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Single Step Process for Conversion of Furfural to Tetrahydrofuran

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Single Step Process for Conversion of Furfural to Tetrahydrofuran (19) TZZ ___T (11) EP 2 951 165 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 307/08 (2006.01) 04.10.2017 Bulletin 2017/40 (86) International application number: (21) Application number: 14724507.0 PCT/IN2014/000072 (22) Date of filing: 30.01.2014 (87) International publication number: WO 2014/118806 (07.08.2014 Gazette 2014/32) (54) SINGLE STEP PROCESS FOR CONVERSION OF FURFURAL TO TETRAHYDROFURAN EINSTUFIGES VERFAHREN ZUR UMWANDLUNG VON FURFURAL IN TETRAHYDROFURAN PROCÉDÉ EN UNE ÉTAPE POUR LA CONVERSION DE FURFURAL EN TÉTRAHYDROFURANE (84) Designated Contracting States: (74) Representative: Towler, Philip Dean AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Dehns GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO St Bride’s House PL PT RO RS SE SI SK SM TR 10 Salisbury Square London EC4Y 8JD (GB) (30) Priority: 30.01.2013 IN 249DE2013 (56) References cited: (43) Date of publication of application: US-A1- 2010 099 895 09.12.2015 Bulletin 2015/50 • SURAPAS SITTHISA ET AL: (73) Proprietor: Council of Scientific and Industrial "Hydrodeoxygenation of Furfural Over Research Supported Metal Catalysts: A Comparative Study New Delhi- 110001 (IN) of Cu, Pd and Ni", CATALYSIS LETTERS, KLUWER ACADEMIC PUBLISHERS-PLENUM (72) Inventors: PUBLISHERS, NE, vol. 141, no. 6, 29 March 2011 • RODE, Chandrasekhar, Vasant (2011-03-29), pages784-791, XP019905804, ISSN: Pune 411008 1572-879X, DOI: 10.1007/S10562-011-0581-7 Maharashtra (IN) • EDUARDO J. GARCÍA-SUÁREZ ET AL: "Versatile • BIRADAR, Narayan Shamrao dual hydrogenation-oxidation nanocatalysts for Pune 411008 the aqueous transformation of biomass-derived Maharashtra (IN) platform molecules", GREEN CHEMISTRY, vol. • HENGNE, Amol Mahalingappa 14, no. 5, 29 February 2012 (2012-02-29), pages Pune 411008 1434-1439, XP055124579, ISSN: 1463-9262, DOI: Maharashtra (IN) 10.1039/c2gc35176e Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 951 165 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 951 165 B1 Description FIELD OF THE INVENTION 5 [0001] The present invention relates to single step process for production of tetrahydrofuran (THF), an industrially useful solvent by hydrogenation of furfural using Pd/C catalyst. BACKGROUND OF THE INVENTION 10 [0002] Utilization of biomass has received a lot of attention for the development of a sustainable society. Manufacture of organic commodity chemicals from biomass is one of the most important methods of future biomass utilization because biomass is the only renewable source of carbon. Lignocelluloses biomass acts as a more promising feedstock for downstream applications which is more abundant, cheaper and potentially more sustainable. [0003] Furfuralis typically used as a precursor inthe production of tetrahydrofuran (THF), animportant industrial solvent. 15 [0004] Furfural is obtained from the dehydration of pentoses, five carbon sugars, such as xylose and arabinose, commonly obtained by acid-catalyzed digestion of hemicellulose-rich agricultural wastes. The acid hydrolysis of pentose sugars followed by dehydration of three water molecules gives furfural (C5). Furfural (FFR) deserves an attention as a potential platform molecule for production of variety of value added chemicals and fuels such as furan, furfuryl alcohol (FA), tetrahydrofurfuryl alcohol (THFA), 2-methyl furan (2-MF) tetrahydrofuran and 2-methyl tetrahydrofuran (2-MTHF), 20 in which tetrahydrofuran can be produced by decarbonylation of furfural to furan under reductive conditions and then subsequently hydrogenated to tetrahydrofuran (THF). It possesses wide applications; it can be used as solvent, monomer for polymer and chemical. [0005] However depending upon reaction conditions and catalytic properties, hydrogenation of FFR gives variety of products, all of which are important intermediates in the chemical industry. 25 [0006] Conventionally, THF can be produced by number of different routes including dehydration of 1,4-butanediol (BDO) and hydrogenation of maleic anhydride, all these processes contains multi-step synthesis by using reagents and metal complexes for production of THF, out of these one is starting from acetylene and formaldehyde in the presence of a cuprous acetylene complex to form butynediol (Reppe Process), while these processes were dependent on petroleum feedstock. These processes suffer from a variety of deficiencies such as multi-step synthesis, heavy metal complexes, 30 reagents and harsh reaction conditions which is directly relevant to environmental hazardous. [0007] Hence, these drawbacks may be overcome by either novel catalytic system and/or a single step process for synthesis of THF from furfural which bio-renewable. [0008] There are many supported noble (Pt, Pd, Ru, Rh) and non-noble (Cu, Ni,) metals that have been reported for the hydrogenation of FFR. Mahajani et al in Ind. Eng. Chem. Res., 2003, 42, 3881-3885 reported 5%Pt/C catalyst to 35 study kinetics of FFR hydrogenation to FA, the order he found was 0.85 at 403-448 K temperature and 1.03-2.06 MPa H2 pressure. [0009] Baijun et al in Applied Catalysis A: General, 1998, 171, 117-122 reported Raney nickel catalyst for furfural hydrogenation to furfuryl alcohol with 98 % selectivity. Twin catalyst system for the continuous conversion of furfural to THF through intermediate furan in supercritical Co2 with high selectivity to THF is reported by M.Poliokoff et.al. in Angew. 40 Chem. Int. Ed., 2010, 49, 8856-8859. [0010] Guha J. Catal., 1985, 91, 254-262 reported vapour phase decarbonylation of furfural over Pd-Al2O3 catalyst, deactivation of catalyst found by cocking Pd-Al2O3 catalyst. Resasco in Catal Lett, 2011, 141, 784-791 studied the different silica supported metal catalyst for the hydrogenation of furfural, he proposed 1% Pd/SiO2 catalyst give 20% THF with 69% conversion in a continuous fixed bed reactor. 45 [0011] Nagaraja et al. in J. Mol. Catal. A: Chemical, 2007, 278, 29-37 reported Cu based catalyst for coupling route highlighting the combination FFR hydrogenation and dehydrogenation of cyclohexanol in vapour phase conditions. Vapour phase hydrogenation of FFR studied over Ni/SiO2 catalyst to THFAL via furfuryl alcohol in two step strategy having no selectivity found to be THF. [0012] Recently Rafael et al.in Green Chem., 2012, 14, 1434-1439 reported hydrogenation of furfural using carbon- 50 supported Pd NPs with 90% conversion of FFR and 80% selectivity to THF on micro reactor.In "The electrocatalytic hydrogenation of furanic compounds in a continuous electrocatalytic membrane reactor" by Sara K. Green, Jechan Lee, Hyung Ju Kim, Geoffrey A. Tompsett, Won Bae Kim and George W. Huber in Green Chem., 2013, 15, 1869-1879, demonstrate the use of a continuous-flow electrocatalytic membrane reactor for the reduction of aqueous solutions of furfural into furfuryl alcohol (FA), tetrahydrofurfuryl alcohol (THFA), 2-methylfuran (MF) and 2-methyltetrahydrofuran 55 (MTHF). Protons needed for hydrogenation were obtained from the electrolysis of water at the anode of the reactor. Pd was identified as the most active monometallic catalyst of 5 different catalysts tested for the hydrogenation of aqueous furfural with hydrogen gas in a high-throughput reactor. Thus Pd/C was tested as a cathode catalyst for the electrocatalytic hydrogenation of furfural. At a power input of 0.1W, Pd/C was 4.4 times more active (per active metal site) as a cathode 2 EP 2 951 165 B1 catalystin the electrocatalytic hydrogenationof furfural than Pt/C. The main products forthe electrocatalytic hydrogenation of furfural were FA (54-100% selectivity) and THFA (0-26% selectivity). MF and MTHF were also detected in selectivities of 8%. Varying the reactor temperature between 30 °C and 70 °C had a minimal effect on reaction rate for furfural conversion. Using hydrogen gas at the anode, in place of water electrolysis, produced slightly higher rates of product 5 formation at a lower power input. Sparging hydrogen gas on the cathode had no effect on reaction rate or selectivity, and was used to examine the addition of recycling loops to the continuous electrocatalytic membrane reactor. [0013] A cursory review of prior arts reveal that there is still a scope in the art to provide an effective catalytic system that provides conversion rates with higher selectivity towards tetrahydrofuran. 10 OBJECTIVES OF THE INVENTION [0014] Main object of the present invention is to provide single step process for the production of tetrahydrofuran (THF), an industrially useful solvent by hydrogenation of furfural (FFR) using Pd/C catalyst. [0015] Another object of the present invention is to provide an effective catalytic system for the conversion of FFR into 15 THF, an industrially useful solvent with higher conversion rates and good selectivity. SUMMARY OF THE INVENTION [0016] Accordingly, present invention provides a one step process for the synthesis of Tetrahydrofuran (THF) from 20 furfural in both batch and continuous modes comprising: reacting furfural at a concentration in the range of 5 to 20 % in the presence of Palladium metal based carbon supported catalyst wherein the Palladium metal loading on carbon is in the range of 1% to 5%, at a temperature of 493 K in presence of hydrogen at a pressure in the range of 3 to 4 MPa for batch mode and a temperature ranging from 473-493 K and 3-3.5 MPa pressure for continuous mode, to obtain THF with 10% to 41% selectivity and related ring hydrogenated products, wherein conversion percentage of furfural is 100%. 25 [0017] In an embodiment of the present invention, the concentration of furfural is 5% by weight.
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