Recent advances in the selective hydrogenation of furfural and its   derivatives to pentanediol

TAN Jing-jing; SU Yi-hao; GAO Kuan; CUI Jing-lei; WANG Yong-zhao; ZHAO Yong-xiang

doi:10.1016/S1872-5813(21)60036-1

Volume 49 Issue 6

Jun. 2021

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Article Navigation > Journal of Fuel Chemistry and Technology > 2021 > 49(6): 780-790

TAN Jing-jing, SU Yi-hao, GAO Kuan, CUI Jing-lei, WANG Yong-zhao, ZHAO Yong-xiang. Recent advances in the selective hydrogenation of furfural and its derivatives to pentanediol[J]. Journal of Fuel Chemistry and Technology, 2021, 49(6): 780-790. doi: 10.1016/S1872-5813(21)60036-1

Citation:

TAN Jing-jing, SU Yi-hao, GAO Kuan, CUI Jing-lei, WANG Yong-zhao, ZHAO Yong-xiang. Recent advances in the selective hydrogenation of furfural and its derivatives to pentanediol[J]. Journal of Fuel Chemistry and Technology, 2021, 49(6): 780-790. doi: 10.1016/S1872-5813(21)60036-1

Citation:

TAN Jing-jing, SU Yi-hao, GAO Kuan, CUI Jing-lei, WANG Yong-zhao, ZHAO Yong-xiang. Recent advances in the selective hydrogenation of furfural and its derivatives to pentanediol[J]. Journal of Fuel Chemistry and Technology, 2021, 49(6): 780-790. doi: 10.1016/S1872-5813(21)60036-1

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Recent advances in the selective hydrogenation of furfural and its derivatives to pentanediol

doi: 10.1016/S1872-5813(21)60036-1

1.
Engineering Research Center of Ministry of Education for Fine Chemicals, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
2.
Institute of Resources and Environmental Engineering, Shanxi University, Taiyuan 030006, China

Funds: The project was supported by the National Natural Science Foundation of China (22005182, 21703275, U1710221), the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (2020L0012), Shanxi Provincial Natural Science Foundation of China (201701D221030)

Received Date: 2020-12-18
Rev Recd Date: 2021-01-25

Available Online: 2021-03-30

Publish Date: 2021-06-30

Abstract

Abstract

1,2-pentanediol (1,2-PeD) and 1,5-pentanediol (1,5-PeD) are high-value fine chemicals with a wide range of uses. It is a green process with well application prospects and research value for the preparation of 1,2-PeD and 1,5-PeD from furfural and its derivatives. Here, the recent advances of furfural and its derivatives furfuryl alcohol and tetrahydrofurfuryl alcohol in the synthesis of 1,2-PeD and 1,5-PeD were reviewed systematically. We focused on the summary of the catalysts used in the catalytic hydrogenation of furfural, furfuryl alcohol and tetrahydrofurfuryl alcohol to prepare 1,2-PeD and 1,5-PeD. The design and application of the catalysts were elaborated from many aspects, including the catalyst type, the reaction mechanism with assist acid/base in different catalytic systems, the synergistic catalysis between active metals and doped transition metal oxides, the influence of acidity of doped transition metal oxides in the catalyst, the structure-activity relationships and so on. On this basis, the development trend of this research direction is prospected. It provides the theoretical guidance and useful reference for developing a new, efficient and stable catalyst system for the hydrogenation of furfural and its derivatives.
- furfural,
- furfuryl alcohol,
- tetrahydrofurfuryl alcohol,
- catalytic hydrogenation,
- 1,2-pentanediol,
- 1,5-pentanediol

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References(44)

References

[1]	MIZUGAKI T, YAMAKAWA T, NAGATSU Y, MAENO Z, MITSUDOME T, JITSUKAWA K, KANEDA K. Direct transformation of furfural to 1,2-pentanediol using a hydrotalcite-supported platinum nanoparticle catalyst[J]. ACS Sustainable Chem Eng,2014,2(10):2243−2247. doi: 10.1021/sc500325g
[2]	LIU H, HUANG Z W, KANG H X, XIA C G, CHEN J. Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2- and 1,5-pentanediol over highly dispersed Cu-Al₂O₃ catalysts[J]. Chin J Catal,2016,37(5):700−710. doi: 10.1016/S1872-2067(15)61080-4
[3]	SCHLAF M. Selective deoxygenation of sugar polyols to α, ω-diols and other oxygen content reduced materials-a new challenge to homogeneous ionic hydrogenation and hydrogenolysis catalysis[J]. Dalton Trans,2006,39:4645−4653.
[4]	李静. 四氢糠醇在 Rh(111)表面上 C−O 键氢解的密度泛函理论研究[D]. 石家庄: 河北科技大学, 2016. LI Jing. Density functional theory study on hydrogenolysis of C−O bond on Rh(111) surface with tetrahydrofurfuryl alcohol[D]. Shijiazhuang: Hebei University of Science and Technology, 2016.
[5]	BRENTZEL Z J, BARNETT K J, HUANG K, MARAVELIAS P, DUMESIC P, HUBER P. Chemicals from biomass: combining ring-opening tautomerization and hydrogenation reactions to produce 1,5-pentanediol from furfural[J]. ChemSusChem,2017,10(7):1351−1355.
[6]	ZHANG B, ZHU Y, DING G Q, ZHENG H Y, LI Y W. Selective conversion of furfuryl alcohol to 1,2-pentanediol over a Ru/MnO_x catalyst in aqueous phase[J]. Green Chem,2012,14(12):3402−3409.
[7]	IOELOVICH M. Recent findings and the energetic potential of plant biomass as a renewable source of biofuels - a review[J]. Bioresources,2015,10(1):879−1914.
[8]	VAMVUKA D. Bio-oil, solid and gaseous biofuels from biomass pyrolysis processes-An overview[J]. Int J Energy Res,2011,35(10):835−862. doi: 10.1002/er.1804
[9]	RPEREZ R F, FRAGA M A. Hemicellulose-derived chemicals: one-step production of furfuryl alcohol from xylose[J]. Green Chem,2014,16(8):3942−3950. doi: 10.1039/C4GC00398E
[10]	CHIA M, PAGÁN-TORRES Y J, HIBBITTS D, HIBBITTS D, TAN Q H, PHAM H N, DATYE A K, NEUROCK M, DAVIS R J, DUMESIC J A. Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium-rhenium catalysts[J]. J Am Chem Soc,2011,133(32):12675−12689. doi: 10.1021/ja2038358
[11]	GUAN J, PENG G M, CAO Q, MU X D. Role of MoO₃ on a rhodium catalyst in the selective hydrogenolysis of biomass-derived tetrahydrofurfuryl alcohol into 1,5-Pentanediol[J]. J Phys Chem C,2014,118(44):25555−25566. doi: 10.1021/jp508313y
[12]	KOSO S, UEDA N, SHINMI Y, OKUMURA K, KIZUKA T, TOMISHIGE K. Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh/SiO₂[J]. J Catal,2009,267(1):89−92. doi: 10.1016/j.jcat.2009.07.010
[13]	LIU S B, AMADA Y, TAMURA M, NAKAGAWA Y, TOMISHIGE K. Performance and characterization of rhenium-modified Rh-Ir alloy catalyst for one-pot conversion of furfural into 1,5-pentanediol[J]. Catal Sci Technol,2014,4(8):2535−2549. doi: 10.1039/C4CY00161C
[14]	LIU S B, AMADA Y, TAMURA M, NAKAGAWA Y, TOMISHIGE K. One-pot selective conversion of furfural into 1,5-pentanediol over a Pd-added Ir-ReO_x/SiO₂ bifunctional catalyst[J]. Green Chem,2014,16(2):617−626. doi: 10.1039/C3GC41335G
[15]	KOCH O, KOECKRITZ A, KANT M, MARTIN A, SCHOENING A, ARMBRUSTER U, BARTOSZEK M, EVERT S, LANGE B, BIENERT R. Method for producing 1, 2-pentanediol: US, 14115706[P]. 2014.
[16]	KAUFMANN W E, ADAMS R. The use of platinum oxide as a catalyst in the reduction of organic compounds. IV. Reduction of furfural and its derivatives[J]. J Am Chem Soc,1923,45(12):3029−3044.
[17]	BHOGESWARARAO S, SRINIVAS D. Catalytic conversion of furfural to industrial chemicals over supported Pt and Pd catalysts[J]. J Catal,2015,327:65−77. doi: 10.1016/j.jcat.2015.04.018
[18]	TONG T, XIA Q N, LIU X H, WANG Y Q. Direct hydrogenolysis of biomass-derived furans over Pt/CeO₂ catalyst with high activity and stability[J]. Catal Commun,2017,101:129−133. doi: 10.1016/j.catcom.2017.08.005
[19]	MITSUDOME T, NOUJIMA A, MIKAMI Y, MIZUGAKI T, JITSUKAWA K, KANEDA K. Supported gold and silver nanoparticles for catalytic deoxygenation of epoxides into alkenes[J]. Angew Chem Int Ed,2010,49(32):5545−5548.
[20]	KAZANSKY V B, BOROVKOV V Y. The unusual properties of small platinum particles supported on basic carriers[J]. Catal Sci Technol,1994,92:275−280.
[21]	PISAL D S, YADAV G D. Single-step hydrogenolysis of furfural to 1,2-Pentanediol using a bifunctional Rh/OMS2 catalyst[J]. ACS Omega,2019,4(1):1201−1214.
[22]	LIU H L, HUANG Z W, ZHAO F, CUI F, LI X M, XIA C G, CHEN J. Efficient hydrogenolysis of biomass-derived furfuryl alcohol to 1,2- and 1,5-pentanediols over a non-precious Cu-Mg₃AlO_4.5 bifunctional catalyst[J]. Catal Sci Technol,2016,6(3):668−671. doi: 10.1039/C5CY01442E
[23]	DATE N S, CHIKATE R C, ROH H S, RODE C V. Bifunctional role of Pd/MMT-K 10 catalyst in direct transformation of furfural to 1,2-pentanediol[J]. Catal Today,2018,309:195−201. doi: 10.1016/j.cattod.2017.08.002
[24]	GÖTZ D, LUCAS M, CLAUS P. C−O bond hydrogenolysis vs. C=C group hydrogenation of furfuryl alcohol: towards sustainable synthesis of 1,2-pentanediol[J]. React Chem Eng,2016,1:161−164. doi: 10.1039/C5RE00026B
[25]	TONG T, LIU X H, GUO Y, BANIS M N, HU Y F, WANG Y Q. The critical role of CeO₂ crystal-plane in controlling Pt chemical states on the hydrogenolysis of furfuryl alcohol to 1,2-pentanediol[J]. J Catal,2018,365:420−428. doi: 10.1016/j.jcat.2018.07.023
[26]	卫彩云, 谭静静, 夏晓丽, 赵永祥. 煅烧温度对CuMgAl催化糠醇加氢制戊二醇的影响[J]. 化工学报,2019,70:1409−1419. WEI Cai-yun, TAN Jing-jing, ZHAO Yong-xiang. Influence of calcination temperature on CuMgAl catalytic performance for hydrogenation of furfuralcohol to pentanediol[J]. CIESC J,2019,70:1409−1419.
[27]	XU W J, WANG H F, LIU X H, REN J W, WANG Y Q, LU G Z. Direct catalytic conversion of furfural to 1,5-pentanediol by hydrogenolysis of the furan ring under mild conditions over Pt/Co₂AlO₄ catalyst[J]. Chem Commun,2011,47(13):3924−3926. doi: 10.1039/c0cc05775d
[28]	MA C Y, MU Z, LI J J, JIN Y G, CHENG J, LU G Q, HAO Z P, QIAO S Z. Mesoporous Co₃O₄ and Au/Co₃O₄ catalysts for low-temperature oxidation of trace ethylene[J]. J Am Chem Soc,2010,132(8):2608−2613. doi: 10.1021/ja906274t
[29]	ADKINS H, CONNOR R J. The catalytic hydrogenation of organic compounds over copper chromite[J]. Am Chem Soc,1931,53(3):1091−1095. doi: 10.1021/ja01354a041
[30]	LEE J, BURT S P, CARRERO C A, ALBA-RUBIO A C, RO I, O’NEILL B J, KIM H J, JACKSON D H K, KUECH T F, HERMANS I, DUMESIC J A, HUBER G W. Stabilizing cobalt catalysts for aqueous-phase reactions by strong metal-support interaction[J]. J Catal,2015,330:19−27. doi: 10.1016/j.jcat.2015.07.003
[31]	GAO F F, LIU H L, HU X, CHEN J, HUANG Z W, XIA C G. Selective hydrogenolysis of furfuryl alcohol to 1,5- and 1,2-pentanediol over Cu-LaCoO₃ catalysts with balanced Cu⁰-CoO sites[J]. Chin J Catal,2018,39(10):1711−1723. doi: 10.1016/S1872-2067(18)63110-9
[32]	SULMONETTI T P, HU B, LEE S, AGRAWAL P K. JONES C W. Reduced Cu-Co-Al mixed metal oxides for the ring-opening of furfuryl alcohol to produce renewable diols[J]. ACS Sustainable Chem Eng,2017,5(10):8959−8969. doi: 10.1021/acssuschemeng.7b01769
[33]	WIJAYA H W, KOJIMA T, HARA T, ICHIKUNI N, SHIMAZU P S. Synthesis of 1,5-pentanediol by hydrogenolysis of furfuryl alcohol over Ni-Y₂O₃ composite catalyst[J]. ChemCatChem,2017,9(14):2869−2874. doi: 10.1002/cctc.201700066
[34]	YAO S X, WANG X C, JIANG Y J, WU F, CHEN X G, MU X D. One-step conversion of biomass-derived 5-hydroxymethylfurfural to 1,2, 6-hexanetriol over Ni-Co-Al mixed oxide catalysts under mild conditions[J]. ACS Sustainable Chem Eng,2014,2(2):173−180.
[35]	WIJAYA H W, SATO T, TANGE H, HARA T, ICHIKUNI N, SHIMAZU S P. Hydrogenolysis of furfural into 1,5-pentanediol by employing Ni-M (M = Y or La) composite catalysts[J]. Chem Lett,2017,46(5):744−746. doi: 10.1246/cl.170129
[36]	KOSO S, FURIKADO I, SHIMAO A, MIYAZAWA T, KUNIMORI K, TOMISHIGE K. Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol[J]. Chem Comm,2009,106:2035−2037.
[37]	KOSO S, NAKAGAWA Y, TOMISHIGE K. Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide[J]. J Catal,2011,280(2):221−229. doi: 10.1016/j.jcat.2011.03.018
[38]	CHEN K Y, MORI K, WATANABE H, NAKAGAWA Y, TOMISHIGE K. C−O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts[J]. J Catal,2012,294:171−183. doi: 10.1016/j.jcat.2012.07.015
[39]	TOMISHIGE K, NAKAGAWA Y, TAMURA M. Selective hydrogenolysis and hydrogenation using metal catalysts directly modified with metal oxide species[J]. Green Chem,2017,19(13):2876−2924. doi: 10.1039/C7GC00620A
[40]	KUANG B F, ZHANG Q, FANG Y X, BAI Y, QIU S B, WU P, QIN Y L, WANG T J. Ring opening of cyclic ether for selective synthesis of renewable 1,5-pentanediol over Pt/WO₃@SiO₂ catalysts[J]. Ind Eng Chem Res,2020,59(20):9372−9381.
[41]	WANG C, LEE J D, JI Y C, ONN T M, LUO J, MURRAY C B, GORTE R J. A study of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Pt-WO_x/C[J]. Catal Lett,2018,148:1047−1054. doi: 10.1007/s10562-018-2323-6
[42]	FENG S X, NAGAO A, AIHARA T, MIURA H, SHISHIDO T. Selective hydrogenolysis of tetrahydrofurfuryl alcohol on Pt/WO₃/ZrO₂ catalysts: Effect of WO₃ loading amount on activity[J]. Catal Today,2018,303:207−212. doi: 10.1016/j.cattod.2017.08.058
[43]	杨晓, 陈长林. Y₂O₃对 Pt /WO₃ -ZrO₂催化剂催化四氢糠醇加氢制备 1,5-戊二醇的影响[J]. 南京工业大学学报,2019,41(2):149−154. YANG Xiao, CHEN Chang-lin. The effect of Y₂O₃ on Pt /WO₃ -ZrO₂ catalyst for the hydrogenation of tetrahydrofurfuryl alcohol to 1,5-pentanediol[J]. J Nanjing Technol Univ,2019,41(2):149−154.
[44]	SOGHRATI E, POH C K, DU Y H, GAO F, KAWI P S, BORGNA A. C-O hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-Pentanediol Over bi-functional nickel-tungsten catalysts[J]. ChemCatChem,2018,10(20):4652−4664. doi: 10.1002/cctc.201800783