Organic Chemistry

posted by .

How would you purify Fluorene contaminated with ethyl-4-aminobenzoate? What method and solvent you would use? Please help...

  • Organic Chemistry -

    Fluorene is a polycyclic aromatic hydrocarbon that is soluble in non polar solvents.

    Ethyl 4-amino benzoate is soluble is dilute aqueous acids and solvents like ethyl acetate.

    If you partition the mixture between cold 0.1 M HCl and a nonpolar solvent, say petrolum ether, in a separating funnel. The aqueous layer will contain the amine and the organic layer the fluorene. Separate. Wash the aqueous layer once with petrolum ether. Combine the organics in a separating funnel and wash the mixture again with dilute acid. Evaporate the organic to recover the fluorene.
    If you need to recover the amine. Return the aqueous layer to a separating funnel add base, extract with ethylacetate.

  • Organic Chemistry -

    I have just had a few further thoughts. You didn't say how much fluorene you have or the % contamination. If you have a relatively small amount (50 mg - 1g) a small chromatography column would be quick. Pack a small column with silica gel. Take up the mixture in a small volume of petroleum ether (you may need to add a few % of ethyl acetate to get it all in solution). Load onto the column and flush through with petroleum ether. The amine will stick to the origin and the fluorene will pass straight through.

    An even sneakier (quick and dirty) way is to dissolve/suspend the mixture in petroleum ether in a beaker and add silica gel. The amine will stick to the silica. Filter the mixture, wash the silica with petroleum ether. Evaporate the pet ether to recover the fluorene.

  • Organic Chemistry -

    thank you so much Dr. Russ...yes the question assumes the containment comprises only a small percentage of the mixture...

    p.s.: do u happen to know the answer to my other question as well? under the same assumptions...

Respond to this Question

First Name
School Subject
Your Answer

Similar Questions

  1. Best solvent?

    What is the best solvent for impure fluorene?
  2. Chemistry

    How would you purify decanoic acid contaminated with biphenyl?
  3. Chemistry

    how do you purify Biphenyl contaminated with Fluorene?
  4. Organic Chemistry

    How would you purify biphenyl contaminated with fluorene?
  5. science

    an ethereal solution contains benzoic acid, 9-fluorenone, and ethyl 4-aminobenzoate. why would ethyl 4-aminobenzoate and 9-fluorenone not be extracted from this ethereal solution by aqueous base?
  6. Organic Chemistry Lab

    For this week's lab, we have to devise our own separation and purification scheme. The mixture contains three compounds, however my problem lies in the fact that the composition isn't given to us. There are four possible combination …
  7. chemistry

    Which solvent would dissolve each of the following compounds?
  8. Organic chemistry

    We conducted a diels-Alder reaction of cyclopentadiene with Maleic Anhydride experiment. Though I was wondering why we added ligroin to the maleic anhydride and ethyl acetate. I know ligroin can be used as a solvent, but I thought …
  9. Organic chemistry

    A diels-Alder reaction of cyclopentadiene with Maleic Anhydride experiment was conducted in lab. But I was wondering why we added ligroin to the maleic anhydride and ethyl acetate. I know ligroin can be used as a solvent and it is …
  10. Chemistry Urgent Help Please!

    Give two means other than crystallization from a solvent that may be used to purify an organic solid. Explain Pleaseeeee!!!!!!!!!!!!!

More Similar Questions