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Title: Anti-knock quality of sugar derived levulinic esters and cyclic ethers

Abstract

Here, the objective of this paper is to investigate the anti-knock quality of sugar-derived levulinic esters (methyl levulinate (ML) and ethyl levulinate (EL)) and cyclic ethers (furfuryl ethyl ether (FEE) and ethyl tetrahydrofurfuryl ether (ETE)). To this end, combustion experiments were carried out in both an engine and a constant volume autoignition device. The results from both apparati demonstrate that ML, EL and FEE have superior anti-knock quality than the reference Euro95 gasoline. ETE, conversely, performed markedly worse than the reference fuel on both setups and might therefore be a more appropriate fuel for compression ignition engines. The main reason of the distinctions in anti-knock quality can be found in the molecular structure of the neat biofuels. ML and EL are levulinic esters, with a ketone (C=O) functionality and an ester (C(=O)-O) group on the carbon chain. They can readily produce stable intermediates during the auto-ignition process, thereby slowing down the overall reaction rate. The unsaturated cyclic ether (FEE) has very strong ring C-H bonds. However, the saturated cyclic ether (ETE) has weak ring C-H bonds, which facilitate more readily ring opening reactions. Long side chains on the cyclic ethers further accelerate the reaction rate. Importantly for future research, ourmore » results suggest that IQT and engine experiments are interchangeable setups with respect to qualitative anti-knock quality evaluation of novel compounds.« less

Authors:
ORCiD logo; ; ; ORCiD logo; ; ;
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Vehicle Technologies Office (EE-3V)
OSTI Identifier:
1352700
Alternate Identifier(s):
OSTI ID: 1357741
Report Number(s):
NREL/JA-5400-67575
Journal ID: ISSN 0016-2361; S0016236117304076; PII: S0016236117304076
Grant/Contract Number:  
DE347AC36-99GO10337; AC36-08GO28308
Resource Type:
Published Article
Journal Name:
Fuel
Additional Journal Information:
Journal Name: Fuel Journal Volume: 202 Journal Issue: C; Journal ID: ISSN 0016-2361
Publisher:
Elsevier
Country of Publication:
United Kingdom
Language:
English
Subject:
33 ADVANCED PROPULSION SYSTEMS; sugar; engine knock; octane booster; levulinate; furan

Citation Formats

Tian, Miao, McCormick, Robert L., Luecke, Jon, de Jong, Ed, van der Waal, Jan C., van Klink, Gerard P. M., and Boot, Michael D.. Anti-knock quality of sugar derived levulinic esters and cyclic ethers. United Kingdom: N. p., 2017. Web. https://doi.org/10.1016/j.fuel.2017.04.027.
Tian, Miao, McCormick, Robert L., Luecke, Jon, de Jong, Ed, van der Waal, Jan C., van Klink, Gerard P. M., & Boot, Michael D.. Anti-knock quality of sugar derived levulinic esters and cyclic ethers. United Kingdom. https://doi.org/10.1016/j.fuel.2017.04.027
Tian, Miao, McCormick, Robert L., Luecke, Jon, de Jong, Ed, van der Waal, Jan C., van Klink, Gerard P. M., and Boot, Michael D.. Tue . "Anti-knock quality of sugar derived levulinic esters and cyclic ethers". United Kingdom. https://doi.org/10.1016/j.fuel.2017.04.027.
@article{osti_1352700,
title = {Anti-knock quality of sugar derived levulinic esters and cyclic ethers},
author = {Tian, Miao and McCormick, Robert L. and Luecke, Jon and de Jong, Ed and van der Waal, Jan C. and van Klink, Gerard P. M. and Boot, Michael D.},
abstractNote = {Here, the objective of this paper is to investigate the anti-knock quality of sugar-derived levulinic esters (methyl levulinate (ML) and ethyl levulinate (EL)) and cyclic ethers (furfuryl ethyl ether (FEE) and ethyl tetrahydrofurfuryl ether (ETE)). To this end, combustion experiments were carried out in both an engine and a constant volume autoignition device. The results from both apparati demonstrate that ML, EL and FEE have superior anti-knock quality than the reference Euro95 gasoline. ETE, conversely, performed markedly worse than the reference fuel on both setups and might therefore be a more appropriate fuel for compression ignition engines. The main reason of the distinctions in anti-knock quality can be found in the molecular structure of the neat biofuels. ML and EL are levulinic esters, with a ketone (C=O) functionality and an ester (C(=O)-O) group on the carbon chain. They can readily produce stable intermediates during the auto-ignition process, thereby slowing down the overall reaction rate. The unsaturated cyclic ether (FEE) has very strong ring C-H bonds. However, the saturated cyclic ether (ETE) has weak ring C-H bonds, which facilitate more readily ring opening reactions. Long side chains on the cyclic ethers further accelerate the reaction rate. Importantly for future research, our results suggest that IQT and engine experiments are interchangeable setups with respect to qualitative anti-knock quality evaluation of novel compounds.},
doi = {10.1016/j.fuel.2017.04.027},
journal = {Fuel},
number = C,
volume = 202,
place = {United Kingdom},
year = {2017},
month = {8}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1016/j.fuel.2017.04.027

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Cited by: 10 works
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Works referencing / citing this record:

Ethanolic gasoline, a lignocellulosic advanced biofuel
journal, January 2019

  • Howard, Mícheál Séamus; Issayev, Gani; Naser, Nimal
  • Sustainable Energy & Fuels, Vol. 3, Issue 2
  • DOI: 10.1039/c8se00378e

A review of furfural derivatives as promising octane boosters
journal, September 2017

  • Ershov, M. A.; Grigor’eva, E. V.; Guseva, A. I.
  • Russian Journal of Applied Chemistry, Vol. 90, Issue 9
  • DOI: 10.1134/s1070427217090051