Диметилсульфоксид

Описание

First synthesized in 1866 by Alexander Zaytsev in the Russian Empire, dimethyl sulfoxide is an organosulfur compound. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water.

Химические свойства

Dimethyl sulfoxide occurs as a colorless, viscous liquid, or as colorless crystals that are miscible with water, alcohol, and ether. The material hasa slightly bitter taste with a sweet aftertaste, and is odorless, or has a slight odor characteristic of dimethyl sulfoxide.Dimethyl sulfoxide is extremely hygroscopic, absorbing up to 70% of its own weight in water with evolution of heat.

Вхождение

Reported found in apple, raspberry, cabbage, cucumber, onion, tomato, peppermint and spearmint oils, milk, pork liver, beer, rum, cocoa, coffee, black tea, oatmeal, soybean, beetroot, parsnip root, watercress, sweet corn, malt, cooked shrimp and oysters

Использование

Dimethyl sulfoxide (1-10%) has been shown to accelerate strand renaturation and is believed to give the nucleic acid thermal stability against depurination. As a PCR cosolvent, DMSO may help improve yields, especially in long PCR.

Определение

ChEBI: A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.

Методы производства

Dimethyl sulfoxide is prepared by air oxidation of dimethyl sulfide in the presence of nitrogen oxides. It can also be obtained as a by product of wood pulp manufacture for the paper and allied industries.

Общее описание

A clear liquid, essentially odorless. Closed cup flash point 192°F. Vapors are heavier than air. Contact with the skin may cause stinging and burning and lead to an odor of garlic on the breath. An excellent solvent that can transport toxic solutes through the skin. High vapor concentrations may cause headache, dizziness, and sedation.

Реакции воздуха и воды

Denser than water and miscible in water.

Профиль реактивности

Dimethyl sulfoxide decomposes violently on contact with many acyl halides, aryl halides and related compounds such as phenyl and tolyl chloride, acetyl chloride, benzenesulfonyl chloride, benzoyl chloride, cyanuric chloride, phosphorus chloride, phosphorus oxychloride, and thionyl chloride [Chem. Eng. News 35(9):87 (1957)]. Reacts, possibly violently, with iodine pentafluoride [Chem. Eng. News 47(12):, 109(1969)]. Vacuum distillation from anhydrous magnesium perchlorate led to an explosion [MCA Case History 1187(1966)]. Violently reactive with fluorinating agents such as silver fluoride [Chem. Eng. News 44(24):7(1956)]. Can explode with sodium hydride [Chem. Eng. News 44(24):7(1966)]. Mixture with methyl bromide resulted in an explosion that shattered the apparatus [NFPA 491M, 1991]. Forms salts with perchloric acid that are explosive when dry [Chem. Abst. 44:p3935d (1950)]. Decomposes when heated above normal boiling point.

Угроза здоровью

The acute toxicity of DMSO by all routes of exposure is very low. Inhalation of DMSO vapor can cause irritation of the respiratory tract, and at higher concentrations may cause vomiting, chills, headache, and dizziness. The material is only slightly toxic by ingestion and may cause vomiting, abdominal pain, and lethargy. Dimethyl sulfoxide is relatively nontoxic by skin absorption, but can cause itching, scaling, and a transient burning sensation. Dimethyl sulfoxide can increase the tendency for other chemicals to penetrate the skin and so increase their toxic effects. Contact of DMSO liquid with the eyes may cause irritation with redness, pain, and blurred vision. Chronic exposure to dimethyl sulfoxide can cause damage to the cornea of the eye. Dimethyl sulfoxide has not been found to be carcinogenic or to show reproductive or developmental toxicity in humans

Воспламеняемость и взрывоопасность

Combustible when exposed to heat or flame (NFPA rating = 1). Carbon dioxide or dry chemical extinguishers should be used to fight DMSO fires.

Химическая реактивность

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.

Биологическая активность

Solvent with wide ranging applications in biological research.

Описание

Диметилсульфоксид (ДМСО) — гигроскопичная бесцветная жидкость без запаха. Один из наиболее часто применяемых полярных апротонных растворителей. Смешивается в любых соотношениях с водой, этанолом, метанолом, диэтиловым эфиром, бензолом, хлороформом, ацетоном. При нагревании выше 150°C начинает медленно разлагаться на диметилсульфид (CH3)2S и диметилсульфон (CH3)2SO2. Диметилсульфоксид малотоксичен и обладает способностью проникать через кожу. Со многими органическими соединениями взаимодействует как окислитель.

Применение

Диметилсульфоксид (ДМСО) находит широкое применение
• как полярный апротонный растворитель (реакционная среда) в химической промышленности и лабораторном органическом синтезе, в том числе для реакций нуклеофильного замещения по SN2 механизму. Диметилсульфоксид хорошо растворяет ацетилен, SO2, полиакрилонитрил. Также, ДМСО используют как растворитель в различных реакциях окисления, в синтезе биоцидных препаратов, пестицидов, инсектицидов;
• в фармацевтической промышленности как реагент для синтеза некоторых препаратов, а также как растворитель для проведения реакций;
• в медицине и косметике — входит в состав препаратов наружного применения. Благодаря своей способности проникать через кожу и малой токсичности используется как переносчик (транспортер) различных веществ;
• входит в состав гидравлических жидкостей и антифризов;
• в молекулярной электронике для обработки печатных плат;
• дейтерированный ДМСО широко используется в ЯМР спектроскопии высокого разрешения как растворитель;
• а также в качестве лекарственного средства.

Экологическая судьба

Most physiological properties of DMSO appear to be related to its penetration properties, its potential to inhibit or stimulate enzymes and to act as a free radical scavenger, and its ability to cause histamine release from mast cells. These properties are largely based on DMSO’s chemical characteristics, including its hydrogen bonding behavior, water affinity, ability to interchange with water in membranes, and ability to react with organic molecules.

хранилище

Dimethyl sulfoxide is reasonably stable to heat,but upon prolonged reflux it decomposes slightly to methyl mercaptan and bismethylthiomethane. This decomposition is aided by acids, and is retarded by many bases. When heated to decomposition, toxic fumes are emitted.
At temperatures between 40 and 60°C, it has been reported that dimethyl sulfoxide suffers a partial breakdown, which is indicated by changes in physical properties such as refractive index, density, and viscosity.
Dimethyl sulfoxide should be stored in airtight, light-resistant containers. The PhEur 6.0 states that glass containers should be used. Contact with plastics should be avoided.

Производство

Основным способом получения Диметилсульфоксида является окисление диметилсульфида. В промышленности этот процесс проводят с использованием азотной кислоты. ДМСО является побочным продуктом целлюлозно-бумажной промышленности.

Методы очистки

This colourless, odourless, very hygroscopic liquid, is synthesised from dimethyl sulfide. The main impurity is water, with a trace of dimethyl sulfone. The Karl-Fischer test is applicable. It is dried with Linde types 4A or 13X molecular sieves, by prolonged contact and passage through a column of the material, then distilled under reduced pressure. Other drying agents include CaH2, CaO, BaO and CaSO4. It can also be fractionally crystallised by partial freezing. More extensive purification is achieved by standing overnight with freshly heated and cooled chromatographic grade alumina. It is then refluxed for 4hours over CaO, dried over CaH2, and fractionally distilled at low pressure. For efficiency of desiccants in drying dimethyl sulfoxide see Burfield and Smithers [J Org Chem 43 3966 1978, Sato et al. J Chem Soc, Dalton Trans 1949 1986]. [Reddy Pure Appl Chem 25 459 1969, Beilstein 1 IV 1277.] Rapid purification: Stand over freshly activated alumina, BaO or CaSO4 overnight. Filter and distil it over CaH2 under reduced pressure (~ 12 mm Hg). Store it over 4A molecular sieves.

Несовместимости

DMSO reacts violently with strong oxidizers, many acyl halides, boron hydrides, and alkali metals. DMSO can form explosive mixtures with metal salts of oxoacids (sodium perchlorate, iron(III) nitrate).

Утилизация отходов

Excess dimethyl sulfoxide 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.

Регуляторный статус

Included in the FDA Inactive Ingredients Database(IVinfusions,SC implants, and topical preparations). Available in the USA as a 50% solution for irrigation in the treatment of interstitial cystitis. Also available in Canada as a 70% solution for use as a topical antifibrotic, and in Germany as a topical gel containing 10% dimethyl sulfoxide for the treatment of musculoskeletal and joint disorders. Included in topical formulations of idoxuridine and diclofenac licensed in the UK.