γ-ブチロラクトン

外観

無色～ほとんど無色, 澄明の液体

定義

本品は、次の化学式で表されるラクトンである。

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

dihydro-2(3H)-furanone．C4H6O2(86.09)．γ-ブチロラクトンは，γ-オキシ酪酸ラクトンともいう．γ-ブロモ酪酸をナトリウムエトキシドで処理するか，1,4-ブタンジオールと水蒸気を銅触媒上に通じて得られる．また工業的には，無水マレイン酸のNi-Re触媒による還元により，テトラヒドロフランとともに製造される．油状の液体．融点－44 ℃，沸点206 ℃，89 ℃(1.6 kPa)．d¹⁵₀ 1.1286．n²⁵D 1.4348．水，エタノール，エーテル，ベンゼンに可溶．熱アルカリ溶液で加水分解される．アンモニア性硝酸銀を還元する．ポリ(ビニルピロリドン)，ピペリジン，フェニル酢酸，ビタミン B12，DL-メチオニンなどの合成中間体．また，ポリアクリロニトリル，酢酸セルロース，ポリスチレンなどの溶剤として用いられる．森北出版「化学辞典（第2版）

用途

塗料除去剤、繊維助剤、掘削油。

化粧品の成分用途

溶剤、香料

特徴

γ-ブチロラクトン（GBL）は、凝固点が低く、沸点が高い安定な物質で、かつ特異な溶解性および電気特性を有するため、特殊樹脂の溶剤、写真や電池、電解液分野への応用など幅広く使用されているほか、その化学反応性を利用して各種誘導体が合成されています。

主な用途

１）溶剤等の用途
■ 溶剤関係
感光性樹脂溶剤あるいは特殊インキ溶剤として使用されています。
■ 写真関係
分散および表面処理剤として使用されています。
■ 電気関係
コンデンサ向け電解液溶媒、およびリチウム電池向け電解液溶媒として用いられます。
■ 鋳物バインダー
２）合成原料用途
以下に挙げる溶剤の原料として使用されます。
■ 2－ピロリドン（2P）
2Pは医薬中間体原料、ナイロン4原料、NMP原料、床磨き剤などに用いられます。
■ N－メチル－2－ピロリドン（NMP）
NMPは芳香族、ブタジエンなどの炭化水素抽出溶剤、ポリアミド · ポリイミド樹脂のワニス溶剤、半導体やカラーフィルター用フォトレジスト溶媒などに用いられます。
■ N－ビニル－2－ピロリドン（NVP）
NVPはPVP原料の他、抜染剤、石油添加剤などに用いられます。
■ ポリビニルピロリドン（PVP）
PVPは化粧品用（ヘアースプレー · ローションなどの増粘剤）、医薬品用（錠剤バインダー、代用血漿、うがい薬）、工業用（懸濁重合のコロイド安定剤、染色助剤、焼き入れ油粘度調整剤、接着剤増粘剤）、食品用（ビール、ワインの清澄化剤）に用いられます。
■ その他
メチオニン、チオジブチル酸エステルなど多岐な用途があります。

説明

Dihydro-2(3H)-furanone. An endogenous neuroregulator made from gamma-amino butyrate and the precursor of gamma hydroxybutyrate. It causes selective increase of brain dopamine by inhibiting its release from nerve terminals. The compound has sedative properties at low doses and produces surgical anesthesia at high doses. It is also used as an industrial solvent and precursor.

化学的特性

γ-Butyrolactone is oily, colorless, clear liquid. It has a faint, sweet, aromatic, slightly buttery odor.

γ-Butyrolactone is a lactone. It is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. Under acidic conditions it forms an equilibrium mixture of both compounds. These compounds then may go on to form a polymer.

天然物の起源

Reported found as a constituent in coffee aroma; a volatile flavor component in roasted filberts as well. Also reported found in tomato, potato, soybeans, beans, vinegar, mushrooms, roasted chicken, beef, cider, beer, wine, scallops and clams.

使用

r-butyrolactone is one kind of important fine chemicalintermediate, simultaneously also is one kind of performance fine highboiling point solvent, ideal antioxidant, plasticizer,extracting agent, absorbent, dispersing agent, solid stain, Coagulation Reagent.

製造方法

γ-Butyrolactone is produced by gas phase 1,4-butanediol under the action of Cu catalyst to produce product γ-butyrolactone and by-product hydrogen. Crude γ-Butyrolactone is purified to remove light and heavy components, with a purity of more than 99.5%, as an export product. At the same time, the by-product hydrogen is sent to other hydrogenation processes for recycling after removing CO and CO2 through the methanation process.

定義

ChEBI: A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.

一般的な説明

Clear colorless oily liquid with a pleasant odor.

空気と水の反応

Hygroscopic. Soluble in water.

反応プロフィール

gamma-Butyrolactone can react with oxidizing materials, inorganic acids and bases, alcohols and amines. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. gamma-Butyrolactone is volatile with steam. . The combination of the lactone, butanol, 2,4-dichlorophenol, and sodium hydroxide in the attempted synthesis of 2,4-dichlorophenoxybutyric acid caused a thermal runaway reaction that eventually exploded, [CISHC Chem. Safety Summ., 1977, 48, 3].

危険性

Toxic by ingestion. Questionable carcino- gen.

火災危険

gamma-Butyrolactone is combustible.

安全性プロファイル

Moderately toxic by ingestion, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data by skin contact. Mutation data reported. Less acutely toxic than ppropiolactone. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, alcohol foam, CO2, dry chemical. Potentially explosive reaction with butanol + 2,4 dichlorophenol + sodium hydroxide. When heated to decomposition it emits acrid and irritating fumes.

職業ばく露

Used as a chemical intermediate for making other chemicals, including pesticides, cosmetics, and pharmaceuticals; as a solvent for paint, nail polish removers, and industrial chemicals. Used in electronics, drilling and petroleum industries as a stabilizer and solvent. Used as a flavoring agent in various foods and beverages, including grains and breakfast foods, candy, and alcoholic and nonalcoholic drinks. Drug of abuse: the United States Food and Drug Administration has warned the public not to purchase or consume products, containing gamma-butyrolactone (GBL). FDA has also asked the companies that manufacture these products to voluntarily recall them. The agency has received reports of serious health problems—some that are potentially life-threatening—associated with the use of these products. Although labeled as dietary supplements and marketed under various brand names, these products are illegally marketed unapproved new drugs. False advertising claims include building muscles, improved physical performance, enhanced sex, reduced stress and induced sleep

輸送方法

Listed by some sources as unregulated. UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.

純化方法

Dry the lactone over anhydrous CaSO4, then fractionally distil it. Handle it in a fume cupboard due to its TOXICITY. [Beilstein 17 V 7.]

不和合性

4-Butyrolactone is incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, alcohols, amines, strong and inorganic acids, strong bases. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. It is hygroscopic and volatile with steam. Combustible; vapor may form explosive mixture with air.

廃棄物の処理

Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. All federal, state, and local environmental regulations must be observed.