Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid

The development of a simple and durable catalytic system for the production of chemicals from a high concentration of a substrate is important for biomass conversion. In this manuscript, 5-hydroxymethylfurfural (HMF) was converted to 1-hydroxy-2,5-hexanedione (HHD) using the combination of commercia...

Full description

Bibliographic Details
Main Authors: Yanliang Yang, Dexi Yang, Chi Zhang, Min Zheng, Ying Duan
Format: Article
Language:English
Published: MDPI AG 2020-05-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/11/2475
_version_ 1797566981499518976
author Yanliang Yang
Dexi Yang
Chi Zhang
Min Zheng
Ying Duan
author_facet Yanliang Yang
Dexi Yang
Chi Zhang
Min Zheng
Ying Duan
author_sort Yanliang Yang
collection DOAJ
description The development of a simple and durable catalytic system for the production of chemicals from a high concentration of a substrate is important for biomass conversion. In this manuscript, 5-hydroxymethylfurfural (HMF) was converted to 1-hydroxy-2,5-hexanedione (HHD) using the combination of commercial Pd/C and acetic acid (AcOH) in water. The influence of temperature, H<sub>2</sub> pressure, reaction time, catalyst amount and the concentration of AcOH and HMF on this transformation was investigated. A 68% yield of HHD was able to be obtained from HMF at a 13.6 wt% aqueous solution with a 98% conversion of HMF. The resinification of intermediates on the catalyst was characterized to be the main reason for the deactivation of Pd/C. The reusability of the used Pd/C was studied to find that most of the activity could be recovered by being washed in hot tetrahydrofuran.
first_indexed 2024-03-10T19:34:11Z
format Article
id doaj.art-e4fba55691274cbd8405b08f7ce27e93
institution Directory Open Access Journal
issn 1420-3049
language English
last_indexed 2024-03-10T19:34:11Z
publishDate 2020-05-01
publisher MDPI AG
record_format Article
series Molecules
spelling doaj.art-e4fba55691274cbd8405b08f7ce27e932023-11-20T01:52:00ZengMDPI AGMolecules1420-30492020-05-012511247510.3390/molecules25112475Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic AcidYanliang Yang0Dexi Yang1Chi Zhang2Min Zheng3Ying Duan4Henan Key Laboratory of Function-Oriented Porous Material, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, ChinaHenan Key Laboratory of Function-Oriented Porous Material, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, ChinaHenan Key Laboratory of Function-Oriented Porous Material, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, ChinaHenan Key Laboratory of Function-Oriented Porous Material, College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471934, ChinaCollege of Food and Drug, Luoyang Normal University, Luoyang 471934, ChinaThe development of a simple and durable catalytic system for the production of chemicals from a high concentration of a substrate is important for biomass conversion. In this manuscript, 5-hydroxymethylfurfural (HMF) was converted to 1-hydroxy-2,5-hexanedione (HHD) using the combination of commercial Pd/C and acetic acid (AcOH) in water. The influence of temperature, H<sub>2</sub> pressure, reaction time, catalyst amount and the concentration of AcOH and HMF on this transformation was investigated. A 68% yield of HHD was able to be obtained from HMF at a 13.6 wt% aqueous solution with a 98% conversion of HMF. The resinification of intermediates on the catalyst was characterized to be the main reason for the deactivation of Pd/C. The reusability of the used Pd/C was studied to find that most of the activity could be recovered by being washed in hot tetrahydrofuran.https://www.mdpi.com/1420-3049/25/11/2475HMF1-hydroxy-2,5-hexanedioneacetic acidPd/Chigh concentration
spellingShingle Yanliang Yang
Dexi Yang
Chi Zhang
Min Zheng
Ying Duan
Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid
Molecules
HMF
1-hydroxy-2,5-hexanedione
acetic acid
Pd/C
high concentration
title Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid
title_full Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid
title_fullStr Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid
title_full_unstemmed Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid
title_short Preparation of 1-Hydroxy-2,5-hexanedione from HMF by the Combination of Commercial Pd/C and Acetic Acid
title_sort preparation of 1 hydroxy 2 5 hexanedione from hmf by the combination of commercial pd c and acetic acid
topic HMF
1-hydroxy-2,5-hexanedione
acetic acid
Pd/C
high concentration
url https://www.mdpi.com/1420-3049/25/11/2475
work_keys_str_mv AT yanliangyang preparationof1hydroxy25hexanedionefromhmfbythecombinationofcommercialpdcandaceticacid
AT dexiyang preparationof1hydroxy25hexanedionefromhmfbythecombinationofcommercialpdcandaceticacid
AT chizhang preparationof1hydroxy25hexanedionefromhmfbythecombinationofcommercialpdcandaceticacid
AT minzheng preparationof1hydroxy25hexanedionefromhmfbythecombinationofcommercialpdcandaceticacid
AT yingduan preparationof1hydroxy25hexanedionefromhmfbythecombinationofcommercialpdcandaceticacid