123-19-3

Usage

Uses

Used in Chemical Industry:
4-Heptanone is used as a solvent for nitrocellulose, oils, resins, and polymers, facilitating various chemical reactions and processes in the industry.
Used in Flavor and Fragrance Industry:
4-Heptanone is used in the preparation of flavorings, providing fruity, banana, green apple, and blue cheese with nut-like nuances at 5 ppm. Its aroma characteristics at 1.0% include sweet ethereal, banana fruity, pungent, and green apple with cheese nuances.
Used in Organic Synthesis:
4-Heptanone serves as a raw material for organic synthesis, contributing to the production of various chemical compounds and intermediates.
Used in Pharmaceutical Industry:
4-Heptanone is used as an intermediate in the synthesis of active pharmaceutical ingredients, playing a crucial role in the development of medications.
Used in Paints and Coatings Industry:
4-Heptanone is utilized in paints and coatings, acting as a solvent to improve the application and performance of these products.
Used in Analytical Chemistry:
4-Heptanone can be used as an internal standard of gas chromatography-mass spectrometry for the analysis of 3-monochloro-1,2-propane diol, a potential carcinogen found in soy sauce.
Production Methods:
4-Heptanone can be synthesized during the reaction of 1-butanol over base catalysts such as MgO. It can also be prepared by passing butyric acid over a wood coal at 425°C and then over cerium oxide at 500°C or over thorium oxide, as well as over manganese oxide at 400-425°C.

References

Walker V, and Mills GA. "Urine 4-heptanone: a beta-oxidation product of 2-ethylhexanoic acid from plasticisers. " Clinica Chimica Acta306.2(2001):51-61. Dayrit, F. M., and M. R. Ni?onuevo. "Development of an analytical method for 3-monochloropropane-1,2-diol in soy sauce using 4-heptanone as derivatizing agent." Food Additives & Contaminants 21.3(2004):204-9. Plint, Neville, et al. "Catalysed synthesis of 4-heptanone from 1-butanol."Catalysis Today 49.1–3(1999):71-77.

Preparation

By passing butyric acid over wood coal at 425°C and then over cerium oxide at 500°C or over thorium oxide; also over manganese oxide at 400 to 425°C.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 245, 1994 DOI: 10.1021/jo00080a042

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

4-Heptanone is incompatible with the following: Oxidizers .

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Health Hazard

Inhalation of DPK vapors can cause narcosisand irritation of the eyes and respiratory tract.Exposure to 4000 ppm for 4 hours was fatalto rats. 4-Heptanone exhibited low to verylow oral toxicity in test animals.LD50 value, oral (rats): 3730 mg/kg.

Fire Hazard

Combustible liquid; flash point (closed cup) 49°C (120°F); vapor density 3.9 (air = 1); vapor pressure 5.2 torr at 20°C (68°F); fireextinguishing agent: “alcohol” foam or water spray. DPK forms explosive mixtures with air; LEL and UEL values have not been reported. It is incompatible with strong acids, alkalies, and oxidizers. .

Biochem/physiol Actions

Taste at 5 ppm

Safety Profile

and skin contact. A skin and eye irritant. Flammable liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical, alcohol foam, fog, and mist. When heated to decomposition it emitsacrid smoke and fumes. See also KETONES.

Metabolism

When 950 mg methyl amyl ketone/kg body weight was administered orally to rabbits, 40% was excreted as heptyl-2-glucuronide, and traces of the unchanged ketone were also found in the urine (Kamil, Smith & Williams, 1953). 2-Heptanone (methyl amyl ketone) was identified as being among the approximately 300 compounds present in the volatile constituents of urine from male and female subjects (Zlatkis & Liebich, 1971).

Purification Methods

Dry 4-pentanone with CaSO4, then distil it from P2O5 under nitrogen. [Beilstein 1 IV 3323.]

Waste Disposal

DPK is burned in a chemical incineratorequipped with an afterburner and scrubber.

InChI:InChI=1/C7H14O/c1-3-5-7(8)6-4-2/h3-6H2,1-2H3

Upstream product

• 106-31-0 butanoic acid anhydride 
• 74-85-1 ethene 
• 589-55-9 heptan-4-ol 
• 2586-89-2 hept-3-yne 
• 628-71-7 1-Heptyne 
• 78-09-1 orthocarbonic acid tetraethyl ester 
• 927-77-5 n-propylmagnesium bromide 
• 496-03-7 2-ethyl-3-hydroxyhexanal 
• 5699-74-1 2-hydroxy-2-propyl-valeronitrile 
• 690633-38-6 1-methoxy-5-propyl-oct-4-en-3-one 
• 920-39-8 isopropylmagnesium bromide 
• 156-54-7 sodium butyrate 
• 15719-64-9 methylammonium carbonate 
• 5743-36-2 calcium dibutyrate 

Downstream Products

• 6632-94-6 4-propyloctan-4-ol 
• 17302-13-5 4-Propyl-octan 
• 6324-55-6 4,7-dipropyl-dec-5-yne-4,7-diol 
• 58343-21-8 3-phenylheptan-4-one 
• 589-55-9 heptan-4-ol 
• 51200-82-9 4-isopropyl-heptan-4-ol 
• 187737-37-7 propene 
• 2198-72-3 4-propylheptan-4-ol 
• 62108-07-0 4-hydroxy-4-propyl-1-heptene 
• 5699-74-1 2-hydroxy-2-propyl-valeronitrile 
• 438-25-5 3-ethyl-1,1,1-trifluoro-heptane-2,4-dione 
• 74-85-1 ethene 
• 107-87-9 2-Pentanone 
• 74-98-6 propane 

Related news

Catalysed synthesis of 4-Heptanone (cas 123-19-3) from 1-butanol09/07/2019

While investigating the reaction of 1-butanol over base catalysts, such as MgO, we observed the formation of small amounts of 4-heptanone. Further studies revealed that a CeO2/MgO catalyst gave good selectivity to this product. To optimise the reaction and determine the reaction mechanism a seri...detailed

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