of ethylene glycol per year is in Inner Mongolia, and a second plant in the Chinese province of Henan with a capacity of 250000 tons per year was scheduled for 2012. As of 2015[update], four plants in China with a capacity of 200000 t/a each were operating, with at least 17 more to follow.
Ethylene glycol can be produced by recycling its polymeric derivatives, such as polyethylene terephthalate.
According to most sources, French chemist Charles-Adolphe Wurtz (1817–1884) first prepared ethylene glycol in 1856. He first treated "ethylene iodide" (1,2-Diiodoethane) with silver acetate and then hydrolyzed the resultant "ethylene diacetate" with potassium hydroxide. Wurtz named his new compound "glycol" because it shared qualities with both ethyl alcohol (with one hydroxyl group) and glycerin (with three hydroxyl groups). In 1859, Wurtz prepared ethylene glycol via the hydration of ethylene oxide. There appears to have been no commercial manufacture or application of ethylene glycol before World War I when it was synthesized from ethylene dichloride in Germany and used as a substitute for glycerol in the explosives industry.
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Ethylene glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula (CH2OH)2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste but is toxic in high concentrations. This molecule has been observed in outer space.
Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation
This reaction can be catalyzed by either acids or bases or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. The separation of these oligomers and water is energy-intensive. World production of ethylene glycol was ~20 Mt in 2010.
A higher selectivity is achieved by the use of Shell's OMEGA process. In the OMEGA process, the ethylene oxide is first converted with carbon dioxide (CO2) to ethylene carbonate. This ring is then hydrolyzed with a base catalyst in a second step to produce mono-ethylene glycol in 98% selectivity. The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from ethylene oxide production, where a part of the ethylene is completely oxidized.
Ethylene glycol is produced from carbon monoxide in countries with large coal reserves and less stringent environmental regulations. The oxidative carbonylation of methanol to dimethyl oxalate provides a promising approach to the production of C
1-based ethylene glycol. Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%) by hydrogenation with a copper catalyst:
Because the methanol is recycled, only carbon monoxide, hydrogen, and oxygen are consumed. One plant with a production capacity of 200000 tons of ethylene glycol per year is in Inner Mongolia, and a second plant in the Chinese province of Henan with a capacity of 250000 tons per year was scheduled for 2012. As of 2015[update], four plants in China with a capacity of 200000 t/a each were operating, with at least 17 more to follow.
Ethylene glycol can be produced by recycling its polymeric derivatives, such as polyethylene terephthalate.
According to most sources, French chemist Charles-Adolphe Wurtz (1817–1884) first prepared ethylene glycol in 1856. He first treated "ethylene iodide" (1,2-Diiodoethane) with silver acetate and then hydrolyzed the resultant "ethylene diacetate" with potassium hydroxide. Wurtz named his new compound "glycol" because it shared qualities with both ethyl alcohol (with one hydroxyl group) and glycerin (with three hydroxyl groups). In 1859, Wurtz prepared ethylene glycol via the hydration of ethylene oxide. There appears to have been no commercial manufacture or application of ethylene glycol before World War I when it was synthesized from ethylene dichloride in Germany and used as a substitute for glycerol in the explosives industry.