ジメチルスルホキシド 化学特性,用途語,生産方法
外観
無色澄明の液体
溶解性
水及び各種有機溶剤に可溶。水、エタノール及びジエチルエーテルに極めて溶けやすい。
解説
C2H6OS(78.14)．(CH3)2S=O．ジメチルスルホキシドは，略称DMSO．ジメチルスルフィドを酸化すると得られる．無色，無臭，吸湿性の液体．融点18.9 ℃，沸点189 ℃(分解)．d420"1.1014．nD20"1.4795．水，エタノール，アセトン，エーテル，ベンゼン，クロロホルムに溶解する．脂肪族炭化水素は溶かさない．石油中の芳香族留分の抽出溶剤，およびアセチレン，二酸化硫黄，二酸化窒素などのガス溶剤，また各種樹脂の溶剤として用いられる．還元されてジメチルスルフィドになり，酸化されてジメチルスルホンを与える．各種の弱い酸化反応の酸化剤として有機合成に広く用いられる．ポリアクリロニトリル，ポリエチレンテレフタラートなどの高分子化合物の溶剤として用いられるほか，穏やかな酸化剤としても用いられる. LD50 19700 mg/kg(ラット，経口)．森北出版「化学辞典（第2版）
用途
分析用溶剤、有機合成溶剤。
用途
繊維の紡糸液、医薬品原料
用途
アクリル繊維、医薬、農薬などの合成、染料、顔料用溶剤、剥離.洗浄剤.
効能
外用抗炎症薬
使用上の注意
不活性ガス封入
説明
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.
化学的特性
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.
天然物の起源
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
使用
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.
定義
ChEBI: A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.
調製方法
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.
一般的な説明
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.
空気と水の反応
Denser than water and miscible in water.
反応プロフィール
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.
健康ハザード
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
燃焼性と爆発性
Combustible when exposed to heat or flame (NFPA rating = 1). Carbon dioxide or dry chemical extinguishers should be used to fight DMSO fires.
化学反応性
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.
生物活性
Solvent with wide ranging applications in biological research.
環境運命予測
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.
貯蔵
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.
純化方法
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.
不和合性
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).
廃棄物の処理
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.
規制状況(Regulatory Status)
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.
ジメチルスルホキシド 上流と下流の製品情報
原材料
準備製品