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Extraction and

Recrystallization
Chem 331, Lecture #3
September 17, 2018

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Extraction vs Washing
• Extraction in chemistry is a process consisting in the separation of a substance from a mixture through
dissolving it in the appropriate solvent (compound of intertest goes to a different phase).
• Washing in chemistry is a process consisting in the purification of a substance by dissolving (extracting)
the impurities in the appropriate solvent (compound of intertest stays in the same different phase).

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Gas-Liquid Extraction
• Isolation of a component of interests from a mixture of gases by selective dissolving it in a liquid.

• Extraction of ammonia
(water-soluble)
• Washing of nitrogen
(insoluble in water)

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Solid-Liquid Extraction
• Isolation of a component of interests from a solid matrix by selective dissolving it in a liquid.

• Coffee percolator
• Extracting caffeine and
other water-soluble
compounds from ground
coffee beans
• Refluxing
• Hot filtration
• Isolation of caffeine in
pure form (Crystallization,
Cold filtration)

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Refluxing
• Most materials are
better soluble in hot
solvents
• Boiling of a mixture,
while condensing
vapors are returning
back to a still pot
• Reflux condenser

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Crystallization

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Crystallization
• A: solubility in hot
solvent. Mass of
dissolved material:
(A x V) [g]
• B: solubility in cold A
solvent. Mass of lost
material:
(B x V) [g]
• (A – B) x V – mass of
material recovered after B
crystallization
• (A – B)/A*100% - yield
of crystallization Technique 11, p. 648

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Crystallization

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Crystallization

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Liquid-Liquid Extraction
• Isolation of a component of interests from a solution via partitioning between two immiscible
liquids.
• Immiscible liquids pair:
polar (hydrophilic, usually
water) and non-polar
(hydrophobic, usually
organic solvent)
• Polar compounds go to the
aqueous layer
• Non-polar compounds go
to the organic layer
• Density: top and bottom
layer. Most organic
solvents are lighter than
water. Halogenated
solvents are heavier than
water (CH2Cl2, CHCl3 etc.)

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Partition Coefficient (aka Distribution Constant)
𝐶𝑜𝑟𝑔 (𝑒𝑞𝑢𝑖𝑙𝑖𝑏𝑟𝑖𝑢𝑚 𝑐𝑜𝑛𝑐𝑒𝑛𝑡𝑟𝑎𝑡𝑖𝑜𝑛 𝑖𝑛 𝑜𝑟𝑔𝑎𝑛𝑖𝑐 𝑝ℎ𝑎𝑠𝑒) 𝑚𝑜𝑟𝑔 𝑉𝑎𝑞
• 𝐾 ≝ = ×
𝐶𝑎𝑞 (𝑒𝑞𝑢𝑖𝑙𝑖𝑏𝑟𝑖𝑢𝑚 𝑐𝑜𝑛𝑐𝑒𝑛𝑡𝑟𝑎𝑡𝑖𝑜𝑛 𝑖𝑛 𝑎𝑞𝑢𝑒𝑜𝑢𝑠 𝑝ℎ𝑎𝑠𝑒) 𝑉𝑜𝑟𝑔 𝑚𝑎𝑞

Example:
50 mg of compound was dissolved in 1 mL of water. Second extraction:
This solution was extracted twice with 0.5 mL of ether. 𝑚𝑜𝑟𝑔 𝑉𝑎𝑞 ∗
(𝑚𝑡𝑜𝑡𝑎𝑙 − 𝑚𝑎𝑞 ) 𝑉𝑎𝑞
How much of material was extracted, if K = 5 𝐾 ≝ ×
𝑉𝑜𝑟𝑔 𝑚𝑎𝑞
=
𝑉𝑜𝑟𝑔
×
𝑚𝑎𝑞

14.29 − 𝑚𝑎𝑞 1 𝑚𝐿
5 = ×
First extraction: 0.5 𝑚𝐿 𝑚𝑎𝑞
𝑚𝑜𝑟𝑔 𝑉𝑎𝑞 (𝑚𝑡𝑜𝑡𝑎𝑙 − 𝑚𝑎𝑞 ) 𝑉𝑎𝑞
𝐾 ≝ × = × 𝑚𝑎𝑞 = 4.08 mg; 𝑚𝑜𝑟𝑔 = 10.21 𝑚𝑔
𝑉𝑜𝑟𝑔 𝑚𝑎𝑞 𝑉𝑜𝑟𝑔 𝑚𝑎𝑞

50 − 𝑚𝑎𝑞 1 𝑚𝐿
5 = ×
0.5 𝑚𝐿 𝑚𝑎𝑞 Overall:

𝑚𝑎𝑞 = 14.29 mg = 𝑚𝑡𝑜𝑡𝑎𝑙 𝑚𝑎𝑞 = 4.08 mg;
𝑚𝑜𝑟𝑔 = 35.71 𝑚𝑔 𝑚𝑜𝑟𝑔 = 35.71 𝑚𝑔 + 10.21 𝑚𝑔 = 45.92 𝑚𝑔

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Partition Coefficient (aka Distribution Constant)
When multiple extractions are used, the amount of material remaining in the aqueous layer after i-step
can be calculated using the following formulas:

𝑖 𝑖
𝑖 = 𝑉𝑎𝑞 𝑉𝑎𝑞
• 𝐶𝑎𝑞 𝐶0 Or 𝑖 =
𝑚𝑎𝑞 𝑚0
𝑉𝑜𝑟𝑔 𝐾+𝑉𝑎𝑞 𝑉𝑜𝑟𝑔 𝐾+𝑉𝑎𝑞

For previous example:

𝑖 2
𝑖 = 𝑉𝑎𝑞 1 𝑚𝐿
𝑚𝑎𝑞 𝑚0 = × 50 𝑚𝑔 = 4.08 𝑚𝑔
𝑉𝑜𝑟𝑔 𝐾+𝑉𝑎𝑞 0.5 𝑚𝐿 × 5 +1 𝑚𝐿

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