2-Hexanone

Last updated
2-Hexanone [1] [2]
2-Hexanone.png
2-Hexanone-3D-balls.png
Names
Preferred IUPAC name
Hexan-2-one
Other names
Methyl butyl ketone; Methyl n-butyl ketone; MNBK; Butyl methyl ketone; MBK; n-Butyl methyl ketone; Propylacetone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.008.848 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-731-1
PubChem CID
RTECS number
  • MP1400000
UNII
  • InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3 Yes check.svgY
    Key: QQZOPKMRPOGIEB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3
    Key: QQZOPKMRPOGIEB-UHFFFAOYAQ
  • O=C(C)CCCC
Properties
C6H12O
Molar mass 100.161 g·mol−1
AppearanceColorless to light yellow liquid
Odor sharp, acetone-like [3]
Density 0.8113 g/cm3
Melting point −55.5 °C (−67.9 °F; 217.7 K)
Boiling point 127.6 °C (261.7 °F; 400.8 K)
1.4% (14 g/L)
Vapor pressure 1.3 kPa (20 °C)
-69.1·10−6 cm3/mol
1.403 (20 °C)
Viscosity 0.63 mPa·s (20 °C)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H226, H336, H361f, H372
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P303+P361+P353, P304+P340, P308+P313, P312, P314, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
2
3
0
Flash point 25 °C (77 °F; 298 K)
423 °C (793 °F; 696 K)
Explosive limits  ?-8% [3]
Lethal dose or concentration (LD, LC):
2590 mg/kg (oral, rat)
2430 mg/kg (oral, mouse)
4860 mg/kg (dermal, rabbit)
2590 mg/kg (oral, guinea pig) [4]
914 mg/kg (rat, oral) [4]
8000 ppm (rat, 4 hr) [4]
20,000 ppm (guinea pig, 70 min) [4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (410 mg/m3) [3]
REL (Recommended)
TWA 1 ppm (4 mg/m3) [3]
IDLH (Immediate danger)
1600 ppm [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2-Hexanone (methyl butyl ketone, MBK) is a ketone used as a general solvent and in paints. It dissolves cellulose nitrate, vinyl polymers and copolymers, and natural and synthetic resins. It is recommended as a solvent because it is photochemically inactive; [5] however it has a very low safe threshold limit value. 2-Hexanone is absorbed through the lungs, orally and dermally and its metabolite, 2,5-hexanedione, is neurotoxic. [6] Animal tests have shown that the neurotoxic effect of 2-hexanone may be potentiated by simultaneous administration of 2-butanone (methyl ethyl ketone, MEK). [7]

Related Research Articles

Butanone Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

Iodoform Chemical compound

Iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless, oil. It is widely used in vulcanization (crosslinking) of polymers.

Cyclohexanol 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.

2-Pentanone Chemical compound

2-Pentanone or methyl propyl ketone (MPK) is a ketone and solvent of minor importance. It is comparable to methyl ethyl ketone, but has a lower solvency and is more expensive. It occurs naturally in Nicotiana tabacum (Tobacco) and blue cheese as a metabolic product of Penicillium mold growth.

3-Pentanone Chemical compound

3-Pentanone is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

Methyl acetate Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

Diisopropyl ether Chemical compound

Diisopropyl ether is secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

2-Butanol Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

Methyl isobutyl ketone Chemical compound

Methyl isobutyl ketone (MIBK) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

Mesityl oxide Chemical compound

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

Dimethyl phthalate Chemical compound

Dimethyl phthalate is an organic compound with molecular formula (C2H3O2)2C6H4. The methyl ester of phthalic acid, it is a colorless liquid that is soluble in organic solvents.

Crotonaldehyde Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

Isophorone Alpha-beta unsaturated cyclic ketone

Isophorone is an α,β-unsaturated cyclic ketone. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a solvent and as a precursor to polymers, it is produced on a large scale industrially.

Methyl isopropyl ketone Chemical compound

3-Methyl-2-butanone is a ketone and solvent of minor importance. It is comparable to MEK, but has a lower solvency and is more expensive.

Methyl cyanoacrylate Chemical compound

Methyl cyanoacrylate (MCA) is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

3-Heptanone Chemical compound


3-Heptanone, is a seven carbon ketone. It is a colorless liquid with a "green odor," also described to have a fruity scent. It is often used as a perfume/fragrance, as a solvent for cellulose, nitrocellulose, or vinyl resins, and as a synthetic building block in the preparation of other organic molecules.

3-Methyl-2-pentanone Chemical compound

3-Methyl-2-pentanone is an aliphatic ketone and isomer of 2-hexanone. It is used as a solvent and as an intermediate for syntheses. Its industrial importance is low. It is produced by base-catalyzed aldol condensation of 2-butanone with acetaldehyde, forming 4-hydroxy-3-methyl-2-pentanone, which is dehydrated to 3-methyl-3-penten-2-one over an acid catalyst, followed by hydrogenation over a palladium catalyst.

References

  1. ↑ Merck Index , 11th Edition, 5955.
  2. ↑ CRC Handbook of Chemistry and Physics, 75th ed. (1995)
  3. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0325". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 3 4 "2-Hexanone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ Dieter Stoye (2007), "Solvents", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 56
  6. ↑ Jerrold B. Leikin; Frank P. Paloucek (2008), "2-Hexanone", Poisoning and Toxicology Handbook (4th ed.), Informa, p. 737
  7. ↑ Wilhelm Neier; Günter Strehlke (2007), "2-Butanone", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 6
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