The Vespiary

The Hive => Newbee Forum => Topic started by: dextro on September 04, 2004, 05:02:00 PM

Title: p2np question
Post by: dextro on September 04, 2004, 05:02:00 PM

in the synthesis of phenyl-2-nitropropene via nitroethane/benzaldehyd/n-butylamine is frequently a solvent (toluene) used.
what is the reason for the use of a solvent?
swim found some threads where p2np is produced with good succes without any solvent.
and at last: when toluene is used, must this distilled off before crystallization or is this not necessary ?

yes, swim utfse, but there is no uniform opinion.

thx

Title: Solvents in the synthesis of Phenyl-2-Nitropropene
Post by: Rhodium on September 05, 2004, 10:45:00 PM

what is the reason for the use of a solvent?

To be able to speed up the reaction by heating it and to continuously distill off the water formed in the reaction.
Heating the reaction mixture without a solvent present would likely overheat the product.

when toluene is used, must this distilled off before crystallization or is this not necessary?

If the reaction mixture is cooled in the fridge before filtering, most of the product will precipitate even in the presence of the solvent.
(At least as long as you don't use larger amounts than suggested in the

literature methods (https://www.thevespiary.org/rhodium/Rhodium/chemistry/phenyl-2-nitropropene.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/phenyl-2-nitropropene.html))

Title: swid did two attempts: 1.
Post by: dextro on September 13, 2004, 09:07:00 PM

swid did two attempts:

1.  100ml EtOH
    101ml BA
     79ml NE
     20ml n-But.amin

     refluxed 2 hours at 83° C.
     Result: one layer of red/orange layer. Put this in   
     the freezer: milky white upper layer appeared and  
     sucked away.
     orange/red layer cooled again down to -10°C and then
     swirled to bring it in contact with air:
     the whole mass crystallized in a few seconds.
     re-X with IPA gave a beaker full of near white  
     sparkling beauties ;D

2.  no solvent  was used
    49 ml BA
    38 ml NE
     6 ml n-Butyla.

    refluxed for 2 hours at 100°C
    result: water layer over a deep orange oil layer.
    water drained away with sep. funnel.
    oil cooled again to -10°C, swirled to bring it in  
    contact with air and -again- the whole shebang  
    crystallized in a few seconds.
    > re-X with IPA > some result as in the first attempt

yield is over 80% in 1. + 2.

the trick is: to cool it down in the freezer and then swirl it with a glas rod to bring air in the oil.
dean-stark trap was not necessary

greez

Title: sounds good
Post by: Radiumhero on September 22, 2004, 01:14:00 PM