4-Heptanone Property

Melting point:

-33 °C (lit.)

Boiling point:

145 °C (lit.)

Density 

0.817 g/mL at 25 °C (lit.)

vapor density 

3.94 (vs air)

vapor pressure 

5.2 mm Hg ( 20 °C)

refractive index 

n20/D 1.408(lit.)

FEMA 

2546 | 4-HEPTANONE

Flash point:

120 °F

storage temp. 

Store below +30°C.

solubility 

H2O: insoluble

form 

Liquid

color 

Clear colorless to light yellow

Odor

at 10.00 % in dipropylene glycol. fruity cheese sweet cognac pineapple

Odor Type

fruity

explosive limit

1%(V)

Water Solubility 

4.6 g/L (20 ºC)

Merck 

14,3345

JECFA Number

287

BRN 

1699049

Exposure limits

TLV-TWA 235 mg/m³ (50 ppm) (NIOSH).

Dielectric constant

12.6（17℃）

Stability:

Stable. Flammable. Incompatible with strong oxidizing agents, strong bases, strong reducing agents.

InChIKey

HCFAJYNVAYBARA-UHFFFAOYSA-N

LogP

1.97

CAS DataBase Reference

123-19-3(CAS DataBase Reference)

NIST Chemistry Reference

4-Heptanone(123-19-3)

EPA Substance Registry System

4-Heptanone (123-19-3)

Safety

Hazard Codes 

Xn

Risk Statements 

10-20/22-20-R20-R10-2017/10/20

Safety Statements 

24/25-S24/25

RIDADR 

UN 2710 3/PG 3

OEB

A

OEL

TWA: 50 ppm (235 mg/m3)

WGK Germany 

2

RTECS 

MJ5600000

Autoignition Temperature

430 °C

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29141900

Hazardous Substances Data

123-19-3(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 3021 mg/kg LD50 dermal Rabbit 4585 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

H332Harmful if inhaled

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

4-Heptanone Chemical Properties,Usage,Production

Description

4-Heptanone is an organic ketone containing seven carbon atoms. It can be found in urine samples of human being. It arises from in vivo beta-oxidation of 2-ethylhexanoic acid (EHA) from plasticisers, which is similar to the formation of 3-heptanone from valproic acid. It is mainly used as the solvents of nitrocellulose, nitrocellulose paint and synthetic resin and as the raw materials of organic synthesis. It can also be used as a internal standard of gas chromatography-mass spectrometry for the analysis of 3-monochloro-1, 2-propane diol which is a potential carcinogen found in soy sauce. It can be synthesized during the reaction of 1-butanol over base catalysts such as MgO.

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. Niñonuevo. "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.

Description

4-Heptanone has a penetrating odor and burning taste. It is prepared by passing butyric acid over a wood coal at 425°C and then over cerium oxide at 500°C or over thorium oxide; also over manganese oxide at 400 - 425°C.

Chemical Properties

4-Heptanone has a penetrating odor and burning taste.

Chemical Properties

4-Heptanone is a colourless liquid. Sp.Gr. 0.82. B.P. 144℃. 0.5% soluble in water, miscible with alcohol and oils. Powerful and diffusive ethereal-fruity, pungent odor, in dilution reminiscent of Pineapple-Strawberry. Fruity, Strawberry type flavor, but not really sweet, and lacks naturalness.

Occurrence

Reported found in apple juice, papaya, pear, cabbage, baked potato, roasted peanut, chicken fat, coffee, bachang (Mangifera foetida L ) and rooibus tea (Aspalathius linearis)

Uses

Solvent for nitrocellulose, oils, resins, and polymers and in flavorings

Uses

4-Heptanone is used as a solvent for nitrocellulose as well as in organic synthesis. It is involved in the preparation of flavorings. It is used as an intermediate in the synthesis of active pharmaceutical ingredients. Further, it is used in paints and coatings.

Uses

Dipropyl ketone (DPK) is used as a solventin oils, resins, nitrocellulose, and polymers;and as a flavoring compound.

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.

Definition

ChEBI: 4-heptanone is a dialkyl ketone that is heptane in which the two methylene protons at position 4 have been replaced by an oxo group. It has a role as a biomarker, a human xenobiotic metabolite, a human urinary metabolite and a rat metabolite. It derives from a hydride of a heptane.

Aroma threshold values

Detection: 8.2 to 41 ppb; aroma characteristics at 1.0%: sweet ethereal, banana fruity, pungent, green apple with cheese nuances.

Taste threshold values

Taste characteristics at 5 ppm: fruity, banana, green apple, blue cheese with nut-like nuances.

Synthesis Reference(s)

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

General Description

A colorless liquid with a pleasant odor. Insoluble in water and less dense than water. Flash point 120°F. Toxic by inhalation. A skin irritant. Used to make flavorings and as a solvent.

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. This compound 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.

Potential Exposure

High or repeated exposures maydamage the liver and kidney. Repeated contact can dry outthe skin, causing irritation and rash.

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).

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with dipropyl ketone you should be trainedon its proper handling and storage. Store in tightly closedcontainers in a cool, well-ventilated area away from oxidizers. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible,automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped withself-closing valves, pressure vacuum bungs, and flamearresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames,are prohibited where this chemical is used, handled, orstored in a manner that could create a potential fire orexplosion hazard. Wherever this chemical is used, handled,manufactured, or stored, use explosion-proof electricalequipment and fittings

Shipping

This compound requires a shipping label of“FLAMMABLE LIQUID.” It falls in Hazard Class 3 andPacking Group II.

Purification Methods

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

Incompatibilities

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, getmedical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

Waste Disposal

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