Cycloheptanone
Encyclopedia
Cycloheptanone,6CO, is a cyclic ketone also referred to as suberone. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals.
of calcium suberate yields calcium carbonate and suberone:
Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400 – 450 °C over alumina doped with zinc oxide or cerium oxide.
Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide
and nitromethane
. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to acetic acid
and shaken with hydrogen gas in the presence of W-4 Raney nickel
catalyst. Sodium nitrite
and acetic acid are then added to give cycloheptanone.
Cycloheptanone is also prepared by ring expansion of cyclohexanone
with diazomethane
as the methylene source.
, a spasmolytic agent and vasodilator is produced from it, for example. Pimelic acid
is produced by the oxidative cleavage of cycloheptanone. Dicarboxylic acid
s such as pimelic acid
are useful for the preparation of fragrances and certain polymers.
Several microorganisms, including Mucor plumbeus, Mucor racemosus, and Penicillium chrysogenum, have been found to reduce cycloheptanone to cycloheptanol. These microorganisms have been investigated for use in certain stereospecific enzymatic reactions.
Synthesis
In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The destructive distillationDestructive distillation
Destructive distillation is the chemical process involving the decomposition of feedstock by heating to a high temperature; the term generally applies to processing of organic material in the absence of air or in the presence of limited amounts of oxygen or other reagents, catalysts, or solvents,...
of calcium suberate yields calcium carbonate and suberone:
- Ca(O2C(CH2)6CO2) → CaCO3 + (CH2)6CO
Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400 – 450 °C over alumina doped with zinc oxide or cerium oxide.
Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide
Sodium ethoxide
Sodium ethoxide is an alkoxide salt with the chemical formula C2H5ONa.-Preparation:It is commercially available as a white solid, or as a solution in ethanol. It is easily prepared in the laboratory by reacting sodium metal with ethanol:...
and nitromethane
Nitromethane
Nitromethane is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a slightly viscous, highly polar liquid commonly used as a solvent in a variety of industrial applications such as in extractions, as a reaction medium, and as a cleaning solvent...
. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...
and shaken with hydrogen gas in the presence of W-4 Raney nickel
Raney nickel
Raney nickel is a solid catalyst composed of fine grains of a nickel-aluminium alloy, used in many industrial processes. It was developed in 1926 by American]] engineer Murray Raney as an alternative catalyst for the hydrogenation of vegetable oils in industrial processes...
catalyst. Sodium nitrite
Sodium nitrite
Sodium nitrite is the inorganic compound with the chemical formula NaNO2. It is a white to slight yellowish crystalline powder that is very soluble in water and is hygroscopic...
and acetic acid are then added to give cycloheptanone.
Cycloheptanone is also prepared by ring expansion of cyclohexanone
Cyclohexanone
Cyclohexanone is the organic compound with the formula 5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation...
with diazomethane
Diazomethane
Diazomethane is the chemical compound CH2N2. It is the simplest of diazo compounds. In the pure form at room temperature, it is a extremely sensitive explosive yellow gas, thus it is almost universally used as a solution in diethyl ether...
as the methylene source.
Uses and reactions
Cycloheptanone has no direct applications, but is a precursor to other compounds. BencyclaneBencyclane
Bencyclane is a calcium channel blocker....
, a spasmolytic agent and vasodilator is produced from it, for example. Pimelic acid
Pimelic acid
Pimelic acid is the organic compound with the formula HO2C5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides...
is produced by the oxidative cleavage of cycloheptanone. Dicarboxylic acid
Dicarboxylic acid
Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group...
s such as pimelic acid
Pimelic acid
Pimelic acid is the organic compound with the formula HO2C5CO2H. Derivatives of pimelic acid are involved in the biosynthesis of the amino acid called lysine. Pimelic acid is one methylene longer than a related dicarboxylic acid, adipic acid, a precursor to many polyesters and polyamides...
are useful for the preparation of fragrances and certain polymers.
Several microorganisms, including Mucor plumbeus, Mucor racemosus, and Penicillium chrysogenum, have been found to reduce cycloheptanone to cycloheptanol. These microorganisms have been investigated for use in certain stereospecific enzymatic reactions.