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外観
無色～わずかにうすい黄色, 澄明の液体
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性質
プロピオンアルデヒドはやに極めて溶けやすく、水に対しても溶けやすい液体です。プロピオンアルデヒドの融点は-81℃、沸点は47℃で、引火性が高いです。
プロピオンアルデヒドは刺激性が強く、甘酸っぱさの中に焦げたような臭気を持っています。
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溶解性
水に可溶 (20g/100ml水), アルコールに可溶。エタノール及びアセトンに極めて溶けやすく、水に溶けやすい。
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解説
プロピオンアルデヒド,息苦しい臭いの液体．沸点49 ℃．d420"0.8071．nD19"1.3646．引火性がある．亜硫酸水素塩と付加物をつくり，酸化するとプロピオン酸に，還元するとプロピルアルコールになる．アルカリ性溶液中m-ジニトロベンゼンで緑褐色を呈する．
森北出版「化学辞典（第2版）
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用途
トリメチロールエタン原料、香料原料 (SRI: CHEIMICAL ECONOMICS HANDBOOK)
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構造
プロピオンアルデヒドの示性式は、C2H5CHOまたはCH3CH2CHOで、分子量は58.08です。プロピオンアルデヒドはホルミル基を持っているため、還元力によって銀鏡反応を起こします。
また、プロピオンアルデヒドは重合して、過酸化物を生成することもあります。
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合成
1. オキソ法によるプロピオンアルデヒドの合成
金属触媒の存在下でと水素の混合ガスを、ガスに作用させることで、プロピオンアルデヒドが得られます。オキソ法はヒドロホルミル化とも呼ばれていて、工業的にアルデヒドを製造するための重要な方法の一つです。
コバルト錯体やロジウム錯体を用いた場合、反応の活性種はヒドリドカルボニル錯体です。触媒としてコバルトオクタカルボニルを使用した場合のメカニズムは、提唱者の名を取ってヘック・ブレスロウ (英: Heck-Breslow) 機構と呼ばれています。
2. 酸化によるプロピオンアルデヒドの合成
1-プロパノールの脱水素による、プロピオンアルデヒドの合成法が知られています。硫酸酸性条件下で二クロム酸カリウムを用いて、1-プロパノールを酸化すると、プロピオンアルデヒドを得ることが可能です。
その一方で、現在1-プロパノールは、ほとんどプロピオンアルデヒドから作られています。すなわち、エチレンのヒドロホルミル化によって得られたプロピオンアルデヒドをロジウム錯体などの触媒を用いて水素化することで、1-プロパノールを合成しています。
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製造
プロピオンアルデヒド,プロピルアルデヒドともいう．プロピルアルコールを二クロム酸塩で酸化するか，その蒸気を空気とともに銅触媒上に通して酸化すると生成する．工業的には，オキソ合成でエテン，一酸化炭素，および水素から製造される．
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使用上の注意
不活性ガス封入
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説明
Propionaldehyde is a volatile liquid substance which consists of one carbonyl group and its characteristic functional group. The main functional group is an aldehyde which classifies propionaldehyde in the carbonyls. The main trunk of this substance is a short aliphatic chain. The carbonyl group determines, to a large extent, its chemical properties and most importantly its nucleophilic property. Propionaldehyde is readily oxidized if in contact to oxygen and should therefore be stored under inert gases.
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化学的特性
Propionaldehyde has a characteristic sharp and pungent odor similar to acetaldehyde.It undergoes reactions typical for the low molecular weight aldehydes, which, because of the terminal carbonyl group, are very reactive. Contamination or the exposure to elevated temperatures may induce a hazardous polymerization.
Propionaldehyde is a colorless, flammable liquid with a suffocating fruity odor. It is used as Intermediate for the chemical industry, for example for the manufacture of pharmaceuticals, pesticides, perfumes and plastics.
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天然物の起源
Reported found in apple aroma and in the essential oils of camphor, Rosa centifolia, clary sage, Pinus excelsa
and Pinus silverstris. Also reported found in over 100 natural products including apple, banana, sweet cherry, sour cherry, black
currant grapes, melon, pineapple, strawberry, cabbage, carrot, celery, cucumber, garlic, onion, leek, potato, peas, rutabaga, tomato,
Scotch spearmint oil, vinegar, bread and bread preferment, blue cheeses, cheddar cheese, Swiss cheese, butter, milk, cream, boiled
egg, caviar, fatty fish, cooked turkey, beef, pork and chicken, beer, rum, cognac, whiskies, grape wines, coffee, cocoa, tea, roasted
filberts and peanuts, peanut oil, potato chips, pecans, oats, honey, soybeans, Arctic bramble, beans, Bantu beer, plum brandy, cauliflower,
Brussels sprouts, rice, prickly pear, peated malt, clary sage, truffle, krill, oysters, loganberry, Chinese quince and maté.
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使用
Propionaldehyde is produced by the oxo reaction of ethylene with carbon monoxide and hydrogen. n-Propyl alcohol is produced by hydrogenation of propionaldehyde, and propionic acid is made by oxidation of propionaldehyde.
n-Propyl alcohol is used as solvent in printing inks and as an intermediate in the preparation of agricultural chemicals. Propionic acid is used as a grain preservative as, for example, in preventing spoilage of wet corn used as animal feed. The use of propionic acid as a grain preservative is an alterna tive to drying by heating, which consumes fuel, and is considered mostly when fuel is expensive.
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定義
ChEBI: An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.
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製造方法
Propionaldehyde is prepared in the usual way by the oxidation of n-propyl alcohol. It can also be prepared by dehydrogenating the alcohol by passing the vapors over a heated copper or brass catalyst. This avoids the danger of further oxidation to propionic acid.
The reactions of propionaldehyde are practically like those of acetaldehyde. It must be remembered that only the two alpha hydrogen atoms are active in replacement and condensation reactions.
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一般的な説明
A clear colorless liquid with an overpowering fruity-like odor. Less dense than water. Flash point 15°F. Vapors are heavier than air.
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空気と水の反応
Highly flammable. Soluble in water.
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反応プロフィール
Propionaldehyde may form explosive peroxides. Reacts vigorously with oxidizing agents. Explosive in the form of vapor when exposed to heat or flame [Lewis]. Incompatible with strong bases and strong reducing agents. Vigorous polymerization reaction with methyl methacrylate. Polymerization may also occur in the presence of acids or caustics .
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危険性
Flammable, dangerous fire risk, explosive
limits in air 3.0–16%. Upper respiratory tract irri-
tant.
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健康ハザード
Propionaldehyde is a mild irritant to humanskin and eyes. The irritation effect from40 mg was severe in rabbits’ eyes. The toxicityof this compound observed in test animalswas low. Subcutaneous administration in ratsexhibited the symptoms of general anestheticeffect, convulsion, and seizure. Inhalationtoxicity was determined to be low. A concentrationof 8000 ppm (19,000 mg/m3) inair was lethal to rats.
LD50 value, oral (rats): 1400 mg/kg
LD50 subcutaneous (rats): 820 mg/kg.
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火災危険
Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back.
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使用用途
プロピオンアルデヒドは、医薬や樹脂の原料に使用されているほか、香料や香辛料として食品添加物にも利用されています。元々果実といった天然物だけでなく、乳製品や酒類にも存在していることが知られています。香料として加工食品に添加すると、香りや風味をかもし出すことが可能です。それ以外にも、除草剤や農薬といった農業分野に利用されています。
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安全性プロファイル
Moderately toxic by
skin contact, ingestion, and subcutaneous
routes. Mddly toxic by inhalation. A skin
and severe eye irritant. Flammable liquid.
Dangerous fire hazard when exposed to heat
or flame; reacts vigorously with oxidizers.
Explosive in the form of vapor when
exposed to heat or flame. Vigorous
polymerization reaction with methyl
methacrylate. To fight fire, use alcohol
foam, CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ALDEHYDES.
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職業ばく露
Used as a synthetic flavoring; as
a disinfectant and preservative; to make propionic acid;
in plastic and rubber manufacturing; to make alkyl resins
and plasticizers.
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概要
プロピオンアルデヒドとは、無色もしくは僅かにうすい黄色の澄明な液体で、刺激臭のある有機化合物です。
IUPAC命名法では、プロパナール (英: propanal) と表されています。プロピオンアルデヒドのCAS登録番号は123-38-6です。
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発がん性
In a mutagenic test in V79 cells, Eder et al. observed
that propionaldehyde is not mutagenic at 1 mM, but is toxic at 2mM. Similar to acrolein, Eder et al. suggested that
the mutagenicity of this compound is mediated by its bifunctionality,
whereas its cytotoxicity is mediated by the aldehyde
function.
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輸送方法
UN1275 Propionaldehyde, Hazard Class: 3; Labels: 3-Flammable liquid.
Propionaldehyde is readily oxidized if in contact to oxygen and should therefore be stored under inert gases.
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純化方法
the aldehyde with CaSO4 or CaCl2, and fractionally distil it under nitrogen or in the presence of a trace of hydroquinone (to retard oxidation). Blacet and Pitts [J Am Chem Soc 74 3382 1952] repeatedly distilled the middle fraction in a vacuum until it no longer gave a solid polymer when cooled to -80o. It is stored with CaSO4. [Beilstein 1 IV 3165.]
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不和合性
Incompatible with strong acids; amines.
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, oxoa-
cids, epoxides. Strong caustics; reducing agents can cause
explosive polymerization. Can self-ignite if finely dispersed
on porous or combustible material, such as fabric. Heat or
UV light can cause decomposition. Aldehydes are fre-
quently involved in self-condensation or polymerization
reactions. These reactions are exothermic; they are often
catalyzed by acid. Aldehydes are readily oxidized to give
carboxylic acids. Flammable and/or toxic gases are gener-
ated by the combination of aldehydes with azo, diazo com-
pounds, dithiocarbamates, nitrides, and strong reducing
agents. Aldehydes can react with air to give first peroxo
acids, and ultimately carboxylic acids. These autoxidation
reactions are activated by light, catalyzed by salts of
transition metals, and are autocatalytic (catalyzed by the
products of the reaction). The addition of stabilizers (anti-
oxidants) to shipments of aldehydes retards autoxidation
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廃棄物の処理
Propionaldehyde is destroyed by burning in achemical incinerator equipped with an afterburnerand scrubber. Permanganate oxidationis a suitable laboratory method of destruction.
