2-N-Morpholinoethyl acrylate is a monofunctional acrylate monomer containing a morpholine tertiary amine. The acrylate group undergoes radical polymerization, introducing pendant morpholine functionality into the resulting polymer.
CAS: 19727-38-9 | Purity: ≥95% | Molecular weight: 185.22 g/mol
Related names: 2-Morpholinoethyl acrylate; acrylic acid, 2-morpholinoethyl ester.
The morpholine nitrogen is a tertiary amine whose protonation state depends on solution conditions. Incorporation of this functionality into a polymer provides an ionizable side group that can influence charge and aqueous behavior as pH and ionic strength change.
For the corresponding methacrylate monomer, see 2-N-Morpholinoethyl methacrylate, ≥95%.
Key Properties
- Monofunctional acrylate monomer
- Morpholine tertiary-amine functionality
- CAS: 19727-38-9
- Molecular formula: C9H15NO3
- Molecular weight: 185.22 g/mol
- Purity by GC: ≥95%
- Inhibitor (MEHQ): 500–1000 ppm
- Appearance: clear, colorless to yellow liquid
- Physical state: liquid
- Storage: room temperature
Applications
Functional Polymer & Copolymer Synthesis
2-N-Morpholinoethyl acrylate can be incorporated into polymers and copolymers by radical polymerization to introduce pendant morpholine tertiary-amine groups. The concentration of ionizable functionality in the polymer is determined by monomer composition and polymer architecture.
Ionizable Polymer Research
Polymers containing 2-N-morpholinoethyl acrylate can exhibit pH-dependent charge behavior because the morpholine tertiary amine can be protonated under acidic conditions. Solution behavior depends on polymer molecular weight, composition, architecture, pH, and ionic strength.
Controlled Radical Polymerization
2-N-Morpholinoethyl acrylate has been polymerized using controlled radical methods, including nitroxide-mediated polymerization and Cu(0)-mediated radical polymerization. Published studies report control over polymer molecular weight and dispersity under appropriate reaction conditions.
Chemical Functionality & Selection
- Contains one polymerizable acrylate group
- Contains a tertiary amine within the morpholine ring
- The tertiary amine provides ionizable functionality
- Polymer properties depend on comonomer composition, molecular weight, architecture, and degree of protonation
- The acrylate and methacrylate analogues are chemically distinct monomers
For polymer systems requiring the methacrylate analogue, see 2-N-Morpholinoethyl methacrylate, ≥95%.
Application Tips
- Account for the specified 500–1000 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 solution behavior of morpholine-functional polymers
- Keep comonomer composition and targeted molecular weight consistent when comparing polymer formulations
Handling & Storage
- Store at room temperature in a cool, well-ventilated location
- Use with adequate laboratory ventilation or in a chemical fume hood
- Wear protective gloves and eye protection during handling
- Avoid breathing vapors, mist, or spray
- Avoid contact with skin and eyes
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FAQ
Click a question to expand.
1. What is 2-N-Morpholinoethyl acrylate?
2-N-Morpholinoethyl acrylate is a monofunctional acrylate monomer containing a morpholine tertiary amine. Radical polymerization incorporates the morpholine functionality as a pendant group along the polymer chain.
2. What is the purity of 2-N-Morpholinoethyl acrylate?
The specified purity by gas chromatography is ≥95%.
3. What is 2-N-Morpholinoethyl acrylate used for?
It is used in functional polymer and copolymer synthesis where pendant morpholine tertiary-amine groups are required. The monomer has also been used in published controlled radical polymerization studies.
4. How does the morpholine group affect polymer behavior?
The morpholine nitrogen is a tertiary amine that can be protonated under acidic conditions. In polymers containing this functionality, changes in protonation can alter charge state and aqueous solution behavior.
5. Is poly(2-N-morpholinoethyl acrylate) water soluble?
Published homopolymerization studies have reported poly(2-N-morpholinoethyl acrylate) as water soluble. Solution behavior can vary with molecular weight, polymer architecture, pH, ionic strength, and comonomer composition.
6. Is 2-N-Morpholinoethyl acrylate the same as 2-N-Morpholinoethyl methacrylate?
No. They are distinct monomers. The methacrylate analogue contains an additional methyl substituent on the polymerizable carbon-carbon double bond. See 2-N-Morpholinoethyl methacrylate, ≥95%.
7. Does 2-N-Morpholinoethyl acrylate contain an inhibitor?
Yes. MEHQ is specified at 500–1000 ppm. Inhibitor content should be considered when establishing polymerization conditions.
8. How should 2-N-Morpholinoethyl acrylate be stored?
Store at room temperature in a cool, well-ventilated location.
9. Can I request a larger quantity?
Yes. For larger quantities, use the bulk-quote option.
Safety & Documentation
2-N-Morpholinoethyl acrylate is harmful if inhaled, causes skin and eye irritation, and may cause an allergic skin reaction. Use adequate 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 monomers.
