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DESCRIPTION
Polysorbate 20 (Polyoxyethylene Sorbitan Monolaurate) is a non-ionic surfactant and emulsifier, commonly used in the cosmetic, pharmaceutical, and food industries.
Polysorbate 20 (Polyoxyethylene Sorbitan Monolaurate) is made from sorbitol (a sugar alcohol) that has been esterified with fatty acids, typically lauric acid.
The “20” refers to the average number of ethylene oxide units attached to the sorbitol molecule, which influences its hydrophilic-lipophilic balance
Cas number: 9005-64-5
SYNONYMS
Polysorbate 20,Polyoxyethylene (20) sorbitan monolaurate,7T1F30V5YH,Polyethylene glycol (44) sorbitan monolaurate,Polyethylene glycol (80) sorbitan monolaurate,Polyethylene glycol 4000 sorbitan monolaurate,Polyethylene glycol 500 sorbitan monolaurate,Polyoxyethylene (10) sorbitan monolaurate,Polyoxyethylene (44) sorbitan monolaurate,Polyoxyethylene (75) sorbitan monolaurate,Polyoxyethylene (80) sorbitan monolaurate,Polyoxyethylene 20 sorbitan monolaurate,FEMA No. 2915,POE 20 Sorbitan monolaurate,PSML,Polyethylene glycol 2000 Sorbitan Laurate,Polyoxyethylene (4) sorbitan monolaurate,Sorbimacrogol laurate 300,Sorbitan monolaurate, ethoxylated,20s, Polysorbate,Armotan pml-20,CCRIS 699,DTXSID3031949,Dxewmulse poe-sml,E-432,EC 500-018-3,Emsorb 6915,Glycosperse L-20,Glycosperse L-20X,HSDB 7824,Hodag psml-20,INS NO.432,INS-432,Liposorb L-20,PEG-20 SORBITAN,PEG-40 Sorbitan laurate,POLY(OXY-1,2-ETHANEDIYL) DERIVATIVE,POLYSORBATA 20,POLYSORBATE 20 (EP MONOGRAPH),POLYSORBATE 20 (II),POLYSORBATE 20 (MART.),POLYSORBATE 20 (USP-RS),Peg sorbitan laurate,Peg-20 sorbitan laurate,Poly(oxy-1,2-ethanediyl) derivatives,Polyoxyethylene (40) sorbitan laurate,Polyoxyethylene 20 laurate,Polysorbate 20s,Polysorbatum 20,Protasorb L-20,Sorbitan, monododecanoate, poly(oxy-1,2-ethanediyl) derivatives,Sorbitan, monododecanote, poly(oxy-1,2-ethanediyl) derivatives,Sorbitan, monolaurate, polyoxyethylene derivs.,TWEEN-20,UNII-239B50Y732,UNII-31JQ3WOL8T,UNII-4Z93U4C2WN,UNII-59IO08SBZU,UNII-7T1F30V5YH,UNII-I42X3Q0FMF
Overview of Polysorbate 20
Polysorbate 20, also known as Tween 20, is a nonionic surfactant and emulsifier commonly used in pharmaceuticals, cosmetics, and food products.
It belongs to the group of polysorbates, which are derived from sorbitol (a sugar alcohol) and fatty acids through the process of ethoxylation.
Polysorbate 20 is widely known for its role in stabilizing mixtures that are otherwise immiscible, such as oil and water, thereby improving the texture and stability of formulations.
Definition and Chemical Structure
The chemical name of Polysorbate 20 is Polyoxyethylene (20) sorbitan monolaurate.
It consists of a hydrophilic (water-loving) polyoxyethylene chain and a hydrophobic (oil-loving) fatty acid (lauric acid, C12).
The number 20 in its name refers to the average number of ethylene oxide units attached to the sorbitan molecule, contributing to its emulsifying properties.
The structure has a lipophilic tail (the fatty acid) and a hydrophilic head (the polyoxyethylene chain), making it ideal for emulsification.
Brief History
Polysorbate 20 was first introduced in the mid-20th century as a component of various emulsifying agents.
It gained wide acceptance in industries such as food, cosmetics, and pharmaceuticals due to its effectiveness and relatively mild toxicity profile.
Over time, its application expanded to more complex formulations, especially in pharmaceutical drug delivery systems and vaccine formulations.
Uses in Various Industries
Polysorbate 20 is an essential ingredient in the formulation of many consumer products.
In pharmaceuticals, it is used in emulsions, suspensions, and solubilizing agents for hydrophobic compounds.
In cosmetics, it helps in the formulation of lotions, creams, and other personal care items by preventing the separation of ingredients.
In the food industry, it stabilizes emulsions like salad dressings and ice cream.
Chemical Properties and Structure
Chemical Composition
Polysorbate 20 is composed of a sorbitan backbone that is esterified with lauric acid (C12).
Sorbitan is a dehydrated sugar alcohol that forms the hydrophobic core of the molecule.
This is then reacted with ethylene oxide (a small, highly polar molecule), which adds hydrophilic groups (ethylene oxide units) to the molecule, creating the polyether portion.
The number 20 refers to the average number of ethylene oxide groups added.
Molecular Structure and Formula
The molecular formula of Polysorbate 20 is C58H114O26, which reflects the molecular structure consisting of a central sorbitan molecule with 20 ethylene oxide groups and a lauric acid ester side chain.
The chemical structure can be described as follows:
The sorbitan portion consists of a six-carbon sugar backbone.
The fatty acid group (lauric acid) is attached via an ester bond to the sorbitan molecule.
Polyethylene glycol (PEG) chains are added to the sorbitan molecule, which are responsible for its solubility in water.
Hydrophilic-Lipophilic Balance (HLB) Value
Polysorbate 20 has a HLB value of around 16.7, indicating that it is more hydrophilic (water-loving) than lipophilic (oil-loving).
This high HLB value makes it particularly effective in emulsifying oil and water mixtures, stabilizing aqueous emulsions where the oil phase is dispersed into the water phase.
Comparison with Other Polysorbates
Polysorbate 20 is often compared to other polysorbates, such as Polysorbate 80 and Polysorbate 60.
While Polysorbate 20 has a lower molecular weight and a higher HLB value, Polysorbate 80 (with an HLB of 15) is used for emulsions where a higher oil phase content is present.
Polysorbate 60, with a slightly lower HLB of around 14, is typically employed in more stable emulsions and formulations requiring greater emulsifying power for oilier substances.
Synthesis and Manufacturing
Raw Materials
The key raw materials for synthesizing Polysorbate 20 include:
Sorbitol: A sugar alcohol derived from fruits or synthesized from glucose. It is the starting point for the synthesis of the emulsifier.
Lauric acid: A saturated fatty acid found in coconut oil or palm kernel oil.
It is esterified with sorbitol to form the basic backbone of the polysorbate.
Ethylene oxide: A small, highly reactive compound used in the ethoxylation process to add the polyoxyethylene chains to the sorbitan structure.
Chemical Reaction Steps
The production of Polysorbate 20 involves the following steps:
Esterification: Sorbitol reacts with lauric acid to form sorbitan monolaurate.
This esterification reaction is facilitated by heating and the presence of catalysts.
Ethoxylation: The sorbitan monolaurate is then treated with ethylene oxide under controlled conditions (temperature, pressure) to add the ethylene oxide units.
The number of ethylene oxide units (20 in the case of Polysorbate 20) is controlled by adjusting reaction parameters.
Purification: After the ethoxylation reaction, the product is purified through distillation and filtration to remove any unreacted starting materials and by-products.
Manufacturing Methods
Industrial Scale: The synthesis of Polysorbate 20 is typically carried out on an industrial scale, involving large reaction vessels and continuous or batch processing.
After synthesis, the emulsifier is often mixed with solvents or other excipients to form liquid or semi-solid emulsions.
Laboratory Scale: In small-scale laboratory settings, the ethoxylation process is typically more controlled and may use small reactors to produce specific batches for research and testing.
Quality Control and Testing
To ensure consistency in the final product, quality control measures are taken at various stages of manufacturing.
These include testing for:
Purity: The presence of residual reactants or by-products.
Emulsification efficiency: The ability of the polysorbate to emulsify oil and water mixtures.
Stability: Ensuring that the product maintains its emulsifying properties over time.
Viscosity and color: These properties are monitored to ensure that the final product meets standards for appearance and consistency.
Physical Properties
Color, Appearance, and Solubility
Polysorbate 20 is typically a yellow to amber-colored, viscous liquid. It is highly soluble in water due to its hydrophilic ethylene oxide units but can also be mixed with oils and other lipophilic substances due to its amphiphilic nature.
Melting Point and Boiling Point
Melting point: Polysorbate 20 is generally liquid at room temperature, with a melting point below 0°C, making it suitable for use in both solid and liquid formulations.
Boiling point: Its boiling point is difficult to measure directly since it decomposes before it boils (due to the presence of ethylene oxide), but it remains stable under typical usage conditions.
Viscosity and Stability
The viscosity of Polysorbate 20 can vary depending on concentration and formulation.
It typically has a low viscosity compared to other polysorbates, making it ideal for use in liquid formulations.
Stability: Polysorbate 20 is generally stable in both acidic and basic environments but may degrade under extreme conditions (high temperatures or long-term exposure to light).
Shelf-life and Storage Conditions
To maintain the effectiveness of Polysorbate 20, it should be stored in a cool, dry place, away from direct sunlight.
Typically, the shelf-life is several years when stored in proper conditions, but degradation may occur over time, leading to a decrease in emulsification efficiency.
Applications
Pharmaceutical Industry
Polysorbate 20 plays a crucial role in pharmaceutical formulations, especially for emulsions, oral suspensions, and parenteral (injectable) drugs.
In these applications, it stabilizes drug molecules, ensuring their homogeneity and preventing phase separation.
Emulsions: Polysorbate 20 helps in the formation of stable oil-in-water emulsions for both oral and topical pharmaceutical products.
For example, in topical creams, Polysorbate 20 aids in ensuring that active pharmaceutical ingredients (APIs) are effectively delivered to the skin.
Injectable Formulations: Polysorbate 20 is used in intravenous (IV) medications to solubilize hydrophobic drugs, such as certain hormones and chemotherapy agents, improving their solubility in water.
Vaccine Formulations: Polysorbate 20 is commonly used in the preparation of vaccines.
It helps emulsify and stabilize components like oils and proteins, ensuring that the vaccine remains stable and effective when injected into the body.
Cosmetic Industry
The cosmetics industry is one of the largest consumers of Polysorbate 20, where it serves as an emulsifier, surfactant, and stabilizer in various products.
Skin Care Products: Polysorbate 20 helps to blend water-based and oil-based ingredients in facial cleansers, moisturizers, and sunscreens.
It prevents the separation of oils and water, giving a uniform consistency to emulsions like lotions and creams.
Hair Care: In hair care products, such as shampoos and conditioners, Polysorbate 20 acts as a mild surfactant to cleanse the scalp and hair while emulsifying oils, conditioning agents, and fragrances.
Fragrance Formulation: Polysorbate 20 is also used in fragrances to help dissolve essential oils into alcohol or water solutions, creating stable mixtures that do not separate.
Food Industry
In food processing, Polysorbate 20 is used as an emulsifier and stabilizer to help mix ingredients that would otherwise separate, such as oil and water.
Emulsification: It stabilizes emulsions in products like salad dressings, mayonnaise, and ice cream.
It helps prevent the breaking of the emulsion by improving the uniform distribution of oil droplets in the water phase.
Food Additives: Polysorbate 20 is often included in food products for its ability to maintain texture, prolong shelf life, and ensure that ingredients remain in suspension.
For example, it is used in beverages like fruit juices and sports drinks to prevent ingredient separation.
Regulatory Considerations: Polysorbate 20 is considered generally recognized as safe (GRAS) by the FDA for use in food products, although its concentration is regulated to ensure consumer safety.
Other Industries
Beyond pharmaceuticals, cosmetics, and food, Polysorbate 20 is also utilized in a variety of other industries:
Paint and Coatings: It is used in the formulation of water-based paints and coatings to stabilize pigment dispersions and improve application.
Textile Industry: In the textile industry, Polysorbate 20 acts as a dispersing agent to help process dyes and other chemicals.
Agricultural Products: It is found in pesticide formulations where it aids in emulsifying active ingredients into spray solutions, ensuring uniform application.
Mechanism of Action
Polysorbate 20 functions primarily as an emulsifier and surfactant, with its mechanism rooted in its chemical structure, which has both hydrophobic (fatty acid) and hydrophilic (ethylene oxide) regions.
The behavior of Polysorbate 20 in an emulsion is influenced by these dual properties:
Emulsification Process: In the presence of water and oil, Polysorbate 20 reduces the surface tension between the two phases.
The hydrophilic head of Polysorbate 20 associates with the water phase, while the hydrophobic tail interacts with the oil phase.
This creates a stable interface between the oil and water, forming micelles or droplets that are dispersed evenly.
Solubility and Dispersion: Polysorbate 20 helps disperse hydrophobic substances into water-based systems, such as when it is used in pharmaceutical formulations to solubilize poorly soluble drug compounds, ensuring that they can be effectively absorbed by the body.
Stabilization: It stabilizes emulsions by preventing the coalescence of oil droplets, reducing the tendency of emulsions to "break."
The ethylene oxide groups on Polysorbate 20 create an aqueous layer around the oil droplets, providing steric stabilization and preventing them from aggregating.
Environmental Impact
The environmental impact of Polysorbate 20 is an important consideration, particularly in the context of sustainability and eco-friendly practices.
Biodegradability: Polysorbate 20 is biodegradable under aerobic and anaerobic conditions, meaning it breaks down relatively easily in the environment, particularly in water treatment systems.
Environmental Persistence: While it biodegrades, the rate of degradation can vary depending on environmental conditions such as temperature and microbial activity.
Regulatory Concerns: Regulatory agencies around the world, including the EPA, monitor the discharge of surfactants like Polysorbate 20 into the environment.
Proper disposal methods and treatment processes are necessary to minimize the impact on ecosystems.
Sustainability: There is a growing movement toward using more renewable raw materials in the production of surfactants, including polysorbates. Some companies are exploring bio-based alternatives to petroleum-derived feedstocks for the synthesis of Polysorbate 20.
Regulations and Standards
Polysorbate 20 is subject to a range of regulations in different industries to ensure consumer safety and product quality.
FDA and GRAS: In the U.S., the FDA classifies Polysorbate 20 as a GRAS (Generally Recognized as Safe) substance for use in food and pharmaceuticals.
Specific limits on its concentration exist, depending on the application.
Cosmetic Regulations: In cosmetics, Polysorbate 20 is approved for use as an emulsifier and surfactant in formulations such as lotions, shampoos, and cleansers.
The FDA and the European Medicines Agency (EMA) regulate its use in cosmetics to ensure consumer safety.
European Standards: The European Union has established guidelines for the permissible concentrations of Polysorbate 20 in food and cosmetics, in accordance with the European Food Safety Authority (EFSA) and the Cosmetics Regulation (EC) No 1223/2009.
Recent Research and Developments
Recent research has explored new applications and improved formulations using Polysorbate 20, particularly in drug delivery systems and nanotechnology.
Nanoparticle and Drug Delivery: Studies have shown that Polysorbate 20 can enhance the delivery of poorly soluble drugs by forming nanoparticles that increase drug bioavailability.
These formulations are particularly useful in cancer therapies, where Polysorbate 20 helps deliver chemotherapy drugs more efficiently to target tissues.
COVID-19 Vaccine Formulations: Polysorbate 20 has been integral to the formulation of COVID-19 vaccines, particularly in stabilizing lipid nanoparticles that encapsulate the mRNA used in vaccines like Pfizer-BioNTech and Moderna.
Improved Sustainability: Ongoing research into the environmental impact of surfactants is driving innovations in the synthesis of more eco-friendly variants of Polysorbate 20.
This includes using bio-based feedstocks and reducing the reliance on petroleum-derived chemicals.
Polysorbate 20 is a highly versatile and widely used emulsifier with applications across several industries, including pharmaceuticals, cosmetics, food, and beyond.
Its unique chemical structure, which allows it to stabilize emulsions and solubilize hydrophobic substances, makes it indispensable for many formulations.
While it has an excellent safety profile, its environmental impact and sustainability are areas that are increasingly being addressed by both researchers and manufacturers.
As we move forward, continued innovations in Polysorbate 20 applications and the development of more sustainable alternatives will likely expand its use in cutting-edge technologies such as nanomedicine, gene therapy, and environmentally friendly product formulations.
SAFETY INFORMATION ABOUT POLYSORBATE 20 (POLYOXYETHYLENE SORBITAN MONOLAURATE)
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
