Диметилсульфид

Описание

Dimethyl sulfide, a sulfur ether compound, shares structural and property similarities with dimethyl ether. It is a colorless, volatile liquid that exhibits a distinct seafood-like odor. This compound is naturally generated through protein decomposition and serves as one of the culprits responsible for the fishy scent often associated with seafood.

Химические свойства

Methyl sulfide, also known as Dimethyl sulfide, is a clear colorless volatile liquid that has an intense, unpleasant odor, wild radish, cabbage-like. It can be tolerated as a green vegetable note only at very low levels (0.1 - 3.0 ppm). Dimethyl sulfide is soluble in ethanol and ether, but insoluble in water.

Вхождение

Reported found in American peppermint oil, the oil of Algerian geranium, mint fractions, butter, orange, orange juice and grapefruit juice, black currant, berries, asparagus, kohlrabi, cabbage, carrot, celery, onion, garlic, peas, potato, rutabaga, sauerkraut, tomato, Scotch spearmint oil, parsley, wheat bread, many cheeses, yogurt, milk, cream, buttermilk, raw and cooked egg, fish, chicken, cooked beef, mutton, pork liver, hop oil, beer, cognac rum, grape wines, sherry, tea, roasted filberts and peanuts, oats, soybean, olive, beans, mushroom, starfruit, trassi, Bantu beer, macadamia nut, mango, cauliflower, Brussels sprouts, rice, sake, buckwheat, sweet corn, malt, wort, dried bonito, krill, shrimp, oysters, truffle, okra, crab, clam and scallop

Использование

Dimethyl sulfide is used as a displaceable ligand in chloro(dimethyl sulfide)gold(I) and other coordination compounds, as a reducing agent in ozonolysis reactions as well as a food flavoring component. Further, it is utilized for the preparation of dimethyl sulfoxide, which is a common and important industrial solvent. It finds application in the petroleum industry.

Подготовка

By reaction of potassium sulfide with methyl chloride in methanol solution; from potassium methyl sulfate and potassium sulfide

Определение

ChEBI: Dimethyl sulfide is a methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae. It has a role as a bacterial xenobiotic metabolite, a marine metabolite, an EC 3.5.1.4 (amidase) inhibitor, an algal metabolite and an Escherichia coli metabolite.

Общее описание

A clear colorless to straw colored liquid with a disagreeable odor. Flash point less than 0°F. Less dense than water and slightly soluble in water. Vapors are heavier than air.

Реакции воздуха и воды

Highly flammable. Slightly soluble in water.

Профиль реактивности

Organosulfides, such as Dimethyl sulfide, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Dimethyl sulfide rapidly decomposes dibenzoyl peroxide explosively in the absence of solvent, [J. Org. Chem., 1972, 37, 2885]. The sulfide also decomposes xenon difluoride explosively at ambient temps, [J, Chem Soc., 1984, 2827]. Interaction of Dimethyl sulfide and oxygen is explosive at 210°C and above, [Atmos. Environ., 1967, 1, 491-497]. A delayed explosion occurred in a system containing nitric acid, Dimethyl sulfide, and 1, 4-dioxane, even with cooling with liquid nitrogen, [Chem. Abs., 1972, 76, 13515].

Угроза здоровью

Inhalation causes moderate irritation of upper respiratory system. Contact of liquid with eyes causes moderate irritation. Repeated contact with skin may extract oils and result in irritation. Ingestion causes nausea and irritation of mouth and stomach.

Профиль безопасности

Poison by inhalation. Moderately toxic by ingestion. A skin and severe eye irritant. A very dangerous fire hazard when exposed to heat or flame. Explosive in the form of vapor when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, use CO2, dry chemical. When heated to decomposition it emits highly toxic fumes of SOx and may explode. See also SULFIDES.

Методы очистки

Purify dimethyl sulfide via the Hg(II) chloride complex by dissolving 1 mole of Hg(II)Cl2 in 1250mL of EtOH and slowly adding the boiling alcoholic solution of Me2S to give the right ratio for 2(CH3)2S.3HgCl2. After recrystallisation of the complex to constant melting point, 500g of complex is heated with 250mL conc HCl in 750mL of water. The sulfide is separated, washed with water, and dried with CaCl2 and CaSO4. Finally, it is distilled under reduced pressure from sodium. Precautions should be taken (efficient fume hood) because of its very UNPLEASANT ODOUR.[Beilstein 1 IV 1275.]