Dimethyl Sulfoxide
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Product Description
Dimethyl sulfoxide (DMSO), the colorless, odorless liquid with the simple formula (CH₃)₂SO, is a “universal solvent” whose extraordinary polarity, thermal stability and amphiphilicity let it dissolve almost anything, depress the freezing point of water to –60 °C, and release heat on ice; these properties underpin its dominance in petrochemical aromatics extraction, non-toxic antifreeze/de-icing formulations for fuels, coatings and aircraft, and its unrivaled role as a cryoprotectant that safely locks stem cells and whole blood at –200 °C by preventing intracellular ice. The same penetrating power makes it the spinning solvent of choice for acrylic fibers and aerospace-grade carbon fiber, while in medicine it serves as an anti-inflammatory, analgesic carrier that opens transdermal and even anti-cancer drug-delivery routes, earning it the popular epithet “miracle drug.” Continuous-flow synthesis is now propelling greener, safer production to meet surging demand from electronics, agrochemicals and advanced composites, ensuring that this single small molecule remains the connective tissue between heavy industry and the frontiers of life science.
Other Information
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Historical & Commercial Context: First approved for medical use in 1978; widely used in industrial, laboratory, and clinical settings.
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Natural Occurrence: Found in trace amounts in some plants (Basella alba, Manilkara zapota, Vitis vinifera) and as a bacterial metabolite (E. coli).
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Synonyms: Methylsulfinylmethane, DMSO, Rimso-50, Demasorb, etc.
Emerging Research & Innovations
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Photoreforming of Biomass: DMSO enables selective C3–C4 cleavage of glucose to value-added chemicals (e.g., glycerol) under photocatalytic conditions.
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Advanced Hydrogel Fabrication: DMSO-water binary solvents enable high-resolution 3D printing of hydrogels for soft robotics, wearables, and biomedical devices.
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MOF-Composite Photocatalysts: UiO-66@TiO₂ nanocomposites for efficient degradation of volatile sulfur compounds (e.g., DMS) in air purification.
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Homogeneous Polysaccharide Chemistry: Acidic DMSO systems allow dissolution and functionalization of pectin for drug delivery and smart materials.
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Dental Adhesion: DMSO pretreatment improves long-term bonding stability of universal adhesives to eroded dentin.
Synthesis and Production
Dimethyl Sulfoxide (DMSO) is industrially produced primarily by the catalytic oxidation of dimethyl sulfide (DMS). The main industrial synthesis routes include:
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From Methanol and Hydrogen Sulfide (H₂S):
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DMS Synthesis: Methanol reacts with H₂S over a catalyst (e.g., γ-alumina) to produce dimethyl sulfide.
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Oxidation: DMS is oxidized using oxygen or nitrogen dioxide (NO₂), often with nitrogen oxides (NOx) as catalysts.
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Purification: Crude DMSO is refined via vacuum distillation to obtain high-purity product.
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From Dimethyl Sulfate:
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Dimethyl sulfate reacts with sodium sulfide to yield DMS, which is then oxidized and purified as above.
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Key Process Conditions:
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Oxidants: Air/oxygen or nitrogen dioxide.
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Catalysts: Nitrogen oxides (NOx) commonly used in liquid-phase oxidation.
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Temperature: Typically 60–80°C or higher under pressure.
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Purification: Vacuum distillation (boiling point ~189°C at atmospheric pressure).
Related Research:
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Photocatalytic degradation of DMS using UiO-66@TiO₂ nanocomposites has been explored for environmental remediation of sulfurous pollutants.
Uses and Applications
Industrial & Chemical:
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Solvent: “Universal solvent” for polymers, resins, gases, and in organic synthesis (e.g., SN₂ reactions, ylide formation).
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Petrochemicals: Selective solvent for aromatics extraction (e.g., benzene, toluene).
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Antifreeze/De-icing: Used in aviation fuel, coatings, and extreme-temperature fluids.
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Textile & Fiber Production: Solvent for acrylic fiber (e.g., polyacrylonitrile) spinning and carbon fiber precursor processing.
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Electronics: Rinsing agent in semiconductor manufacturing.
Biomedical & Pharmaceutical:
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Cryopreservation: Gold-standard cryoprotectant for cells (stem cells, embryos, tissue) and biologics.
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Drug Delivery: Enhances transdermal/permeation of topical and systemic drugs.
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Therapeutic Agent: Used topically for anti-inflammatory, analgesic, and wound-healing properties (e.g., in arthritis, interstitial cystitis).
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Dentistry: Pretreatment agent to improve adhesive bonding to eroded dentin.
Materials Science & Advanced Manufacturing:
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3D Printing: Co-solvent in vat photopolymerization for high-fidelity hydrogel printing, reducing water evaporation and structural collapse.
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Polymer Chemistry: Solvent for dissolution and homogeneous modification of biopolymers (e.g., pectin derivatives).
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Photocatalysis: Co-reactant or medium in biomass photoreforming (e.g., selective glucose-to-glycerol conversion).
Agricultural & Environmental:
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Pesticide/Fertilizer Formulations: Carrier solvent enhancing foliar absorption.
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Odor Control: Photocatalytic degradation of dimethyl sulfide (DMS) using TiO₂-based composites.
Chemical and Physical Properties
Physical & Chemical Properties:
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Molecular Formula: C₂H₆OS (also written as (CH₃)₂SO)
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Molecular Weight: 78.14 g/mol
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Appearance: Colorless, hygroscopic liquid, essentially odorless (sometimes slight sulfurous/garlic odor).
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Boiling Point: 189°C (372°F)
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Melting Point: 18.45°C (65.3°F)
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Density: 1.101 g/cm³ at 20°C
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Flash Point: 95°C (203°F) open cup
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Solubility: Miscible with water, ethanol, acetone, ether, chloroform, benzene, and most organic solvents.
Unique Functional Properties:
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High Polarity & Hydrogen-Bond Disruption: Acts as a “hydrogen bond breaker,” enabling dissolution of diverse compounds.
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Cryoprotective: Lowers freezing point of aqueous solutions; 40% DMSO/water remains liquid at –60°C.
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Penetration Enhancement: Rapidly penetrates biological membranes, facilitating transdermal drug delivery.
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Thermal Stability: High boiling point and stable under typical processing conditions.
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Co-solvent Capability: Forms binary solvent systems (e.g., with water) to modulate evaporation, viscosity, and polymer dissolution.
Safety and Handling
Hazards:
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Health: May cause skin/eye irritation, stinging, erythema; systemic absorption can produce garlic-like breath odor. High vapor concentrations may lead to headache, dizziness, sedation.
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Flammability: Combustible liquid (flash point 95°C).
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Environmental: Low toxicity but should be contained to prevent environmental release.
Protective Measures:
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PPE: Gloves (nitrile/neoprene), goggles, lab coat; ventilation/local exhaust.
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Storage: Tightly sealed in cool, dry, well-ventilated areas away from oxidizers.
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Spills: Absorb with inert material, collect in container, ventilate area.