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Topic: Add ethane to a double bond?  (Read 2649 times)

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Offline Enthalpy

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Add ethane to a double bond?
« on: January 20, 2011, 12:41:31 PM »
Again an ignorant's question, sorry for that...

Myrcene obtained industrially by pyrolysis of dirt-cheap turpentine can be hydrogenated efficiently, as claimed by
http://www.rsc.org/publishing/journals/GC/article.asp?doi=b916017p
into 2,6-dimethyloctane which is a good rocket fuel, or rocket propellant.
Pictures of both molecules: http://saposjoint.net/Forum/viewtopic.php?f=66&t=2609#p30260

But I'd prefer to add ethane instead of hydrogen, at all of myrcene's three double bonds.
This would raise the boiling point, hence the flash point, improving safety, while the even more ramified alkane keeps a very low melting point.

Is this cheap to do in hundreds or thousands of tons?

Does it involve adding C2H5Cl at the double bonds, then react the chlorinated product with hydrogen? Or is there a more direct way, like for hydrogenation?

Which side of the double bonds do you expect the ethyls to choose? A random mix of all isomers would improve the melting point.

Or is all this unnecessary, because a cheap ramified alkane around C16H34 already exists?

Thank you!
Marc Schaefer, aka Enthalpy

Offline Enthalpy

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Re: Add ethane to a double bond?
« Reply #1 on: January 25, 2011, 10:16:04 PM »
Or could it possibly be that...

That ethane, propane, butane, saved from the flare stack, would make all the ramified alkanes I need, just using a bit of dirt-cheap chlorine maybe, and a moderate amount of heat?

And that as a consequence, starting from turpentine would just be a bizarre complication?

Man, I'm no chemist and have no plan to be one, so giving me such an answer is just fine!
Could you confirm?

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