- Comprehensive investigation of the biomass derived furfuryl alcohol oligomer formation over tungsten oxide catalysts
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The feasibility of using tungsten oxide catalysts for furfuryl alcohol (FA) oligomerization reaction was investigated in the liquid phase at 100°C and ambient pressure. Five dimers (2,2′-difurylmethane, 2-(2-furylmethyl)-5-methylfuran, difurfuryl ether, 4-furfuryl-2-pentenoic acid γ-lactone, 5-fufuryl-furfuryl alcohol) and two trimers (2,5-difurfurylfuran and 2,2′-(furylmethylene)bis(5-methylfuran)) were observed in GC and GC/MS, while Infrared (IR) and Raman spectroscopy provided the co-existence of conjugated diene and diketone molecular structures, respectively. It was observed that C9-C15 oligomers' selectivity decreased as the reaction time increased. Ether bridge and terminal alcohol are dominant FA dimers which are very similar to sulfuric acid (homogeneous catalysis) catalyzed dehydration/condensation reaction of FA.
- Chan, Xiaojun,Nan, Wei,Mahajan, Devinder,Kim, Taejin
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- Efficient synthesis of niobium pentoxide nanowires and application in ethanolysis of furfuryl alcohol
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Nb2O5 nanowires with high specific surface area and crystallinity were prepared by using ammonium oxalate and an acetic acid solvent system. The nanomaterial was applied in ethanolysis of furfuryl alcohol (FA), and the yield of the product, 2-(ethoxymethyl)furan (FEE), achieved was up to 79.6%. Compared to mesoporous Nb2O5 materials and other porous materials, the residence time of FEE on the surface of the catalyst is shorter, and the yield of ethyl levulinate (EL) is lower. Furthermore, a high temperature calcination treatment can change the acid sites and acidity type distribution on the nanowire surface. By XRD, NH3-TPD, IR, and TG-DTA determination methods, it was found that the weak and medium-strong acid sites on the surface of Nb2O5 nanowires were reduced after a 300 °C treatment, and the amount of strong acid was relatively higher. According to the catalytic performance test data and acidity determination, it was concluded that more weak acid and medium-strong acid sites improve the conversion of furfuryl alcohol to FEE, and the strong acid sites promote further conversion of FEE to EL.
- Zhang, Zhenwei,Wang, Peng,Wu, Zeying,Yue, Chuanjun,Wei, Xuejiao,Zheng, Jiwei,Xiang, Mei,Liu, Baoliang
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Read Online
- Furfuryl alcohol in synthesis of levulinic acid esters and difurylmethane with Fe and Rh complexes
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The possibility of synthesis of levulinic acid esters by the reaction of furfuryl alcohol with aliphatic alcohols in the system CCl4-Fe(acac) 3 was studied.
- Khusnutdinov,Baiguzina,Smirnov,Mukminov,Dzhemilev
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Read Online
- Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
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The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
- Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
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- Catalyst-free synthesis of biodiesel precursors from biomass-based furfuryl alcohols in the presence of H2O and air
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Production of biodiesel from biomass resources usually requires elongation of carbon numbers from typical C5 and C6 platform molecules through C-C coupling reactions, which were catalyzed by acid, base or metal catalysts traditionally. Herein, a catalyst-free method was developed to produce bis(furan-2-yl)methane derivatives (BFMs) from furfuryl alcohol derivatives (FAs) in the presence of H2O and air without any other additional catalysts. An 81% yield of bis(5-methylfuran-2-yl)methane (BMFM) can be obtained from 5-methylfurfuryl alcohol (5-MFA) and a 59% total yield of C11 biodiesel was obtained from 5-methylfurfural (5-MF). In addition, a H2O and air mediated free radical decarboxylation mechanism was proposed based on the detailed mechanistic studies. This strategy offers a green, low-cost and environmentally friendly approach to synthesize biodiesel precursors from biomass based platform molecules.
- Qin, Shengxiang,Li, Teng,Zhang, Man,Liu, Hongyu,Yang, Xin,Rong, Nianxin,Jiang, Jun,Wang, Yalin,Zhang, Hua,Yang, Weiran
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p. 6326 - 6334
(2019/12/03)
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- A one-pot conversion furfural, 5 - hydroxymethyl furfural furan
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A one-pot conversion furfural, 5 - hydroxymethyl furfural furan method, characterized by comprising the following steps: the furfural, 5 - hydroxymethyl furfural, catalyst, solvent are added in the reactor with a condensation device, in an inert atmosphere, in the 80 - 250 °C reaction temperature, stirring, reaction 0.5 - 30 h, ice water bath cooling. The invention will be furfural, 5 - hydroxymethyl furfural two substrates through a pot conversion of furan, simplify operation process, avoiding the loss of the material and the step of, maximum utilization of resources; in suitable process conditions, greatly shortens the reaction time, the production cost is reduced, thereby improving the production efficiency; in the normal pressure on the temperate conditions, high expectations for production equipment, in accordance with the principles of safe production; and forming the lignin is suitable for pre-treatment of wood cellulose acid or catalytic generation of furfural, 5 - hydroxymethyl furfural mixture one-pot conversion of furan, to proceed from the biomass resources for producing tetrahydrofuran.
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Paragraph 0030-0033
(2021/05/12)
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- Defining Pt-compressed CO2 synergy for selectivity control of furfural hydrogenation
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The development of a sustainable methodology for catalytic transformation of biomass-derived compounds to value-added chemicals is highly challenging. Most of the transitions are dominated by the use of additives, complicated reaction steps and large volumes of organic solvents. Compared to traditional organic solvents, alternative reaction media, which could be an ideal candidate for a viable extension of biomass-related reactions are rarely explored. Here, we elucidate a selective and efficient transformation of a biomass-derived aldehyde (furfural) to the corresponding alcohol, promoted in compressed CO2 using a Pt/Al2O3 catalyst. Furfural contains a furan ring with CC and an aldehyde group, and is extremely reactive in a hydrogen atmosphere, resulting in several by-products and a threat to alcohol selectivity as well as catalyst life. The process described has a very high reaction rate (6000 h-1) with an excellent selectivity/yield (99%) of alcohol, without any organic solvents or metal additives. This strategy has several key features over existing methodologies, such as reduced waste, and facile product separation and purification (reduced energy consumption). Combining the throughput of experimental observation and molecular dynamics simulation, indeed the high diffusivity of compressed CO2 controls the mobility of the compound, and eventually maintains the activity of the catalyst. Results are also compared for different solvents and solvent-less conditions. In particular, combination of an effective Pt catalyst with compressed CO2 provides an encouraging alternative solution for upgradation of biomass related platform molecules.
- Chatterjee, Maya,Chatterjee, Abhijit,Ishizaka, Takayuki,Kawanami, Hajime
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p. 20190 - 20201
(2018/06/11)
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- A two-phase system for the clean and high yield synthesis of furylmethane derivatives over -SO3H functionalized ionic liquids
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A new and effective unique two-phase reaction system is investigated for the high yield production of tri(furyl)methane from furfural and furan. This strategy includes the use of an acidic aqueous phase (water + -SO3H functionalized IL) and furan phase, which significantly suppresses polymer formation, thereby increasing the yield of tri(furyl)methane. Furan serves as a reactant as well as an extraction solvent for the recovery of the condensation products. For comparison, different -SO3H functionalized ionic liquids are prepared and their performances evaluated for the condensation of furan and furfural. The ionic liquids with alkyl chain linkers are found to be more effective and acidic than those with imidazolium linked N-sulfonic acids. In addition, an increase in carbon chain length between imidazole/tri-ethylamine/pyridine and -SO3H, increases the catalytic activity of the respective ionic liquids. Among the several prepared ionic liquids, the strongly acidic imidazolium based butylsulfonic acid 6 shows the best activity with a maximum condensation product yield of 84%. This strategy offers a significantly high yield of the condensation products of furan and furfural compared to the traditional mineral acid route. The activity and stability of the -SO3H functionalized 6 is confirmed from seven successful recycles, in which there is no reduction in its activity. Finally, this new strategy is successfully extended for the condensation of furan derivatives (e.g. furan and 2-methylfuran) with several different aldehydes, ketones and alcohols.
- Shinde,Rode
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p. 4804 - 4810
(2017/10/19)
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- PREPARATION OF PHENYL COMPOUNDS
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The invention relates to a method for preparing a compound comprising two phenyl groups by reacting a bisfuranic compound with a dienophile; and to such compounds.
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Page/Page column 21-22
(2017/08/01)
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- CATALYST AND CATALYTIC PROCESS FOR THE ETHERIFICATION/REDUCTION OF FURFURYL DERIVATIVES TO TETRAHYDROFURFURYL ETHERS
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The invention relates to a method for producing tetrahydrofurfuryl ethers, characterised in that it involves carrying out consecutive etherification/reduction reactions based on a compound containing at least one furan ring, in the presence of at least one alcohol and at least one catalyst, optionally in the presence of H2. The catalytic process can be carried out in a cascade reaction ("one-pot"), operating under soft reaction conditions and without a solvent.
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Paragraph 0106; 0107
(2015/11/16)
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- The effect of pH on the formation of aroma compounds produced by heating a model system containing l-ascorbic acid with l-threonine/l-serine
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The identification of aroma compounds, formed from the reactions of l-ascorbic acid with l-threonine/l-serine at five different pH values (5.00, 6.00, 7.00, 8.00, or 9.55) and 143 ± 2 °C for 2 h, was performed using a SPME-GC-MS technique, and further use
- Yu, Ai-Nong,Zhang, Ai-Dong
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experimental part
p. 214 - 219
(2011/12/14)
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- METHOD FOR COUPLING LIVING CATIONIC POLYMERS
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A method for coupling a living cationic polymer is disclosed, said method comprising reacting the living cationic polymer with an organic compound having at least 2 furan rings in its molecule, said reaction taking place in the presence of a Lewis acid. Preferably, the living cationic polymer is first prepared by polymerizing at least one monomer selected from isobutylene, isoprene or a styrenic monomer using a specific initiator, this reaction also being carried out in the presence of a Lewis acid.
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- A new, non-iterative asymmetric synthesis of long-chain 1,3-polyols
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A new approach to the asymmetric synthesis of pentadeca-1,3,5,7,9,11,13,15-octols and their derivatives is presented. It is based on the Sharpless asymmetric dihydroxylation (AD) of 4,4'-methylene[(1R,1'S,6R,6'S)-6-acetoxycyclohept-3-en-1-yl]bis(4-methoxybenz oate) (9), derived from a double [3+4] cycloaddition of the 1,1,3-trichloro-2-oxyallyl cation with 2,2'-methylenedifuran (1). The diol (-)-10, obtained in 98.4% ee from 9 with 'AD-mix-β(5 x), was oxidised into (2R and 2S,4S,6R)-tetrahydro-2-hydroxy-6-{(4S,6S)-{6-hydroxy-4-[(4-methoxybenzoyl)o xy]cyclohept-1-en-1-yl}-2-oxopropyl}-2H-pyran-4-yl 4-methoxybenzoates ((-)-18). By the combinations of Evans' anti and Nasaraka's syn reductions of aldol (-)-18 with the double Mitsunobu reaction, 16 diastereomeric pentadeca-1,3,5,7,9,11,13,15-octols and analogues can be obtained, in principle, with high enantio- and diastereoselectivities.
- Schwenter, Marc-Etienne,Vogel, Pierre
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p. 4091 - 4103
(2007/10/03)
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- Synthesis of Calixfuran Macrocycles and Evidence for Gas-phase Ammonium Ion Complexation
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Furan and 2-hydroxymethylfuran reacted under Lewis acidic conditions to yield oligomeric furylmethane compounds 5 and 6.Difurylmethane 5 was also obtained via the reaction of 2-furyllithium with bromochloromethane or reaction with 2-furaldehyde, followed by in situ reduction of the resulting lithium alkoxide with sodium boranuide-trifluoroacetic acid mixture.The trimeric furan compound 6a could also be prepared from furyllithium by a similar route.Oligomers 5 and 6 were utilised for a subsequent Lewis acid-catalysed cyclisation to afford calixfurans, i.e. cyclic tetramer 2a, and small quantities of the cyclic pentamer 2b, hexamer 2c and octamer 2e.Traces of cyclic heptamer 2d could also be detected under certain conditions.Chemical ionisation mass spectrometry using ammonia gas demonstrates that the calixfurans and their acyclic precursors are capable of chelating hydrogen and ammonium ions in the gas phase.
- Musau, Richard M.,Whiting, Andrew
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p. 2881 - 2888
(2007/10/02)
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- The Synthesis of Furan-derived Calixarenes
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Furan and 2-hydroxymethylfuran were reacted under Lewis acidic oligomeric precursors, for a subsequent Lewis acid catalysed cyclisation to afford the furan based calixarenes, i.e. cyclic tetramer 2a, and small quantities of the cyclic pentamer 2b, hexamer 2c and octamer 2d.
- Musau, Richard M.,Whiting, Andrew
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p. 1029 - 1031
(2007/10/02)
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- Syntheses of Tetraoxaquaterene Derivatives
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Several new dimethyl and tetramethyl tetraoxaquaterenes, 3d and 3e, have been prepared in order to synthesize the oxygen analogues of porphyrin.The reaction between furan and a ketone using an acidic catalyst gave the cyclic tetramer, tetraquaterene, and oligomers.On the other hand, in the case of furan and the aldehyde, only linear oligomers were isolated.The condensation of furan-containing dimers with carbonyl compounds, both ketone and aldehyde, except formaldehyde, gave the tetraoxaquaterene.In the case of formaldehyde, the yield of cyclic tetramer was neglijable.
- Tanaka, Sanae,Tomokuni, Hidehiko
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p. 991 - 994
(2007/10/02)
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- ALKYLATION OF FURAN, THIOPHENE, AND PYRROLE WITH FURFURYL ALCOHOL IN THE PRESENCE OF THE STRONGLY ACIDIC AMBERLYST 15 SULFO CATION-EXCHANGE RESIN
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The corresponding 2-furylhetarylmethanes were obtained by the reaction of furan, thiophene, or pyrrole with furfuryl alcohol in the presence of the strongly acidic Amberlyst 15 cation-exchange resin in the H+ form.The alkylation of furan and thiophene takes place regiospecifically in the 2 position, whereas 2-furyl-2-pyrrolyl- and 2-furyl-3-pyrrolylmethane in a ratio of 6.2:1 are formed in the case of pyrrole.
- Iovel', I. G.,Gol'dberg, Yu. Sh.,Shimanskaya, M. V.
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p. 613 - 616
(2007/10/02)
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