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. (This is important when determining which layer contains which compounds) . and which is on bottom.

.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! Water Polar N-Hexane Non-polar Ethanol Polar Miscible Toluene Non-polar Miscible .

Ex. Amine Acid Ketone Alcohol .Water Soluble Compounds A) Small molecules (5 carbons or less) with at least one polar functional group.

sugars. etc... Glucose .) Ex.Water Soluble Compounds continued… B) Larger molecules with more than one polar functional group (polyfunctional compounds.

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Water Insoluble Compounds A) Molecules without polar functional groups. Ex. B) Monofunctional compounds with more than 5 carbon atoms. . Ex.

chloroform (CHCl3). it does not normally mean that such compounds are water soluble.Water Insoluble Compounds continued… •  Compounds such as methylene chloride (CH2Cl2). . and are used for extraction from aqueous solutions. and carbon tetrachloride (CCl4) are insoluble in water. •  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.

Type of compounds A) Acid: Proton donor (Bronsted definition) Acid (insoluble in H2O) Base (abstracts most acidic proton) Salt (H2O soluble Conjugate base) .

Type of compounds continued… B) Base: Proton acceptor (Bronsted definition) Acid Base (insoluble in H2O) (will be deprotonated) Salt (H2O soluble conjugate acid) .

amides. aldehydes. ethers. esters. . ketones.Type of compounds continued… C) Neutral Compounds Some examples: hydrocarbons.

What is our plan? •  •  Liquid-Liquid Extraction The compounds used: Acid: Benzoic acid Base: Ethyl 4-Aminobenzoate Neutral: 9-Fluorenone All insoluble in water .

Outline of the Procedure Ar-COOH acid Ar –NH2 Base Dissolve in Ether (Et2O = ether) Ar-COOH Ar-NH2 Ar-H HCl (aq) Et2O Ar-H Neutral Ar-COOH Ar-H Ar-NH3 + Cl- Et2O Et2O Ar-COOH Ar-H NaOH (aq) Ar-H Ar-COO – Na+ Et2O H2O Separate H2O H2O Ar-NH3 + Cl- Label: H2O w/Base .

..Outline of the Procedure continued. Et2O Separate Ar-COO – Ar-H Label: Et2O w/ Neutral 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 + Cl- NaOH (aq) Ar-NH2 (ppt) Dry Weigh Product Calculate % recovery Record MP H2O w/Base Reformation Reaction: Deprotonation Original H2O insoluble base is reformed (will crash out as a precipitate) .

Recovery of Acidic Compound Filter Ar-COO – Na+ HCl (aq) Ar-COOH (ppt) Dry Weigh Product Calculate % recovery Record MP H2O w/ Acid Reformation Reaction: Protonation Original H2O insoluble acid is 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 Cool and Weigh Compound Calculate % recovery Record MP Et2O w/ Neutral .

Reminders for Writing Lab Report •  Be sure to calculate the overall total % recovery and a % recovery for each component – total four % recoveries. •  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? . •  Different types of extraction techniques.

150 g) before you begin the extraction. . Each compound should account for approximately 0. •  Procedure is in the textbook. •  All the work must be your own only.Some Friendly Reminders •  There is no handout for this experiment.05 g of the original mixture. •  Make sure to weigh original mixture (about 0. •  Always heat solvents with a boiling chip or stick. Refer to Experiment [4C]. For detail information on plagiarism refer to syllabus.

•  Make sure to dispose of all waste properly. Label. . Label!!! •  Always vent the vial after shaking. •  Label.Friendly Reminders continued… •  Have to dilute 6M HCl and 6M NaOH to 3M by using equal parts distilled water and either acid or base. •  All lab work is to be performed in a hood.

What do we need…? .

Add acid to the mixture of three compounds in ether .

Organic OR Aqueous? .Which one is on top -----.

Layer separation… .

74) .Separation of Compounds (in Textbook pg.

NaOH. add aq. .To reprecipitate basic component from aqueous solution.

Help precipitation on Basic component… .

NaOH .To the remaining organic layer. add aq.

74) .Separation of Compounds (in Textbook pg.

. HCl. add aq.To reprecipitate acidic component from aqueous solution.

Now check the pH… .

benzoate Benzoic acid. 9-Fluorenone .Final products… Ethyl 4-Amino.

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