Гидрирование продуктов переработки полисахаридов биомассы, содержащих фурановый фрагмент, на палладиевом катализаторе на основе мезопористого алюмосиликата

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Abstract

Синтезирован катализатор на основе мезопористого алюмосиликата Al-MCM-41, содержащий наночастицы палладия. Катализатор исследован в жидкофазном гидрировании фурфурола, 5-гидроксиметилфурфурола и фурфурилового спирта при начальном давлении водорода 5 МПа. Изучено влияние времени реакции, концентрации катализатора, температуры и природы растворителя на конверсию и распределение продуктов гидрирования фурфурола. Установлено, что в водной среде в присутствии Pd/Al-MCM-41 фурфурол превращается преимущественно в тетрагидрофурфуриловый спирт в мягких условиях (100°С, 45 мин) при полной конверсии субстрата. Показано влияние структуры продуктов переработки полисахаридов биомассы, содержащих фурановый фрагмент, на конверсию и селективность процесса гидрирования на катализаторе Pd/Al-MCM-41 в водной среде.

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About the authors

Екатерина Алексеевна Ролдугина

Московский государственный университет им. М. В. Ломоносова

Author for correspondence.
Email: rolduginakate@mail.ru
ORCID iD: 0000-0002-9194-1097

химический факультет, к.х.н.

Russian Federation, 119991, ГСП-1, г. Москва, Ленинские горы, д. 1, стр. 3

Анастасия Алексеевна Ситникова

Московский государственный университет им. М. В. Ломоносова

Email: rolduginakate@mail.ru
ORCID iD: 0009-0009-1429-3477

химический факультет

Russian Federation, 119991, ГСП-1, г. Москва, Ленинские горы, д. 1, стр. 3

Максим Павлович Бороноев

Московский государственный университет им. М. В. Ломоносова

Email: rolduginakate@mail.ru
ORCID iD: 0000-0001-6129-598X

химический факультет, к.х.н.

Russian Federation, 119991, ГСП-1, г. Москва, Ленинские горы, д. 1, стр. 3

Искандер Ильгизович Шакиров

Московский государственный университет им. М. В. Ломоносова

Email: rolduginakate@mail.ru
ORCID iD: 0000-0003-2029-693X

химический факультет, к.х.н.

Russian Federation, 119991, ГСП-1, г. Москва, Ленинские горы, д. 1, стр. 3

Юлия Сергеевна Кардашева

Московский государственный университет им. М. В. Ломоносова

Email: rolduginakate@mail.ru
ORCID iD: 0000-0002-6580-1082

химический факультет, к.х.н.

Russian Federation, 119991, ГСП-1, г. Москва, Ленинские горы, д. 1, стр. 3

References

  1. Anjali, Sravanthi Veluturla, Saranya R., Vijaya Lakshmi S., Hemanth K. M. Nanoparticles for the synthesis of bio-based chemical 5-hydroxymethyl furfural from agricultural waste and biomass-derived carbohydrates — A review // J. Chem. Technol. Biotechnol. 2024. V. 99. N 7. P. 1477–1492. https://doi.org/10.1002/jctb.7634
  2. Martínez-Edo G., Balmori A., Pontón I., Martí del Rio A., Sánchez-García D. Functionalized ordered mesoporous silicas (MCM-41): Synthesis and applications in catalysis // Catalysts. 2018. V. 8. N 12. ID 617. https://doi.org/10.3390/catal8120617
  3. Climent M. J., Corma A., Iborra S. Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels // Green Chem. 2014. V. 16. P. 516–547. https://doi.org/10.1039/C3GC41492B
  4. Jiménez-Morales I., Moreno-Recio M., Santamaría-González J., Maireles-Torres P., Jiménez-López A. Production of 5-hydroxymethylfurfural from glucose using aluminium doped MCM-41 silica as acid catalyst // Appl. Catal. B. 2015. V. 164. P. 70–76. https://doi.org/10.1016/j.apcatb.2014.09.002
  5. Lima S., Pillinger M., Valente A. A. Dehydration of d-xylose into furfural catalysed by solid acids derived from the layered zeolite Nu-6(1) // Catal. Commun. 2008. V. 9. N 11–12. P. 2144–2148. https://doi.org/10.1016/j.catcom.2008.04.016
  6. Fang W., Riisager A. Recent advances in heterogeneous catalytic transfer hydrogenation/hydrogenolysis for valorization of biomass-derived furanic compounds // Green Chem. 2021. V. 23. P. 670–688. https://doi.org/10.1039/D0GC03931D
  7. Chatterjee M., Matsushima K., Ikushima Y., Sato M., Yokoyama T., Kawanami H., Suzuki T. Production of linear alkane via hydrogenative ring opening of a furfural-derived compound in supercritical carbon dioxide // Green Chem. 2010. V. 12. P. 779–782. https://doi.org/10.1039/B919810P
  8. Li X., Deng Q., Zhou Sh., Zou J., WangJ., Wang R., Zeng Zh., Deng Sh., Deng Sh. Double-metal cyanide-supported Pd catalysts for highly efficient hydrogenative ring-rearrangement of biomass-derived furanic aldehydes to cyclopentanone compounds // J. Catal. 2019. V. 378. P. 201–208. https://doi.org/10.1016/j.jcat.2019.08.036
  9. Suyanta S., Narsito, Wahyuni E. T., Triyono. Synthesis and characterization of mesoporous aluminosilicates Al-MCM-41 and investigation of its thermal, hydrothermal and acidity stability // Indo. J. Chem. 2010. V. 10. N 1. P. 41–45. https://doi.org/10.22146/ijc.21478
  10. Rashwan W. E., Abou-El-Sherbini K. S., Wahba M. A., Sayed Ahmed S. A., Weidler P. G. High stable Al-MCM-41: Structural characterization and evaluation for removal of methylene blue from aqueous solution. Silicon // 2019. V. 12. N 9. P. 2017–2029. https://doi.org/10.1007/s12633-019-00262-x
  11. Shaik M., Ali Z., Khan M., Kuniyil M., Assal M., Alkhathlan H., Adil S. Green synthesis and characterization of palladium nanoparticles using Origanum vulgare L. Extract and their catalytic activity // Molecules. 2017. V. 22. N 1. ID 165. https://doi.org/10.3390/molecules22010165
  12. Huirache-Acuña R., Zepeda T. A., Vázquez P. J., Rivera-Muñoz E. M., Maya-Yescas R., Pawelec B., Alonso-Núñez G. The use of inorganic Al-HMS as a support for NiMoW sulfide HDS catalysts // Inorg. Chim. Acta. 2021. V. 524. ID 120450. https://doi.org/10.1016/j.ica.2021.120450
  13. Tsatsos S., Ladas S., Kyriakou G. Electronic properties and reactivity of furfural on a model Pt(111) catalytic surface // J. Phys. Chem. C. 2020. V. 124. N 48. P. 26268–26278. https://doi.org/10.1021/acs.jpcc.0c07709
  14. Tong Z., Li X., Dong J., Gao R., Deng Q., Wang J., Deng S. Adsorption configuration-determined selective hydrogenative ring opening and ring rearrangement of furfural over metal phosphate // ACS Catal. 2021. V. 11. N 11. P. 6406–6415. https://doi.org/10.1021/acscatal.0c05497
  15. Pirmoradi M., Gulotty Jr. R. J., Kastner J. R. Continuous hydroxyketone production from furfural using Pd–TiO2 supported on activated carbon // Catal. Sci. Technol. 2020. V. 10. P. 7002–7015. https://doi.org/10.1039/D0CY01556C
  16. Mironenko R. M., Talsi V. P., Gulyaeva T. I. Aqueous-phase hydrogenation of furfural over supported palladium catalysts: Effect of the support on the reaction routes // React. Kinet. Mech. Catal. 2019. V. 126. P. 811–827. https://doi.org/10.1007/s11144-018-1505-y
  17. Hu X., Kadarwati S., Song Y., Li Z. Simultaneous hydrogenation and acid-catalyzed conversion of the biomass-derived furans in solvents with distinct polarities // RSC Adv. 2016. V. 6. P. 4647–4656. https://doi.org/10.1039/C5RA22414D
  18. Zhao Z., Bababrik R., Xue W., Li Y., Briggs N. M., Nguyen D.-T., Nguyen U., Crossley S. P., Wang S., Wang B., Resasco D. E. Solvent-mediated charge separation drives alternative hydrogenation path of furanics in liquid water // Nat. Catal. 2019. V. 2. P. 431–436. https://doi.org/10.1038/s41929-019-0257-z
  19. Endot N. A., Junid R., Jamil M. Sh. Sh. Insight into biomass upgrade: A review on hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-dimethylfuran (DMF) // Molecules. 2021. V. 26. N 22. ID 6848. https://doi.org/10.3390/molecules26226848
  20. Gong W., Chen C., Zhang Y., Zhou H., Wang H., Zhang H., Zhao H. Efficient synthesis of furfuryl alcohol from H2-hydrogenation/transfer hydrogenation of furfural using sulfonate group modified Cu catalyst // ACS Sustain. Chem. Eng. 2017. V. 5. N 3. P. 2172–2180. https://doi.org/10.1021/acssuschemeng.6b02343
  21. Li J., Xi Y., Qiao Y., Zhao Z., Liu J., Li F. Solvent effects on heterogeneous catalysis for the selective hydrogenation // ChemCatChem. 2024. V. 6. N 14. ID e202400120. https://doi.org/10.1002/cctc.202400120
  22. Chen Sh., Wojcieszak R., Dumeignil F., Marceau E., Royer S. How catalysts and experimental conditions determine the selective hydroconversion of furfural and 5-hydroxymethylfurfural // Chem. Rev. 2018. V. 118. N 22. P. 11023–11117. https://doi.org/10.1021/acs.chemrev.8b00134
  23. Gao X., Tian S., Jin Y., Wan X., Zhou C., Chen R., Yang Y. Bimetallic PtFe-catalyzed selective hydrogenation of furfural to furfuryl alcohol: Solvent effect of isopropanol and hydrogen activation // ACS Sustain. Chem. Eng. 2020. V. 8. P. 12722–12730. https://doi.org/10.1021/acssuschemeng.0c04891
  24. Longo L., Taghavi S., Ghedini E., Menegazzo F., Di Michele A., Cruciani G., Signoretto M. Selective hydrogenation of 5-hydroxymethylfurfural to 1-hydroxy-2,5-hexanedione by biochar-supported Ru catalysts // ChemSusChem. 2022. V. 15. N 13. ID e202200437. https://doi.org/10.1002/cssc.202200437
  25. Dutta S., Bhat N. S. Catalytic transformation of biomass-derived furfurals tocyclopentanones and their derivatives: A review // ACS Omega. 2021. V. 6. N 5. P. 35145–35875. https://doi.org/10.1021/acsomega.1c05861.
  26. Morales M. V., Conesa J. M., Campos-Castellanos E., Guerrero-Ruiz A., Rodríguez-Ramos I. Critical factors affecting the selective transformation of 5-hydroxymethylfurfural to 3-hydroxymethylcyclopentanone over Ni catalysts // ChemSusChem. 2024. V. 17. N 23. ID e202400559. https://doi.org/10.1002/cssc.202400559

Supplementary files

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2. Fig. 1. Ammonia temperature-programmed desorption spectrum (a) and small-angle scattering diffraction pattern (b) of mesoporous aluminosilicate Al-MCM-41.

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3. Fig. 2. Nitrogen adsorption-desorption isotherms and pore size distribution of mesoporous aluminosilicate Al-MCM-41 and Pd-containing catalyst based on it.

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4. Fig. 3. X-ray diffraction pattern (a), micrograph and Pd nanoparticle size distribution diagram (b) of Pd catalyst based on mesoporous aluminosilicate Al-MCM-41.

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5. Fig. 4. Hydrogenation of furfural in the presence of Pd/Al-MCM-41 catalyst at different reaction times (a) and substrate/catalyst weight ratios (b). Reaction conditions: 0.6 mmol furfural, 2 ml water, 5 MPa H2, 100°C, 3 mg Pd/Al-MCM-41 (a), 45 min (b). Other products: 4-oxopentanal, 5-hydroxy-2-pentanone. * 100–200°C, 45 min, 3 mg Al-MCM-41 support.

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6. Fig. 5. Hydrogenation of furfural in the presence of Pd/Al-MCM-41 catalyst in aqueous medium (a) and in toluene (b). Reaction conditions: 0.6 mmol furfural, 3 mg Pd/Al-MCM-41, 5 MPa H2, 30 min, 2 ml water (a), 2 ml toluene (b). Other products: 2-methyltetrahydrofuran, 2-methylfuran, 3-hydroxycyclopentanone (a), C5+ condensation products (b). * 8 mg Pd/Al-MCM-41.

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7. Fig. 6. Hydrogenation of furfuryl alcohol (a) and 5-hydroxymethylfurfural (b) in the presence of Pd/Al-MCM-41 catalyst. Reaction conditions: 0.6 mmol substrate, 2 ml water, 5 MPa H2, 30 min, Pd/Al-MCM-41 — 3 mg (a), 6 mg (b).

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