Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Probing direct carbon-carbon acylation of furans and long-chain acids over H-ZSM-5

Journal Article · · Applied Catalysis. A, General
 [1];  [2];  [3];  [4]
  1. Univ. of Pennsylvania, Philadelphia, PA (United States); University of Pennsylvania
  2. Univ. of Pennsylvania, Philadelphia, PA (United States)
  3. Univ. of Minnesota, Minneapolis, MN (United States); Univ. of Delaware, Newark, DE (United States)
  4. Univ. of Pennsylvania, Philadelphia, PA (United States); Univ. of Delaware, Newark, DE (United States)
The acylation of furan and 2-methylfuran (2-MF) with acetic acid (AA) and 1-hexanoic acid (HA) was studied over an H-ZSM-5 catalyst. Temperature-programmed desorption (TPD) measurements showed evidence that AA adsorbs strongly at Brønsted sites, with reaction to CO2 and acetone beginning at 523 K, while both furan and 2-MF oligomerize upon adsorption at room temperature. Steady-state, flow-reactor measurements demonstrate that selectivities for the acylation reactions can approach 100% below 523 K when reactions are operated in excess organic acids, with maximum conversion limited by equilibrium. Coking becomes important when the reaction is operated in excess furan or 2-MF and at high reactant concentrations, while ketonization products are observed when the reaction is performed above 523 K. Lastly, potential uses for the reactions are discussed.
Research Organization:
Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI); Univ. of Pennsylvania, Philadelphia, PA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Grant/Contract Number:
SC0001004
OSTI ID:
1594768
Journal Information:
Applied Catalysis. A, General, Journal Name: Applied Catalysis. A, General Journal Issue: C Vol. 577; ISSN 0926-860X
Publisher:
ElsevierCopyright Statement
Country of Publication:
United States
Language:
English

References (17)

Highly Selective Condensation of Biomass-Derived Methyl Ketones as a Source of Aviation Fuel journal April 2015
A 13C NMR Study of the Condensation Chemistry of Acetone and Acetaldehyde Adsorbed at the Brønsted Acid Sites in H-ZSM-5 journal February 1995
An Examination of Brønsted Acid Sites in H-[Fe]ZSM-5 for Olefin Oligomerization and Adsorption journal August 2002
High Pressure Cracking of n-Hexane Over H-ZSM-5 journal February 2013
Characterization of acylating intermediates formed on H-ZSM-5 journal February 2004
Selective ketonization of acetic acid over HZSM-5: The importance of acyl species and the influence of water journal August 2016
The acylation of propene by acetic acid over H-[Fe]ZSM-5 and H-[Al]ZSM-5 journal April 2004
Adsorption of Small Alkanes on ZSM-5 Zeolites: Influence of Brønsted Sites journal June 2016
Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans journal October 2016
Use of Solid Catalysts in Friedel−Crafts Acylation Reactions journal March 2006
A calorimetric study of simple bases in H-ZSM-5: a comparison with gas-phase and solution-phase acidities journal December 1993
Calorimetric Study of Alcohol and Nitrile Adsorption Complexes in H-ZSM-5 journal May 1997
What do we know about the acidity of solid acids? journal January 1999
Zeolite-catalysed C–C bond forming reactions for biomass conversion to fuels and chemicals journal January 2016
Methods to delay deactivation of zeolites on furan acylation: continuous liquid-phase technology and solvent effects journal January 2015
Adsorption and reaction properties of SnBEA, ZrBEA and H-BEA for the formation of p-xylene from DMF and ethylene journal January 2016
Direct carbon-carbon coupling of furanics with acetic acid over Brønsted zeolites journal September 2016

Similar Records

Kinetics of 2-Methylfuran Acylation with Fatty Acid Anhydrides for Biorenewable Surfactants
Journal Article · Tue Dec 08 19:00:00 EST 2020 · ACS Sustainable Chemistry & Engineering · OSTI ID:1865839

Adsorption of furan, hexanoic acid, and alkanes in a hierarchical zeolite at reaction conditions: Insights from molecular simulations
Journal Article · Thu Nov 26 19:00:00 EST 2020 · Journal of Computational Science · OSTI ID:1771017

Direct carbon-carbon coupling of furanics with acetic acid over Bronsted zeolites
Journal Article · Thu Sep 15 20:00:00 EDT 2016 · Science Advances · OSTI ID:1437643