イソブチルアルコール

外観

無色澄明の液体

性質

第一級アルコールの一種であり、異性体の1-ブタノールに近い性質を示します。融点は-108℃、沸点は108℃、引火点は30℃、比重は0.8 g/mL (at 25℃) 、屈折率n20/D 1.40、常温で液体です。エーテルやアルコールなど多くの有機溶剤と混和します。水への溶解性は87 g/L (at 20℃) です。

溶解性

水に可溶 (10%, 20℃), アルコール, エーテルと混和。エタノール及びジエチルエーテルに極めて溶けやすく、水にやや溶けやすい。

解説

C4H10O(74.12)．2-メチル-1-プロパノール(2-methyl-1-propanol)ともいう．イソブチルアルコールは，脂肪族飽和アルコール類の一つ．フーゼル油中に含まれる．工業的製法には，発酵法と，プロペンのオキソ合成法でブチルアルコールとともに合成する方法とがある．無色，引火性の液体．融点－108 ℃，沸点107.79 ℃．d²⁵₄ 0.79806．n²⁵_D 1.3939．爆発範囲(下限)1.68体積％．エタノール，エーテルに易溶，水に可溶．果物エッセンス用エステルの合成原料，溶剤などに用いられる．森北出版「化学辞典（第2版）

用途

大気中等イソブタノール（2-メチル-1-プロパノール）のGC分析標準液。

用途

イソブタノールは、塗料樹脂、アクリル酸イソブチル、酢酸イソブチル、メタクリル酸イソブチル、シンナー等の原料に使用されます。
一方、様々な有機物をよく溶解することから、溶媒としても広く利用されています。 

合成

イソブタノールの製造法

(CH₂CHCH₃) のヒドロホルミル化で生成した、 ((CH₃)₂CHCHO) を還元することで得られます。炭水化物の発酵産物や工業的な化成品の分解物としても生産されています。

特徴

1．イソブタノール（IBA）はイソブチルアルコールとも呼ばれ、炭素数4の分岐鎖アルコールです。
2．イソブタノールは水にほとんど溶解せず、ほとんどの有機溶媒に溶解します。

主な用途

イソブタノール（IBA）はイソブチルアルコールとも呼ばれ、炭素数4の分岐鎖アルコールです、は水にほとんど溶解せず、ほとんどの有機溶媒に溶解します。

1. 塗料樹脂、アクリル酸イソブチル、酢酸イソブチル、メタクリル酸イソブチル、シンナー等の原料に使用されます。
2. 様々な有機物をよく溶解することから、溶媒としても広く利用されています。
3. 溶剤型接着剤、水性型接着剤に使用される。

説明

Isobutyl alcohol has a disagreeable odor. May be prepared from isobutylene; by reduction of isobutyraldehyde with sodium amalgam or in the presence of a catalyst; by fermentation of isobutyraldehyde; isolated during fermentation of carbohydrates.

化学的特性

Isobutyl alcohol has a penetrating, wine-like, disagreeable odor

物理的性質

Clear, colorless, oily liquid with a sweet, musty odor. Burning taste. The average least detectable odor threshold concentration in water at 60 °C was 0.36 mg/L (Alexander et al., 1982). Experimentally determined detection and recognition odor threshold concentrations were 2.0 mg/m³ (660 ppb_v) and 5.4 mg/m³ (1.8 ppm_v), respectively (Hellman and Small, 1974). An odor threshold concentration of 11 ppb_v was reported by Nagata and Takeuchi (1990).

天然物の起源

Reported found in the essential oils of Java citronella, tea, Eucalyptus amygdalina. Also reported in apple and currant aromas; in apricots, banana, sweet cherry, orange, grapefruit and tangerine juice, berries, guava, grapes, melon, papaya, pear, pineapple, leek, peas, rutabaga, tomato, ginger, spearmint oil, vinegar, breads, cheeses, milk, fish oil, meats, hop oil, beer, cognac, rum, whiskies, sherry, cider, grape wines, cocoa, tea, coffee, nuts, oats, soybean, avocado, olive, passion fruit, plum, beans, mango, starfruit, bantu beer, plum brandy, tamarind, fig, cardamom, gin, quince, radish, prickly pear, litchi, sukiyaki, lovage leaf, buckwheat, sweet corn, laurel, malt, wort, elderberry juice, dried bonito, krill, kiwifruit, loquat, fruit brandies and wines, endive, shrimp, truffle, red currants, Roman chamomile oil and other sources.

使用

2-Methyl-1-propanol (Isobutyl alcohol) may be used to prepare the isobutyl alcohol-benzene solution for use in the quantification of inorganic phosphates. It may be used for the estimation of phosphate (inorganic phosphorous) by a colorimetric method.

定義

ChEBI: Isobutanol is an alkyl alcohol that is propan-1-ol substituted by a methyl group at position 2. It has a role as a Saccharomyces cerevisiae metabolite. It is a primary alcohol and an alkyl alcohol. It derives from a hydride of an isobutane.

製造方法

From isobutylene; by reduction of isobutyraldehyde with sodium amalgam or in the presence of a catalyst; by fermentation of isobutyraldehyde; isolated during fermentation of carbohydrates

調製方法

Isobutanol is commercially produced almost exclusively by the hydrogenation of isobutyraldehyde obtained from propylene using the oxo process.

一般的な説明

A clear colorless liquid with a sweet odor. Flash point 85 - 100°F. Less dense than water. Vapors heavier than air.

空気と水の反応

Highly flammable. Soluble in water.

反応プロフィール

2-Methyl-1-propanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. 2-Methyl-1-propanol is incompatible with strong oxidizers.

危険性

Flammable, moderate fire risk. Strong irritant.

健康ハザード

Inhalation causes eye and throat irritation andheadache. Ingestion may cause depression ofthe central nervous system. It is an irritantto the skin, causing cracking. Target organsare the eyes, skin, and respiratory system.
LD50 value, oral (rabbits): 3750 mg/kg.

火災危険

HIGHLY 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.

使用用途

イソブタノールの主な使用用途は、有機合成原料です。

イソブタノールの誘導体には、塗料樹脂、合成ゴム、石油添加剤、可塑剤等があり、重要なものが多いです。主にや塗料、食品工業の香料として使用される、の出発原料となります。酢酸イソブチルは、高濃度では発酵したような刺激臭があるため、特定悪臭物質に指定されています。

他にも、アクリル酸イソブチル、フタル酸イソブチル (DIBP) 、メタクリル酸イソブチルなど、種々の化成品のエステル化合物の原料にもなります。これらのイソブチルエステルは、プラスチックやゴムの可塑剤やポリマーの相分離を予防する分散化剤などに使われます。

また、様々な有機物を溶解することから、化学反応の溶媒・塗料やインクの溶剤としても用いられます。イソブタノールの塗料の粘性を低下させる性質を利用して、白化と呼ばれる塗装面での油分の分離を防ぐ目的にも使用されます。カーボン付着を防止するプラグ洗浄剤としてガソリンに添加されたり、ワックスやクリーナーにも利用されています。

調整をせずに、そのまま燃料用ブレンドストックへ応用することもできます。高価なハイオクタン価ガソリンや、その他の燃料用酸素化合物への混合や代替も可能です。

さらには、香料原料、医薬品原料、分析用試薬としても利用されているほか、近年では、バイオ燃料の原料としても注目されています。持続可能な航空燃料 (SAF: Sustainable Aviation Fuel) と呼ばれるバイオ燃料は、従来のジェット燃料と比べて二酸化炭素排出量を最大98%削減できます。

職業ばく露

Butyl alcohols are used as solvents for paints, lacquers, varnishes, natural and synthetic resins, gums, vegetable oils, dyes, camphor, and alkaloids. They are also used as an intermediate in the manufacture of pharmaceuticals and chemicals; in the manufacture of artificial leather, safety glass; rubber and plastic cements, shellac, raincoats, photographic films, perfumes; and in plastic fabrication.

発がん性

Nineteen Wistar rats were dosed with 0.2mL of isobutanol twice weekly by oral intubation. The average survival time was 495 days. It was reported that malignant tumors developed in three animals; one had a forestomach carcinoma and a liver cell carcinoma, another had a forestomach carcinoma and myelogenous leukemia, and the third, a myelogenous leukemia. In the same study, 24 rats were injected subcutaneously with 0.05 mL/kg twice weekly. The average survival time was 544 days. A total of eight malignant tumors developed: two forestomach carcinomas, two liver sarcomas, one spleen sarcoma, one mesothelioma, and two retroperitoneal sarcomas. Increased incidences of total tumors were observed by both routes of administration, but there was no significant increased incidence of any tumor type at any site. This study is considered inappropriate for cancer risk assessment.

輸送方法

UN1120 Butanols, Hazard Class: 3; Labels: 3— Flammable liquid. UN1212 Isobutanol or Isobutyl alcohol, Hazard Class: 3; Labels: 3—Flammable liquid

純化方法

Isobutanol is dried by refluxing with CaO and BaO for several hours, followed by treatment with calcium or aluminium amalgam, then fractional distilling it from sulfanilic or tartaric acids. More exhaustive purifications involve formation of phthalate or borate esters. Heating it with phthalic anhydride gives the acid phthalate which, after crystallisation to constant melting point (m 65o) from pet ether, is hydrolysed with aqueous 15% KOH. The alcohol is distilled off as the water azeotrope and dried (K2CO3, then anhydrous CuSO4), and finally magnesium turnings, followed by fractional distillation. [Hückel & Ackermann J Prakt Chem 136 15 1933.] The borate ester is formed by heating the dried alcohol for 6hours in an autoclave at 160-175o with a quarter of its weight of boric acid. After fractional distillation under vacuum, the ester is hydrolysed by heating for a short time with aqueous alkali and the alcohol is dried with CaO and distilled. [Michael et al. J Am Chem Soc 38 653 1916.] Alternatively dry the alcohol with K2CO3, CaSO4 or CaCl2, filter and fractionally distil it. For further drying, the redistilled alcohol can be refluxed with the appropriate alkyl phthalate or succinate as described under ethanol. [Beilstein 1 IV 1588.]

不和合性

Butyl alcohols may form explosive mixture with air. In all cases they are 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, oxoacids, epoxides. Attacks some plastics, rubber and coatings. n-Butanol is incompatible with strong acids; halogens, caustics, alkali metals; aliphatic amines; isocyanates. sec-Butanol forms an explosive peroxide in air. Ignites with chromium trioxide. Incompatible with strong oxidizers; strong acids; aliphatic amines; isocyanates, organic peroxides. tert-Butanol is incompatible with strong acids (including mineral acid), including mineral acids; strong oxidizers or caustics, aliphatic amines; isocyanates, alkali metals (i.e., lithium, sodium, potassium, rubidium, cesium, francium). isoButanol is incompatible with strong acids; strong oxidizers; caustics, aliphatic amines; isocyanates, alkali metals and alkali earth. May react with aluminum at high temperatur

廃棄物の処理

Incineration, or bury absorbed waste in an approved land fill.