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kazaa81
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Butane infos. required
Hallo to all,
I've got some liquid butane (C4H10) and I was thinking about what can I do with this (except extractions)....like liquid or solid derivates. Can
anyone post butane common reactions and/or interesting reactions to do with it?
Thanks at all for help!
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BromicAcid
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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 CS<sub>2</sub> and H<sub>2</sub>S 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.
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kazaa81
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Thanks a lot BromicAcid!
Yes, the most ease reaction with butane would be (except burning it....but chemical reaction too :-)) chlorinate it.
I've found very simple to work on gases with improvised equipment as show on a site.....glass and latex tubing and various syringes. With butane
chlorination I'll get the two isomers 1-chlorobutane (also called butyl chloride, sounds nice and also liquid) and 2-chlorobutane.
Where i am now external temp is about 38°C and a lot of sun.....
As soon I'll chlorinate butane (adding to C4H10 chlorine obtained from NaClO + HCl) i will inform you, if i could.
If anyone has other ideas on butyl chloride experiments, too, please post them.
Thanks another time, Bromic!
and thanks at all
[edit- site url showing simple gas handling techniques found... http://mattson.creighton.edu/Microscale_Gas_Chemistry.html ]
[Edited on 13-8-2005 by kazaa81]
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kazaa81
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ok, i've assembled the apparatus to try add chlorine to butane via photochemical reaction, giving chlorobutanes (also butyl chloride,nice
liquid!).....
what does I obtain if I pump butane in conc. (90%) H2SO4?
Any information welcomed
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trilobite
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Don't forget gas phase nitration. Gives you different nitroalkanes, pioneered by Henry B. Hass and coworkers.
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garage chemist
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Butane doesn't react with 90% H2SO4, so this can be used to dry it (not necessary though, as the butane from the can of lighter refill is already
dry).
The chlorine should be dried before reaction, just add some H2SO4 to the syringe and shake it around.
Oh, and don't expect more than a little drop of butyl chloride from butane + Cl2 when not using more than a syringeful each.
The reaction also needs to be initiated in some way, like the reaction with oxygen, or else it will proceed very slow.
An idea would be to fill a big flask with chlorine and then submerse a glass pipe with a burning butane stream at the end into the cylinder. The
butane will "burn" in the chlorine and the butyl chloride will condense on the walls.
Fill the flask with water to collect your butyl chloride, it is immiscible with water and more dense, that means you will get a "blob" of
butyl chloride under the water.
[Edited on 15-8-2005 by garage chemist]
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kazaa81
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I've tried to react in a small syringe (10ml) chlorine and butane and probably get the little drop you sayed about, garegechemist.
Even if not tryed, your idead of burning butane in chlorine sounds good to me....
I've got a US patent (6,570,045) where it is wrote which low-boiling point hydrocarbons (butane too) can be solidifyied with water and a metallic
aliphatic carboxylic salt dissolved in (water). Now i'm saponifing olive oil with NaOH to get sodium oleate.....can anyone post his experience on
this and/or try it too? Also, from which carboxylic salts dissolved in water and the electrolized (Kolbe reaction) can butane (or others hydrocarbons)
be obtained?
Thanks at all for help!
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12AX7
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You'll have to compress that butane pretty well, lest it freeze the H2SO4. 
Tim
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kazaa81
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Also would butyl chloride be suitable to make triisobutylaluminium (TIBA or TIBAL)?
That pyrophoric material would be funny!
Any ideas about arguments previously writed welcomed!
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kazaa81
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Anyone interested in garagechemist's idea of producing butyl chloride?
Unfortunately, i can't try it now...
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kazaa81
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butane cracking.....
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stygian
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I once had the idea to use chlorine gas as an oxidizer for one of those little butane soldering torches (probably wouldn't be hard to set up) and
condense/distill whatever products may be formed (all sorts of chlorine substituted butanes, of course.) Never got around to doing it of course, but
it sounded interesting.
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kazaa81
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Working without high pressures, a butyl chloride preparation from butane and chlorine can be like a flask heated to 40°C in presence of UV light with
2 tubes inserted in it: from one exits butane and from the other chlorine, which inside the flask condense buthyl chloride?
Please post any idea or comment, also texts!
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The_Davster
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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)
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kazaa81
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Don't hate chlorine that much, rogue chemist! Yes, it can brought you to death but it also provided the synthesis of chloroform, which
anestethise people and don't let them feel doctors who do a large cut etc......but you can hate it, if you want!
Rogue, can you tell me more extesively what is the addition of Cl2 in a flask via water displacement?
Also, why is needed to get butane burn in chlorine? If i use a butane can, it isn't that safe because flame can be asphired in the can
and....boom!
Thank you rogue for partecipating in the butyl chloride experiments (use some good cream for burn treatments)!
Any idea/experience welcomed!
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The_Davster
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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]
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kazaa81
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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]
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The_Davster
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After the flask was full of chlorine it is carefully pulled out quickly from the beaker, righted, and stoppered until I got the butane flame going.
So yes, you must take the flask out of water.
Anyway, if I have time I will try this again within the next few days.
EDIT:
I tried it again, and I managed to burn 60mL of butane in ~250mL of chlorine. By the end all chlorine colour had left the flask. However near the
end of burning the butane, the inside bottom of the flask caught fire, and upon chiling the flask in the freezer and adding water no layer of
chlorobutane was seen. So next time I will keep the flame a bit higher up in the flask to prevent it from catching fire.
[Edited on 11-9-2005 by rogue chemist]
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kazaa81
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Thank you rogue chemist!
I'm going to obtain an other flask, bigger than the ones i have.....also now I deeply understand what you've wrote.
Still don't know why burning butane instead of just adding it to Cl2...
Strange which any butyl chloride drop haven't formed...
Any idea/experience wellcomed!
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The_Davster
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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.
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stygian
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My idea of using a soldering torch comes from the fact that (the one i had) has a few places where it would be convenient to introduct chlorine, a
platinum honeycomb catalyst, and a way to regulate to flow of butane to achieve whatever ratio you want. It would also be small enough to attach
directly to some sort of condenser, most likely metal. Of course, this is just an idea i had. If I had money, and a safe remote location, I might do
something practical someday.
Just my $.02
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S.C. Wack
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HALOGENATION OF PARAFFIN HYDROCARBONS
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The_Davster
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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 .
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kazaa81
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Thanks at all for helps!
Don't worry rogue chemist, the commercial butane cans are almost pure n-butane, with traces (maybe) of iso-butane.
I, being in Italy, have much sun to deal with, but also prefer your method of burning butane in Cl2.
The reason you wrote about "disappearing" of butyl chloride seem possible to me, so one can burn butane in Cl2 (in a inverted flask in
water) then removing butane steam and reverting the flask, sealing it and wait a little.
Any idea/experience wellcomed!
[Edited on 12-9-2005 by kazaa81]
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Oxydro
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Kazaa81, I beg to differ about the isobutane content of commercial butane.
Ronson's butane fuel is 100% isobutane, according to the MSDS.
I don't know of other brands, but I suspect that they are similar.
"Our interest's on the dangerous side of things" -- Browning
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