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Nitration is a general class of chemical processes for the introduction of a nitro group into an organic chemical compound.
Nitration vs nitrate esters
More loosely the term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid, as occurs in the synthesis of nitroglycerin and nitrocellulose. The difference between the resulting structure of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, typically carbon or another nitrogen atom, whereas in nitrate esters the nitrogen is bonded to an oxygen atom that in turn is bonded to a carbon atom.
Free radical aliphatic nitration occurs at very high temperatures, in gas phase, between alkanes and nitric acid or dinitrogen tetroxide. The reaction produces a variety of nitro compounds, the ratio depends on the catalysts used (or not used).
- C3H8 + HNO3 → CH3CH2CH2NO2 + CH3CH(NO2)CH3 + CH3CH2NO2 + CH3NO2
All the products are separated using fractional distillation.
Typical nitration syntheses use a mixture of concentrated nitric acid and sulfuric acids, called nitrating mixture or mixed acid. This mixture produces the nitronium ion (NO2+), which is the active species in aromatic nitration. A more stable source of nitronium ion is nitronium tetrafluoroborate, which can replace the nitrating mixture. In mixed-acid syntheses, sulfuric acid is not consumed and acts as a catalyst as well as an absorbent for water.
Nitrating organic compounds is a dangerous procedure that uses corrosive oxidizing mixtures. Proper protection must be worn at all times. Temperature control is important, as some compounds may decompose if the reaction temperature is too high.
Relevant Sciencemadness threads
- Wich salt makes the most attractive nitration mix with H2SO4?
- Nitration Calculations
- nitration without sulfuric acid
- Nitration without sulfuric acid?
- Olah's Nitration Book
- Nitration of Propenylbenzenes
- abnormal nitration of styrene
- Nitration of phthalic acid
- Aromatic nitration with Guanidine Nitrate
- Toluene Nitration Using Nitrate Salts
- Nitration of hexamine via patent 3981975?
- Nitration of xylene
- Ortho Nitration