[tomscott]

Just out of curiosity is there a way to make soy wax without using hydrogen or the process of hydrogenation?

[Arkcon]

Well, since we like to do Socratic learning around here:  Can you start by telling us what the hydrogenation of fats does chemically, and who does that affect the physical properties?

[tomscott]

Yeah... About that... I'm not really a chemist or have any type of chemistry background so I'm a little lacking on the actual process of hydrogenation.

I know the basics I guess.  The passing of hydrogen through the oil to bond hydrogen to the atoms within the oil using a nickel catalyst mostly and high heat and pressure.

Beyond that I'm no good.

[fledarmus]

Hmmm - may be hard to give an answer that you will be able to understand. How far do you want to go into this?

Your question is sort of like saying "Is there a way to make a Corvette without going through a Corvette assembly line?" If you make all the appropriate parts and put them together yourself, is it still a Corvette? All you've made is a copy. The very simple answer to your question is no there isn't a way to make soy wax without hydrogenation, because the definition of soy wax is soy oil that has been partially hydrogenated to the extent that it is a waxy solid instead of an oil. However, you could try to put together a copy of soy wax by collecting all of the individual components and mixing them together...

There is a table on this page http://www.scientificpsychic.com/fitness/fattyacids1.html that shows the major components of soybean oil. Vegetable oils are mixtures of glycerides, which are glycerol molecules with one, two, or three long-chain fatty acids attached (mono-, di-, or tri-glycerides). The only difference between a vegetable oil and a vegetable wax is how well the glycerides can pack together. If they fit together very well, they can form a semi-solid wax, and the better they fit, the higher the melting point of the wax.

Unsaturated fatty acids have double bonds in the fatty acid chain (monounsaturated acids have one double bond, polyunsaturated acids have more than one). Saturated fatty acids don't have any double bonds. If you imagine the saturated fatty acids lying together like straight sticks which can lie very close together, unsaturated fatty acids have bends in the sticks at every double bond. While a pile of straight sticks fit very tightly together and can be easily moved as a single group, a pile of bent sticks tends to make an ungainly mess. This is the basic difference between a wax and an oil - the fatty acids in the wax lie close together in an ordered structure and the material is a solid, while the fatty acids in the wax get all bent around each other, there is little order in the structure, and the material is a liquid.

Hydrogenation is the process of added hydrogens across double bonds to make saturated fatty acids out of unsaturated fatty acids. The more you hydrogenate the oil, the fewer double bonds there are, the more "straight sticks" there will be in the mixture, and the more likely that you will have a nice ordered waxy structure.

[tomscott]

Yes, basically I'm trying to make the Vette without going through the line.  They actually happen to be produced about 30miles from where I'm sitting...  I just figured there had to be another way past hydrogenation.  I just can't imagine that hydrogenation is that only way of solidify the oil.  Would there be any chemicals that would accomplish this?  Kind of like in the production of soap?

Thanks!

[fledarmus]

Well, you could make soap out of it    When you add a strong base to these glycerides, you break the bonds from the fatty acid to the glycerol molecules and end up with soaps. But this probably wouldn't be a solid soap either, because again, there are too many kinks in the fatty acid chains for them to pack well. Lard is one such "oil" that is much more saturated and was usually used to make soap back in the day.

But basically, you have to do something to get the kinks out of the chains to get a solid. There are lots of other reactions that can be carried out on the double bonds besides hydrogenations (see http://en.wikipedia.org/wiki/Alkenes), but you end up with other things on your fatty acids besides just hydrogen. Some of them might make better solids - for example, adding things like hydroxy groups would allow for hydrogen bonding between chains, holding them tighter together - but it wouldn't be soy wax. The other thing that you could do would be to simply remove any of the kinked chains, leaving only the saturated ones. That involves some very tricky separations, and you end up with far less wax than if you simply converted the kinked chains into saturated ones.

[tomscott]

Just out of pure curiosity... How dangerous is hydrogenation?