Lipase‐catalyzed synthesis of geranyl acetate in <i>n</i>‐hexane with membrane‐mediated water removal

Bartling, Karsten; Thompson, Judith U. S.; Pfromm, Peter H.; Czermak, Peter; Rezac, Mary E.

doi:10.1002/bit.1193

Cited by 42 publications

(35 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Authors concluded that the use of membrane permitted to enhance the reaction yield from 94 to 100% at 30°C and acetic acid to geraniol molar ratio of 1:1 [15].…”

Section: Resultsmentioning

confidence: 98%

Solvent-free geranyl oleate production by enzymatic esterification

Paroul

Grzegozeski

Chiaradia

et al. 2010

Bioprocess Biosyst Eng

View full text Add to dashboard Cite

This work reports the optimization of geranyl propionate production by esterification of geraniol and propionic acid in a solvent-free system using a commercial lipase as catalyst. For this purpose, a sequential strategy was performed applying two experimental designs. The operating conditions that optimized geranyl propionate production were determined to be 40 °C, geraniol to propionic acid molar ratio of 3:1, 150 rpm and 10 wt% of enzyme, with a resulting reaction conversion of about 93%. After determining the optimum reaction parameters, a kinetic study was carried out evaluating the influence of substrates molar ratio, enzyme concentration and temperature on reaction conversion. Results obtained in this step allow to conclude that an excess of alcohol (acid to alcohol molar ratio of 1:6), relatively low enzyme concentration (5 wt%), temperature of 40 °C and substrates molar ratio of 1:1 afforded nearly complete reaction conversion after 30 min of reaction. New experimental data on enzymatic esterification of geraniol and propionic acid for geranyl propionate production are reported in this work, showing a promising perspective of the technique to overcome the well-known drawbacks of the chemical-catalyzed route.

show abstract

“…Authors concluded that the use of membrane permitted to enhance the reaction yield from 94 to 100% at 30°C and acetic acid to geraniol molar ratio of 1:1 [15].…”

Section: Resultsmentioning

confidence: 98%

Solvent-free geranyl oleate production by enzymatic esterification

Paroul

Grzegozeski

Chiaradia

et al. 2010

Bioprocess Biosyst Eng

View full text Add to dashboard Cite

show abstract

“…Bartling et al [20] investigated the use of membranes for removing water on the enzymatic synthesis of geranyl acetate catalyzed by C. antarctica lipase in n-hexane organic system. The authors concluded that the use of membrane permitted to enhance the reaction yield from 94% to 100% at 30°C and acetic acid to geraniol molar ratio of 1:1.…”

Section: Enzymatic Production Of Citronellyl and Geranyl Propionatementioning

confidence: 99%

Solvent-Free Production of Bioflavors by Enzymatic Esterification of Citronella (Cymbopogon winterianus) Essential Oil

Paroul

Grzegozeski

Chiaradia

et al. 2011

Appl Biochem Biotechnol

View full text Add to dashboard Cite

Enzymatic esterification of citronella essential oil towards the production of geranyl and citronellyl esters may present great scientific and technological interest due to the well-known drawbacks of the chemical-catalyzed route. In this context, this work reports the maximization of geranyl and citronellyl esters production by esterification of oleic and propionic acids in a solvent-free system using a commercial immobilized lipase as catalyst. Results of the reactions showed that the strategy adopted for the experimental design proved to be useful in evaluating the effects of the studied variables on the reaction conversion using Novozym 435 as catalyst. The operating conditions that maximized the production of each ester were determined, leading, in a general way, to conversions of about 90% for all systems. New experimental data on enzymatic esterification of crude citronella essential oil for geranyl and citronellyl esters production in solvent-free system are reported in this work.

show abstract

“…This approach has for example proven to be promising for the production of polymers 3,4 , anticancer and antiviral drugs 5 , aromas and fragrances 6,7 , and surfactants 8 . Performing biocatalysis in organic solvents is advantageous mainly because the solubility and stability of substrates and products are increased, thereby facilitating their transformation 1,9 , and because undesirable reactions, including hydrolysis, racemization, polymerization, and decomposition may be reduced when compared to aqueous systems 1,10 .…”

Section: Introductionmentioning

confidence: 99%

“…Here we report a study of the immobilization of CALB on fumed silica by lyophilization, and the catalytic activity of the resulting preparations for a model esterification that we used previously 6,7,42 . Adsorption of CALB on fumed silica pre-lyophilization from aqueous solution at different pH levels and silica-to-enzyme ratios was investigated by fluorescence microscopy.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of Candida antarctica Lipase B on fumed silica

Cruz

Pfromm

Rezac

2009

Process Biochemistry

Self Cite

View full text Add to dashboard Cite

Enzymes are usually immobilized on solid supports or solubilized when they are to be used in organic solvents with poor enzyme solubility. We have reported previously on a novel immobilization method for s. Carlsberg on fumed silica with results that reached some of the best previously reported catalytic activities in hexane for this enzyme. Here we extend our method to Candida antarctica lipase B (CALB) as an attractive target due to the many potential applications of this enzyme in solvents. Our CALB/fumed silica preparations approached the catalytic activity of commercial Novozym 435 for a model esterification in hexane at 90wt% fumed silica (relative to the mass of the preparation). An intriguing observation was that the catalytic activity at first increases as more fumed silica was made available to the enzyme but then decreased precipitously when 90wt% fumed silica was exceeded. This was not the case for s. Carlsberg where the catalytic activity leveled off at high relative amounts of fumed silica. We determined adsorption kinetics, performed variations of the pre-immobilization aqueous pH, determined the stability, and applied fluorescence microscopy to the preparations. A comparison with recent concepts by Gross et al. may point towards a rationale for an optimum intermediate surface coverage for some enzymes on solid supports.

show abstract

Lipase‐catalyzed synthesis of geranyl acetate in n‐hexane with membrane‐mediated water removal

Cited by 42 publications

References 22 publications

Solvent-free geranyl oleate production by enzymatic esterification

Solvent-free geranyl oleate production by enzymatic esterification

Solvent-Free Production of Bioflavors by Enzymatic Esterification of Citronella (Cymbopogon winterianus) Essential Oil

Immobilization of Candida antarctica Lipase B on fumed silica

Contact Info

Product

Resources

About