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Selective Oxidation of 5-Hydroxymethylfurfural to 5-Hydroxymethyl-2-furancarboxylic Acid Using Gluconobacter oxydans

Sayed, Mahmoud LU ; Pyo, Sang Hyun LU ; Rehnberg, Nicola and Hatti-Kaul, Rajni LU (2019) In ACS Sustainable Chemistry and Engineering 7(4). p.4406-4413
Abstract


5-Hydroxymethylfurfural (HMF), an important biobased platform chemical, can be potentially oxidized to several products that can serve as versatile building blocks for polymers. 5-Hydroxymethyl-2-furan carboxylic acid (HMFCA) is formed by incomplete oxidation of HMF but the reaction often suffers from substrate inhibition and overoxidation to other products. In this study, resting cells of Gluconobacteroxydans DSM 50049 were shown to oxidize HMF quantitatively to HMFCA with exquisite selectivity. Complete conversion of 31.5 g L
-1
crude HMF to... (More)


5-Hydroxymethylfurfural (HMF), an important biobased platform chemical, can be potentially oxidized to several products that can serve as versatile building blocks for polymers. 5-Hydroxymethyl-2-furan carboxylic acid (HMFCA) is formed by incomplete oxidation of HMF but the reaction often suffers from substrate inhibition and overoxidation to other products. In this study, resting cells of Gluconobacteroxydans DSM 50049 were shown to oxidize HMF quantitatively to HMFCA with exquisite selectivity. Complete conversion of 31.5 g L
-1
crude HMF to HMFCA was achieved within 6 h under pH-controlled conditions. Initial productivity of 10 g L
-1
h
-1
was reduced to 2 g L
-1
h
-1
toward the end of the reaction. Thereafter, additional HMF added to the reaction mixture (12 g L
-1
) was converted up to 94% within 17 h with 100% selectivity resulting in final HMFCA concentration of 44.6 g L
-1
and yield of 6.2 g g
-1
cell dry weight. Recovery of HMFCA from the reaction could be achieved by adsorption to anion exchange resins Amberlite IRA-400 (Cl
-
form) and Ambersep 900 (OH
-
form), the former showing higher binding (169 mg/g resin) and product recovery. Alternatively, liquid-liquid extraction with ethyl acetate provided a facile separation technique for the recovery of pure HMFCA.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
5-Hydroxymethyl-2-furan carboxylic acid (HMFCA), 5-Hydroxymethylfurfural (HMF), Gluconobacter oxydans 50049, Selective oxidation, Whole cells biocatalyst
in
ACS Sustainable Chemistry and Engineering
volume
7
issue
4
pages
8 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85062087159
ISSN
2168-0485
DOI
10.1021/acssuschemeng.8b06327
project
STEPS – Sustainable Plastics and Transition Pathways
language
English
LU publication?
yes
id
bd8cd650-ac0b-4ff7-8674-d22ebd9217ba
date added to LUP
2019-03-06 12:46:42
date last changed
2019-12-03 02:03:05
@article{bd8cd650-ac0b-4ff7-8674-d22ebd9217ba,
  abstract     = {<p><br>
                                                         5-Hydroxymethylfurfural (HMF), an important biobased platform chemical, can be potentially oxidized to several products that can serve as versatile building blocks for polymers. 5-Hydroxymethyl-2-furan carboxylic acid (HMFCA) is formed by incomplete oxidation of HMF but the reaction often suffers from substrate inhibition and overoxidation to other products. In this study, resting cells of Gluconobacteroxydans DSM 50049 were shown to oxidize HMF quantitatively to HMFCA with exquisite selectivity. Complete conversion of 31.5 g L                             <br>
                            <sup>-1</sup><br>
                                                          crude HMF to HMFCA was achieved within 6 h under pH-controlled conditions. Initial productivity of 10 g L                             <br>
                            <sup>-1</sup><br>
                                                          h                             <br>
                            <sup>-1</sup><br>
                                                          was reduced to 2 g L                             <br>
                            <sup>-1</sup><br>
                                                          h                             <br>
                            <sup>-1</sup><br>
                                                          toward the end of the reaction. Thereafter, additional HMF added to the reaction mixture (12 g L                             <br>
                            <sup>-1</sup><br>
                                                         ) was converted up to 94% within 17 h with 100% selectivity resulting in final HMFCA concentration of 44.6 g L                             <br>
                            <sup>-1</sup><br>
                                                          and yield of 6.2 g g                             <br>
                            <sup>-1</sup><br>
                                                          cell dry weight. Recovery of HMFCA from the reaction could be achieved by adsorption to anion exchange resins Amberlite IRA-400 (Cl                             <br>
                            <sup>-</sup><br>
                                                          form) and Ambersep 900 (OH                             <br>
                            <sup>-</sup><br>
                                                          form), the former showing higher binding (169 mg/g resin) and product recovery. Alternatively, liquid-liquid extraction with ethyl acetate provided a facile separation technique for the recovery of pure HMFCA.                         <br>
                        </p>},
  author       = {Sayed, Mahmoud and Pyo, Sang Hyun and Rehnberg, Nicola and Hatti-Kaul, Rajni},
  issn         = {2168-0485},
  language     = {eng},
  month        = {02},
  number       = {4},
  pages        = {4406--4413},
  publisher    = {The American Chemical Society (ACS)},
  series       = {ACS Sustainable Chemistry and Engineering},
  title        = {Selective Oxidation of 5-Hydroxymethylfurfural to 5-Hydroxymethyl-2-furancarboxylic Acid Using Gluconobacter oxydans},
  url          = {http://dx.doi.org/10.1021/acssuschemeng.8b06327},
  doi          = {10.1021/acssuschemeng.8b06327},
  volume       = {7},
  year         = {2019},
}