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Author: Subject: Reduction of organic acids without hydrides
ChemistryForever
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[*] posted on 12-12-2018 at 07:54
Reduction of organic acids without hydrides


As the title says, how can I reduce organic acids without hydrides? They are both expensive and hard to find ...
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Tsjerk
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[*] posted on 12-12-2018 at 11:52


Reduce to what? Aldehyde, alcohol, alkane? Is your acid substituted? Without details no one can give an answer.
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WGTR
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[*] posted on 12-12-2018 at 12:01


If we're talking about an organic acid like ethanoic acid, then heating the calcium or lithium salt can produce some acetone, which can then be reduced via hydrogenation to isopropanol in a tube furnace. Acetone can supposedly be reduced all the way to propane electrochemically, on a cadmium cathode. The combined efficiencies are probably not that great.



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clearly_not_atara
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[*] posted on 12-12-2018 at 12:06


WGTR: but you get a dimer!

If you form the ester you can reduce the acids to alcohols with sodium in ethanol.

If you form the nitrile you can reduce to the aldehyde with SnCl2/HCl in diethyl ether followed by hydrolysis.

If you form the aldehyde you can reduce to the alkane with hydrazine/KOH in ethylene glycol.

That should about cover it, I think.




[Edited on 04-20-1969 by clearly_not_atara]
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JJay
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[*] posted on 12-12-2018 at 18:20


How does calcium formate react with other calcium carboxylates at high temperatures?



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draculic acid69
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[*] posted on 15-12-2018 at 17:48


Will ethyl acetate when reduced with NaOet yield 2 moles of ethanol from 1 mole ethyl acetate?
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clearly_not_atara
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[*] posted on 15-12-2018 at 17:48


NaOEt is not a reducing agent. Sodium metal in alcohol generates electrons.

Quote: Originally posted by JJay  
How does calcium formate react with other calcium carboxylates at high temperatures?


Aldehyes are produced in low yield IIRC. Formaldehyde is also produced.

[Edited on 16-12-2018 by clearly_not_atara]




[Edited on 04-20-1969 by clearly_not_atara]
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I_love_Diethylether
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[*] posted on 16-12-2018 at 03:01


I was also wondering about reduction of Esters without hydrides. I didnt find anything good tho, however it is possible to reduce Aldehydes with water and precipitated Nickel to alcohols. An interesting review to read about this is linked.
Source: Kazuo Hata , Izumi Motoyama & Koji Sakai (1972) THE URUSHIBARA
HYDROGENATION CATALYSTS A REVIEW, Organic Preparations and Procedures International,
4:4, 179-209, DOI: 10.1080/00304947209355544
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Σldritch
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[*] posted on 16-12-2018 at 06:07


I have never heard of anyone doing it but from my understanding of the Clemmensen reduction mechanism should it not yield a primary alcohol?

[Edited on 16-12-2018 by Σldritch]
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