Advertisement

Hydrothermal Solubilization–Hydrolysis–Dehydration of Cellulose to Glucose and 5-Hydroxymethylfurfural Over Solid Acid Carbon Catalysts

  • Nikolay V. Gromov
  • Tatiana B. Medvedeva
  • Oxana P. Taran
  • Andrey V. Bukhtiyarov
  • Cyril Aymonier
  • Igor P. Prosvirin
  • Valentin N. Parmon
Original Paper
  • 45 Downloads

Abstract

Solid acid catalysts based on graphite-like mesoporous carbon material Sibunit were developed for the one-pot solubilization–hydrolysis–dehydration of cellulose into glucose and 5-hydroxymethylfurfural (5-HMF). The catalysts were produced by treating Sibunit surface with three different procedures to form acidic and sulfo groups on the catalyst surface. The techniques used were: (1) sulfonation by H2SO4 at 80–250 °C, (2) oxidation by wet air or 32 v/v% solution of HNO3, and (3) oxidation-sulfonation what meant additional sulfonating all the oxidized carbons at 200 °C. All the catalysts were characterized by low-temperature N2 adsorption, titration with NaOH, TEM, XPS. Sulfonation of Sibunit was shown to be accompanied by surface oxidation (formation of acidic groups) and the high amount of acidic groups prevented additional sulfonation of the surface. All the Sibunit treatment methods increased the surface acidity in 3–15 times up to 0.14–0.62 mmol g−1 compared to pure carbon (0.042 mmol g−1). The catalysts were tested in the depolymerization of mechanically activated microcrystalline cellulose at 180 °C in pure water. The main products 5-HMF and glucose were produced with the yields in the range of 8–22 wt% and 12–46 wt%, respectively. The maximal yield were achieved over Sibunit sulfonated at 200 °C. An essential difference in the composition of main products obtained with solid acid Sibunit carbon catalysts (glucose, 5-HMF) and soluble in water H2SO4 catalysts (formic and levulinic acids) as well as strong dependence of the reaction kinetics on the morphology of carbon catalysts argue for heterogenious mechanism of cellulose depolymerization over Sibunit.

Keywords

Solubilization–hydrolysis–dehydration Cellulose Glucose 5-Hydroxymethylfurfural Carbon Sibunit 

Notes

Acknowledgements

This work was supported by the Russian Foundation for Basic Research (Project 17-53-16027) and Russian–French GDRI “Biomass”.

References

  1. 1.
    Bhaumik P, Dhepe PL (2016) Solid acid catalyzed synthesis of furans from carbohydrates. Catal Rev 58:36–112CrossRefGoogle Scholar
  2. 2.
    Murzin D, Salmi T (2012) Catalysis for lignocellulosic biomass processing: methodological aspects. Catal Lett 142:676–689CrossRefGoogle Scholar
  3. 3.
    van de Vyver S, Geboers J, Jacobs PA, Sels BF (2011) Recent advances in the catalytic conversion of cellulose. ChemCatChem 3:82–94CrossRefGoogle Scholar
  4. 4.
    van Putten R-J, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG (2013) Hydroxymethylfurfural, A versatile platform chemical made from renewable resources. Chem Rev 113:1499–1597CrossRefGoogle Scholar
  5. 5.
    Besson M, Gallezot P, Pinel C (2014) Conversion of biomass into chemicals over metal catalysts. Chem Rev 114:1827–1870CrossRefPubMedCentralGoogle Scholar
  6. 6.
    Gallezot P (2012) Conversion of biomass to selected chemical products. Chem Soc Rev 41:1538–1558CrossRefGoogle Scholar
  7. 7.
    Mukherjee A, Dumont M-J, Raghavan V (2015) Review: sustainable production of hydroxymethylfurfural and levulinic acid: challenges and opportunities. Biomass Bioenergy 72:143–183CrossRefGoogle Scholar
  8. 8.
    Wataniyakul P, Boonnoun P, Quitain AT, Sasaki M, Kida T, Laosiripojana N, Shotipruk A (2018) Preparation of hydrothermal carbon as catalyst support for conversion of biomass to 5-hydroxymethylfurfural. Catal Commun 104:41–47CrossRefGoogle Scholar
  9. 9.
    Howard J, Rackemann DW, Bartley JP, Samori C, Doherty WOS (2018) Conversion of sugar cane molasses to 5-hydroxymethylfurfural using molasses and bagasse-derived catalysts. ACS Sustain Chem Eng 6:4531–4538CrossRefGoogle Scholar
  10. 10.
    Delidovich I, Leonhard K, Palkovits R (2014) Cellulose and hemicellulose valorisation: an integrated challenge of catalysis and reaction engineering. Energy Environ Sci 7:2803–2830CrossRefGoogle Scholar
  11. 11.
    Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM (2011) 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754–793CrossRefGoogle Scholar
  12. 12.
    Chheda JN, Huber GW, Dumesic JA (2007) Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angew Chem Int Ed 46:7164–7183CrossRefGoogle Scholar
  13. 13.
    Alonso DM, Bond JQ, Dumesic JA (2010) Catalytic conversion of biomass to biofuels. Green Chem 12:1493–1513CrossRefGoogle Scholar
  14. 14.
    Cao L, Yu IKM, Chen SS, Tsang DCW, Wang L, Xiong X, Zhang S, Ok YS, Kwon EE, Song H, Poon CS (2018) Production of 5-hydroxymethylfurfural from starch-rich food waste catalyzed by sulfonated biochar. Bioresour Technol 252:76–82CrossRefPubMedCentralGoogle Scholar
  15. 15.
    Pagán-Torres YJ, Wang T, Gallo JMR, Shanks BH, Dumesic JA (2012) Production of 5-hydroxymethylfurfural from glucose using a combination of lewis and brønsted acid catalysts in water in a biphasic reactor with an alkylphenol. Solvent ACS Catal 2:930–934CrossRefGoogle Scholar
  16. 16.
    Flèche G (1982) Process for manufacturing 5-hydroxymethylfurfural. USA Patent 4339387Google Scholar
  17. 17.
    Sasaki M, Fang Z, Fukushima Y, Adschiri T, Arai K (2000) Dissolution and hydrolysis of cellulose in subcritical and supercritical water. Ind Eng Chem Res 39:2883–2890CrossRefGoogle Scholar
  18. 18.
    Zhang YP, Lynd LR (2004) Toward an aggregated understanding of enzymatic hydrolysis of cellulose: noncomplexed cellulase systems. Biotechnol Bioeng 88:797–824CrossRefGoogle Scholar
  19. 19.
    Zhao Y, Lu WJ, Wang HT (2009) Supercritical hydrolysis of cellulose for oligosaccharide production in combined technology. Chem Eng J 150:411–417CrossRefGoogle Scholar
  20. 20.
    Perez S, Mazeau K (2005) Conformation, structures, and morfologies of celluloses. In: Dimitriu S (ed) Polysaccharides. Structural diversity and functional versatility, 2 edn. Marcel Dekker, New York, pp 41–64Google Scholar
  21. 21.
    Zhang ZC (2013) Chap. 3 - Emerging catalysis for 5-HMF formation from cellulosic carbohydrates. In: Suib SL (ed) New and future developments in catalysis. Elsevier, Amsterdam, pp 53–71.  https://doi.org/10.1016/B978-0-444-53878-9.00003-5 CrossRefGoogle Scholar
  22. 22.
    Zakrzewska ME, Bogel-Lukasik E, Bogel-Lukasik R (2011) Ionic liquid-mediated formation of 5-hydroxymethylfurfural: a promising biomass-derived building block. Chem Rev 111:397–417CrossRefPubMedCentralGoogle Scholar
  23. 23.
    Zheng Y, Zhao J, Xu F, Li Y (2014) Pretreatment of lignocellulosic biomass for enhanced biogas production. Prog Energy Combust Sci 42:35–53CrossRefGoogle Scholar
  24. 24.
    Gromov NV, Taran OP, Sorokina KN, Mischenko TI, Sivakumar U, Parmon VN (2016) New methods for the one-pot processing of polysaccharide components (cellulose and hemicelluloses) of lignocellulose biomass into valuable products. Part 1: methods for biomass activation. Catal Ind 8:176–786CrossRefGoogle Scholar
  25. 25.
    Yu Y, Lou X, Wu H (2008) Some recent advances in hydrolysis of biomass in hot-compressed water and its comparisons with other hydrolysis methods. Energy Fuel 22:46–60CrossRefGoogle Scholar
  26. 26.
    Bobleter O (2005) Hydrothermal degradation and fractionation of saccharides. In: Dimitriu S (ed) Polysaccharides. Structural diversity and functional versatility, 2 edn. Marcel Dekker, New York, pp 893–913Google Scholar
  27. 27.
    Su J, Qiu M, Shen F, Qi X (2018) Efficient hydrolysis of cellulose to glucose in water by agricultural residue-derived solid acid catalyst. Cellulose 25:17–22CrossRefGoogle Scholar
  28. 28.
    Kim JS, Lee YY, Kim TH (2016) A review on alkaline pretreatment technology for bioconversion of lignocellulosic biomass. Bioresour Technol 199:42–48CrossRefGoogle Scholar
  29. 29.
    Mosier N, Wyman C, Dale B, Elander R, Lee YY, Holtzapple M, Ladisch M (2005) Features of promising technologies for pretreatment of lignocellulosic biomass. Bioresour Technol 96:673–686CrossRefGoogle Scholar
  30. 30.
    Singh R, Shukla A, Tiwari S, Srivastava M (2014) A review on delignification of lignocellulosic biomass for enhancement of ethanol production potential. Renew Sustain Energy Rev 32:713–728CrossRefGoogle Scholar
  31. 31.
    Murzin DY, Murzina EV, Tokarev A, Shcherban ND, Wärnå J, Salmi T (2015) Arabinogalactan hydrolysis and hydrolytic hydrogenation using functionalized carbon materials. Catal Today 2:169–176Google Scholar
  32. 32.
    Kim K-H, Ihm S-K (2011) Heterogeneous catalytic wet air oxidation of refractory organic pollutants in industrial wastewaters: a review. J Hazard Mater 186:16–34CrossRefPubMedCentralGoogle Scholar
  33. 33.
    Levec J, Pintar A (2007) Catalytic wet-air oxidation processes: a review. Catal Today 124:172–184CrossRefGoogle Scholar
  34. 34.
    Nakajima K, Okamura M, Kondo JN, Domen K, Tatsumi T, Hayashi S, Hara M (2008) Amorphous carbon bearing sulfonic acid groups in mesoporous silica as a selective catalyst. Chem Mater 21:186–193CrossRefGoogle Scholar
  35. 35.
    Nakajima K, Hara M (2012) Amorphous carbon with SO3H groups as a solid brensted acid catalyst. ACS Catal 2:1296–1304CrossRefGoogle Scholar
  36. 36.
    Liu X-Y, Huang M, Ma H-L, Zhang Z-Q, Gao J-M, Zhu Y-L, Han X-J, Guo X-Y (2010) Preparation of a carbon-based solid acid catalyst by sulfonating activated carbon in a chemical reduction process. Mol J 15:7188–7196CrossRefGoogle Scholar
  37. 37.
    Bhatnagar A, Hogland W, Marques M, Sillanpaa M (2013) An overview of the modification methods of activated carbon for its water treatment applications. Chem Eng J 219:499–511CrossRefGoogle Scholar
  38. 38.
    Burgess R, Buono C, Davies PR, Davies RJ, Legge T, Lai A, Lewis R, Morgan DJ, Robinson N, Willock DJ (2015) The functionalisation of graphite surfaces with nitric acid: identification of functional groups and their effects on gold deposition. J Catal 323:10–18CrossRefGoogle Scholar
  39. 39.
    Taran OP, Polyanskaya EM, Ogorodnikova OL, Descorme C, Besson M, Parmon VN (2011) Sibunit-based catalytic materials for the deep oxidation of organic ecotoxicants in aqueous solutions. II: wet peroxide oxidation over oxidized carbon catalysts. Catal Ind 3:161–169CrossRefGoogle Scholar
  40. 40.
    Shrotri A, Kobayashi H, Kaiki H, Yabushita M, Fukuoka A (2017) Cellulose hydrolysis using oxidized carbon catalyst in a plug-flow slurry process. Ind Eng Chem Res 56:14471–14478CrossRefGoogle Scholar
  41. 41.
    Taran OP, Descorme C, Polyanskaya EM, Ayusheev AB, Besson M, Parmon VN (2013) Sibunit based catalytic materials for the deep oxidation of organic ecotoxicants in aqueous solutions. III: wet air oxidation of phenol over oxidized carbon and Ru/C catalysts. Catal Ind 5:164–174CrossRefGoogle Scholar
  42. 42.
    Onda A, Ochi T, Yanagisawa K (2008) Selective hydrolysis of cellulose into glucose over solid acid catalysts. Green Chem 10:1033–1037CrossRefGoogle Scholar
  43. 43.
    Onda A, Ochi T, Yanagisawa K (2009) Hydrolysis of cellulose selectively into glucose over sulfonated activated-carbon catalyst under hydrothermal conditions. Top Catal 52:801–807CrossRefGoogle Scholar
  44. 44.
    Pang J, Wang A, Zheng M, Zhang T (2010) Hydrolysis of cellulose into glucose over carbons sulfonated at elevated temperatures. Chem Commun 46:6935–6937CrossRefGoogle Scholar
  45. 45.
    Foo GS, Sievers C (2015) Synergistic effect between defect sites and functional groups on the hydrolysis of cellulose over activated carbon. ChemSusChem 8:534–543CrossRefPubMedCentralGoogle Scholar
  46. 46.
    Guo H, Qi X, Li L, Smith RL Jr (2012) Hydrolysis of cellulose over functionalized glucose-derived carbon catalyst in ionic liquid. Bioresour Technol 116:355–359CrossRefPubMedCentralGoogle Scholar
  47. 47.
    Dora S, Bhaskar T, Singh R, Naik Viswanatha D, Adhikari DK (2012) Effective catalytic conversion of cellulose into high yields of methyl glucosides over sulfonated carbon based catalyst. Bioresour Technol 120:318–321CrossRefPubMedCentralGoogle Scholar
  48. 48.
    Li S, Gu Z, Bjornson BE, Muthukumarappan A (2013) Biochar based solid acid catalyst hydrolyze biomass. J Environ Chem Eng 1:1174–1181CrossRefGoogle Scholar
  49. 49.
    Cao L, Yu IKM, Tsang DCW, Zhang S, Ok YS, Kwon EE, Song H, Poon CS (2018) Phosphoric acid-activated wood biochar for catalytic conversion of starch-rich food waste into glucose and 5-hydroxymethylfurfural. Biores Technol 267:242–248CrossRefGoogle Scholar
  50. 50.
    Liu Z, Fu X, Tang S, Cheng Y, Zhu L, Xing L, Wang J, Xue L (2014) Sulfonated magnetic carbon nanotube arrays as effective solid acid catalysts for the hydrolyses of polysaccharides in crop stalks. Catal Commun 56:1–4CrossRefGoogle Scholar
  51. 51.
    Zhao X, Xu J, Wang A, Zhang T (2015) Porous carbon in catalytic transformation of cellulose. Chin J Catal 36:1419–1427CrossRefGoogle Scholar
  52. 52.
    Guo F, Fang Z, Xu CC, Smith RL Jr (2012) Solid acid mediated hydrolysis of biomass for producing biofuels. Prog Energy Combust Sci 38:672–690CrossRefGoogle Scholar
  53. 53.
    Toda M, Takagaki A, Okamura M, Kondo JN, Hayashi S, Domen K, Hara M (2005) Green chemistry: biodiesel made with sugar catalyst. Nature 438:178–178CrossRefPubMedCentralGoogle Scholar
  54. 54.
    Suganuma S, Nakajima K, Kitano M, Yamaguchi D, Kato H, Hayashi S, Hara M (2008) Hydrolysis of cellulose by amorphous carbon bearing SO3H, COOH, and OH groups. J Am Chem Soc 130:12787–12793CrossRefPubMedCentralGoogle Scholar
  55. 55.
    Shen S, Wang C, Han Y, Cai B, Li H (2014) Influence of reaction conditions on heterogeneous hydrolysis of cellulose over phenolic residue-derived solid acid. Fuel 134:573–578CrossRefGoogle Scholar
  56. 56.
    Li Y, Shen S, Wang C, Peng X, Yuan S (2018) The effect of difference in chemical composition between cellulose and lignin on carbon based solid acids applied for cellulose hydrolysis. Cellulose 25:1851–1863CrossRefGoogle Scholar
  57. 57.
    Fukuhara K, Nakajima K, Kitano M, Kato H, Hayashi S, Hara M (2011) Structure and catalysis of cellulose-derived amorphous carbon bearing SO3H groups. ChemSusChem 4:778–784CrossRefPubMedCentralGoogle Scholar
  58. 58.
    Suganuma S, Nakajima K, Kitano M, Yamaguchi D, Kato H, Hayashi S, Hara M (2010) Synthesis and acid catalysis of cellulose-derived carbon-based solid acid. Solid State Sci 12:1029–1034CrossRefGoogle Scholar
  59. 59.
    Kitano M, Yamaguchi D, Suganuma S, Nakajima K, Kato H, Hayashi S, Hara M (2009) Adsorption-enhanced hydrolysis of ОІ-1,4-glucan on graphene-based amorphous carbon bearing SO3H, COOH, and OH groups. Langmuir 25:5068–5075CrossRefPubMedCentralGoogle Scholar
  60. 60.
    Xiong X, Yu IKM, Chen SS, Tsang DCW, Cao L, Song H, Kwon EE, Ok YS, Zhang S, Poon CS (2018) Sulfonated biochar as acid catalyst for sugar hydrolysis and dehydration. Catal Today 314:52–61CrossRefGoogle Scholar
  61. 61.
    Van Pelt AH, Simakova OA, Schimming SM, Ewbank JL, Foo GS, Pidko EA, Hensen EJM, Sievers C (2014) Stability of functionalized activated carbon in hot liquid water. Carbon 77:143–154CrossRefGoogle Scholar
  62. 62.
    Taran OP, Polyanskaya EM, Ogorodnikova OL, Descorme C, Besson M, Parmon VN (2011) Sibunit-based catalytic materials for the deep oxidation of organic ecotoxicants in aqueous solution: I. Surface properties of the oxidized sibunit samples. Catal Ind 2:381–386CrossRefGoogle Scholar
  63. 63.
    Yabushita M, Kobayashi H, Hasegawa JY, Hara K, Fukuoka A (2014) Entropically favored adsorption of cellulosic molecules onto carbon materials through hydrophobic functionalities. ChemSusChem 7:1443–1450CrossRefPubMedCentralGoogle Scholar
  64. 64.
    Surovikin VF, Plaxin GV, Likholobov VA, Tiunova LJ (1990) Porous carbonaceous material. USA Patent 4978649Google Scholar
  65. 65.
    Likholobov VA (2001) Catalysis by unique metal ion structures in solid matrices from science to application. In: Centi G, Wichterlová B, Bell AT (eds) NATO science series. II. Mathematics, physics and chemistry. V. 13. Kluwer Academic Publishers, Netherlands, pp 295–306Google Scholar
  66. 66.
    Gromov NV, Taran OP, Semeykina VS, Danilova IG, Pestunov AV, Parkhomchuk EV, Parmon VN (2017) Solid acidic NbOx/ZrO2 catalysts for transformation of cellulose to glucose and 5-hydroxymethylfurfural in pure hot water. Catal Lett 147:1485–1495CrossRefGoogle Scholar
  67. 67.
    Pestunov AV, Kuzmin AO, Yatsenko DA, Pravdina MK, Taran OP (2015) The mechanical activation of crystal and wooden sawdust cellulose in various fine-grinding mills. J Siberian Fed Univ Chem 8:386–400CrossRefGoogle Scholar
  68. 68.
    Boehm HP (1966) Chemical identification of surface groups. Adv Catal 16:179–274Google Scholar
  69. 69.
    Toles CA, Marshall WE, Johns MM (1997) Granular activated carbons from nutshells for the uptake of metals organic compounds. Carbon 35:1407–1414CrossRefGoogle Scholar
  70. 70.
    Park S, Baker J, Himmel M, Parilla P, Johnson D (2010) Cellulose crystallinity index: measurement techniques and their impact on interpreting cellulase performance. Biotechnol Biofuels 3:10CrossRefPubMedCentralGoogle Scholar
  71. 71.
    Likholobov VA (2001) Catalysis by novel carbon-based materials. In: Centi G, Wichterlová B, Bell AT (eds) Catalysis by unique metal ion structures in solid matrices from science to application, vol 13. NATO science series. II. Mathematics, Physics. Kluwer Academic Publishers, Netherlands, pp 295–306Google Scholar
  72. 72.
    Shitova NB, Dobrynkin NM, Noskov AS, Prosvirin IP, Bukhtiyarov VI, Kochubei DI, Tsyrul’nikov PG, Shlyapin DA (2004) Formation of Ru–M/Sibunit catalysts for ammonia synthesis. Kinet Catal 45:414–421CrossRefGoogle Scholar
  73. 73.
    Rodríguez-Castellón E, Jiménez-López A, Eliche-Quesada D (2008) Nickel and cobalt promoted tungsten and molybdenum sulfide mesoporous catalysts for hydrodesulfurization. Fuel 87:1195–1206CrossRefGoogle Scholar
  74. 74.
    Zhuang SX, Yamazaki M, Omata K, Takahashi Y, Yamada M (2001) Catalytic conversion of CO, NO and SO2 on supported sulfide catalysts: II. Catalytic reduction of NO and SO2 by CO. Appl Catal B 31:133–143CrossRefGoogle Scholar
  75. 75.
    Sanders AFH, de Jong AM, de Beer VHJ, van Veen JAR, Niemantsverdriet JW (1999) Formation of cobalt–molybdenum sulfides in hydrotreating catalysts: a surface science approach. Appl Surf Sci 144–145:380–384CrossRefGoogle Scholar
  76. 76.
    Okamoto Y, Imanaka T (1988) Interaction chemistry between molybdena and alumina: infrared studies of surface hydroxyl groups and adsorbed carbon dioxide on aluminas modified with molybdate, sulfate, or fluorine anions. J Phys Chem 92:7102–7112CrossRefGoogle Scholar
  77. 77.
    Hibbert DB, Campbell RH (1988) Flue gas desulphurisation: catalytic removal of sulphur dioxide by carbon monoxide on sulphided La1 – xSrxCoO3. II. Reaction of sulphur dioxide and carbon monoxide in a flow system. Appl Catal 41:289–299CrossRefGoogle Scholar
  78. 78.
    Janaun J, Ellis N (2011) Role of silica template in the preparation of sulfonated mesoporous carbon catalysts. Appl Catal A 394:25–31CrossRefGoogle Scholar
  79. 79.
    Takagaki A, Toda M, Okamura M, Kondo JN, Hayashi S, Domen K, Hara M (2006) Esterification of higher fatty acids by a novel strong solid acid. Catal Today 116:157–161CrossRefGoogle Scholar
  80. 80.
    Moulder JF, Stickle WF, Sobol PE, Bomben KD (1992) Handbook of X-ray photoelectron spectroscopy. Physical Electronics Division, Perkin-Elmer Corporation, Eden PrairieGoogle Scholar
  81. 81.
    Zemlyanov DY, Nagy A, Schlögl R (1998) The reaction of silver with NO/O2. Appl Surf Sci 133:171–183CrossRefGoogle Scholar
  82. 82.
    Motoyuki S (1993) Studies in surface science and catalysis. In: Fundamentals of adsorption, vol 80. Elsevier, AmsterdamGoogle Scholar
  83. 83.
    Scofield JH (1976) Hartree-Slater subshell photoionization cross-sections at 1254 and 1487 eV. J Electron Spectrosc Relat Phenom 8:129–137CrossRefGoogle Scholar
  84. 84.
    Morrison RT, Boyd RN (1977) Organic chemistry, 2nd edn. Allyn and Bacon Inc., BostonGoogle Scholar
  85. 85.
    Gromov NV, Taran OP, Delidovich IV, Pestunov AV, Rodikova YA, Yatsenko DA, Zhizhina EG, Parmon VN (2016) Hydrolytic oxidation of cellulose to formic acid in the presence of Mo-V-P heteropoly acid catalysts. Catal Today 278:74–81CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Nikolay V. Gromov
    • 1
    • 2
  • Tatiana B. Medvedeva
    • 1
  • Oxana P. Taran
    • 1
    • 3
  • Andrey V. Bukhtiyarov
    • 1
    • 4
  • Cyril Aymonier
    • 5
  • Igor P. Prosvirin
    • 1
    • 4
  • Valentin N. Parmon
    • 1
    • 4
  1. 1.Boreskov Institute of Catalysis SB RASNovosibirskRussia
  2. 2.Novosibirsk State Technical UniversityNovosibirskRussia
  3. 3.Institute of Chemistry and Chemical Technology SB RASFRC Krasnoyarsk Science Center SB RASKrasnoyarskRussia
  4. 4.Novosibirsk National Research State UniversityNovosibirskRussia
  5. 5.Institut de Chimie de la Matière Condensée de BordeauxCNRS, Universite de BordeauxPessacFrance

Personalised recommendations