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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 LU ; Dishisha, Tarek LU ; Dayankac, Secil; Gerelsaikhan, Jargalan; Lundmark, Stefan LU ; Rehnberg, Nicola and Hatti-Kaul, Rajni LU (2012) In Green Chemistry 14(7). p.1942-1948
Abstract
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... (More)
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. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
ACH process, Gluconobacter oxydans, alcohol dehydrogenase, aldehyde dehydrogenase, titanium dioxide
in
Green Chemistry
volume
14
issue
7
pages
1942 - 1948
publisher
Royal Society of Chemistry
external identifiers
  • wos:000305627500018
  • scopus:84862883379
ISSN
1463-9270
DOI
10.1039/C2GC35214A
language
English
LU publication?
yes
id
60d3920a-5ff7-433f-bf3b-23e221af638b (old id 2628903)
alternative location
http://pubs.rsc.org/en/content/articlelanding/2012/GC/C2GC35214A
date added to LUP
2012-06-27 11:44:07
date last changed
2017-02-19 03:20:35
@article{60d3920a-5ff7-433f-bf3b-23e221af638b,
  abstract     = {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.},
  author       = {Pyo, Sang-Hyun and Dishisha, Tarek and Dayankac, Secil and Gerelsaikhan, Jargalan and Lundmark, Stefan and Rehnberg, Nicola and Hatti-Kaul, Rajni},
  issn         = {1463-9270},
  keyword      = {ACH process,Gluconobacter oxydans,alcohol dehydrogenase,aldehyde dehydrogenase,titanium dioxide},
  language     = {eng},
  number       = {7},
  pages        = {1942--1948},
  publisher    = {Royal Society of Chemistry},
  series       = {Green Chemistry},
  title        = {A new route for the synthesis of methacrylic acid from 2-methyl-1,3-propanediol by integrating biotransformation and catalytic dehydration},
  url          = {http://dx.doi.org/10.1039/C2GC35214A},
  volume       = {14},
  year         = {2012},
}