Hydrogenation of levulinic acid with and without external hydrogen over Ni/SBA-15 catalyst

http://www.mnre.gov.in/schemes/grid-connected/biomass-powercogen/. Accessed 3 Mar 2011 Bozell JJ, Moens L, Elliott DC, Wang Y, Neuenscwander GG, Fitzpatrick SW, Bilski RJ, Jarnefeld JL (2000) Production of levulinic acid and use as a platform chemical for derived products. Resour Conserv Recycl 28:227–239. https://doi.org/10.1016/S0921-3449(99)00047-6 Gullon P, Romani A, Vila C, Garrote G, Parajo JC (2012) Potential of hydrothermal treatments in lignocellulose biorefineries. Biofuels Bioprod Biorefining 6:219–232 Hayes DJ (2009) An examination of biorefining processes, catalysts and challenges. Catal Today 145:138–151 He ZS (1999) Extraction of levulinic acid from paper-making black liquor. Chem Ind Eng 2:163–166 Dunlop AP, Smith S (1955) US Patent 2676186 Manzer LE (2003) US Patent 20030055270 Willems GJ, Liska J (1999) EP Patent 933348 Shilling WL (1996) US Patent 32355562 Crook LR, Jansen BA, Spencer KE, Watson DH (1996) GB Patent 1036694 Bart HJ, Reidetschlager J, Schatka K, Lehmann A (1994) Kinetics of esterification of levulinic acid with n-butanol by homogeneous catalysis. Ind Eng Chem Res 33:21–25 Varkolu M, Moodley V, Potwana FSW, Jonnalagadda SB, van Zyl WE (2017) Esterification of levulinic acid with ethanol over bio-glycerol derived carbon–sulfonic-acid. Reac Kinet Mech Catal 120:69–80 Kopetzki D, Antonietti M (2010) Transfer hydrogenation of levulinic acid under hydrothermal conditions catalyzed by sulfate as a temperature-switchable base. Green Chem 12:656–660 Deng L, Zhao Y, Li J, Fu Y, Liao B, Guo QX (2010) Conversion of levulinic acid and formic acid into γ-valerolactone over heterogeneous catalysts. Chemsuschem 3:1172–1175 Deng L, Li J, Lai DM, Fu Y, Guo QX (2009) Catalytic conversion of biomass-derived carbohydrates into γ-valerolactone without using an external H2 supply. Angew Chem Int Ed 48:6529–6532 Heeres H, Handana R, Chunai D, Rasrendra CB, Girisuta B, Heeres HJ (2009) Combined dehydration/(transfer)-hydrogenation of C6-sugars (D-glucose and D-fructose) to γ-valerolactone using ruthenium catalysts. Green Chem 11:1247–1255 Haan RJ, Lange JP, Petrus L (2007) US Patent 20070208183 Mehdi H, Fabios V, Tuba R, Bodor A, Mika LT, Horváth IT (2008) Integration of Homogeneous and heterogeneous catalytic processes for a multi-step conversion of biomass: from sucrose to levulinic acid, γ-valerolactone, 1,4-pentanediol, 2-methyl-tetrahydrofuran, and alkanes. Top Catal 48:49–54 Lange JP, Price R, Ayoub PM, Louis J, Petrus L, Clarke L, Gosselink H (2010) Valeric biofuels: a platform of cellulosic transportation fuels. Angew Chem Int Ed 49:4479–4483 Schuette HA, Thomas RW (1930) Normal valerolactone. iii. its preparation by the catalytic reduction of levulinic acid with hydrogen in the presence of platinum oxide. J Am Chem Soc 52:3010–3012 Kyrides LP, Groves W, Craver JK (1945) US Patent 2368366 Dunlop AP , Madden JW (1957) US Patent 2786852 Christian RV Jr, Brown HD, Hixon RM (1947) Derivatives of γ-valerolactone, 1,4-pentanediol and 1,4-Di-(β-cyanoethoxy)-pentane. J Am Chem Soc 69:1961–1963 Manzer LE (2003) US Patent 6617464 B2 Manzer LE (2004) Catalytic synthesis of α-methylene-γ-valerolactone: a biomass-derived acrylic monomer. Appl Catal A 272:249–256 Bourne RA, Stevens JG, Ke J, Poliakoff M (2007) Maximising opportunities in supercritical chemistry: the continuous conversion oflevulinic acid to γ-valerolactone in CO2. Chem Commun. https://doi.org/10.1039/B708754C Manzer LE, Hutchenson KW (2004) US Patent 2004254384 Yan ZP, Lin L, Liu S (2009) Synthesis of γ-valerolactone by hydrogenation of biomass-derived levulinic acid over Ru/C catalyst. Energy Fuels 23:3853–3858 Joo F, Beck MT (1975) Formation and catalytic properties of water-soluble phosphine complexes. React Kinet Catal Lett 2:257–263 Joo F, Toth Z, Beck MT (1977) Homogeneous hydrogenations in aqueous solutions catalyzed by transition metal phosphine complexes. Inorg Chim Acta 25:L61–L62 Osakada K, Ikariya T, Yoshikawa S (1982) Preparation and properties of hydride triphenyl-phosphine ruthenium complexes with 3-formyl (or acyl)propionate [RuH(ocochrchrcor′)(PPh3)3] (R = H, CH3, C2H5; R = H, CH3, C6H5) and with 2-formyl (or acyl) benzoate [RuH(o-OCCOC6H4COR′)(PPh3)3] (R′ = H, CH3). J Organomet Chem 231:79–90 Upare PP, Lee J-M, Hwang DW, Halligudi SB, Hwang YK, Chang J-S (2011) Selective hydrogenation of levulinic acid to γ-valerolactone over carbon-supported noble metal catalysts. J Ind Eng Chem 17:287–292 Upare PP, Hwang YK, Hwang DW, Lee J-H, Halligudi SB, Hwang J-S, Chang J-S (2011) Direct hydrocyclization of biomass-derived levulinic acid to 2-methyltetrahydrofuran over nanocomposite copper/silica catalysts. Chemsuschem 4:1749–1752 Mohan V, Raghavendra C, Pramod CV, Raju BD, Rao KSR (2014) Ni/H-ZSM-5 as a promising catalyst for vapour phase hydrogenation of levulinic acid at atmospheric pressure. RSC Adv 4:9660–9668 Dodds DR, Gross RA (2007) Chemicals from Biomass. Science 318:1250–1251 Corma A, Iborra S, Velty A (2007) Chemical routes for the transformation of biomass into chemicals. Chem Rev 107:2411–2502 Jessop PG (2011) Searching for green solvents. Green Chem 13:1391–1398 Horváth IT, Mehdi H, Fábos V, Boda L, Mika LT (2008) γ-Valerolactone—a sustainable liquid for energy and carbon-based chemicals. Green Chem 10:238–242 Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA (2010) Integrated catalytic conversion of γ-valerolactone to liquid alkenes for transportation fuels. Science 327:1110–1144 Kim SW, Son SU, Lee SL, Hyeon T, Chung YK (2000) Cobalt on mesoporous silica: the first heterogeneous pauson−khand catalyst. J Am Chem Soc 122:1550–1551 Iglesia E, Boudart M (1983) Decomposition of formic acid on copper, nickel, and copper-nickel alloys: I. preparation and characterization of catalysts. J Catal 84:204–213 Hengne AM, Malawadkar AV, Biradar NS, Rode CV (2014) Surface synergism of an Ag–Ni/ZrO2 nanocomposite for the catalytic transfer hydrogenation of bio-derived platform molecules. RSC Adv 4:9730–9736 Bulushev DA, Ross JRH (2011) Vapour phase hydrogenation of olefins by formic acid over a Pd/C catalyst. Catal Today 163:42–46 Yamamoto K, Sunagawa Y, Takaha hi H, Muramatsu A (2005) Metallic Ni nanoparticles confined in hexagonally ordered mesoporous silica material. Chem Commun 348–350. Chary KVR, Srikanth CS (2009) Selective hydrogenation of nitrobenzene to aniline over Ru/SBA-15 catalysts. Catal Lett 128:164–170 Li H, Xu Y, Yang H, Zhang F, Li H (2009) Ni-B amorphous alloy deposited on an aminopropyl and methyl co-functionalized SBA-15 as a highly active catalyst for chloronitrobenzene hydrogenation. J Mol Catal A: Chem 307:105–114 Zhao D, Feng J, Huo Q, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD (1998) Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores. Science 279:548–552 Gregg SJ, Sing KSW (1982) Adsorption, surface area and porosity, 2nd edn. Acadamic Press, New York Zhao DY, Huo Q, Feng J, Chmelka BF, Stucky GD (1998) Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures. J Am Chem Soc 120:6024–6036 Lihui Z, Jun HU, Songhai XIE, Honglai LIU (2007) Dispersion of active Au nanoparticles on mesoporous SBA-15 materials. Chin J Chem Eng 15(4):507–511. https://doi.org/10.1016/S1004-9541(07)60116-5 Rioux RM, Song H, Hoefelmeyer JD, Somorjai GA (2005) High-Surface-Area catalyst design: synthesis, characterization, and reaction studies of platinum nanoparticles in mesoporous SBA-15 silica. J Phys Chem B 109:2192–2202 Wang X, Wang P, Dong Z, Dong Z, Ma Z, Jiang J, Li R, Ma J (2010) Highly sensitive fluorescence probe based on functional SBA-15 for selective detection of Hg2+. Nanoscale Res Lett 5:1468–1473 Ladavos AK, Katsoulidis AP, Iosifidis A, Triantafyllidis KS, Pinnavaia TJ (2012) The BET equation, the inflection points of N2 adsorption isotherms and the estimation of specific surface area of porous solids. Micro Meso Mater 151:126–133 Zhang F, Yan Y, Yang H, Meng Y, Yu C, Tu B, Zhao D (2005) Understanding effect of wall structure on the hydrothermal stability of mesostructured silica SBA-15. J Phys Chem B 109:8723–8732 Mile B, Steriling D, Zammitt MA (1990) TPR studies of the effects of preparation conditions on supported nickel catalysts. J Mol Catal 62:179–198 Wu T, Yan Q, Wan H (2005) Partial oxidation of methane to hydrogen and carbon monoxide over a Ni/TiO2 catalyst. J Mol Catal A: Chem 226:41–48 Diskin AM, Cunningham RH, Ormerod RM (1998) The oxidative chemistry of methane over supported nickel catalysts. Catal Today 46(2/3):147–155 Mohan V, Raju BD, Rao KSR (2015) Vapour phase hydrogenation of levulinic acid over carbon coated HZSM-5 supported Ni catalysts. J Catal Catal 2(2):33–38 Mohan V, Venkateshwarlu V, Pramod CV, Raju BD, Rao KSR (2014) Vapour phase hydrocyclisation of levulinic acid to γ-valerolactone over supported Ni catalysts. Catal Sci Technol 4:1253–1259 Varkolu M, Velpula V, Ganji S, Burri DR, Kamaraju SRR (2015) Ni nanoparticles supported on mesoporous silica (2D, 3D) architectures: highly efficient catalysts for the hydrocyclization of biomassderived levulinic acid. RSC Adv 5:57201–57210 Mohan V, Pramod CV, Suresh M, Hari KHP, Raju BD, Rao KSR (2012) Advantage of Ni/SBA-15 catalyst over Ni/MgO catalyst in terms of catalyst stability due to release of water during nitrobenzene hydrogenation to aniline. Catal Commun 18:89–92 Varkolu M, Velpula V, Burri DR, Kamaraju SRR (2016) Gas phase hydrogenation of levulinic acid to ɣ-valerolactone over supported Ni catalysts with formic acid as hydrogen source. New J Chem 40:3261–3267 Varkolu M, Burri DR, Kamaraju SRR, Jonnalagadda SB, van Zyl WE (2017) Hydrogenation of levulinic acid using formic acid as a hydrogen source over Ni/SiO2 catalysts. Chem Eng Technol 40:719–726