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Author: Subject: nonmetal reducing agent like LAH
smartgene1
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[*] posted on 29-12-2016 at 09:14
nonmetal reducing agent like LAH


Is there a non metal reducing agent that just like lithium aluminum hydride. Something like thiourea dioxide to sodium borohydride but more powerful. Powerful enough to reduce carboxylic acid
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AvBaeyer
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[*] posted on 29-12-2016 at 15:12


Sodium borohydride will easily reduce carboxylic acids via an ester, imidazolide, mixed anhydride or other carboxylic acid activating groups. There is much in the accessible literature about this. I also recollect that this has been discussed on the board before along with posted pertinent refeernces. Try a search and see what you can find.

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NitratedKittens
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[*] posted on 8-1-2017 at 09:44


What carboxylic acid are you trying to reduce, some more information would be handy.



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PHILOU Zrealone
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[*] posted on 8-1-2017 at 10:30


Non metal reducing agent for carboxylic acid....

Carbon
Nascent H2
Formic acid
C=O
Formaldehyde
Coenzyme Q – cytochrome c reductase
Phosphines
Hypophosphites
BH3
SiH4
Hydrazine

But may require harsh conditions of temperature or pressure.




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[*] posted on 8-1-2017 at 10:46


Quote: Originally posted by AvBaeyer  
Sodium borohydride will easily reduce carboxylic acids via an ester, imidazolide, mixed anhydride or other carboxylic acid activating groups. There is much in the accessible literature about this. I also recollect that this has been discussed on the board before along with posted pertinent refeernces. Try a search and see what you can find.

AvB



The problem with sodium borohydride is that it is not strong enough to reduce esters.




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PHILOU Zrealone
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[*] posted on 8-1-2017 at 13:37


Did you read the OP title?

NON METAL...
--> No Na, Li, K, Al, ... allowed!




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[*] posted on 8-1-2017 at 18:52


FYI - Borohydride easily reduces esters in the presence of methanol. Many refs to this reduction are easily found.

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smartgene1
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[*] posted on 10-1-2017 at 12:17


how can carbon reduce carboxylic acid
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Tsjerk
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[*] posted on 10-1-2017 at 12:34


Heat it
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zed
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[*] posted on 10-1-2017 at 14:01


Does electricity count?
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symboom
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[*] posted on 10-1-2017 at 19:49


Powerful reducing agents

Gallium 1 oxide can reduce sulfuric acid to H2S
Https://en.m.wikipedia.org/wiki/Gallium


Sodium dithionite
https://en.m.wikipedia.org/wiki/Sodium_dithionite


Titanium chloride
https://en.m.wikipedia.org/wiki/Titanium(II)_chloride

And probally other compounds with low oxidation states
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PHILOU Zrealone
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[*] posted on 11-1-2017 at 14:25


Quote: Originally posted by smartgene1  
how can carbon reduce carboxylic acid

Like written:
"But may require harsh conditions of temperature or pressure."

Electricity via reductive electrolysis is another way...but hard without metal (as wire or as electrolyte)
Kolbe electrolysis is a disguised way:
2 CH3-CO2H --> CH3-CH3 + 2 CO2 + H2




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[*] posted on 12-1-2017 at 06:04


Sodium borohydride and iodine in THF will react to form a borane-THF complex that can reduce carboxylic acids and even amino acids to alcohols.
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[*] posted on 12-1-2017 at 06:25


Would the reaction between iodine and borohydride give NaI, H2 and BH3?
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[*] posted on 12-1-2017 at 08:05


Probably eventually, but since I2 is an oxidizer, it would probably first form NaI, HI, and BH3, then the HI would react with another NaBH4 to form NaI, H2, and BH3.
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