Nitrolic acid
Nitrolic acids are organic compounds with the functional group RC(NO2)=NOH. They are prepared by the reaction of nitroalkanes with base and nitrite sources:[1]
- RCH2NO2 + HNO2 → RC(NO2)=NOH + H2O
The conversion was first demonstrated by Victor Meyer using nitroethane.[2] The reaction proceeds via the intermediacy of the nitronate anion.
Occurrence
[edit | edit source]Most nitrolic acids are laboratory curiosities. One exception is the compound HO2C(CH2)4C(NO2)=NOH, which is produced by the oxidation of cyclohexanone with nitric acid.[3] This species decomposes to adipic acid and nitrous oxide:
- HO2C(CH2)4C(NO2)=NOH → HO2C(CH2)4CO2H + N2O
This conversion is thought to be the largest anthropogenic route to N2O, which, on a molecule-to-molecule basis, has 298 times the atmospheric heat-trapping ability of carbon dioxide.[4] Adipic acid is a precursor to many nylon polymers. In the end, nitrous oxide is produced in about one to one mole ratio to the adipic acid.[5]
References
[edit | edit source]- ^ Matt, C.; Wagner, A.; Mioskowski, C., "Novel Transformation of Primary Nitroalkanes and Primary Alkyl Bromides to the Corresponding Carboxylic Acids", The Journal of Organic Chemistry 1997, 62, 234-235. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Meyer, V.; Locher, J. "Untersuchungen über die Constitution der Nitrolsäuren (Researches on the constitution of the nitrolic acids)" Deut. Chem. Ges. Ber., 1874, volume 7, pp. 670-5. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
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