Furfuryl Ethyl Ether:  Important Aging Flavor and a New Marker for the Storage Conditions of Beer

Vanderhaegen, Bart; Neven, Hedwig; Daenen, Luk; Verstrepen, Kevin J.; Verachtert, Hubert; Derdelinckx, Guy

doi:10.1021/jf035412g

Cited by 56 publications

(40 citation statements)

References 29 publications

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“…The elemental mappings showed fairly homogeneous metal dispersions; no particles of bulk zirconia or alumina were observed, which is consistent with the PXRD studies. The EDS analyses of (Zr) SSIE -beta and (ZrAl) SSIE -beta indicated that they possess similar atomic ratio Si/(Zr+Al) (16)(17)(18)(19) (Table 2), which is consistent with the fact that the molar amounts of Zr or (Zr+Al) added to deAl-beta were the same for the two materials ( Table 1). The atomic ratio Al/Zr was higher for (ZrAl) SSIE -beta than (Zr) SSIE -beta (1.2 and 0.03, respectively), and the Si/Al ratio was much lower for (ZrAl) SSIE -beta (35 compared to 588 (Zr) SSIE -beta), which is consistent with the fact that (ZrAl) SSIE -beta was obtained via SSIE for both Zr and Al.…”

Section: Beta Type Materialssupporting

confidence: 66%

“…Besides FA, various useful bio-products, such as alkyl furfuryl ethers (FEs), levulinate esters (LEs), angelica lactones (AnLs), levulinic acid (LA), and -valerolactone (GVL) can be produced from Fur (Scheme 1) [13][14][15]. For example, FEs are used as blending components of gasoline [16,17] and as flavours [18,19]. LEs are useful chemical intermediates for producing coatings, resins and flavour preparations [20,21], anticancer agents, pesticides and insecticides [22].…”

Section: Introductionmentioning

confidence: 99%

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Integrated reduction and acid-catalysed conversion of furfural in alcohol medium using Zr,Al-containing ordered micro/mesoporous silicates

Antunes

Lima

Neves

et al. 2016

Applied Catalysis B: Environmental

104

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Ordered porous silicates of the type TUD-1 and zeolite beta possessing zirconium and aluminium sites were evaluated as eco-friendly heterogeneous, multifunctional catalysts for the integrated reduction-acid conversion of furfural (Fur, industrially produced from hemicellulosic components of biomass) to useful bio-products, namely, furfuryl alcohol (FA), alkyl furfuryl ethers (FEs), alkyl levulinate esters (LEs), levulinic acid (LA), angelica lactones (AnLs), and γ-valerolactone (GVL); the bio-products spectrum was obtained by GC × GC-ToFMS. Carrying out the one-pot conversion of Fur to bioproducts using a multifunctional catalyst is challenging since various reactions are involved and it is difficult to control all of these to meet high reaction efficiencies and selectivities. Aiming at designing improved multifunctional catalysts for this reaction system, the TUD-1 and zeolite beta type silicates possessing zirconium and aluminium sites in different ratios were prepared and characterised on microstructural and molecular levels. Systematic characterisation, catalytic testing using 2-butanol as dual functional solvent-H-donor, and kinetic modelling studies were performed using the Zr,Al-containing micro-and mesoporous materials. Different steps of the overall reaction of Fur were studied separately starting from intermediate products using the same materials, which helped understand the influence of the material properties on 2 reactivity of intermediates and reaction selectivity. Zr-sites of the silicate catalysts were essential for effectively initialising the overall process (reduction of Fur to FA), and for the reduction of LEs to GVL; the co-presence of Al-sites promoted acid-catalysed steps (FA to FEs, LEs, AnLs, LA). The good stability of the catalysts was verified by catalytic and characterisation studies of the spent catalysts.

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Section: Beta Type Materialssupporting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Integrated reduction and acid-catalysed conversion of furfural in alcohol medium using Zr,Al-containing ordered micro/mesoporous silicates

Antunes

Lima

Neves

et al. 2016

Applied Catalysis B: Environmental

104

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“…Similarly, the test indicated acetoin production by S. marcescens MG1 and also by its swrI mutant in the presence of 10 M C 4 -HSL, but not in its absence (data not shown). A more specific analysis of 2,3-butanediol and its precursors diacetyl and acetoin by gas chromatography coupled to mass spectrometry was performed as previously described (15). Briefly, gas chromatography was performed by using a Fisons GC 8000 gas chromatograph (Fisons, Mainz, Germany) equipped with a Chrompack CP-WAX-52-CB column (Varian, Palo Alto, CA), and total ion mass chromatograms were obtained with a Fisons MD 800 quadrupole mass spectrometer (Fisons, Mainz, Germany) and analyzed using the Masslab software program (ThermoQuest, Manchester, United Kingdom) for identification and quantification of volatiles.…”

Section: Vol 188 2006 Notesmentioning

confidence: 99%

N -Acyl- l -Homoserine Lactone Quorum Sensing Controls Butanediol Fermentation in Serratia plymuthica RVH1 and Serratia marcescens MG1

et al. 2006

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Butanediol fermentation in two Serratia species is shown to be affected by N-acyl-L-homoserine lactonedependent quorum sensing. Knockout of quorum-sensing signal production caused a shift towards enhanced acid production, resulting in early growth arrest, which was reversible by the addition of synthetic signal molecules.The Enterobacteriaceae are commonly divided into two groups with different fermentation pathways (4). Members of genera such as Escherichia, Salmonella, and Shigella use the mixed-acid pathway, causing strong acidification of their environment due to the production of large amounts of acids, including acetate, lactate, succinate, and formate. In contrast, members of Klebsiella, Enterobacter, Serratia, and a number of other genera ferment glucose predominantly to 2,3-butanediol (18). In the latter case, the production of acidic products is limited because a significant amount of pyruvate from glycolysis is channeled into the butanediol pathway (6, 9). The production of neutral compounds is ecologically relevant since it allows butanediol fermenters to prevent lethal acidification as cells approach stationary phase. In Klebsiella terrigena, the LysR-type transcriptional activator BudR appears to regulate at least part of the 2,3-butanediol pathway (10). Recently, microarray analysis showed that the production of 2,3-butanediol in Vibrio cholerae is also regulated by the transcriptional activator AphA, in addition to the LysR-type transcriptional activator AlsR (8). The AphA activator is, in turn, regulated by multiple quorum-sensing systems that act in parallel. System 1 uses the CAI-1 autoinducer of unknown structure, while system 2 uses AI-2, a furanosyl borate diester, to trigger a phosphorelay circuit (1,2,7,11,19). These systems are homologues of the Vibrio harveyi systems (11) but differ from the LuxIR paradigm in Vibrio fischeri, in which LuxI synthesizes the Nacyl-L-homoserine lactone (AHL) signaling molecules and the AHL-activated LuxR protein functions as a transcriptional activator triggering a response (5).We recently initiated a study of biofilm-forming bacteria from a food-processing environment (16). One isolate, designated RVH1, was identified as Serratia plymuthica (17), and we recently characterized its LuxIR-homologous quorum-sensing system, SplIR. The SplIR quorum-sensing system regulates the production of an extracellular chitinase, protease, nuclease, and antibacterial compound (R. Van Houdt, P. Moons, A. Aertsen, A. Jansen, K. Vanoirbeek, M. Daykin, P. Williams, and C. W. Michiels, submitted for publication). In the current study, we report that 2,3-butanediol production in this strain is quorum sensing regulated via the same AHL-dependent system. Furthermore, we confirmed our observations in Serratia marcescens MG1 (previously Serratia liquefaciens MG1), the type species of the Serratia genus. The demand and manufacture of 2,3-butanediol are still increasing worldwide (annual rate of 4 to 7%) due to a variety of applications, such as its use as a liquid fuel additive, and t...

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“…It can be converted to the bio-products furfuryl alcohol (FA), furfuryl alkyl ethers (FEs), levulinate esters (LEs), levulinic acid (LA), angelica lactone isomers (AnLs) and -valerolactone (GVL) [2][3][4] (Scheme 1), useful in different sectors of the chemical industry. FA, industrially produced via hydrogenation of Fur, is used in the foundry 3 industry [5], and FEs are used as blending components of gasoline [6,7] and as flavour compounds [8,9]. LEs are used as oxygenate fuel additives [10][11][12], solvents, and to produce plasticizers and flavouring agents [13][14].…”

Section: Introductionmentioning

confidence: 99%

One-pot conversion of furfural to useful bio-products in the presence of a Sn,Al-containing zeolite beta catalyst prepared via post-synthesis routes

Antunes

Lima

Neves

et al. 2015

Journal of Catalysis

137

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Aiming at the valorisation of furfural (Fur) via sustainable routes based on process intensification and heterogeneous catalysis, the one-pot conversion of this renewable platform chemical to useful bio-products, namely furfuryl alkyl ethers (FEs), levulinate esters (LEs), levulinic acid (LA), angelica lactones (AnLs) and -valerolactone (GVL), was investigated using a single heterogeneous catalyst, in 2-butanol, at 120 ºC. Various chemical 2 reactions are involved in this process, which requires catalysts with active sites for acid and reduction chemistry. For this purpose, it was explored for the first time the catalytic potentialities of modified versions of zeolite beta containing Al and Sn sites prepared from commercially available nanocrystaline zeolite beta via post-synthesis partial dealumination followed by solid-state ion-exchange. The post-synthesis conditions influenced considerably the catalytic performances of these types of materials. The best-performing catalyst was (Sn) SSIE -beta1 with Si/(Al+Sn)=19 (Sn/Al=27.6), which led to total yield of bio-products of 83% at 86% Fur conversion, and exhibited steady catalytic performance for six consecutive runs. A systematic catalytic study using the prepared catalysts with different bio-products as substrates, together with the molecular level and microstructural characterisation of the materials, helped understand the effects of different material properties on the specific reaction pathways in the overall system. These studies led to mechanistic insights into the reaction network of Fur to the bio-products in alcohol media, upon which a kinetic model was developed for the first time. The superior performance of (Sn) SSIE -beta1 in various steps was related to the dealumination degree, dispersion and amount of Sn-sites, and acid properties.

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Furfuryl Ethyl Ether: Important Aging Flavor and a New Marker for the Storage Conditions of Beer

Cited by 56 publications

References 29 publications

Integrated reduction and acid-catalysed conversion of furfural in alcohol medium using Zr,Al-containing ordered micro/mesoporous silicates

Integrated reduction and acid-catalysed conversion of furfural in alcohol medium using Zr,Al-containing ordered micro/mesoporous silicates

N -Acyl- l -Homoserine Lactone Quorum Sensing Controls Butanediol Fermentation in Serratia plymuthica RVH1 and Serratia marcescens MG1

One-pot conversion of furfural to useful bio-products in the presence of a Sn,Al-containing zeolite beta catalyst prepared via post-synthesis routes

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