t-ブチルヒドロペルオキシド

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H226：引火性の液体および蒸気

  H242：熱すると火災のおそれ

  H300：飲み込むと生命に危険

  H302：飲み込むと有害

  H304：飲み込んで気道に侵入すると生命に危険のおそ れ

  H310：皮膚に接触すると生命に危険

  H311：皮膚に接触すると有毒

  H314：重篤な皮膚の薬傷?眼の損傷

  H317：アレルギー性皮膚反応を起こすおそれ

  H318：重篤な眼の損傷

  H330：吸入すると生命に危険

  H336：眠気やめまいのおそれ

  H341：遺伝性疾患のおそれの疑い

  H371：臓器の障害のおそれ

  H372：長期にわたる、または反復暴露により臓器の障 害

  H373：長期にわたる、または反復暴露により臓器の障 害のおそれ

  H410：長期的影響により水生生物に非常に強い毒性

  H411：長期的影響により水生生物に毒性

• 注意書き

  P201：使用前に取扱説明書を入手すること。

  P202：全ての安全注意を読み理解するまで取り扱わないこ と。

  P210：熱/火花/裸火/高温のもののような着火源から遠ざ けること。－禁煙。

  P220：衣類/．．．/可燃物から遠ざけること。

  P233：容器を密閉しておくこと。

  P234：他の容器に移し替えないこと。

  P240：容器を接地すること/アースをとること。

  P260：粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。

  P261：粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。

  P264：取扱い後は皮膚をよく洗うこと。

  P264：取扱い後は手や顔をよく洗うこと。

  P270：この製品を使用する時に、飲食または喫煙をしないこ と。

  P271：屋外または換気の良い場所でのみ使用すること。

  P272：汚染された作業衣は作業場から出さないこと。

  P273：環境への放出を避けること。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P284：呼吸用保護具を着用すること。

  P301+P310：飲み込んだ場合：直ちに医師に連絡すること。

  P303+P361+P353：皮膚（または髪）に付着した場合：直ちに汚染された衣 類をすべて脱ぐこと/取り除くこと。皮膚を流水/シャワー で洗うこと。

  P304+P340：吸入した場合：空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。

  P305+P351+P338：眼に入った場合：水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

  P310：ただちに医師に連絡すること。

  P320：特別な治療が緊急に必要である（このラベ ルの．．．を見よ）。

  P331：無理に吐かせないこと。

  P403+P233：換気の良い場所で保管すること。容器を密閉 しておくこと。

  P405：施錠して保管すること。

  P410：日光から遮断すること。

t-ブチルヒドロペルオキシド 価格

MSDS Information

• TBHP

t-ブチルヒドロペルオキシド 化学特性,用途語,生産方法

• 外観

  無色～ほとんど無色透明液体

• 溶解性

  水に可溶 ≧10 g/100 mL at 22℃。水、エタノール及びアセトンと任意の割合で混和する。

• 解説

  t-ブチルヒドロペルオキシド，工業製品は，約70％ 水溶液である．融点4.0～4.5 ℃，沸点35 ℃(2.7 kPa)．d²⁰₄ 0.896．n²⁰_D 1.4007．有機溶媒に可溶．約75 ℃ まで安定であるが，常圧蒸留では爆発する．有機合成では，ヘキサカルボニルモリブデンなどの金属触媒の存在下，不飽和アルコールの不斉エポキシ化，シリルエノールエーテルの酸化開裂，アリル位の酸化などに広く用いられている．重合触媒，硬化剤として工業的に利用される．
  森北出版「化学辞典（第2版）

• 用途

  有機合成試薬。

• 用途

  樹脂製造用重合剤、硬化剤

• 製造

  t-ブチルアルコールまたはイソブチレンを硫酸でスルホン化し，ついで過酸化水素と反応させて工業的に製造されているt-ブチルヒドロペルオキシド．

• 毒性

  LD50 406 mg/kg(ラット，経口)．

• 説明

  tert-Butyl hydroperoxide (TBHP) is an organic peroxide widely used in a variety of oxidation processes.

• 化学的特性

  tert-Butyl hydroperoxide (TBHP) is a water-white liquid commonly commercially available as a 70% solution in water; 80% solutions are also available. It is used to initiate polymerization reactions and in organic syntheses to introduce peroxy groups into the molecule. TBHP vapor can burn in the absence of air and may be flammable at either elevated temperature or at reduced pressure. Fine mist/spray may be combustible at temperatures below the normal flash point. When evaporated, the residual liquid will concentrate TBHP content and may reach an explosive concentration (＞90%). Closed containers may generate internal pressure through the degradation of TBHP to oxygen . TBHP is a highly reactive product. The three types of significant physical hazards are flammability, thermal, and decomposition due to contamination. To minimize these hazards, avoid exposure to heat, fire, or any condition that will concentrate the liquid material. Store away from heat, sparks, open flames, foreign contaminants, combustibles, and reducing agents. Inspect containers frequently to identify bulges or leaks (7a, 125).

• 使用

  tert-Butyl hydroperoxide is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation. It is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions. Furthermore, it is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes. It plays an important role for the introduction of peroxy groups in organic synthesis.

• 調製方法

  TBHP is produced by the liquid-phase reaction of isobutane and molecular oxygen or by mixing equimolar amounts of t-butyl alcohol and 30–50% hydrogen peroxide. TBHP can also be prepared from t-butyl alcohol and 30% hydrogen peroxide in the presence of sulfuric acid or by oxidation of tert-butylmagnesium chloride. The manufacturing process of TBHP is in a closed system.

• 定義

  ChEBI: Tert-butyl hydroperoxide is an alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes. It has a role as an antibacterial agent and an oxidising agent.

• 一般的な説明

  Watery odorless colorless liquid. Floats and mixes slowly with water.

• 空気と水の反応

  Water soluble.

• 反応プロフィール

  Most alkyl monohydroperoxides are liquid. The explosivity of the lower members (e.g., methyl hydroperoxide, or possibly, traces of the dialkyl peroxides) decreasing with increasing chain length and branching [Bretherick 2nd ed. 1979 p. 10]. Though relatively stable, explosions have been caused by distillation to dryness [Milas, JACS 1946, 68, 205] or attempted distillation at atmospheric pressure [Castrantas 1965 p. 15].

• 危険性

  Moderate fire risk. Oxidizer.

• 健康ハザード

  tert-Butyl hydroperoxide is a strong irritant.Floyd and Stockinger (1958) observed thatdirect cutaneous application in rats did notcause immediate discomfort, but the delayedaction was severe. The symptoms were erythemaand edema within 2–3 days. Exposureto 500 mg in 24 hours produced asevere effect on rabbit skin, while a rinse of150 mg/min was severe to eyes.
  It is moderately toxic; the effects aresomewhat similar to those of MEK peroxide.Symptoms from oral administration in ratswere weakness, shivering, and prostration.
  LD₅₀ value, intraperitoneal (rats): 87 mg/kg
  LD₅₀ value, oral (rats): 406 mg/kg.

• 燃焼性と爆発性

  tert-Butyl hydroperoxide is a flammable liquid and a highly reactive oxidizing agent. Pure TBHP is shock sensitive and may explode on heating. Carbon dioxide or dry chemical extinguishers should be used for fires involving tert-butyl hydroperoxide.

• 作用機序

  The general mechanism of transition metal-catalyzed oxidative Mannich reactions of N, N-dialkyl anilines with tert-butyl hydroperoxide (TBHP) as the oxidant consists of a rate-determining single electron transfer (SET) that is uniform from 4-methoxy- to 4-cyano-N, N-dimethylanilines. The tert-butylperoxy radical is the major oxidant in the rate-determining SET step that is followed by competing backward SET and irreversible heterolytic cleavage of the carbon–hydrogen bond at the α-position to nitrogen. A second SET completes the conversion of N, N-dimethylaniline to an iminium ion that is subsequently trapped by the nucleophilic solvent or the oxidant prior to the formation of the Mannich adduct[1].
  Tert-butyl hydroperoxide could induce oxidative stress in liver mitochondria at low concentrations. The damaging effect of low concentrations of tBHP in the course of pyruvate oxidation in isolated liver mitochondria is caused by the opening of the nonspecific Ca²⁺-dependent cyclosporin A-sensitive pore in the inner mitochondrial membrane[2].

• 安全性プロファイル

  Moderately toxic by ingestion and inhalation. A severe skin and eye irritant. Mutation data reported. At highest dosage levels, symptoms noted were severe depression, incoordmation, and cyanosis. Death was due to respiratory arrest. Very dangerous fire hazard when exposed to heat or flame, or by spontaneous chemical reaction such as with reducing materials. Moderately explosive; may explode during distillation. Violent reaction with traces of acid. Concentrated solutions may ignite spontaneously on contact with molecular sieve. Mixtures with transition metal salts may react vigorously and release oxygen. Forms an unstable solution with 1,2-dichloroethane. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also PEROXIDES, ORGANIC.

• 発がん性

  A study performed to evaluate the carcinogenicity of TBHP found it was not carcinogenic when applied to the skin of mice at 16.6% of the peroxide 6 times a week for 45 weeks. However, if its application was preceded by 0.05 mg of 4-nitroquinoline-1-oxide as a 0.25% solution in benzene applied 20 times over 7 weeks followed by TBHP (16.6% in benzene), then malignant skin tumors appeared between days 390 and 405 of the experiment . This supports the theory that peroxides are not complete carcinogens, but may act as promoters . The effects of TBHP on promotable and nonpromotable mouse epidermal cell culture lines were reported by Muehlematter et al. .

• 貯蔵

  tert-butyl hydroperoxide should be stored in the dark at room temperature (do not refrigerate) separately from oxidizable compounds, flammable substances, and acids. Reactions involving this substance should be carried out behind a safety shield.

• 不和合性

  tert-Butyl hydroperoxide and concentrated aqueous solutions of TBHP react violently with traces of acid and the salts of certain metals, including, in particular, manganese, iron, and cobalt. Mixing anhydrous tert-butyl hydroperoxide with organic and readily oxidized substances can cause ignition and explosion. TBHP can initiate polymerization of certain olefins.

• 廃棄物の処理

  Excess tert-butyl hydroperoxide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

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