Separating Benzophenone and Salicyclic Acid in Diethyl Ether

In summary: It is possible that the low recovery is due to a reaction between the acid and the benzophenone, but this is just a guess at this point.
  • #1
zmike
139
0
Background:

Extraction lab using diethyl ether as solvent. Mixed an unknown mixture of benzophenone and salicyclic acid. Try to separate the 2.2 Questions:

1 In separation of ether sol'n from NaOH layer, some of the sol'n was left behind in the ether solution, how would that change the benzophenone recovery? Also indicate the top and bottom layer.

2 Suggest reasons for low benzophenone recovery .

My Attempt:

1. I think benzophenone dissolves in water while the diethyl ether dissolves the acid. If I am right, the diethyl ether should be at the bottom?

As for the recovery, it would decrease since you would be leaving behind benzophenone in the ether sol

2. ? I have no idea except for it evaporating but there should definitely be something important here since everyone got low recovery.

THANK YOU!
 
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  • #2
What do you know about those two compounds? What happens when you mix aqueous NaOH solution with a solution containing salicylic ACID? Sodium salts of weak acids are usually soluble in water.
 
  • #3
do u have any ideas on the low benzophenone rxn? I saw this radical rxn on wikipedia for it but I donno if that's right?
 
  • #4
zmike said:
do u have any ideas on the low benzophenone rxn? I saw this radical rxn on wikipedia for it but I donno if that's right?

Best guess right now is that no reaction of benzophenone is significant in this extraction. The guess could be wrong. Would enolization occur to benzophenone, and might this influence the extraction process? This is one for the organic chemist members of the forum.
 
  • #5
Enolization would require at least one alpha proton. Benzophenone has none and thus no enolization will occur under these conditions.

The reaction you saw in Wikipedia is for the ketyl of benzophenone and is a free radical. You need an active metal like sodium or potassium to generate it.
 

1. What is the purpose of separating Benzophenone and Salicyclic Acid in Diethyl Ether?

The purpose of this separation is to isolate and purify each compound for further analysis or use in experiments. Benzophenone and Salicyclic Acid are often found together in mixtures, and separating them allows for a better understanding of their individual properties.

2. How is the separation of Benzophenone and Salicyclic Acid accomplished?

The separation is typically done using a liquid-liquid extraction method, where the mixture of Benzophenone and Salicyclic Acid in Diethyl Ether is shaken with an aqueous base. This creates two distinct layers, with the organic layer containing Benzophenone and the aqueous layer containing Salicyclic Acid.

3. Why is Diethyl Ether used in this separation process?

Diethyl Ether is a common organic solvent that is immiscible with water, making it ideal for liquid-liquid extractions. It is also relatively non-polar, which helps to dissolve Benzophenone and Salicyclic Acid. Additionally, Diethyl Ether has a low boiling point and is easily evaporated, making it easy to remove from the final separated compounds.

4. What are the properties of Benzophenone and Salicyclic Acid?

Benzophenone is a white crystalline solid with a melting point of 48.5-49.5°C, and it is often used as a UV absorber in sunscreen and plastic products. Salicyclic Acid is a white crystalline powder with a melting point of 158-161°C, and it is commonly used in skincare products as an exfoliant and anti-inflammatory agent.

5. What are the potential applications of Benzophenone and Salicyclic Acid?

Benzophenone and Salicyclic Acid have a variety of industrial and pharmaceutical applications. Benzophenone is used as a building block in the production of plastics and dyes, while Salicyclic Acid is used in the production of aspirin and other medications. Both compounds also have potential uses in research and experiments in fields such as chemistry and biology.

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