[mreff555]

I ended up getting the ugliest spectroscopy I had ever seen the other day, after trying to Nitrate some Methylbenzene with a 1:1 mixture of Nitric acid and Sulfuric acid. There was some particles I was unable to filter and ended up leaving them because I wasn't sure what to do with them. They were big yellow flakes that percipitated when i (per instruction) poured the solution over ice. Polar solvents seem to have not effect on it. What is it?

[azmanam]

TNT?  carefully close your hood sash and run?  (only half joking)

[alexjaco]

I ended up getting the ugliest spectroscopy I had ever seen the other day, after trying to Nitrate some Methylbenzene with a 1:1 mixture of Nitric acid and Sulfuric acid. There was some particles I was unable to filter and ended up leaving them because I wasn't sure what to do with them. They were big yellow flakes that percipitated when i (per instruction) poured the solution over ice. Polar solvents seem to have not effect on it. What is it?

You might have a mixture of all types of para and/or ortho nitro products if you didnt carefully control the temperature of the nitration.

[mreff555]

right.
So basicly... you have no idea.... right?

TNT?  carefully close your hood sash and run?  (only half joking)

[nj_bartel]

Depending on the conditions you ran it under, you could have definitely gotten some TNT.

[azmanam]

TNT MSDS (http://msds.chem.ox.ac.uk/TR/2,4,6-trinitrotoluene.html)

 General

      Synonyms: 2-methyl-1,3,5-trinitrobenzene, TNT, alpha-trinitrotoluol, tolite, tritol, entsufon, trotyl
      Use:
      Molecular formula: C6H2(CH3)(NO2)3
      CAS No: 118-96-7
      EC Index No: 609-008-00-4

Physical data

      Appearance: yellow crystals

Solubility (http://www.chm.bris.ac.uk/webprojects2001/moorcraft/TNT.htm)

Properties

        Appearance Pale yellow solid
        Solubility Almost insoluble in water, sparingly soluble in organic liquids

You're right, I'm not there... I have no idea what it is.   Given the reaction conditions and physical data you've presented, I wouldn't mess around with it.  I'd take a long weekend and let EHS clean out your hood for you.

[James Newby]

is there ay way of posting your spectrum? Any the data you managed to gain would help to determine the compound.  You cant expect people to know exactly what it is from the description 'big yellow flakes'

Was the reaction run at room temperature? How long for?

[alexjaco]

There is no way you made TNT under typical nitrating conditions.  Check out the wikipedia article, its a two step process.  Also, how is he losing the ester and getting the methyl?  The nitration of methyl benzoate is used in hundreds, probably thousands, of undergraduate labs every semester, do you think they would be doing this if there was any chance they could make TNT?

http://en.wikipedia.org/wiki/Trinitrotoluene

[mreff555]

I uploaded the spectroscopy here.

http://im1.shutterfly.com/media/47b9dc01b3127ccec63c18ac72f200000040O01Aat2Lhq1asge3nwE/cC/f%3D0/ps%3D50/r%3D0/rx%3D720/ry%3D480/

Sorry, its not the greatest quality image.

TNT synthesis is nearly identical, different ratio of nitrating solution I used 1:1, and I only let it sit for around 20 minutes
but other than that the first part is the same. I suppose I could have somehow ended up with something like that.

[macman104]

Please clarify, you say in your title methylbenzoate, but in your first post you say methylbenzene.

[nj_bartel]

There is no way you made TNT under typical nitrating conditions.  Check out the wikipedia article, its a two step process.  Also, how is he losing the ester and getting the methyl?  The nitration of methyl benzoate is used in hundreds, probably thousands, of undergraduate labs every semester, do you think they would be doing this if there was any chance they could make TNT?

http://en.wikipedia.org/wiki/Trinitrotoluene

Yes, it's two different steps, but they use nearly the same reagents.

[James Newby]

im pretty sure TNT is one of the hardest molecules to make as each Nitro group deactivates the ring. If the reaction was done in an undergraduate lab ther would be strict safety instructions to prevent making any dangerous molecules.

I personally think you have a mixture of para and ortho substituted Nitro toluenes and a bit of disubstituted nitrotoluene.  There may also be some starting material in there

[alexjaco]

Please clarify, you say in your title methylbenzoate, but in your first post you say methylbenzene.

I didnt even notice that, I was going answering solely on methylbenzoate

[alexjaco]

That spectra is very hard to read and an IR wont tell you much to be honest.  Do you have an NMR?

[mreff555]

I meant methylbenzoate, sorry for the confusion. And no, sorry, my lab's NMR is broke.

That spectra is very hard to read and an IR wont tell you much to be honest.  Do you have an NMR?