ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Carboxylic acid esters and derivatives > Butyl acetate
Butyl acetate Chemical Properties
- Melting point:−78 °C(lit.)
- Boiling point:124-126 °C(lit.)
- Density 0.88 g/mL at 25 °C(lit.)
- vapor density 4 (vs air)
- vapor pressure 15 mm Hg ( 25 °C)
- refractive index n
- FEMA 2174 | BUTYL ACETATE
- Flash point:74 °F
- storage temp. Flammables area
- solubility 5.3g/l
- form Liquid
- color ≤10(APHA)
- Specific Gravity0.883 (20/20℃)
- PH6.2 (5.3g/l, H2O, 20℃)(External MSDS)
- OdorCharacteristic; agreeable fruity (in low concentrations); non residual.
- Odor Threshold0.016ppm
- explosive limit1.4-7.5%(V)
- Water Solubility 0.7 g/100 mL (20 ºC)
- FreezingPoint -77.9℃
- λmaxλ: 254 nm Amax: 1.0
λ: 260 nm Amax: 0.20
λ: 275 nm Amax: 0.04
λ: 300 nm Amax: 0.02
λ: 320-400 nm Amax: 0.01
- JECFA Number127
- Merck 14,1535
- BRN 1741921
- Henry's Law Constant5.79 at 37 °C (static headspace-GC, van Ruth et al., 2001)
- Exposure limitsTLV-TWA 150 ppm (～710 mg/m3) (ACGIH, MSHA, and OSHA); TLV-STEL 200 ppm (～950 mg/m3); IDLH 10,000 ppm (NIOSH).
- Stability:Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, strong bases.
- CAS DataBase Reference123-86-4(CAS DataBase Reference)
- NIST Chemistry ReferenceAcetic acid, butyl ester(123-86-4)
- EPA Substance Registry Systemn-Butyl acetate (123-86-4)
- Risk Statements 10-66-67-R67-R66-R10
- Safety Statements 25-S25
- RIDADR UN 1123 3/PG 3
- WGK Germany 1
- RTECS AF7350000
- Autoignition Temperature790 °F
- TSCA Yes
- HS Code 2915 33 00
- HazardClass 3
- PackingGroup III
- Hazardous Substances Data123-86-4(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 14.13 g/kg (Smyth)
Butyl acetate Usage And Synthesis
- UsesSolvent for nitrocellulose, oils, fats, resins, waxes, and camphor; manufacture of lacquer and plastics
- Descriptionn-Butyl acetate, also known as Butyl acetate, is an organic compound commonly used as a solvent in the production of lacquers and other products. It is also used as a synthetic fruit flavoring in foods such as candy, ice cream, cheeses, and baked goods. Butyl acetate is found in many types of fruit, where along with other chemicals it imparts characteristic flavors. apples, especially of the Red Delicious variety, are fl avored in part by this chemical. It is a colorless flammable liquid with a sweet smell of banana.
Butyl acetate is a clear, flammable ester of acetic acid that occurs in n-, sec-, and tert- forms (INCHEM, 2005). Butyl acetate isomers have a fruity, banana-like odor (Furia, 1980). Isomers of butyl acetate are found in apples (Nicholas, 1973) and other fruits (Bisesi, 1994), as a well as in a number of food products, such as cheese, coffee, beer, roasted nuts, vinegar (Maarse and Visscher, 1989). Butyl acetate is manufactured via esterification of the respective alcohol with acetic acid or acetic anhydride (Bisesi, 1994). N-butyl acetate is used as a solvent for nitrocellulose-based lacquers, inks, and adhesives. Other uses include manufacture of artificial leathers, photographic film, safety glass, and plastics (Budavari, 1996). Isomers of butyl acetate are also used as flavoring agents, in manicure products, and as larvicides (Bisesi, 1994). The tert-isomer has been used as a gasoline additive (Budavari, 1996). It may be used as a synthetic fruit flavoring in candy, ice cream, cheeses, and baked goods (Dikshith, 2013).
- Chemical PropertiesButyl acetate is a colorless or yellowish liquid with a strong fruity odor. burning and then sweet taste reminiscent of pineapple. It occurs in many fruits and is a constituent of apple aromas. Butyl acetate is incompatible with strong oxidizing agents, strong acids, and strong bases.
There are 4 isomers. At 20 °C, the density of the n-butyl isomer is 0.8825 g/ cm3, and the density of the sec-isomer is 0.8758 g/cm3 (Bisesi, 1994). The n-butyl isomer is soluble in most hydrocarbons and acetone, and it is miscible with ethanol, ethyl ether, and chloroform (Haynes, 2010). It dissolves many plastics and resins (NIOSH, 1981).
- Physical propertiesClear, colorless liquid with a strong fruity odor resembling bananas. Sweetish taste as low concentrations (<30 μg/L). Experimentally determined detection and recognition odor threshold concentrations were 30 μg/m3 (6.3 ppbv) and 18 μg/m3 (38 ppbv), respectively (Hellman and Small, 1974). Cometto-Mu?iz et al. (2000) reported nasal pungency threshold concentrations ranged from approximately 550 to 3,500 ppm.
- OccurrenceReported present in rum ether, pears, pear brandy, cider, mango, mountain papaya (C. pubescens), soybean, roasted peanuts and honey and other natural products.
- Usesn-Butyl acetate is used in the manufactureof lacquers, plastics, photographic films, andartificial leathers.
- UsesButyl acetate is one of the more important derivatives of n-butyl alcohol produced commercially, is employed as a solvent in rapid drying paints and coatings. In some instances, butyl acetate, C6H12O2, has replaced ethoxyethyl acetate due to the latter’s reported toxicity and teratogenicity.
- UsesButyl Acetate is a flavoring agent which is a clear, colorless liquid possessing a fruity and strong odor. it is sparingly soluble in water and miscible in alcohol, ether, and propylene glycol. it is also termed n-butyl acetate.
- DefinitionChEBI: The acetate ester of butanol.
- Production MethodsButyl alcohol is combined with acetic acid in the presence of a catalyst such as sulfuric acid. After esterification is complete, the solution is distilled to yield butyl acetate .
- PreparationBy esterification of n-butyl alcohol with acetic acid.
- Aroma threshold valuesDetection: 10 to 500 ppb
- Synthesis Reference(s)Journal of the American Chemical Society, 73, p. 5265, 1951 DOI: 10.1021/ja01155a075
The Journal of Organic Chemistry, 39, p. 3728, 1974 DOI: 10.1021/jo00939a026
- General DescriptionA clear colorless liquid with a fruity odor. Flash point 72 - 88°F. Density 7.4 lb / gal (less than water). Hence floats on water. Vapors heavier than air.
- Air & Water ReactionsHighly flammable. Very slightly soluble in water.
- Reactivity ProfileButyl 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. Attacks many plastics. [Handling Chemicals Safely 1980. p. 233].
- HazardSkin irritant, toxic. Flammable, moderate fire risk. Eye and upper respiratory tract irritant.
- Health HazardExposures to n-butyl acetate cause harmful effects that include, but are not limited to, coughing and shortness of breath. High concentrations have a narcotic effect, with symp toms such as sore throat, abdominal pain, nausea, vomiting, and diarrhea. High concen trations of n-butyl acetate cause severe poisoning. Prolonged periods of exposure cause adverse effects to the lungs, the nervous system, and the mucous membranes. Repeated skin contact causes skin dryness or cracking, and dermatitis.
- Health HazardThe narcotic effects of n-butyl acetate isgreater than the lower alkyl esters of aceticacid. Also, the toxicities and irritant actionsare somewhat greater than n-propyl, iso propyl, and ethyl acetates. Exposure to its vapors at about 2000 ppm caused mild irritation of the eyes and salivation in test animals. A 4-hour exposure to 14,000 ppm wasfatal to guinea pigs. In humans, inhalation of 300-400 ppm of n-butyl acetate may produce moderate irritation of the eyes and throat, and headache.
- Fire HazardHIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Safety ProfileModerately toxic by intraperitoneal route. Mdly toxic by inhalation and ingestion. An experimental teratogen. A skin and severe eye irritant. Human systemic effects by inhalation: conjunctiva irritation, unspecified nasal and respiratory system effects. A mild allergen. High concentrations are irritating to eyes and respiratory tract and cause narcosis. Evidence of chronic systemic toxicity is inconclusive. Flammable liquid. Moderately explosive when exposed to flame. Ignites on contact with potassium tert-butoxide. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid and irritating fumes. See also ESTERS.
- Potential Exposuren-Butyl acetate is an important solvent in the production of lacquers, leather and airplane dopes, and perfumes. It is used as a solvent and gasoline additive. sec-Butyl acetate is used as a widely used solvent for nitrocellulose, nail enamels and many different purposes. tert-Butyl acetate is common industrial solvent used in the making of lacquers, artificial leather, airplane dope, perfume; and as a food additive. Isobutyl acetate is used as a solvent and in perfumes and artificial flavoring materials
- CarcinogenicityThere are no indications of mutagenic or cytogenic effects for n-butyl acetate.
- SourceIdentified as a volatile constituent released by fresh coffee beans (Coffea canephora variety Robusta) at different stages of ripeness (Mathieu et al., 1998). Also 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 FateBiological. Heukelekian and Rand (1955) reported a 5-d BOD value of 0.52 g/g which is 23.5%
of the ThOD value of 2.21 g/g.
Photolytic. Butyl acetate reacts with OH radicals in the atmosphere at a rate constant of 4.15 x 10-12 cm3/molecule?sec at 296 K (Wallington et al., 1988b).
Chemical/Physical. Hydrolyzes in water forming 1-butanol and acetic acid. Estimated hydrolysis half-lives at 20 °C: 11.4 d at pH 9.0, 114 d at pH 8.0, and 3.1 yr at pH 7.0 (Mabey and Mill, 1978).
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 154 mg/L. The adsorbability of the carbon was 169 mg/g carbon (Guisti et al., 1974).
- storagen-Butyl acetate should be kept stored in a segregated and approved area. Workers should keep the container in a cool, well-ventilated area, closed tightly, and sealed until ready for use. Workers should avoid all possible sources of ignition/spark at the workplace
- ShippingUN1123 Butyl acetates, Hazard Class: 3; Labels: 3—Flammable liquid.
- Purification MethodsDistil, reflux with successive small portions of KMnO4 until the colour persists, dry with anhydrous CaSO4, filter and redistil. [Beilstein 2 IV 143.]
- IncompatibilitiesAll butyl acetates are incompatible with nitrates, strong oxidizers; strong alkalies; strong acids. Butyl acetates may form explosive mixture with air; reacts with water, on standing, to form acetic acid and n-butyl alcohol. Violent reaction with strong oxidizers and potassium-tert-butoxide. Dissolves rubber, many plastics, resins and some coatings. May accumulate static electrical charges, and may cause ignition of its vapors
- Waste DisposalDissolve 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.
- PrecautionsOn exposure to n-butyl acetate, immediately wash with plenty of water, also under the eyelids, for at least 15 min. Remove contact lenses. n-Butyl acetate is flammable in the pres ence of open flames, sparks, oxidizing materials, acids, and alkalis. It poses explosion risk in the presence of mechanical impact. For health safety, management authorities should provide exhaust ventilation facilities at the workplace to keep the airborne concentrations of vapors of n-butyl acetate below TLV
Butyl acetate Preparation Products And Raw materials
- Raw materialsEtanolAcetic acid glacialSodium carbonate1-ButanolFatty acid (C10～C20)
- Preparation ProductsAcetyl ketenePAINTPolyurethane foamsMETHANEErythromycin4-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE4-Nitrophenyl-beta-D-galactopyranoside4-NITROPHENYL-ALPHA-D-GALACTOPYRANOSIDETOLUENE DIISOCYANATEPotassium benzylpenicillinPenicillin G sodium salt4-NITROPHENYL-ALPHA-D-GLUCOPYRANOSIDEAcesulfamecomplex polystyrene high efficiency anticorrosion paintleather seasoning agent DLC-12-METHOXY-6-METHYL-4(1H)-PYRIMIDINONEThyminescavenger of fabric maculaeCephalothinACETOACETIC ACID N-BUTYL ESTEROXACILLIN SODIUMAnethole trithioneSineptinaseasoning agent GS-1modified polyurethane seasoning agent
- Propyl acetate Methyl acetate ISOPULEGYL ACETATE Potassium Acetate n-Butyl cyanoacetate Butyl 2-chloroacetate #niso-Butyl acetate,#niso-Butyl acetate 3-METHOXY-1-BUTYL ACETATE,3-METHOXY-1-BUTYL ACETATE Ethyl acetate tert-Butyl peroxyacetate Butyl acetate Glatiramer acetate SEC-BUTYL ACETATE 98%,DL-SEC-BUTYL ACETATE,DL-SEC-BUTYL ACETATE,SEC-BUTYL ACETATE 98% Vinyl acetate TERT-BUTYL ACETATE, WACKER QUALITY,TERT-BUTYL ACETATE, 99+%,TERT-BUTYL ACETATE, WACKER QUALITY,TERT-BUTYL ACETATE, 99+% tert-Butyl bromoacetate Butyl hydroxyacetate Sodium acetate
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- Nov 18，2019