What would be the good method and solvent to purify biphenyl?

In summary, the question is asking for the best method and solvent to purify biphenyl contaminated with fluorene. The melting points of both substances are similar, but fluorene is more polar due to an acidic proton. Options for purification include crystallization and using a strong base like NaOH to deprotonate fluorene, making it more soluble in a polar solvent like alcohol. Shaking the sample with NaOH and ether can separate the biphenyl from fluorene, with biphenyl remaining in the ether phase. This information could have helped in getting the correct answer for the lab.
  • #1
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Homework Statement



what would be the good method and solvent to purify biphenyl contaminated with fluorene?


Homework Equations







The Attempt at a Solution



The polarity of biphenyl (MP: 68.93°C) and fluorene (MP: 116-117°C ) are same which is non polar but their MP is hugh different. So, I'm not so sure which solvent is good to use. I think cryatallization would be the good method to purify. Could you help on this? Thank you so much.
 
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  • #2
Fluorene has an acidic proton and the anion is stabilized by aromatic stabilization. NaOH is apparently a strong enough base to deprotonate it.

You could also use an alcohol like butanol or butanol + ether.
 
  • #3
Thanks for help, It's kind of still confusing becaue the question is asking about to purify the biphenyl from fluorene.
 
  • #4
Fluorene is somewhat acidic (NaOH can deprotonate it) and is therefore more polar than biphenyl. It would more soluble in a polar solvent like alcohol. What would happen if you were to shake a sample containing fluorene with NaOH and ether? Would you find the fluorene in the organic or the aqueous phase? Would the biphenyl stay in the ether phase or would it cross over into the aqueous phase as well?
 
  • #5
Thank you so much. It makes sense NaOH and ether will sepearte biphenyl from Fluorene because biphenyl will stay in ether phase. If I understood this earlier, then I would have got the right answer for my lab. Well, Still I'm so happy that I know now. Thank you again!
 

1. What is the purpose of purifying biphenyl?

The purpose of purifying biphenyl is to remove any impurities or contaminants that may be present in the compound. This ensures that the biphenyl is of high quality and suitable for its intended use.

2. What factors should be considered when choosing a purification method for biphenyl?

Some factors to consider when choosing a purification method for biphenyl include the solubility of biphenyl in different solvents, the boiling point of biphenyl, and the availability and cost of the chosen method.

3. What are some common methods used to purify biphenyl?

Some common methods used to purify biphenyl include recrystallization, vacuum distillation, and column chromatography.

4. What are the advantages and disadvantages of using different solvents for purifying biphenyl?

The advantages of using different solvents for purifying biphenyl include the ability to target specific impurities and the ease of solvent removal. However, some solvents may be expensive or toxic, and may not be suitable for certain purification methods.

5. What precautions should be taken when handling biphenyl during purification?

It is important to wear appropriate personal protective equipment, such as gloves and a lab coat, when handling biphenyl. This compound can also be flammable, so precautions should be taken to avoid ignition sources. Proper ventilation should also be ensured to prevent inhalation of biphenyl vapors.

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