Introduction

Unsurprisingly, one of the biggest scientific accomplishments is the variety of potent medical
medicines that are currently accessible. Over the course of many decades, scientists discovered
a generous number of procedures to successfully formulate products such as drug crystals
(Adibkia et al., 2011). Chemicals may be modified in different ways including recrystallization, a
simple and low-cost technique for bringing drug research to a commercial scale.

One of the most significant technique for purifying solid nonvolatile organic compounds is

recrystallization. Although they are frequently used interchangeably, the words "crystallization"
and "recrystallization" actually refer to two separate processes. Crystallization refers to the
creation of a highly-organized-structure solid via chemical processes, whereas Recrystallization
simply allow crystals to re-form. In a nutshell, a recrystallization technique involves dissolving
the substance to be purified in a suitable solvent. The solute crystallizes out of solution when
the solvent cools because it is saturated with the solute. Impurities are eliminated from the
crystal lattice as the crystal forms, which marks the end of the purification process. The crystals
are then gathered, washed with ice-cold water, and dried.

Recrystallization is not a perfect technique. Like any purification technique, it has its own sets of
limitations. First of which is the fact that all compounds to be experimented must be a solid at standard
conditions since greases, waxes and oils cannot be crystallized at such circumstance. Moreover, because
some of the component will be soluble in a cold solvent, a portion of the compound is always lost.
Recrystallization won't produce a pure compound if there is a significant amount of impurity having
the same solubility characteristics as the test substance. Another disadvantage of this technique is that it
takes a long time (LibreTexts, 2021). On a brighter note, it is a very effective and accurate way of
obtaining pure samples when performed correctly.
With all of those said, the objective of this experiment includes the following:

- To identify the appropriate solvent for the recrystallization technique.

- To us the recrystallization technique in purifying a solid sample.
Methods

This experiment is divided into two major parts: solubility test and actual recrystallization process. The
materials required to conduct this experiment include Buchner funnel, Thomas-Hoover melting
apparatus, hot plate, stemless funnel, funnel support, micro test tubes, test tube rack, Erlenmeyer fask,
beaker, capillary tubes, oven, and reagents to be tested.

The first step in recrystallizing an impure compound is to identify the best solvent appropriate for the
technique – having high solubility at high temperatures and low solubility at low temperatures. This was
accomplished by placing about 0.10 g of solid samples inside a micro test tube. Their solubility was
observed by dissolving it in 2mL prepared cold solvents which include water, ethanol, benzene, and
ethyl acetate. Those mixtures that did not dissolve were boiled and once again observed if soluble or
not. The results observed from this part of the experiment were utilized in the actual recrystallization
process.

For part 2, approximately 3.50 g of the test compound (crude acetanilide) was dissolved in a pre-heated
30mL water. The mixture was boiled in a hot plate and was consecutively added with 2mL water until
the white solid completely dissolved. The total solvent used was only 70mL since the solubility of
acetanilide is 4.30g/100mL water. At this point, the solution was not colored so addition of activated
carbon was not necessary. Using the hot gravitation filtration set-up (Figure 1), the solution was filtered
with the help of the fluted filter paper situated in the stemless glass funnel. Once the solution was
completely filtered, the flask containing the filtrate was removed from the hot plate and was allowed to
cool down to room temperature. It was then placed in an ice bath and was continuously stirred until
crystallization is complete. After 10 to 15 minutes, the solution was vacuum filtered (Figure 2). The
crystals were washed with 2mL cold water and were dried in the oven for another 15 mins. After which,
the crystals were weighed in the analytical balance and its purity was identified by observing its melting
point with the use of the Thomas-Hoover Apparatus (Figure 3).
 Figure 1. Hot Gravity Filtration Set-up

Figure 2. Vacuum Filter using Buchner Funnel

Figure 3. Melting Point Determination Using Thomas-Hoover Apparatus

https://sites.pitt.edu/~ceder/add_info/recrystallization.html
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Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Physical_Properties_of_Matter/
Solutions_and_Mixtures/Case_Studies/RECRYSTALLIZATION

https://chemistnotes.com/organic/recrystallization-definition-meaning/

Discussion

The first step in removing soluble impurities is conducting solubility tests on the known compounds.
Later on, such solubility tests will be used to find a suitable recrystallization solvent for an unknown
compound. A compound usually exhibits one of three general solubility behaviors: (1) the compound
has a high solubility in both hot and cold solvent, (2) the compound has a low solubility in both hot and
cold solvent, and (3) the compound has a high solubility in hot solvent and a low solubility in cold
solvent. Solvents which exhibit the first two behaviors are not useful for recrystallizing a compound. A
solvent showing the third behavior is one that is suitable for use as a recrystallization solvent. Another
criterion for a good recrystallization solvent include not reacting with the substance being purified and
dissolving impurities readily at low temperatures. It is also important to note that in choosing a
solvent, the bigger the difference between hot solubility and cold solubility, the more product
recoverable from recrystallization.

In this experiment, the researchers tested the solubility of various compounds (1 – acetamide, 2 –
acetanilide, 3 – aspirin, 4 – benzoic acid, 5 – naphthalene, 6 – sucrose) in four separate solvents. Table 1
summarizes the results observed by the researchers.

*Solubility (S – soluble; I – insoluble)

Since the appropriate recrystallization solvent are those that dissolve samples in high temperatures,
only one or two solvents will be applicable in each sample (Table 2).

*Solvent Appropriate for Recrystallization*

As seen in Table 2, water is the most suitable solvent to recrystallize acetanilide. Upon dissolving the
test compound in the solvent, it is best to avoid unnecessary large volume to recover a good amount of
purified material. The amount of material lost can be reduced to the minimum by dissolving the sample
in the least amount of hot solvent. As practice by most chemists, 35% more solvent than the minimum
required is used so that the hot solution will be not quite saturated (Klepper, 2009). This aids in avoiding
crystal separation and filter paper clogging while filtering the hot solution.
In some cases, resinous impurities leave traces of color in the mixture which must be removed with
selective absorbents such as activated charcoal. Fortunately, the researcher’s test compound was clear,
making them filter it directly. It is necessary to filter the solution while it is still hot to get rid of insoluble
contaminants. Otherwise, crystals form too early when the solution cools. Rapid filtration can be
accomplished by folding it into lots of small triangles. This is more efficient since it provides larger
surface area where the solvent can seep through (Nagwa, n.d.).

Then, the compound is dissolved in the solvent, which has been heated to just below or at boiling. The
solution is then allowed to cool to room temperature. Once this has happened, it can then be cooled in
an ice bath to further induce crystallization. The solubility decreases as the temperature does, leaving
the solution to become saturated with the pure compound. At this point, it begins to crystallize. The
impurities are left in the solution, and removing the crystals from the solution also rids the impurities
from them. Lastly, the crystals are rinsed with ice-cold solvent, cleaning off any remaining impurities.

- Actual recrystallization
- Explain importance nung bawat steps

o Hindi immediately placed sa ice bath after hot filtration

o Coll the filtrate in ice bath
o Vacuum filtration is used habang malamig pa
o Cold crystals washed with water
- function nung activated carbon at bakit hindi na ginamit

The purity of the recrystallized compound can now be verified by comparing how similar the
experimental melting point is to the compound’s published melting point. If necessary, multiple
recrystallizations can be performed until the purity is acceptably high.

- Melting point comparison. Experimental result and yung nasa literature. Report percent
error.

Conclusion

In a nutshell, recrystallization is a method of purifying a compound by removing any impurities

that might be mixed with it.
Recrystallization produces a purer final product. For this reason, experimental procedures that
produce a solid product by crystallization normally include a final recrystallization step to give
the pure compound.

This experiment shows that

Recrystallizations require careful technique and practice. Some loss, resulting from transferring solids
from one container to another and leaving a little material behind, cannot be avoided. Such losses
should however be minimized as much as possible by using careful technique. Also, because of the finite
solubility of the solid in the recrystallization solvent, even at low temperatures, any unnecessary
prolonged contact with recrystallization solvent, especially if the solvent is not ice-cold will result in loss
of product.

The following problems encountered which contributed to the large amount of error include the
following: (1) too much solvent added in the recrystallization – resulting in a poor yield of crystals, (2)
solid sample dissolved below the boiling point of the solution – requiring more solvent to be used which
results in a poor yield, (3) use of rinse solvent that is not ice cold – redissolving some of the products
formed, and (4) low temperature hot gravity set up – not producing enough steam which lets the
compound crystallize in the filter paper and not reach the filtrate. Because of this, it is recommended for
future researchers to use a boiling solvent for recrystallization process and an ice-cold solvent for
rinsing. It is also important to let the water (used in hot gravity set up) boil vigorously to create more
steam and melt larger amount of pure crystals.

References:

Adibkia, K., Hamedeyazdan, S. & Javadzadeh, Y. (2011). Drug release kinetics and physicochemical
characteristics of floating drug delivery systems. Expert Opin Drug Deliv, Vol.8, No.7, pp. 891-903, ISSN
1744-7593

Libretexts (2021) -
https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/
Supplemental_Modules_(Physical_and_Theoretical_Chemistry)/Physical_Properties_of_Matter/
Solutions_and_Mixtures/Case_Studies/RECRYSTALLIZATION

Klepper R. R. (2019) - file:///C:/Users/DELL/Downloads/ORG%20LAB%20Recrystallization2009.pdf

Nagwa (n.d.) - https://www.nagwa.com/en/videos/806147396206/

Helpful!!!

https://www.jove.com/v/10184/purifying-compounds-by-recrystallization