2-Carboxyethyl acrylate Chemical Properties

Boiling point:

103 °C/19 mmHg (lit.)

Density 

1.214 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.457(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

H₂O: soluble

pka

3.95±0.10(Predicted)

PH

2.95 (10wt. % in H2O)

Merck 

13,132

InChI

InChI=1S/C6H8O4/c1-2-6(9)10-4-3-5(7)8/h2H,1,3-4H2,(H,7,8)

InChIKey

CYUZOYPRAQASLN-UHFFFAOYSA-N

SMILES

C(OCCC(O)=O)(=O)C=C

LogP

0.600 (est)

EPA Substance Registry System

Hydracrylic acid acrylate (24615-84-7)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

23-26-36/37/39-45-36

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

RTECS 

UD3325250

HS Code 

29161290

MSDS

• Language:English Provider:SigmaAldrich

2-Carboxyethyl acrylate Usage And Synthesis

Description

2-Carboxyethyl acrylate is a highly versatile monomer extensively used to produce diverse polymers. It can be polymerized in solution or emulsion, producing vinyl-acrylic, acrylic, or styrenic-acrylic polymers with greater flexibility due to lower glass transition of itshomopolymer (<30C) and improved adhesion. It finds applications in various polymer production processes, including those geared towards optical applications like optical fibers, optical waveguides, and optical lenses. Moreover, 2-Carboxyethyl acrylate is instrumental in synthesizing polymers used in energy storage applications, such as fuel cells, batteries, and supercapacitors. 2-carboxyethyl acrylate could be used as a new monomer in the gel casting of alumina. This low-toxic, water-soluble monomer modifies the ceramic suspensions' rheological properties and minimizes the oxygen inhibition's negative effect [1-3].

Chemical Properties

Colorless to light yellow viscid liquid

Uses

2-Carboxyethyl Acrylate is used in the preparation of DNase enzyme derivatives that act as potent preventative material of bacterial adhesion and biofilm formation in biomaterials.

Application

2-Carboxyethyl acrylate can be polymerized in solution or emulsion to produce acrylic, vinyl acrylic, or styrene acrylic polymers, which are distinguished by their low glass transition temperatures (<30°C) as homopolymers. Greater elasticity, as well as improved adhesion.

Preparation

Synthesis of 1-ethoxyethyl acrylate (EEA) and protected 2-carboxyethyl acrylate (proCEA)
EEA and proCEA were synthesized following a previously published procedure and distilled prior to use. For the synthesis of proCEA (Figure 1), phosphoric acid (109 mg, 1.11 mmol) was weighed into a dry round bottom flask in a glovebox and then taken outside the glovebox, taking care that the phosphoric acid stayed dry. 2-Carboxyethyl acrylate (80 g, 555 mmol) and ethyl vinyl ether (48 g, 666 mmol) were added and the reaction was stirred for two days at room temperature. Hydrotalcite (Mg6Al2(OH)16CO3·4H2O, ~1 g) was added, stirred for one hour and filtered off. Excess ethyl vinyl ether was removed under reduced pressure and the product was distilled under reduced pressure (80 °C, 1.3 mbar).

Figure 1 Synthesis of proCEA

Hazard

A severe skin irritant.

References

[1] Emilia Pietrzak, Mikolaj Szafran, Paulina Wiecinska. “2-carboxyethyl acrylate as a new monomer preventing negative effect of oxygen inhibition in gelcasting of alumina.” Ceramics International 42 12 (2016): Pages 13682-13688.
[2] Naveed Ullah . “Coupling of carboxymethyl starch with 2-carboxyethyl acrylate: A new sorbent for the wastewater remediation of methylene blue.” Environmental Research 219 (2023): Article 115091.
[3] Amit K. Tripathi, Donald C. Sundberg*, Jenna Vossoughi. “Partitioning of 2-Carboxyethyl Acrylate between Water and Vinyl Monomer Phases Applied to Emulsion Polymerization: Comparisons with Hydroxy Acrylate and Other Vinyl Acid Functional Monomers.” Industrial Engineering Chemistry Research 54 9 (2015): 2447–2452.

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