4-Acryloylmorpholine
[CAS# 5117-12-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate
• Name: 4-Acryloylmorpholine
• Synonyms: 1-morpholin-4-ylprop-2-en-1-one
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.17
• CAS Registry Number: 5117-12-4
• EC Number: 418-140-1
• SMILES: C=CC(=O)N1CCOCC1

Properties

• Density: 1.122
• Melting point: -35 °C
• Refractive index: 1.512
• Boiling point: 158 °C (50mmHg)
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS08;GHS05;GHS07 Danger
• Risk Statements: H302-H373-H318-H317
• Safety Statements: P260-P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P354+P338-P317-P319-P321-P330-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H312

• Transport Information: UN 1760

Discovery and Applications

4-Acryloylmorpholine, an organic compound featuring both acrylate and morpholine functionalities, represents a significant advancement in the field of polymer chemistry. This substance is known for its unique chemical structure, which incorporates an acryloyl group attached to a morpholine ring. This combination imparts specific properties that are valuable in various industrial applications.

The discovery of 4-acryloylmorpholine emerged from the ongoing search for new monomers with enhanced reactivity and versatility for polymerization processes. The synthesis of this compound involves the introduction of an acryloyl group into the morpholine ring structure. The resulting product is characterized by its ability to participate in polymerization reactions, forming polymers with desirable properties.

One of the primary applications of 4-acryloylmorpholine is in the development of advanced polymers and copolymers. The compound is used as a monomer in the polymerization process to create materials with specific characteristics. The acrylate group facilitates polymerization through free radical mechanisms, while the morpholine ring contributes to the resulting polymer's flexibility and stability. Polymers derived from 4-acryloylmorpholine are utilized in a range of applications, including coatings, adhesives, and specialty materials. These polymers often exhibit enhanced mechanical properties, chemical resistance, and durability, making them suitable for demanding environments.

In addition to its use in polymer chemistry, 4-acryloylmorpholine plays a role in the development of functional materials. Its ability to undergo polymerization and form cross-linked networks allows it to be incorporated into materials with specific functional properties. For instance, it can be used to create hydrogels and other types of smart materials that respond to environmental stimuli, such as changes in pH or temperature. These materials have applications in fields such as drug delivery, tissue engineering, and environmental sensing.

Another notable application of 4-acryloylmorpholine is in the formulation of coatings and adhesives. The compound's reactivity and ability to form strong bonds make it a valuable component in these products. When used in coatings, 4-acryloylmorpholine contributes to the development of films with excellent adhesion, hardness, and resistance to abrasion. In adhesives, it enhances the bonding strength and durability of the adhesive formulations, making them suitable for use in various industrial and consumer applications.

The compound also finds application in the field of textiles, where it is used to modify the properties of fibers and fabrics. By incorporating 4-acryloylmorpholine into textile treatments, manufacturers can improve the performance characteristics of fabrics, such as their resistance to wrinkling, staining, and moisture. This results in textiles with enhanced durability and functionality, meeting the demands of both consumer and industrial applications.

Overall, 4-acryloylmorpholine is a versatile chemical substance with significant potential in the development of advanced materials. Its unique chemical properties and ability to participate in polymerization reactions make it a valuable component in the creation of high-performance polymers, functional materials, and specialty coatings and adhesives.

References

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DOI: 10.1186/s40580-024-00452-3

2024. Green Synthesis and Characterization of UV-Curable Multifunctional Rosin-Based Resins via Michael Addition Reaction. Journal of Polymers and the Environment.
DOI: 10.1007/s10924-024-03253-1

2023. Study on the preparation of long-term stability core-shell particles/epoxy acrylate emulsion and toughening improvement for 3D printable UV-curable resin. Journal of Polymer Research.
DOI: 10.1007/s10965-023-03489-w