tert-ブチル メルカプタン 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
溶解性
水に微溶, エタノール, エーテルに易溶。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。
用途
付臭剤、有機合成原料。
用途
農薬原料、ガス着臭剤
説明
tert-Butylthiol, also known as 2-methyl propane-2-thiol, 2- methyl-2-propane thiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organo sulfur compound with the formula (CH
3)
3CSH. This thiol may have been used as a flavoring agent, as an odorant for natural gas (which is odorless), and also in a wide range of organic reactions.
化学的特性
liquid with an exceedingly unpleasant smell
使用
2-Methyl-2-propanethiol was used in reaction of 2-methyl-2-propanethiol on Mo(110) using temperature programmed reaction, high resolution electron enegy loss and X-ray photoelectron spectroscopies. It was used in the synthesis of chain-transfer agents for reversible addition-fragmentation chain-transfer copolymerization of vinylidene chloride and methyl acrylate.
製造方法
tert-Butyl thiol likely does not occur naturally, but at least one publication has listed it as a very minor component of cooked potatoes. The compound was first prepared in 1890 by Leonard Dobbin by the reaction of zinc sulfide and t-butyl chloride.
The compound was later prepared in 1932 by the reaction of the Grignard reagent, t-BuMgCl, with sulfur to give the corresponding thiolate, followed by hydrolysis. This preparation is shown below:
t-BuMgCl + S → t-BuSMgCl
t-BuSMgCl + H
2O → t-BuSH + Mg(OH)Cl
It is currently prepared industrially by the reaction of isobutylene with hydrogen sulfide over a clay (silica alumina) catalyst.
反応性
tert-Butylthiol can react with metal alkoxides and acyl chlorides to form thiol esters, as shown in the equation :
In the reaction above, thallium (I) ethoxide converts to thallium (I) t-butyl thiolate. In the presence of diethyl ether, thallium (I) tbutylthiolate reacts with acyl chlorides to give the corresponding tertbutyl thioesters. Like other thio esters, it reverts back to tert-butylthiol by hydrolysis.
Lithium 2-methyl propane-2-thiolate can be prepared by treatment of tert-butyl thiol with lithium hydride in an aprotic solvent such as hexa methyl phosphorous triamide (HMPT). The resulting thiolate salt is a useful demethylating reagent. For example, treatment with 7- methyl guanosine gives guanosine. Other N-methylated nucleosides in tRNA are not demethylated by this reagent .
一般的な説明
2-Methyl-2-propanethiol undergoes ring opening nucleophilic reaction with 3-isothiazolones and reaction kinetics studies suggested reaction was second order in thiol and third order overall.
危険性
Flammable, dangerous fire risk. Very toxic.
安全性プロファイル
Moderately toxic by
intraperitoneal route. Mildly toxic by
ingestion. An eye irritant. A very dangerous
fire hazard when exposed to heat or flame.
Can react vigorously with oxidizing
materials. To fight fire, use alcohol foam,
dry chemical, mist, fog. When heated to
decomposition or on contact with acid or
acid fumes it emits highly toxic fumes of
SOx.
安全性
Even in well ventilated areas, extreme caution must be made when handling tert-butylthiol as it is a highly odorous chemical with an odor threshold of < 0.33 ppb. Extreme caution is not due to toxicity, but due to the significant odor and concerns that this odor would cause to the many individuals that might be exposed. The PEL for thiols of most types is 500 ppb, primarily due to reaction of nausea at levels of 2–3 ppm. The LC
50 of tert-butylthiol is much, much higher.
純化方法
Dry the thiol for several days over CaO, then distil it from CaO. Purify it as for 2-methylpropane-1-thiol above. [Beilstein 1 H 383, 1 II 416, 1 III 1589, 1 IV 1634.]
tert-ブチル メルカプタン 上流と下流の製品情報
原材料
準備製品