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HW
HW
After separation of the organic and the aqueous layer, the amine can be recovered by addition of
a strong base like NaOH or KOH to the acidic extract i.e., lidocaine synthesis. Note that amides
are usually not basic enough to undergo the same protonation (pKa of conjugate acid: ~ -0.5).
additional 5 mL of 2 M NaOH solution to rinse the brown residue out of the flask, and
1M sodium hydroxide.
2. Compare the solid products obtained after extraction and purification. Account
for the difference between the two solids.
The solid product obtained after extraction was a dark powder. The dark
color is due to the presence of other components, since it is not pure
caffeine yet. The solid product obtained after purification was a white
powder. By then, the impurities have already been removed. It can be said
that the powder is pure caffeine.
The solid obtained after extraction was a dark powder. It is not yet pure
caffeine so it has other components that account for its dark color. On the
other hand, the solid obtained after purification were white crystals. This is
because itsalready mostly caffeine as the impurities were already removed.
The solid obtained after extraction was a dark powder while the solid
obtained after purification werewhite crystals. The solid obtained from
extraction is not yet pure caffeine so it has many other components thatmay
be the reason of its dark color. The solid obtained after purification is mostly
caffeine because theimpurities from the solid after extraction is purified
which is why it looks like white crystals
3. What are the other applications of solvent extraction?
Other applications of solvent extraction are:
solvent extraction in precious metal refineries which includes three
mechanisms ion-pair formation, salvation, and compound formation
waste water treatments - metal treatment from acidic and ammoniacal
waste solutions, recovery of acids (hydrofluoric, nitric, phosphoric, arsenic);
separation of organic pollutants
Solvent Extraction in Biochemical and Pharmaceutical Separations:
extraction of carboxylic, amino acids, and penicillin.
Solvent Extraction in Organic and Biofuels Separation: petroleum and
petrochemical treatment, separation of isomers, and ethanol processing.
remediation of soils with contaminated hydrocarbons where the dissolved
can be removed,
Other applications of solvent extraction include isolation of certain odors or
flavors in food, purification of amines and extraction of certain metals. Also,
it is applied to DNA purification in which the nucleases that destroy DNA
are washed out.
http://www.sciencedirect.com/science/article/pii/B9780444537782100056
http://www.slideshare.net/kumarsachin3801/industrial-application-ofsolvent-extraction-technique
4. What are the different phase changes that occur during purification using
sublimation?
Sublimation, which can be used to purify substances, is a phase transition
without entering into an intermediate liquid phase. The different phase
change processes that occur are sublimation and depositon. At a high
tempereature, the solid caffeine changes to its gaseous state. Upon contact
with the cool surface of the beaker, a lower temperature causes the gaseous
caffeine to undergo deposition. It cools back down and changes back to its
solid form, depositing on the sides of the beaker and on the filter paper.
Sublimation is a phase transition process from a solid to a gas without ever entering an
intermediate liquid phase
It is not as selective as crystalization, it typically requires a vacuum and usually requires that the
compound you are trying to separate is volatile, while everything else in the mixture is not
volatile.
the vapor pressure of the substance must be different than the vapor pressure of the impurities,
otherwise both substances will be transported into the gas phase in almost equal amounts and
compound you are trying to separate is volatile, while everything else in the mixture is not
volatile.
http://www.linfield.edu/assets/files/chem/Courses/CHEM%20321/2014-week3-4caffeine-chem321l-53ebfd7b679e5.pdf
http://www.chem.ucalgary.ca/courses/351/laboratory/351expt_06_caffeine_exp.pdf
EXPERIMENT 4
1. Why is the chromatogram developed in an essentially closed system?
The chromatogram is developed in a closed system, since the solvents are
highly volatile and vaporize easily. This prevents the solvent from
evaporating. It is also for maintaining a balanced solvent vapor in the
container. The plate must have the same exposure and saturation to the
vapors. An open system can create a gradient. Another reason is to prevent
other gaseous substances from entering and mixing with the solvents.
The chromatogram needs to be in a closed system as the solvents are highly
volatile, meaning they easily vaporize. Also, this allows the container to be
saturated with the vapour of the solvent. The closed system also ensures
that no other gaseous substances may enter the chromatogram and mix with
the solvents or stain the chromatography paper.
The chromatogram is developed in a closed system in order to prevent the solvent
to evaporate. Most solvents used in the chromatograph are toxic and flammable. It is
also put in a close system to reduce the chance of outside factors affect the
chromatograph.
plate above the solvent pool has the same exposure to solvent vapors. The assumption is the
solvent vapor is the same throughout the container. If you had an open system, you would get a
gradient and the vapor level would change.
the closed system maintained the column chromatography efficiency by preventing the
formation of column bubbles. The system was efficient in reducing solvent evaporation as
well as preventing water condensation at the column outlet. Since free solvent vapors
were eliminated, the system provided an additional safety factor when a flammable
solvent, was employed.While the columns were used for solvent cleanup, a small
modification would transform the system into a solute purification apparatus.
which will allow us to separate the substance based on their rate of travel up the
chormatographic plate. Depending on the polarity of the substance present, they will
travel at different rates in the presence of different polarity solvent systems.
Ultraviolet Light Detection: A nondestructive visualization technique that will show any
compounds that absorb UV light. Compounds containing benzene rings or conjugated
systems usually absorb UV light. Commercial TLC plates have phosphor in the
adsorbent, which fluoresces in short-wave UV light. If a compound is present on the plate
it blocks the glow and appears as a dark spot. (This is technically true only for
compounds that quench the fluorescence). Some organic compounds also fluoresce
themselves, and will show up as bright spots under short-wave UV light.
Iodine vapor: Iodine vapor is also a non-destructive visualization technique. A few
crystals of iodine are placed in a closed chamber, such as a capped jar containing silica
gel, and the slide is placed into the chamber to collect on the spots by a weak electronic
attraction. Iodine forms a yellow or brown complex with most organic compounds
containing double bonds, even isolated ones. The reaction is reversible, so that I2 staining
can be followed by another chemical stain if the plate is allowed to sit in air for several
minutes so that the iodine can sublime off the plate.
Please note that while these two methods will show any compounds containing double
bonds, any compounds without double bonds will not show up on your plate (unless they
are themselves colored, in which case you will be able to see them with your naked eye).
Other TLC visualization methods exist for these compounds, but they are usually strong
oxidizers and for that reason not safe for use in an undergraduate lab.