MethylBenzene (Toluene)

[YT2095]

the problem occured upon the decanting, as soon as the liquid hit the cooler receptical sulpher started forming cloud like paterns in there like egg yolk half cooked.

I did get some nice needles growing in there over time, about 4mm long x 1 mm wide in clusters.

my sulpher Was in excess though, so perhaps my toluene was too saturated.

I`ll give the product a dilute HCl wash and rinse with deionised water and then allow to dry 100%, and re-perform this again, but without decanting, I have suitable insulation that should allow it to cool VERY slowly to make larger crystal specemins, and keep a few of the smaller ones back for under the microscope.

[Pleiades]

After trying this on a small scale I’d like to do larger batches, before I do I’d like to know which of the following heating methods is unsafe:

 

1. Immersion element in direct contact with toluene.
   
2. Immersion element heating water in a double boiler/ water bath
   
3. Electric stove type element (hot plate) heating a pot of toluene.
   

[hybrid04]

Yeah -no2 groups strong deactivate aromatic rings, which would make the further subsitutions increasingly more difficult. nearly impossible to tri substitute that way. Would take some other techniques to do so

[YT2095]

methods 1 2 and 3 all have their dangers involved, the trick is to lower the possibility and to have measures in place in Case things go wrong, the real dangers are the Fumes with toluene, not only are they very flamable but they can also render you unconscious.

 

if you`ve got an old saucepan you don`t use, that would be ideal to contain your vessel of toluene, that way if it did catch fire, it`s contained in a metal pan and you have a long handle on it to remove it if the vessel cracks and lots of fumes escape.

do it outside sheltered from the wind, and will be fine, but never leave it unattended, it goes to Boiling quite quickly, and then you turn the power off.

if you can, make a mark on the bottle at the liquid level, and watch this to see if it goes up just before it boils

[Pleiades]

I’m defiantly doing it outside and I have every intention of wearing a half-face organic vapor respirator; I tend to get a headache from fumes even at fairly low concentrations. I don’t plan on spilling boiling toluene on my self, but I’ll probably wear chemical resistant gloves anyway.

 

Now that I’m thinking about it I should also have a bucket of sand standing by.

 

The boiling point of toluene is 110C, heating the toluene with boiling water like woelen did wouldn’t allow the toluene to boil, but heating it without water like YT did would allow it to boil, perhaps it expands the most between 100C and 110C. I’ll be sure to use a thermometer when I do it. On a side note, wouldn’t adding more sulphur to the solution raise the boiling point, allowing you dissolve more sulphur?

[YT2095]

good question, it sound reasonable, but I added mine while it was still cold, I didn`t want to be too close to it afterwards anymore than necesary, which was to decant the yellow hot liquid into another vessel. to be honest I`m not 100% sure why the sulpher dissolves in it at all

[jdurg]

Take a look at the structure of sulfur. Sulfur is a puckered ring of 8 sulfur atoms which is really a very non-polar substance. Toluene is very non-polar so the whole "like dissolves like" theory kicks in.

[YT2095]

could it be the breaking appart of the 8 ring that accounts for the volume increase upon heating?

I think I`ll have to try the same again with straight toluene.

[YT2095]

*BUMP*

rather than make a new thread etc...

 

I`ve been experimenting again with said chemical, and found an interesting reaction when mixed with solid NaOH, it goes a grey green color to start with, then after some minutes the color starts to turn a Redish/Orange.

I`ve no idea what hell it`s doing or making just yet, but I Was hoping that some Sodium would attatch to the benzene ring that can displace later with perhaps an Amine group with addition of Ammonium Chloride.

 

it just seemed a reasonable idea as a way to get a foothold onto the benzene ring.

[YT2095]

24 hours later, the liquid has stabilised at the red/orange color, but is now quite viscous and there seems to be Gel like bits in it also?

 

it smells the same as toluene and also burns the same but leaves a water soluble white powder solid behind.

 

any idea what this stuff is?

can you Make soap with toluene?

[woelen]

Did you pour the toluene over the NaOH, without adding extra water? It seems that there are impurities in the toluene which react with the NaOH. I know of no reaction between NaOH and toluene. I will try with my toluene this evening and report on that. I have "real" toluene, sold as such, and not the stuff from the hardware store. Let's see if this can be reproduced.

[YT2095]

it Can be reproduced with Impure NaOH, I tried pure KOH and no reaction of significance took place.

beyond a slight temp rise of 5c (airborne moisture).

 

my NaOH has the contaminant, I suspect perhaps an Iron salt, it would go a long way to explain the Green and then Orange color change.

 

although disappointing, I`m pleased that I now Know about this

 

 

edit: if this is any use, I just dumped it out but before I did I added water, when it got past the gel layer, a heating took place as it got to the NaOH prills, after dissolving, all the color then transfered to the Aquios layer and left the toluene alone again, the same original color.

the addition of water to Just a the toluene I decanted off also did the same.

 

seems I need a better NaOH source!

[woelen]

I also did the experiment. I added NaOH to toluene, and the solid did not react at all. After 3 hours, there still is colorless toluene and on the bottom there are white granules of NaOH.

 

Next, I added a single drop of water and heated the liquid to 70 C. Now, the NaOH liquefies with the water, and a thin sirupy layer is formed at the bottom. Strong shaking causes formation of small droplets, which quickly settle at the bottom again. The toluene, however, remains colorless and perfectly clear.

 

What sodium hydroxide do you use? I hardly can believe that it is the NaOH which causes this reaction. Are your prills of NaOH white? If so, then they certainly do not contain iron. White NaOH is not very pure, but the only common contaminants are NaCl (remains from the electrolysis production process), Na2CO3, and water. Commercial NaOH may contain as much as 5% of impurities, mostly NaOH and water, and traces of Na2CO3. Other impurities I hardly can imagine, unless added on purpose (such as flakes of Al in some brands of drain opener).

 

Very pure NaOH looks like glass with a matte outside of the granules.

 

So, if your NaOH is white, then I really suspect the toluene is not very pure. The reason that no reaction occurred with your KOH may be because of lower water content, making it totally insoluble. Add a tiny amount of water to your KOH/toluene mix and see what happens. If in that case, you again get orange color, then it really is the toluene, that has impurities.

[YT2095]

ok dokes, I`ll do that now

 

edit, Ok done, strong heating at 1`st as the water hit the bottom to the KOH, after a few seconds it disolved then when stired it went back to cold again and the Toluene is now a white color and the Aq layer at the bottom is clear with a VERY slight yellowish tinge, only something that shows up with a white paper test.

 

yes my NaOH prills are Briliant White, they also leave no no traces when dissolved, the soln goes clear 100%.

 

kind of leaves me wondering what exactly ELSE I`ve been Nitrating! (Woelen, you know what I`m on about here).

[woelen]

YT, could you try the KOH-toluene mix again? Add a very small amount of water, such that the KOH is just wetted (e.g. with some damp cotton wadding, you touch the KOH and then add it to the toluene). Try what happens if you allow this to stand for a few hours.

 

At the same time, try this with your NaOH and let this stand as well. If there is a significant difference, then there must indeed be something in the NaOH. Now, it might also be some contamination from your test tube, the rubber/cork stopper, or glass container in which you do the experiment. At least you should be able to track down, which chemical or other thing causes the orange color.

[YT2095]

ok Done on both, the KOH Hissed when I added the droplet, the NaOH was more sedate

Both got Very Hot though. I used 2 brand new never used test tubes direct out the original box they came in.

 

the Toluene was then added to each, the KOH did the same as before, a clear and Very distinct Toluene and AQ layer with the Toluene turning White, no color change yet, the AQ layer is crystal clear.

 

the NaOH was Different, the layers are Very hard to define and both are turbid white also, the AQ layer most turbid of the 2, there is No color change of greens or orange.

 

both still have crystals undissolved though.

 

I guess we just wait now

[JHAQ]

Because of the attackable methyl group ( assists in oxidative metabolisability ), toluene is nowhere near as toxic as benzene .

[jdurg]

You know, something woelen said got me thinking. You should be fairly careful with this mixture you have YT. A method of producing NaOH is using a mercury electrode. The green color you mentioned makes me think that perhaps there is some mercury ion contamination in the NaOH you were using? Organic mercury compounds are really nasty things that you want to try and avoid. Chances are it ISN'T a mercury contamination, but better safet than sorry.

[YT2095]

I tried to reproduce my original results again with brand new out-the-box test tubes, and although the NaOH did form that Gel like substance, it stayed in the Aq layer and there was no color change, the KOH was even less of a spectacle.

the only thing I can think of is that it`s a metal contamination from the test tube(s), I had been soaking Wool peices in various metal salts about a week or so prior to this in them, and Prussian blue, when left to stand is quite hard to remove entirely.

 

interesting point about the mercury though, although since the main use for caustic soda is unbloking drains and oven cleaning, I should imagine they make every effort to avoid mercury traces in it, some even use it for soap making.

[aamera]

convert toluene into nitro toluene then reduce this nitro toluene with aluminium in basic media (NaOH).U will obtain beautiful orange coloured crystals of azo compounds

[YT2095]

thnx

 

I have a small sample of 2,4,6 Trinitromethylbenzene here, and also the same as a Phenol.

 

there may be a problem as Either of these in a Basic soln become Very unstable!

 

so when you say Nitro toluene, what do you mean?

mono, di, or Tri?

[insane_alien]

also ortho, para or meta with the methyl, they would have different properties

[YT2095]

I don`t think that counts with only the functional group and the O2N, it`s just the position number them AFAIK.

it comes into play when 2 groups are the same tho, in a Di structure.

p-Di xxxx Phenol or Benzene.

 

I could be wrong, but it`s rare I hear it used with different groups.

[insane_alien]

well, according to my chem structure lecturer last year it could have a "huge" tm effect. never mentioned anything more than that unfortunately so it could be anywhere from a slight shade difference to decreased reactivity

[YT2095]

it Does have big difference

 

think Catechol, hydroquinone and resorcinol, all chemicaly identical appart from the OH position, and they don`t even look or smell the same either

 

my query was about the Naming convention rather than the properties.