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外観
無色澄明の液体
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溶解性
水に可溶 (11g/100g水, 18℃), アルコール, エーテル易溶。エタノール及びアセトンに極めて溶けやすく、水にやや溶けやすい。
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解説
C3H6O2(74.08)．HCOOC2H5．ギ酸エチルは，濃硫酸の存在下，ギ酸をエタノールでエステル化すると得られる．無色の液体．沸点54 ℃．d2040.917．n20D1.359．水，エタノール，有機溶媒に可溶．加水分解，引火(引火点－28 ℃)しやすいので，乾燥剤を入れて冷暗所に保存する．ホルミル化剤，殺菌，殺虫剤，フレーバーとして使われる．森北出版「化学辞典（第2版）
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用途
香味料原料、医薬品原料
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用途
フレーバーとしての用途は広くピーチ、パイナップル、アップル、アプリコット、バナナ、ベリー、バター、ブランデー、ラムウイスキーに用いる
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説明
Ethyl formate is an ester formed when ethanol (an alcohol) reacts with formic acid (a carboxylic acid). It is also known as ethyl methanoate because formic acid is also known as methanoic acid. Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries.
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物理的性質
Colorless and transparent liquid, volatile, with a pleasant, fruity odor. Miscible with ethanol and ether, soluble in acetone. The solubility in water is 11.8g/100ml.
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天然物の起源
Reported in the oil of Boronia dentigeroides; it has been identified in Florida orange juice, several varieties of
honey, apple and pear and in distilled liquors, such as rum. Also reported found in peach, raspberry, strawberry, pineapple, cabbage,
vinegar, cheeses, butter, cream, milk powder, cooked beef, beer, coffee, tea, honey, corn oil, brandy and mussels.
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使用
Ethyl Formate is a flavoring agent that occurs naturally in some plant oils, fruits, and juices but does not occur naturally in the ani- mal kingdom. it is used in food at a maximum level, as served, of 0.05% in baked goods; 0.04% in chewing gum, hard candy, and soft candy; 0.02% in frozen dairy desserts; 0.03% in gelatins, puddings, and fillings; and 0.01% in all other food categories.
Ethyl formate is also used as a solvent for nitrocellulose; as fungicide and larvicide for tobacco, cereals, dried fruits, etc.; in organic synthesis.
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製造方法
Ethyl Formate is an ester of formic acid and is prepared by esterification of formic acid with ethyl alcohol or by distillation of ethyl acetate and formic acid in the presence of concentrated sulfuric acid.
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定義
ChEBI: Ethyl formate is a formate ester resulting from the formal condensation of formic acid with ethanol. It has a role as a fumigant and a plant metabolite. It is a formate ester and an ethyl ester.
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一般的な説明
A clear colorless liquid with a pleasant odor. Flash point -4°F. Less dense than water. Vapors heavier than air.
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空気と水の反応
Highly flammable. Soluble in water. Slowly decomposed by water to formic acid, a corrosive material and ethyl alcohol, another flammable liquid.
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反応プロフィール
Ethyl formate 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. Ethyl formate is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids [Note: Decomposes slowly in water to form ethyl alcohol and formic acid.] .
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健康ハザード
The irritant action of ethyl formate inthe eyes, nose, and mucous membranes ismilder than that of methyl formate. How ever it is more narcotic than the methylester. Cats exposed to 10,000 ppm died after90 minutes, after deep narcosis. A 4-hourexposure to 8000 ppm was lethal to rats.Inhalation of 5000 ppm for a short periodproduces eye and nasal irritation and salivation in rats. The toxic effects from ingestion include somnolence, narcosis, gastritis,and dyspnea. The oral LD50 values in various test animals range between 1000 and2000 mg/kg.
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火災危険
Highly flammable liquid. Vapor is heavier than air and may travel long distance to a source of ignition and flash back. A very dangerous fire and explosion hazard when exposed to heat, flame, or oxilzers. To fight fire, use alcohol foam, spray, mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.
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使用用途
ギ酸エチルは、パイナップルなどの果実系香料やウィスキー、ラム酒、ブランデーなどの洋酒のフレーバーとして、様々な用途で用いられています。純粋なギ酸エチルのみを高濃度で嗅うぐ、スーッとするや除光液のような匂いに感じます。
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安全性情報
ギ酸エチルの液体や蒸気には引火性があります。また、目や呼吸器に刺激を与える恐れがあります。消防法で「 第4類引火性液体」に、労働安全衛生法で「危険物・引火性の物」にそれぞれ指定されており、取り扱いには注意が必要です。
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农业用途
Plant volatiles such as ethyl formate have been shown to have insecticidal properties as fumigant. The efficacy of ethyl formate against insect pests of food commodities, bagged cereals, spices, pulses, dry fruits and oilcakes had been proved. The fumigant was known to provide a high mortality of mixed stage cultures of the key stored product pests, with limited efficacy against the pupal stage of few pests like S. oryzae. The advantages of ethyl formate include natural occurrence in food; rapid kill of insects (2-4 hours); fast breakdown of residues to natural products and low human toxicity. However the fumigant exhibits poor penetration characteristics and high doses (>120 g/t of grain) were required to control internal feeders, which was higher than the flammable limit of 85 g/t. Formulations of ethyl formate in liquid carbon dioxide were found to overcome the problems of flammability and poor penetration.
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安全性
Ethyl methanoate is generally recognized as safe by the U.S. Food and Drug Administration.
According to the U.S Occupational Safety and Health Administration (OSHA), ethyl formate can irritate eyes, skin, mucous membranes, and the respiratory system of humans and other animals; it is also a central nervous system depressant.
Moderately toxic by ingestion and subcutaneous routes. Mddly toxic by skin contact and inhalation. A powerful inhalation irritant in humans. A skin and eye irritant. Questionable carcinogen with experimental tumorigenic data.
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職業ばく露
In industry, Ethyl formate is used as a solvent for cellulose nitrate, cellulose acetate, oils, and greases. It can be used as a substitute for acetone; workers may also be exposed to it under the following circumstances:
during spray, brush, or dip applications of lacquers
during the manufacture of safety glass
When fumigating tobacco, cereals, and dried fruits (as an alternative to methyl bromide under the U.S. Department of Agriculture quarantine system).
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製造方法
図3. ギ酸エチルの製造
ギ酸とエタノールを混合し、触媒を加えるとエステル化によってギ酸エチルが生成します。触媒としては濃硫酸などの強酸が用いられます。この反応ではからのH+が触媒として働くと同時に、生成する水が濃硫酸と水和して反応系から排除されるので、下の図の平衡がより右に移動します。
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環境運命予測
Photolytic. Reported rate constants for the reaction of ethyl formate and OH radicals in the
atmosphere (296 K) and aqueous solution are 1.02 x 10-11 and 6.5 x 10-13 cm3/molecule?sec,
respectively (Wallington et al., 1988b).
Chemical/Physical. Slowly hydrolyzes in water forming ethanol and formic acid (Windholz et
al., 1983).
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輸送方法
UN1190 Ethyl formate, Hazard Class: 3; Labels:
3-Flammable liquid
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純化方法
Free acid or alcohol is removed by standing the ester over anhydrous K2CO3, with occasional shaking, then decanting and distilling from P2O5. Alternatively, the ester can be kept over CaH2 for several days, then distilled from fresh CaH2. It cannot be dried with CaCl2 because it reacts rapidly with the ester to form a crystalline compound. [Beilstein 2 IV 23.]
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不和合性
May form explosive mixture with air.
Reacts violently with nitrates, strong oxidizers, strong
alkalis, and strong acids. Decomposes slowly in water,
forming ethyl alcohol and formic acid. May accumulate
static electrical charges, and may cause ignition of its
vapors
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廃棄物の処理
Spray into a furnace in
admixture with a flammable solvent
