PMID- 35147297
OWN - NLM
STAT- MEDLINE
DCOM- 20220408
LR  - 20220408
IS  - 1864-564X (Electronic)
IS  - 1864-5631 (Linking)
VI  - 15
IP  - 7
DP  - 2022 Apr 7
TI  - Effective Oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran by an Acetal 
      Protection Strategy.
PG  - e202200059
LID - 10.1002/cssc.202200059 [doi]
AB  - An acetal protection strategy for 5-hydroxymethylfurfural (HMF) was used to 
      obtain 2,5-diformyfuran (DFF) using concentrated HMF solutions and a gamma-Al(2) O(3) 
      -supported Ru catalyst (Ru/gamma-Al(2) O(3) ). The HMF-acetal with 1,3-propanediol 
      can be oxidized to DFF-acetal with a yield of 84.0 % at an HMF conversion of 
      94.2 % from a 50 wt % solution. In contrast, aerobic oxidation of nonprotected 
      HMF using a 10 wt % solution afforded DFF only in a moderate yield (52.3 %). 
      Kinetic studies indicated that the six-membered ring acetal group not only 
      prevents side reactions but also accelerates aerobic oxidation of the -CH(2) OH 
      moiety to -CHO under retention of the acetal functionality. Organic deposits 
      formed during the reaction explained the significant decrease in the activity of 
      the Ru/gamma-Al(2) O(3) catalyst, which could be recovered neither by washing in 
      water or organic solvents, nor by a calcination-reduction treatment. Sonication 
      of the used Ru/gamma-Al(2) O(3) catalyst in an aqueous NaOH solution successfully 
      removed the deposits and allowed reuse of the catalyst for at least four times 
      without activity loss.
CI  - (c) 2022 Wiley-VCH GmbH.
FAU - Boonyakarn, Tat
AU  - Boonyakarn T
AD  - Institute for Catalysis, Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, 
      001-0021, Japan.
FAU - Wiesfeld, Jan J
AU  - Wiesfeld JJ
AD  - Institute for Catalysis, Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, 
      001-0021, Japan.
FAU - Asakawa, Miyuki
AU  - Asakawa M
AD  - Institute for Catalysis, Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, 
      001-0021, Japan.
FAU - Chen, Lulu
AU  - Chen L
AD  - Laboratory of Inorganic Chemistry and Catalysis, Department of Chemical 
      Engineering and Chemistry, Eindhoven University of Technology, PO Box 513, 5600 
      MB, Eindhoven, The Netherlands.
FAU - Fukuoka, Atsushi
AU  - Fukuoka A
AD  - Institute for Catalysis, Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, 
      001-0021, Japan.
FAU - Hensen, Emiel J M
AU  - Hensen EJM
AD  - Laboratory of Inorganic Chemistry and Catalysis, Department of Chemical 
      Engineering and Chemistry, Eindhoven University of Technology, PO Box 513, 5600 
      MB, Eindhoven, The Netherlands.
FAU - Nakajima, Kiyotaka
AU  - Nakajima K
AUID- ORCID: 0000-0002-3774-3209
AD  - Institute for Catalysis, Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, 
      001-0021, Japan.
LA  - eng
GR  - JPMJMI19E3/JST-MIRAI/
GR  - 20H05879/JSPS Grant-in-Aid/
GR  - 18KK0135/JSPS Fostering Joint International Research (B)/
GR  - 20A1002/Cooperative Research Program of Institute for Catalysis, Hokkaido 
      University/
PT  - Journal Article
DEP - 20220223
PL  - Germany
TA  - ChemSusChem
JT  - ChemSusChem
JID - 101319536
RN  - 0 (Acetals)
RN  - 0 (Furans)
RN  - 059QF0KO0R (Water)
RN  - 70ETD81LF0 (5-hydroxymethylfurfural)
RN  - DJ1HGI319P (Furaldehyde)
RN  - L4HT8N2Z72 (2,5-diformylfuran)
SB  - IM
MH  - *Acetals
MH  - *Furaldehyde/analogs & derivatives
MH  - Furans
MH  - Kinetics
MH  - Water
OTO - NOTNLM
OT  - 5-hydroxymethylfurfural
OT  - biomass
OT  - diformylfuran
OT  - heterogeneous catalysis
OT  - oxidation
EDAT- 2022/02/12 06:00
MHDA- 2022/04/09 06:00
CRDT- 2022/02/11 08:47
PHST- 2022/02/11 00:00 [revised]
PHST- 2022/01/10 00:00 [received]
PHST- 2022/02/12 06:00 [pubmed]
PHST- 2022/04/09 06:00 [medline]
PHST- 2022/02/11 08:47 [entrez]
AID - 10.1002/cssc.202200059 [doi]
PST - ppublish
SO  - ChemSusChem. 2022 Apr 7;15(7):e202200059. doi: 10.1002/cssc.202200059. Epub 2022 
      Feb 23.