VSEPR_VOID
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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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AvBaeyer
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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.
AvB
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Aqua-regia
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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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S.C. Wack
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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.
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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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Dr.Bob
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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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VSEPR_VOID
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| 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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zed
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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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Waffles SS
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| 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
Chemistry = Chem + is + Try
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zed
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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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Waffles SS
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You are welcome.(Thanks Magpie for creating that topic too)
[Edited on 28-10-2018 by Waffles SS]
Chemistry = Chem + is + Try
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Tdep
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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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Heptylene
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School project? Does your school have access to scifinder and/or reaxys? Very useful to find syntheses for specific compounds
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S.C. Wack
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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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Tsjerk
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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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