1-オクタノール

外観

無色澄明の液体

定義

本品は、次の化学式で表される脂肪族アルコールである。

性質

1-オクタノールの示性式はCH₃(CH₂)₆CH₂OHで表されます。融点は-16°Cで、沸点は195°Cです。バラのような香りを有し、粘性の高い無色の液体で、水には溶けません。

溶解性

水に難溶, アルコール, エーテルに可溶。エタノール及びジエチルエーテルに極めて溶けやすく、水に極めて溶けにくい。

解説

C8H18O(130.23)．オクタノールともいう．炭素数8の脂肪族飽和アルコールの総称であるが，工業的にはとくに2-エチル-1-ヘキサノールをさすことがある．【Ⅰ】1-オクタノール：CH3(CH2)6CH2OH．動物油脂中などに酢酸，酪酸エステルとして，またフーゼル油中に存在する．カプロン酸エステルの還元によって得られる．融点－15 ℃，沸点195.28 ℃．d²⁰₄ 0.8256．[CAS 111-87-5]【Ⅱ】2-オクタノール：CH3(CH2)5CH(OH)CH3．光学異性体を有し，ラセミ体はフーゼル油中に存在する．融点 －31 ℃，沸点179.0 ℃．d²⁵₄ 0.8168．水に難溶，エタノール，ジエチルエーテルに可溶．溶剤，香料に用いられる．[CAS 123-96-6]
森北出版「化学辞典（第2版）

用途

香料(ローズ系)、化粧品溶剤、 印刷インキ溶剤、可塑剤、安定剤、潤滑油、界面活性剤の原料。

用途

溶剤、香料調合材料、有機合成原料。

製造法

化学式 C8H17OH 。 89種の異性体が可能である。そのうち1-オクタノールはバラのような香りをもつ沸点 195℃の液体。アセチレンからアセトアルデヒド，アルドールを経て製造される。オレフィンと一酸化炭素，水素からオキソ反応によるか，またチーグラー触媒による重合によっても製造される。フタル酸と2-エチルヘキサノールとのエステルはポリ塩化ビニルなどの高分子物質の可塑剤として重要である。塗料や合成潤滑油の原料でもある。

用途

溶剤、香料調合材料、有機合成原料、可塑剤(DOP)の原料。

構造

1-オクタノールのモル質量は130.23g/molで、密度は0.824g/cm³です。別称として、n-オクタノール、オクタン-1-オール、n-カプリルアルコール、n-オクチルアルコール、オクチリン、シポールL8、アルホール8などがあります。

化粧品の成分用途

香料

合成法

工業的に1-オクタノールは、トリエチルアルミニウムを使用してエチレンをオリゴマー化し、アルキルアルミニウム生成物の酸化によって合成可能です。チーグラー法 (英: Ziegler process) と呼ばれ、さまざまなアルコールが生成します。

パラジウム錯体を触媒に用いると、1,3-ブタジエンに1分子の水が付加して二量化します。得られた二重不飽和アルコールを水素化すると、1-オクタノールを生成可能です。

説明

1-Octanol (111-87-5) is a colorless and transparent liquid with the chemical formula C8H18O. It is a fatty alcohol consisting of a linear, saturated chain of eight carbon atoms. Although 1-Octanol is not highly soluble in water, it can dissolve easily in alcohol, ether, and chloroform. This compound is commonly used as a raw material in the production of fragrances, octanal, octanoic acid, and its esters. It also functions as a solvent, defoamer, and lubricating oil additive. Notably, 1-Octanol poses a low level of toxicity, but it can be irritating to the skin and eyes. Nonetheless, it is considered safe to use under normal conditions because of its low vapor pressure.

化学的特性

1-Octanol has a fresh, orange-rose odor, quite sweet and an oily, sweet, slightly herbaceous taste.

天然物の起源

Reported as frequently occurring in essential oils as an ester; the free alcohol has been reported found in the essential oils of green tea, grapefruit, California orange, Andropogon intermedius, Heracleum villosum, violet leaves, Anethum graveolens and bitter orange. Also reported in over 200 foods and beverages including apple, apricot, banana, citrus peel oils and juices, many berries, guava, grapes, melon, papaya, peach, pear, asparagus, kohlrabi, leek, peas, tomato, potato, clove, ginger, mustard, spearmint oil, wheat bread, many cheeses, cooked egg, butter, milk, fish, meats, beer, rum, whiskies, cognac, cider, sherry, grape wines, cocoa, tea, nuts, honey, soybean, coconut, passion fruit, olive, avocado, plum, rose apple, beans, mushroom, starfruit, Bantu beer, sesame seed, cauliflower, broccoli, tamarind, fruit brandies, fig, cardamom, coriander seed and leaf, rice, quince, litchi, dill, lovage, sweet corn, corn oil, malt, kiwifruit, loquat, Bourbon vanilla, clary sage, oysters, crayfish, clam and Chinese quince.

調製方法

1-Octanol is made commercially by sodium reduction or high-pressure catalytic hydrogenation of the esters of naturally occurring caprylic acid or by oligomerization of ethylene using aluminum alkyl technology.

定義

ChEBI: Octan-1-ol is an octanol carrying the hydroxy group at position 1. It has a role as a plant metabolite. It is an octanol and a primary alcohol.

製造方法

1-Octanol may be prepared by reduction of some caprylic esters such as methyl caprylate with sodium ethoxide.

一般的な説明

A clear colorless liquid with a penetrating aromatic odor. Insoluble in water and floats on water. Vapors heavier than air. Vapors may irritate the eyes, nose, and respiratory system.

空気と水の反応

Insoluble in water.

反応プロフィール

Attacks plastics [Handling Chemicals Safely 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: an explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967; J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M. 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

健康ハザード

Irritates skin and eyes.

使用用途

1-オクタノールは、香料原料、界面活性剤原料、合成樹脂可塑剤原料、化粧品溶剤、食品添加物などに使用されます。ローズ系香料、 潤滑油、安定剤、印刷インキ溶剤、酢酸オクチルのようなエステル原料にも利用可能です。

液体クロマトグラフィーや薬学などの分野では、疎水性と親水性の指標として、水-オクタノール系の分配係数 (Log P) が使われます。

安全性プロファイル

Poison by intravenous route. Moderately toxic by ingestion. Mutation data reported. A skin irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water foam, fog, alcohol foam, dry chemical, CO2. See also ALCOHOLS.

発がん性

There was no evidence of tumors in the cancer screening lung adenoma study in which mice were injected intraperitoneally with 100 and 500 mg/kg 1- octanol three times a week for 8 weeks. This assay has not been validated as a reliable screen for cancer.
1-Octanol is a weak skin tumor promoter when applied three times a week for 60 weeks to mice skin that had been initiated with dimethylbenz[a]anthracene.

代謝

The primary aliphatic alcohols undergo two general reactions in vivo, namely oxidation to carboxylic acids and direct conjugation with glucuronic acid. The first reaction proceeds with the intermediate formation of an aldehyde, and the carboxylic acid from this may be either oxidized completely to carbon dioxide or excreted as such or combined with glucuronic acid as an ester glucuronide. The extent to which an alcohol undergoes the second reaction, i.e. direct conjugation to an ether glucuronide, appears to depend upon the speed of the first reaction, for alcohols which are rapidly oxidized form very little ether glucuronide unless given in high doses (Williams, 1959).

純化方法

Fractionally distil it under reduced pressure. Dry it with sodium and again fractionally distil or reflux with boric anhydride and re-distilled (b 195-205o/5mm), the distillate being neutralised with NaOH and again fractionally distilled. Also purify it by distillation from Raney nickel and by preparative GLC. [Beilstein 1 IV 1756.]