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CAS Number: 624-92-0
Molecular Weight: 94.20
Beilstein: 1730824
EC Number: 210-871-0
MDL number: MFCD00008561
PubChem Substance ID: 24870743
Properties
Chemical formula: C2H6S2
Molar mass: 94.19 g·mol−1
Appearance: Colorless to yellowish liquid
Density: 1.06 g/cm3
Melting point: −85 °C (−121 °F; 188 K)
Boiling point: 110 °C (230 °F; 383 K)
Solubility in water: 2.5 g/L (20 °C)
Vapor pressure: 3.8 kPa (at 25 °C)
APPLICATIONS
Dimethyl disulfide is used as a food additive in onion, garlic, cheese, meats, soups, savory flavors, and fruit flavors.
Industrially, Dimethyl disulfide is used in oil refineries as a sulfiding agent.
Dimethyl disulfide is also an effective soil fumigant in agriculture, registered in many states in the U.S. as well as globally.
In this capacity, Dimethyl disulfide is an important alternative in replacing methyl bromide, which is being phased out, however less effective than the former.
This pesticide, Dimethyl disulfide is marketed as "Paladin".
Dimethyl disulfide is used to alpha substitute 2-methylfuran-acrolein to produce a food stuff used in concentrations from 0.02 ppm up to 50 ppm.
Dimethyl disulfide is a stable pale yellow liquid which works as an effective product for sulfiding hydroprocessing catalysts because of its high sulfur content and low decomposition temperature.
Most refineries utilize Dimethyl disulfide instead of other sulfur spiking agents for catalyst sulfiding because it has more sulfur per pound than dimethyl sulfide (DMS) or di-tertiary-butyl polysulfide (TBPS).
Once injected to a hydrotreater or hydrocracker, Dimethyl disulfide decomposes to form H2S.
The H2S reacts with the metal oxides on the catalyst, converting them to the active metal sulfide form.
Dimethyl disulfide also works as an effective product for operators in the petrochemicals industry who must protect their steam-cracking coils against the formation of coke and carbon monoxide.
Dimethyl disulfide is utilized in the preparation of 4-(methylthio)phenol which is used in the production of various pesticides.
Dimethyl disulfide and chlorine are reacted with borontrifluoride phenoxide to produce 4-(methylthio)phenol.
Thiophene and Dimethyl disulfide are blended with combustible hydrocarbon fuel gas to impart a gassy odor to the fuel gas.
Dimethyl disulfide (DMDS) may be used to derivatize alkenes for the determination of position of double bond by MS.
Also, Dimethyl disulfide may be used to determine the location of the double-bond position of monounsaturated fatty acids in Campylobacter cryaerophila by combined GC-MS analysis.
Dimethyl disulfide is Used to make other chemicals.
To help the agricultural industry flourish in its efforts to maintain fertile land, grow crops and raise healthy livestock, Dimethyl Disulfide is produced as
agrochemical intermediate.
Dimethyl Disulfide is also used as a flavor and fragrance intermediate, which enriches the aroma and flavor of certain consumer products.
Dimethyl Disulfide (DMDS) is a sulfiding agent, which is used along with a reducing agent such as hydrogen, to transform metal oxide species to a metallic sulfide crystalline phase in situ for hydrotreating catalysts.
For in situ sulfiding, the reaction is performed inside the process unit for complete control and to achieve maximum catalyst activity and safe handling.
Dimethyl Disulfide can also be used as a passivation agent to reduce the layer of coke that forms within furnaces and improve the run length, yield and life of furnaces.
Dimethyl Disulfide (DMDS) is the most commonly used chemical for sulfiding hydrotreating and hydrocracking catalysts.
These hydroprocessing catalysts contain metal oxides that must be converted to the active metal sulfide before they will promote desulfurization and denitrification reactions on hydrocarbon feeds.
The activation process, often called presulfiding, begins with the introduction of Dimethyl Disulfide into a reactor pressurized with hydrogen at a temperature of 370F or higher.
Under these conditions and when exposed to a hydrotreating catalyst, Dimethyl Disulfide rapidly decomposes, forming the H2S required to convert the oxides to metal sulfides.
Note that if no catalyst is present, thermal decomposition of Dimethyl Disulfide to H2S will not occur until the temperature exceeds 1000°F.
Dimethyl Disulfide is also used to passivate furnace tubes in ethylene crackers, although Dimethyl Sulfide (DMS) is used more often for this application.
Dimethyl Disulfide is ideal for sulfiding because of its high sulfur content (68%) and its decomposition temperature range of 360-460F.
At this temperature level, it is much easier to control the reaction exotherm that occurs as metal oxides are transformed to their corresponding sulfide form.
Note that the Dimethyl Disulfide decomposition temperature over a hydrotreating catalyst is dependent on pressure, residence time, and catalyst type.
For example, CoMo catalysts will decompose Dimethyl Disulfide at a lower temperature than NiMo catalysts.
An additional advantage of Dimethyl Disulfide is the by-product of its decomposition, simple methane (CH4), will not cause premature coking of the catalyst bed.
Other spiking agents, such as polysulfides (TBPS), can cause excessive coking during the sulfiding process due to their decomposition by-products.
Dimethyl disulfide is used as an intermediate as well as a food additive in onion, garlic, cheese, meats, soups, savory flavors and fruit flavors.
Dimethyl disulfide is used in oil refineries as a sulfiding agent.
Also, Dimethyl disulfide is used to alfa substitute 2-methylfuran-acrolein to produce food stuff.
Dimethyl disulfide is involved in the preparation of 4-(methylthio)phenol.
Further, Dimethyl disulfide is used to replace methyl mercaptan as a jet fuel additive.
Dimethyl disulfide finds application in artificial flavoring agent and a corrosion inhibitor.
In addition to this, Dimethyl disulfide serves as an effective soil fumigant in agriculture.
DESCRIPTION
Dimethyl disulfide (DMDS) is an organic chemical compound with the molecular formula CH3SSCH3 which is the simplest disulfide.
Dimethyl disulfide is a flammable liquid with an unpleasant, garlic-like odor.
Dimethyl disulfide is a widespread natural odoriferous compound emitted from many sources such as bacteria, fungi, plants and animals.
Dimethyl disulfide is an oxidation product of methanethiol in air.
Along with dimethyl sulfide and dimethyl trisulfide it has been confirmed as volatile compounds given off by the fly-attracting plant known as dead-horse arum (Helicodiceros muscivorus).
These flies are attracted to the odor of fetid meat, and thus help pollinate this plant.
Dimethyl disulfide can be produced by the oxidation of methanethiol, e.g. with iodine:
2 CH3SH + I2 → CH3SSCH3 + 2 HI
Important reactions include chlorination giving methanesulfenyl chloride (CH3SCl), methanesulfinyl chloride (CH3S(O)Cl), and methanesulfonyl chloride (CH3SO2Cl) as well as oxidation with hydrogen peroxide or peracetic acid giving the thiosulfinate methyl methanethiosulfinate (CH3S(O)SCH3).
Dimethyl disulfide (DMDS) is an organic dialkyl disulfide.
Dimethyl disulfide is one of the odorous compounds found on the working face of typical municipal solid waste landfill in China.
Dimethyl disulfide forms adducts with mono-unsaturated acetates by addition across carbon-carbon double bonds.
These adducts are useful to locate the of double bonds in long-chain mono-unsaturated acetates.
Adsorption of DMDS on Au(111) surface has been investigated by the density functional theory (DFT) within a generalized gradient approximation and experimental high-resolution electron energy loss spectroscopy (HREELS) techniques.
Dimethyl disulfide appears as a colorless oily liquid with a garlic-like odor.
Dimethyl disulfide is Denser than water and slightly soluble in water.
Vapor of Dimethyl disulfide is heavier than air.
Dimethyl disulfide May irritate skin and eyes.
Dimethyl disulfide is an organic disulfide that is methane in which one of the hydrogens has been replaced by a methyldisulfanyl group.
Additionally Dimethyl disulfide has a role as a xenobiotic metabolite.
Compared to other sulfiding agents, Dimethyl disulfide has the highest sulfur content, which reduces the amount of product required for converting oxides to active metal sulfides.
Thermally stable with low viscosity, Dimethyl disulfide is suitable for gas- or liquid-phase injection.
Dimethyl disulfide begins to decompose to H2S at low temperatures, so the risks of reducing the metal oxides prior to sulfiding are eliminated.
In addition, Dimethyl disulfide also decomposes in two steps, further minimizing the risk of temperature excursions during sulfiding.
Dimethyl disulfide is Isolated from garlic oil (Allium sativum), also in onion (Allium cepa), ramsons (Allium ursinum), morello cherry, melon, pineapple, strawberry, wheat bread, cocoa, roasted barley, roasted filberts, roasted peanuts, crispbread, American potato chips, soybean and other foodstuffs.
Dimethyl disulfide is a Flavouring ingredient.
Dimethyldisulfide is a volatile organic compound.
Methyl disulfide is occasionally found as a volatile component of normal human breath and biofluids.
Dimethyl disulfide is one of the representative volatile components found in oral malodor.
Dimethyl disulfide concentrations in breath is a practical noninvasive way to assess recent exposure to sulfur compounds in sulfate pulp mills, and therefore it should be applicable to workplaces contaminated.
Dimethyl disulfide, also known as 2,3-dithiabutane, belongs to the class of organic compounds known as dialkyldisulfides.
These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups.
Dimethyl disulfide is a cabbage, citrus, and earthy tasting compound.
Dimethyldisulfide is found, on average, in the highest concentration within a few different foods, such as kohlrabis (Brassica oleracea var. gongylodes), soft-necked garlics (Allium sativum L. var. sativum), and milk (cow).
Dimethyl disulfide has also been detected, but not quantified in, several different foods, such as wild leeks (Allium ampeloprasum), welsh onions (Allium fistulosum), chickens (Gallus gallus), blackberries (Rubus), and evergreen blackberries (Rubus laciniatus).
This could make dimethyldisulfide a potential biomarker for the consumption of these foods.
Dimethyl disulfide is a secondary metabolite.
Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules.
In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites.
Dimethyl disulfide, with regard to humans, has been found to be associated with several diseases such as perillyl alcohol administration for cancer treatment, irritable bowel syndrome, crohn's disease, and nonalcoholic fatty liver disease; dimethyl disulfide has also been linked to the inborn metabolic disorder celiac disease.
Dimethyl disulfide is a type of disulfide (-S-S- bond) compound expressed by the chemical formula CH3SSCH3.
Dimethyl disulfide 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.
Dimethyl disulfide's detection threshold shows 0.002 ppm, which senses a low concentration equivalent to Dimethyl sulfide.
SAFETY AND HANDLING
Due to its low vapor pressure, Dimethyl disulfide is a safe product to handle at high ambient temperatures.
However, Dimethyl disulfide also has a low flash point and should be handled as a flammable material—stored under inert conditions and away from potential ignition sources.
Dimethyl disulfide is a dermal, oral and toxic inhalation material, as well as a marine pollutant.
Also, Dimethyl disulfide may have a slightly unpleasant odor.
Dimethyl disulfide generates methane during the sulfiding operation, which if not handled properly, may require purging and undesired SOx emissions.
Moreover, Dimethyl disulfide is not soluble with water, but will solubilize in both amines and ketones.
Dimethyl disulfide is compatible with both carbon and stainless steel as long as excess water is not present.
Brass and copper connections are not recommended.
Gaskets should be Teflon since Dimethyl disulfide tends to attack rubber and nitrile elastomers.
Household bleach (not pure bleach) is suggested for any necessary clean up.
SYNONYMS
Dimethyl disulfide
Methyl disulfide
Methyldisulfide
Dimethyldisulfide
Methyldithiomethane
2,3-Dithiabutane
624-92-0
METHYL DISULFIDE
Dimethyldisulfide
Disulfide, dimethyl
(Methyldisulfanyl)methan
