Hexanoic acid Chemical Properties

Melting point:

-4 °C (lit.)

Boiling point:

202-203 °C (lit.)

Density 

0.927 g/mL at 25 °C (lit.)

vapor density 

4 (vs air)

vapor pressure 

0.18 mm Hg ( 20 °C)

FEMA 

2559 | HEXANOIC ACID

refractive index 

n20/D 1.4161(lit.)

Flash point:

220 °F

storage temp. 

Store below +30°C.

solubility 

water: slightly soluble1.082g/100g(lit.)

form 

Liquid

pka

4.85(at 25℃)

Specific Gravity

0.929 (20/4℃)

color 

Clear colorless to light yellow

PH

4 (1g/l, H2O, 20℃)

Odor Threshold

0.0006ppm

Water Solubility 

1.1 g/100 mL (20 ºC)

JECFA Number

93

Merck 

14,1759

BRN 

773837

Stability:

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

InChIKey

FUZZWVXGSFPDMH-UHFFFAOYSA-N

CAS DataBase Reference

142-62-1(CAS DataBase Reference)

NIST Chemistry Reference

Hexanoic acid(142-62-1)

EPA Substance Registry System

Hexanoic acid (142-62-1)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-21-20/21/22

Safety Statements 

26-36/37/39-45-25

RIDADR 

UN 2829 8/PG 3

WGK Germany 

1

RTECS 

MO5250000

F 

13

Autoignition Temperature

380 °C

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29159000

Hazardous Substances Data

142-62-1(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 3.0 g/kg (Smyth, Carpenter)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Hexanoic acid Usage And Synthesis

Description

Hexanoic acid (also known as Caproci acid, general formula: C5H11COOH) belongs to a kind of saturated medium-chain fatty acid derived from hexane with an unpleasant odor. It is a colorless oily liquid naturally existing in various plant and animal fats and oils. One of its major applications is for the manufacturing of its esters for being artificial flavors. It is also important for the manufacturing of hexyl derivatives such as hexylphenols. Hexanoic acid belongs to medium chain triglycerides (MCT) that are widely used as a nutrition supplement that added to foods, drugs and cosmetics.

References

https://pubchem.ncbi.nlm.nih.gov/compound/hexanoic_acid#section=Toxicological-Information
https://en.wikipedia.org/wiki/Hexanoic_acid

Description

Hexanoic acid (caproic acid), is the carboxylic acid derived from hexane with the general formula C₅H₁₁COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that give the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. The primary use of hexanoic acid is in the manufacture of its esters for artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.
The salts and esters of this acid are known as hexanoates or caproates.
Two other acids are named after goats: caprylic (C8) and capric (C10). Along with hexanoic acid, these total 15% in goat milk fat. Caproic, caprylic, and capric acids (capric is a crystal- or waxlike substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.

Chemical Properties

Hexanoic acid has an unpleasant odor reminiscent of copra oil and it exhibits an acrid taste. Hexanoic acid may be prepared by fractionation of the volatile fatty acids of coconut oil.

Chemical Properties

Hexanoic acid has a sickening, sweaty, rancid, sour, sharp, pungent, cheesy, fatty, unpleasant odor reminiscent of copra oil. It exhibits an acrid taste

Chemical Properties

colourless liquid

Occurrence

A secondary product of butyric fermentation; reported found in the essential oils of lavender, camphor, palmarosa, lemongrass and Juniperus phoenicea; in a few fruital aromas: apple, currant and strawberry; also identified among the constituents of petitgrain lime oil. Also reported found in apple, lemon and orange juice, berries, guava, raisin, papaya, peach, pineapple, cooked potato, pepper, breads, cheeses, butter, milk, fish, meats, hop oil, beer, whiskies, rum, brandy, grape wines, coffee, cocoa, tea, filberts, pecans, peanut oil, coconut meat and oil, soybeans, passion fruit, beans, mushrooms, rice, licorice, corn oil, malt, loquat, sherry, clams, mussels, scallops and other sources

Uses

CAPROIC ACID is oily, colorless or slightly yellow, and liquid at room temperature. Odor is that of Limburger cheese. Soluble in alcohol and ether; slightly soluble in water. Caproic acid is derived from the crude fermentation of butyric acid; or by fractional distillation of natural fatty acids. Used in various flavorings; manufacture of rubber chemicals; varnish dryers; resins; pharmaceuticals.

Uses

Intermediates of Liquid Crystals

Uses

manufacture of esters for artificial flavors, and of hexyl derivatives, especially hexylphenols, hexylresorcinol, etc.

Definition

ChEBI: A C6, straight-chain saturated fatty acid.

Definition

An oily carboxylic acid found (as glycerides) in cow’s milk and some vegetable oils.

Preparation

By fractionation of the volatile fatty acids of coconut oil

Aroma threshold values

Detection: 93 ppb to 10 ppm

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 3184, 1977 DOI: 10.1021/ja00451a064
The Journal of Organic Chemistry, 57, p. 6173, 1992 DOI: 10.1021/jo00049a024
Tetrahedron Letters, 11, p. 2679, 1970

General Description

A white crystalline solid or colorless to light yellow solution with an unpleasant odor. Insoluble to slightly soluble in water and less dense than water. Contact may severely irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Used to make perfumes.

Air & Water Reactions

Slightly water soluble.

Reactivity Profile

Hexanoic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Hexanoic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. Hexanoic acid reacts with bases, oxidizing agents and reducing agents.

Hazard

Strong irritant to tissue.

Health Hazard

Harmful if swallowed, inhaled, or absorbed through skin. Material is extremely destructive to tissue of mucous membranes and upper respiratory tract, eyes and skin. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchia, chemical pneumonitis and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting.

Fire Hazard

Special Hazards of Combustion Products: Irritating vapor may be generated.

Purification Methods

Dry the acid with MgSO4 and fractionally distil it from CaSO4. [Beilstein 2 IV 917.]

Hexanoic acid(142-62-1)Related Product Information

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• 1-Hexanol
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• 7-CHLOROCARBONYL-HEPTANOIC ACID ETHYL ESTER
• METHYL O-METHYLPODOCARPATE
• D-(+)-Camphoric acid
• CYCLOPENTYLACETIC ACID
• Ethyl 2-bromoheptanoate
• PINONIC ACID
• 1,2,3,4-CYCLOPENTANETETRACARBOXYLIC ACID
• Cycloleucine
• 1-Phenylcyclopentanecarboxylic acid
• ALPHA-PHENYLCYCLOPENTANEACETIC ACID
• 6-Aminocaproic acid
• Stearic acid
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