testimento
Hazard to Others
Posts: 351
Registered: 10-6-2013
Member Is Offline
Mood: No Mood
|
|
Toluene from benzene, styrene, gasoline?
I have become aware that the availability of toluene in my country is limited and I need to find an alternative supply route. Is it possible to
generate toluene from the listed items? The styrene should be first reduced to benzene, or are there other routes? Synthesizing toluene from benzene
from the synthesis I've discovered is PITA so is my information limited or are there any feasible ways?
From gasoline, I mean primarily by fractional distillation separation by using fractionating column up to 2 meters in height. I have found that
gasoline would contain 5-40% of toluene depending on the quality and producer of the fuel and it should, at least in theory, be possible to
fractionate pure enough toluene from it?
|
|
|
simba
Hazard to Others
Posts: 175
Registered: 20-5-2011
Member Is Offline
Mood: No Mood
|
|
It is possible, but the question is 'is it worth it?'. You can make toluene from benzene via friedel crafts, from styrene by oxidizing it to
benzaldehyde or benzoic acid and reducing it all the way into toluene. But none of these ways are an option just for getting toluene. My opinion is
that you should just pick another solvent that is available to you (unless you need toluene for synthesis), can you get xylene or DCM?
|
|
|
bbartlog
International Hazard
Posts: 1139
Registered: 27-8-2009
Location: Unmoored in time
Member Is Offline
Mood: No Mood
|
|
I don't know where you get 5-40% (except that apparently the maximum total aromatic fraction allowed by law in Chinese gasoline is 40%).
Couple minutes on Google turns up the following document: http://www.chem.agilent.com/Library/applications/5988-9261EN...
Look for table 3 on page 10. Apparently the toluene content varies widely depending on which gasoline you're talking about. I don't think you can
achieve full separation by mere fractional distillation, even with a good column; there will be alkanes with almost the same boiling point, in this
case iso-octanes would be very similar. Given their lower reactivity maybe this wouldn't matter for your purpose, though.
The less you bet, the more you lose when you win.
|
|
|
Nicodem
|
Thread Moved
10-6-2013 at 07:04 |
testimento
Hazard to Others
Posts: 351
Registered: 10-6-2013
Member Is Offline
Mood: No Mood
|
|
Thanks for your answers.
Is it possible to get benzene or toluene from styrene by any reliable way?
Few methods:
Styrene + ozone = benzaldehyde + oxidation = benzoic acid + calcium acetate = toluene
Styrene + alcl3 in reflux = benzene
|
|
|
Organikum
resurrected
Posts: 2329
Registered: 12-10-2002
Location: Europe
Member Is Offline
Mood: busy and in love
|
|
We have one comprehensive and several smaller threads covering the syntheisi of benzene. Just search only in the thread-headings for "benzene" and
voila'!
I can tell you this though, that benzene from benzoic acid and NaOH by dry distillation is a nice reaction with decent yields of very pure benzene,
and I wanted to recommend it to you anyways.
In almost all countries where toluene is taken from the public one can buy it without problems with a business license (no specific business
necessary). I recommend to get a license for a "janitor service" which includes cleaning up graffity and a thousand little things. The expense to get
the papers is usually very small and you can forever buy all solvents you ever wanted and more, even those you did not even know existed. DCM,
Toluene, GBL, chloroform and thats the harmless section.
Suppliers will happily send you their catalogues which make your eyes bleed.
/ORG
|
|
|
elementcollector1
International Hazard
Posts: 2684
Registered: 28-12-2011
Location: The Known Universe
Member Is Offline
Mood: Molten
|
|
I have no access to toluene where I live, and the method described above (benzaldehyde + oxidation = benzoic acid + calcium acetate = toluene), where
the beginning benzaldehyde is (possibly distilled? Depends on purity) from almond extract. But what oxidizing agent should I use? I have KMnO4,
NH4NO3, and a few others in reasonable quantities.
Elements Collected:52/87
Latest Acquired: Cl
Next in Line: Nd
|
|
|
simba
Hazard to Others
Posts: 175
Registered: 20-5-2011
Member Is Offline
Mood: No Mood
|
|
Its common to see people asking how to make benzaldehyde from toluene, but seeing people asking how to do the other way around sounds ridiculous to
me. Toluene from benzaldehyde? That's a crime. If you're really willing to do that, just give me your benzaldehyde instead, and I will be happy to
give all the toluene you need.
|
|
|
testimento
Hazard to Others
Posts: 351
Registered: 10-6-2013
Member Is Offline
Mood: No Mood
|
|
So, how would one turn styrene into toluene? Styrene is done by dehydrogenating ethylbenzene and toluene is methylbenzene, so would it be possible to
hydrogenate styrene again into ethylbenzene and metatheze its ethyl group with some other methyl group? Or is it necessary to reduce it all the way to
benzene and do the toluene with methyl chloride and aluminium chloride all way around?
PVC plastic produces benzene upon combustion. Could it be obtained by means of dry distillation, or is it necessary to induce burning? If so, I was
thinking of installing a small air pump into steel reactor and induce propane burner under it and condense the combustion gases.
|
|
|
adamsium
Hazard to Others
Posts: 180
Registered: 9-4-2012
Location: \ƚooɿ\
Member Is Offline
Mood: uprooting
|
|
Of course you can make toluene from styrene. If you want it as a reagent, it's going to be far more work (and expense) than just buying it.
You could oxidise the styrene to benzoic acid, convert to a benzoate and get benzene as discussed at length elsewhere on SM. You could then do a
Friedel-Crafts to get toluene (along with, likely, a mixture of xylenes and perhaps even further methylation of the ring).
If this is for anything other than the experience, it's absolutely pointless and uneconomical, and probably not really for a beginner. You'd need a
halomethane, which would probably mean messing around with thionyl chloride and other fun (and not-so-accessible-to-most) things. Reducing benzoic
acid or benzaldehyde directly to toluene would, likewise, not really be a project to be undertaken lightly (or at all, really) by a beginner in a home
lab and would also require reagents that are likely much more difficult to procure than toluene.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
