3-Heptanone

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3-Heptanone
3-heptanone.svg
Names
Preferred IUPAC name
Heptan-3-one
Other names
Ethyl butyl ketone
3-Oxoheptane
Butyl ethyl ketone
Identifiers
3D model (JSmol)
506161
ChEBI
ChemSpider
ECHA InfoCard 100.003.081 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-388-1
MeSH 3-Heptanone
PubChem CID
RTECS number
  • MJ5250000
UNII
UN number 1224
  • InChI=1S/C7H14O/c1-3-5-6-7(8)4-2/h3-6H2,1-2H3
    Key: NGAZZOYFWWSOGK-UHFFFAOYSA-N
  • CCC(=O)CCCC
Properties
C7H14O
Molar mass 114.188 g·mol−1
AppearanceColorless liquid
Odor powerful, fruity [1]
Density 0.812 g cm−3
Melting point −39 °C (−38 °F; 234 K)
Boiling point 146 to 149 °C (295 to 300 °F; 419 to 422 K)
1% (20 °C) [1]
Vapor pressure 4 mmHg (20 °C) [1]
Hazards
Safety data sheet [2]
GHS pictograms GHS-pictogram-flamme.svg GHS-pictogram-acid.svg
GHS Signal word Warning
H226, H319, H332
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+361+353, P304+312, P304+340, P305+351+338, P312, P337+313, P370+378, P403+235, P501
Flash point 41 °C (106 °F; 314 K)
Lethal dose or concentration (LD, LC):
2760 mg/kg (rat, oral) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 50 ppm (230 mg/m3) [1]
REL (Recommended)
TWA 50 ppm (230 mg/m3) [1]
IDLH (Immediate danger)
1000 ppm [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references


3-Heptanone (butyl ethyl ketone), 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. [4]

Preparation

3-Heptanone is produced industrially through reductive condensation of propionaldehyde (propanal) with butanone (methyl ethyl ketone). This reaction yields hept-4-en-3-one, which is subsequently hydrogenated to 3-heptanone.

CH
3
CH
2
CHO
  +   CH
3
C(O)CH
2
CH
3
  CH
3
CH
2
C(O)CHCHCH
2
CH
3
  +   H
2
O
CH
3
CH
2
C(O)CHCHCH
2
CH
3
  +   H
2
  CH
3
CH
2
C(O)CH
2
CH
2
CH
2
CH
3

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.

Ethanethiol Chemical compound

Ethanethiol, commonly known as ethyl mercaptan and stench, is a clear liquid with a distinct odor. It is an organosulfur compound with the formula CH3CH2SH. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

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.

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.

Ethyl acetate Chemical compound

Ethyl acetate is the organic compound with the formula CH
3
−COO−CH
2
−CH
3
, simplified to C
4
H
8
O
2
. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

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.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). It is one of the four isomers of butanol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

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.

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.

Butyl acetate Chemical compound

n-Butyl acetate, also known as butyl ethanoate, is an ester that is a colorless, flammable liquid at room temperature. It is found in many types of fruit, where along with other chemicals, it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as a synthetic fruit flavoring in foods such as candy, ice cream, cheeses, and baked goods. Butyl acetate is often used as a high-boiling solvent of moderate polarity. It is also used as a solvent in nail polish along with ethyl acetate.

Diacetone alcohol Chemical compound

Diacetone alcohol is an organic compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This colorless liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.

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.

p-Anisidine (para-anisidine) is an organic compound with the formula CH3OC6H4NH2. A white solid, commercial samples can appear grey-brown owing to air oxidation. It is one of three isomers of anisidine, methoxy-containing anilines. It is prepared by reduction of 4-nitroanisole.

2-Hexanone Chemical compound

2-Hexanone 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; 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. Animal tests have shown that the neurotoxic effect of 2-hexanone may be potentiated by simultaneous administration of 2-butanone.

Dinitro-<i>ortho</i>-cresol Chemical compound

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. DNOC and some related derivatives have been used as herbicides.

Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.

Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to polybutylacrylate, which is used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.

References

  1. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0266". National Institute for Occupational Safety and Health (NIOSH).
  2. http://www.chemicalbook.com/ProductMSDSDetailCB0852672_EN.htm External MSDS
  3. "Ethyl butyl ketone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. Siegel, Hardo; Eggersdorfer, Manfred (2012). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry . 20. p. 195. doi:10.1002/14356007.a15_077. ISBN   9783527306732.