2-(Perfluorobutyl)ethyl acrylate Chemical Properties

Boiling point:

164 °C

Density 

1.414

refractive index 

1.310

Flash point:

52 °C

storage temp. 

Store at 2-8 ℃

solubility 

Chloroform (Soluble), Ethyl Acetate (Slightly)

form 

clear liquid

color 

Colorless to Light yellow

Specific Gravity

1.440

EPA Substance Registry System

1,1,2,2-Tetrahydroperfluorohexyl acrylate (52591-27-2)

Safety Information

RIDADR 

UN 3272 3/PG III

HazardClass 

3

PackingGroup 

III

HS Code 

2916120090

2-(Perfluorobutyl)ethyl acrylate Usage And Synthesis

Uses

2-(Perfluorobutyl)ethyl Acrylate can be used as an acrylic resin surface modifier with high water repellency and oil repellency for coating agents. It can also be used in a super concentrated emulsion method to prepare a solid sheet polycarboxylic acid water reducing agent.

Application

2-(Perfluorobutyl)ethyl acrylate has been used in a wide range of scientific research applications. It has been used to create polymers for biomedical applications, such as drug delivery systems and tissue engineering scaffolds. It has also been used to create polymers for industrial applications, such as coatings and adhesives. In addition, it has been used to create polymers for energy applications, such as fuel cells and solar cells.

Synthesis

1H,1H,2H,2H-nonafluoro-1-hexanol (52.8 g) as fluoro alcohol and triethylamine (50 g) were dissolved in 500 ml of tetrahydrofuran. A solution of 18.1 g of acryloyl chloride as acid chloride in 100 ml of tetrahydrofuran was dropped in this solution over 2 hours while the mixture was being cooled in ice and stirred. After the completion of the dropping, the resulting white precipitate was filtrated and tetrahydrofuran and triethylamine were removed from the filtrate using a rotary evaporator. NMR measurement revealed that the resulting compound was 1H,1H,2H,2H-nonafluorohexyl acrylate.

Research

Since the bioaccumulation of the degradation products of fluoropolymer with a long Rf side chain (C ≥ 8) has a potential environmental risk, it is necessary to design fluoropolymer coating with a short Rf side chain. Honda et al. studied the effect of α-substituent on the wetting behavior and molecular motion at the surfaces of poly{2-(perfluorobutyl)ethyl acrylate} [PFA-C4], poly{2-(perfluorobutyl)ethyl methacrylate} [PFMA-C4], poly{2-(perfluorobutyl)ethyl α-fluoroacrylate} [PFFA-C4], and poly{2-(perfluorobutyl)ethyl α-chloroacrylate} [PFClA-C4] films. In the case of PFA-Cy with long Rf groups [y ≥ 8], the mobility of the side chains is low at room temperature because of the crystallization of the Rf groups at the surface region[1].

References

[1] Koji Honda . "Effect of α-substituents on molecular motion and wetting behaviors of poly(fluoroalkyl acrylate) thin films with short fluoroalkyl side chains." Polymer 55 24 (2014): Pages 6303-6308.

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