2-Carboxyethyl acrylate

• CAS: 24615-84-7
• Catalog Number: ACM-MO-24615847
• Category: Main Products; Acrylate Monomers
• Molecular Weight: 144.13 g/mol
• Molecular Formula: C6H8O4
• Synonyms: 3-prop-2-enoyloxypropanoic acid
• SMILES: OC(=O)CCOC(=O)C=C
• InChI: 1S/C6H8O4/c1-2-6(9)10-4-3-5(7)8/h2H,1,3-4H2,(H,7,8)
• InChI Key: CYUZOYPRAQASLN-UHFFFAOYSA-N
• Boiling Point: 103 °C/19 mmHg
• Density: 1.214 g/mL at 25 °C (lit.)
• Appearance: Colorless Liquid
• Application: Can be polymerized in solution or emulsion to produce acrylic, vinyl-acrylic, or styrenic-acrylic polymers with greater flexibility due to lower glass transition of itshomopolymer (<30C) and improved adhesion.
• Storage: Store at 4 degrees celsius
• Contains: 900-1100 ppm MEHQ as inhibitor
• Features And Benefits: More reactive in its salt form than acylic acid, allowing high levels of incorporation over awide pH range. Also see Poly(2-carboxyethyl) acrylate, 407585.
• MDL Number: MFCD00040709
• NACRES: NA.23
• Packaging: Packaging; 50, 500 mL in glass bottle
• PubChem ID: 24879262
• Quality Level: 200
• Refractive Index: n20/D 1.457
• Specific Gravity: 1.16
• Storage Temperature: 2-8°C

Case Study

2-Carboxyethyl acrylate mitigates the negative effects of oxygen inhibition in gel casting

Pietrzak, Emilia, Paulina Wiecinska, and Mikolaj Szafran. Ceramics International 42.12 (2016): 13682-13688.

The application of 2-carboxyethyl acrylate as a novel monomer in alumina gel casting. Oxygen inhibition, which hinders polymerization, is a known negative phenomenon in gel casting, but this has not been fully overcome for samples formed in air. 2-Hydroxyethyl acrylate was used as a reference monomer in this study. The rheological behavior of alumina suspensions containing both monomers was investigated, and the properties of the green and sintered bodies obtained by gel casting were also measured. Differences in rheological properties and ceramic-monomer interactions within the slurry were analyzed. The successful gel casting process using alumina powder demonstrated high density and mechanical strength, as well as images of the microstructure of the sintered ceramic parts.
The first step involved loading the ceramic slurry into an alumina container. The dispersant was initially dissolved in deionized water. Then, appropriate amounts of ceramic powder and a polymerization activator were added, and after prior homogenization, the monomers were precipitated into the slurry. Preliminary studies indicate that dissolving 2-carboxyethyl acrylate in a solvent before adding the alumina powder negatively impacts the rheological properties of the ceramic slurry. 2-Carboxyethyl acrylate was added to a mixture of solvent, dispersant, and alumina powder, initially dispersing the ceramic particles appropriately, and then uniformly distributing the monomers in the slurry. The composition of the ceramic hanger was initially determined through a series of experiments. All operations were performed at room temperature. After mixing, the slurry was deoxidized using a centrifugal mixer and deaerator to remove bubbles that could lead to the formation of large pores in the ceramic components before and after sintering. In the second step, a polymerization initiator was added to the ceramic slurry. After stirring the slurry with the initiator, the slurry was cast into a PVC mold and gelled at room temperature.

A study on the modification of cellulose nanocrystals with 2-carboxyethyl acrylate to enhance their adhesive properties

Ali, Amjad, et al. Frontiers in Bioengineering and Biotechnology 9 (2022): 797672.

Cellulose nanocrystals (CNCs) offer unparalleled advantages in the preparation of nanocomposites for a wide range of applications. However, a major challenge in the preparation of CNCs for nanocomposites is their insufficient compatibility with hydrophobic polymers. CNCs were synthesized from cotton and then modified with 2-carboxyethyl acrylate to improve their corresponding mechanical, adhesive, contact angle, and thermal properties. Compared to standard samples, the modified CNCs exhibited high shear stress, high toughness, efficient degradation, thermal stability, and recyclability, thanks to the combined effect of the highly branched topology of epoxy resins and good compatibility. The results indicate that 2-carboxyethyl acrylate enhances their properties in the presence of epoxy resins, which will further expand their applications in various fields.
The CNCs were dispersed in 40 mL of laboratory brewed distilled water at 60°C and stirred for 30 min under nitrogen at room temperature. Then, 66.6 mg of potassium persulfate was dissolved in 20 mL of distilled water and injected into the solution using a syringe. Thirty minutes later, 2.1 mL of 2-carboxyethyl acrylate monomer was also injected, and the reaction was stirred at 60°C for 3 hours. After the product cooled to room temperature, it was washed three times with a mixture of 30 mL methanol and 70 mL, and then centrifuged at 5000 rpm for 10 minutes. The mixture was washed again with acetone to remove ungrafted polymer. This process was repeated three times. The product was then placed in a vacuum oven at 40°C and baked for 24 hours until completely dry. Afterward, the sample was placed in a bottle, named Modified Cellulose Nanocrystals (MCNCs), and stored in a desiccator for further study and characterization.

In-situ hydrogels synthesized and characterized by grafting 2-carboxyethyl acrylate

Kim, Mi-Sook, et al. Journal of Biomedical Materials Research Part A: An Official Journal of The Society for Biomaterials 83.3 (2007): 674-682.

An in-situ hand-picked poly(ethylene dioxide) (PEO) hydrogel was developed and characterized through two steps: First, primary amine functional groups were grafted onto 2-carboxyethyl acrylate molecules, followed by a Michael-type addition reaction between the acrylate end groups and thiol end groups grafted onto PEO. The grafting of acrylate molecules onto the amine groups in deacetylated water-soluble chitosan was confirmed by observing the new acrylate peaks in the propylene-coated chitosan sample via Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy, as well as the relative viscosity changes of the shell and propylene-coated chitosan. After gelation and hydration, the formation process of the chitosan-PEO hydrogel was observed using digital imaging. Rheological analysis was performed on the hydrogel formation to detect changes in gelation time and phase angle, as well as the viscoelastic promoting force on frequency and strain percentage.
2-Carboxyethyl acrylate was grafted onto chitosan. 1.0 g of chitosan was dissolved in 80 mL of distilled water. 1.5 mL of 2-carboxyethyl acrylate was added to the solution. Grafting was performed at pH 4.75 by adding 2.3 mL of EDC to the mixture of chitosan and 2-carboxyethyl acrylate and incubating for 3 hours, resulting in a final concentration of 1:4:4 (chitosan:EDC:2-carboxyethyl acrylate), molar ratio. The product was an propylene-based thiazolinone, which precipitated in an organic solvent and then lyophilized overnight.

A research of microgels and duplex microgels containing 2-carboxyethyl acrylate

Zaki, Syazwani Mohd, and Sharan Musa. Proceeding of 5th International Conference on Advances in Manufacturing and Materials Engineering: ICAMME 2022, 9-10 August, Kuala Lumpur, Malaysia. Singapore: Springer Nature Singapore, 2023.

A novel pH-responsive microgel (MG) containing 2-carboxyethyl acrylate (CEA) as a copolymer. The MGs, synthesized via emulsion polymerization, are designated CEAX, where X exhibits varying CEA contents within the MG. These MG samples are labeled CEA14, CEA21, and CEA28. CEA MGs were used to prepare three DX MG gels, labeled DX CEA21, DX CEA28, and a hybrid system containing CEA21 and CEA28, by vinyl-functionalizing GMA. The particle size of the MGs increased significantly with increasing CEA content. The modulus (E) of the hybrid system was very close to that of the DX CEA28 gel, indicating that CEA28 distributed more stress in these hybrid gels. The DX CEA gel exhibited superior ductility compared to the established DX MAA gel.
First, SDS (1.214 g) was dissolved in deionized water (240 g) and added to a glass reaction vessel. APS (0.60 mmol) was dissolved in deionized water and added to the vessel before the monomer feed began. A monomer feed containing MMA (0.419 mol), 2-carboxyethyl acrylate, and EGDMA (5.35 mmol) was prepared by mechanical stirring and fed into the reaction vessel at a constant rate of 0.317 mL/min. The mass of CEA used to prepare CEA14, CEA21, and CEA28 were 0.069 mol, 0.113 mol, and 0.165 mol, respectively. After the copolymer solution was fed, the reaction continued for 1 hour. Finally, the products underwent extensive dialysis and water purification over 4 days. The obtained MGs were designated as CEA14 (14 mol%), CEA21 (21 mol%), and CEA28 (28 mol%), respectively. This study included data from MG in related studies using methacrylic acid (MAA) as a substitute for CEA for comparison. This MG contained MMA, MAA, and EGDMA, with a MAA concentration of 38 mol%.

Custom Q&A

What is the molecular formula of Beta-carboxyethyl acrylate?

The molecular formula of Beta-carboxyethyl acrylate is C6H8O4.

What is the molecular weight of Beta-carboxyethyl acrylate?

The molecular weight of Beta-carboxyethyl acrylate is 144.12 g/mol.

What is the IUPAC name of Beta-carboxyethyl acrylate?

The IUPAC name of Beta-carboxyethyl acrylate is 3-prop-2-enoyloxypropanoic acid.

What is the InChI of Beta-carboxyethyl acrylate?

The InChI of Beta-carboxyethyl acrylate is InChI=1S/C6H8O4/c1-2-6(9)10-4-3-5(7)8/h2H,1,3-4H2,(H,7,8).

What is the InChIKey of Beta-carboxyethyl acrylate?

The InChIKey of Beta-carboxyethyl acrylate is CYUZOYPRAQASLN-UHFFFAOYSA-N.

What is the canonical SMILES of Beta-carboxyethyl acrylate?

The canonical SMILES of Beta-carboxyethyl acrylate is C=CC(=O)OCCC(=O)O.

What is the CAS number of Beta-carboxyethyl acrylate?

The CAS number of Beta-carboxyethyl acrylate is 24615-84-7.

What is the XLogP3-AA value of Beta-carboxyethyl acrylate?

The XLogP3-AA value of Beta-carboxyethyl acrylate is 0.2.

How many hydrogen bond donor counts are there in Beta-carboxyethyl acrylate?

There is 1 hydrogen bond donor count in Beta-carboxyethyl acrylate.

What is the topological polar surface area of Beta-carboxyethyl acrylate?

The topological polar surface area of Beta-carboxyethyl acrylate is 63.6Ų.