Phenol
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Overview
Phenol, also known under an older name of carbolic acid, is a toxic, colourless crystalline solid with a sweet tarry odor. Its chemical formula is C6H5OH and its structure is that of a hydroxyl group (-OH) bonded to a phenyl ring; it is thus an aromatic compound.
Phenols
The word phenol is also used to refer to any compound which contains a six-membered aromatic ring, bonded directly to a hydroxyl group (-OH). In effect, phenols are a class of organic compounds of which the phenol discussed in this article is the simplest member.
Properties
Phenol has a limited solubility in water (8.3 g/100 ml). It is slightly acidic: the phenol molecule has weak tendencies to lose the H+ ion from the hydroxyl group, resulting in the highly water-soluble phenoxide anion C6H5O−. Compared to aliphatic alcohols, phenol shows much higher acidity; it even reacts with aqueous NaOH to lose H+, whereas aliphatic alcohols do not. One explanation for the increased acidity is resonance stabilization of the phenoxide anion by the aromatic ring. In this way, the negative charge on oxygen is shared by the ortho and para carbon atoms[1]. In another explanation, increased acidity is the result of orbital overlap between the oxygen's lone pairs and the aromatic system[2]. In a third, the dominant effect is the induction from the sp² hybridized carbons; the comparatively more powerful inductive withdrawal of electron density that is provided by the sp² system compared to an sp³ system allows for great stabilization of the oxyanion. In making this conclusion, one can examine the pKa of the enol of acetone, which is 10.9 in comparison to phenol with a pKa of 10.0.[3]
Production
Phenol can be made from the partial oxidation of benzene or benzoic acid, by the cumene process, or by the Raschig process. It can also be found as a product of coal oxidation.
Uses
Phenol has antiseptic properties, and was used by Sir Joseph Lister (1827-1912) in his pioneering technique of antiseptic surgery, though the skin irritation caused by continual exposure to phenol eventually led to the substitution of aseptic (germ-free) techniques in surgery. (In fact, surgical gloves were first used to protect doctor's hands from phenol burns.) It is also the active ingredient in some oral anesthetics such as Chloraseptic spray. Phenol was also the main ingredient of the Carbolic Smoke Ball, a device sold in London designed to protect the user against influenza and other ailments. In the early part of the 20th century, it was used in the Battle Creek Sanitarium to discourage female masturbation.[4]
It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkiller, and synthetic resins (Bakelite, one of the first synthetic resins to be manufactured, is a polymer of phenol with formaldehyde). Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Washing with large amounts of plain water (most labs have a safety shower or eye-wash) and removal of contaminated clothing are required, and immediate ER treatment for large splashes; particularly if the phenol is mixed with chloroform (a commonly used mixture in molecular biology for DNA purification). Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin. It is also used in phenolization, a surgical procedure used to treat an ingrown nail, in which it is applied to the toe to prevent regrowth of nails.
Injections of phenol have occasionally been used as a means of rapid execution. In particular, phenol was used as a means of extermination by the Nazis during the Second World War. Phenol injections were given to thousands of people in concentration camps, especially at Auschwitz-Birkenau. Injections were administered either by medical doctors or by their assistants; such injections were originally given intravenously, more commonly in the arm, but injection directly into the heart, so as to induce nearly instant death, was later preferred. One of the most famous inmates at Auschwitz to be murdered by carbolic acid injection was St. Maximilian Kolbe, a Catholic priest who volunteered to undergo three weeks of starvation and dehydration in the place of another inmate and who was finally injected with carbolic acid so that the Nazis could make more room in their holding cells.[5]
A use of phenol in molecular biology is the separation of genetic material (nucleic acids) (DNA & RNA) from proteins.
Hydrothermal chemistry
Under laboratory conditions mimicking hydrothermal circulation (water, 200°C, 1.9 GPa), phenol is found to form from sodium hydrogen carbonate and iron powder (1.8% chemical yield)[6]. This discovery made in 2007 may be relevant to the origin of life question as phenol is a fragment of the biomolecule tyrosine.
See also
References
- ↑ Organic Chemistry 2nd Ed. John McMurry ISBN 0534079687
- ↑ "The Acidity of Phenol". ChemGuide. Jim Clark. Retrieved 2007-08-05.
- ↑ For further reading on the fine points of this topic, see David A. Evans's explanation.
- ↑ "Wealthy Eccentrics". CNN.com. Retrieved 2007-02-23.
- ↑ "Killing through phenol injection". Auschwitz - FINAL STATION EXTERMINATION. Johannes Kepler University, Linz, Austria. Retrieved 2006-09-29.
- ↑ Hydrothermal Reactions from Sodium Hydrogen Carbonate to Phenol Ge Tian, Hongming Yuan, Ying Mu, Chao He, and Shouhua Feng Org. Lett.; 2007; 9(10) pp 2019 - 2021; (Letter) DOI: 10.1021/ol070597o
External links
- International Chemical Safety Card 0070
- Phenol Material Safety Data Sheet
- National Pollutant Inventory - Phenol Fact Sheet
- NIOSH Pocket Guide to Chemical Hazards
- IARC Monograph: "Phenol"
- Arcane Radio Trivia outlines competing uses for Phenol circa 1915
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