Phenol



Phenol
IUPAC name Phenol
Other names Carbolic Acid
Benzenol
Phenylic Acid
Hydroxybenzene
Phenic acid
Identifiers
CAS number 108-95-2
RTECS number SJ3325000
SMILES Oc1ccccc1
InChI InChI=1/C6H6O/c7-6-
4-2-1-3-5-6/h1-5,7H
Properties
Molecular formula C6H5OH
Molar mass 94.11 g/mol
Appearance White Crystalline Solid
Density 1.07 g/cm³
Melting point

40.5 °C

Boiling point

181.7 °C

Solubility in water 8.3 g/100 ml (20 °C)
Acidity (pKa) 9.95
Dipole moment 1.7 D
Hazards
EU classification Toxic (T)
Muta. Cat. 3
Corrosive (C)
NFPA 704
2
4
0
 
Flash point 79 °C
Related Compounds
Related compounds Benzenethiol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Phenol, also known under an older name of carbolic acid, is a toxic, colourless aromatic compound.

Phenols

Main article: phenols

The word phenol is also used to refer to any compound that contains a six-membered organic compounds of which the phenol discussed in this article is the simplest member.

Properties

Phenol has a limited acetone, which is 10.9 in comparison to phenol with a pKa of 10.0.[3]

Production

Phenol can be made from the partial cumene process, or by the Raschig process. It can also be found as a product of coal oxidation.

Uses

Phenol has 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 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[citation needed]. One of the most famous inmates at Auschwitz to be executed 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) (RNA) from proteins.

Hydrothermal chemistry

Under laboratory conditions mimicking hydrothermal circulation (water, 200 °C, 1.9 GPa), phenol is found to form from tyrosine. However, as tyrosine is known to result directly from hydroxylation of phenylalanine in modern biological systems,[7] the implications of prebiotic phenol are questionable at best.

See also

References

  1. ^ Organic Chemistry 2nd Ed. John McMurry ISBN 0534079687
  2. ^ The Acidity of Phenol. ChemGuide. Jim Clark. Retrieved on 2007-08-05.
  3. ^ For further reading on the fine points of this topic, see David A. Evans's explanation.
  4. ^ Wealthy Eccentrics. CNN.com. Retrieved on 2007-02-23.
  5. ^ Killing through phenol injection. Auschwitz - FINAL STATION EXTERMINATION. Johannes Kepler University, Linz, Austria. Retrieved on 2006-09-29.
  6. ^ 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
  7. ^ http://web.indstate.edu/thcme/mwking/amino-acid-metabolism.html#tyrosine
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phenol". A list of authors is available in Wikipedia.