N,N'-Methylenebisacrylamide
[CAS# 110-26-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N,N'-Methylenebisacrylamide
• Synonyms: Bis-acrylamide; N,N-Methylene-bis-acrylamide; N,N'-Methylenebis(2-propenamide); MBA; NAPP
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.17
• CAS Registry Number: 110-26-9
• EC Number: 203-750-9
• SMILES: C=CC(=O)NCNC(=O)C=C

Properties

• Water solubility: 0.01-0.1 g/100 mL at 18 ºC
• Density: 1.1±0.1 g/cm³, Calc.^*, 1.235
• Melting point: 185 ºC
• Index of Refraction: 1.475, Calc.^*
• Boiling Point: 445.1±41.0 ºC (760 mmHg), Calc.^*
• Flash Point: 215.0±27.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Hazard Statements: H301-H302-H312-H317-H318-H332-H340-H350-H351-H360-H361-H372
• Precautionary Statements: P203-P260-P261-P264-P264+P265-P270-P271-P272-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P318-P319-P321-P330-P333+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Germ cell mutagenicity	Muta.	1B	H340
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Carcinogenicity	Carc.	1B	H350
Reproductive toxicity	Repr.	2	H361
Carcinogenicity	Carc.	2	H351
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	2	H361fd
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Germ cell mutagenicity	Muta.	2	H341

• Transport Information: UN 2811

Discovory and Applicatios

N,N'-Methylenebisacrylamide (MBAA) is an organic compound that serves as a widely used cross-linking agent, primarily in polymer chemistry. Its discovery dates back to the development of acrylamide-based materials in the mid-20th century. MBAA is a derivative of acrylamide, consisting of two acrylamide groups connected by a methylene bridge. Its chemical structure gives it the ability to form cross-links between polymer chains, which is essential for creating three-dimensional polymer networks with enhanced mechanical properties.

The chemical structure of MBAA is represented by the formula C₇H₁₀N₂O₂, and it is a white crystalline solid at room temperature. Its ability to dissolve in water and organic solvents like ethanol makes it convenient for use in a wide range of chemical reactions. The versatility and effectiveness of MBAA as a cross-linking agent have made it an important component in the production of hydrogels, gels, and other polymeric materials.

MBAA is most notably used in the synthesis of polyacrylamide gels, a critical tool in biochemical and molecular biology applications. The cross-linking of polyacrylamide chains by MBAA produces a stable gel matrix that is used in gel electrophoresis for the separation of proteins, DNA, and RNA. This technique has become indispensable in the field of molecular biology, where it is used for analyzing genetic material and proteins in research and diagnostic settings. The polyacrylamide gel acts as a molecular sieve, allowing researchers to separate biomolecules based on their size and charge. MBAA's role as a cross-linker ensures that the gel remains stable during the electrophoresis process.

Another important application of MBAA is in the preparation of hydrogels, which are networks of polymer chains that can retain large amounts of water. Hydrogels cross-linked with MBAA are used in a variety of biomedical and environmental applications, including drug delivery systems, wound dressings, and water purification. The cross-linking properties of MBAA allow the hydrogel to maintain its structure and swell in response to changes in the surrounding environment. In drug delivery, MBAA-cross-linked hydrogels are engineered to release therapeutic agents in a controlled manner, offering a promising approach to sustained drug delivery.

In environmental science, MBAA-based hydrogels are used in water treatment and soil conditioning. Hydrogels can absorb and retain large amounts of water, making them useful for capturing pollutants or enhancing soil moisture retention in agricultural applications. The water-absorbing capabilities of these hydrogels help in the remediation of contaminated water sources, where they can trap heavy metals or other hazardous substances. Additionally, the use of MBAA-cross-linked hydrogels in agriculture has been explored for improving water efficiency in arid regions by reducing the frequency of irrigation.

MBAA is also employed in the production of superabsorbent polymers (SAPs), which are capable of absorbing many times their weight in water. SAPs cross-linked with MBAA are used in products such as diapers, sanitary products, and industrial absorbents. The cross-linking effect introduced by MBAA ensures that the polymer does not dissolve in water but instead forms a gel-like structure that can hold large volumes of liquid. This application highlights the value of MBAA in industries that require high-capacity water absorption materials.

Beyond its role as a cross-linking agent, MBAA has been utilized in the synthesis of specialty polymers used in coatings, adhesives, and sealants. The presence of the methylene bridge in MBAA contributes to the rigidity of the polymer network, enhancing the durability and chemical resistance of the resulting materials. MBAA-cross-linked polymers are particularly valued in applications where stability under harsh environmental conditions is required, such as in protective coatings for metals and in adhesives exposed to water and chemicals.

Handling MBAA requires careful safety precautions, as it is a toxic and potentially harmful substance if ingested or inhaled. Exposure to MBAA can cause skin and eye irritation, and prolonged exposure may lead to more serious health effects. In laboratory settings, appropriate personal protective equipment, such as gloves and goggles, is necessary when working with this compound. Additionally, MBAA should be stored in a well-ventilated area away from direct heat or flame to minimize risks associated with its use.

Despite its wide utility, environmental and health concerns surrounding MBAA have prompted efforts to develop alternative cross-linking agents or greener synthetic methods for its production. These initiatives focus on reducing the environmental impact of its synthesis and use, while still maintaining the efficiency of cross-linking required in polymer production.