Butane infos. required

As with most saturated straight chain hydrocarbons there are not a lot of interesting reactions. Chlorination, bromination, and of course fluorination () are possibilities. The latter two requiring the use of UV light and slightly elevated temperatures (~35C). Oxidation unless it is the reaction of the butane with atmospheric oxygen and a spark will be difficult to get aldehydes, alcohols, or ketones out of it (then again I don't know much about oxidation of alkanes to get these in-between oxidation products).

Combustion with sulfur at 900C gives CS₂ and H₂S and there are always super acids but they give a whole variety of compounds, not really that useful on a short chain like butane anyway.

If you decide to chlorinate it you would have to separate the products by fractioning likely and once done you could have your fun with the chlorinated derivatives as you like, i.e. butyl lithium from reaction with lithium metal, and other little neat things.

In some reactions you can of course use a hydrocarbon as the inert atmosphere, butane having a low boiling point is a decent choice for this.

You'll have to compress that butane pretty well, lest it freeze the H2SO4.

Tim

Ah....I hate chlorine.

I was bored tonight so I attempted the burning of butane in a Cl2 atmosphere. I filled a 250mL flask with chlorine via water displacement method and filled a 70mL syringe with butane. I attached the syringe to a piece of glass tubing drawn to a point. The butane was slowly pushed out of the syringe and the butane coming out of the point was carefully lit with a tea candle I then moved this flame into the open flask of chlorine. The flame became a deeper orange and large ammounts of soot were given off. My hand was burned as I was holding the glass tube only 4" above the sooty flame. I could not keep my hand there any longer so I discontinued adding butane(only 20mL added). I added water to the flask and vapours flowed out the top, unfortunatly right in front of my nose, the vapour smelled a bit organic with a lot of seemingly HCl and Cl2 gas in there. I did not notice any liquid drop in the bottom of the flask, likely because I did not allow the flask to cool before adding water, so any chlorobutanes in there was forced out the top as a vapour. I think some was formed, as I definatly smelled something that was not Cl2 or HCl in the vapours.

Did I mention I hate chlorine? ( I did this indoors(yeah I know its stupid) as it is incredibly windy outside, too windy to keep a flame lit on the tea candle I was using to ignite the butane)

The water displacement method for filling vessels with gas.

The flask I filled with chlorine was completly filled with water and stoppered. It was then inverted in a 600mL beaker half filled with water and the stopper carefully removed. A bent glass tube is then inserted under the inverted flask and gas is bubbled in until the flask is full. The second pic in the link below shows this on testtube scale.
http://www.tiscali.co.uk/reference/encyclopaedia/hutchinson/...

EDIT: I also recoment using a wider glass tube(2mm ID should be good) for combustion of the butane, as with a smaller ID like I used there were many problems with pushing the syringe too fast causing the butane flame to go out.

PS: The burn was not that bad

[Edited on 11-9-2005 by rogue chemist]

Thank youy again, rogue chemist!
Nice to hear which your burn wasn't serious!

I heard about this method but don't know exactly its english name...so the Cl2 gas is trapped in the flask and also pressurised a little (by your holding and flask weight).
When passing butane (ignited with a flame), i must take the flask out of water or not? If i don't, won't the butyl chloride go in the beaker?

Thank you for posting experience/ideas!

Any improvement/other idea?

[Edited on 11-9-2005 by kazaa81]

You burn the butane in the chlorine because this reaction only proceeds at elevated temperatures. If just chlorine and butane were mixed at room temp, nothing would happen. I imagaine however, that a spark gap in a sealed Cl2/butane atmosphere would give some results as Bromic suggested. I would try UV, but that is too much of a hassle for me as the Canadain winter is beginning to set in so I cannot just leave a sealed flask of butane and chlorine outside for days to see what happens.

Another idea is to only burn the butane in the chlorine atmosphere until the flame is no longer orange and sooty, and then remove the flame, as after this point I believe there runs the risk of setting the chlorobutane on fire, as as the chlorine is used atmospheric oxygen will begin to fill the flask. This is a fun experiment though, nice cheap reactants.

Next experiment I may do in my 2L erlenmeyer.

Great referance, S.C. Wack .

So perhaps the mixing of butane with chlorine and allowing to sit in the sunlight will still work. However, is commercial butane n-butane or isobutane? Isobutane according to that file has a rather explosive reaction with chlorine. Hopefully isobutane only does this when pure. We shall soon find out .