on 3/15/04 6:34 AM, Leif Forer at [EMAIL PROTECTED] wrote:

>
> 
> Ideal vegetable oil is triglycerides.
> Due to factors....the triglycerides can break
> into mono and di-glycerides, also known as free
> fatty acids and enemy of transesterification.

First some basics -- alcohols (glycerol, methanol,
ethanol, etc.) can "condense" with organic acids
(acetic, oleic, lysergic, etc.). In the process,
a water molecule is released and an "ester" is formed
(ethyl lysergate, methyl oleate, etc.)

In the case of glycerol, three alcohol groups (OH)
are present in the one molecule, so this esterif-
ication can happen one, two, or three times.
As you know, a triester of glycerol with three
fatty acid molecules is called a triglyceride, and
is what we call a "vegetable oil" . If any fatty
acids are present in the oil that AREN't condensed
with a glycerol molecule, they're called
FREE fatty acids.


> 
> We add a base catalyst to facilitate the cracking
> of the triglyceride.


I really wish everyone would stop using that term
"cracking" for transesterification -- it really
conveys the wrong idea. It's a petroleum term
meaning to break a long carbon chain into shorter
chains, and it causes a lot of confusion.

What you do for biodiesel is break the ester links
between the glycerol and the fatty acids in the
original oil, and create a new ester link between
each separated fatty acid and a short alcohol like
methanol or ethanol. In other words, you break
(and re-esterify) a single molecule of, say,
glyceryl trioleate into a  molecule of glycerol
and three molecules of methyl oleate.



> Aren't mono and di-glycerides formed when the
> triglyceride is cracked?


They are formed when the triglyceride is attacked
by WATER, which also releases one of the fatty acid
tails as a free fatty acid.


> If so, why can't the FFA's bond with the added
> methyl alcohol to form methyl esters?


This reaction occurs in the presence of acid catalyst,
but not base catalyst. That's why a first step of
acid catalysis can be used to methylate any free fatty
acids prior to the usual base-catalyzed step.

I'm home sick today -- plenty 'o' time fer chem
questions..... :-)



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