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Author: Subject: Looking for Information on 2-nitrotoluene
VSEPR_VOID
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[*] posted on 23-10-2018 at 16:28
Looking for Information on 2-nitrotoluene


I have a school project coming up that calls for the nitration of C60(PhCH3)12. I want use conditions that give a mononitrated product, which will later be reduced with tin and HCl(aq).

Does anyone have any links to protocols for mononitrations of toluene or preparing 2-nitrotoluene?

I have already checked the SM library, Vogel, PrepChem, and Google Scholar.

Thanks




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[*] posted on 23-10-2018 at 19:29


Search the Pre-pub section. There are reliable methods described there.

If you searched outside SciMad properly, you would have found many detailed published methods.

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[*] posted on 24-10-2018 at 12:21


Selective nitration for toluene does not exist. The ratio is appr. 60% 2-nitro-, 37% 4-nitro-, and 3% 3 nitrotoluene. (lit.)

There is a paper for ratio of nitrotouelen isomers, using variable nitrating acid mix:

HARRIS, G. F. P. (1976). Isomer Control in the Mononitration of Toluene. Industrial and Laboratory Nitrations, 300–312. doi:10.1021/bk-1976-0022.ch020

But follow Vogel, this is very trustworthy. For that matter, toluene nitrating is very basic prep, you can it seeking out almost in every prep book.

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[*] posted on 24-10-2018 at 15:37


Quote: Originally posted by Aqua-regia  
But follow Vogel, this is very trustworthy. For that matter, toluene nitrating is very basic prep, you can it seeking out almost in every prep book.


You're talking about nitrobenzene. The directions for nitrobenzene may be a little aggressive for the easily dinitrated toluene. Dinitrotoluene has a bad habit of exploding on distillation. Even when the industrial directions are followed, direct fractionation of the washed organic phase can be too much heat for too long and it decides to explode regardless. (I recommend a prior steam distillation if fractional distillation is to be done)

Urbanski, TNT Trinitrotoluenes &et c., Systematic Organic Chemistry

[Edited on 24-10-2018 by S.C. Wack]




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[*] posted on 24-10-2018 at 18:03


I don't see the distillation of C60(PhCH3NO2)12 being a good option, no matter what ratio of products you get.

You will need to be very mild for that type of compound, but not sure if you are looking for 12-nitro reaction or juts want to put one nitro on one ring of the entire molecule.
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[*] posted on 24-10-2018 at 21:46


Quote: Originally posted by Dr.Bob  
I don't see the distillation of C60(PhCH3NO2)12 being a good option, no matter what ratio of products you get.

You will need to be very mild for that type of compound, but not sure if you are looking for 12-nitro reaction or juts want to put one nitro on one ring of the entire molecule.


I would not be distilling it. I was thinking that the C60(PhCH3)12 would be added to the nitric acid, then sulfuric acid would slowly be added. The product would be extracted will chloroform then the solvent evaporated off.

I have to use toluene instead of benzene because my science fairs science regulatory commission prohibited benzene. They have been a pain in my ass for years, and I suspect they will be for decades to come: "No, you cant use benzene", "No, you cant edit human embryos", "No, you cant experiment on the homeless", "No, that was banned under the Geneva convention".





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[*] posted on 26-10-2018 at 13:21


Ummm; o-nitrotoluene?

Must be somewhere in Org.Syn., but I haven't located it yet.

http://www.orgsyn.org/Result.aspx
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[*] posted on 26-10-2018 at 13:34


Quote: Originally posted by VSEPR_VOID  
I have a school project coming up that calls for the nitration of C60(PhCH3)12. I want use conditions that give a mononitrated product, which will later be reduced with tin and HCl(aq).

Does anyone have any links to protocols for mononitrations of toluene or preparing 2-nitrotoluene?

I have already checked the SM library, Vogel, PrepChem, and Google Scholar.

Thanks


http://www.sciencemadness.org/talk/viewthread.php?tid=29111




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[*] posted on 26-10-2018 at 14:11


Thank you Waffles SS, your link was better than anything else I found floating around. There are a couple of examples on Youtube.

O-nitrotoluene is a useful intermediary.

Void, I'm not clear exactly what you are trying to do. Nitrating a Fullerene?

Got a picture of that Fullerene somewhere?



[Edited on 26-10-2018 by zed]
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[*] posted on 27-10-2018 at 23:24


Quote: Originally posted by zed  
Thank you Waffles SS, your link was better than anything else I found floating around.


You are welcome.(Thanks Magpie for creating that topic too)

[Edited on 28-10-2018 by Waffles SS]




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[*] posted on 28-10-2018 at 02:45


Quote: Originally posted by Aqua-regia  
Selective nitration for toluene does not exist.


I remember there was a Chemplayer video where they followed a procedure for selective nitration, or mostly selective, of toluene to o-nitrotoluene. It used DCM + RFNA as the nitration mix. Clever stuff
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[*] posted on 28-10-2018 at 03:24


School project? Does your school have access to scifinder and/or reaxys? Very useful to find syntheses for specific compounds
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[*] posted on 28-10-2018 at 07:48


Quote: Originally posted by Heptylene  
Does your school have access to scifinder and/or reaxys?


After spending all their money on C60(PhCH3)12, fake phthalic anhydride (for nitrophthalic acid of course) and nitroethane (definitely not for P2NP); perhaps bake sales of the student preparations (not Bifetamin tea) are what will allow them to build the large pile of cash needed for such toys.




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[*] posted on 28-10-2018 at 08:32


Sure, nitration of toluene in order to get a direct anesthetic precursor... in school, without proper documentation of the procedure.

It is disrespectful, especially for someone who is not new here, to post lame excuses like doing a "school project". If you do something you think cannot see daylight, don't do it or admit doing it. Nowhere on this forum it says you have to come up with lame excuses when doing something not legal in your jurisdiction.

Do you think we are stupid?

Edit ; you separate the isomers by melting point btw


[Edited on 28-10-2018 by Tsjerk]

[Edited on 28-10-2018 by Tsjerk]
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