![NitrolicAcidFxnlGp](https://upload.wikimedia.org/wikipedia/commons/2/23/NitrolicAcidFxnlGp.png)
Nitrolic acids are
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
s with the
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
RC(NO
2)=NOH. They are prepared by the reaction of
nitroalkane
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitr ...
s with base and nitrite sources:
:RCH
2NO
2 + HNO
2 → RC(NO
2)=NOH + H
2O
The conversion was first demonstrated by
Victor Meyer
Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meyer apparatus, and f ...
using
nitroethane
Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.
Preparati ...
.
[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. ] The reaction proceeds via the intermediacy of the
nitronate
A nitronate (IUPAC: azinate) in organic chemistry is a functional group with the general structure . It is the anion of nitronic acid (sometimes also called an aci, or an azinic acid), a tautomeric form of a nitro compound. Just as ketones and al ...
anion.
Occurrence
Most nitrolic acids are laboratory curiosities. One exception is the compound HO
2C(CH
2)
4C(NO
2)=NOH, which is produced by the oxidation of
cyclohexanone
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohexan ...
with
nitric acid
Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...
.
This species decomposes to
adipic acid
Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annually, ...
and
nitrous oxide
Nitrous oxide (dinitrogen oxide or dinitrogen monoxide), commonly known as laughing gas, nitrous, or nos, is a chemical compound, an oxide of nitrogen with the formula . At room temperature, it is a colourless non-flammable gas, and has a ...
:
:HO
2C(CH
2)
4C(NO
2)=NOH → HO
2C(CH
2)
4CO
2H + N
2O
This conversion is thought to be the largest anthropogenic route to N
2O, which, on a molecule-to-molecule basis, has 298 times the atmospheric heat-trapping ability of carbon dioxide.
Adipic acid is a precursor to many
nylon
Nylon is a generic designation for a family of synthetic polymers composed of polyamides ( repeating units linked by amide links).The polyamides may be aliphatic or semi-aromatic.
Nylon is a silk-like thermoplastic, generally made from petro ...
polymers. In the end, nitrous oxide is produced in about one to one mole ratio to the adipic acid.
References
{{reflist , 30em
Functional groups
Organonitrogen compounds