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DESCRIPTION
Dioctyl sodium sulfosuccinate is a mild surfactant used as a cleans ing agent.
Dioctyl sulfosuccinate sodium salt is a wetting and emulsifying agent that is slowly soluble in water, having a solubility of 1 g in 70 ml of water.
CAS NUMBER
577-11-7
SYNONYMS
Sodium dioctyl sulfosuccinate,Dioctyl sodium sulphosuccinate,Dioctyl sodiosulfosuccinate,Sodium di-n-octyl sulfosuccinate,Sodium bis(octyl)sulfosuccinate,Sodium O,Odioctylsulfosuccinic acid,Sodium sulfosuccinic acid dioctyl ester,Sulfosuccinic acid 1,4-dioctyl ester sodium salt,Dioctyl sulfosuccinate, sodium salt,Texapon DOS,1639-66-3,Butyl-cerumen,DI-N-OCTYL SODIUM SULFOSUCCINATE,Bu-cerumen,Neocol SW 30,Solbaleite,Caswell No. 392I,Elfanol 883,Sodium di-n-octylsulfosuccinate,HSDB 4086,Butanedioic acid, sulfo-, 1,4-dioctyl ester, sodium salt,NSC 7779,EINECS 216-684-0,EPA Pesticide Chemical Code 079027,UNII-4YLY5570Y0,Dioktylester sulfojantaranu sodneho [Czech],4YLY5570Y0,Dioktylester sulfojantaranu sodneho,Succinic acid, sulfo-, 1,4-dioctyl ester, sodium salt,1,4-Bis(n-octyl) sulfobutanedioate, sodium salt,Succinic acid, sulfo-, dioctyl ester, sodium salt,Sulfobutanedioic acid, 1,4-di(n-octyl) ester, sodium salt,DTXSID7041881,NSC-7779,SODIUM DIOCTYL SULFOSUCCINATE [HSDB],Monawet MO-70,dicapryl sodium sulfosuccinate,Monawet MO-70 RP,Monawet MO-84 R2W,SODIUM 1,2-BIS(OCTYLOXYCARBONYL)-1-ETHANESULFONATE,dioctylsulfosuccinic acid sodium salt,AEROSOL SURFACTANT,ALROWET D65,SCHEMBL22809,DTXCID5021881,RCIJACVHOIKRAP-UHFFFAOYSA-M,bis-(2-ethylhexyl) sodium sulfosuccinate,DICAPRYL SODIUM SULFOSUCCINATE [INCI],NS00019454,EN300-22170136,sodium;1,4-dioctoxy-1,4-dioxobutane-2-sulfonate,DI-(2-ETHYLHEXYL) SULFOSUCCINATE, SODIUM SALT,Q27260677,SODIUM 1,4-BIS(OCTYLOXY)-1,4-DIOXOBUTANE-2-SULFONATE
1. INTRODUCTION
Dioctyl sodium sulfosuccinate (DOSS), commonly known as Aerosol OT, is an anionic surfactant that has found diverse applications across industries such as pharmaceuticals, environmental science, and manufacturing.
Surfactants, in general, are compounds that lower the surface tension between two substances, such as between a liquid and a solid or between two liquids.
They are often classified based on their ionic charge: anionic, cationic, nonionic, and amphoteric. DOSS is an anionic surfactant, meaning it has a negatively charged hydrophilic headgroup.
The unique properties of DOSS, which include its ability to emulsify oils and disperse particulate matter, have made it a key ingredient in formulations that require such interactions.
Its most common applications are in cleaning, lubrication, and dispersal of oils, including in products like detergents and oil spill dispersants.
Additionally, DOSS plays a significant role in the pharmaceutical industry as an emulsifying agent and a solubilizer for poorly water-soluble drugs.
This article aims to explore the chemical structure, synthesis, mechanisms of action, toxicity, environmental impact, and various applications of DOSS.
2. CHEMICAL PROPERTIES
2.1 Molecular Formula and Structure
DOSS is chemically known as sodium bis(2-ethylhexyl) sulfosuccinate.
Its molecular formula is C₈H₁₇O₄SNa. The structure of DOSS consists of two octyl groups (C₈H₁₇), which are hydrophobic, attached to a central sulfosuccinate group.
The sulfosuccinate group (–OOCCH₂CH₂SO₃⁻) has a negatively charged sulfonate group, making the compound an anionic surfactant.
The amphiphilic nature of DOSS, with its hydrophobic alkyl tails and hydrophilic sulfonate head, allows it to reduce surface tension effectively between polar and nonpolar substances, facilitating emulsification and solubilization processes.
2.2 Physical Properties
Appearance: DOSS typically appears as a white to light yellow powder or solid. When dissolved in water, it forms a clear to slightly cloudy solution.
Solubility: DOSS is highly soluble in water, which is essential for its role in emulsification and dispersion.
It forms stable aqueous solutions over a wide pH range.
Melting Point: The melting point of DOSS is around 200°C. The compound is stable at ambient temperatures and can remain stable in solutions.
Surface Activity: As a surfactant, DOSS reduces the surface tension of water, allowing it to interact with hydrophobic substances such as oils, greases, and organic compounds.
This property is crucial in its application as an emulsifier.
2.3 Chemical Reactivity
DOSS is chemically stable under normal conditions but can undergo hydrolysis in acidic conditions, leading to the release of the sulfosuccinate anion and the alcohol component.
The compound’s anionic nature allows it to interact effectively with other surfactants or substances with positive charges, enhancing its versatility in formulations.
3. SYNTHESIS OF DOSS
DOSS is typically synthesized through the reaction of a sulfonated alcohol with succinic acid or its derivatives.
The process begins by sulfonating 2-ethylhexanol, a common alcohol used in industrial applications.
This step introduces the sulfonate group, creating a sulfosuccinate ester.
After the esterification, sodium hydroxide is added to neutralize the solution and form the sodium salt of the sulfosuccinate ester.
3.1 Step-by-Step Synthesis
Sulfation of 2-Ethylhexanol: The alcohol (2-ethylhexanol) undergoes a sulfonation reaction using sulfur trioxide (SO₃) or a sulfonating agent in the presence of a solvent.
Esterification: The sulfonated alcohol then reacts with maleic acid or succinic acid in the presence of a catalyst to form the ester linkage.
Neutralization: The final step involves neutralizing the resulting product with sodium hydroxide to form the sodium salt of the sulfosuccinate ester.
3.2 Optimization of Synthesis
The synthesis of DOSS is highly optimized for maximum yield and purity, with careful control over temperature, concentration, and reaction time.
This ensures the desired chemical structure and minimizes byproducts, making the process more efficient and cost-effective.
4. APPLICATIONS OF DOSS
DOSS has a wide range of applications in various industries due to its emulsifying, dispersing, and wetting properties.
Some of the primary areas of use include:
4.1 Pharmaceuticals
DOSS is a widely used emulsifying agent in the pharmaceutical industry.
It helps solubilize hydrophobic drugs, thereby improving their bioavailability and efficacy.
Its ability to form stable emulsions allows it to be used in both oral and topical drug formulations. For example:
Oral Drug Formulations: DOSS is used in oral emulsions to deliver poorly soluble drugs, enhancing their absorption in the gastrointestinal tract.
Topical Applications: In topical formulations, DOSS aids in the dispersion of active pharmaceutical ingredients, ensuring an even distribution across the skin.
4.2 Industrial Applications
Detergents and Cleaners: DOSS is a key ingredient in detergents, industrial cleaners, and degreasers.
It helps break down oils, fats, and other contaminants, making it effective for cleaning machinery and surfaces.
Lubricants: It is used in lubricants, where it improves the stability and performance of oils by dispersing solid particles and reducing friction.
4.3 Environmental Applications
DOSS plays a crucial role in the cleanup of oil spills.
As a dispersant, it breaks up large oil slicks into smaller droplets, increasing the surface area for microbial degradation.
This process helps mitigate the environmental impact of oil spills and accelerates the natural breakdown of hydrocarbons.
4.4 Biomedical Applications
Research into the biomedical applications of DOSS has expanded into drug delivery systems.
It is used in the formulation of micelles that encapsulate hydrophobic drugs, improving their solubility and targeted delivery to specific tissues.
5. MECHANISM OF ACTION
DOSS, as a surfactant, acts by lowering the surface tension between two phases, allowing the interaction of normally immiscible substances.
This occurs due to the compound’s amphiphilic structure:
Hydrophilic Head: The sulfonate group interacts with water, making DOSS soluble in aqueous environments.
Hydrophobic Tail: The alkyl chains (octyl groups) interact with oils, grease, and other nonpolar substances, forming stable emulsions.
In aqueous solutions, DOSS forms micelles, where the hydrophobic tails are oriented inward, while the hydrophilic heads face outward. This structure allows DOSS to solubilize hydrophobic compounds by encapsulating them within the micelle core, enhancing their solubility in water.
6. SAFETY
6.1 Studies
DOSS has been studied for its toxicity in both acute and chronic exposure scenarios.
While it is generally regarded as safe for use in consumer products at low concentrations, higher concentrations or long-term exposure may lead to skin or eye irritation.
However, it is not considered highly toxic when handled properly.
6.2 Safety Guidelines
For safe use in both industrial and pharmaceutical applications, DOSS should be handled according to safety guidelines.
These include using personal protective equipment (PPE) such as gloves and goggles, especially in concentrations higher than typical commercial formulations.
6.3 Regulatory Standards
Regulatory bodies such as the U.S. Environmental Protection Agency (EPA) and the Food and Drug Administration (FDA) have set limits on the use of DOSS in consumer products.
In environmental applications, its use is monitored to ensure minimal ecological impact.
7. ENVIRONMENTAL IMPACT
7.1 Biodegradability
DOSS is biodegradable under natural conditions, breaking down into simpler components through microbial action.
This feature makes it a more environmentally friendly alternative to non-biodegradable surfactants, especially in oil spill dispersants.
7.2 Ecotoxicity
Despite its biodegradability, DOSS can pose risks to aquatic organisms if concentrations are too high.
Studies have shown that, when used in large quantities, it can be toxic to fish and other aquatic species.
Therefore, its use must be controlled and regulated in environmental applications.
8. RECENT RESEARCH AND INNOVATIONS
8.1 Nanomedicine
Recent advancements have explored the use of DOSS in nanotechnology, particularly in drug delivery systems.
DOSS is used to stabilize nanoparticles that can deliver drugs more efficiently, especially in targeting specific tissues.
Its ability to form micelles is beneficial for encapsulating hydrophobic drugs, ensuring their effective delivery.
8.2 Improvement in Oil Spill Dispersants
Ongoing research is focused on improving the efficiency of DOSS-based oil spill dispersants.
Modifications to the molecular structure of DOSS can enhance its ability to break down oil slicks, especially under varying environmental conditions.
9. CONCLUSION
Dioctyl sodium sulfosuccinate (DOSS) is a versatile and essential surfactant with applications spanning pharmaceuticals, industrial processes, and environmental remediation.
Its unique chemical properties enable it to emulsify and disperse hydrophobic substances effectively, making it invaluable in both research and practical applications.
Although DOSS is generally regarded as safe, its use must be regulated to prevent potential toxicity to aquatic life and human health.
With continued advancements in research, DOSS is poised to remain a key compound in various fields, particularly in drug delivery systems and environmental cleanup efforts.
SAFETY INFORMATION ABOUT DIOCTYL SULFOSUCCINATE SODIUM SALT
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
