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1. Terminology.
Partitioning. This is a distribution of a material between two or more phases.
Drying. As applied to organic chemistry, this means the removal of water from a
liquid. Organic liquids can be wet (containing water) or dry (containing little or no
water).
Decanting. This is the process of pouring off a liquid and leaving a solid or
sediment behind.
Emulsion- One liquid held in a suspension within another liquid. Mayonnaise is
an emulsion of oil in water and lemon juice. Emulsions are usually an undesirable
occurrence when attempting a separation or extraction.
Distribution coefficientiv is a numerical assessment of the ratio of a compounds
solubility in an organic solvent over that in water.
The caffeine extraction procedure has several steps which are required but the
reason for doing them may not be obvious. Here are some explanations.
Sodium carbonate is a base. Caffeine is an alkaloid, an organic base. Tannins
contains phenolic OH groups on aromatic rings which are acidic. Sodium
carbonate is added in the first extraction to make sure that 1) the caffeine
remains in the free base form (that is, to prevent it from reacting with any
acids that may be present and form a cation) and 2) to reacts with the
acidic phenolic groups of the tannins rendering them ionic and keeping
them in the aqueous phase when the liquid-liquid extraction is carried out.
An emulsion is a suspension of one liquid as droplets in another (the two liquids
must be insoluble in one another). Emulsions are almost always
undesirable. To avoid them, you can shake mixtures of insoluble liquids
gently, and add salt to aqueous layers. You will use a centrifuge in this
experiment break them up once they form.
5.
percentage of caffeine =
6. The purity and identity of the isolated material will be determined via TLC. Review
methods and calculations related to TLC before coming to lab. The TLC
plate is white and caffeine is white. Caffeine cannot be seen on a TLC
plate without the use of an ultraviolet (UV) light or other imaging
technique. The caffeine absorbs the UV light and gives off visible light.
This phenomenon is called fluorescence. The caffeine is clearly visible on
the TLC plate under UV light but invisible under normal lighting.
7. There are some systematic errors in this experiment as it is performed. For example,
the tea is not weighed by itself but instead it is weighed along with the string, tea
bag and a staple. When the liquid tea is separated from the tea bag, some of the
liquid (containing caffeine) remains behind in the wet bag. The distribution
coefficient of caffeine between water and dichloromethane is not perfect; some
caffeine will remain dissolved in the water. Dichloromethane evaporates rapidly,
cooling the watch glass as it does; water can condense on the cool watch glass,
influencing the weight of your final product.
8.
9. Methylene chloride and water are not miscible and have low solubilities in each other.
This means when they are added together they do not mix and form two distinct
layers. Water has a density at 25C of 1.00 g/mL. Most organic liquids have a
density less than 1.0 g/mL. That is why gasoline and oil float on top of water.
Methylene chloride contains 2 very heavy chlorine atoms (35.5 g/mol) which
results in a high density of 1.33 g/mLviii. Density determines which liquid will be
on top and which on the bottom. When methylene chloride and water are added
together, which is predicted to float?
10. The solubility of caffeine varies substantially based on the temperature of the
solvent and the solvent identity. ix
Solvent, Temperature
Caffeine Solubility (g caffeine / 100g solvent)
o x
Water, 25 C
2.26
Water, 80 o C
20
o xi
Water, 100 C
67
o viii
Methylene Chloride, 25 C
8.45
Caffeine has a much higher solubility in hot water than room temperature (25C) water.
Caffeine is almost four times more soluble at room temperature in methylene chloride
as it is in water. Therefore the caffeine is extracted from the solid tea leaves into boiling
water. The extract is allowed to cool. The caffeine is then extracted from the room
temperature water into the liquid methylene chloride due to a favorable distribution
coefficient.
11.
References:
i
Tea Revives the World, G.S. Haley Company http://www.gshaly.com/resources/teashistory.htm (March 24, 2012)
NationMaster, Food Consumption: Tea http://www.nationmaster.com/graph/foo_tea_con-food-tea-consumption
(March 24, 2011)
iii
Roasting Coffee, Moore Coffee and Tea Company, http://www.moorecoffee.com/french/roasting.html (March 24,
2012)
iv
Ramette, Chemical Equilibrium and Analysis, Addison-Wesley Publishing, London 1981 p574-575
v
Encyclopedia Britanica, Camellia, http://www.britannica.com/EBchecked/topic/90798/Camellia (November 2,
2012)
vi
D. Pavia, G. Lampman, G.Kriz, R. Englel, A Microscale Approach to Organic Laboratory Techniques, 5 th Edition,
Brooks/Cole, Belmont CA, 2013, p100-101.
vii
Hackhs Chemical Dictionary, 5th Edition, McGraw-Hill, New York,1969 p26.
viii
CRC Handbook of Chemistry and Physics, 65th edition, CRC Press, 1985, C-372
ii
ix
K. L. Williamson, Macroscale and Microscale Organic Experiments, Houghton Mifflin Company, 3rd Edition,
1999.. pp146-150
x
Shalmashi, A., Golmohammad, F., Latin American Applied Research, vol. 40., no 3, July 2010
http://www.scielo.org.ar/scielo.php?pid=S0327-07932010000300012&script=sci_arttext (accessed December 11,
2013)
xi
Sigma-Aldrich, Product Information Caffeine https://www.sigmaaldrich.com/etc/medialib/docs/SigmaAldrich/Product_Information_Sheet/c0750pis.Par.0001.File.tmp/c0750pis.pdf
(Accessed December 11, 2013)