Cyclohexanone oxime

Last updated
Cyclohexanone oxime
Structure of cyclohexanone oxime.png
Cyclohexanone-oxime-from-xtal-2004-Mercury-3D-balls.png
Names
Preferred IUPAC name
N-Hydroxycyclohexanimine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.613 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-874-0
PubChem CID
UNII
UN number 2811
  • InChI=1S/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2
    Key: VEZUQRBDRNJBJY-UHFFFAOYSA-N
  • InChI=1/C6H11NO/c8-7-6-4-2-1-3-5-6/h8H,1-5H2
    Key: VEZUQRBDRNJBJY-UHFFFAOYAH
  • C1CCC(=NO)CC1
Properties
C6H11NO
Molar mass 113.16 g/mol
Appearancewhite solid
Melting point 88 to 91 °C (190 to 196 °F; 361 to 364 K)
Boiling point 204 to 206 °C (399 to 403 °F; 477 to 479 K)
16 g/kg (in water)
-71.52·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H228, H302, H319, H373, H412
P210, P240, P241, P260, P264, P270, P273, P280, P301+P312, P305+P351+P338, P314, P330, P337+P313, P370+P378, P501
Flash point 110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.

Contents

Preparation

Cyclohexanone oxime can be prepared from the condensation reaction between cyclohexanone and hydroxylamine: [1]

C5H10CO + H2NOH → C5H10C=NOH + H2O

Alternatively, another industrial route involves the reaction of cyclohexane with nitrosyl chloride, which is a free radical reaction. This method is advantageous as cyclohexane is much cheaper than cyclohexanone.

Reactions

The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam:

Beckmann rearrangement of cyclohexanone oxime.png

This reaction is catalyzed by sulfuric acid, [1] but industrial scale reactions use solid acids. [2]

Typical of oximes, the compound can be reduced by sodium amalgam to produce cyclohexylamine. [3] It can also be hydrolyzed with acetic acid to give back cyclohexanone.

Related Research Articles

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group. The simplest ketone is acetone, with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Beckmann rearrangement</span>

The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. The rearrangement has also been successfully performed on haloimines and nitrones. Cyclic oximes and haloimines yield lactams.

<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.

<span class="mw-page-title-main">Cyclohexanol</span> Chemical compound

Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Billions of kilograms are produced annually, mainly as a precursor to nylon.

Bromobenzene is an aryl halide, C6H5Br. It is a colourless liquid although older samples can appear yellow. It is a reagent in organic synthesis.

<span class="mw-page-title-main">Caprolactam</span> Chemical compound

Caprolactam (CPL) is an organic compound with the formula (CH2)5C(O)NH. This colourless solid is a lactam (a cyclic amide) of caproic acid. Global demand for this compound is approximately five million tons per year, and the vast majority is used to make Nylon 6 filament, fiber, and plastics.

<span class="mw-page-title-main">Benzoyl chloride</span> Organochlorine compound (C7H5ClO)

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

<span class="mw-page-title-main">Cyclohexanone</span> Chemical compound

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 cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

<span class="mw-page-title-main">1,4-Benzoquinone</span> Chemical compound

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<span class="mw-page-title-main">Hydroperoxide</span> Class of chemical compounds

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<span class="mw-page-title-main">Cyclohexanecarboxylic acid</span> Chemical compound

Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature.

<span class="mw-page-title-main">Nitrosyl chloride</span> Chemical compound

Nitrosyl chloride is the chemical compound with the formula NOCl. It is a yellow gas that is commonly encountered as a component of aqua regia, a mixture of 3 parts concentrated hydrochloric acid and 1 part of concentrated nitric acid. It is a strong electrophile and oxidizing agent. It is sometimes called Tilden's reagent, after William A. Tilden, who was the first to produce it as a pure compound.

The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.

<span class="mw-page-title-main">4-Nitroaniline</span> Chemical compound

4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.

Flash vacuum pyrolysis (FVP) is a technique in organic synthesis. It entails heating a precursor molecule intensely and briefly. Two key parameters are the temperature and duration, which are adjusted to optimize yield, conversion, and avoidance of intractable products. Often the experiment entails volatilizing a precursor, which is drawn through a "hot zone" followed by rapid condensation. The apparatus typically is conducted under dynamic vacuum. The hot zone must impart heat to the gaseous molecules, so it is generally packed with solids to induce gas-solid collisions. The packing material is generally chemically inert, such as quartz. The precursor (i) volatilizes with gentle heating and under vacuum, (ii) the precursor fragments or rearranges in the hot zone, and finally (iii) the products are collected by rapid cooling. Rapid post-reaction cooling and the dilution inherent in gases both suppress bimolecular degradation pathways.

<span class="mw-page-title-main">1-Tetralone</span> Chemical compound

1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor. It is used as starting material for agricultural and pharmaceutical agents. The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.

Hydroxylamine-<i>O</i>-sulfonic acid Chemical compound

Hydroxylamine-O-sulfonic acid (HOSA) is the inorganic compound with molecular formula H3NO4S that is formed by the sulfonation of hydroxylamine with oleum. It is a white, water-soluble and hygroscopic, solid, commonly represented by the condensed structural formula H2NOSO3H, though it actually exists as a zwitterion and thus is more accurately represented as +H3NOSO3. It is used as a reagent for the introduction of amine groups (–NH2), for the conversion of aldehydes into nitriles and alicyclic ketones into lactams (cyclic amides), and for the synthesis of variety of nitrogen-containing heterocycles.

<i>N</i>-Hydroxyphthalimide Chemical compound

N-Hydroxyphthalimide is the N-hydroxy derivative of phthalimide. The compound can be utilized as a catalyst for oxidation reactions, in particular for the selective oxidation with molecular oxygen under mild conditions.

References

  1. 1 2 J. C. Eck and C. S. Marvel "ε-Benzoylaminocaproic Acid" Org. Synth. 1939, volume 19, pp. 20. doi : 10.15227/orgsyn.019.0020
  2. Corma, Avelino; Garcia, Hermenegildo "Organic reactions catalyzed over solid acids" Catalysis Today 1997, volume 38, pp. 257-308. doi : 10.1016/S0920-5861(97)81500-1
  3. W. H. Lycan, S. V. Puntambeker, and C. S. Marvel "n-Heptylamine" Org. Synth. 1931, volume 11, pp. 58. doi : 10.15227/orgsyn.011.0058