November 26, 2024, 12:27:11 PM
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Topic: base catalysed transesterification with methanol - biodiesel production  (Read 2976 times)

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Offline ajax0604

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Could someone help me understand the mechanism behind the reaction? I've read a number of resources but I'm still having trouble understanding it fully, mostly concerning the intermediate molecules that are formed prior to the final product of methyl esters.
From what I've read, the process involves hydrolysis followed by condensation. The OH- from NaOH attacks the carbonyl group on the triglyceride - this is the hydrolysis part? Are the intermediate molecules at this point three fatty acids and the glycerol backbone? Then the methanol reacts with the three fatty acids to produce the methyl esters - this is the condensation part? What happens to the glycerol backbone at this point? Where does it get the three protons required to complete its structure? Is it from water molecules that were released in the condensation reaction? 
Thank you.

Offline Hunter2

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This will not go in same time. First the fat acid salts (soap) and glycerole are produced by hydrolysis with sodiumhydroxide.  The Ester reaction can only take place with the acids itself, so an addition of sulfuric will convert them. In Access the sulfuric works as catalyst to do the ester reaction with the methanol.

Offline Babcock_Hall

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If one dissolves NaOH in methanol, this will produce sodium methoxide.  This species can attack the carbonyl group of a triacylglycerol to produce a fatty acid methyl ester (FAME).

Offline Hunter2

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if I dissolove NaOH in methanole the equilibrium will be  on the side of hydroxide and methanole. sodiummethoxide will be hydrolyzed by water.

NaOH + CH3OH <= CH3ONa + H2O

So I dont agrre the reaction takes place with the fat.

If sodium metal is dissolved in methanole then it maybe be possible.

2 Na + 2 CH3OH => 2 CH3ONa + H2


Offline Babcock_Hall

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Why do you say that the equilibrium will favor NaOH?

Offline Hunter2

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Because its nature that Methoxide will hydrolyse in wet enviroment.

Offline clarkstill

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Because its nature that Methoxide will hydrolyse in wet enviroment.

Do you mean protonate?  Anyway, if a small amount of NaOH is dissolved in MeOH, the predominant basic species will certainly be methoxide.  The pKa difference is negligible, (alhough, if anything methanol is slightly more acidic: 15.54, vs 15.7 for water), so the prevailing factor will be the concentrations of water vs ethanol.  Clearly since ethanol is the solvent, you can just apply Le Chatelier's principle and deduce that the major species at equilibrium will be methoxide, with a small quantity of hydroxide.

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