4,4'-Methylenebis(2-ethyl-6-methylaniline)
[CAS# 19900-72-2]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anilines
• Name: 4,4'-Methylenebis(2-ethyl-6-methylaniline)
• Molecular Formula: C₁₉H₂₆N₂
• Molecular Weight: 282.43
• CAS Registry Number: 19900-72-2
• EC Number: 672-703-6
• SMILES: CCC1=C(C(=CC(=C1)CC2=CC(=C(C(=C2)C)N)CC)C)N

Properties

• Solubility: 0.4163 mg/L (25 ºC water)
• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.599, Calc.^*
• Melting point: 178.25 ºC
• Boiling Point: 443.1±40.0 ºC (760 mmHg), Calc.^*, 437.00 ºC
• Flash Point: 266.0±26.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

4,4'-Methylenebis(2-ethyl-6-methylaniline), often abbreviated as MBEM, is an organic compound that belongs to the class of aromatic amines. Its structure features two 2-ethyl-6-methylaniline groups linked by a methylene bridge, which imparts unique properties that make it useful in various industrial applications. The discovery and development of MBEM can be traced back to the mid-20th century, coinciding with a growing demand for chemical intermediates in the production of polymers and dyes.

The synthesis of MBEM typically involves the reaction of 2-ethyl-6-methylaniline with formaldehyde or related compounds. This reaction highlights the compound's role as a versatile building block in organic synthesis. Researchers recognized that the methylene bridge in MBEM enhances its ability to act as a curing agent, particularly in the production of epoxy resins and polyurethane systems. These materials are highly valued for their strength, durability, and resistance to environmental degradation, making them suitable for a wide range of applications, from coatings and adhesives to construction materials.

One of the primary applications of 4,4'-methylenebis(2-ethyl-6-methylaniline) is in the field of polymer chemistry, where it serves as a hardener or curing agent in epoxy resin formulations. The presence of MBEM facilitates the cross-linking of epoxy resins, resulting in a material that exhibits improved mechanical properties and thermal stability. This is particularly important in applications requiring robust materials, such as in automotive and aerospace industries, where performance under extreme conditions is critical.

In addition to its role in epoxy resins, MBEM is utilized in the production of polyurethane elastomers. These materials are known for their flexibility and resilience, making them ideal for applications in coatings, sealants, and foams. The incorporation of MBEM into polyurethane formulations enhances the overall performance characteristics, including chemical resistance and mechanical strength.

Moreover, 4,4'-methylenebis(2-ethyl-6-methylaniline) has found applications in the dye industry, particularly in the synthesis of colorants and pigments. Its aromatic structure allows it to be integrated into various dye formulations, providing vibrant colors and stability. The versatility of MBEM in dye applications extends to textiles, plastics, and inks, where it contributes to the aesthetic appeal and durability of the final products.

Despite its utility, the use of MBEM and similar aromatic amines has raised health and environmental concerns. Studies have indicated that certain aromatic amines may be carcinogenic, prompting regulatory scrutiny regarding their handling and use. This has led to increased efforts in developing safer alternatives and implementing measures to minimize exposure in industrial settings.

Ongoing research into 4,4'-methylenebis(2-ethyl-6-methylaniline) seeks to enhance its applications while addressing safety concerns. Innovations in formulation chemistry aim to create products that maximize the benefits of MBEM while mitigating potential risks. This includes exploring safer substitutes and optimizing the use of existing compounds to ensure compliance with evolving safety regulations.

The discovery and application of 4,4'-methylenebis(2-ethyl-6-methylaniline) underscore its significance as a functional compound in various industrial sectors. Its roles in polymer synthesis and dye production illustrate the importance of chemical intermediates in advancing technology and material science, while ongoing research highlights the need for safe practices in chemical usage.