A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration

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A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration. / Pyo, Sang-Hyun; Dishisha, Tarek; Dayankac, Secil; Gerelsaikhan, Jargalan; Lundmark, Stefan; Rehnberg, Nicola; Hatti-Kaul, Rajni.

I: Green Chemistry, Vol. 14, Nr. 7, 2012, s. 1942-1948.

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskrift

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Pyo, Sang-Hyun ; Dishisha, Tarek ; Dayankac, Secil ; Gerelsaikhan, Jargalan ; Lundmark, Stefan ; Rehnberg, Nicola ; Hatti-Kaul, Rajni. / A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration. I: Green Chemistry. 2012 ; Vol. 14, Nr. 7. s. 1942-1948.

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TY - JOUR

T1 - A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration

AU - Pyo, Sang-Hyun

AU - Dishisha, Tarek

AU - Dayankac, Secil

AU - Gerelsaikhan, Jargalan

AU - Lundmark, Stefan

AU - Rehnberg, Nicola

AU - Hatti-Kaul, Rajni

PY - 2012

Y1 - 2012

N2 - Methacrylic acid was produced in high yield by an integrated process involving bioconversion of 2-methyl-1,3-propanediol (2M1,3PD) to 3-hydroxy-2-methylpropionic acid (3H2MPA) via 3-hydroxy-2-methylpropanal (3H2MPAL), and catalytic dehydration of the resulting acid. Whole cells of Gluconobacter oxydans grown on glycerol-based culture medium were used as the catalyst for oxidative biotransformation that involved alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) enzymes in the organism. The effect of several reaction parameters on bioconversion in a batch system was investigated to obtain 95–100% conversion of 2M1,3PD with over 95% selectivity to 3H2MPA. The optimum conditions for bioconversion were pH 6–7.5, 25–30 °C, 5–10 g substrate and 2.6 g cell (dry weight) per liter. Higher substrate concentrations led to enzyme inhibition and incomplete conversion. Loss of catalytic activity was noted during recycling of the cells. The cells were active for a longer period when used for biotransformation of 20 g per L of substrate in a continuous reactor with cell retention. The product of the bio-oxidation, 3H2MPA, was converted using titanium dioxide at 210 °C to give methacrylic acid (MA) with a yield of over 85%. The integrated process provides a new environmentally benign route for production of methacrylic acid from 2-methyl-1,3-propanediol, an industrial by-product, compared with the conventional acetone-cyanohydrin (ACH) process.

AB - Methacrylic acid was produced in high yield by an integrated process involving bioconversion of 2-methyl-1,3-propanediol (2M1,3PD) to 3-hydroxy-2-methylpropionic acid (3H2MPA) via 3-hydroxy-2-methylpropanal (3H2MPAL), and catalytic dehydration of the resulting acid. Whole cells of Gluconobacter oxydans grown on glycerol-based culture medium were used as the catalyst for oxidative biotransformation that involved alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) enzymes in the organism. The effect of several reaction parameters on bioconversion in a batch system was investigated to obtain 95–100% conversion of 2M1,3PD with over 95% selectivity to 3H2MPA. The optimum conditions for bioconversion were pH 6–7.5, 25–30 °C, 5–10 g substrate and 2.6 g cell (dry weight) per liter. Higher substrate concentrations led to enzyme inhibition and incomplete conversion. Loss of catalytic activity was noted during recycling of the cells. The cells were active for a longer period when used for biotransformation of 20 g per L of substrate in a continuous reactor with cell retention. The product of the bio-oxidation, 3H2MPA, was converted using titanium dioxide at 210 °C to give methacrylic acid (MA) with a yield of over 85%. The integrated process provides a new environmentally benign route for production of methacrylic acid from 2-methyl-1,3-propanediol, an industrial by-product, compared with the conventional acetone-cyanohydrin (ACH) process.

KW - ACH process

KW - Gluconobacter oxydans

KW - alcohol dehydrogenase

KW - aldehyde dehydrogenase

KW - titanium dioxide

U2 - 10.1039/C2GC35214A

DO - 10.1039/C2GC35214A

M3 - Article

VL - 14

SP - 1942

EP - 1948

JO - Green Chemistry

T2 - Green Chemistry

JF - Green Chemistry

SN - 1463-9270

IS - 7

ER -