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| 融点 | -42.8 °C | | 沸点 | 166 °C(lit.) | | 比重(密度) | 0.938 g/mL at 20 °C | | 蒸気密度 | 4 (vs air) | | 蒸気圧 | <1 mm Hg ( 20 °C) | | 屈折率 | n20/D 1.423(lit.) | | 闪点 | 132 °F | | 貯蔵温度 | Store below +30°C. | | 溶解性 | Soluble in alcohol, ether (Weast, 1986), and many other solvents, particular ketones such as
acetone and 2-butanone. | | 酸解離定数(Pka) | 14.57±0.29(Predicted) | | 外見 | Liquid | | 色 | Clear colorless | | 臭い (Odor) | Mild, pleasant. | | 爆発限界(explosive limit) | 1.8-6.9%(V) | | 水溶解度 | MISCIBLE | | 極大吸収波長 (λmax) | 249nm(lit.) | | Merck | 14,2964 | | BRN | 1740440 | | Specific Activity | 25-50 mCi/mmol | | Solvent | Ethanol | | Concentration | 0.1 mCi/ml | | 暴露限界値 | TLV-TWA 240 mg/m3 (50 ppm) (ACGIH);
IDLH 2100 ppm (NIOSH). | | Dielectric constant | 18.2（Ambient） | | 安定性： | Stable. Flammable. Incompatible with strong oxidizing agents, amines, ammonia, strong acids, strong bases, alkalies, aluminium. | | LogP | -0.09 at 20℃ | | CAS データベース | 123-42-2(CAS DataBase Reference) | | NISTの化学物質情報 | 4-Hydroxy-4-methylpentan-2-one(123-42-2) | | EPAの化学物質情報 | 4-Hydroxy-4-methyl-2-pentanone (123-42-2) |
| | ジアセトンアルコール Usage And Synthesis |
| 外観 | 無色澄明の液体 | | 種類 | ジアセトンアルコールは、一般的に研究開発用試薬製品や、工業用薬品などとして販売されている物質です。
1. 研究開発用試薬製品
研究開発用試薬製品としては、500mL、15kgなどの容量の種類があります。実験室で取り扱いやすい容量で取り扱われることが多いですが、比較的大きな容量での提供もあり、安価な試薬製品です。通常は、室温で保管可能な試薬製品としての提供となります。
2. 工業用薬品
工業用薬品としては、主に溶剤 (特に塗料の溶剤、グラビアインクの溶剤、接着剤の溶剤、殺虫剤の溶剤、 写真フィルムの原料など) の用途を想定して販売されている物質です。荷姿としては16kg石油缶、196kgドラム、1,000Lコンテナなどがあります。
| | 定義 | 本品は、次の化学式で表されるケトンである。 | | 性質 | ジアセトンアルコールは、分子量116.16、融点-44℃、沸点167.9℃であり、常温での外観は無色の液体です。臭いはほぼ無く、一般的な取り扱いにおいては安定な化合物です。
水への溶解度は、1.00×106mg/Lであり、アルコール、エーテルに混和します。密度は 0.93g/mL、引火点は66℃、自然発火温度は603℃です。
| | 溶解性 | 水、エタノール及びアセトンに極めて溶けやすい。 | | 解説 | ⇒アセチルアセトン
小学館 デジタル大辞泉について 情報 | 凡例 | | 用途 | 油脂、樹脂、ニトロセルロース等の溶媒。低蒸気圧の高沸点溶剤で、有機重質液体の粘度低下および粘度に対する温度の影響を少なくするのに優れた効果があり、セルロースエステルラッカー、印刷インキ、アルキドおよびビニル系樹脂塗料、脂肪、エポキシ樹脂などの溶剤、水硬剤、写真用フィルム、氷結防止剤、人工シルク、レザーなどの製造に用いられる。 | | 用途 | 溶剤、塗料 | | 化粧品の成分用途 | 溶剤、香料 | | 合成 | 
図1. ジアセトンアルコールの合成
ジアセトンアルコールは、アセトン2分子が縮合した構造を有しており、工業的にもをに二量化する方法で合成されます。具体的には、水酸化バリウムなどの塩基を触媒としてアセトンにアルドール縮合を行わせる方法が一般的です。
| | 危険性 | ジアセトンアルコールは、GHS分類において引火性液体、皮膚腐食性/刺激性、眼刺激性、生殖毒性、特定標的臓器・全身毒性に分類されています。
| | 主な用途／役割 | 溶剤型接着剤に使用される。 | | 説明 | Diacetone alcohol is a colorless liquid with amild, minty odor. Odor threshold = 0.28 ppm. Molecularweight = 116.16; Specific gravity (H2O:1) = 0.94; Boilingpoint = 168℃; Freezing/Melting point = - 43.8℃; Vaporpressure = 1 mmHg at 20℃; Flash point = 64℃; 58℃(acetone free); 64℃ (commercial grade). Explosive limits:LEL = 1.8%; UEL = 6.9%. Hazard Identification (based onNFPA-704 M Rating System): Health 1, Flammability 2,Reactivity 0. Soluble in water. | | 化学的特性 | colourless liquid | | 化学的特性 | Diacetone alcohol is a colorless liquid. Mild,
mint odor. | | 物理的性質 | Clear, watery, flammable liquid with a mild, pleasant, characteristic odor similar to 2-butanone or
the pentanones. Experimentally determined detection and recognition odor threshold concentrations
were 1.3 mg/m3 (270 ppbv) and 5.2 mg/m3 (1.1 ppmv), respectively (Hellman and Small,
1974). | | 使用 | Solvent for pigments, cellulose, resins,
oils, fats, and hydrocarbons; hydraulic brake
fluid; antifreeze | | 使用 | 4-Hydroxy-4-methyl-2-pentanone is used asa solvent for nitrocellulose, cellulose acetate,resins, fats, oils, and waxes; and in hydraulicfluids and antifreeze solutions.. | | 使用 | Solvent for cellulose acetate, nitrocellulose, celluloid, fats, oils, waxes, resins. As a preservative in pharmaceutical preparations. In some antifreeze solutions and in hydraulic fluids. | | 調製方法 | 4-Hydroxy-4-methyl-2-pentanone is manufactured through
the action of barium hydroxide, potassium hydroxide, or calcium
hydroxide on acetone. Commercial materials may contain
up to 15%acetone. | | 定義 | ChEBI: A beta-hydroxy ketone formed by hydroxylation of 4-methylpentan-2-one at the 4-position. It has been isolated from Achnatherum robustum. | | Synthesis Reference(s) | Organic Syntheses, Coll. Vol. 1, p. 199, 1941
Tetrahedron Letters, 16, p. 4027, 1975 DOI: 10.1016/S0040-4039(00)91227-9 | | 一般的な説明 | A clear colorless liquid with a pleasant odor. Flash point below 141°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 | 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 | Vapor is irritating to the mucous membrane of the eye and respiratory tract. Inhalation can cause dizziness, nausea, some anesthesia. Very high concentrations have a narcotic effect. The liquid is not highly irritating to the skin but can cause dermatitis. | | 健康ハザード | 4-Hydroxy-4-methyl-2-pentanone is a mildirritant and a strong narcotic. It can causeirritation in the eyes, nose, throat, and skin.The effect on humans, however, is mild at100 ppm concentration.
Animal experiments indicated that it couldproduce sleep after a period of restlessnessand excitement. The symptoms of its toxicity are a marked decrease in breathing andblood pressure, and relaxation of the muscles. Ingestion of this compound in highdoses can damage corneal tissue and liver.The oral toxicity in rats was very low, witha LD50 value of 4000 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 | ジアセトンアルコールの主な使用用途は、 油脂、樹脂、ニトロセルロース等の溶媒、及び、印刷インキ、コーティング加工用樹脂、金属加工液、潤滑剤、洗浄剤などです。ジアセトンアルコールは、低蒸気圧の高沸点溶剤であるという特徴を持ち、有機重質液体の粘度低下および粘度に対する温度の影響を少なくするのに優れた効果があります。
具体的には特に、セルロースエステルラッカー、印刷インキ、アルキドおよびビニル系樹脂塗料、脂肪、エポキシ樹脂などの溶剤、水硬剤、写真用フィルム、氷結防止剤、人工シルク、レザーなどの製造に用いられています。また、ジアセトンアルコールは、各有機化合物の原料としても用いられる物質です。
特に重要な生成化合物として、溶媒、塗料の原料として用いられる、電子材料用途などに用いられるメチルイソブチルカルビノール、浸透剤や洗剤の原料として用いられるへキシレングリコールなど、が挙げられます。
| | 法規制情報 | これらの危険性により、ジアセトンアルコールは法令によって規制を受ける物質です。労働安全衛生法において危険物・引火性の物、また名称等を表示・通知すべき危険有害物に指定されており、リスクアセスメントを実施すべき危険有害物、および消防法において、第4類第二石油類に指定されています。法令を遵守して正しく取り扱うことが重要です。
| | 化学反応 | 
図2. ジアセトンアルコールの脱水反応
ジアセトンアルコールは、加熱、燃焼や、酸、塩基、アミンとの接触により、分解してアセトンとメシチルアルコールを生じます。また、酸化剤と激しく反応し、引火性/爆発性の気体 (水素) を生成する性質があります。混触危険物質は 酸、塩基、アミン、酸化剤であり、危険有害な分解生成物はアセトン、メシチルアルコール、水素です。
また、ジアセトンアルコールに触媒量のヨウ素を加えることによって脱水反応が起こり、メシチルオキシドが生成します。
| | 化学反応性 | Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | | 安全性プロファイル | Moderately toxic by
ingestion and intraperitoneal routes. Mddly
toxic by skin contact. Human systemic
effects by inhalation: headache, nausea or
vomiting, eye and pulmonary changes. A
skin, mucous membrane, and severe eye
irritant. Can cause anemia and damage to
liver and hdneys. Narcotic in high
concentration. Flammable liquid when
exposed to heat or flame; can react with
oxidzing materials. Explosive in the form of
vapor when exposed to heat or flame. To
fight fire, use alcohol foam, foam, CO2, dry
chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See
also KETONES. | | 職業ばく露 | It is used as a solvent for pigments,
cellulose esters; oils and fats. It is used in hydraulic brake
fluids and in antifreeze formulations. | | 応急処置 | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. | | 発がん性 | Occupational exposure to 4-hydroxy-4-methyl-2-
pentanone is most likely to be by inhalation and skin contact.
It presents a low degree of hazard if good work practices are
observed. Appropriate protective clothing and eye protection
should be made available as prolonged exposure may defat the skin and cause dermatitis. The occurrence of eye, nose,
and throat irritation and a recognizable odor at low concentrations
should protect against overexposure to 4-hydroxy-4-
methyl-2-pentanone. | | 環境運命予測 | Biological. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM
BOD/mM diacetone alcohol) and ThOD were 3.67 and 45.9%, respectively (Vaishnav et al.,
1987).
Photolytic. Grosjean (1997) reported a rate constant of 4.0 x 10-12 cm3/molecule?sec at 298 K for
the reaction of OH radicals in the atmosphere. Based on a OH concentration of 1.0 x 106
molecule/cm3, the reported half-life of diacetone alcohol is 2.0 d (Grosjean, 1997). | | 貯蔵 | Color Code—Red: Flammability Hazard: Store in aflammable liquid storage area or approved cabinet away fromignition sources and corrosive and reactive materials. Prior toworking with this chemical you should be trained on its properhandling and storage. Before entering confined space wherethis chemical may be present, check to make sure that anexplosive concentration does not exist. Diacetone alcohol mustbe stored to avoid contact with strong oxidizers (such as chlorine, bromine, and fluorine) or strong alkalis (such as sodiumhydroxide or potassium hydroxide) since violent reactionsoccur. Store in tightly closed containers in a cool, wellventilated area away from heat. Sources of ignition, such assmoking and open flames, are prohibited where diacetone alcohol is used, handled, or stored in a manner that could create apotential fire or explosion hazard. Metal containers involvingthe transfer of 5 gallons or more of diacetone alcohol shouldbe grounded and bonded. Drums must be equipped with selfclosing valves, pressure vacuum bungs, and flame arresters. | | 輸送方法 | UN1148 Diacetone alcohol, Hazard Class: 3;
Labels: 3-Flammable liquid. | | 純化方法 | The pentanone loses water when heated. It can be dried with CaSO4, then fractionally distilled under reduced pressure. [Beilstein 1 IV 403.] | | 不和合性 | Vapor may form explosive mixture with
air. Incompatible with oxidizers (chlorates, nitrates, perox-
ides, permanganates, perchlorates, chlorine, bromine, fluo-
rine, etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong bases, strong acids,
oxoacids, and epoxides. | | 廃棄物の処理 | Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera-
tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be observed. |
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