ジメチルジスルフィド
ジメチルジスルフィド · メチルジチオメタン · ジメチルペルスルフィド · ジメチルジスルファン · ジメチルペルジスルフィド · 二硫化メチル · 2,3-ジチアブタン · 二硫化ジメチル
識別子と物理属性
| CAS No. | 624-92-0 |
|---|---|
| 分子式 | C2H6S2 |
| 平均分子量 | 94.2 g/mol |
| 単同位体質量 | 93.99109219 g/mol |
| SMILES | CSSC |
| InChIKey | WQOXQRCZOLPYPM-UHFFFAOYSA-N |
| PubChem CID | 12232 |
| ChEMBL | CHEMBL1347061 |
| ChEBI | CHEBI:4608 |
| EC No. | 210-871-0 |
| DTXSID | DTXSID4025117 |
| 現地名 | ジメチルジスルフィド |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 50.6 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 4 |
| 形式電荷 | 0 |
| 複雑度 | 6 |
| 物質分類 | Other Classes -> Sulfur CompoundsFlammable agents - 3rd degree |
| SpringerMaterials Properties | Schoenflies notation |
| 香料 | Fragrance Ingredient (Dimethyl disulfide) -> IFRA transparency List |
| 農薬 | Fungicides, NematicidesActive substance -> EU Pesticides database: Pending |
| LogP（分配係数） | log Kow = 1.77 |
| 臭い | Garlic-likeSulfurousDiffuse, intense onion odorプロピレングリコール中0.10%。硫黄野菜キャベツ玉ねぎ |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.065 at 68 °F (NTP, 1992) - Denser than waterwill sink1.0625 g/cu cm at 20 °CRelative density (water = 1): 1.061.058-1.065 (20 °C)1.0625 @ 20°C |
| 香味料 | EU Flavoring substances |
| Viscosity | 0.62 mPa.sec at 20 °C0.58 mm²/s at 20 °C |
| Color/Form | Yellow liquidColorles to pale-yellow liquid |
| 溶解度 | less than 1 mg/mL at 68 °F (NTP, 1992)Insoluble in waterMiscible with ethanol, ethyl etherCompletely miscible with most organic solventsVery slightly soluble in watersoluble in alcohol and oils3 mg/mL at 25 °C2.7g/リットル<0.1 g/100 mL で 20 ºC |
| 融点 | -85 °C |
| 沸点 | 109 °C(lit.) |
| 蒸気密度 | 3.24 (vs air) |
| 蒸気圧 | 22 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.525(lit.) |
| FEMA | 3536 | DIMETHYL DISULFIDE |
| 引火点 | 76 °F |
| 貯蔵条件 | Flammables area |
| 外観・状態 | 液体 |
| 比重 | 1.0647 (20/4℃) |
| 色 | クリアイエロー |
| においのタイプ | 硫黄の |
| 臭気閾値 | 0.0022ppm |
| 由来生物 | rabbit |
| 爆発限界 | 1.1-16.1%(V) |
| 比熱容量 | Cp(liquid): 1.55 J/(g·K), at 25℃ |
| JECFA Number | 564 |
| BRN | 1730824 |
| ヘンリー定数 | 5.8×10-3 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 誘電率 | 9.7699999999999996 |
| 安定性 | 安定。強塩基、強酸化剤、強還元剤とは相容れない。可燃性。 |
| InChI | 1S/C2H6S2/c1-3-4-2/h1-2H3 |
| InChIKey | WQOXQRCZOLPYPM-UHFFFAOYSA-N |
| SMILES | CSSC |
| LogP（分配係数） | 1.91 at 20℃ |
| CAS データベース | 624-92-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Disulfide, dimethyl(624-92-0) |
| EPAの化学物質情報 | Methyl disulfide (624-92-0) |
化学的特性
colourless to yellow liquid with a very unpleasant smell, insoluble in water, Soluble in ethanol, ethyl ether and acetic acid. It is a strong odor component irritant which is also included in garlic and has been designated as a specific malodorous substances based on the Offensive Odor Control Law. Its detection threshold shows 0.002 ppm, which senses a low concentration equivalent to Dimethyl sulfide.
化学性质
沸点110℃（13mmHg）
安全性と法規制
| GHS 分類 | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P316, P316, P319, P321, P330, P333+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1592) of reports.H225 (17.7%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Disulfide, dimethylRegulation (EC) No 1107/2009 (amended)Disulfide, dimethyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Disulfide, dimethyl are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 22-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13671Disulfide, dimethyl: HSNO Approval: HSR001134 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 輸送ラベル（DOT） | Flammable Liquid Poison |
| 火災危険 | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 10 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | A very dangerous fire hazard when exposed to heat, flame, or oxidizers. |
| 健康有害性 | Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| 有害性の概要 | A mild skin irritant, dimethyl disulfide is toxic by inhalation, skin absorption, and ingestion. Workers are warned by the nauseating odor, but those exposed to high concentrations may experience fatigue, dyspnea, and upper respiratory tract irritation. At lethal concentrations, animals suffer severe lung injury and paralysis of respiratory muscles. [CHEMINFO] Showed weak to moderate sensitizing potential in local lymph node assay (LLNA) of mice |
用途
解説
ジメチルジスルフィド,ニンニク臭の不快臭をもつ可燃性液体．融点－85 ℃，沸点108～109 ℃(100 kPa)．d2041.0647．n20D1.5260．酸化によりメタンスルホン酸を与える．ごみ，し尿，下水などから産出し，天然精油などにも微量含まれている．悪臭防止法で指定されている悪臭物質．森北出版「化学辞典（第2版）
用途
水添脱硫触媒用初期硫化剤、農薬中間体、硫黄の溶剤、チオメチル化剤、オニオン及びキャベツ系食品香料
用途
機器分析等の標準、調製液原料。
説明
Dimethyl disulfide has a diffuse intense onion odor. It is nonlachrymatory. Ironically, although many find its odor objectionable at high concentrations as noted above, when diluted, its aroma has also been described as pleasant. Dimethyl disulfide is often used in combination with other flavor compounds in food products, including baked goods, cheese, frozen dairy products, meat products, soups, savory flavors, fruit flavors, soft candy, gelatin, puddings, and both alcoholic and nonalcoholic beverages.
天然物の起源
Reported found in sour cherry, guava, melon, peach, pineapple, strawberry, cabbage, kohlrabi, onion, garlic, shallot, leek, chive, peas, potato, rutabaga, tomato, parsley, breads, many cheeses, yogurt, milk, egg, fish, meats, hop oil, beer, Scotch whiskey, cognac, grape wines, cocoa, coffee, peanut, peanut butter, pecan, potato chips, oats, soybean, beans, mushrooms, trassi, macadamia nut, mango, cauliflower, broccoli, brussels sprouts, rice, radish, sukiyaki, sake, watercress, malt, wort, krill, southern pea, loquat, sapodilla, shrimp, oyster, crab, crayfish, clam, scallops and squid.
使用
Dimethyl disulfide is used as an intermediate as well as a food additive in onion, garlic, cheese, meats, soups, savory flavors and fruit flavors. It is used in oil refineries as a sulfiding agent. It is used to alfa substitute 2-methylfuran-acrolein to produce food stuff. It is involved in the preparation of 4-(methylthio)phenol. Further, it is used to replace methyl mercaptan as a jet fuel additive. It finds application in artificial flavoring agent and a corrosion inhibitor. In addition to this, it serves as an effective soil fumigant in agriculture.
一般的な説明
A colorless oily liquid with a garlic-like odor. Denser than water and slightly soluble in water. Flash point 40°F. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.
使用用途
ジメチルジスルフィドの主な使用用途は、燃料油などの精製における水添脱硫触媒用初期硫化剤、農薬中間体、合成樹脂の製造過程における溶剤、チオメチル化剤などです。開発研究レベルでは、機器分析等の標準、調製液原料などにも用いられています。 また、ジメチルジスルフィドは、刺激性が強く、ニンニクに似た特有の硫黄臭を持ち、特定悪臭物質に指定されている物質です。一方で、タマネギやキャベツなどの食品用香料として使用されています。加熱調理においてはジメチルジスルフィドおよびジメチルスルフィドの増加により、煮沸臭あるいはキャベツ臭が増して不快に感じます。
製法・合成法
製造方法
Dimethyl disulfide can be prepared by the reaction between imethyl sulfate and sodium sulfide. under stirring, sulfur powder was added into sodium sulfide solution. The above reaction system was heated Up to 80-90℃, after reaction for 1 h, cooled to about 30 ℃. Dimethyl sulfate was dropped into the reaction system and the reaction was continued for 2h. Then, distillation, stratification, Separating waste alkali liquor, then through distillation and final products are prepared.In industry,dimethyl sulfate method is adopted to synthesize dimethyl disulfide.Na2S+S→Na2S2Na2S2+(CH3)2SO4→CH3SSCH3+Na2SO4From magnesium methyl iodide and S2Cl2, or from S2S2 and sodium methyl sulfate; also from methyl bromide and sodium thiosulfate, after which the resulting sodium methylthiosulfate is heated to yield dimethyl disulfide.
純化方法
Pass it through neutral alumina before use. [Trost Chem Rev 78 363 1978, Beilstein 1 IV 1281.]