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Ethylene glycol
From Wikipedia, the free encyclopedia Ethylene glycol
E
Ethylene glycol disrupts hydrogen bonding when dissolved in water. Pure ethylene glycol freezes at about -12 °C, but when intermixed with water molecules, neither can readily form a solid crystal structure, and therefore the freezing point of the mixture is depressed significantly. The minimum freezing point is observed when the ethylene glycol percent in water is about 70%, as shown below. This is the reason pure ethylene glycol is not used as an antifreeze--water is a necessary component as well.
Ethylene glycol freezing point vs. concentration in waterWeight Percent EG (%) Freezing Point (deg F) Freezing Point (deg C)
0 32 0
10 25 -4
20 20 -7
30 5 -15
40 -10 -23
50 -30 -34
60 -55 -48
70 -60 -51
80 -50 -45
90 -20 -29
100 10 -12
However, the boiling point for aqueous ethylene glycol increases monotonically with increasing ethylene glycol percentage. Thus, the use of ethylene glycol not only depresses the freezing point but also elevates the boiling point such that the operating range for the heat transfer fluid is broadened on both ends of the temperature scale. The increase in boiling temperature is due to pure ethylene glycol having a much higher boiling point and lower vapour pressure than pure water; there is no chemical stabilisation against boiling of the liquid phase at intermediate compositions, as there is against freezing.
Ethylene glycol boiling point vs. concentration in waterWeight Percent EG (%) Boiling Point (deg F) Boiling Point (deg C)
0 212 100
10 215 102
20 215 102
30 220 104
40 220 104
50 225 107
60 230 110
70 240 116
80 255 124
90 285 140
100 387 197
In the plastics industry, ethylene glycol is important precursor to polyester fibers and resins. Polyethylene terephthalate, used to make plastic bottles for soft drinks, is prepared from ethylene glycol.
[edit]
Hydrate inhibition
Because of its high boiling point and affinity for water, ethylene glycol is a useful desiccant. Ethylene glycol is widely used to inhibit the formation of natural gas clathrates (hydrates) in long multiphase pipelines that convey natural gas from remote gas fields to an onshore processing facility. Ethylene glycol can be recovered from the natural gas and reused as an inhibitor after purification treatment that removes water and inorganic salts.
Natural gas is dehydrated by ethylene glycol. In this application, ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and hydrocarbon gases. Dry gas exits from the top of the tower. The glycol and water are separated, and the glycol recycled. Instead of removing water, ethylene glycol can also be used to depress the temperature at which hydrates are formed. The purity of glycol used for hydrate suppression (mono-ethylene glycol) is typically around 80%, whereas the purity of glycol used for dehydration (tri-ethylene glycol) is typically 95-99+%. Moreover, the injection rate for hydrate suppression is much lower than the circulation rate in a glycol dehydration tower.
[edit]
Niche applications
Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of 1,4-dioxane and as an additive to prevent corrosion in liquid cooling systems for personal computers. Ethylene glycol is also used in the manufacture of some vaccines, but it is not itself present in these injections. It is used as a minor (1–2%) ingredient in shoe polish and also in some inks and dyes. Ethylene glycol has seen some use as a rot and fungal treatment for wood, both as a preventative and a treatment after the fact. It has been used in a few cases to treat partially rotted wooden objects to be displayed in museums. It is one of only a few treatments that are successful in dealing with rot in wooden boats, and is relatively cheap. Ethylene glycol may also be one of the minor ingredients in screen cleaning solutions, along with the main ingredient isopropyl alcohol. Ethylene glycol is commonly used as a preservative for biological specimens, especially in secondary schools during dissection as a safer alternative to formaldehyde. It can also be used in killing jars.
[edit]
Chemical reactions
Ethylene glycol is used as a protecting group for carbonyl groups in organic synthesis. Treating a ketone or aldehyde with ethylene glycol in the presence of an acid catalyst (e.g., p-toluenesulfonic acid; BF3•Et2O) gives the corresponding a 1,3-dioxolane, which is resistant to bases and other nucleophiles. The 1,3-dioxolane protecting group can thereafter be removed by further acid hydrolysis.[4] In this example, isophorone was protected using ethylene glycol with p-toluenesulfonic acid in moderate yield. Water was removed by azeotropic distillation to shift the equilibrium to the right.[5]
[edit]
Toxicity
Main article: ethylene glycol poisoning
Ethylene glycol is moderately toxic with an oral LDLO = 786 mg/kg for humans.[6] The major danger is due to its sweet taste. Because of that, children and animals are more inclined to consume large quantities of it than they are other poisons. Upon ingestion, ethylene glycol is oxidized to glycolic acid which is, in turn, oxidized to oxalic acid, which is toxic. It and its toxic byproducts first affect the central nervous system, then the heart, and finally the kidneys. Ingestion of sufficient amounts can be fatal if untreated.[7]
From Wikipedia, the free encyclopedia Ethylene glycol
E
Ethylene glycol disrupts hydrogen bonding when dissolved in water. Pure ethylene glycol freezes at about -12 °C, but when intermixed with water molecules, neither can readily form a solid crystal structure, and therefore the freezing point of the mixture is depressed significantly. The minimum freezing point is observed when the ethylene glycol percent in water is about 70%, as shown below. This is the reason pure ethylene glycol is not used as an antifreeze--water is a necessary component as well.
Ethylene glycol freezing point vs. concentration in waterWeight Percent EG (%) Freezing Point (deg F) Freezing Point (deg C)
0 32 0
10 25 -4
20 20 -7
30 5 -15
40 -10 -23
50 -30 -34
60 -55 -48
70 -60 -51
80 -50 -45
90 -20 -29
100 10 -12
However, the boiling point for aqueous ethylene glycol increases monotonically with increasing ethylene glycol percentage. Thus, the use of ethylene glycol not only depresses the freezing point but also elevates the boiling point such that the operating range for the heat transfer fluid is broadened on both ends of the temperature scale. The increase in boiling temperature is due to pure ethylene glycol having a much higher boiling point and lower vapour pressure than pure water; there is no chemical stabilisation against boiling of the liquid phase at intermediate compositions, as there is against freezing.
Ethylene glycol boiling point vs. concentration in waterWeight Percent EG (%) Boiling Point (deg F) Boiling Point (deg C)
0 212 100
10 215 102
20 215 102
30 220 104
40 220 104
50 225 107
60 230 110
70 240 116
80 255 124
90 285 140
100 387 197
In the plastics industry, ethylene glycol is important precursor to polyester fibers and resins. Polyethylene terephthalate, used to make plastic bottles for soft drinks, is prepared from ethylene glycol.
[edit]
Hydrate inhibition
Because of its high boiling point and affinity for water, ethylene glycol is a useful desiccant. Ethylene glycol is widely used to inhibit the formation of natural gas clathrates (hydrates) in long multiphase pipelines that convey natural gas from remote gas fields to an onshore processing facility. Ethylene glycol can be recovered from the natural gas and reused as an inhibitor after purification treatment that removes water and inorganic salts.
Natural gas is dehydrated by ethylene glycol. In this application, ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and hydrocarbon gases. Dry gas exits from the top of the tower. The glycol and water are separated, and the glycol recycled. Instead of removing water, ethylene glycol can also be used to depress the temperature at which hydrates are formed. The purity of glycol used for hydrate suppression (mono-ethylene glycol) is typically around 80%, whereas the purity of glycol used for dehydration (tri-ethylene glycol) is typically 95-99+%. Moreover, the injection rate for hydrate suppression is much lower than the circulation rate in a glycol dehydration tower.
[edit]
Niche applications
Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of 1,4-dioxane and as an additive to prevent corrosion in liquid cooling systems for personal computers. Ethylene glycol is also used in the manufacture of some vaccines, but it is not itself present in these injections. It is used as a minor (1–2%) ingredient in shoe polish and also in some inks and dyes. Ethylene glycol has seen some use as a rot and fungal treatment for wood, both as a preventative and a treatment after the fact. It has been used in a few cases to treat partially rotted wooden objects to be displayed in museums. It is one of only a few treatments that are successful in dealing with rot in wooden boats, and is relatively cheap. Ethylene glycol may also be one of the minor ingredients in screen cleaning solutions, along with the main ingredient isopropyl alcohol. Ethylene glycol is commonly used as a preservative for biological specimens, especially in secondary schools during dissection as a safer alternative to formaldehyde. It can also be used in killing jars.
[edit]
Chemical reactions
Ethylene glycol is used as a protecting group for carbonyl groups in organic synthesis. Treating a ketone or aldehyde with ethylene glycol in the presence of an acid catalyst (e.g., p-toluenesulfonic acid; BF3•Et2O) gives the corresponding a 1,3-dioxolane, which is resistant to bases and other nucleophiles. The 1,3-dioxolane protecting group can thereafter be removed by further acid hydrolysis.[4] In this example, isophorone was protected using ethylene glycol with p-toluenesulfonic acid in moderate yield. Water was removed by azeotropic distillation to shift the equilibrium to the right.[5]
[edit]
Toxicity
Main article: ethylene glycol poisoning
Ethylene glycol is moderately toxic with an oral LDLO = 786 mg/kg for humans.[6] The major danger is due to its sweet taste. Because of that, children and animals are more inclined to consume large quantities of it than they are other poisons. Upon ingestion, ethylene glycol is oxidized to glycolic acid which is, in turn, oxidized to oxalic acid, which is toxic. It and its toxic byproducts first affect the central nervous system, then the heart, and finally the kidneys. Ingestion of sufficient amounts can be fatal if untreated.[7]
