quest
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Butyric Acid
Hi, I remember there was a thread about Butyric Acid but I just couldn't found it, so sorry for opening new thread.
In the other thread it was spoken about mixing NaOH, butter and water and preserve it on almost boiling point for about 30 minutes.
After this it wrote to use HCl on what has formed and you will get Butyric Acid.
Can any one tell me what happen in every stage of the reaction? and what formed?
thanks
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Pyridinium
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Offhand I'd say you're going to get a lot of other things mixed with your butyric acid. I think butter is only like 2-5% butyric acid.
Quick search on google shows the bulk of butter trigylcerides contain oleic, palmitic, myristic, and stearic.
The first step saponifies the fats of butter, making soaps with them and freeing glycerin (glycerol).
The HCl should then produce the free fatty acids. I suppose you could separate the butyric from the rest.
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Jome
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I belive butyric acid and the shorter carbon chain carboxylic acids that is formed can be separated from the others by mixing with water, the smaller
chains are water soluble. The others make stearine.
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12AX7
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Wasn't there somethnig about "fermenting" the butter?
Eh, depending on saturation, it could increase yield, I guess...
Tim
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Pyridinium
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| Quote: | Originally posted by 12AX7
Wasn't there somethnig about "fermenting" the butter?
Eh, depending on saturation, it could increase yield, I guess...
Tim |
You can make butyric acid by letting bacteria of the genus Clostridium go to work on carbohydrates in an anaerobic environment. Though you
have to be careful what species is used!!
Edit: found some info,
http://en.wikipedia.org/wiki/Butyric_acid
[Edited on 3-6-2005 by Pyridinium]
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quest
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| Quote: |
The first step saponifies the fats of butter, making soaps with them and freeing glycerin (glycerol).
The HCl should then produce the free fatty acids. I suppose you could separate the butyric from the rest.
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So after the first step I can separate the glycerin. (In this step, what do you think will be the ideal temp?)
And of what way have you thought to separate the butyric from the rest?
| Quote: |
You can make butyric acid by letting bacteria of the genus Clostridium
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And where can I find this kind of bacteria?
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Nerro
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If you put tabwater and chunks of potatoe in a jar and seal it airtight you can leave it for a few weeks in a warm dark spot. After that the potatoes
will have decomposed and the water will contain butyric acid. Some bacteria must have made it so if you take some of that water and put it with your
butter you might just have the right bacteria right there.
#261501 +(11351)- [X]
the \"bishop\" came to our church today
he was a fucken impostor
never once moved diagonally
courtesy of bash
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Pyridinium
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How about use a thick potato slurry in water you de-gassed under vacuum; put that in a sealed jar and let it putrefy / ferment, then after a few
weeks open it (gloves and respirator!!!!!!!!) filter the solids out, boil off the water, and fractionally distill the organic acids? Not sure offhand
what azeotropes form w/ butyric acid.
Another problem this might have is, I think certain bacteria can even break down butyric acid as their "fuel", maybe even anaerobic ones,
given enough time.
Clostridia occur in many places where there's organic matter but no air... compost heaps, etc. Problem there is, you are courting trouble
because you could get very sick from toxins they produce.
Yeah, I'd go with saponification and extraction from plain old butter. Maybe a few lb of it.
With the saponification method, I believe the glycerol will separate automatically from the chunks of soap, just like it does during soapmaking where
you can pick out the chunks and leave the glycerol behind.
Edit: I meant coagulate the soap into a mass, break it up, and get the chunks. I don't recall soap making isolated chunks by itself.
Nit-picking, but...
Also, butyric boils at 165.5 C, so once you got the water off, you could realistically distill off the butyric, provided I haven't overlooked
something.
[Edited on 4-6-2005 by Pyridinium]
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neutrino
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The acid would come off with the water, as per a standard steam distillation. You would need to fractionate the mix to get the acid like this.
A word of caution: Butyric acid is said to smell very bad. I’d do any work with it outside.
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Nerro
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Ow yes!
It really does smell, very, very! bad! UGH!
Be carefull. A few drops made our house smell of manure for days. Very unpleasant.
#261501 +(11351)- [X]
the \"bishop\" came to our church today
he was a fucken impostor
never once moved diagonally
courtesy of bash
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quest
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8 days ago I took the potato and crashed it through a grater, put it in a galss jat and full of water too the top.
Now I look at the jar in my warehouse and some gases starting to form, there is great pressure in the jar - can this make the jar to
"explode"?
[Edited on 15-6-2005 by quest]
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Blind Angel
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I wouldn't worry about that, the reaction isn't that fast and if the pressure build up too much the bacteria will simply die (i think). The
worst that could happen is that the lid pop a bit if it wasn't close thightly enough.
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quest
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Ok. the lid did pop a bit and it's looks Ok now, but another weird thing happened - I'm looking at the jar now (after 12 days)
and its look like 1/6-1/5 of the jar is full of some gas.......how can this happen? maybe there is some evaporation?
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Esplosivo
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Most bacteria generate gases when they metabolise chemicals as a source of energy. Therefore what you are observing are these gases produced during
the 'fermentation'. The pressure can build up after some time. Once I remember a bottle of wine sort of exploding due to an increased
internal pressure.
The best you could do is use one of those things they attach to the stoppers when making wine. I forgot what they're called. They are basically a
coiled plastic piping. One fills part of the curving section of the pipe with water. This allows gases evolved to go out of the fermenter but does not
allow other microbes to come in (ot at least it makes it more difficult for them to travel through a water layer).
I don't think pressure (at least not that generated by fermentation) could kill the bacteria/yeast.
Btw, does anyone know which bacteria is involved - you're mentioning bacteria right? I'm not refering to the yeast. Wikipedia mentions
Bacillus subtilis, but it is probably refering to the bacteria growing on putrefying cheese which is used as the innoculant.
Theory guides, experiment decides.
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quest
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The potato whay is working, it makes a very stinky substance. but it isn't butyric acid.
any whay, I looked for butyric acid formula and found this: CH3(CH2)2COOH
So I thought of just try to oxidize 1-n-butanol. I tryed with KMnO4 solution and it didn't worked (it smells just like the butanol I began with)
So am I wrong with the idea of oxidizing or just the KMnO4 isn't strong enogh oxidizer?
thanks all
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quest
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Jumping Jumping....sorry for this double post but I hope maybe some one can help me with my question
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hydrargirum
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If it has n-butanol you can oxidize it with Na2CrO7 + H2SO4,
another alternative is to oxidize the CH3CH2CH2CH2OH in excess with H2SO4 also in excess + Na2Cr2O7 and it will obtain Butyl-Butyrate ester of
pleasant fruity scent(pineapple), operating in cold(30-40ºC); the later saponification of ester gives to Butyric acid.
Ref. Organic Syntheses, Collective Volume 1, 138
n-Butyl n-Butyrate
www.orgsyn.org
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hydrargirum
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If it has n-butanol you can oxidize it with Na2Cr2O7 + H2SO4,
another alternative is to oxidize the CH3CH2CH2CH2OH in excess with H2SO4 also in excess + Na2Cr2O7 and it will obtain Butyl-Butyrate ester of
pleasant fruity scent(pineapple), operating in cold(30-40ºC); the later saponification of ester gives to Butyric acid.
Ref. Organic Syntheses, Collective Volume 1, 138
n-Butyl n-Butyrate
www.orgsyn.org
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quest
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First of all, will this synthesis work with K2Cr2O7 as well?
And what reaction do you mean buy "saponification"? mixing with NaOH solution?
Thanks
p.c.
Isn't it any straight way from n-butanol to n-butyric acid?
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CherrieBaby
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Theres a fair amount of information about "Butyric Fermentation" on the web. It seems to me that butyric fermentation is more complex than
just ensuring that you get the right organism fermenting anerobically. For instance, it's normal for the products of the fermentation (acid in
this case) to slow or stop the growth of the organism doing the fermenting. So one needs to work out how to remove the fermentation product; which is
done by adding chalk in the case of lactic fermentation. Here is Pasteur's paper on butyric fermentation:
Fermentation of Lactate of Lime, Pasteur
Below is the entry from The Carbon Compounds, Schorlemmer, 1874, p 298 (available from the library here):
Lactic Fermentation. - This kind of fermentation takes place by adding putrefying cheese to a dilute solution of glucoses,
cane-sugar, milk-sugar, or gum, and exposing it to a temperature of 25° to 35°, C6H12O6 = 2C3H6O3.
Acids prevent lactic fermentation, and therefore chalk or zinc oxide is added to keep the solution neutral. Together with lactic acid, a certain
quantity of mannite is always produced, and also a peculiar microscopic fungus consisting of smell globules.
Butyric Fermentation. - When the semi-solid mass of calcium lactate formed in lactic fermentation is exposed to a temperature above
36°, it redissolves, being converted into soluble calcium butyrate. At the same time hydrogen is evolved, and a living microscopic organism having a
cylindrical shape and a length of about making its 0.02 mm. appears in the liquid.
A patent and a another paper.
Continuous two stage, dual path anaerobic fermentation of butanol and other organic solvents using two different strains of bacteria. USP 5753474
http://www.freepatentsonline.com/5753474.html
Batch and fed-batch production of butyric acid by Clostridium butyricum ZJUCB, doi:10.1631/jzus.2005.B1076
http://www.zju.edu.cn/jzus/2005/B0511/B051105.pdf
[Edited on 31-10-2005 by CherrieBaby]
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BromicAcid
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How about chlorination of methyl ethyl ketone to give an alpha chlorinated compound followed by a Favorskii Rearragnement to give butanoate and
finally acidification to recover the free acid? Complicated but fun (Can't say what kind of yields you would get though).
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sparkgap
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Complicated, it is.  But if my memory serves me right, the rearrangement would
be the yield-limiting step of the synthesis, so it won't be recommendable.
/*offtopic -the pethidine synthesis I researched quite a while back also has this as the lowest yielding step, but then again that might also be due
to steric interactions... */
sparky (^_^)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
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