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4,4-Dithiodimorpholine is an aryl dithiol that is prepared by taking a mixture of stannous chloride dihydrate and glacial acetic acid with anhydrous hydrogen chloride.
4,4-Dithiodimorpholine forms a self-assembled monolayer on a variety of surfaces by attaching one thiol group to the surface while the other can create nucleation sites for other functional groups.
4,4-Dithiodimorpholine can be used to functionalize iron nanoparticles (NPs) with the gold shell (Fe−Au) on polyethylene substrate.
CAS Number: 103-34-4
Molecular Formula: C8H16N2O2S2
Molecular Weight: 236.35
EINECS Number: 203-103-0
Synonyms:4,4'-DITHIODIMORPHOLINE, 103-34-4, 4,4-Dithiodimorpholine, Morpholine, 4,4'-dithiobis-, Sulfasan, Sulfasan R, Accel R, 4,4'-Dithiomorpholine, Morpholine disulfide, Morpholino disulfide, 4,4'-Dithiobismorpholine, Dimorpholine disulfide, Dimorpholino disulfide, Bismorpholino disulfide, Deovulc M, Sanfel R, Dithiobismorpholine, Morpholinodisulfide, Vanax A, Disulfide, dimorpholino-, Usaf ek-t-6645, Usaf B-17, Dimorpholine N,N'-disulfide, N,N-Dithiodimorpholine, 4,4'-Dithiobis(morpholine), N,N'-Bismorpholine disulfide, N,N'-Dimorpholine Disulfide, Morpholine, 4,4'-dithiodi-, N,N'-Dithiodimorfolin, DITHIODIMORPHOLINE, 4-(morpholin-4-yldisulfanyl)morpholine, NSC 65239, Dithiobis(morpholine), N,N'-Dithiodimorpholine, DTXSID8026698, M786P489YF, NSC65239, NSC-65239, Vulnoc, DTXCID706698, Di(morpholin-4-yl) disulphide, 4-(4-Morpholinyldisulfanyl)morpholine, CAS-103-34-4, Morpholine, N,N'-disulfide-, CCRIS 8923, N,N'-Dithiodimorfolin [Czech], HSDB 5351, EINECS 203-103-0, 4,4/'-Dithiodimorpholine, BRN 0126214, UNII-M786P489YF, AI3-08625, Sulfazan R, 4-(morpholinodisulfanyl)morpholine, Dimorpholinodisulfide, MFCD00023319, Naugex SD-1, Akrochem accelerator R, Morpholine,4'-dithiodi-, 1,2-dimorpholinodisulfane, Morpholine,4'-dithiobis-, 4,4'-Dithiodimorpholine, N,N'-DimorpholineDisulfide, EC 203-103-0, Bis(4-morpholinyl)disulfide, Morpholine, N,N'-disulfide, N,N'-Dithiobis(morpholine), NCIOpen2_003134, 4-27-00-00613 (Beilstein Handbook Reference), 4,4'-Dimorpholine disulphide, SCHEMBL137538, 4,4'-disulfanediyldimorpholine, CHEMBL582932, HLBZWYXLQJQBKU-UHFFFAOYSA-, MORPHOLINE N,N'-DISULFIDE, DITHIODIMORPHOLINE, 4,4'-, 4-morpholin-4-yldisulfanylmorpholine, Tox21_201775, Tox21_303110, BDBM50414924, STL326287, AKOS015897388, WLN: T6N DOTJ ASS-AT6N DOTJ, 4,4'-DITHIODIMORPHOLINE [MI], 4,4'-DITHIODIMORPHOLINE [HSDB], 4-(4-Morpholinyldisulfanyl)morpholine #, NCGC00249116-01, NCGC00257082-01, NCGC00259324-01, AS-57709, CS-0196466, D0282, NS00006501, E78171, Q27283591, InChI=1/C8H16N2O2S2/c1-5-11-6-2-9(1)13-14-10-3-7-12-8-4-10/h1-8H2, SULFASAN(R) R;Morpholine N,N'-disulfide;N,N'-DIMORPHOLINE DISULFIDE;N,N'-DITHIOBIS(MORPHOLINE);VANAX A;VANAX A FINE GRIND;VANAX A RODFORM;4Mmorpholin-4-yldisulfanylmorpholine
4,4-Dithiodimorpholine can also be coated on the p-doped gallium arsenic (GaAs) substrate for a variety of semiconductor applications.
4,4-Dithiodimorpholine is a synthetic organic sulfur compound that plays a significant role in the rubber and elastomer industries due to its functionality as a sulfur donor and vulcanization accelerator.
It is widely used to enhance the mechanical and thermal properties of rubber products through the formation of cross-linked structures during vulcanization.
4,4-Dithiodimorpholinee consists of two morpholine rings, which are cyclic amines containing oxygen, linked through a disulfide (-S-S-) bond.
This disulfide linkage is central to its role as a sulfur donor in vulcanization reactions.
4,4-Dithiodimorpholine appears as a white to pale yellow crystalline powder that is typically odorless.
4,4-Dithiodimorpholines melting point ranges between 122°C and 125°C, indicating good stability under moderate temperature conditions.
While it is insoluble in water, it dissolves readily in organic solvents like acetone, benzene, and toluene, which makes it suitable for applications in rubber formulations and other industrial processes.
4,4-Dithiodimorpholine is chemically stable under normal conditions but may degrade when exposed to strong oxidizing agents or excessive heat, releasing sulfur-containing byproducts.
4,4-Dithiodimorpholine is primarily used as a vulcanization accelerator and sulfur donor in the production of natural and synthetic rubber materials.
The compound facilitates the formation of sulfur cross-links between rubber polymer chains, which enhances the elasticity, durability, and thermal stability of the final products.
It is a critical ingredient in manufacturing high-performance rubber products such as automotive tires, industrial belts, hoses, and seals, where strength and flexibility are essential.
In addition to its primary application in rubber processing, 4,4-Dithiodimorpholine is also utilized as a curing agent in certain adhesives, coatings, and elastomers, where it contributes to improved mechanical and thermal properties.
The disulfide bond in 4,4-Dithiodimorpholine allows it to act as a controlled sulfur-release agent, making it useful in formulations requiring precise vulcanization or curing processes.
Although 4,4-Dithiodimorpholine is highly valuable for industrial purposes, it must be handled with caution due to its potential health and environmental risks.
Direct contact with 4,4-Dithiodimorpholine can cause irritation, redness, or itching.
Prolonged exposure may lead to sensitization, resulting in allergic skin reactions.
Inhalation of 4,4-Dithiodimorpholine dust or fumes can irritate the respiratory tract, causing coughing, throat discomfort, or shortness of breath, especially in poorly ventilated environments.
While not highly toxic, ingestion or excessive inhalation of 4,4-Dithiodimorpholine may lead to systemic effects, necessitating medical attention.
4,4-Dithiodimorpholine is known to be harmful to aquatic organisms, and its release into water bodies can have long-lasting effects on ecosystems.
It may interfere with the growth and survival of fish, invertebrates, and other aquatic life.
4,4-Dithiodimorpholine does not break down easily in the environment and may persist in soil and water, contributing to contamination if not handled properly.
To ensure safety during the use and handling of 4,4-Dithiodimorpholine, it is essential to follow recommended guidelines and practices:
4,4-Dithiodimorpholineshould wear gloves, protective goggles, and appropriate clothing to minimize skin and eye contact.
Dust masks or respirators are recommended in environments where dust or fumes may be present.
Proper ventilation systems should be implemented in workplaces where 4,4-Dithiodimorpholine is used to prevent the accumulation of airborne particles or vapors, reducing the risk of inhalation exposure.
4,4-Dithiodimorpholine should be stored in a cool, dry, and well-ventilated area, away from direct sunlight, moisture, and incompatible substances like oxidizing agents.
Containers should be tightly sealed to prevent contamination.
4,4-Dithiodimorpholine should be collected carefully to avoid generating dust and disposed of according to local environmental regulations to prevent contamination of soil or water resources.
4,4-Dithiodimorpholine is a highly specialized organic compound prominently used in industrial applications, especially in the rubber industry.
Its unique chemical structure and properties enable it to serve as a sulfur donor, vulcanization accelerator, and cross-linking agent, which are essential for producing high-performance rubber products.
4,4-Dithiodimorpholine also finds applications in adhesives, coatings, and other elastomeric systems that require enhanced mechanical and thermal properties.
4,4-Dithiodimorpholine consists of two morpholine rings (heterocyclic amines with oxygen atoms in the ring) connected by a disulfide (-S-S-) bond.
This disulfide linkage is crucial for its functionality, as it allows the controlled release of sulfur during the vulcanization process, making it a valuable additive for rubber formulations.
4,4-Dithiodimorpholine is an essential industrial chemical, particularly valued for its role in the vulcanization of rubber and elastomers.
Its ability to enhance the mechanical, thermal, and chemical properties of these materials makes it indispensable for applications ranging from automotive to aerospace industries.
However, its potential hazards to health and the environment necessitate careful handling, adherence to safety protocols, and compliance with regulatory requirements.
By implementing appropriate safety measures, 4,4-Dithiodimorpholine can be utilized effectively while minimizing risks to workers and the environment.
Melting point: 124-125°C
Boiling point: 371.7±52.0 °C(Predicted)
Density: 1.32~1.38g/cm3
vapor pressure: 0.004Pa at 25℃
refractive index: 1.6300 (estimate)
storage temp.: Refrigerator
form: powder to crystaline
pka: 0.78±0.20(Predicted)
color: White to Almost white
Specific Gravity: 1.36
Water Solubility:215mg/L at 20.2℃
Merck: 14,3372
InChIKey: HLBZWYXLQJQBKU-UHFFFAOYSA-N
LogP: 2.67 at 22℃
4,4-Dithiodimorpholine is typically found as a white to pale yellow crystalline powder.
Its color can vary slightly based on purity and storage conditions.
4,4-Dithiodimorpholines melting point falls within the range of 122–125°C, which demonstrates its thermal stability under moderate processing temperatures.
4,4-Dithiodimorpholine is insoluble in water, which limits its environmental mobility in aqueous systems.
However, it is soluble in organic solvents like acetone, benzene, and toluene, making it suitable for use in industrial chemical formulations.:
Generally odorless, though it may release a faint sulfuric smell under certain conditions due to partial decomposition or exposure to heat.
4,4-Dithiodimorpholine remains stable under standard conditions but decomposes at elevated temperatures to release sulfur, enabling its use in vulcanization reactions.
4,4-Dithiodimorpholine is primarily used in the rubber industry as a sulfur donor and vulcanization accelerator.
During vulcanization, sulfur bridges (cross-links) form between polymer chains in rubber, which improve the elasticity, strength, and durability of the material.
The controlled release of sulfur from DTDM ensures uniform cross-linking, reducing the risk of over-curing or inconsistencies in the rubber matrix.
Common applications include automotive tires, conveyor belts, industrial hoses, and seals, where enhanced mechanical and thermal properties are critical.
4,4-Dithiodimorpholine is also used in rubber formulations that require resistance to heat, chemicals, and mechanical stress.
4,4-Dithiodimorpholine contributes to the curing and cross-linking of elastomeric adhesives and protective coatings, which improves their strength, flexibility, and adhesion to various substrates.
In specialty elastomer products, 4,4-Dithiodimorpholine provides the necessary thermal and chemical stability, making these materials suitable for demanding applications in aerospace, automotive, and industrial sectors.
4,4-Dithiodimorpholine offers numerous benefits in industrial applications, its handling requires careful attention to potential health and environmental hazards.
Direct contact with 4,4-Dithiodimorpholine may cause skin irritation, redness, or dermatitis, especially with prolonged exposure.
Eye contact can result in irritation, tearing, or discomfort.
Inhalation of 4,4-Dithiodimorpholine dust or vapors can irritate the respiratory system, leading to coughing, throat irritation, or difficulty breathing.
Chronic exposure may pose more severe respiratory risks.
Accidental ingestion of 4,4-Dithiodimorpholine can be harmful, causing nausea, vomiting, or systemic toxicity. Medical attention should be sought in such cases.
Repeated or prolonged exposure may lead to sensitization, causing allergic skin reactions or respiratory issues in susceptible individuals.
4,4-Dithiodimorpholineis classified as toxic to aquatic life, with potential for long-lasting effects on ecosystems if released into waterways.
The compound's low water solubility and persistence in the environment can lead to bioaccumulation, posing risks to aquatic organisms and ecosystems.
To minimize risks associated with 4,4-Dithiodimorpholine, strict safety protocols should be followed during its use and storage:
Use gloves, safety goggles, and protective clothing to prevent skin and eye exposure.
Respiratory protection such as dust masks or respirators should be worn in environments where dust generation or vapor release is likely.
Workspaces where 4,4-Dithiodimorpholine is handled should have adequate ventilation systems to reduce airborne concentrations.
Dust suppression systems may be necessary in areas where the compound is processed in powdered form.
Store 4,4-Dithiodimorpholine in a cool, dry, and well-ventilated area, away from heat, sparks, or open flames.
Containers should be tightly sealed to prevent moisture ingress or contamination.
Spills should be promptly cleaned up using non-sparking tools to avoid generating dust.
Waste and contaminated materials should be disposed of in compliance with local environmental regulations to prevent environmental contamination.
4,4-Dithiodimorpholine is an alkanethiol that forms a self-assembled monolayer (SAM) on a variety of substrates.
4,4-Dithiodimorpholine can be used to form a dithiol ligand that functionalizes and modifies the properties of surfaces.
4,4-Dithiodimorpholine and a small amount of water to the reaction kettle.
After stirring evenly, add sulfur monochloride, gasoline and sodium hydroxide solution dropwise into the kettle at the same time, control the temperature below 10 ℃, and add the sodium hydroxide solution slightly before a carbon chloride dropwise.
After dropping, add a certain amount of water and continue stirring for 30min.
The reactants are then pumped out, and the filtrate is separated from the water phase of gasoline and recovered.
The filter cake is added to the centrifuge and washed with water to be neutral.
After removing the water, 4,4-Dithiodimorpholine is dried to obtain the finished product.
4,4-Dithiodimorpholine forms a SAM on gold nanoparticle by immobilizing the surface atoms, which can be used in opto-electronic and other energy based applications.
Uses Of 4,4-Dithiodimorpholine:
4,4-Dithiodimorpholine can be used as vulcanizing agent and accelerator for natural rubber and synthetic rubber.
The rubber feed of this product does not spray frost, pollution, discoloration and easy dispersion.
The vulcanizates obtained when used in effective and half-effect vulcanization systems have good heat resistance and aging resistance.
Active sulfur can be released at vulcanization temperature, the effective sulfur content is 27%, the operation is safe, the vulcanization speed is slow when used alone, and the use of thiazole, thiuram and dithiocarbamate can increase the vulcanization speed.
4,4-Dithiodimorpholine is especially suitable for butyl rubber.
4,4-Dithiodimorpholine is produced in the manufacture of tires, butyl inner tubes, adhesive tapes and heat-resistant rubber products.
4,4-Dithiodimorpholine is also used as an asphalt stabilizer for vertical highways.
Suitable for natural rubber and synthetic rubber, with the characteristics of heat resistance, fatigue resistance, reduction resistance, no frost spraying, and scorch prevention.
Used as a stain protector for rubber, a vulcanizer (sulfur donor) and accelerator for natural and synthetic rubbers, a fungicide, and a curing agent for poly(fluoroalkoxyphosphazenes).
4,4-Dithiodimorpholine is widely used in the rubber industry as a sulfur donor during the vulcanization process.
It facilitates the formation of cross-links between polymer chains in rubber, enhancing its elasticity, strength, and durability.
This makes it ideal for creating high-performance rubber products.
4,4-Dithiodimorpholine acts as a vulcanization accelerator, speeding up the curing process.
This is especially important in manufacturing rubber products like tires, belts, hoses, seals, and gaskets, where precise control over the curing time and temperature is crucial.
4,4-Dithiodimorpholine is used to enhance the mechanical properties of rubber, such as tensile strength, wear resistance, and flexibility.
It ensures that rubber products can withstand harsh environments, including high temperatures and chemical exposure.
Beyond rubber, 4,4-Dithiodimorpholine is utilized in the production of elastomers, which are used in various applications requiring high flexibility and resistance to wear, such as coatings, seals, and gaskets.
4,4-Dithiodimorpholine is incorporated into specialized adhesives and coatings, particularly in industries where high-performance bonding is required.
It improves the curing process and enhances the adhesion strength of the materials.
In addition to its role in rubber vulcanization, 4,4-Dithiodimorpholine is employed in the cross-linking of other polymers, providing increased stability and resistance to environmental degradation.
In some cases, 4,4-Dithiodimorpholine is used to enhance the properties of plastics, improving their durability and resistance to environmental factors, although its primary applications remain in rubber and elastomer products.
4,4-Dithiodimorpholine is used in various chemical formulations as a cross-linking agent to improve the structural integrity and physical properties of polymers and copolymers.
This helps enhance the heat resistance, chemical resistance, and mechanical strength of materials used in industrial and commercial products.
In the rubber industry, 4,4-Dithiodimorpholine is specifically used as a processing additive in the production of high-performance rubber goods, especially those requiring high resistance to heat, aging, and deformation under stress.
Its ability to accelerate vulcanization while providing precise sulfur release is critical for achieving uniformity in rubber formulations.
4,4-Dithiodimorpholine plays a significant role in tire production, particularly in high-performance tires.
Its function as a sulfur donor accelerates vulcanization, improving the tire's overall durability, traction, and resistance to wear.
The precise control over curing time and temperature helps prevent issues such as cracking or premature failure under high stress conditions.
4,4-Dithiodimorpholine is also used in rubber blends, especially where specific characteristics such as improved mechanical strength, low-temperature flexibility, and resistance to oils and chemicals are required.
4,4-Dithiodimorpholine helps create a more balanced formulation of rubber compounds that perform well across different environmental conditions.
In the production of industrial sealants and gaskets, 4,4-Dithiodimorpholine enhances the mechanical properties of the elastomeric materials, ensuring they provide excellent sealing performance even under extreme conditions such as high temperatures, pressure, or exposure to chemicals.
This makes it useful in automotive, aerospace, and heavy machinery industries.
4,4-Dithiodimorpholine is used in the production of electrical insulation materials, particularly in cables and wires.
4,4-Dithiodimorpholine improves the dielectric properties of the rubber or polymer matrix, helping to create a material that is more effective at resisting electrical breakdowns.
This application is critical in industries where electrical safety and reliability are paramount.
Some specialized coatings, particularly those used in construction or automotive industries, include 4,4-Dithiodimorpholine as part of the formulation.
Its cross-linking properties improve the water resistance, flexibility, and overall durability of coatings, making them more effective in protecting surfaces from environmental degradation.
4,4-Dithiodimorpholineis occasionally used in the formulation of certain agricultural and industrial products that require rubber-based materials.
These may include items like conveyor belts, hoses, and other products exposed to rough conditions where durability and resistance to wear are essential.
In polymer synthesis, 4,4-Dithiodimorpholine can be used to stabilize certain types of polymeric materials.
The compound's ability to form sulfur bridges between polymer chains aids in stabilizing the molecular structure, which can extend the life cycle of the polymer and improve its performance over time.
Safety Profile Of 4,4-Dithiodimorpholine:
4,4-Dithiodimorpholine is considered toxic if ingested, inhaled, or absorbed through the skin.
Prolonged exposure can cause severe adverse health effects, including damage to internal organs, respiratory distress, and nervous system dysfunction.
Acute toxicity can lead to symptoms such as nausea, dizziness, headache, and gastrointestinal disturbances.
Skin contact with 4,4-Dithiodimorpholine can cause irritation, redness, and discomfort. Prolonged or repeated exposure may lead to dermatitis or other skin conditions.
Eye contact with 4,4-Dithiodimorpholine may result in irritation, redness, pain, and potentially damage to the cornea, especially in cases of direct exposure or improper handling.
Dermal sensitization (allergic skin reactions) can occur after repeated exposure.
Individuals working with 4,4-Dithiodimorpholine may develop hypersensitivity, which could cause more severe reactions upon subsequent contact.
Inhalation of 4,4-Dithiodimorpholine vapors or dust can cause irritation to the respiratory tract, leading to coughing, shortness of breath, and throat irritation.
Prolonged inhalation exposure may lead to chronic respiratory issues or worsen pre-existing respiratory conditions, such as asthma.
