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Butyl acetate 123-86-4
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Butyl acetate is a transparent, flammable acetate that exists in normal, secondary, and tertiary configurations (INCHEM, 2005). Butyl acetate isomers have a fruity odor similar to bananas (Furia, 1980). Isomers of butyl acetate are found in apples (Nicholas, 1973) and other fruits (Bisesi, 1994) and in many foods such as cheese, coffee, beer, roasted nuts, vinegar (Maarse and Visscher, 1989). Butyl acetate is produced by esterification of the corresponding alcohol with acetic acid or acetic anhydride (Bisesi, 1994).
| describe | Butyl acetate is a transparent, flammable acetate that exists in normal, secondary, and tertiary configurations (INCHEM, 2005). Butyl acetate isomers have a fruity odor similar to bananas (Furia, 1980). Isomers of butyl acetate are found in apples (Nicholas, 1973) and other fruits (Bisesi, 1994) and in many foods such as cheese, coffee, beer, roasted nuts, vinegar (Maarse and Visscher, 1989). Butyl acetate is produced by esterification of the corresponding alcohol with acetic acid or acetic anhydride (Bisesi, 1994). N-butyl acetate is used as a solvent for lacquers, inks and adhesives. Other uses include the manufacture of artificial leather, photographic film, safety glass and plastics (Budavari, 1996). Isomers of butyl acetate are also used as flavoring agents, nail products and larvicides (Bisesi, 1994). The tertiary isomer has been used as a gasoline additive (Budavari, 1996). It is used as a synthetic fruit flavoring in confectionery, ice cream, cheese and baked goods (Dikshith, 2013). |
| chemical properties | Butyl acetate is a colorless or light yellow liquid with a strong fruity aroma. The burnt sweetness is reminiscent of pineapple. It is found in many fruits and is part of the aroma of apples. Butyl acetate is incompatible with strong oxidizing agents, acids and 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 secondary isomer is 0.8758 g/cm3 (Bisesi, 1994). The n-butyl isomer is soluble in most hydrocarbons and acetone, and is miscible with ethanol, ether, and chloroform (Haynes, 2010). It dissolves many plastics and resins (NIOSH, 1981). |
| physical properties | Transparent, colorless liquid with a strong fruity aroma similar to bananas. Low concentrations ( experimentally determined threshold concentrations for detection and identification of odorants are 30 μg/m 3 (6.3 ppb v ) and 18 μg/m 3 (38 ppb v ) respectively (Hellman and Small, 1974). Comet Muiz et al. (2000) reported a nasal irritant threshold concentration range of approximately 550 to 3,500 ppm. |
| occur | It has been reported in natural products such as rum ether, pears, pear brandy, cider, mango, mountain papaya (C. pubescens), soybeans, roasted peanuts and honey. |
| use | Butyl acetate is one of the more important n-butanol derivatives produced commercially and used as a solvent for fast-drying paints and coatings. In some cases, butyl acetate (C6H12O2) has replaced ethoxyethyl acetate because the latter has been reported to be toxic and teratogenic. |
| use | Butyl Acetate is a flavoring agent, a clear, colorless liquid with a strong fruity odor. Slightly soluble in water, miscible with ethanol, ether and propylene glycol. It is also known as n-butyl acetate. |
| use | n-Butyl acetate is used in the manufacture of varnishes, plastics, photographic film and artificial leather. |
| Prepare | From the esterification of n-butanol and acetic acid. |
| production method | Butanol is mixed with acetic acid in the presence of a catalyst such as sulfuric acid. After the esterification was complete, the solution was distilled to obtain butyl acetate. |
| definition | ChEBI: Butyl acetate is the acetate ester of butanol. It acts as a metabolite. It is functionally related to butan-1-ol. |
| aroma threshold | Detection: 10 to 500 ppb |
| synthetic references | Journal of the American Chemical Society, 73, p. 5265, 1951 DOI: 10.1021/ja01155a075 Journal of Organic Chemistry, 39, p. 3728, 1974 DOI: 10.1021/jo00939a026 |
| general instructions | Transparent colorless liquid with fruity aroma. Flash point 72 - 88°F. Density 7.4 lbs/gal (less than water). So float on the water. Vapor is heavier than air. |
| air and water reaction | Highly flammable. Very slightly soluble in water. |
| reactive profile | Butyl acetate is an ester. The ester reacts with the acid, releasing heat along with the alcohol and acid. Strong oxidizing acids may cause a violent reaction that is sufficiently exothermic to ignite the reaction products. The interaction of the ester with the caustic solution also generates heat. Mixing esters with alkali metals and hydrides produces flammable hydrogen gas. Attacks many plastics. [Safe Handling of Chemicals 1980. 233]. |
| adventure | Irritating to skin, toxic. Flammable with medium fire risk. Irritating to eyes and upper respiratory tract. |
| health hazard | The anesthetic effect of n-butyl acetate is greater than that of lower alkyl acetate. Moreover, its toxicity and irritation are slightly greater than n-propyl acetate, isopropyl acetate and ethyl acetate. Exposure to its vapors at concentrations of approximately 2000 ppm caused mild eye irritation and drooling in test animals. Exposure to concentrations of 14,000 ppm in guinea pigs was fatal in 4 hours. In humans, inhalation of n-butyl acetate at 300-400 ppm may cause moderate eye and throat irritation and headache. |
| health hazard | Exposure to n-butyl acetate can cause harmful effects including, but not limited to, coughing and shortness of breath. High concentrations have narcotic effect, sore throat, abdominal pain, nausea, vomiting, diarrhea and other symptoms. High concentrations of n-butyl acetate can cause severe poisoning. Prolonged exposure can cause adverse effects on the lungs, nervous system and mucous membranes. Repeated skin contact can cause dry or cracked skin, and dermatitis. |
| fire hazard | Highly Flammable: Easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may reach source of ignition and flash back. Most vapors are heavier than air. They spread along the ground and collect in low or confined areas (drains, basements, tanks). Vapor explosion hazard exists indoors, outdoors, or in sewers. Runoff into sewers may present a fire or explosion hazard. Container may explode if heated. Many liquids are lighter than water. |
| Biochemical/Physiological Actions | 30 ppm taste |
| Security overview | The intraperitoneal route is moderately toxic. Moderately toxic by inhalation and ingestion. An experimental teratogen. Severely irritating to skin and eyes. Systemic effects in humans by inhalation: Conjunctival irritation, unspecified nasal and respiratory effects. Mild allergen. High concentrations may irritate eyes and respiratory tract and cause anesthesia. Evidence for chronic systemic toxicity is inconclusive. flammable liquid. Moderately explosive when exposed to flame. Burns on contact with potassium tert-butoxide. When extinguishing fire, please use alcohol foam, carbon dioxide, dry powder. When heated and decomposed, it releases pungent smoke. See also ester. |
| potential contact | n-Butyl acetate is an important solvent in the production of varnishes, leather and aircraft coatings, and perfumes. Used as a solvent and gasoline additive. S-butyl acetate is widely used as a solvent for nitrocellulose, nail polish and many different purposes. Tert-butyl acetate is a common industrial solvent used in the manufacture of varnishes, artificial leather, aircraft coatings, perfumes; and as a food additive. Isobutyl acetate is used as a solvent and as a perfume and artificial fragrance material |
| Carcinogenicity | There is no indication that n-butyl acetate is mutagenic or cytogenic. |
| source | Identified as volatile components released by fresh coffee beans (Coffea canephora cv. Robusta) at different stages of ripening (Mathieu et al., 1998). An automated fast headspace solid-phase microextraction method was also used to identify 139 volatile compounds identified in cantaloupe melo (Cucumis melo var. reticulates cv. Sol Real) (Beaulieu and Grimm, 2001). |
| storage | n-Butyl acetate should be stored in an approved segregated area. Workers should store containers in a cool, well-ventilated area, tightly closed, and sealed until ready for use. Workers should avoid all possible sources of fire/sparks in the workplace |
| Shipping | UN1123 Butyl acetate, hazard level: 3; label: 3—flammable liquid. |
| Purification method | Distill, continuously add small portions of KMnO4 and reflux until the color persists, dry with anhydrous CaSO4, filter and re-distill. [Berstein 2 IV 143. ] |
| Incompatibility | All butyl acetates are incompatible with nitrates, strong oxidants, strong bases, and strong acids. Butyl acetate may form explosive mixtures with air; reacts with water on standing to form acetic acid and n-butanol. Reacts violently with strong oxidizing agents and potassium tert-butoxide. Dissolves rubber, many plastics, resins and some paints. Static electricity may build up and may cause its vapors to ignite |
| waste disposal | The material is dissolved or mixed with a flammable solvent and burned in a chemical incinerator equipped with an afterburner and scrubber. All federal, state and local environmental regulations must be followed. |
| Precautions | After contact with butyl acetate, wash immediately with plenty of water, including under the eyelids, for at least 15 minutes. Remove contact lenses. Butyl acetate is flammable in the presence of open flames, sparks, oxidizing materials, acids and bases. Risk of explosion in case of mechanical shock. For the sake of health and safety, the management department should set up exhaust facilities in the workplace so that the concentration of butyl acetate vapor in the air is lower than the TLV. |
| Butyl acetate upstream and downstream product information |
| raw material | Ethanol --> acetic acid --> sodium carbonate --> 1-butanol --> fatty acid (C10～C20) |
| Preparation products | Acetylketene --> Coating --> Polyurethane foam --> Methane --> Erythromycin --> 4-Nitrophenyl-β-D-Glucopyranoside --> 4-Nitrophenyl- β-D-Galactopyranoside --> 4-Nitrophenyl-ALPHA-D-Galactopyranoside --> Toluene Diisocyanate --> Penicillin G Potassium Salt --> Penicillin G Sodium Salt-- > 4-Nitrophenyl-α-D-glucopyranoside --> Acesulfame K --> Composite polystyrene high-efficiency anticorrosion paint- -> Leather flavoring agent DLC-1 --> 2-METHOXY-6- METHYL-4(1H)-PYRIMIDINONE --> Thymine --> Fabric Spot Remover -->Cefalotin Sodium --> N-Butyl Acetoacetate --> Oxacillin Sodium --> Anethole Trisulfide < ai=43>ketone-->Sineptina --> Flavor GS-1 --> Modified Polyurethane Flavor |
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