sodium hydroxide+ethanol+stearic acid reaction

[joeweller]

 

What is Reaction mechanism of sodium hydroxide, ethanol and stearic acid?

 

[hypervalent_iodine]

What do you think? What sort of functional groups are present? What sort of reagent is NaOH? What sorts of reactions do you know of involving these things?

 

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[Elite Engineer]

Esterification reaction. Understanding the mechanism is up to you...

[TheFreak]

Hi! Since you two seem to know what is going on here, could you please explain it? Because I am puzzled by this reaction. Now obviously I thought of esterification, however as far as I know (and could find), that requires an acid catalyst, not a base. The base is used for saponification. So it is esterification but with the catalyst for reverse esterification? That makes no sense right? Or is the sodium hydroxide used as some sort of dehydration agent? I came to this question via this video, where you can see the reactants: https://youtu.be/7ddpV8R6pFo?t=137 Either I'm stupid or I should throw my bachelor degree in chemistry in the bin, but I don't understand this.

[hypervalent_iodine]

1 hour ago, TheFreak said:

Hi! Since you two seem to know what is going on here, could you please explain it? Because I am puzzled by this reaction. Now obviously I thought of esterification, however as far as I know (and could find), that requires an acid catalyst, not a base. The base is used for saponification. So it is esterification but with the catalyst for reverse esterification? That makes no sense right? Or is the sodium hydroxide used as some sort of dehydration agent? I came to this question via this video, where you can see the reactants: https://youtu.be/7ddpV8R6pFo?t=137 Either I'm stupid or I should throw my bachelor degree in chemistry in the bin, but I don't understand this.

 

I mean, I never said it was an esterification. I don’t believe it is, for the reasons you’ve noted. You can generate esters using base and the carboxylic acid, but you would need to pair it up with the alkyl halide rather than the alcohol. Can be a bit finicky, but it’s doable.

[TheFreak]

I see. Would you possibly have another explanation then for what is happening in the video? I remain puzzled to what is going on.

[John Cuthber]

On 6/7/2016 at 8:56 PM, Elite Engineer said:

Esterification reaction. 

I'd bet against that.

 

[hypervalent_iodine]

13 hours ago, TheFreak said:

I see. Would you possibly have another explanation then for what is happening in the video? I remain puzzled to what is going on.

They're making solid alcohol. I believe, but am not sure, that once you make the carboxylate with the NaOH, that plus the heat you generate allows for the alcohol to become encapsulated, giving you a powder. You can use a similar process to make gels using Ca(CH₃CO₂)_2. Other types of commercial solid alcohol use carbohydrates (see here).  

[ginaboyle275]

I think you need to give further details on what is it for. It's hard to conclude by imagination.

[Elite Engineer]

On 5/30/2019 at 1:38 PM, John Cuthber said:

I'd bet against that.

 

Why's that? What other kind of reaction would you see with a fatty acid, ethanol, and hydroxide?

[hypervalent_iodine]

1 hour ago, Elite Engineer said:

Why's that? What other kind of reaction would you see with a fatty acid, ethanol, and hydroxide?

You won't get the ester. You have an acid and a base, you're just going to get deprotonation. You need an acid catalyst to get the ester. 

[Elite Engineer]

Oh right. I was thinking of saponification. Thanks for the clarification