Citation: Si-chan LI, Yu-long DENG, Hai-yong WANG, Chen-guang WANG, Long-long MA, Qi-ying LIU. Production of acetol and lactic acid from cellulose hydrogenolysis over Sn-Fe@C catalysts[J]. Journal of Fuel Chemistry and Technology, ;2022, 50(3): 314-325. doi: 10.1016/S1872-5813(21)60153-6 shu

Production of acetol and lactic acid from cellulose hydrogenolysis over Sn-Fe@C catalysts

1.
Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China
2.
Nano Science and Technology Institute, University of Science and Technology of China, Suzhou 215123, China

Corresponding author: Hai-yong WANG, wanghy@ms.giec.ac.cn Qi-ying LIU, liuqy@ms.giec.ac.cn
Received Date: 23 July 2021
Revised Date: 25 August 2021

Figures(11)

Acetol and lactic acid are valuable platform chemicals that have a broad range of industrial applications and their production from renewable cellulose is of scientific and practical significance. A series of Sn-Fe@C catalysts were prepared by sol-gel and high-temperature annealing method in an inert atmosphere and then used for preparing acetol and lactic acid by one-step hydrogenolysis of cellulose in aqueous system. 3Sn1Fe@C₆₀₀ as catalyst, the total acetol and lactic acid yield of 45.4% were obtained at 240 ℃ for 1 h under H₂ atmosphere, of which the yields of acetol and lactic acid were 24.3% and 21.1%, respectively. The results indicated that the yield of acetol and lactic acid was strongly dependent on the Sn/Fe ratio of the catalyst as well as the annealing temperature. The characterizations including BET, XRD, XPS, Py-FTIR and CO₂-TPD were carried out to explore the relationship between the structure of catalysts and catalytic activity. The strong L acid sites, basic sites and the metal active sites of the catalyst were the key factors affecting the selective production of acetol and lactic acid from cellulose hydrogenolysis.
- biomass,
- hydrogenolysis,
- acetol,
- lactic acid,
- catalysis
1. [1]
  LI Chang-zhi, WANG Ai-qin, ZHANG Tao. Progress of conversion of cellulose resource in ionic liquids[J]. CIESC J,2013,64(1):182−197. doi: 10.3969/j.issn.0438-1157.2013.01.021
2. [2]
  YAN Li-feng, ZHU Qing-shi. New chemical industry based on biomass[J]. CIESC J,2004,(12):1938−1943. doi: 10.3321/j.issn:0438-1157.2004.12.002
3. [3]
  GUO Xiao, YAN Ya-ni, ZHANG Ya-hong, TANG Yi. Heterogeneously catalytic transformation of biomass-derived sugars[J]. Prog Chem,2013,25(11):1915−1927.
4. [4]
  LAZARIDIS P A, KARAKOULIA S A, TEODORESCU C, APOSTOL N, MACOVEI D, PANTELI A, DELIMITIS A, COMAN S M, PARVULESCU V I, TRIANTAFYLLIDIS K S. High hexitols selectivity in cellulose hydrolytic hydrogenation over platinum (Pt) vs. ruthenium (Ru) catalysts supported on micro/mesoporous carbon[J]. Appl Catal B: Environ,2017,214:1−14. doi: 10.1016/j.apcatb.2017.05.031
5. [5]
  GAO L F, BAO Y, GAN S Y, SUN Z H, SONG Z Q, HAN D X, LI F H, NIU L. Hierarchical nickel-cobalt-based transition metal oxide catalysts for the electrochemical conversion of biomass into valuable chemicals[J]. ChemSusChem,2018,11(15):2547−2553. doi: 10.1002/cssc.201800695
6. [6]
  KESKIVALI J, RAUTIAINEN S, HEIKKILA M, MYLLYMAKI TTT, KARJALAINEN J P, LAGERBLOM K, KEMELL M, VEHKAMAKI M, MEINANDER K, REPO T. Isosorbide synthesis from cellulose with an efficient and recyclable ruthenium catalyst[J]. Green Chem,2017,19(19):4563−4570. doi: 10.1039/C7GC01821E
7. [7]
  SATO S, SAKAI D, SATO F, YAMADA Y. Vapor-phase dehydration of glycerol into hydroxyacetone over silver catalyst[J]. Chem Lett,2012,41(9):965−966. doi: 10.1246/cl.2012.965
8. [8]
  HOYOS P, SINISTERRA J V, MOLINARI F, ALCANTARA A R, DE MARIA P D. Biocatalytic strategies for the asymmetric synthesis of alpha-hydroxy ketones[J]. Accounts Chem Res,2010,43(2):288−299. doi: 10.1021/ar900196n
9. [9]
  MOHAMAD. A review of acetol: Application and production[J]. Am J Appl Sci,2011,8:1135−1139. doi: 10.3844/ajassp.2011.1135.1139
10. [10]
  DENG T Y, LIU H C. Direct conversion of cellulose into acetol on bimetallic Ni-SnO_x/Al₂O₃ catalysts[J]. J Mol Catal A: Chem,2014,388:66−73.
11. [11]
  WANG H Y, ZHU C H, LIU Q Y, TAN J, WANG C G, LIANG Z, MA L L. Selective conversion of cellulose to hydroxyacetone and 1-hydroxy-2-butanone with Sn-Ni bimetallic catalysts[J]. ChemSusChem,2019,12(10):2154−2160. doi: 10.1002/cssc.201900172
12. [12]
  LIU X H, LIU X D, XU G Y, ZHANG Y, WANG C G, LU Q, MA L L. Highly efficient catalytic conversion of cellulose into acetol over Ni-Sn supported on nanosilica and the mechanism study[J]. Green Chem,2019,21(20):5647−5656. doi: 10.1039/C9GC02449B
13. [13]
  WANG Yong, ZOU Xian-wu, QIN Te-fu. Research progress on technologies of biomass conversion and upgrading of bio-oil[J]. Chem Bioeng,2010,27(9):1−5. doi: 10.3969/j.issn.1672-5425.2010.09.001
14. [14]
  DATTA R, HENRY M. Lactic acid: Recent advances in products, processes and technologies - a review[J]. J Chem Technol Biotechnol,2006,81(7):1119−1129. doi: 10.1002/jctb.1486
15. [15]
  RIZESCU C, PODOLEAN I, COJOCARU B, PARVULESCU V I, COMAN S M, ALBERO J, GARCIA H. RuCl₃ supported on n-doped graphene as a reusable catalyst for the one-step glucose oxidation to succinic Acid[J]. ChemCatChem,2017,9(17):3314−3321. doi: 10.1002/cctc.201700383
16. [16]
  ZENG Wei, CHEN Feng-qiu, ZHAN Xiao-li. Advances in production technology of lactic acid[J]. Chem Ind Eng Prog,2006,18(7):744−749. doi: 10.3321/j.issn:1000-6613.2006.07.005
17. [17]
  DENG W P, WANG P, WANG B J, WANG Y L, YAN L F, LI Y Y, ZHANG Q H, CAO Z X, WANG Y. Transformation of cellulose and related carbohydrates into lactic acid with bifunctional Al(III)-Sn(II) catalysts[J]. Green Chem,2018,20(3):735−744. doi: 10.1039/C7GC02975F
18. [18]
  LI L Y, SHEN F, SMITH R L, QI X H. Quantitative chemocatalytic production of lactic acid from glucose under anaerobic conditions at room temperature[J]. Green Chem,2017,19(1):76−81. doi: 10.1039/C6GC02443B
19. [19]
  LEI X, WANG F F, LIU C L, YANG R Z, DONG W S. One-pot catalytic conversion of carbohydrate biomass to lactic acid using an ErCl3 catalyst[J]. Appl Catal A: Gen,2014,482:78−83. doi: 10.1016/j.apcata.2014.05.029
20. [20]
  ZHANG S P, JIN F M, HU J J, HUO Z B. Improvement of lactic acid production from cellulose with the addition of Zn/Ni/C under alkaline hydrothermal conditions[J]. Bioresour Technol,2011,102(2):1998−2003. doi: 10.1016/j.biortech.2010.09.049
21. [21]
  WANG Y L, DENG W P, WANG B J, ZHANG Q H, WAN X Y, TANG Z C, WANG Y, ZHU C, CAO Z X, WANG G C, WAN H L. Chemical synthesis of lactic acid from cellulose catalysed by lead(II) ions in water[J]. Nat Commun,2013,4:2141.
22. [22]
  SING K S W, EVERETT D H, HAUL R A W, MOSCOU L, PIEROTTI R A, ROUQUEROL J, SIEMIENIEWSKA T. Reporting physisorption data for gas solid systems with special reference to the determination of surface-area and porosity (recommendations 1984)[J]. Pure Appl Chem,1985,57(4):603−619. doi: 10.1351/pac198557040603
23. [23]
  LAU C L, WERTHEIM G K. Oxidation of tin - esca study[J]. J Vac Sci Technol,1978,15(2):622−624. doi: 10.1116/1.569642
24. [24]
  ZENG J, PENG C Q, WANG R C, CAO C Y, WANG X F, LIU J. Magnetic Sn/SnO/FeSn₂ nanocomposite as a high-performance anode material for lithium-ion batteries[J]. Powder Technol,2020,364:719−724. doi: 10.1016/j.powtec.2020.01.057
25. [25]
  HU C Q, GAO Z H, YANG X R. Fabrication and magnetic properties of Fe₃O₄ octahedra[J]. Chem Phys Lett,2006,429(4/6):513−517. doi: 10.1016/j.cplett.2006.08.041
26. [26]
  YAMASHITA T, HAYES P. Analysis of XPS spectra of Fe²⁺ and Fe³⁺ ions in oxide materials[J]. Appl Surf Sci,2008,254(8):2441−2449. doi: 10.1016/j.apsusc.2007.09.063
27. [27]
  EMEIS C A. Determination of integrated molar extinction coefficients for infrared-absorption bands of pyridine adsorbed on solid acid catalysts[J]. J Catal,1993,141(2):347−54. doi: 10.1006/jcat.1993.1145
28. [28]
  WANG H Y, XIN H S, CAI C L, ZHU C H, XIU Z X, LIU Q Y, WENG Y J, WANG C G, ZHANG X H, LIU S J, PENG Z F, MA L L. Selective C-3-C-4 keto-alcohol production from cellulose hydrogenolysis over Ni-WOx/C catalysts[J]. ACS Catal,2020,10(18):10646−10660. doi: 10.1021/acscatal.0c02375
29. [29]
  XIU Z X, WANG H Y, CAI C L, LI C Z, YAN L, WANG C G, LI W Z, XIN H S, ZHU C H, ZHANG Q, LIU Q Y, MA L L. Ultrafast glycerol conversion to lactic acid over magnetically recoverable Ni-NiOx@C catalysts[J]. Ind Eng Chem Res,2020,59(21):9912−9925. doi: 10.1021/acs.iecr.0c01145
30. [30]
  KISHIDA H, JIN F M, ZHOU Z Y, MORIYA T, ENOMOTO H. Conversion of glycerin into lactic acid by alkaline hydrothermal reaction[J]. Chem Lett,2005,34(11):1560−1561. doi: 10.1246/cl.2005.1560
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沈阳化工大学材料科学与工程学院沈阳 110142