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. 2020 Jan 1;10(1):70.
doi: 10.3390/biom10010070.

Novel and Efficient Synthesis of Phenethyl Formate via Enzymatic Esterification of Formic Acid

Minguk Shin  1 , Jeongbae Seo  1 , Yesol Baek  1 , Taek Lee  1 , Min Jang  2 , Chulhwan Park  1
Affiliations

Novel and Efficient Synthesis of Phenethyl Formate via Enzymatic Esterification of Formic Acid

Minguk Shin et al. Biomolecules. .

Abstract

Current methods for the production of esters, including chemical synthesis and extraction from natural sources, are hindered by low yields and environmental pollution. The enzymatic synthesis of these compounds could help overcome these problems. In this study, phenethyl formate, a commercially valuable formate ester, was synthesized using commercial immobilized lipases. The effects of specific enzymes, enzyme concentration, formic acid:phenethyl alcohol molar ratio, temperature, and solvent were studied in order to optimize the synthesis conditions, which were identified as 15 g/L of Novozym 435 enzyme, a 1:5 formic acid:phenethyl alcohol molar ratio, a 40 °C reaction temperature, and 1,2-dichloroethane as the solvent. Under these conditions, phenethyl formate was obtained in a conversion yield of 95.92%. In addition, when 1,2-dichloroethane was replaced with toluene as the solvent, the enzyme could be recycled for at least 20 reactions with a steady conversion yield above 92%, testifying to the economic aspects of the process. The enzymatic synthesis of phenethyl formate using the proposed method is more environmentally friendly than methods currently employed in academic and laboratory settings. Moreover, the method has the potential to enhance the value-added properties of formic acid owing to its downstream use in the production of commercially essential esters.

Keywords: enzyme reuse; esterification; formic acid; lipase; phenethyl formate; value-added chemical.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Byproducts (red dashed rectangle) from the transesterification of an acetic acid derivative (A) and the esterification of formic acid (B).
Figure 2
Figure 2
Effect of Novozym 435 concentration on the formation of phenethyl formate. The conversion yield (%) was calculated by GC analysis.
Figure 3
Figure 3
Effect of formic acid:phenethyl alcohol molar ratio on the Novozym 435-catalyzed synthesis of phenethyl formate. The conversion yield (%) was calculated by GC analysis.
Figure 4
Figure 4
Mechanism for the lipase-catalyzed synthesis of phenethyl formate.
Figure 5
Figure 5
Effect of reaction temperature on the Novozym 435-catalyzed synthesis of phenethyl formate. The conversion yield (%) was calculated by GC analysis.
Figure 6
Figure 6
Effect of solvent log P on the Novozym 435-catalyzed synthesis of phenethyl formate. The conversion yield (%) was calculated by GC analysis.
Figure 7
Figure 7
Recycling of Novozym 435 enzymatic activity in 1,2-dichloroethane and toluene. The conversion yield (%) was calculated by GC analysis.
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