Lawrence Klomps

Recrystallization: A Process for Purifying Compounds

Introduction
Chemistry is an essential part of everyday life and is applicable to just about any product one can
imagine. If it were not for chemistry, the world's average life expectancy would be much lower.
The development of organic chemistry techniques, for instance, applies to the synthesis of many
medications. Of particular interest is recrystallization, a purification process that removes
impurities from crystalline chemical compounds. There are five fundamental concepts to this
process: 1) selecting suitable solvents; 2) dissolving a compound in a minimal amount of solvent;
3) removing impurities; 4) initiating crystallization; and 5) collecting the crystals. One should be
familiar with general or organic chemistry before continuing to read this process description.
Selecting Suitable Solvents
The ability of a chemist to choose a suitable solvent is the key to maximizing the yield of pure
crystals. More often than not, a suitable recrystallization solvent has 1) a similar polarity and 2)
has a lower boiling point than the melting point of the compound of interest.
Using a solvent of similar polarity allows the compound to dissolve into solution upon heating
and facilitates reformation of pure crystals by retaining impurities in solution. Solvent polarities
vary and many chemists will use trial and error to find the appropriate solvent, following a
spectrum of polarities to determine an ideal solvent (see fig. 1).
Selecting the wrong solvent usually results in an immiscible liquid or undesired reactions with
the compound. In more complex recrystallizations, chemists may employ multiple solvents based
on the principle of "like-dissolves-like" to extract impurities by using solvents that have
polarities more similar to the impurities instead of the compound of interest. Ideally, compounds
to be purified should be completely insoluble in cold solvent but dissolve readily in hot solvent.

Figure 1. A general spectrum of polarity differences; solvents with oxygen, such as water (left)
are more polar than hydrocarbons such as cyclohexane (right).
Image source <http://www.waters.com/waters/nav.htm?cid=10049076&locale=en_US.>

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Solvents must also have a boiling point lower than the melting point of the compound to be
purified. Generally, if the boiling point is higher than the melting point, boiling the solvent will
cause the compound to melt or "oil out" of solution. In this situation, the solid turns to an oil and
often gives poor recrystallization results (see fig. 2). Overall, oils are unfavorable because they
retain impurities and can sometimes fail to recrystallize, resulting in potential loss of the
compound.

Figure 2. "Oiling out" of a compound with a melting point less than the boiling point of water.
Image source <http://chemistry.gcsu.edu/~metzker/Principles/Notes-BLBB/CH13-Solutions.html>

Dissolving the Compound in a Minimum Amount of Solvent
Chemists are very conservative with the materials they use, not only because most are expensive,
but also because many chemistry techniques require minimal amounts of materials, such as in
recrystallization. Chemists often make the mistake of adding too much solvent when dissolving a
compound of interest. The primary goal is to actually use a minimum amount of solvent to create
a saturated, hot solution. Minimal usage of solvent facilitates crystallization since like-molecules
collide more frequently, as opposed to being too diffused in excess solvent.
Removing Impurities
There are many ways that chemists remove impurities and they are large processes in themselves
and cannot be explained within the scope of this text. However, the idea that chemists employ is
universal: one must be efficient in saving the desired product. Some apparatuses that chemists
use include pipet filtration, a process in which one uses a pipet to suck up the impurities or
vacuum filtration which utilizes filter paper that collects solid impurities (see fig. 3 below).
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Figure 3. A simple vacuum filtration apparatus used for isolating impurities.
Image source <http://en.wikipedia.org/wiki/File:Vacuum-filtration-diagram.png>

Initiating Crystallization
Crystallization is the process in which molecules collide with each other to form an ordered,
repeating geometric structure. This process can take a few seconds or days to occur.
Crystallization is different from precipitation in that precipitation is the formation of a solid from
a reaction that separates into solution spontaneously upon mixing reactants.
Crystallization is induced in several ways but is usually facilitated by using an ice bath or some
other means to reduce the solvent temperature. Slow, undisturbed cooling, however, will produce
the highest yield of crystals. One common method for inducing crystallization is by scratching
the beaker or test tube holding the solvent. This will produce microscopic scratches in the glass,
providing a substrate on which the crystals can grow.
A last resort technique chemists employ for crystallization is seeding in which a chemist
introduces a pure form of the compound to jumpstart the process. If no pure compounds are
available, some chemists may use a small fragment of the impure compound to have the same
aforesaid effect, though they typically avoid this. Another crystallization method that is not
encouraged is evaporation (boiling off the solution) since it leads to recollection of impurities.
Crystals will usually form slowly in a lattice network as depicted in the figure below (fig. 4).
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Figure 4. Formation of crystals over time from a solvent mixture.
Image source <http://answers.tutorvista.com/1086791/need-of-crystallization.html#close_iframe>
Collecting the Crystals
Collecting crystals after crystallization completes the process of recrystallization. Chemists
accomplish this in several ways with vacuum filtration being the most common type of filtration
that chemists use (refer back to fig. 3). In addition to collection, chemists wash their crystalline
product with some cold solvent-of-choice that they used in the crystallization process. Washing
the crystals with uncontaminated solvent further purifies the desired compound by removing any
impurities that were caught in the crystal lattice upon filtration. Allowing the crystals to sit and
dry concludes the process of recrystallization.
Conclusion
Overall, recrystallization is not one, but several distinct processes that chemists must understand.
First, a solvent resembling the polarity of the compound of interest dissolves everything into
solution when heated with a minimal amount of solvent. Cooling of the solution allows the
crystallization process to occur, allowing for recollection of the purified compound using
different methods of filtration. Lastly, the crystals are washed with uncontaminated solvent and
the purified compound is left to dry. Dissolving a crystallized compound and restoring its
crystalline structure to a purer form defines recrystallization; hence the re- in recrystallization.
This process is a powerful tool since many chemists will repeat the recrystallization process
multiple times for one compound to maximize its purity. For instance, pharmaceutical companies
use recrystallization to purify medications that would otherwise be lethal in their impure form.
Understanding the basic principles and logic of recrystallization is key to forming the purest
crystals from the most impure compounds.

Lawrence Klomps
ENGL 202C Assignment Four: Definition and Description
Evaluation Sheet
1. Audience Accommodation: The definition and description are understandable and useful for
the intended audience. Language and content consistently and clearly indicate a specific
audience. The description provides information at a consistent level of understanding.
Weak_____ Fair______ Good______ Great______

2. Content: The document is complete (includes all the necessary information to describe the
product or process, including sentence, parenthetical and extended definitions as fit). Sentence
definitions include an appropriately specific category. The purpose is clear, even if not explicitly
stated. The titles enhance coherence. Transitions support reader comprehension.
Weak_____ Fair______ Good______ Great_______

3. Organization: The introduction effectively sets up the description. The document uses an
organizational pattern appropriate to the product or process (functional, spatial, or
chronological). The conclusion includes appropriate information.
Weak_____ Fair______ Good_______ Great______

4. Format/Design Layout: The description uses visuals when necessary to help the specific
audience understand the object or process. The overall design is clear and consistent, providing
important information at a glance. The description uses fonts, white space, contrast, alignment,
headings and sub-headings appropriately and consistently.
Weak_____ Fair______ Good_______ Great______

5. Style/Mechanics: The tone is effective for the audience and consistent throughout description.
Headings and numbered and bulleted items are in parallel form (that is, they use similar
grammatical structures for each item in a list and for the text of headings). The document uses
technical writing conventions. The document is free from typographical or grammatical errors.
Weak_____ Fair______ Good_______ Great______

Overall Grade______________