Beruflich Dokumente
Kultur Dokumente
Miguel, K.D., Moron, R.S.S., Pazon, A.D., Ramirez, C.V., Raquepo, T.M.R., Razon, D.N.A.Jr.
2B-PH, Group No. 6, Department of Pharmacy, Faculty of Pharmacy,
University of Santo Tomas, Espaa Boulevard, 1015 Manila, Philippines
Abstract
Recrystallization is a widely used technique and is an important technique in purifying organic
compounds. It involves dissolving a material to be purified (the solute) in an appropriate hot
solvent to yield a solution. As the solvent cools, the solution becomes saturated with respect to
the solute (saturation level), which then recrystallizes. As the perfectly regular array of crystal is
formed, impurities are excluded, and the crystal is thus a pure substance. [1] A suitable solvent in
purifying solid compounds carries the characteristic of allowing the compound (to be purified) to
be very soluble to the solvent at its boiling point, and only sparingly soluble at its room
temperature.[2] This report presents the procedure on how to perform recrystallization: choosing
the suitable solvent for purification, acetylation of aniline with acetic anhydride to synthesize
crude acetanilide, purification of crude acetanilide, and gathering the crystals obtained from the
pure acetanilide. It also contains the equations and calculations used in this experiment. The
percentage yield calculated from the experiment is 77.70%. The actual yield is 2.3g. This is the
pure acetanilide obtained from aniline and acetic anhydride.
Introduction
Various purification methods can be
done in natural organic compounds since
these compounds, whether solid or liquid,
contain impurities. The method of
purification is determined by different
physical and chemical characteristics of a
certain compound. [3] For liquids,
evaporation, and distillation are examples of
purification methods. Distillation is the most
commonly used process which is primarily
based on the boiling points of the
compounds used. For solids, purification can
be done through sublimation, adsorption,
and recrystallization. Organic compounds
purified through sublimation pass directly
into the vapour phase without passing
through the liquid phase. Organic
compounds that lack this property may be
purified through recrystallization, which is
Upon
heating
Soluble
Soluble
Upon
cooling
Insoluble
Soluble
Water
Methano
l
Hexane
Insoluble Insoluble Insoluble
Table 1 Solubility of acetanilide in
various solvents
Acetylation
Acetic
of
Aniline by
Anhydride
Purification of Crude
Recrystallization
Acetanilide
by
2.30 g
x 100
%
2.96 g
77.70
Percentage Recovery=
2.3 g
x 100
4.0 g
57.50%
References
[1] Williamson, K. L., & Masters, K. M. (2011). Organic Experiments Macroscale and
Microscale.Washinton, DC: Charles Hartford.
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October 5, 2015, from erowid.org:
https://www.erowid.org/archive/rhodium/chemistry/equipment/recrystallization.html
[3] Brown, W. H., & Poon, T. (2011). Introduction to Organic Chemistry (4th Edition). Hoboken,
New Jersey: John Wiley & Sons.
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Encyclopaedia Britannica: http://www.britannica.com/science/separation-and-purification
[5] Williamson, K. L., & Masters, K. M. (2011). Organic Experiments Macroscale and
Microscale.Washinton, DC: Charles Hartford.
[6] Barnes,M. (2014). Recrystallization. Retrieved October 6, 2015, from Chem Mass:
http://www.chem.umass.edu/~samal/269/cryst1.pdf
[7] Mullin, J. W. (2001). Crystallization (4th edition) .London, England: Butterworth & Co.
[8] Berry, J. (2004, September). UW Madison. Retrieved from Chem Wisk:
http://www.chem.wisc.edu/courses/342/Fall2004/Recrystallization.pdf
[9] Saunders. (2007). Dorland's Medical Dictionary for Health Consumers. Elsevier, Inc.
Retrieved from Medical Dictionary: http://medical-dictionary.thefreedictionary.com/acetylation
[10] Pahlavan, D. (n.d.). Experiment 5- Preparation of Acetanilide. Retrieved from Southwest
College: http://swc2.hccs.edu/pahlavan/2423L5.pdf
[11] Athabasca University. (n.d.). Retrieved from science.pc:
http://science.pc.athabascau.ca/labinfo.nsf/0/a39dc67b2da8ed33872570cd005ebbc1
[12] Organic Chemistry at CU Boulder. (2015, August 31). Retrieved from
orgchem.colorado.edu.ph:
http://orgchem.colorado.edu/Technique/Procedures/Filtration/Filtration.html