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

•Anti-knock quality of four sugar-based cyclic ethers and levulinic esters determined.•Experiments carried out on both gasoline engine and constant volume chamber.•Results demonstrate good performance for levulinates and unsaturated cyclic ether.•Anti-knock behavior qualitatively explained with chem...

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Veröffentlicht in:	Fuel (Guildford) Jg. 202; H. C; S. 414 - 425
Hauptverfasser:	Tian, Miao, McCormick, Robert L., Luecke, Jon, de Jong, Ed, van der Waal, Jan C., van Klink, Gerard P.M., Boot, Michael D.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Kidlington Elsevier Ltd 15.08.2017 Elsevier BV Elsevier
Schlagworte:	Additives ADVANCED PROPULSION SYSTEMS Biofuels Bonding strength Chains Chemical bonds Compression Engine knock Engines Esters Ethers Fuels Furan Gasoline Ignition Intermediates Levulinate Molecular structure Octane booster Quality assessment Ring opening Spontaneous combustion Sugar MTHF Furan BDE PRF CFR MB SI ID LHV Engine knock bTDC KI Sugar Octane booster ML EL FEE CN EP IMEP IQT MON DCN Levulinate MAPO RON ASTM ETE SEPO aTDC
ISSN:	0016-2361, 1873-7153
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Abstract	•Anti-knock quality of four sugar-based cyclic ethers and levulinic esters determined.•Experiments carried out on both gasoline engine and constant volume chamber.•Results demonstrate good performance for levulinates and unsaturated cyclic ether.•Anti-knock behavior qualitatively explained with chemical kinetics considerations. 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 (modified ignition quality tester (IQT)). The results from both apparatuses demonstrate that ML, EL and FEE have superior anti-knock quality to the reference Euro95 gasoline. ETE, conversely, performed markedly worse than the reference fuel on both setups and might therefore be a more appropriate fuel additive 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 (CO) 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. Ethyl side chains on the cyclic ethers further accelerate the reaction rate. Importantly for future research, our results suggest that the modified (IQT) and engine experiments are interchangeable setups with respect to qualitative anti-knock quality evaluation of novel compounds.
AbstractList	•Anti-knock quality of four sugar-based cyclic ethers and levulinic esters determined.•Experiments carried out on both gasoline engine and constant volume chamber.•Results demonstrate good performance for levulinates and unsaturated cyclic ether.•Anti-knock behavior qualitatively explained with chemical kinetics considerations. 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 (modified ignition quality tester (IQT)). The results from both apparatuses demonstrate that ML, EL and FEE have superior anti-knock quality to the reference Euro95 gasoline. ETE, conversely, performed markedly worse than the reference fuel on both setups and might therefore be a more appropriate fuel additive 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 (CO) 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. Ethyl side chains on the cyclic ethers further accelerate the reaction rate. Importantly for future research, our results suggest that the modified (IQT) and engine experiments are interchangeable setups with respect to qualitative anti-knock quality evaluation of novel compounds. 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. 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 (modified ignition quality tester (IQT)). The results from both apparatuses demonstrate that ML, EL and FEE have superior anti-knock quality to the reference Euro95 gasoline. ETE, conversely, performed markedly worse than the reference fuel on both setups and might therefore be a more appropriate fuel additive 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. Ethyl side chains on the cyclic ethers further accelerate the reaction rate. Importantly for future research, our results suggest that the modified (IQT) and engine experiments are interchangeable setups with respect to qualitative anti-knock quality evaluation of novel compounds.
Author	van Klink, Gerard P.M. McCormick, Robert L. Tian, Miao Boot, Michael D. Luecke, Jon de Jong, Ed van der Waal, Jan C.
Author_xml	– sequence: 1 givenname: Miao orcidid: 0000-0002-9830-6109 surname: Tian fullname: Tian, Miao email: m.tian@tue.nl organization: Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands – sequence: 2 givenname: Robert L. surname: McCormick fullname: McCormick, Robert L. email: Robert.McCormick@nrel.gov organization: National Renewable Energy Laboratory, 15103 Denver West Parkway, Golden, CO 80401, United States – sequence: 3 givenname: Jon surname: Luecke fullname: Luecke, Jon email: Jon.Luecke@nrel.gov organization: National Renewable Energy Laboratory, 15103 Denver West Parkway, Golden, CO 80401, United States – sequence: 4 givenname: Ed orcidid: 0000-0001-5300-4230 surname: de Jong fullname: de Jong, Ed email: Ed.deJong@avantium.com organization: Avantium, Zekeringstraat 29, 1014 BV Amsterdam, The Netherlands – sequence: 5 givenname: Jan C. surname: van der Waal fullname: van der Waal, Jan C. email: JanKees.vanderWaal@avantium.com organization: Avantium, Zekeringstraat 29, 1014 BV Amsterdam, The Netherlands – sequence: 6 givenname: Gerard P.M. surname: van Klink fullname: van Klink, Gerard P.M. email: Gerard.vanKlink@avantium.com organization: Avantium, Zekeringstraat 29, 1014 BV Amsterdam, The Netherlands – sequence: 7 givenname: Michael D. surname: Boot fullname: Boot, Michael D. email: m.d.boot@tue.nl organization: Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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Keywords	MTHF Furan BDE PRF CFR MB SI ID LHV Engine knock bTDC KI Sugar Octane booster ML EL FEE CN EP IMEP IQT MON DCN Levulinate MAPO RON ASTM ETE SEPO aTDC
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Snippet	•Anti-knock quality of four sugar-based cyclic ethers and levulinic esters determined.•Experiments carried out on both gasoline engine and constant volume... 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... 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))...
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SubjectTerms	Additives ADVANCED PROPULSION SYSTEMS Biofuels Bonding strength Chains Chemical bonds Compression Engine knock Engines Esters Ethers Fuels Furan Gasoline Ignition Intermediates Levulinate Molecular structure Octane booster Quality assessment Ring opening Spontaneous combustion Sugar
Title	Anti-knock quality of sugar derived levulinic esters and cyclic ethers
URI	https://dx.doi.org/10.1016/j.fuel.2017.04.027 https://www.proquest.com/docview/2006793380 https://www.osti.gov/biblio/1352700
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