Catalytic conversion of biomass-derived furfural into pentanediols

doi:10.16085/j.issn.1000-6613.2017-0885

Abstract

Abstract: Compared to the traditional production of pentanediols from fossil resources,the production of pentanediols from biomass based furfural possessed various advantages such as the abundant raw materials and the green production process. In this paper,the status of the research on the production of pentanediols from biomass based furfural was discussed. A summary on the hydrogenation of furfural to pentanediols over rhodium,iridium,platinum and copper based catalysts was presented. Two kinds of reaction routes of furfural hydrogenolysis were also discussed. As a consequence,issues realated to the process of furfural hydrogenolysis,such as low reactant concentration,low reaction activity and quite high reaction pressure,were also presented. To design a process that is economical and environmental,the production techniques of pentanediols from biomass derived furfural hydrogenation were prospected in this paper. This review can be used for a reference in developing highly active catalytic system for the furfural hydrogenolysis under mild conditions.

Key words: biomass, catalytic hydrogenation, furfural, pentanediol

摘要： 生物基糠醛制备戊二醇的工艺相比于传统的石油基路线，具有原料来源广泛、生产过程绿色无污染等优点。本文总结了国内外以生物基糠醛为原料制备戊二醇的研究现状，并对应用于糠醛催化加氢制备戊二醇的铑、铱、铂、铜基催化剂分别进行了归纳整理，同时详细论述了两种糠醛氢解路线，即糠醛加氢分别以糠醇和四氢糠醇为中间体而氢解生成戊二醇的过程。在此基础上，提出了解决目前糠醛氢解制备戊二醇过程中存在的反应物浓度低、活性差、反应压力高等问题的建议。对未来从经济、环保等多角度出发设计并完善生物基戊二醇的生产工艺以及拓展高效利用生物基糠醛制备下游精细化工产品的方法做出了展望。为开发在温和条件下高效、稳定的催化生物基糠醛氢解的催化剂体系提供了参考。

关键词: 生物质, 催化加氢, 糠醛, 戊二醇

CLC Number:

TQ223.1

FAN Dongna, LIU Xiaoran, WANG Xicheng, YU Yifeng, CHEN Aibing. Catalytic conversion of biomass-derived furfural into pentanediols[J]. Chemical Industry and Engineering Progress, 2018, 37(03): 938-946.

樊冬娜, 刘晓然, 王喜成, 于奕峰, 陈爱兵. 生物基糠醛催化转化制备戊二醇的研究进展[J]. 化工进展, 2018, 37(03): 938-946.

References

[1] DEGUCHI S,TSUJⅡ K,HORIKOSHI K. Crystalline-to-amorphous transformation of cellulose in hot and compressed-water and its implications for hydrothermal conversion[J]. Green Chemistry,2008,10(2):191-196.
[2] BOZELL J J,MOENS L,ELLIOTT D C,et al. Production of levulinic acid and use as a platform chemical for derived products[J]. Resources,Conservation and Recycling,2000,28:227-239.
[3] 高美香,刘宗章,张敏华. 生物质转化制糠醛工艺的研究进展[J]. 化工进展,2013,32(4):878-884. GAO M X,LIU Z Z,ZHANG M H. Progress in the production of furfural from biomass[J]. Chemical Industry and Engineering Progress,2013,32(4):878-884.
[4] KARINEN R,VILONEN K,NIEMELA M. Biorefining:heterogeneously catalyzed reactions of carbohydrates for the production of furfural and hydroxymethylfurfural[J]. ChemSusChem,2011,4(8):1002-1016.
[5] BOZELL J J,PETERSEN G R. Technology development for the production of biobased products from biorefinery carbohydrates-the US Department of Energy's "Top 10" revisited[J]. Green Chemistry,2010,12(4):539-554.
[6] NAKAGAWA Y,TAMURA M,TOMISHIGE K. Catalytic conversions of furfural to pentanediols[J]. Catalysis Surveys from Asia,2015,19(4):249-256.
[7] BINDER J B,RAINES R T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals[J]. Journal of the American Chemical Society,2009,131:1979-1985.
[8] LANGE J P,HEIDE V D E,BUIJTENEN V J,et al. Furfural——a promising platform for lignocellulosic biofuels[J]. ChemSusChem,2012,5(1):150-166.
[9] 徐保明,唐强,罗岩,等. 1,2-戊二醇的新合成方法及工艺优化研究[J]. 高校化学工程学报,2014,28(1):92-97. XU B M,TANG Q,LUO Y,et al. Study on the new synthetic method of 1,2-pentanediol and process optimization thereof[J]. Journal of Chemical Engineering of Chinese Universities,2014,28(1):92-97.
[10] NAKAGAWA Y,TOMISHIGE K. Production of 1,5-pentanediol from biomass via furfural and tetrahydrofurfuryl alcohol[J]. Catalysis Today,2012,195(1):136-143.
[11] NAKAGAWA Y,TAMURA M,TOMISHIGE K. Catalytic reduction of biomass-derived furanic compounds with hydrogen[J]. ACS Catalysis,2013,3(12):2655-2668.
[12] 马要耀,邬一凡. 国内外1,5-戊二醇和1,6-己二醇市场分析[J]. 精细与专用化学品,2016,24(12):5-10. MA Y Y,WU Y F. Global market analysis of 1,5-pentanediol and 1,6-hexanediol[J]. Fine and Specialty Chemicals,2016,24(12):5-10.
[13] SERRANO R J C,LUQUE R,SEPULVEDA E A. Transformations of biomass-derived platform molecules:from high added-value chemicals to fuels via aqueous-phase processing[J]. Chemical Society Reviews,2011,40(11):5266-5281.
[14] CHHEDA J N,ROMAN L Y,DUMESIC J A. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono-and poly-saccharides[J]. Green Chemistry,2007,9(4):342-350.
[15] CHAREONLIMKUN A,CHAMPREDA V,SHOTIPRUK A,et al. Reactions of C₅ and C₆-sugars,cellulose,and lignocellulose under hot compressed water(HCW)in the presence of heterogeneous acid catalysts[J]. Fuel,2010,89(10):2873-2880.
[16] ZHANG J,LIN L,LIU S. Efficient production of furan derivatives from a sugar mixture by catalytic process[J]. Energy & Fuels,2012,26(7):4560-4567.
[17] 丁小兵. 1,2-戊二醇的合成[J]. 安徽化工,2002,119(5):22-23. DING X B. Synthesis of 1,2-pentanediol[J]. Anhui Chemical Industry,2002,119(5):22-23.
[18] 黄集钺,白晓琳,程光剑,等. 1,5-戊二醇的制备与应用[J]. 化工中间体,2007(2):11-13. HUANG J Y,BAI X L,CHENG G J,et al. Preparation and application of 1,5-pentanediol[J]. Chemical Intermediate,2007(2):11-13.
[19] KOSO S,FURIKADO I,SHIMAO A,et al. Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol[J]. Chemical Communications,2009,15:2035-2037.
[20] KOSO S,UEDA N,SHINMI Y,et al. Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh/SiO₂[J]. Journal of Catalysis,2009,267(1):89-92.
[21] CHEN K,KOSO S,KUBOTA T,et al. Chemoselective hydrogenolysis of tetrahydropyran-2-methanol to 1,6-hexanediol over rhenium-modified carbon-supported rhodium catalysts[J]. ChemCatChem,2010,2(5):547-555.
[22] CHIA M,PAGAN T Y J,HIBBITTS D,et al. Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium-rhenium catalysts[J]. Journal of the American Chemical Society,2011,133(32):12675-12689.
[23] CHEN K,MORI K,WATANABE H,et al. C-O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts[J]. Journal of Catalysis,2012,294:171-183.
[24] PONEC V. On the role of promoters in hydrogenations on metals;α,β-unsaturated aldehydes and ketones[J]. Applied Catalysis A:General,1997,149:27-48.
[25] MAKI-ARVELA P,HAJEK J,SALMI T,et al. Chemoselective hydrogenation of carbonyl compounds over heterogeneous catalysts[J]. Applied Catalysis A:General,2005,292:1-49.
[26] YU W,POROSOFF M D,CHEN J G. Review of Pt-based bimetallic catalysis:from model surfaces to supported catalysts[J]. Chemical Reviews,2012,112(11):5780-5817.
[27] RODIANSONO,KHAIRI S,HARA T,et al. Highly efficient and selective hydrogenation of unsaturated carbonyl compounds using Ni-Sn alloy catalysts[J]. Catalysis Science & Technology,2012,2(10):2139-2145.
[28] NAKAGAWA Y,NAKAZAWA H,WATANABE H,et al. Total hydrogenation of furfural over a silica-supported nickel catalyst prepared by the reduction of a nickel nitrate precursor[J]. ChemCatChem,2012,4(11):1791-1797.
[29] CHEN B,LI F,HUANG Z,et al. Tuning catalytic selectivity of liquid-phase hydrogenation of furfural via synergistic effects of supported bimetallic catalysts[J]. Applied Catalysis A:General,2015,500:23-29.
[30] MERAT N,GODAWA C,GASET A. High selective production of tetrahydrofurfuryl alcohol:Catalytic hydrogenation of furfural and furfuryl alcohol[J]. Journal of Chemical Technology & Biotechnology,1990,48:145-159.
[31] BIRADAR N S,HENGNE A M,BIRAJDAR S N,et al. Single-pot formation of THFAL via catalytic hydrogenation of FFR over Pd/MFI catalyst[J]. ACS Sustainable Chemistry & Engineering,2014,2(2):272-281.
[32] NAKAGAWA Y,TAKADA K,TAMURA M,et al. Total hydrogenation of furfural and 5-hydroxymethylfurfural over supported Pd-Ir alloy catalyst[J]. ACS Catalysis,2014,4(8):2718-2726.
[33] SCHNIEPP L E,GELLER H H. Prepartion of dihydropyran,sigma-hydroxyvaleraldehyde and 1,5-pentanediol from tetrahydrofurfuryl alcohol[J]. Journal of the American Chemical Society,1946,68(8):1646-1648.
[34] 丁璟,赵俊琦,程时标,等. 生物基1,6-己二醇的研究进展[J]. 化工进展,2015,34(12):4209-4213. DING J,ZHAO J Q,CHENG S B,et al. Advances in production of biobased 1,6-HDO[J]. Chemical Industry and Engineering Progress,2015,34(12):4209-4213.
[35] SEMAN M,KONDO J N,DOMEN K,et al. Reactive and inert surface species observed during methanol oxidation over silica-supported molybdenum oxide[J]. Journal of Physical Chemistry B,2002,106:12965-12977.
[36] KOSO S,WATANABE H,OKUMURA K,et al. Comparative study of Rh-MoO_x and Rh-ReO_x supported on SiO₂ for the hydrogenolysis of ethers and polyols[J]. Applied Catalysis B:Environmental,2012,111:27-37.
[37] AMADA Y,SHINMI Y,KOSO S,et al. Reaction mechanism of the glycerol hydrogenolysis to 1,3-propanediol over Ir-ReO_x/SiO₂ catalyst[J]. Applied Catalysis B:Environmental,2011,105(1-2):117-127.
[38] KOSO S,WATANABE H,OKUMURA K,et al. Stable low-valence ReO_x cluster attached on Rh metal particles formed by hydrogen reduction and its formation mechanism[J]. Journal of Physical Chemistry C,2012,116(4):3079-3090.
[39] AMADA Y,WATANABE H,TAMURA M,et al. Structure of ReO_x clusters attached on the Ir metal surface in Ir-ReO_x/SiO₂ for the hydrogenolysis reaction[J]. Journal of Physical Chemistry C,2012,116(44):23503-23514.
[40] NAKAGAWA Y,SHINMI Y,KOSO S,et al. Direct hydrogenolysis of glycerol into 1,3-propanediol over rhenium-modified iridium catalyst[J]. Journal of Catalysis,2010,272(2):191-194.
[41] SHINMI Y,KOSO S,KUBOTA T,et al. Modification of Rh/SiO₂ catalyst for the hydrogenolysis of glycerol in water[J]. Applied Catalysis B:Environmental,2010,94(3/4):318-326.
[42] SHIMAO A,KOSO S,UEDA N,et al. Promoting effect of Re addition to Rh/SiO₂ on glycerol hydrogenolysis[J]. Chemistry Letters,2009,38(6):540-541.
[43] AMADA Y,KOSO S,NAKAGAWA Y,et al. Hydrogenolysis of 1,2-propanediol for the production of biopropanols from glycerol[J]. ChemSusChem,2010,3(6):728-736.
[44] NAKAGAWA Y,NING X,AMADA Y,et al. Solid acid co-catalyst for the hydrogenolysis of glycerol to 1,3-propanediol over Ir-ReO_x/SiO₂[J]. Applied Catalysis A:General,2012,433/434:128-134.
[45] AMADA Y,WATANABE H,HIRAI Y,et al. Production of biobutanediols by the hydrogenolysis of erythritol[J]. ChemSusChem,2012,5(10):1991-1999.
[46] KOSO S,NAKAGAWA Y,TOMISHIGE K. Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide[J]. Journal of Catalysis,2011,280(2):221-229.
[47] TOMISHIGE K,TAMURA M,NAKAGAWA Y. Role of Re species and acid cocatalyst on Ir-ReO_x/SiO₂ in the C-O hydrogenolysis of biomass-derived substrates[J]. Chemical Record,2014,14(6):1041-1054.
[48] CHATTERJEE M,KAWANAMI H,ISHIZAKA T,et al. An attempt to achieve the direct hydrogenolysis of tetrahydrofurfuryl alcohol in supercritical carbon dioxide[J]. Catalysis Science & Technology,2011,1(8):1466-1471.
[49] LIU S,AMADA Y,TAMURA M,et al. One-pot selective conversion of furfural into 1,5-pentanediol over a Pd-added Ir-ReO_x/SiO₂bifunctional catalyst[J]. Green Chemistry,2014,16(2):617-626.
[50] LIU S B,AMADA Y,TAMURA M,et al. Performance and characterization of rhenium-modified Rh-Ir alloy catalyst for one-pot conversion of furfural into 1,5-pentanediol[J]. Catalysis Science & Technology,2014,4(8):2535-2549.
[51] WANG Z Q,PHOLJAROEN B,LI M X,et al. Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Ir-MoO_x/SiO₂catalyst[J]. Journal of Energy Chemistry,2014,23(4):427-434.
[52] XU W J,WANG H F,LIU X H,et al. Direct catalytic conversion of furfural to 1,5-pentanediol by hydrogenolysis of the furan ring under mild conditions over Pt/Co₂AlO₄ catalyst[J]. Chemical Communications,2011,47(13):3924-3926.
[53] WU J,SHEN Y M,LIU C H,et al. Vapor phase hydrogenation of furfural to furfuryl alcohol over environmentally friendly Cu-Ca/SiO₂ catalyst[J]. Catalysis Communications,2005,6(9):633-637.
[54] NAGARAJA B M,KUMAR V S,SHASIKALA V,et al. A highly efficient Cu/MgO catalyst for vapour phase hydrogenation of furfural to furfuryl alcohol[J]. Catalysis Communications,2003,4(6):287-293.
[55] NAGARAJA B M,PADMASRI A H,RAJU B D,et al. Vapor phase selective hydrogenation of furfural to furfuryl alcohol over Cu-MgO coprecipitated catalysts[J]. Journal of Molecular Catalysis A:Chemical,2007,265(1/2):90-97.
[56] DIEZ V K,APENTEGUIA C R,DI COSIMO J I. Aldol condensation of citral with acetone on MgO and alkali-promoted MgO catalysts[J]. Journal of Catalysis,2006,240(2):235-244.
[57] MIZUGAKI T,YAMAKAWA T,NAGATSU Y,et al. Direct transformation of furfural to 1,2-pentanediol using a hydrotalcite-supported platinum nanoparticle catalyst[J]. ACS Sustainable Chemistry & Engineering,2014,2(10):2243-2247.
[58] 王艳芹,马荣芳,卢冠忠,等. 一种用于呋喃类衍生物开环加氢的金属/稀土基复合催化剂:CN201510055386.0[P]. 2015-08-05. WANG Y Q,MA R F,LU G Z,et al. A metal/rare composite catalyst for ring-opening hydrogenation of furan derivatives:CN201510055386.0[P]. 2015-08-05.
[59] 崔健,崔晓桐. 糠醛一步加氢生产1,2-戊二醇的方法:201210397581.8[P]. 2013-02-13. CUI J,CUI X T. One-step hydrogenation of furfural to 1,2-pentanediol:CN201210397581.8[P]. 2013-02-13.
[60] TAYLOR M J,DURNDELL L J,ISAACS M A,et al. Highly selective hydrogenation of furfural over supported Pt nanoparticles under mild conditions[J]. Applied Catalysis B:Environmental,2016,180:580-585.
[61] BEHRENS M,LOLLI G,MURATOVA N,et al. The effect of Al-doping on ZnO nanoparticles applied as catalyst support[J]. Physical Chemistry Chemical Physics,2013,15(5):1374-1381.
[62] BELL J M,KUBLER D G,SARTWELL P,et al. Acetal formation for ketones and aromatic aldehydes with methanol[J]. Journal of Organic Chemistry,1965,30:4284-4292.
[63] BEL'SKⅡ I F,SHUIKIN N I. Catalytic hydrogenation and hydrogenolysis of furan compounds[J]. Russian Chemical Reviews,1963,32(6):307-321.
[64] 王艳芹,徐文杰,卢冠忠,等. 一种呋喃衍生物开环加氢反应的催化剂:201110001536.1[P]. 2011-05-25. WANG Y Q,XU W J,LU G Z,et al. A catalyst for ring-opening hydrogenation of furan derivatives:CN201110001536.1[P]. 2011-05-25.
[65] LIU H L,HUANG Z W,ZHAO F,et al. Efficient hydrogenolysis of biomass-derived furfuryl alcohol to 1,2-and 1,5-pentanediols over nonprecious Cu-Mg₃AlO_4.5 bifunctional catalyst[J]. Catalysis Science & Technology,2016,6:668-671.
[66] 黄志威,陈静,刘海龙,等. 一种呋喃衍生物选择氢解制戊二醇的方法:201510475234.6[P]. 2015-12-09. HUANG Z W,CHEN J,LIU H L,et al. A method for selective hydrogenolysis of furan derivatives to pentanediol:CN201510475234.6[P]. 2015-12-09.
[67] LIU H L,HUANG Z W,KANG H X,et al. Selective hydrogenolysis of biomass-derived furfuryl alcohol into 1,2-and 1,5-pentanediol over highly dispersed Cu-Al₂O₃ catalysts[J]. Chinese Journal of Catalysis,2016,37(5):700-710