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Is there a way to convert aniline to phenol without diazotizing it?
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+ Amines
+ Aniline
+ Phenols
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Posted by
Mel Siegel
Is there a way to convert aniline to phenol without diazotizing it?
Benzenediazonium salt is so versatile that it can be used to make many compounds. That's why, diazotization reaction is so popular and useful. The reaction conditions is not that harsh and is easily achievable. Coming to the reaction, diazotization is a straight one-way procedure to achieve aniline to phenol conversion. If you talk about other ways of converting aniline to phenol, the reaction conditions for such ways are generally harsh and hence not done practically to obtain phenol. In addition, there are so many steps, that the conversion is practically not feasible.
One of the ways of converting aniline to phenol without diazotizing is to convert aniline to acetanilide and then hydrogenolyze it to make benzene which can be then used to make phenol.
Step 1
Step 2
The reaction is taken from a paper1. The paper discussed the use of $\ce{NiMo}$ based catalyst along with novel neo-microporous composite material HSM/ZSM-5 as support. The reaction result is compared with other supports like $\ce{\gamma-Al2O3}$ and lone ZSM-5 and HSM system.
Step 3
Reference
Sajedeh Jafarian, Ahmad Tavasoli, Hasan Nikkhah, "Catalytic hydrotreating of pyro-oil derived from green microalgae spirulina the (Arthrospira) plantensis over $\ce{NiMo}$ catalysts impregnated over a novel hybrid support," International Journal of Hydrogen Energy2019, 44(36), 19855-19867 (https://doi.org/10.1016/j.ijhydene.2019.05.182) 44. 10.1016/j.ijhydene.2019.05.182(PDF).
Benzenediazonium salt is so versatile that it can be used to make many compounds. That's why, diazotization reaction is so popular and useful. The reaction conditions is not that harsh and is easily achievable. Coming to the reaction, diazotization is a straight one-way procedure to achieve aniline to phenol conversion. If you talk about other ways of converting aniline to phenol, the reaction conditions for such ways are generally harsh and hence not done practically to obtain phenol. In addition, there are so many steps, that the conversion is practically not feasible.
One of the ways of converting aniline to phenol without diazotizing is to convert aniline to acetanilide and then hydrogenolyze it to make benzene which can be then used to make phenol.
Step 1
Step 2
The reaction is taken from a paper1. The paper discussed the use of $\ce{NiMo}$ based catalyst along with novel neo-microporous composite material HSM/ZSM-5 as support. The reaction result is compared with other supports like $\ce{\gamma-Al2O3}$ and lone ZSM-5 and HSM system.
Step 3
Reference
Sajedeh Jafarian, Ahmad Tavasoli, Hasan Nikkhah, "Catalytic hydrotreating of pyro-oil derived from green microalgae spirulina the (Arthrospira) plantensis over $\ce{NiMo}$ catalysts impregnated over a novel hybrid support," International Journal of Hydrogen Energy2019, 44(36), 19855-19867 (https://doi.org/10.1016/j.ijhydene.2019.05.182) 44. 10.1016/j.ijhydene.2019.05.182(PDF).
Step 2 does not guarantee hydrogenation would stop at benzene, it may continue to give cyclohexane under the conditions. It is also possibility that N-ethylaniline may converted to cyclohexylethylamine first, which then hydrogenalize to cyclohexane. I attached the PDF in the reference for your information.More
Benzenediazonium salt is so versatile that it can be used to make many compounds. That's why, diazotization reaction is so popular and useful. The reaction conditions is not that harsh and is easily achievable. Coming to the reaction, diazotization is a straight one-way procedure to achieve aniline to phenol conversion. If you talk about other ways of converting aniline to phenol, the reaction conditions for such ways are generally harsh and hence not done practically to obtain phenol. In addition, there are so many steps, that the conversion is practically not feasible.
One of the ways of converting aniline to phenol without diazotizing is to convert aniline to acetanilide and then hydrogenolyze it to make benzene which can be then used to make phenol.
The reaction is taken from a paper1. The paper discussed the use of $\ce{NiMo}$ based catalyst along with novel neo-microporous composite material HSM/ZSM-5 as support. The reaction result is compared with other supports like $\ce{\gamma-Al2O3}$ and lone ZSM-5 and HSM system.
Reference
Benzenediazonium salt is so versatile that it can be used to make many compounds. That's why, diazotization reaction is so popular and useful. The reaction conditions is not that harsh and is easily achievable. Coming to the reaction, diazotization is a straight one-way procedure to achieve aniline to phenol conversion. If you talk about other ways of converting aniline to phenol, the reaction conditions for such ways are generally harsh and hence not done practically to obtain phenol. In addition, there are so many steps, that the conversion is practically not feasible.
One of the ways of converting aniline to phenol without diazotizing is to convert aniline to acetanilide and then hydrogenolyze it to make benzene which can be then used to make phenol.
The reaction is taken from a paper1. The paper discussed the use of $\ce{NiMo}$ based catalyst along with novel neo-microporous composite material HSM/ZSM-5 as support. The reaction result is compared with other supports like $\ce{\gamma-Al2O3}$ and lone ZSM-5 and HSM system.
Reference
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