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Dimethyl disulfide

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  • Applications of Dimethyl disulfide
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  • Nov 22,2019
Dimethyl disulfide Basic information
Product Name:Dimethyl disulfide
Synonyms:MGC126532;MGC138156;YWHAZ;disulfuredemethyle;methyldithiomethane;Sulfa-hitech;Sulfa-hitech 0382;DIMETHYL DISULFIDE
CAS:624-92-0
MF:C2H6S2
MW:94.2
EINECS:210-871-0
Product Categories:Allium cepa (Onion);Allium sativum (Garlic);Building Blocks;Chemical Synthesis;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);sulfide Flavor;Food additives;Pesticides intermediate;Solvent;Sulfides/Disulfides;Sulfur Compounds;a solvent and pesticide intermediates, fuel and lubricating oil additives
Mol File:624-92-0.mol
Dimethyl disulfide Structure
Dimethyl disulfide Chemical Properties
Melting point -85 °C
Boiling point 109 °C(lit.)
density 1.0625
vapor density 3.24 (vs air)
vapor pressure 22 mm Hg ( 20 °C)
refractive index n20/D 1.525(lit.)
FEMA 3536 | DIMETHYL DISULFIDE
Fp 76 °F
storage temp. Flammables area
solubility 2.7g/l
form Liquid
Specific Gravity1.0647 (20/4℃)
color Clear yellow
Odorat 0.10 % in propylene glycol. sulfurous vegetable cabbage onion
Odor Typesulfurous
explosive limit1.1-16.1%(V)
Odor Threshold0.0022ppm
Water Solubility <0.1 g/100 mL at 20 ºC
JECFA Number564
BRN 1730824
Exposure limitsACGIH: TWA 0.5 ppm (Skin)
Dielectric constant9.7699999999999996
Stability:Stable. Incompatible with strong bases, strong oxidizing agents, strong reducing agents. Flammable.
InChIKeyWQOXQRCZOLPYPM-UHFFFAOYSA-N
LogP1.91 at 20℃
CAS DataBase Reference624-92-0(CAS DataBase Reference)
NIST Chemistry ReferenceDisulfide, dimethyl(624-92-0)
EPA Substance Registry SystemMethyl disulfide (624-92-0)
Safety Information
Hazard Codes F,Xn,N,T+
Risk Statements 11-20/22-36-51/53-36/37/38-26-22-36/37
Safety Statements 26-61-45-38-36/37/39-28A-16-60-57-39-29
RIDADR UN 2381 3/PG 2
WGK Germany 2
RTECS JO1927500
Autoignition Temperature304 °C
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29309070
Hazardous Substances Data624-92-0(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 290 - 500 mg/kg
MSDS Information
ProviderLanguage
DMDS English
SigmaAldrich English
ALFA English
Dimethyl disulfide Usage And Synthesis
DescriptionDimethyl 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.
Chemical Propertiescolourless 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.
OccurrenceReported 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.
UsesIndustrially, Dimethyl disulfide is also used as a sulfiding agent to catalyze reactions in oil refineries and other industries. It has a low flash point of 16 ℃ (61 °F) that presents fire hazards during refinery usage. Due to its strong odor and low flash point, Dimethyl disulfide typically requires storage under nitrogen pressure in closed containers.
Dimethyl disulfide has a sulfurous odor similar to that of garlic and decaying fish. Because of the distinctive odor of sulfur compounds, similar to DMDS, they are often added to natural gas and propane to warn of leaks and protect people. Therefore, the odor of a DMDS fumigation can be mistaken for a gas leak. DMDS has an odor threshold of approximately 7 ppb, which is about 8 times less than the health‐based level considered by the EPA to be safe (55 ppb).
UsesDimethyl 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.
PreparationDimethyl 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+Na2SO4
From 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.
DefinitionChEBI: Dimethyl disulfide is an organic disulfide that is methane in which one of the hydrogens has been replaced by a methyldisulfanyl group. It has a role as a xenobiotic metabolite.
Aroma threshold valuesDetection: 0.16 to 1.2 ppb. Recognition: 90 ppb
General DescriptionA 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.
Air & Water ReactionsHighly flammable. Slightly soluble in water.
Reactivity ProfileDMDS is a reducing agent. A dangerous fire hazard when exposed to oxidizing materials. Emits toxic fumes of oxides of sulfur when heated to decomposition or on contact with acids [Sax, 9th ed., 1996, p. 1320].
Health HazardMay cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Fire HazardHIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and ExplosibilityHighly flammable
Safety ProfilePoison by inhalation. A very dangerous fire hazard when exposed to heat, flame, or oxidzers. Can react vigorously with oxiduing materials. See also SULFIDES.
Potential ExposurePrimaryIrritant. This material may be used as an organicintermediate
First aidIf this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
storageColor Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with Dimethyl disulfide you should betrained on its proper handling and storage. Before enteringconfined space where this chemical may be present, checkto make sure that an explosive concentration does not exist.Store in tightly closed containers in a cool, well-ventilatedarea away from any form of moisture, oxidizers, acids.Metal containers involving the transfer of this chemicalshould be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers toprocess containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Useonly nonsparking tools and equipment, especially whenopening and closing containers of this chemical. Sources ofignition, such as smoking and open flames, are prohibitedwhere this chemical is used, handled, or stored in a mannerthat could create a potential fire or explosion hazard.Wherever this chemical is used, handled, manufactured, orstored, use explosion-proof electrical equipment andfittings.
ShippingThis compound requires a shipping label of“FLAMMABLE LIQUID.” It falls in Hazard Class 3 andPacking Group II.
Purification MethodsPass it through neutral alumina before use. [Trost Chem Rev 78 363 1978, Beilstein 1 IV 1281.]
Toxicity evaluationVery little information is available on mechanism of toxicity. Although the authors of one experimental animal study suggested that methyl disulfide toxicity resembles that of hydrogen sulfide, it is not at all clear that cytochrome oxidase inhibition can result from methyl disulfide exposure. Mechanistically hydrogen sulfide is classified as a chemical asphyxiant because of its known ability to disrupt electron transport and oxidative phosphorylation by interaction with the enzyme cytochrome oxidase. Other sources classify methyl disulfide a simple asphyxiant, which means that it is nonreactive with enzymes or other cell components and simply displaces oxygen in the air. Some information indicates that neurotoxicity to insects results when methyl disulfide disrupts calcium-activated potassium channels in insect pacemaker neurons.
IncompatibilitiesForms explosive mixture with air.Contact with water or acids forms flammable and toxicvapors of hydrogen sulfide. Contact with oxidizing materials or acids can cause a violent reaction.
Tag:Dimethyl disulfide(624-92-0) Related Product Information
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