Isoamyl acetate Chemical Properties

Melting point:

-78 °C (lit.)

Boiling point:

142 °C/756 mmHg (lit.)

Density 

0.876 g/mL at 25 °C (lit.)

vapor density 

4.5 (vs air)

vapor pressure 

5 mm Hg ( 25 °C)

refractive index 

n20/D 1.4(lit.)

FEMA 

2055 | ISOAMYL ACETATE

Flash point:

77 °F

storage temp. 

Store at +5°C to +30°C.

solubility 

ethanol: soluble1ml/3ml, clear, colorless (60%ethanol)

color 

Clear Colorless

Odor

Banana-like odor

Odor Type

fruity

explosive limit

1-10%(V)

Water Solubility 

0.20 g/100 mL. Slightly soluble

JECFA Number

43

Merck 

14,5111

BRN 

1744750

Henry's Law Constant

10.25 at 37 °C (static headspace-GC, Bylaite et al., 2004)

Exposure limits

TLV-TWA 100 ppm (～530 mg/m³) (ACGIH, MSHA, and OSHA); TLV-STEL 125 ppm (～655 mg/m³); IDLH 3000 ppm (NIOSH).

Dielectric constant

5.6（20℃）

LogP

2.7 at 35℃

CAS DataBase Reference

123-92-2(CAS DataBase Reference)

NIST Chemistry Reference

1-Butanol, 3-methyl-, acetate(123-92-2)

EPA Substance Registry System

Isoamyl acetate (123-92-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-66-36/37/38-R66-R10

Safety Statements 

23-25-2-36/37/39-26-16-S25-S23-S2

RIDADR 

UN 1104 3/PG 3

OEB

A

OEL

TWA: 100 ppm (525 mg/m3)

WGK Germany 

1

RTECS 

NS9800000

Autoignition Temperature

680 °F

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29153900

Hazardous Substances Data

123-92-2(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rat > 5000 mg/kg

IDLA

1,000 ppm

MSDS

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

Isoamyl acetate Usage And Synthesis

Chemical properties

Isoamyl acetate appears as colorless transparent liquid with pleasant banana aroma, being volatile. It is miscible with ethanol, ethyl ether, benzene, carbon disulfide and other organic solvents, being almost insoluble in water.

Uses

1.  It is widely used to configure a variety of fruit flavors, such as Sydney, banana and some other types. There is also some appropriate application in the smoke and daily make-up essence is also appropriate application.
2.  It can be used in the fragrance of heavy flowers such as chypre, sweet-scented osmanthus, hyacinth and heavy oriental flavor, being able to give the fragrance of fresh flower and adjust the fragrance odor with the dosage being often less than 1%. It is also applicable to the smiling flower type. It is also the major spices for the deployment of edible raw pear and banana flavor. It is also used in apple, pineapple, cocoa, cherry, grape, raspberry, strawberry, peach, caramel, cola, cream, coconut and vanilla bean. Also commonly used in wine and tobacco flavor.
3.  Isoamyl acetate is a kind of edible fragrance allowed in China. It can be used to prepare fruit flavors such as strawberry, pineapple, bayberry, pear, apple, grape and banana. The dosage is 2700mg/kg in normal chewing gum. 190 mg/kg in confectionery; 120 mg/kg in pastry; 56 mg/kg in ice cream; 28 mg/kg in soft drinks.
4.  Isoamyl acetate is an important solvent, being able to dissolve nitrocellulose, ester gum, vinyl resin, coumarone resin, rosin, frankincense, dama resin, mountain resin and castor oil. In Japan, 80% of the goods are used as spices, having a strong fruit flavor, like pears, bananas, apples and other fragrance. It is widely used in a variety of edible fruit flavor. In the smoke spice and daily cosmetic spice, there is also appropriate application. It is also used in rayon, dyes, artificial pearls, penicillin extraction and so on.
5.  GB 2760~96 provides it as allowable food flavors. It can also be taken as a solvent, being the major raw material for the preparation of pear and banana flavor. It is commonly used in alcohol and tobacco flavor, also used in the preparation of apples, pineapple, cocoa, cherries, grapes, strawberries, peaches, butter, coconut and other fragrance preparation.
6.  It can be used as chromatographic standard substance, extraction agent and solvent
7.  It can be taken as solvent, for chromium determination, photography, printing and dyeing and the extraction agent of iron, cobalt and nickel.

Production method

Isoamyl acetate is obtained through the esterification between the acetate with the isoamyl alcohol separated from the fusel oil under the catalysis of sulfuric acid.
It is derived from the esterification between acetic acid and isoamyl alcohol. In the mixture of acetic acid and amyl alcohol, add sulfuric acid for esterification reaction, followed by neutralization with sodium carbonate (or caustic soda) with further calcium chloride dehydration to obtain the crude ester, and then refined by distillation to derive the finished products.
Isoamyl acetate is presented in bananas and cocoa beans and is commercially manufactured using pentanol separated from fusel oil as raw materials. Isoamyl alcohol and sulfuric acid have been added to glacial acetic acid for heating reflux reaction. When the temperature of the top of the column reached 132 °C, the esterification was complete. After cooling, wash with water, and neutralize with 10% NaOH solution and then washed with water to neutral, and finally dried with anhydrous calcium chloride after distillation, collecting 138~143 ° C fractions, being the product.
CH3COOH (CH3) 2CHCH2CH2OH [H2SO4] → CH3COOCH2CH2CH (CH3) 2 + H2O

Content analysis

This was determined by the method I in the ester assay (OT-18). The amount of sample taken was 800 mg. The equivalent factor (e) in the calculation is 65.10.
Alternatively, apply the non-polar column in the gas chromatography (GT-10-4) for measurement;

Toxicity

ADI 0 to 3.7 (FAO/WHO, 1994);
LD5016.6 g/kg (rat, oral);

Usage limit

FEMA (mg/kg): soft drinks 28; cold drinks 56; candy 190; baked goods 120; pudding 100; take appropriate amount as limit (FDA § 172.515, 2000);

Hazards & Safety Information

Category: Flammable liquids
Toxicity classification: Low toxicity
Acute Toxicity:  Oral-Rat LD50: 16600 mg/kg
EXPLOSIVES HAZARDOUS CHARACTERISTICS:  it is explosive if its vapors are blended with air
Flammability and Hazardous characteristics:  it is easily flammable with burning releasing irritant smoke
Storage and transportation characteristics:  Treasury: ventilated, low temperature and dry; store and transport it separately from oxidant.
Extinguishing agent:  dry powder, carbon dioxide, foam, mist water
Occupational Standard:  TWA 525 mg/m3; STEL 650 mg/m3

Description

In commercial practice amyl invariably means isoamyl, unless it is prefaced by the n- for normal. Isoamyl acetate has a powerful, fruity odor with a bittersweet taste reminiscent of pear. If impure, the odor is strong, penetrating, and almost shocking. Usually prepared by esterification of commercial isoamyl alcohol with acetic acid.

Chemical Properties

Isoamyl Acetate is a strongly fruity-smelling liquid and has been identified in many fruit aromas. It is the main component of banana aroma and is, therefore, also used in banana flavors.
All isomers of amyl acetate are highly flammable, colorless to yellow, watery liquids.
Isoamyl acetate has a fruity, banana, sweet, fragrant, powerful odor with a bittersweet taste reminiscent of pear. If impure, the odor is strong, penetrating and almost shocking. In commercial practice, amyl invariably means isoamyl.

Physical properties

Clear, colorless liquid with a banana or pear-like odor. Odor threshold concentration is 7 ppm (quoted, Keith and Walters, 1992). A detection odor threshold concentration of 18 μg/m³ (3.4 ppbv) was determined by Katz and Talbert (1930).

Occurrence

Reported to be found in a number of naturally occurring products, including apple, banana, cocoa bean, coffee, cognac, grape, peach, pear, pineapple and strawberry

Uses

In alcohol solution as a pear flavor in mineral waters and syrups; as solvent for old oil colors, for tannins, nitrocellulose, lacquers, celluloid, and camphor; swelling bath sponges; covering unpleasant odors, perfuming shoe polish; manufacture of artificial silk, leather or pearls, photographic films, celluloid cements, waterproof varnishes, bronzing liquids, and metallic paints; dyeing and finishing textiles. A special grade of the amyl acetate has been used for burning in the Hefner lamp serving as a photometric standard.

Uses

banana oil is a carrier oil. The banana family is of more interest for its nutritional value rather than for its botanical properties. The use of plantain juice as an antidote for snake bites has been reported in parts of Southeast Asia since 1916.

Uses

Isoamyl acetate is used to impart pear flavorto mineral waters and syrups, in perfumes, inthe manufacture of artificial silk or leather, inphotographic films, in dyeing textiles, and asa solvent.

Uses

Sting pheromone of the honeybee.1

Definition

ChEBI: The acetate ester of isoamylol.

Preparation

By the esterification of commercial isoamyl alcohol with acetic acid

Production Methods

The commerical-grade isoamyl acetate is prepared by the esterification of amyl alcohol (often fusel oil) with acetic acid and a small amount of sulfuric acid as the catalyst .

Taste threshold values

FEMA PADI: 24.491 mg

General Description

Oily liquid; colorless; banana odor. Floats and mixes with water. Flammable, irritating vapor is produced .

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Isoamyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Isoamyl acetate can react violently with oxidizing materials, nitrates, strong alkalis and strong acids.

Hazard

Flammable, moderate fire risk. Irritant. Explosive limits in air 1–7.5%.

Health Hazard

Isoamyl acetate exhibits low toxicity; thetoxic effects are comparable to those of n amyl acetate. The toxic symptoms includeirritation of the eyes, nose, and throat;fatigue; increased pulse rate; and narcosis.Inhalation of its vapors at 1000 ppm for30 minutes may cause irritation, fatigue, andrespiratory distress in humans. It is more narcotic than are the lower acetic esters. TheLD50 value in rabbits is on the order of7000 mg/kg.

Fire Hazard

FLAMMABLE. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. When heated emits acrid fumes. When exposed to flames can react vigorously with reducing materials.

Flammability and Explosibility

Flammable

Potential Exposure

(n-isomer): Primary irritant (w/o allergic reaction), (sec-isomer) Human Data. Amyl acetates are used as industrial solvents and in the manufacturing and dry-cleaning industry; making artificial fruit-flavoring agents; cements, coated papers, lacquers; in medications as an inflammatory agent; pet repellents, insecticides and miticide. Many other uses.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

Source

Identified among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and Grimm, 2001).

Environmental Fate

Chemical/Physical. Slowly hydrolyzes in water forming 3-methyl-1-butanol and acetic acid.

Shipping

UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Purification Methods

Dry the acetate with finely divided K2CO3 and fractionally distil it. [Beilstein 2 IV 157.]

Incompatibilities

Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrates. May soften certain plastics.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Isoamyl acetate(123-92-2)Related Product Information

• Vinyl acetate
• Ethyl acetate
• Ethyl 2-(Chlorosulfonyl)acetate
• Glatiramer acetate
• Dimethyl succinate
• Tris(trimethylsilyl)phosphate
• Methyl acrylate
• Butyl acetate
• Sodium acetate
• Tocopheryl acetate
• Isoamyl o-hydroxybenzoate
• Isoamyl benzoate
• 3-Methyl-1-butanol
• Isoamyl butyrate
• Methyl acetate
• Potassium Acetate
• Amyl acetate
• Isopropyl acetate
• Isopentyl Ethanoate