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Catalytic Conversion of Bio-Based Platform Compounds to Fufuryl Alcohol

Qiyue Yang , Qiaomei Wu , Jiarong Qiu , Xianhai Zeng , Xing Tang , Liangqing Zhang

Progress in Chemistry ›› 2022, Vol. 34 ›› Issue (8) : 1748 -1759.

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Progress in Chemistry ›› 2022, Vol. 34 ›› Issue (8) : 1748-1759 DOI: 10.7536/PC211007
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Catalytic Conversion of Bio-Based Platform Compounds to Fufuryl Alcohol
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Abstract

Furfuryl alcohol (FOL), as an important and promising organic chemical product, can be effectively converted into various high-value chemicals, such as furfural resin, urea-formaldehyde resin, phenolic resin, fruit acid, plasticizer, rocket fuel, etc. The green FOL production by catalytic hydrogenation using furfural (FAL), xylose, and fructose as raw materials has good application prospects and research values. This article systematically reviews the research status of the FOL production from FAL, xylose, and fructose on the recent advances, and summarizes from the aspects of catalyst types, catalytic efficiency and mechanism for FOL production. On this basis, the development trends of the FOL production by catalytic hydrogenation are prospected, which may provide theoretical guidance and useful reference for developing new efficient green and stable catalytic system.

Contents

1 Introduction

2 Preparation of FOL from different substrates by catalytic conversion

2.1 Preparation of FOL from FAL by catalytic conversion

2.2 Preparation of FOL from xylose by one-pot method

2.3 Preparation of FOL from fructose by one-pot method

3 Conclusion and outlook

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Keywords

furfuryl alcohol / catalyst / furfural / xylose / fructose

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Qiyue Yang, Qiaomei Wu, Jiarong Qiu, Xianhai Zeng, Xing Tang, Liangqing Zhang. Catalytic Conversion of Bio-Based Platform Compounds to Fufuryl Alcohol. Progress in Chemistry, 2022, 34(8): 1748-1759 DOI:10.7536/PC211007

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1 Introduction

With the continuous exploitation and extensive use of fossil resources, the deterioration of the ecological environment and the depletion of fossil resources have become increasingly obvious, and the development of renewable clean energy to replace traditional energy has become an inevitable trend[1⇓⇓~4]. At present, more and more enterprises and researchers are developing economical, efficient, energy-saving and environmentally friendly processes based on renewable energy to achieve sustainable production of fuels and fine chemicals. Among many renewable resources, biomass resources have the advantages of wide source, abundant reserves and low price. It is the only renewable organic carbon resource in nature, which can be converted into various fuels and high value-added chemicals. Therefore, biomass as an alternative to traditional fossil energy has been widely concerned and studied, and lignocellulose is a cheap and easily available non-food resource in biomass resources.It is composed of cellulose (40% ~ 50%), lignin (15% ~ 20%) and hemicellulose (25% ~ 35%), which can be converted into biomass fuels such as bioethanol and hydrogen. With the accelerated development of green circular economy, this kind of resource is expected to replace petroleum as "industrial blood"[5⇓⇓~8]. Using renewable lignocellulose-derived platform compounds to produce high value-added products has become a more effective way to deal with the current resource and energy crisis[9].
Through biorefinery, lignocellulose and its derived platform compounds can be converted into value-added chemicals and materials, such as furfural (FAL), 5-hydroxymethylfurfural (HMF), 5-methylfurfural, 2,5-furandimethanol, alkyl levulinate, γ-valerolactone, xylo-oligosaccharides, cellulose-based carbon aerogels and hydrogels[10⇓⇓⇓⇓⇓~16]. Among them, FAL, as an important bio-based platform molecule, can be used to produce downstream products of FAL through several processes including hydrogenation, oxidation and cyanidation (Fig. 1). Among them, the application of FAL is mainly focused on its hydrogenation, and 62% of FAL is used in industry to produce FOL. Furfuryl alcohol (FOL) can be obtained by selective hydrogenation of aldehyde group catalyzed by different catalytic systems[17].
FOL, also known as furfuryl alcohol, is a transparent yellow liquid. FOL has low viscosity, high reactivity and excellent solvent characteristics, and because of its hydroxymethyl characteristics, it can be used to prepare various value-added chemical derivatives through a variety of chemical unit reactions such as polymerization, hydroxymethylation and alkoxylation (Figure 2). In addition, FOL is an important organic chemical raw material with high application value. For example, FOL is usually used as an adhesive and corrosion inhibitor in the foundry industry at high concentration[18⇓~20]. FOL can be used as resin and wetting agent in cold forming grinding wheel; FOL is usually converted to other compounds as an intermediate in the synthesis of organic compounds[11].
In 1864, the first laboratory synthesis of FOL was reported, using amalgam to reduce FAL[17]. In 1948, Wojcik reported that the yield of FOL was about 96% ~ 99% at 175 ℃ using copper-chromium oxide as catalyst[21,22]. Currently, a Cu-Cr catalyst is used commercially, but the catalyst requires harsh reaction conditions, is prone to the formation of highly toxic Cr compounds, and is prone to rapid deactivation problems associated with coke formation[23][24]. In addition, considering that FAL is a highly unsaturated compound containing conjugated C = C and C = O bonds and furan heterocycles, side reactions such as hydrogenolysis, over-hydrogenation of unsaturated groups, and furan ring opening are involved, generating various by-products. Therefore, the selectivity of catalytic hydrogenation is still the key challenge of FAL hydrogenation. Therefore, it is expected to explore a class of catalysts with high catalytic activity and environmental friendliness for the selective hydrogenation of FAL to FOL. In this paper, the catalytic systems for the preparation of FOL in recent years were systematically summarized, and the future research directions were prospected, in order to provide a reference for the preparation of FOL by catalytic conversion of bio-based platform compounds.

2 Preparation of FOL by Catalytic Conversion of Different Substrates

There are three common methods to prepare FOL: the first is to use FAL as raw material to prepare FOL by catalytic hydrogenation process[10]; In the second method, xylose is used as a raw material, the xylose is dehydrated by acid catalysis to obtain FAL, and the FAL is hydrogenated to prepare FOL[25]; The third method is to use fructose as raw material, dehydrate fructose to produce HMF by acid catalysis, and decarbonylate HMF to produce FOL[26].

2.1 Preparation of FOL by catalytic hydrogenation of FAL

The reaction of FAL hydrogenation is based on the active aldehyde group on the FAL molecule and the carbon-carbon double bond on the furan ring. Hydrogenation of FAL first produces FOL, and further hydrogenation will produce tetrahydrofurfuryl alcohol (THFA), 2-methylfuran (2-MF) and other products. At present, the production technology of preparing FOL from FAL is relatively mature. There are three production methods of preparing FOL from FAL in the world: 1) Conijero method, namely furfural reduction method, which prepares FOL by the reaction of FAL and concentrated sodium hydroxide without additional H2. The equipment is simple and easy to promote, but the main and side reactions are half and half, which is not easy to separate and consumes a lot of organic solvents[27]. 2) Atmospheric pressure gas phase hydrogenation method, which has been successfully developed and industrialized abroad as early as 1956, is the most advanced FAL hydrogenation process at present. Most foreign FOL manufacturers adopt this process, such as Quaker Oats Company in the United States[28]. In 2000, the chlor-alkali plant in Puyang City, Henan Province, China also built an atmospheric FOL production line, which improved the structure of FOL production process in China to a certain extent[28]. The atmospheric pressure gas phase hydrogenation method has that advantage of low required temperature, long production cycle, low labor intensity, and easy recovery and regeneration of the catalyst, and has the disadvantage of large required equipment volume, high energy consumption, long device process, large investment, complex operation, and low yield, thereby limiting its wide application[27,28]. 3) High pressure liquid phase hydrogenation method, in which the catalyst is suspended in FAL and hydrogenated at medium pressure or high pressure at 180-220 ℃. The device used is generally a tubular reactor. The product FOL obtained has good quality, high yield, less side reactions and low process cost. Therefore, most manufacturers in China adopt this method, but its disadvantages are that high pressure requires high equipment and has potential safety hazards, product quality is unstable, and unrecovered light component by-products with high added value will pollute the environment[27,28]. At present, the catalysts used in FOL production are mainly divided into the following two categories: one is copper oxide catalyst; One is alloy catalyst. Copper is the active component of these two kinds of catalysts, followed by nickel and cobalt. The addition of Cr, K, Ba, Ca as co-catalysts can inhibit the occurrence of side reactions, and improve the selectivity and conversion of FAL to FOL[27].
Based on the analysis of the above situation, there are still some problems in the current situation of FOL production process technology, especially the catalysts used in the liquid phase hydrogenation process of some manufacturers in China are still toxic and easy to cause environmental pollution, and the catalysts used in the gas phase hydrogenation process are mostly imported and expensive, which greatly limits the production of FOL in China. Therefore, researchers began to develop non-noble metal (non-toxic) and supported noble metal catalysts, and systematically studied the hydrogenation of FAL to FOL in gas and liquid phase systems, in order to achieve large-scale application and solve the problems faced by the current FOL production process to a greater extent[27⇓⇓⇓~31].
According to the different types of hydrogen source, the catalytic reaction of FAL can be divided into the catalytic reaction with exogenous molecular H2 as the hydrogen source and the catalytic reaction with non-exogenous H2 as the hydrogen source, in which the alcohol as hydrogen source is the main part of the non-exogenous H2 hydrogen source. The catalytic reaction system for selective hydrogenation of FAL to FOL and its latest research progress in recent years are summarized from two hydrogen sources of hydrogen and alcohols respectively.

2.1.1 Catalytic Synthesis of FOL from FAL Using Molecular H2 as Hydrogen Source

Molecular H2 generally need to be in the presence of a catalyst to show efficient reduction ability[8]. The catalysts currently used to catalyze FAL to FOL can be divided into noble metal catalysts (see Table 1) and non-noble metal catalysts (see Table 2).
Precious metals mainly refer to gold, silver and platinum group metals (ruthenium, rhodium, palladium, osmium, iridium, platinum) and other eight metal elements. Noble metal catalysts are widely used in various energy, chemical and metallurgical production processes. They can catalyze a single carbon compound to produce multi-carbon hydrocarbons, esters, alcohols, aldehydes, ketones and other organic compounds. Therefore, the preparation and application of noble metal catalysts are of great research significance. To date, a variety of noble metals have been studied, such as Au, Ru, Pt, Pd, etc. (See Table 1)[32][33][34][35,36]. Platinum catalyst, as one of the most widely used precious metal catalysts, has been widely concerned by scholars in the past two years. Li et al. Prepared Pt/m-CN-x by ultrasonic impregnation-assisted ethylene glycol reduction method, and applied it to the selective hydrogenation of FAL to FOL[37]. It was found that the Pt/m-CN-2 catalyst had the best catalytic performance, the selectivity of FOL was 99. 3% and the conversion of FAL was 98. 5% when isopropanol was used as solvent, and it could be recycled for 5 times without obvious deactivation. Sun Wang also prepared a series of Pt/ (Fe, Co) -BTC-y catalysts with ethylene glycol as reducing agent to promote the selective hydrogenation of FAL to FOL[38]. With Pt/ (Fe, Co) -BTC-2 as catalyst and isopropanol as solvent, the conversion of FAL was 98%, the selectivity of FOL was 99%, and the yield of FOL was 97% at 70 ℃ for 2 H under 1 MPa H2. The catalyst could be reused for 5 times without obvious deactivation, and its overall catalytic performance was slightly inferior to that of Li et al[37]. Gao et al. Prepared CeO2 supported PtFe alloy nanoparticles for FAL catalytic hydrogenation[39]. With Pt3Fe/CeO2 as catalyst and isopropanol as solvent, the conversion of FAL was 99. 8%, the selectivity of FOL was more than 99. 2%, and the selectivity of FOL was more than 99% after six runs at 2 MPa H2 and 100 ℃ for 4 H, showing more excellent catalytic performance. Tolek et al. Prepared Pt-Co/TiO2 catalyst by flame spraying[40]. In this study, it was found that the formation of particles under high temperature flame was beneficial to the high dispersion of platinum and the formation of platinum-titanate interface, which promoted the conversion of FAL to FOL. The catalyst Pt-0.2Co/TiO2 has the best performance, and the FAL conversion and FOL selectivity reach 100% and 97. 5%, respectively, when methanol is used as solvent at 50 ℃ and 2 MPa H2 for 2 H. Wang et al. Prepared Pd/TiH2 catalysts with different Pd loadings by wet impregnation method, and the FAL conversion was close to 100% with 0.5 Pd/TiH2 as catalyst and isopropanol as solvent at 60 ℃ and 1 MPa H2 for 3 H.The selectivity of FOL was 73%, but the catalyst was deactivated in the second cycle. It was found that the Pd particles of the used catalyst were aggregated and partially oxidized, and the structure and surface composition of the TiH2 support were also changed[41]. Tukacs et al. Used Ru/Ph2P(CH2)4PPh2 as a homogeneous catalyst to catalyze the hydrogenation of FAL under solvent-free conditions. Under these conditions, no by-products were produced, and the efficient production of FOL was achieved with 100% atom economy, which could be recycled for 12 consecutive times without affecting the catalytic performance of the catalyst[42]. However, Ramirez-Barria et al. Studied the hydrogenation of FAL in aqueous phase, and used Ru (CO)/rGO as a catalyst to catalyze FAL to produce FOL at room temperature, which could obtain 91% FOL yield, and found that the catalyst showed excellent stability and could be reused at least four times without deactivation[43]. Li et al. Used Au/Al2O3 as a catalyst to catalyze the continuous gas-phase hydrogenation of FAL to FOL[32]. In the following years, they prepared a Au/CeO2 catalyst, which also achieved 100% FOL selectivity[44]. Controlled synthesis of metal-metal oxide heterostructures is difficult for transition metal oxide decorated noble metals. To solve this problem, Yu et al. Found that IrCo alloy nanoparticles could be transformed into nanostructures with close contact of Ir-CoOx by in-situ calcination and selective reduction[45]. With Ir-CoOx/A12O3 as catalyst, ethanol as solvent, at 45 ℃ and 0.8 MPa H2, the conversion of FAL can reach 98%, the selectivity of FOL is more than 99%, and after five cycles, the selectivity of FOL is basically unchanged, and the cycle stability is good.
Generally, for noble metal catalysts, high catalytic activity for FAL hydrogenation can be shown even under mild reaction conditions, but their scarcity and high price limit their further application. In addition, reactant molecules are easily adsorbed on noble metal surfaces, such as Pd, in a manner that may lead to undesirable side reactions, such as C = C hydrogenation or C — C/C — O cracking[46]. Hao et al. Used activated carbon as a catalytic support to prepare Cu-N co-doped activated carbon Cu-N/OAC by one-step complexation, so that the copper nanoparticles were highly dispersed on the surface of the support with Cu0 and Cu+, which significantly improved the catalytic activity of FAL hydrogenation[46]. Cu-N/OAC-800 showed excellent activity with FAL conversion of 99.5% and FOL selectivity of 98.4% in 2-propanol at 150 ° C for 6 H under 2 MPa H2. After five cycles, the conversion of FAL and the selectivity of FOL were both more than 95%, indicating that the catalyst Cu-N/OAC-800 had good recyclability. They found that activated carbon has the characteristics of low price, large specific surface area and excellent hydrophobicity compared with SiO2 and γ-Al2O3. In contrast, Zhang et al. Used SiO2 as the catalytic carrier to prepare the Cu2Zn/SiO2-IS catalyst, and water was used as the solvent to react at 120 ° C for 4 H, the FAL conversion was 81.9%, and the FOL selectivity was 94.8%, and after the fourth recycling, the FAL conversion on Cu2Zn/SiO2-IS was reduced to 73% and the FOL selectivity was reduced to 80%, so its overall catalytic performance was slightly lower than that of the Cu-N/OAC-800 catalyst with activated carbon as the carrier[47]. Guerrero-Torres et al. Also used carbonaceous materials as carriers, but did not study the effect of carriers, but explored the use of natural, cheap and abundant biopolymers (such as chitosan) to prepare Cu-based catalysts for the preparation of FOL from FAL[48]. They used Chi30Cu (30wt% Cu) as a catalyst and cyclopentyl methyl ether (CPME) as a solvent at 190 ° C for 5 H with a H2 flow rate of 10 mL/min, the conversion of FAL was 78% and the yield of FOL was 64%, and the catalyst was gradually deactivated after use, which may be due to the partial oxidation of Cu0 in the catalytic process. In order to improve the catalytic activity and selectivity, some scholars have explored doping a small amount of heteroatoms in the catalyst. Arundhathi et al. Mainly studied the effect of magnesium doping on the catalytic performance, and synthesized a magnesium-doped Cu@Mg/γ-Al2O3 catalyst. Under solvent-free conditions and 170 ℃, 2 MPa H2 reaction conditions, the conversion of FAL can reach 99%, and the selectivity of FOL can reach 94%. Moreover, the catalyst has strong stability and can run continuously for six times, and the yield of FOL is more than 90%[49].
For Ni-based catalysts, Wang et al. Used lignin as the main carbon precursor and mesoporous carbon as the catalytic support to synthesize ferromagnetic Ni-doped lignin-derived ordered mesoporous carbon Ni @ OMC by evaporation-induced self-assembly method[50]. The conversion of FAL was 92. 3%, the yield of FOL was 91. 0%, and the selectivity was 98. 6% when 1-propanol was used as solvent at 180 ℃ and 3 MPa H2 for 12 H. It was found that after five cycles, the catalytic activity decreased slightly, but compared with the previous Ni-based catalyst, the catalyst weakened the disadvantage of the current heat treatment and the decrease of stability caused by nickel agglomeration in the reaction process, and the catalyst could be separated by a magnet, which was very convenient. Tian et al. Prepared C@Ni3P-1 by temperature-programmed reduction to catalyze FAL to FOL with 2-propanol as solvent at 160 ° C for 4 H under 1.6 MPa H2, the conversion of FAL was 97%, and the selectivity of FOL was 96.3%[51]. For comparison, hollow spherical nano Ni3P catalyst was prepared by electroless plating in alkaline environment, and the conversion of FAL was 100% and the selectivity of FOL was 95. 6% with Ni3P as catalyst and isopropanol as solvent at 120 ℃ and 1.6 MPa H2 for 4 H[52]. For the Ni3P catalyst, the selectivity of FOL did not change significantly after 4 cycles, but the conversion of FAL decreased from 94% to 69%. The authors also evaluated the reusable performance of C@Ni3P-1 and found that the selectivity of FOL was almost unchanged, while the conversion of FAL decreased from 97% to 88%[52]. The above results indicate that the deactivation rate of C@Ni3P-1 is slower than that of Ni3P, which is due to the protection of Ni3P nanoparticles by porous carbon. MacIntosh et al. Catalyzed the gas-phase hydrogenation of FAL to FOL at 180 ° C over standard impregnated nickel-based catalysts (Ni/SiO2, Ni/CeO2, Ni/TiO2) and contrasted the same reaction over copper chromite[53]. The results showed that the selectivity of the unmodified nickel catalyst to FOL was much lower than that of the expected copper chromite, but the activity of the nickel catalyst in the gas phase was significantly higher, and the deactivation curves of the two catalysts were very similar, which may be due to the gradual formation of oligomeric/polymeric forms of products (or reactants) and their deoxygenation to hydrocarbons.
For the non-noble metal W catalyst, Ali et al. Studied the effect of different soft templates on the hydrothermal preparation of WO3 nanoparticles, and dodecyl dimethyl ammonium bromide (DAB) was used to adjust the size and shape of WO3 nanoparticles[54]. The conversion of FAL was 52% and the selectivity of FOL was 85% with D-WO3 as catalyst and water/ethanol as solvent at 100 ° C, 1 MPa H2 for 2 H.
The addition of a second metal dopant to a metal catalyst can improve its catalytic performance. In addition, the chemical composition, preparation method and reduction temperature of the catalyst precursor also have a great influence on the performance of the catalyst. In 2017, Wu et al. Synthesized efficient multifunctional CuNi alloy nanocatalysts using layered double hydroxides (LDHs) as catalyst precursors[55]. It was found that the FOL selectivity and FAL conversion of CuNi/MgAlO catalyst were more than 99% at 100 ℃ for 4 H under 4 MPa H2, and the bimetallic alloy nanocatalyst showed excellent stability and recyclability with complete substrate conversion in six runs. Li et al. Prepared multimetallic catalysts with good catalytic performance by pyrolysis method using ZIF as catalyst precursor[56]. It was found that the catalytic performance of NiCoZn @ CN-600 was the best at 2 MPa H2 and 160 ℃ for 4 H, the conversion of FAL was 100%, the selectivity of FOL was more than 99%, and it showed good cycle stability in five runs. Khromova et al. Prepared Ni-Cu-based catalyst with high metal loading by sol-gel method, and achieved 100% FOL selectivity with Ni-Cu alloy as catalyst and decanol as solvent at 130 ° C and 5 MPa H2[57]. On this basis, Sebin et al. Synthesized a Ni-Cu/ZrO2 catalyst with ZrO2 as the catalytic support for the hydrogenation of FAL, and the conversion of FAL was 99.7% and the yield of FOL was 93% with 7Ni-Cu/ZrO2 as the catalyst at 200 ° C and 1.5 MPa H2 for 4 H[58]. They tested the reusability of the catalyst after calcination and activation, but unfortunately, the catalytic activity of the catalyst continued to decline within five cycles. Subsequently, Weerachawanasak et al. Prepared bimetallic Ni-Cu/SiO2 catalyst by strong electrostatic adsorption combined with impregnation method with SiO2 as the catalytic support, which was used to catalyze FAL to FOL[59]. The conversion of FAL was 94% and the selectivity of FOL was 64% under the conditions of 2%Ni-5%Cu/SiO2 as catalyst, methanol as solvent, 100 ℃ and 2 MPa H2 for 2 H. By comparison, it was found that the catalytic performance of Ni-Cu alloy decreased slightly when SiO2 was used as the support. Singh et al. Did not study the effect of catalytic support, but found that the positive effect of solvent on improving selectivity was related to hydrogen bond donor and hydrogen bond acceptance. They synthesized Cu/Zn/XY catalyst by co-precipitation method under semi-batch reaction conditions.With water as solvent, the conversion of FAL and the selectivity of FOL were both more than 99% at 100 ℃ and 1 MPa H2 for 4 H, and the excellent catalytic performance was maintained within 5 cycles[60][60]. Babu et al. Prepared Cu-Cr-Zn mixed oxide catalysts by conventional and gamma radiation methods, respectively, to catalyze the gas-phase hydrogenation of FAL to FOL[61]. The results showed that the catalyst prepared by gamma radiation method exhibited higher hydrogenation activity compared with the conventional catalyst. The hydrogenation ability of the catalyst depends on the surface area, dispersion and Cr content of the Cu metal. Among them, the catalyst with a molar percentage of 0.4 in Cu/ZnO exhibited a FAL conversion of 84% and FOL selectivity up to 100%.
Although these catalysts can efficiently promote the hydrogenation of FAL to FOL under different catalytic systems, these reactions all use external H2 as hydrogen source. As we all know, at present, almost 96% of the H2 in industrial production comes from fossil resources, the cost of hydrogen production is high, and the gas is inconvenient to store and transport, so there are great potential safety hazards in the use process, and with the increasing depletion of fossil energy, it is urgent to develop new alternative hydrogen sources for industrial production.

2.1.2 Preparation of FOL from FAL catalyzed by alcohol as hydrogen source

Transfer hydrogenation using alcohols as hydrogen source involves the Meerwein-Ponndorf-Verley (MPV) reaction, in which aldehydes are reduced to the corresponding alcohols, while alcohols are usually oxidized to the corresponding aldehydes. The MPV reaction uses alcohols as hydrogen donors and is highly selective for carbonyl groups, so it has a wide range of applications in the selective reduction of unsaturated aldehydes and ketones[62]. At present, the alcohols used to prepare FOL by catalytic hydrogenation of FAL mainly include ethanol, 2-butanol, 2-propanol, etc. (See Table 3)[63][64][65,66]. The catalytic hydrogenation reactions using alcohols as hydrogen source are mainly liquid phase hydrogenation, and the corresponding alcohols are generally used as solvents and hydrogen donors. The catalysts are mainly non-precious metals, and the research on precious metal catalysts is less.
For noble metal ruthenium catalyst, in 2016, Gao et al. Catalyzed the reaction of FAL transfer hydrogenation (Catalytic transfer hydrogenation, CTH) to prepare FOL with benzyl alcohol as hydrogen donor and Co-Ru/C as catalyst. The selectivity of FOL was up to 100% and the yield was up to 98% at 150 ℃ for 12 H. This study confirmed the possibility of aromatic alcohols as hydrogen source, and the excellent Catalytic activity was still maintained in four cycles at 150 ℃ for 6 H[67]. Then, Wang et al. Used ethanol as hydrogen donor and solvent, and 6% Ru/mZrH as catalyst, the conversion of FAL was 92%, and the selectivity of FOL was 99% at 150 ℃[63]. Unlike other scholars, they explored the long-term stability of the catalyst and found that 6% Ru/mZrH was more stable than 6% Ru/ZrH before modification, but a small amount of Ru leaching and by-product deposition were still detected, resulting in catalyst deactivation.
For nickel-based catalyst, Wang et al. Prepared Ni-W/AC catalyst with activated carbon as catalytic carrier in 2018, and the FOL yield was only 25%[68]. On this basis, Fan et al. Successfully synthesized a Ni single-atom catalyst supported on nitrogen-doped carbon. With Ni-SAs/NC as the catalyst and 2-propanol as the hydrogen donor, the selectivity of FOL was as high as 97.1% and the conversion of FAL was 58.6% at 130 ℃ for 2 H. After four cycles, the catalytic activity was almost unchanged, showing excellent stability[69].
For the iron-based catalyst, Li et al. Also used nitrogen-doped carbon as the carrier to prepare the nitrogen-doped carbon supported iron-based catalyst Fe-L/C-800. With 2-butanol as the solvent and hydrogen donor, the FAL conversion was 91. 6% and the FOL selectivity was 83. 0% at 160 ℃ for 15 H, and there was no significant loss of catalytic activity in five runs[64]. Wang et al. Prepared a series of γ-Fe2O3@HAP as magnetic base catalysts by Hydroxyapatite (HAP) encapsulation coprecipitation method, using isopropanol as solvent and hydrogen donor, the conversion of FAL was 96.2% and the yield of FOL reached 91.7% at 180 ° C for 10 H, which could be reused for 6 times without loss of catalytic activity[70]. The catalytic performance is better than that of the former. Jiang et al. Prepared magnetic Fe3O4/C by pyrolytic carbonization and carbothermal reduction to catalyze FAL hydrogenation. Similarly, with isopropanol as solvent, the conversion of FAL was 76.4% and the selectivity of FOL was 98.5% at 2 MPa N2 and 200 ℃ for 4 H. After 4 reaction cycles, the conversion of FAL and the selectivity of FOL were almost unchanged, and the catalytic transfer hydrogenation activity was still high[71]. They found that Fe3O4 can act as a Lewis acid, thus favoring the catalytic transfer hydrogenation of FAL. Magnetic iron-based catalysts can generally achieve efficient recovery of catalysts without loss of catalytic activity.
Zr zeolite with abundant acid-base sites is an efficient catalyst in CTH reaction[64]. In addition, the simple and rapid separation characteristics of magnetic nanoparticles have attracted wide attention to the study of magnetic carriers loaded with active centers. Hou et al. Synthesized a hollow core-shell magnetic zirconia hydroxide catalyst with 2-propanol as the hydrogen donor and Zr @ Co-2 as the catalyst. The conversion of FAL could reach 93.9% and the selectivity of FOL could reach 97.3% at 160 ℃ for 4 H. After seven reaction cycles, the catalyst still maintained a high conversion of FAL of 91.1% and a selectivity of FOL of 97.8%[72]. At the same time, Li et al. Developed a series of magnetic zirconium catalysts using boron doping for the selective hydrogenation of FAL to FOL[73]. The FOL yield could reach 98. 7% by using Zr9B1FeO as catalyst, 2-propanol as hydrogen source and solvent at 170 ℃ for 2 H, and the catalyst still maintained good catalytic activity after five cycles. The acid-base sites of zirconium-based materials play a key role in the CTH formed by FOL[64]. Garcia-Sancho et Al. Synthesized ZrO2, Al2O3, and ZrO2/Al2O3 with different Zr/Al molar ratios to analyze the role of acid and base sites involved in the MPV process, and they found that the acid site played a dominant role in the catalytic activity[65]. When the Zr5Al5 was operated at 130 ℃ for 3 H, the conversion of FAL decreased gradually after each run in only four cycles, and the deactivation was caused by the formation of carbonaceous deposits on the catalyst surface.
For multimetallic catalysts, Kalong et al. Prepared a variety of non-precious metal catalysts of NiCuAl and CoCuAl by impregnation method, and with 2-propanol as hydrogen donor and CoCuAl as catalyst, the conversion of FAL can reach 100%, the selectivity of FOL is 63%, and the selectivity of 2-MF is 29% at 200 ℃ for 2 H[66]. And they found that the FAL conversion of all catalysts decreased significantly in three consecutive runs, indicating that deactivation was observed on all catalysts, and the reason may be that carbonaceous substances or heavy organic residues deposited on the surface of the catalyst during the reaction, thus blocking the active sites of the catalyst. In addition, compared with NiCuAl, the CoCuAl catalyst showed a weight loss of 1. 1%, showing lower catalyst deactivation and carbon deposition, but still had a deactivation phenomenon and was not stable enough. While for the rare earth metal lanthanum, Zheng et al. Constructed mesoporous ABO3 perovskite oxides with functionalized nanocrystal frameworks and abundant oxygen vacancies by the sol-assisted cation cooperative assembly method[74]. The conversion of FAL was more than 99% and the selectivity of FOL was more than 96% when oxygen-rich mesoporous LaMnO3 was used as catalyst at 180 ° C for 3 H. After five cycles, the catalyst exhibited excellent stability with almost no degradation in selectivity and conversion compared with the fresh catalyst. In addition, Nakanishi et al. Used TiO2 as a catalyst to photocatalyze FAL and 2-pentanol to prepare FOL, and the yield of FOL was 98% at room temperature for 0.5 H. It was found that the catalytic system had good catalytic activity for the preparation of FOL from hydrogen donors such as methanol, ethanol and isopropanol, and the catalyst could maintain stable performance after two times of use[75].
In recent years, more and more attention has been paid to the transfer hydrogenation of alcohols as liquid hydrogen source instead of external H2. As a hydrogen source, the alcohol can avoid introducing an external H2, and compared with the storage and transportation of the H2, the storage and transportation of the alcohol is more convenient, and the transfer hydrogenation reaction can eliminate the mass transfer resistance between the molecular H2 and a hydrogenation substrate and a solid catalyst, so that additional hydrogen delivery equipment is not needed, the overall process is simplified, and the economic benefit is improved.

2.2 One-pot preparation of FOL from xylose

Among the various routes of carbohydrate conversion, the conversion of xylose to FAL and the subsequent hydrogenation of FAL are considered to be one of the most promising routes in industry[76]. Fig. 3 shows the possible reaction path of xylose to FOL. It can be seen from the figure that the preparation of FOL from xylose is generally divided into two steps: xylose is first dehydrated under acid catalysis to obtain FAL; FAL is then hydrogenated to give FOL.
The production of FAL and the subsequent hydrogenation of FAL to produce FOL tend to be separate, thus requiring additional separation and transportation costs. In addition, the traditional production process of FAL from xylose dehydration generally requires a large amount of inorganic acid, while the production of FOL from FAL hydrogenation generally uses toxic Cu-Cr catalyst, which causes great pollution to the environment[77]. Therefore, many researchers have made many efforts to explore the one-pot catalytic production of FOL from xylose (see Table 4). Perez et al. Studied a dual catalyst system consisting of Pt/SiO2 and sulfated ZrO2 metal and acid catalysts[78]. Under this catalytic system, the conversion of xylose was 65% and the selectivity of FOL was 51% in water/2-propanol (1 ∶ 3) solvent system at 130 ℃ for 6 H, and the selectivity of FOL decreased gradually in two consecutive cycles, which may be due to the deactivation of acidic solid catalyst in the dual system.
In addition, they investigated a multifunctional catalyst based on sulfated zirconia for the one-pot preparation of FOL from xylose. They used Pt/ZrO2-SO4 (acid/metal = 142) as the catalyst and water/isopropanol (1:1) as the solvent system at 130 ° C and 3 MPa H2, the conversion of xylose was 32% and the selectivity of FOL was 27%, and they dried and recovered the catalyst after the reaction, and found that the catalytic performance of the catalyst after the reaction decreased slightly[79]. Subsequently, in another contribution, they evaluated the one-pot conversion of xylose in aqueous phase using multi-walled carbon nanotubes supported noble metals (ruthenium, platinum, gold, palladium, and rhodium) as catalysts. Firstly, Ru/MWCNT was used as catalyst, water ∶ 2-propanol (1 ∶ 1) as solvent, at 130 ℃, 3 MPa H2 for 6 H, the conversion of xylose was 100%, the yield of xylitol was 84%, and the yield of FOL was only 9%. Subsequently, they found that Pd and Rh had the highest selectivity for FOL, up to 20%, and a large number of functional surface groups could still be detected after dry characterization of the used catalysts, indicating that they had a certain stability under the operating conditions used in the xylose conversion process[80]. In addition, they also reported that the MPV reaction was accomplished over a metal-free catalyst (zeolite β) with water/isopropanol as the solvent, and the selectivity of FOL was up to 75%[81]. Perez et Al. Also studied the SBA-15 catalyst to catalyze xylose to FOL with aluminum as a heteroatom at different silica-alumina ratios ( [Al] -SBA-15)[82]. They found that changes in the surface of [Al] -SBA-15 altered the product distribution, with FOL being the dominant product. The selectivity of all the modified mesoporous catalysts to FOL was about 90%, and the catalysts were recycled three times with water/2-propanol (1 ∶ 1) as solvent at 130 ℃ for 4 H. It was found that the catalytic activity of the used catalysts was lost, which may be due to the decrease of the activity of Lewis acid sites during the recycling process. Canhaci et al. Converted xylose to FOL over a single organic-inorganic hybrid mesoporous silica supported catalyst[83]. They used Pt/SBA-15-SO3H with different acid/metal ratios as catalyst at 130 ° C for 6 H under 3 MPa H2, the conversion of xylose was 65%, and the selectivity of FOL was 83% – 87%. When they measured the reusability of the catalyst, they found that the catalytic activity decreased and the product distribution changed after each reaction cycle. Deng et al. Synthesized a bifunctional Cu/SBA-15-SO3H catalyst to catalyze xylose to FOL in a one-pot catalytic system[77]. The yield of FOL was 62. 6% under the optimum conditions of 4 MPa H2, 140 ℃ and 6 H with water/n-butanol as solvent. Tan Jingjing et al. Prepared Ru/sulfonated graphene metal-acid dual-site catalyst (Ru-SRGO) by introducing acidic site -SO3H and metal site Ru on the surface of graphene oxide, which was used to prepare FOL from xylose by one-pot method[84]. They used Ru-SRGO-2 as catalyst and 1,4-dioxane/water as solvent at 150 ° C under 1 MPa H2 for 4 H, the conversion of xylose was 100% and the selectivity was 70.4%. The conversion of xylose and the selectivity of the target product FOL did not change significantly after the catalyst was used repeatedly for 5 times, indicating that the catalyst had good stability.
Compared with the continuous fixed-bed reactor, the batch reactor for direct conversion of xylose faces the following problems. First, there is an equal probability that the xylose molecule will come into contact with the hydrogenation catalyst in addition to the acid catalyst. In this case, xylose is readily converted to xylitol by the hydrogenation catalyst, whereas xylitol is not convertible to FAL[85]. Second, batch reactors generally require longer reaction times than continuous reactors, which will inevitably promote side reactions between xylose, xylose dehydration intermediates, and FOL. These problems will lead to the complexity of the product, and the yield of the target product will be greatly reduced[86].
Cui et al. Used a continuous fixed-bed reactor to synthesize FOL and 2-MF with Hβ zeolite and Cu/ZnO/Al2O3 as catalysts, γ-butyrolactone (GBL)/water as solvent, and xylose as substrate[87]. It was found that the synergistic effect of Hβ zeolite and GBL promoted the dehydration of xylose and greatly increased the yield of FAL. Moreover, the Hβ zeolite passivated by the carbon deposit can be recovered by reactivation in air, and the recovered Hβ zeolite also achieves high activity in xylose dehydration. In addition, by changing the hydrogenation temperature of FAL over Cu/ZnO/Al2O3 catalyst, the yield of FOL and 2-MF could be adjusted to 87.2% at 150 ° C for FOL and 86.8% at 190 ° C for 2-MF.
In the traditional process of preparing FOL from xylose, FAL is obtained by dehydration of H2SO4, and FOL is prepared by using noble metal as catalyst and H2 as hydrogen source. This process not only increases the cost, but also complicates the operation[88]. Xu et al. Used formic acid as a catalyst and hydrogen donor for xylose dehydration with a mesoporous nitrogen-doped carbon-limited cobalt catalyst (Co-C-N) at 160 ° C for 3 H to obtain a FOL yield of 69.5%, and observed high stability of the Co-C-N catalyst for xylose conversion after five reuse cycles[88].
The preparation of FOL from xylose by chemical catalysis has some limitations. In recent years, some progress has been made in the preparation of FOL from xylose by the combination of biocatalysis and chemical catalysis. He et al. Catalyzed a xylose-rich hydrolysate to produce FOL using SO42-/SnO2 and Escherichia coli strains such as CCZU-A13, CCTU-T15, and CCZU-K14 as catalysts[89,90][91][89][90]. They used a biocompatible solid acid catalyst (SO42-/SnO2-APG) and E. Coli CCZU-A13 to dehydrate xylose and catalyze FAL to FOL, respectively. After reaction at 170 ℃ for 20 min, the pH value of the solution was adjusted, and E. coli CCZU-A13 cells containing reductase SsCR were added. After reaction for 3 H, the conversion rate of xylose was 100%, and the yield of FOL was 44%. After 5 cycles, only 7% of the catalytic activity was lost, which indicated that the prepared solid acid catalyst and immobilized cells were relatively stable[91]. Xylose can also be converted into FOL in toluene/water medium by one-pot tandem reaction using SO42-/SnO2-kaolin and recombinant Escherichia coli CCZU-T15 as catalysts[89]. With SO42-/SnO2-kaolin as catalyst, the yield of FAL was 74.3% at 170 ℃ for 0.5 H. Next, E. Coli CCZU-T15 was used as a biocatalyst to convert FAL to FOL, and the yield of FOL was 13%[89]. In addition, they studied the preparation of FOL in a tandem reaction using SO42-/SnO2-Montmorillonite and Escherichia coli CCZU-K14 as catalysts[90]. A FAL yield of 41.9% was obtained at 170 ° C for 20 min. In addition, 100% FOL yield was obtained in whole cells of E. Coli CCZU-K14 at 30 ° C, pH 6.5 and 1.5 mol glucose/mol FAL within 24 H[90]. Li et al. Used carbon nanotubes (CNTs) to synthesize tin-loaded sulfonated carbon nanotubes (SO42-/SnO2-CNT), which were used to catalyze the production of FOL from xylose[92]; The yield of FAL could reach 41. 9% – 61.2% with SO42-/SnO2-CNT as catalyst and cyclopentyl methyl ether (CPME)/water as solvent at 180 ℃ for 15 min. In order to explore the reusability of the catalyst, the catalyst was recovered and reused for 5 times, and it was observed that the FAL yield decreased slightly after each cycle, showing a good stable recovery ability. Then the recombinant E. coli CG-19 expressing reductase was used as biocatalyst to catalyze FAL to FOL at 35 ℃ and pH 7. 5, and the yield of FOL could reach 32. 7% ~ 61.2%.
The one-pot conversion of xylose to FOL can not only reduce pollution, but also reduce the cost of separation and transportation, but the selectivity and yield of the product are generally not high, and there is still a certain distance from the practical application of FOL production.

2.3 Fructose one-pot preparation of FOL

FOL is currently prepared by hydrogenation of C5 carbohydrate dehydration, but the hydrogenation reaction requires additional H2 as a hydrogen source or a non- H2 source as a hydrogen donor[78]. However, in nature, cellulose accounts for the highest proportion of lignocellulose, so C6 carbohydrates are extremely abundant in nature. Therefore, the conversion of hexose to FOL by tandem dehydration and decarbonylation provides an excellent alternative strategy for the preparation of FOL. With the increasing interest in "one-pot" reactions, the direct conversion of monosaccharides to furan derivatives using multifunctional catalysts or catalyst combinations in batch or fixed-bed reactors has been extensively studied. However, the one-step conversion of fructose to FOL in a continuous fixed-bed reactor has received little attention[93]. Dai et al. Used AlCl3·6H2O/Pd(OAc)2 as a combined catalyst to deoxidize fructose into FOL by tandem dehydration and decarbonylation in one pot at 150 ° C for 4 H. The conversion of fructose was 100% and the yield of FAL was 40.6%[94]. It was found that AlCl3·6H2O acts as an efficient Lewis acid to catalyze the dehydration of fructose to HMF, and subsequently, Pd(OAc)2 catalyzes the removal of the C = O moiety from HMF to selectively produce FOL. In addition, they found that 1-vinyl-2-pyrrolidinone (PVP) could stabilize the hydroxyl group on the HMF intermediate through intermolecular hydrogen bonding, accelerate the dehydration of fructose, improve the deoxygenation efficiency, and finally obtain a FOL yield of 40.6%. Wang et al. Explored a tandem catalytic method combining zeolite and palladium-based catalyst to convert fructose directly into FOL[26]. The study pointed out that the dehydration of fructose on HY zeolite could effectively achieve decarbonylation on the Pd/Al2O3 catalyst. At 160 ℃ and 3%H2/N2, the selectivity of FOL reached the highest, and the yield of FOL was 41.6%. They also found that the product selectivity of the catalyst did not decrease significantly after 40 H of continuous reaction, indicating that this tandem catalytic system could stably convert fructose into FOL.

3 Conclusion and prospect

With the increasing shortage of fossil energy, the use of platform compounds derived from renewable woody biomass resources to produce high value-added products has become the most effective way to deal with the current resource and energy crisis. The development of green and efficient processes for converting biomass resources into high value-added chemicals is one of the important directions to achieve sustainable development. As far as the current research technology is concerned, the catalytic hydrogenation of FAL to FOL is still the most efficient way. Through the selection of catalysts, the product selectivity and yield can reach more than 99%, and the catalyst has good cycle stability. Moreover, many scholars are still committed to exploring high-performance catalytic systems, so the catalytic hydrogenation of FAL to FOL is still a hot research direction. In addition, in recent years, it has been found that the one-pot preparation of FOL from xylose can not only reduce pollution, but also reduce the cost of separation and transportation in the whole process. Although the research efforts are constantly strengthened, the product yield is still unsatisfactory, and the cycle stability of the catalyst is not ideal. In addition, there are few reports on the preparation of FOL from fructose, glucose and hemicellulose.
In order to achieve the goal of more green, efficient and economical conversion of raw materials into FOL, the following breakthroughs are suggested in future research: (1) Innovative catalytic system. The combination of biocatalysis and chemical catalysis, such as the combination of reducing bacteria and solid acid catalysts, is gradually adopted. (2) Innovating one-pot catalytic system and solvent system, such as water/n-butanol two-phase solvent system, to continuously simplify the production process, reduce production costs, and increase the possibility of industrial production applications. (3) Innovative hydrogen donor system, in addition to the traditional H2 molecules and solvent systems such as alcohols, formic acid and water, try to innovatively use ionic liquid system, eutectic solvent system and its multi-solvent system combination for transfer hydrogenation. (4) Strengthen the research on the formation mechanism and reaction kinetics of FOL, and constantly optimize the reaction conditions, so as to lay a foundation for the large-scale industrial production of new catalysts.

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Funding

National Natural Science Foundation of China(22108038)

Tianjin University-Fuzhou University Independent Innovation Fund Cooperation Project(TF2022-10)

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