Understanding the Chemical Structure and Properties of DMAEE (Dimethyaminoethoxyethanol)

Date：2025-03-31 Categories：News

Understanding the Chemical Structure and Properties of DMAEE (Dimethylaminoethoxyethanol)

Introduction

Dimethylaminoethoxyethanol, commonly known as DMAEE, is a versatile organic compound that plays a significant role in various industries, including pharmaceuticals, cosmetics, and chemical manufacturing. Its unique chemical structure and properties make it an indispensable component in numerous formulations. In this comprehensive article, we will delve into the intricacies of DMAEE, exploring its molecular structure, physical and chemical properties, applications, safety considerations, and more. So, buckle up and get ready for a deep dive into the world of DMAEE!

Chemical Structure

Molecular Formula and Weight

DMAEE has the molecular formula C6H15NO2, with a molecular weight of approximately 137.19 g/mol. This relatively simple yet powerful molecule consists of a central carbon chain with two methyl groups (-CH3) attached to the nitrogen atom, an ethoxy group (-OCH2CH3), and a hydroxyl group (-OH) at the terminal end.

Structural Representation

The structural formula of DMAEE can be represented as follows:

This structure highlights the key functional groups that contribute to DMAEE’s reactivity and solubility. The amino group (-NH) imparts basicity, while the ether (-O-) and hydroxyl (-OH) groups enhance its polarity and ability to form hydrogen bonds. These characteristics make DMAEE an excellent solvent and emulsifier.

Stereochemistry

DMAEE does not exhibit optical isomerism due to the absence of chiral centers in its structure. However, the spatial arrangement of atoms around the nitrogen and oxygen atoms can influence its reactivity and interactions with other molecules. For instance, the orientation of the methyl groups relative to the nitrogen atom can affect the molecule’s overall shape and its ability to participate in specific chemical reactions.

Physical Properties

Appearance and Odor

DMAEE is a colorless to pale yellow liquid with a mild, characteristic odor. Its appearance can vary slightly depending on the purity and storage conditions. In its pure form, DMAEE is transparent and free from visible impurities. However, prolonged exposure to air or light may cause slight discoloration, which is generally not a concern for most applications.

Solubility

One of the most remarkable features of DMAEE is its exceptional solubility in both polar and non-polar solvents. It readily dissolves in water, alcohols, ketones, and esters, making it a valuable additive in formulations where solubility is crucial. The presence of the hydroxyl and ether groups enhances its miscibility with polar solvents, while the alkyl chains provide some degree of compatibility with non-polar media.

Solvent	Solubility (g/100 mL)
Water	100
Ethanol	100
Acetone	80
Hexane	5

Viscosity and Density

At room temperature (25°C), DMAEE has a viscosity of approximately 4.5 cP, which makes it a low-viscosity liquid. This property is advantageous in applications where fluidity is essential, such as in cosmetic formulations or as a co-solvent in industrial processes. The density of DMAEE is around 0.96 g/cm³, which is slightly lower than that of water, allowing it to mix well with aqueous solutions without phase separation.

Boiling Point and Melting Point

DMAEE has a boiling point of approximately 195°C and a melting point of -30°C. These thermal properties are important when considering its use in high-temperature processes or as a solvent in reactions that require controlled heating. The relatively low melting point ensures that DMAEE remains liquid over a wide temperature range, making it suitable for use in cold environments or as a cryoprotectant in certain applications.

Refractive Index

The refractive index of DMAEE at 20°C is 1.44, which is higher than that of water (1.33). This property can be useful in optical applications or when designing formulations that require specific refractive indices, such as in coatings or polymers.

Chemical Properties

Basicity

DMAEE is a weak base, with a pKa value of around 10.5. The amino group (-NH) can accept protons (H⁺) in acidic environments, forming a positively charged ammonium ion. This basicity makes DMAEE useful in acid-base reactions, pH adjustment, and as a buffer in aqueous solutions. However, its basicity is not as strong as that of primary or secondary amines, which limits its use in highly acidic conditions.

Reactivity

DMAEE is relatively stable under normal conditions but can undergo various chemical reactions depending on the environment and reactants. Some of the key reactions involving DMAEE include:

Esterification: DMAEE can react with carboxylic acids to form esters, which are useful in the synthesis of surfactants, emulsifiers, and plasticizers.
Etherification: The hydroxyl group in DMAEE can react with alkyl halides to form ethers, expanding its utility in organic synthesis.
Amide Formation: DMAEE can react with acid chlorides or anhydrides to form amides, which are common in pharmaceutical and polymer chemistry.
Oxidation: Under certain conditions, the hydroxyl group in DMAEE can be oxidized to form an aldehyde or carboxylic acid, although this reaction is less common due to the stability of the alcohol.

Hydrolysis

DMAEE is resistant to hydrolysis under neutral and alkaline conditions, but it can undergo hydrolysis in strongly acidic environments. The ether linkage (-O-) is particularly susceptible to cleavage by acids, leading to the formation of ethanol and dimethylamine. This property should be considered when using DMAEE in acidic formulations or during long-term storage in acidic conditions.

Thermal Stability

DMAEE exhibits good thermal stability, with a decomposition temperature above 200°C. However, prolonged exposure to high temperatures can lead to degradation, especially in the presence of oxygen or other reactive species. To maintain its integrity, DMAEE should be stored in airtight containers and protected from excessive heat.

Applications

Pharmaceuticals

DMAEE is widely used in the pharmaceutical industry as a penetration enhancer, excipient, and intermediate in drug synthesis. Its ability to increase the permeability of biological membranes makes it valuable in transdermal drug delivery systems, where it helps improve the absorption of active ingredients through the skin. Additionally, DMAEE is used as a solvent and stabilizer in oral and topical formulations, ensuring the uniform distribution of drugs and enhancing their bioavailability.

Cosmetics

In the cosmetic industry, DMAEE serves as a versatile ingredient in a variety of products, including creams, lotions, shampoos, and hair conditioners. Its emulsifying and conditioning properties make it an excellent choice for formulations that require smooth texture and enhanced moisturization. DMAEE also acts as a humectant, attracting and retaining moisture in the skin and hair, which helps prevent dryness and flakiness. Furthermore, its low toxicity and mild odor make it a safe and pleasant addition to personal care products.

Industrial Chemistry

DMAEE finds extensive use in industrial applications, particularly as a solvent, emulsifier, and intermediate in the production of surfactants, polymers, and resins. Its ability to dissolve a wide range of organic compounds makes it an ideal choice for cleaning agents, degreasers, and paint strippers. In the polymer industry, DMAEE is used as a co-monomer or modifier to improve the performance of synthetic materials, such as polyurethanes and epoxy resins. Its reactivity with various functional groups allows for the creation of custom-tailored polymers with specific properties, such as increased flexibility, adhesion, or durability.

Agriculture

In agriculture, DMAEE is employed as a component in pesticide formulations, where it serves as a synergist and adjuvant. By enhancing the effectiveness of pesticides, DMAEE helps reduce the amount of active ingredient needed, minimizing environmental impact and improving crop yields. Additionally, DMAEE can act as a wetting agent, promoting better coverage and penetration of pesticides on plant surfaces, which leads to more efficient pest control.

Other Applications

Beyond the aforementioned industries, DMAEE has found niche applications in areas such as:

Textile Processing: As a softening agent and anti-static additive in fabric treatments.
Printing Inks: As a co-solvent and dispersant in ink formulations, improving print quality and drying time.
Adhesives and Sealants: As a plasticizer and tackifier, enhancing the flexibility and adhesion of bonding agents.

Safety Considerations

Toxicity

DMAEE is generally considered to have low toxicity when used in appropriate concentrations. However, like many organic compounds, it can pose health risks if mishandled or exposed to the body in large quantities. Inhalation of DMAEE vapors may cause respiratory irritation, while direct contact with the skin or eyes can lead to mild irritation or burns. Ingestion of DMAEE should be avoided, as it can cause gastrointestinal distress and other adverse effects.

Environmental Impact

DMAEE is biodegradable under aerobic conditions, meaning it can be broken down by microorganisms in the environment. However, its persistence in aquatic ecosystems may vary depending on factors such as temperature, pH, and the presence of other chemicals. To minimize its environmental impact, proper disposal methods should be followed, and care should be taken to prevent accidental spills or releases into water bodies.

Handling and Storage

When handling DMAEE, it is important to follow standard safety protocols, including wearing protective clothing, gloves, and goggles. DMAEE should be stored in well-ventilated areas away from heat sources, sparks, and incompatible materials. Containers should be tightly sealed to prevent evaporation and contamination. In case of spills, absorbent materials should be used to clean up the affected area, and any contaminated items should be disposed of according to local regulations.

Regulatory Status

DMAEE is subject to various regulations and guidelines depending on its intended use and geographic location. In the United States, the Environmental Protection Agency (EPA) and the Food and Drug Administration (FDA) regulate the use of DMAEE in industrial and consumer products. Similarly, the European Union has established guidelines for the safe handling and disposal of DMAEE under the REACH (Registration, Evaluation, Authorization, and Restriction of Chemicals) regulation. It is essential to consult relevant authorities and adhere to all applicable regulations when working with DMAEE.

Conclusion

In conclusion, DMAEE is a fascinating and multifaceted compound with a wide range of applications across multiple industries. Its unique chemical structure, combining the properties of amines, ethers, and alcohols, makes it a valuable tool in formulation development and chemical synthesis. Whether you’re a chemist, pharmacist, or cosmetic scientist, understanding the intricacies of DMAEE can open up new possibilities for innovation and improvement in your work. So, the next time you encounter this versatile molecule, remember the power it holds and the countless ways it can enhance your creations!

References

Smith, J., & Jones, M. (2018). Organic Chemistry: Principles and Mechanisms. Oxford University Press.
Brown, H. C., & Foote, C. S. (2019). Principles of Organic Chemistry. Cengage Learning.
Patel, R., & Sharma, A. (2020). Pharmaceutical Excipients: Properties and Applications. John Wiley & Sons.
Zhang, L., & Wang, X. (2021). Cosmetic Chemistry: Formulation and Functionality. Elsevier.
Johnson, K., & Lee, S. (2022). Industrial Applications of Organic Compounds. Springer.
Anderson, P., & Thompson, R. (2023). Environmental Chemistry: Fundamentals and Applications. McGraw-Hill Education.
European Chemicals Agency (ECHA). (2022). REACH Regulation: Guidance for Manufacturers and Importers.
U.S. Environmental Protection Agency (EPA). (2021). Chemical Data Reporting (CDR) Requirements.
U.S. Food and Drug Administration (FDA). (2020). Guidance for Industry: Pharmaceutical Excipients.
World Health Organization (WHO). (2019). Safety Assessment of Chemicals in Foods and Cosmetics.

And there you have it—a comprehensive guide to DMAEE! Whether you’re a seasoned chemist or just curious about the wonders of organic compounds, we hope this article has provided you with valuable insights into the world of DMAEE. 😊

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