2-N-Morpholinoethyl methacrylate (MEMA) is a monofunctional methacrylate monomer containing a morpholine tertiary amine. Radical polymerization incorporates the morpholine group as a pendant, ionizable functionality in the resulting polymer.
CAS: 2997-88-8 | Purity: ≥95% | Molecular weight: 199.2 g/mol
Related names: 2-Morpholinoethyl methacrylate; MEMA; 2-(N-morpholinoethyl) methacrylate.
The morpholine nitrogen can be protonated under acidic conditions. In MEMA-containing polymers, this acid-base behavior provides pH-dependent charge and can alter aqueous solubility and solution behavior. Poly(2-N-morpholinoethyl methacrylate) (PMEMA) is water soluble at ambient temperature under acidic and neutral conditions, with its aqueous phase behavior also influenced by temperature, electrolyte concentration, molecular weight, and polymer architecture.
For the corresponding acrylate monomer, see 2-N-Morpholinoethyl acrylate, ≥95%.
Key Properties
- Monofunctional methacrylate monomer
- Morpholine tertiary-amine functionality
- CAS: 2997-88-8
- Molecular formula: C10H17NO3
- Molecular weight: 199.2 g/mol
- Purity: ≥95%
- Inhibitor: approximately 1200 ppm MEHQ
- Appearance: clear, colorless to slightly yellow liquid
- Physical state: liquid
- Package size: 100 g
- Storage: 4°C
Applications
Functional Polymer & Copolymer Synthesis
MEMA can be incorporated into methacrylate polymers and copolymers to introduce pendant morpholine tertiary-amine groups. Comonomer ratio and polymer architecture determine the concentration and distribution of ionizable functionality along the polymer chain.
pH-Responsive Polymer Research
Protonation of the morpholine tertiary amine increases as pH decreases. MEMA-containing polymers are therefore useful for studying relationships among ionization, polymer charge, aqueous solubility, and solution conformation.
Temperature- & Electrolyte-Dependent Solution Behavior
PMEMA exhibits aqueous phase behavior that depends on temperature and electrolyte concentration in addition to pH. These responses arise from the polymer and depend on variables including molecular weight, composition, architecture, and solution conditions.
Controlled Polymerization
MEMA can be polymerized by controlled methods including group-transfer polymerization and electrochemically triggered atom-transfer radical polymerization. Polymer molar mass, dispersity, and architecture depend on the polymerization method and reaction conditions.
Chemical Functionality & Selection
- Contains one polymerizable methacrylate group
- Contains a tertiary amine within the morpholine ring
- Protonation of the tertiary amine provides pH-dependent ionization
- Polymer solution behavior depends on pH, temperature, ionic strength, molecular weight, composition, and architecture
- MEMA and 2-N-morpholinoethyl acrylate are chemically distinct monomers
MEMA contains a methyl substituent on the polymerizable methacrylate group that is absent from the corresponding acrylate. For acrylate-based polymer synthesis, see 2-N-Morpholinoethyl acrylate, ≥95%.
Application Tips
- Account for the approximately 1200 ppm MEHQ inhibitor when establishing radical polymerization conditions
- Control initiator or catalyst concentration, temperature, reaction time, and oxygen exposure when comparing polymerizations
- Control pH and ionic strength when evaluating the aqueous behavior of MEMA-containing polymers
- Maintain consistent polymer molecular weight and comonomer composition when comparing solution or phase behavior
Handling & Storage
- Store at 4°C
- Keep the container tightly closed in a cool, well-ventilated location
- Keep away from heat, sparks, open flames, and other ignition sources
- Use with adequate laboratory ventilation or in a chemical fume hood
- Wear protective gloves and eye protection during handling
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FAQ
Click a question to expand.
1. What is 2-N-Morpholinoethyl methacrylate?
2-N-Morpholinoethyl methacrylate (MEMA) is a monofunctional methacrylate monomer containing a morpholine tertiary amine. Polymerization incorporates the morpholine functionality as a pendant group along the polymer chain.
2. What is the purity of MEMA?
The specified chemical purity is ≥95%.
3. What is MEMA used for?
MEMA is used in polymer and copolymer synthesis to introduce pendant morpholine tertiary-amine groups. This functionality is useful in polymer research involving pH-dependent ionization and aqueous solution behavior.
4. How does pH affect MEMA-containing polymers?
The morpholine tertiary amine becomes increasingly protonated as pH decreases. This changes polymer charge and can affect aqueous solubility, chain conformation, and intermolecular interactions.
5. Is PMEMA water soluble?
At ambient temperature, PMEMA is water soluble under acidic and neutral conditions. Solubility and phase behavior vary with pH, temperature, electrolyte concentration, molecular weight, and polymer architecture.
6. Is MEMA the same as 2-N-Morpholinoethyl acrylate?
No. MEMA is the methacrylate analogue and contains a methyl substituent on the polymerizable group that is absent from 2-N-morpholinoethyl acrylate. See 2-N-Morpholinoethyl acrylate, ≥95%.
7. Can MEMA be used in controlled polymerization?
Yes. MEMA can be polymerized using controlled methods including group-transfer polymerization and electrochemically triggered atom-transfer radical polymerization. Reaction conditions should be selected for the targeted molecular weight and polymer architecture.
8. Does MEMA contain an inhibitor?
Yes. The inhibitor concentration is approximately 1200 ppm MEHQ. Inhibitor content should be considered when establishing radical polymerization conditions.
9. How should MEMA be stored?
Store at 4°C with the container tightly closed in a cool, well-ventilated location.
10. What package size is available?
Available in a 100 g package. For larger quantities, use the bulk-quote option.
Safety & Documentation
2-N-Morpholinoethyl methacrylate is a flammable liquid and vapor and can cause serious eye irritation. Use appropriate laboratory ventilation, protective gloves, and eye protection during handling. Review the Safety Data Sheet (SDS) for complete handling and safety information, the Product Specification for current quality-control specifications, and the Monomers Product Guide for related functional monomers.
