Author Topic: toulene for benzene  (Read 2363 times)

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Vibrating_Lights

  • Guest
toulene for benzene
« on: February 23, 2002, 09:52:00 AM »
Is toulene interchangable with benzene in alumina cromotography applications?
VL_

terbium

  • Guest
Re: toulene for benzene
« Reply #1 on: February 23, 2002, 10:20:00 AM »
Toluene is not exactly the same but in many cases it will be a suitable substitute for benzene (and much less toxic).

Vibrating_Lights

  • Guest
Re: toulene for benzene
« Reply #2 on: February 23, 2002, 11:12:00 AM »
Is that a yes then for alumina supported amine chromotography applications?
VL_

Flip

  • Guest
Re: toulene for benzene
« Reply #3 on: February 23, 2002, 11:28:00 PM »
The only difference is a methyl group.  If toulene can gain nitrogens to form tnt (tri-nitro-toulene) then I suppose it functions with nitrogen much like a benzene.  But I'm not exactly an authority on the subject.

Vibrating_Lights

  • Guest
Re: toulene for benzene
« Reply #4 on: February 23, 2002, 11:58:00 PM »
Nitro usually refers to the addition of NO groups.
VL_

Flip

  • Guest
Re: toulene for benzene
« Reply #5 on: February 24, 2002, 12:38:00 AM »
Thanks dude i'm still figuring all of this stuff out.  NO's and NH3's would have a different reactivity.  Can NH3's bond to toulene? I think they could (don't see any reason why they wouldn't), and if so it would be an amine right?  If it were an amine like any other it'd probably work. Unless theres stuff i'm not considering, so if someone gets a chance please enlighten me.
:( , but it's an interesting question.

little sub-question how would toulene be aminated?

Flip

PrimoPyro

  • Guest
Re: toulene for benzene
« Reply #6 on: February 24, 2002, 12:47:00 AM »
Flip, you are rambling and not making any sense. What are you talking about?

                                                    PrimoPyro

The Water Will Be Your Only Mirror

Vibrating_Lights

  • Guest
Re: toulene for benzene
« Reply #7 on: February 24, 2002, 12:54:00 AM »
He wants to know if he can aminate toulene and how would he go about doing it.
Probably not in the case you are describinh NH3 is a neucleophile In amination there is usually an atom nescesary that will bond with one of the H from the NH3
For example in a Bromosafrole amination with NH3( doesn't work very well)  the Br would combine with H leaving you with MDA + HBr.  With toulene there really isn't any unsatisfied atoms that would provide a good leaving group.
VL_

PrimoPyro

  • Guest
Re: toulene for benzene
« Reply #8 on: February 24, 2002, 01:07:00 AM »
Aminate it where? On the ring, or on the methyl group? Both answers are yes of course.

To aminate the ring: You could nitrate it with nitric acid and sulfuric acid, or a nitrate salt and sulfuric acid, followed by reduction of the nitro group(s) to form the amine(s). This gives a mixture of three possible isomers, but if a nitrate salt is used, you really only get two of them in apreciable amounts: the ortho and para isomers. You can further tweak isomer selectivity (somewhat) by using specific salts of nitric acid, namely sodium for para and potassium for ortho.

You can also use ammonia, toluene, and catalytic ammonium iodide, with photolytic amination via a benzyne intermediate. There is a post in the Novel Discourse that offers some information about this. The information was read in a patent.

To aminate the methyl group, Im sure there are a bazillion ways, most starting from better things than toluene, but here's a few:

1.KMnO4 oxidation to benzoic acid, followed by distillation from ammonia, resulting in benzamide. Dehydrate this with P2O5 to cyanobenzene, and reduce this with sodium borohydride to benzylamine.

2.Chlorinate toluene with calcium hypochlorite, forming benzyl chloride, and react with ammonia.

3.Chlorinate toluene with calcium hypochlorite, forming benzyl chloride, react with sodium cyanide, forming phenylacetonitrile, hydrolyze to phenylacetic acid with sulfuric acid, then distill from ammonia, resulting in formation of phenylacetamide, and react with calcium hypochlorite to rip the carbonyl off, resulting in benzylamine.

4.many other and better ways, starting from things better than toluene.

                                                     PrimoPyro

The Water Will Be Your Only Mirror

Flip

  • Guest
Re: toulene for benzene
« Reply #9 on: February 24, 2002, 04:57:00 AM »
Pyro that is a great explanation, thank you for helping me to understand nitration, halogenationation, and some different ways to benzylamine.  I am still in my larvae-studying stage and have a lot to learn.  I guess I just like to theorize so people will tell me whether or not I am right about stuff. However non-sensical it may be to a real chemist.

PrimoPyro

  • Guest
Re: toulene for benzene
« Reply #10 on: February 24, 2002, 05:05:00 AM »
I am much like yourself + shitloads of reading anything I can get my hands on/click my mouse on. Keep reading, it's good for you.  8)

                                                  PrimoPyro

The Water Will Be Your Only Mirror