Comments on: Transesterification https://www.masterorganicchemistry.com/2022/11/10/transesterification/ Wed, 03 Apr 2024 01:44:56 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Understanding the Process of Biofuel Production https://www.masterorganicchemistry.com/2022/11/10/transesterification/#comment-689466 Wed, 03 Apr 2024 01:44:56 +0000 https://www.masterorganicchemistry.com/?p=33200#comment-689466 […] for biofuel production. The efficient utilization of biomass through processes like fermentation, transesterification, and gasification is essential for converting it into biofuels. Understanding the diverse sources […]

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By: James Ashenhurst https://www.masterorganicchemistry.com/2022/11/10/transesterification/#comment-648860 Sat, 25 Feb 2023 03:58:18 +0000 https://www.masterorganicchemistry.com/?p=33200#comment-648860 You are most welcome!

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By: ERJ https://www.masterorganicchemistry.com/2022/11/10/transesterification/#comment-648847 Fri, 24 Feb 2023 23:44:57 +0000 https://www.masterorganicchemistry.com/?p=33200#comment-648847 That was very helpful! Thank you so much James!

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By: James Ashenhurst https://www.masterorganicchemistry.com/2022/11/10/transesterification/#comment-648652 Wed, 22 Feb 2023 04:12:12 +0000 https://www.masterorganicchemistry.com/?p=33200#comment-648652 In reply to ERJ.

Hi, the acidity of methanol, water and glycerol are all very similar – within an order of magnitude of each other which in acidity terms is a very, very small difference. Any of these species can act as acids here. I don’t know your exact conditions but if you were using MeOH as solvent then its concentration will be >> the concentration of any other possible acid in solution.
If you drew MeOH as the acid you would largely be correct; it doesn’t really matter since all protons are identical anyway and there will be reverse acid-base equilibria occurring in solution between all the hydroxyl groups.

I should note that even in neutral water, the protons on H2O undergo very fast exchange with other H2O molecules. Protons are very dynamic. If you ever take an NMR spectrum of an alcohol or a carboxylic acid you will note that these peaks tend to be quite broad, which is due to their relatively fast motion compared to more static protons such as C-H that do not undergo these kinds of exchange processes.

Hope that’s helpful – James

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By: ERJ https://www.masterorganicchemistry.com/2022/11/10/transesterification/#comment-648631 Tue, 21 Feb 2023 22:40:06 +0000 https://www.masterorganicchemistry.com/?p=33200#comment-648631 Hi there,
If anyone can answer this question, I would be eternally grateful. This article was very helpful but I am stuck on one thing. I created biodiesel in the lab, and I used methoxide (MeO-) as the nucleophile for the transesterification reaction by combining NaOH with MeOH. I also used a large excess of just MeOH as the solvent. However, I don’t understand how the glycerol is formed in the mechanism. Is the pre-glycerol alkoxide intermediate protonated by the water that is created in the reaction between NaOH and MeOH, or is it protonated by the excess MeOH solvent that I added? Initially, I thought it must be the water since that would regenerate the -OH (catalyst from NaOH). However, Note 1 in this article makes me think it’s the excess MeOH solvent that protonates it. But this leaves me confused about the catalyst part… Can anyone explain this mechanism to me? Oleic Acid + Methanol = Methyl Esters + Glycerol using a base catalyst (NaOH + MeOH = H2O + NaOMe) and excess methanol solvent.

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