1. MSA University,
Faculty of Pharmacy
Organic Chemistry
Department.
1- NAME OF THE ASSIGN : Discuss Phenols and their derivatives
as Antiseptics
2- Course Code, PC 112
NAME : MOHMAED ADEL AFIFI ABDO ID:142311
FOR DR : NADIA
Phenol is the original antiseptic, old name carbolic acid. This was used by Lister, who discovered
antiseptics. It works well but is rather toxic.
If you react phenol with chlorine, then you get a Trichlorophenol, called TCP. This is pretty non-
toxic and TCP is the most widely used phenol derivative used as an antiseptic today.
There are many other halogenated phenol derivatives in use and these include Chlorocresol
Chloroxylenol
Chlorophene
Hexachlorophane/hexachlorphene
Triclosan
Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion
kg/year) from petroleum.

2. ‫ــ‬1
It is an important industrial commodity as a precursor to many materials and useful compounds.[4]
Its major uses involve its conversion to plastics or related materials. Phenol and its chemical
derivatives are key for building polycarbonates,epoxies, Bakelite, nylon, detergents, herbicides
such as phenoxy herbicides, and numerous pharmaceutical drugs.
Although similar to alcohols, phenols have unique distinguishing properties. Unlike in alcohols
where the hydroxyl group is bound to a saturated carbon atom,[5]
in phenols the hydroxyl group is
attached to an unsaturated ring such as benzene or other arene ring.[6]
Consequently, phenols have
greater acidity than alcohols due to stabilization of the conjugate base through resonance in the
aromaticity.
Properties
Phenol is appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.88 M).
Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are
also possible. The sodium salt of phenol, sodium phenoxide, is far more water soluble
.
2 ‫ــ‬
Acidity
Phenol is weakly acidic and at high pHs gives the phenolate anion C6H5O−
(also called
phenoxide):[7]
PhOH PhO⇌ −
+ H+
(K = 10−10
)
One explanation for the increased acidity over alcohols is resonance stabilization of the phenoxide
anion by the aromatic ring. In this way, the negative charge on oxygen is delocalized on to the
ortho and para carbon atoms.[8]
In another explanation, increased acidity is the result of orbital
overlap between the oxygen's lone pairs and the aromatic system.[9]
In a third, the dominant effect
is the induction from the sp2
hybridised 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
Phenoxide anion
3 ‫ــ‬

3. The phenoxide anion has a similar nucleophilicityto free amines, with the further advantage that
its conjugate acid (neutral phenol) does not become entirely deactivated as a nucleophile even in
moderately acidic conditions. Phenols are sometimes used in peptide synthesis to "activate"
carboxylic acids or esters to form activated esters. Phenolate esters are more stable toward
hydrolysis than acid anhydrides and acyl halides but are sufficiently reactive under mild
conditions to facilitate the formation of amide bonds
Reactions
Phenol is highly reactive toward electrophilic aromatic substitution as the oxygen atom's pi
electrons donate electron density into the ring. By this general approach, many groups can be
appended to the ring, via halogenation, acylation,sulfonation, and other processes. However,
phenol's ring is so strongly activated—second only to aniline—that bromination or chlorination of
phenol leads to substitution on all carbons ortho and para to the hydroxy group, not only on one
carbon.
4 ‫ــ‬
When a mixture of phenol and benzoyl chloride when shaken in presence of dilute sodium
hydroxide solution, phenyl benzoate is formed. This is an example of Schotten-Baumann reaction:
C6H5OH + C6H5COCl → C6H5OCOC6H5 + HCl
Phenol is reduced to benzene when it is distilled with zinc dust or its vapour is passed over
granules of zinc at 400 °C:[15]
C6H5OH + Zn → C6H6 + ZnO
Production
Because of phenol's commercial importance, many methods have been developed for its
production. The dominant current route, accounting for 95% of production (2003), involves the
partial oxidation of cumene (isopropylbenzene) via the Hock rearrangement:[4]
C6H5CH(CH3)2 + O2 → C6H5OH + (CH3)2CO
Compared to most other processes, the cumene-hydroperoxide process uses relatively mild
synthesis conditions, and relatively inexpensive raw materials.
5 ‫ــ‬
However, to operate economically, there must be demand for both phenol, and the acetone by-
product.
An early commercial route, developed by Bayer and Monsanto in the early 1900s, begins with the
reaction of a strong base with benzenesulfonate:[16]
C6H5SO3H + 2 NaOH → C6H5OH + Na2SO3 + H2O
Other methods under consideration involve:

4.  hydrolysis of chlorobenzene, using base or steam (Raschig–Hooker process):[17]
C6H5Cl + H2O → C6H5OH + HCl
Uses
The major uses of phenol, consuming two thirds of its production, involve its conversion to
precursors to plastics. Condensation with acetone gives bisphenol-A, a key precursor to
polycarbonates and epoxide resins. Condensation of phenol, alkylphenols, or diphenols with
formaldehyde gives phenolic resins, a famous example of which is Bakelite.
6 ‫ــ‬
Partial hydrogenation of phenol gives cyclohexanone, a precursor to nylon. Nonionic detergents
are produced by alkylation of phenol to give thealkylphenols, e.g., nonylphenol, which are then
subjected to ethoxylation.[4]
Phenol is also a versatile precursor to a large collection of drugs .
Toxicity
Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract.[37]
Repeated or
prolonged skin contact with phenol may cause dermatitis, or even second and third-degree burns.
[38]
Inhalation of phenol vapor may cause lung edema.[37]
The substance may cause harmful effects
on the central nervous system and heart, resulting in dysrhythmia, seizures, and coma.[39]
The
kidneys may be affected as well. Long-term or repeated exposure of the substance may have
harmful effects on the liver and kidneys.[40]
There is no evidence that phenol causes cancer in
humans.[41]
Besides its hydrophobic effects, another mechanism for the toxicity of phenol may be
the formation of phenoxyl radicals.[42]
7 ‫ــ‬
.8 ‫ــ‬
Antiseptics
Antiseptics are chemical agents that slow or stop the growth of micro-organisms (germs) on
external surfaces of the body and help prevent infections.
Antiseptics should be distinguished from antibiotics that destroy micro-organisms inside the body,
and from disinfectants, which destroy micro-organisms found on inanimate (non-living) objects.
However, antiseptics are often referred to as skin disinfectants.
Most chemical agents can be used as both an antiseptic and a disinfectant. The purpose for which
it is used is determined by its concentration. For example hydrogen peroxide 6% solution is used
for cleansing wounds, while stronger solutions (>30%) are used in industry as a bleach and
oxidising agent.
Types of antiseptics

5. Antiseptics can be classified according to their chemical structure. Commonly used antiseptic
groups include alcohols, quaternary ammonium compounds, chlorhexidine
9 ‫ــ‬
and other diguanides, antibacterial dyes, chlorine and hypochlorites, inorganic iodine compounds,
metals, peroxides and permanganates, halogenated phenol derivatives and quinolone derivatives.
Uses of antiseptics
 Handwashing – chlorhexidine gluconate and povidone iodine solutions are often used in
hand scrubs and hand rubs.
 Pre-operative skin disinfection – antiseptics applied to the operation site to reduce the
resident skin flora.
 Mucous membrane disinfection – antiseptic irrigations may be instilled into the bladder,
urethra or vagina to treat infections or cleanse the cavity prior to catheterization.
 Preventing and treating infected wounds and burns – antiseptic preparations are available
over-the-counter from your pharmacist to treat minor cuts, abrasions and burns.
10 ‫ــ‬
Summary :
Phenol is the original antiseptic, old name carbolic acid. This was used by Lister, who discovered
antiseptics. It works well but is rather toxic.
Properties
Phenol is appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.88 M).
Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are
also possible
Antiseptics
Antiseptics are chemical agents that slow or stop the growth of micro-organisms (germs) on
external surfaces of the body and help prevent infections.
Types of antiseptics
Antiseptics can be classified according to their chemical structure. Commonly used antiseptic
groups include alcohols, quaternary ammonium compounds, chlorhexidine
11 ‫ــ‬
References

6.  Kütt, Agnes; Movchun, Valeria; Rodima, Toomas; Dansauer, Timo; Rusanov, Eduard B.;
Leito, Ivo; Kaljurand, Ivari; Koppel, Juta; Pihl, Viljar; Koppel, Ivar; Ovsjannikov, Gea; Toom,
Lauri; Mishima, Masaaki; Medebielle, Maurice; Lork, Enno; Röschenthaler, Gerd-Volker;
Koppel, Ilmar A.; Kolomeitsev, Alexander A. (2008). "Pentakis(trifluoromethyl)phenyl, a
Sterically Crowded and Electron-withdrawing Group: Synthesis and Acidity of
Pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline". The Journal of Organic
Chemistry 73 (7): 2607–20.doi:10.1021/jo702513w . PMID 18324831.
 Jump up^ http://omlc.ogi.edu/spectra/PhotochemCAD/html/phenol.html
 ^ Jump up to:a b c
Sigma-Aldrich Co., Phenol . Retrieved on 2013-07-20.
12 ‫ــ‬
 Book: Pharmaceutical Handbook. Ed Wade A. Nineteenth edition. The Pharmaceutical
Press.
 Antiseptics : Dr Joseph F. Smith Medical Library
5 ‫ـ‬^ Jump up to:a b c
Weber, Manfred; Weber, Markus; Kleine-Boymann, Michael (2004).
"Phenol". Ullmann's Encyclopedia of Industrial
Chemistry.doi:10.1002/14356007.a19_299.pub2 . ISBN 3527306730.
 Jump up^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book")
(1997). Online corrected version: (2006–) "Alcohols ".
 Jump up^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book")
(1997). Online corrected version: (2006–) "Phenols ".
 Jump up^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry:
Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience .
13 ‫ــ‬
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