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Convert a bar of soap into fatty acids

Convert a bar of soap into fatty acids
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  • fam_from_ivory_soap-title_image.jpg
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In this 'ible I will demonstrate unto the Instructables community, and anyone else in the World who cares to read this, how I converted a bar of Ivory(r) soap, and a few hundred milliliters of The Works(r) brand toilet bowl cleaner, into a solid, white, waxy mass, that I believe to be a mixture of fatty acids. 

I think this project is interesting, and weird, and I think it definitely qualifies as an "unusual use" for "everyday things" found in a typical bathroom, so I am entering it in the "Unusual Uses: Bathroom Challenge".
http://www.instructables.com/contest/uubathroom/

If you like this 'ible, and you are viewing it while the U-U-Bathroom contest is still active, please vote for it.

By the way, certain salient features of this ible, and this ible's very existence, were directly inspired by the U-U-Bathroom contest.  
What I mean by that is, I probably would not have thought to try this at all, if it were not for the U-U-Bathroom contest.  What I mean by "salient features" is the fact that the starting materials are:  Ivory(r) soap,  the hydrochloric-acid (HCl) based The Works(r) brand toilet bowl cleaner, and water.  Each of these being typical bathroom items. These are not the only starting materials that could be used to synthesize a fatty acid mixture (FAM), and maybe these are not the best choice of materials either. 

I got interested in FAM by reading this tutorial
http://opensourcenano.net/projects/project1/
which shows how to make fatty-acid coated magnetite nanoparticles, and I found it while while searching for recipes on how to make ferrofluid.  The FAM made via the recipe linked above is made using ingredients you might find in your kitchen, like: olive oil, vinegar, and sodium hydroxide (NaOH) drain cleaner.  A PDF copy of their paper is attached below.

In fact a kitchen themed method for making FAM is a better method in many ways.  Vinegar is less acidic and thus safer to work with than HCl based toilet cleaner.  That's the main advantage. Also the raw ingredients should be cheaper, given that they are more raw, i.e less processed.  You could probably find oil, vinegar, and lye in a pre-industrial (or even a post-industrial) society.  Also the kitchen method produces a valuable by-product: glycerol.  These more natural ingredients probably smell better too.

However for the purposes of this instructable, I am going to assume that I'm living in some sort of dystopian over-industrialized consumer society, where the only available ingredients are ones sold as products intended to be used for something else.  Another interesting feature of this hypothetical dystopian consumer society is that not only does the television/government tell you what to buy, but they also dictate how you must use these products once you get them home.  In many cases the appropriate use for a given consumer product is to literally flush it down the toilet.  Then go out and buy some more! Ha!

Which leads me to the best part:  This instructable may be a violation of Federal Law (in the Former US)  provided it constitutes a use of The Works(r) brand toilet bowl cleaner in a manner inconsistent with its labeling.  A screenshot of http://www.theworkscleans.com/toiletcleaner.html is attached as a picture, the 4th in the stack, complete with misspellings. 
;-)

Seriously though kids, the most dangerous part of this 'ible is probably not the danger of running afoul of  the guys who wear jackets with three letters printed on the back.   Most of the danger in this 'ible comes from the fact that you're working with hydrochloric acid.  The Works(r) brand toilet bowl cleaner is 20% HCl by weight, or about 6 mol HCl per liter.  It's kinda nasty stuff.  You definitely want to wear eye protection.  And gloves too.   You should also wear gloves and eye protection in the event of you using that Works(r) stuff to clean stubborn lime scale deposits in your toilet.   And that could happen too. You'll have some left over.   The recipe presented in this 'ible only uses like one quarter, 200 ml of a 800 ml ,bottle of The Works(r), per 127 gram bar of Ivory(r) soap.

Final note of this intro: I am still kind of a noob on the subject of chemistry, especially with respect to lab work. My knowledge is incomplete, and my garage is not a professional laboratory, yet I believe that what I'm doing in this 'ible is reasonably safe. Some persons reading this 'ible may disagree with my assessment of risk, and I love reading comments that say what I am doing is unsafe, immoral, illegal, or that I'm just plain doing it wrong. So keep that criticism coming!

 
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Step 1Background: Triglycerides - how fatty acids occur in nature in plant and animal tissue

Background: Triglycerides - how fatty acids occur in nature in plant and animal tissue

Natural oils and fats, a.k.a triglycerides, are esters of glycerol (which has 3 OH groups)  and various fatty acids.  Soaps are made by hydrolyzing(reacting via water) natural oils with alkaline (e.g Na+, K+) hydroxides.  For example 3 mols of  NaOH, will react with one mol of a triglyceride to produce one glycerol and three soaps.   For the triglyceride stearin, this reaction is:


C3H5(C18H35O2)3 + 3 NaOH → C3H5(OH)3 + 3 NaC17H35COO


stearin +3 NaOH  → 1 glycerol + 3 sodium stearate

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8 comments
Aug 30, 2011. 1:22 PMLefrançois says:
essayer au micro-ondes vu sur youtube
Jun 11, 2011. 4:56 PMcloudifornia says:
I don 't care what it is. If's it is a VOFL, I'm all for it! ;-O)
Jun 8, 2011. 10:23 PMhewhoiswright says:
I'm sorry to break it to you, but you definitely do not have fatty acids. Soap is indeed made from fatty acids and sodium hydroxide. this is a process called saponification, which is irreversible. This differs from a simple acid base substitution, as it only works with carboxylic acids (organic acids) and strong bases.
May 1, 2011. 12:45 PMArano says:
The melting point of fatty acids is mostly dependent to their molecular weight and structure(heavier/longer and straighter->higher meltingpoint). Same goes for the triglycerides. If you are interested look up van der waals force. The oleic acid is a little lighter (well less than 1% which shouldn't make much difference) but it has a doublebond in the middle which bents it which makes the difference in the melting point as it lowers the van der waals force between two molecules.
May 3, 2011. 1:30 PMArano says:
The weight itself has little effect on the meltingpoint, it's more like a good guess because in most cases the forces between the molecules tend to be stronger for heavier molecules. the length and the structure make the difference. the 'straightnes' also only aplies for noncyclic molecules. to show what i mean: compare isooctane, n-hexane and cyclohexane. isooctane is about 1.3 times as heavie as n-hexane; cyclohexane is a loop. the meltingpoints are about: isooctane -107°C, n-hexane -95°C, cyclohexane 7°C. if 2 molecules are hard to compare it's hard to guess which has the higher meltingpoint.
May 2, 2011. 3:35 AMcoolkids says:
you could use this to burn lamps

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Author:Jack A Lopez
I've built some weird stuff over the years, but most of that stuff has remained unseen by the world outside of me and a few friends. But then one day, one of these friends, he says to me, "Hey Jack, ...
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