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Butyl propionate

From Wikipedia, the free encyclopedia
Butyl propionate
Butyl propionate, an ester of butanol and propionic acid
Names
IUPAC name
Butyl propionate
Systematic IUPAC name
Butyl propanoate
Other names
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.791 Edit this at Wikidata
EC Number
  • 209-669-5
RTECS number
  • UE8245000
UN number 1914
  • InChI=1S/C7H14O2/c1-3-5-6-9-7(8)4-2/h3-6H2,1-2H3[1]
    Key: BTMVHUNTONAYDX-UHFFFAOYSA-N
  • CCCCOC(=O)CC
Properties
CH3CH2COO(CH2)3CH3
Molar mass 130.187 g·mol−1
Appearance Colorless liquid
Odor Pear drops, apple, strawberry, earthy, faintly sweet[1]
Density 0.8754 g/cm3[1]
Melting point −89 °C (−128 °F; 184 K)[1]
Boiling point 146.8 °C (296.2 °F; 419.9 K)[1]
1.5 mg/mL at 20 °C (poor)[1]
Solubility Miscible with alcohol, ether[1]
log P 2.314[1]
Vapor pressure 0.589 kPa
0.38 kPa at 20 °C[1]
1.4014
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Very flammable
GHS labelling:
GHS02: Flammable
Warning
H226
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501
Flash point 90 °F (32 °C)[1]
425 °C (797 °F)[1]
Lethal dose or concentration (LD, LC):
  • 5 gm/kg (oral, rat)
  • >14 gm/kg (skin, rabbit)
[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Butyl propionate is a butyl ester of propionic acid. This ester has the chemical formula CH3CH2COO(CH2)3CH3.

Occurrence in nature

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Butyl propionate is a plant metabolite, a human metabolite and an insect attractant. Butyl propionate is a natural ester found in Armenian apricot.[1]

Preparation

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Butyl propionate is derived by esterification of propionic acid with butanol.[1]

CH3CH2COOH + CH3(CH2)3OH ⇌ CH3CH2COO(CH2)3CH3 + H2O

Properties

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Butyl propionate is a colorless liquid with a pear drops-like or apple-like odor. The liquid is less dense than water. Its vapor is 4.5 times denser than the air at the mean ocean level.[1]

Uses

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Butyl propionate is used to make fragrances, perfumes and as a flavoring. It is also used in paints and primers for auto body or engine, appliance coatings (paints designed specifically for painting household items and vehicles like microwave ovens, refrigerators and automobiles), enamels, lacquers, and printing inks, as a solvent for adhesives and nitrocellulose, and in polymerization reactions for acrylic resins.[1]

Hazards and toxicity

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Butyl propionate may irritate skin and eyes. Exposure to its vapor may cause eye and respiratory system irritation. Upon ingestion, causes abdominal pain and nausea. This chemical is very flammable. It may ignite even at ambient temperatures. Above 32 °C (90 °F), explosive mixtures with air may be formed. Strong oxidizing acids may cause a violent reaction that is sufficiently exothermic to ignite this chemical and the reaction products. Upon catching a fire, irritating, toxic and suffocating gases may be produced, such as carbon dioxide and carbon monoxide.[1]

References

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  1. ^ a b c d e f g h i j k l m n o p q "Butyl propionate".