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Solvent Extraction

CHE-231 Organic Chemistry


University of Kentucky
Objectives

A) To separate a mixture containing an acidic,


basic, and neutral compound by liquid-liquid
solvent extraction.

B) To determine the purity of the separated


compounds by recording their melting points
and comparing to literature.
Background

Solvent Extraction:
A technique commonly used in organic chemistry
to separate compounds in a mixture, based on
the differing solubility behaviors of the
compounds.

Two Methods:
Solid-liquid extraction
Liquid-liquid extraction
Background continued…

 Liquid-Liquid extractions require that the two liquids


be immiscible when mixed together.
Ex.
Ether and H2O
or
Methylene Chloride and H2O

The densities will determine which layer is on top,


and which is on bottom. (This is important when
determining which layer contains which compounds)
Expressing the Solubility
of a Compound
Partition Coefficient:
[ X Solvent 2]
Kp = [ X Solvent 1]

When compound X is placed in a mixture of two


immiscible solvents, it will be distributed between the
two phases as a function of its relative solubility in
each solvent.
Solubility
•  Any substance (solid/ liquid) is soluble in another
substance (liquid), only if their chemical nature is similar
•  Polar substance is soluble in Polar solvent

•  LIKE DISSOLVES LIKE!

N-Hexane
Water
Non-polar
Polar Toluene
Ethanol
Non-polar
Polar

Miscible Miscible
Water Soluble Compounds

A) Small molecules (5 carbons or less) with at


least one polar functional group.
Ex.

Amine Acid Ketone

Alcohol
Water Soluble Compounds continued…

B) Larger molecules with more than one polar


functional group (polyfunctional compounds,
sugars, etc...)
Ex.

Glucose
Water Soluble Compounds continued…
C) Salts (ionic bonds) are soluble in water due to ion-
dipole interactions.

Ex. NaCl, KCl

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Water Insoluble Compounds

A) Molecules without polar functional groups.


Ex.

B) Monofunctional compounds with more than 5


carbon atoms.
Ex.
Water Insoluble Compounds continued…
•  Compounds such as methylene chloride (CH2Cl2),
chloroform (CHCl3), and carbon tetrachloride (CCl4) are
insoluble in water; and are used for extraction from
aqueous solutions.

•  Although the presence of a chlorine atom attached to a


carbon in a covalent C-Cl bond does lend some partial ionic
character due to the electronegativity of the chlorine, it
does not normally mean that such compounds are water
soluble.
Type of compounds
A) Acid:
Proton donor (Bronsted definition)

Base
Acid (abstracts most Salt
(insoluble in H2O) acidic proton) (H2O soluble
Conjugate base)
Type of compounds continued…

B) Base:
Proton acceptor (Bronsted definition)

Acid

Base (will be Salt


(insoluble in H2O) deprotonated) (H2O soluble
conjugate acid)
Type of compounds continued…
C) Neutral Compounds
Some examples: hydrocarbons, aldehydes,
ketones, ethers, amides, esters.
What is our plan?
•  Liquid-Liquid Extraction
•  The compounds used:

Acid:
Benzoic acid Neutral:
Base: 9-Fluorenone
Ethyl 4-Aminobenzoate

All insoluble in water


Outline of the Procedure
Ar-COOH
acid
Dissolve in Ether HCl (aq)
Ar –NH2
Base
(Et2O = ether) Ar-COOH
Ar-NH2 Et2O
Ar-H
Ar-H Neutral

Ar-COOH NaOH (aq) Ar-H Et2O


Et2O Ar-H
Ar-COOH
Ar-H Et2O Ar-COO –
H2O
Ar-NH3 + Separate Na+
Cl- H2O
Ar-NH3 +
H2O Label: H2O w/Base
Cl-
Outline of the Procedure continued...

Et2O Ar-H
Label: Et2O w/ Neutral
Separate
Ar-COO –
H2O Na+ Label: H2O w/ Acid

** Now all three components are separated. Each


component must now be isolated to reform and
recover the original forms of the compounds
Do not forget to label !!!
Recovery of Basic Compound
Filter
Ar-NH3 + NaOH (aq) Ar-NH2 Dry
(ppt)
Cl- Weigh Product
H2O w/Base Calculate % recovery
Record MP

Reformation Reaction:

Original H2O insoluble base is


Deprotonation reformed (will crash out as a
precipitate)
Recovery of Acidic Compound
Filter

Ar-COO – HCl (aq) Ar-COOH Dry


Na+ (ppt) Weigh Product

H2O w/ Acid Calculate % recovery


Record MP

Reformation Reaction:

Original H2O insoluble acid is


Protonation reformed (will crash out as a
precipitate)
Recovery of Neutral Compound

Dry with Na2SO4 (collect in a


Ar-H tare vial containing a boiling chip)
Slowly evaporate Ether
Et2O w/ Neutral Cool and Weigh Compound
Calculate % recovery
Record MP
Reminders for Writing Lab
Report
•  Be sure to calculate the overall total % recovery
and a % recovery for each component – total
four % recoveries.
•  Different types of extraction techniques.
•  How does the partition coefficient relate to this
lab?
•  How do you tell if something will be soluble?
•  What makes a compound acidic, basic or
neutral? How do we use this to change water
solubility?
Some Friendly Reminders
•  There is no handout for this experiment.

•  Procedure is in the textbook. Refer to Experiment [4C].

•  Make sure to weigh original mixture (about 0.150 g) before you begin
the extraction. Each compound should account for approximately
0.05 g of the original mixture.

•  Always heat solvents with a boiling chip or stick.

•  All the work must be your own only. For detail information on
plagiarism refer to syllabus.
Friendly Reminders continued…
•  Have to dilute 6M HCl and 6M NaOH to 3M by
using equal parts distilled water and either acid
or base.

•  Label, Label, Label!!!

•  Always vent the vial after shaking.

•  All lab work is to be performed in a hood.

•  Make sure to dispose of all waste properly.


What do we need…?
Add acid to the mixture of three
compounds in ether
Which one is on top
------ Organic OR Aqueous?
Layer separation…
Separation of Compounds
(in Textbook pg. 74)
To reprecipitate basic component from
aqueous solution, add aq. NaOH.
Help precipitation on Basic component…
To the remaining organic layer, add aq.
NaOH
Separation of Compounds
(in Textbook pg. 74)
To reprecipitate acidic component from
aqueous solution, add aq. HCl.
Now check the pH…
Final products…

Ethyl 4-Amino; Benzoic acid; 9-Fluorenone


benzoate