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ALLYL ALCOHOL ALKOXYLATE

Allyl alcohol alkoxylates are versatile compounds used as nonionic surfactants in detergents and cleaning products, helping to reduce surface tension and enhance the removal of dirt and oil.
Allyl alcohol alkoxylates are critical in the textile industry, where they enhance fabric softness and dye uptake through their surfactant properties.
In polymer and resin production, allyl alcohol alkoxylates provide precise control over molecular weight and hydrophilicity, which is crucial for creating high-performance adhesives, coatings, and sealants.

CAS Number: 107-18-6
EC Number: 203-429-5
Chemical Formula: C₃H₅OH
Molecular Weight: 58.08 g/mol

Synonyms: Allyl alcohol alkoxylate, ALLYL ALCOHOL 20 EO 10 PO, Poly(ethylene oxide propylene oxide) mono allyl ether, polyalkylene glycol, PAG, Poly(ethylene oxide propylene oxide) monoallyl ether, Allyl polyoxyethylene polyoxypropylene ether, Allyl Alcohol EO PO, Allylglylcol alkoxylate, Polyethylene-Polypropylene Glycol Monoallyl Ether, EO-PO-Monoallyl Ether , Oxirane, methyl-, polymer with oxirane, mono-2-propenyl ether,  Oxirane, methyl-, polymer with oxirane, mono-2-propenyl ether,  Oxirane, 2-methyl-, polymer with oxirane, mono-2-propen-1-yl ether,  Oxirane, methyl-, polymer with oxirane, mono-2-propenyl ether (EO + PO), ADUXOL NA 2140, Pluriol A 46 R, Pluriol A 750 R, Bisomer CA 041 ME, RHODASURF AAE-10 E, Polyglykol A 32/550, Emulsogen RAL 100, Emulsogen V 5127, Polyglykol A 20/10, Polyglykol A 20-20 , Pluriol A 010 R, Pluriol A 11 RE, Pluriol A 13 R, Pluriol A 22 R, Pluriol A 23

Allyl alcohol alkoxylate refers to a class of chemical compounds derived from the reaction of allyl alcohol with alkylene oxides, typically ethylene oxide or propylene oxide, through a process called alkoxylation.
Allyl alcohol (C₃H₅OH) is a small organic molecule featuring a hydroxyl group (-OH) attached to an allyl group (-CH₂CH=CH₂), which makes it a versatile starting material for various chemical reactions.

Alkoxylation, the process in which alkoxide groups are added to the molecule, transforms the chemical structure of allyl alcohol, modifying Allyl alcohol alkoxylate's solubility, surface activity, and reactivity.
The result is a series of alkoxylated compounds with properties suited for specific industrial applications.

Allyl alcohol alkoxylates can act as nonionic surfactants, meaning they help reduce surface tension between liquids or between a liquid and a solid, making them useful in applications such as detergents, emulsifiers, dispersing agents, and wetting agents.
These compounds are often employed in industries ranging from textiles to personal care products, as well as in agrochemicals and coatings.

Additionally, Allyl alcohol alkoxylates can serve as intermediates in the synthesis of polymers, resins, and various other chemical formulations, offering flexibility and control over molecular weight and hydrophilicity, depending on the degree of alkoxylation.
Their ability to modify surface properties and enhance solubility makes them crucial components in many formulations where interaction between hydrophobic and hydrophilic phases is necessary for optimal performance.

Allyl alcohol alkoxylate refers to a class of chemical compounds that are formed by the alkoxylation of allyl alcohol.
Alkoxylation is a chemical process in which alkoxide groups (typically derived from ethylene oxide or propylene oxide) are added to a compound.
This results in molecules with specific properties that can be useful in various industrial applications, such as surfactants or intermediates in polymer production.

Allyl alcohol alkoxylate is a monoallyl ether of ethylene/polyethylene oxides with an average molecular weight of 1500 g/mol. 
Allyl alcohol alkoxylate can be used in various applications, including Laquers, Cleaning Products, Industrial and Automotive Chemicals, Metalworking and Cooling Fluids, Polishes and Floor Maintenance Products, and PU Foam stabilizers.

Allyl alcohol alkoxylate’s applications include surface-active compounds such as paint additives, PU foam stabilization, the manufacture of water-soluble or water-dispersible paints, silicone chemistry, and hydrophilic modification of polymers in general.
Other applications of Allyl alcohol alkoxylate include their use in combination with nitrites for corrosion protection (as an additive to hydraulic cement and cement for steel-reinforced concrete), in paper bleaching (as a delignifying agent), and in the pharmaceutical industry to enhance the biocompatibility of polymers.

Allyl alcohol alkoxylate is incorporated into various polymers to provide the pendant hydroxyl group for crosslinking reaction. 
The polymers are prepared by a bulk free radical polymerization process in which the allyl monomer is charged into the reactor before the polymerization starts, and the vinyl comonomers and the initiator are gradually fed into the reactor at the polymerization temperature.

Allyl alcohol alkoxylate is a critical raw material for various silicons and silicon oils. 
The allylic group is reacted via transition-metal catalyzed hydrosilylation reaction with the Si-H-moiety at the silicon backbone. 

Introducing the ethylene oxide into the silicone alters Allyl alcohol alkoxylate's properties, adding a hydrophilic component. 
The modified silicones are used as emulsions for various applications, e.g., cosmetics or defoamers.

Allyl alcohol alkoxylate can be considered a high molecular alcohol with an allylic function and, therefore, displays typical chemical reactions of alcohols as well as of the allylic group. 
Monoallyl Polyalkylene Glycols generally contain less than 10 ppm residual alkali ions and are, therefore, suitable for polyurethane and hydrosilylation applications.

Alcohol ethoxylates (FAEs) are the products of choice for the replacement of nonylphenol  ethoxylates (NPEs).
The performance properties of these non-ionic surfactants can be adjusted by the alcohol selection and by the length of the hydrophilic polyethylene glycol chain.
In comparison to NPEs, alcohol ethoxylates are usually more biodegradable and their degradation products are unobjectionable in terms of their aquatic toxicity.

Uses of Allyl Alcohol Alkoxylate:
Allyl alcohol alkoxylates are versatile compounds widely used across various industries due to their surfactant properties and role as intermediates in chemical formulations.
In the detergent and cleaning industry, they act as nonionic surfactants, helping reduce surface tension to enhance the removal of dirt and oil.

They also serve as emulsifiers in cosmetics, lotions, and creams, ensuring uniform consistency and stability.
In industries like paints and coatings, these alkoxylates function as dispersing agents, improving the even distribution of particles, while in the textile industry, they improve fabric softness and dye uptake.

Additionally, they play a significant role in agriculture, where they enhance the effectiveness of pesticides by improving their spread and wetting properties on plant surfaces.
Allyl alcohol alkoxylates are also crucial in polymer and resin production, allowing precise control over molecular weight and hydrophilicity, which is beneficial for creating adhesives, coatings, and sealants.

Other uses include their application in personal care products like shampoos and conditioners, the oil and gas industry for drilling fluids, and as plasticizers in the production of flexible plastics such as PVC.
Their adaptability makes them valuable in a wide range of formulations across industries.

Allyl alcohol alkoxylates have a wide range of industrial uses due to their versatile chemical properties, particularly as surfactants and intermediates in various formulations. Below are some key applications:

Surfactants:

Detergents:
Allyl alcohol alkoxylates are commonly used as nonionic surfactants in laundry and dishwashing detergents.
Their ability to reduce surface tension helps in the effective removal of dirt and oils.

Emulsifiers:
They are used in formulations that require the mixing of water and oil, such as in cosmetics, lotions, and creams, ensuring uniform texture and stability.

Wetting Agents:
These compounds enhance the spread of liquids over surfaces, improving the effectiveness of cleaning products and coatings.

Dispersing Agents:
In applications like paints, inks, and pigments, Allyl alcohol alkoxylates help to evenly distribute particles in liquid solutions, preventing clumping and sedimentation.
This improves the quality and consistency of the final product.

Polymer and Resin Production:
They serve as intermediates in the production of polymers and resins, where they contribute to the control of molecular weight and hydrophilic/hydrophobic balance.
These polymers can be used in adhesives, coatings, and sealants.

Textiles and Fibers:
Allyl alcohol alkoxylates are utilized in the textile industry as finishing agents, improving fabric softness, durability, and dye uptake.
They also act as antistatic agents to reduce static cling in fabrics.

Agrochemicals:
In agriculture, these compounds are used as adjuvants in pesticide formulations, enhancing the effectiveness of herbicides, insecticides, and fungicides by improving their wetting and spreading properties on plant surfaces.

Personal Care Products:
Due to their mild nature, they are used in shampoos, conditioners, and skin-care products as emulsifiers or conditioning agents, helping to stabilize formulations and improve texture.

Coatings and Paints:
Allyl alcohol alkoxylates improve the flow and leveling properties of coatings and paints.
They help achieve smooth application and enhance the finish quality by preventing imperfections.

Oilfield Chemicals:
In the oil and gas industry, they are used in formulations for drilling fluids, where they improve lubrication and reduce friction in drilling operations.
They also aid in the emulsification of oil-based fluids.

Plasticizers:
In the production of plastics, Allyl alcohol alkoxylates can be used as plasticizers, enhancing the flexibility and durability of materials like PVC.

Applications of Allyl Alcohol Alkoxylate:
Allyl alcohol alkoxylate can be used for a wide variety of chemical reactions, which usually result in hydrophilic modification and improved compatibility with water of the end products. 
The most helpful reaction in silicon chemistry is the addition of the Si-H function to the allylic group of Allyl alcohol alkoxylate via hydrosilylation
This improves the hydrophilic properties of silicon polymers, which are widely used in paint and defoamer formulations.

Applications of Allyl alcohol alkoxylate include surface-active compounds such as paint additives, PU foam stabilization, manufacture of water-soluble or water-dispersible paints, silicone chemistry, and hydrophilic modification of polymers in general.
Other applications of Allyl alcohol alkoxylate include their use in combination with nitrites for corrosion protection (as an additive to hydraulic cement and cement for steel-reinforced concrete), in paper bleaching (as a delignifying agent), and in the pharmaceutical industry to enhance the biocompatibility of polymers.

Allyl alcohol alkoxylate is incorporated into various polymers to provide the pendant hydroxyl group for crosslinking reaction. 
The polymers are prepared by a bulk free radical polymerization process in which the allyl monomer is charged into the reactor before the polymerization starts, and the vinyl comonomers and the initiator are gradually fed into the reactor at the polymerization temperature.

Allyl alcohol alkoxylate is a critical raw material for various silicons and silicon oils. 
The allylic group is reacted via transition-metal catalyzed hydrosilylation reaction with the Si-H-moiety at the silicon backbone. 

Introducing the ethylene oxide into the silicone alters Allyl alcohol alkoxylate's properties, adding a hydrophilic component. 
The modified silicones are used as emulsions for various applications, e.g., cosmetics or defoamers.

Allyl alcohol alkoxylate can be considered a high molecular alcohol with an allylic function and, therefore, displays typical chemical reactions of alcohols as well as of the allylic group. 
Monoallyl Polyalkylene Glycols generally contain less than 10 ppm residual alkali ions and are, therefore, suitable for polyurethane and hydrosilylation applications.

Allyl alcohol alkoxylate can be used for a wide variety of chemical reactions, which usually result in hydrophilic modification and improved compatibility with water of the end products. 
The most helpful reaction in silicon chemistry is the addition of the Si-H function to the allylic group of Allyl alcohol alkoxylate via hydrosilylation reaction. 
This improves the hydrophilic properties of silicon polymers, which are widely used in paint and defoamer formulations.

Other Applications:
Additive for Laquers
Cleaning Products
Industrial and Automotive Chemicals
Metalworking and Cooling Fluids
Polishes and Floor Maintenance Products
PU Foam stabilizer

Features of Allyl Alcohol Alkoxylate:

Nonionic Surfactant:
These compounds do not carry a charge in solution, making them compatible with both ionic and nonionic systems.

Alkoxylation Tailorability:
The degree of alkoxylation (addition of ethylene or propylene oxide units) can be adjusted to create customized properties, such as hydrophilicity or hydrophobicity.

Emulsifying Capability:
They effectively stabilize emulsions, facilitating the mixing of oil and water phases in formulations.

Wetting Agent:
Allyl alcohol alkoxylates reduce surface tension, enabling liquids to spread more easily over surfaces.

Dispersing Agent:
These compounds help disperse solid particles evenly in liquids, preventing clumping or sedimentation.

Mildness:
They exhibit low toxicity and irritation, making them suitable for use in personal care and household products.

Thermal Stability:
They maintain their properties even under varying temperatures, ensuring consistency in high-temperature applications.

Solubility Modulation:
Their solubility in water or organic solvents can be tailored based on the number of ethylene or propylene oxide units added during synthesis.

Production of Allyl Alcohol Alkoxylate:
The production of Allyl alcohol alkoxylates involves the chemical reaction of allyl alcohol with alkylene oxides (such as ethylene oxide or propylene oxide) in a process known as alkoxylation.

Here’s an overview of the production process:

Raw Material Preparation:

Allyl Alcohol (C₃H₅OH):
This is the primary starting material, a small organic compound with a hydroxyl group (-OH) attached to an allyl group (-CH₂CH=CH₂).

Alkylene Oxides:
The most commonly used are ethylene oxide (EO) and propylene oxide (PO).
The choice and ratio of alkylene oxide determine the properties of the final alkoxylate product, such as solubility, molecular weight, and hydrophilic-lipophilic balance (HLB).

Alkoxylation Reaction:

Reaction Setup:
The reaction typically takes place in a reactor where Allyl alcohol alkoxylate is combined with the chosen alkylene oxide.
This process is usually carried out under controlled conditions of temperature and pressure, using a catalyst.

Catalysts:
Common catalysts include alkali metal hydroxides (e.g., potassium hydroxide) or acid catalysts.
These catalysts speed up the reaction by enabling the alkylene oxide to open its ring structure and react with the hydroxyl group of Allyl alcohol alkoxylate.

Process Control:
The reaction can be controlled by adjusting the number of moles of alkylene oxide added, which determines the degree of alkoxylation.
The reaction may be stopped at specific points to tailor the properties of the final product.

Product Formation:
After the alkoxylation reaction, the product formed is an alkoxylated allyl alcohol.
Depending on the degree of alkoxylation, the product may have varying hydrophilic or hydrophobic characteristics.

Post-Reaction Processing:
Once the reaction is complete, the product may undergo purification steps, such as neutralization (to remove any leftover catalyst) and drying (to remove water or solvents).
Sometimes, further chemical modifications may be done to suit specific applications.

Quality Control:
The final product undergoes quality testing to ensure Allyl alcohol alkoxylate meets the required specifications for its intended use, including tests for molecular weight, viscosity, solubility, and purity.

Packaging and Distribution:
The final Allyl alcohol alkoxylate product is packaged and distributed to various industries for use in detergents, surfactants, polymers, and more.

Occurence of Allyl Alcohol Alkoxylate:
Allyl alcohol alkoxylate occurs naturally in small amounts in various plants and essential oils.
However, Allyl alcohol alkoxylate is not commonly found in significant quantities in nature and is primarily produced synthetically for industrial use.

Here’s a breakdown of Allyl alcohol alkoxylate's natural occurrence and synthetic production:

Natural Occurrence:

Essential Oils:
Allyl alcohol alkoxylate can be found in trace amounts in essential oils such as mustard oil and garlic oil.
In these oils, Allyl alcohol alkoxylate is often present as a component contributing to the characteristic odors and flavors.

Plants:
Allyl alcohol alkoxylate is also found in small quantities in various plants, including some herbs and vegetables.
Allyl alcohol alkoxylate's presence in nature is generally limited and is often associated with specific plant families known for their volatile compounds.

Synthetic Production:
Due to its limited natural occurrence, Allyl alcohol alkoxylate is predominantly produced synthetically.
The primary methods of synthesis involve:

Oxidation of Allyl Bromide:
Allyl bromide can be oxidized to produce Allyl alcohol alkoxylate.

Hydrolysis of Allyl Chloride:
Allyl chloride undergoes hydrolysis to yield Allyl alcohol alkoxylate.

Direct Synthesis:
Allyl alcohol alkoxylate can also be synthesized from propylene or allyl chloride via various chemical processes.

Industrial Relevance:
Given its limited natural sources, the commercial production of Allyl alcohol alkoxylate focuses on synthetic methods to meet the demand for its use in chemical manufacturing, particularly for producing Allyl alcohol alkoxylates and other derivatives.

History of Allyl Alcohol Alkoxylate:
The history of allyl alcohol and its derivatives, including Allyl alcohol alkoxylates, reflects significant advancements in organic chemistry and industrial synthesis.
Allyl alcohol alkoxylate itself was first discovered in 1856 by French chemist Auguste Cahours, who identified it as a key compound derived from allyl compounds.

Over the early 20th century, Allyl alcohol alkoxylate became an important starting material for various chemical processes, including the production of glycerol.
The development of the alkoxylation process in the 1930s and 1950s marked a major milestone, enabling the large-scale synthesis of alkoxylated compounds.

This process involved reacting Allyl alcohol alkoxylate with ethylene or propylene oxides to produce alkoxylates, which are valuable as nonionic surfactants and intermediates in various industrial applications.
By the mid-20th century, Allyl alcohol alkoxylates had become integral to the formulation of detergents, emulsifiers, and other specialty chemicals, leveraging their unique properties to enhance product performance across multiple industries.

Handling and Storage of Allyl Alcohol Alkoxylate:

Handling:

Avoid Inhalation:
Ensure good ventilation when handling Allyl alcohol alkoxylate to avoid inhaling vapors.

Avoid Skin and Eye Contact:
Use appropriate protective equipment to prevent skin and eye contact.

Avoid Ignition Sources:
Since Allyl alcohol alkoxylate is flammable, keep away from open flames, sparks, and heat sources.

Use Proper Equipment:
Use equipment and containers that are compatible with Allyl alcohol alkoxylate and ensure they are properly labeled.

Storage:

Temperature:
Store in a cool, well-ventilated area away from sources of heat or direct sunlight.

Containers:
Use tightly sealed containers to prevent evaporation and contamination.
Containers should be made of materials compatible with Allyl alcohol alkoxylate.

Separation:
Keep away from incompatible materials such as strong oxidizers and acids.

Ventilation:
Ensure proper ventilation in storage areas to prevent the buildup of vapors.

Stability and Reactivity of Allyl Alcohol Alkoxylate:

Stability:

Chemical Stability:
Allyl alcohol alkoxylate is generally stable under normal conditions of use and storage.

Decomposition:
May decompose upon exposure to heat or light, releasing toxic fumes.

Reactivity:

Incompatibilities:
Reacts violently with strong oxidizing agents and acids.

Polymerization:
Can undergo polymerization when exposed to heat or light; inhibitors may be required to prevent polymerization in storage.

Conditions to Avoid:
Avoid exposure to high temperatures, light, and incompatible chemicals.

First Aid Measures of Allyl Alcohol Alkoxylate:

Inhalation:

Move to Fresh Air:
Remove the person from the contaminated area to fresh air immediately.

Seek Medical Attention:
If symptoms persist or there is difficulty breathing, seek medical attention.

Skin Contact:

Remove Contaminated Clothing:
Take off any contaminated clothing and rinse the affected skin with plenty of water.

Wash Skin:
Wash the affected area thoroughly with soap and water.

Seek Medical Advice:
If irritation or burns develop, seek medical advice.

Eye Contact:

Rinse Immediately:
Flush the eyes with plenty of water for at least 15 minutes, holding the eyelids open.

Seek Medical Attention:
If irritation persists or vision is affected, seek medical attention immediately.

Ingestion:

Do Not Induce Vomiting:
Do not induce vomiting unless directed by a medical professional.

Rinse Mouth:
Rinse the mouth with water.

Seek Medical Help:
Get medical help immediately and provide details of the exposure.

Firefighting Measures of Allyl Alcohol Alkoxylate:

Firefighting Equipment:

Fire Extinguishers:
Use alcohol-resistant foam, dry chemical, or carbon dioxide (CO₂) extinguishers.

Water:
Do not use water directly on Allyl alcohol alkoxylate fires as it may spread the fire.

Firefighting Procedures:

Evacuate Area:
Ensure that the area is evacuated and restrict access until the fire is out.

Cool Containers:
Use water to cool exposed containers and prevent explosions or rupture.

Protective Gear:
Wear self-contained breathing apparatus (SCBA) and full protective clothing.

Hazardous Combustion Products:

Decomposition Products:
May produce toxic gases such as carbon monoxide and carbon dioxide when burned.

Accidental Release Measures of Allyl Alcohol Alkoxylate:

Personal Precautions:

Evacuate Area:
Evacuate and keep people away from the spill area.

Protective Equipment:
Wear appropriate personal protective equipment (PPE), including gloves and eye protection.

Containment and Cleanup:

Contain Spills:
Use barriers or absorbent materials to contain and prevent the spread of the spill.

Absorb Spills:
Absorb spills with materials such as sand, earth, or commercial absorbents.

Dispose of Waste:
Collect the absorbed material and dispose of Allyl alcohol alkoxylate in accordance with local regulations.

Environmental Precautions:

Prevent Runoff:
Prevent the spill from entering drains, waterways, or soil.

Notify Authorities:
Report large spills or environmental releases to appropriate authorities.

Exposure Controls/Personal Protective Equipment of Allyl Alcohol Alkoxylate:

Exposure Limits:

Occupational Exposure Limits:
Follow local regulatory guidelines for permissible exposure limits.

Engineering Controls:

Ventilation:
Use adequate local exhaust ventilation to control airborne concentrations.

Personal Protective Equipment:

Respiratory Protection:
Use a NIOSH-approved respirator if ventilation is inadequate or exposure limits are exceeded.

Gloves:
Wear chemical-resistant gloves (e.g., nitrile or butyl rubber) to prevent skin contact.

Eye Protection:
Use safety goggles or face shields to protect eyes from splashes.

Clothing:
Wear protective clothing such as lab coats or aprons to minimize skin exposure.

Identifiers of Allyl Alcohol Alkoxylate:
IUPAC Name: Allyl alcohol
Chemical Formula: C₃H₅OH
Molecular Weight: 58.08 g/mol
CAS Registry Number: 107-18-6
SMILES Notation: OCC=C
InChI: InChI=1S/C3H6O/c1-2-3-4/h2-4H,1H2
InChIKey: GYNZJQPHCAHJLK-UHFFFAOYSA-N
EC Number: 203-429-5
PubChem CID: 6346
RTECS Number: AH6650000

Beilstein Number: 60596
NSC Number: 3146
ChemSpider ID: 6104
UN Number 1230
Chemical Abstracts Service (CAS) Name: 2-Propen-1-ol (a systematic name reflecting its structure)

Composition: Polyalkyleneglycolmonoallylether
CH2=CHCH2(OCH2CH2)n(CH2CHCH3)mOH

Properties of Allyl Alcohol Alkoxylate:
Density: 0.80 g/cm³ at 20°C
Boiling Point: 97°C (207°F)
Melting Point: -85°C (-121°F)
Flash Point: 22°C (72°F)
Vapor Pressure: 30 mmHg at 20°C

Molecular Formula: C₃H₅OH
Molecular Weight: 58.08 g/mol
Appearance: Colorless liquid
Odor: Pungent, characteristic smell
Boiling Point: Approximately 97°C (207°F)
Melting Point: -85°C (-121°F)
Density: 0.80 g/cm³ at 20°C
Solubility: Miscible with water, alcohols, and most organic solvents

Specifications of Allyl Alcohol Alkoxylate:
Purity: 100%
Form at 20°C: clear, liquid 
Color number: Hazen 0 - 100  
pH value 5% in H2O: 4.0 - 6.5  
Water content: 0.0 - 0.3 
Hydroxyl number: 40 - 50 mgKOH/g 
 

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