Sciencemadness Discussion Board

Any way to make this patent procedure work?

palladium8 - 27-9-2014 at 18:58

Free-radical synthesis of allylbenzene from toluene and acetylene

US3209043
Quote:
Example I
A run was carried out in which toluene was contacted with acetylene in the presence of di-tert-butyl peroxide* to form allylbenzene.

In a 1-liter Magne Dash stirred autoclave, 500 ml (430 grams, 4.67 mole) of toluene and 100 ml (78 grams, 0.53 mole) of di-t-butyl peroxide were heated 28 hours at 257° F. using a pressure of 100 psi of acetylene. Nitrogen was added to a total pressure of 250 psig.

The recovered product (517 grams) was washed with water. Some pentane was added at this point to aid in the phase separation. The organic phase was then dried over anhydrous potassium carbonate, 25 ml. of n-decane was added, and the product was distilled through a Minnical column. Eighteen grams of distillate was collected in the range 302° to 349° F. Analysis by gas chromatography indicated that this distillate contained 5.6 grams of allylbenzene. Eighty-nine grams of heavy residue remained after distilling most of the allylbenzene and added n-decane. An infrared spectrum of the center cut of the distillate was identical with that of known allylbenzene.


* Could easily be substituted for benzoyl peroxide.

Of course I wouldn't want to use 100 psi of acetylene, so maybe just add a little toluene to a big vessel (~3 L), fill with acetylene to 15 psi, and use a paint shaker to shake it for a couple days. Benzoyl peroxide would be used as the radical initiator. Nichrome wire will be used for heating to 150 C. But would it work? Any tips? :)

Note: I already know there are "easier" methods of producing allylbenzene such as Freidel-Crafts or even ones that can directly condense allyl alcohol and benzene, but I'm interested in the potential of this procedure specifically.

aga - 29-9-2014 at 13:01

Patents are a Legal mechanism to grab cash from something that nobody else got a Patent on already, and wasn't already common knowledge.

They don't actually have to Work to be granted a Patent.

This one might work, might not, like all of 'em.

Best thing would be to ask the Patent Holder if it actually works, and if so, how.