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Hydrodeoxygenation of Lignin and its Derivatives to Liquid Hydrogen Storage Materials

Nian Qu , Yonghui Ling , Xuehui Li , Zhengjian Chen , Jinxing Long

Progress in Chemistry ›› 2026, Vol. 38 ›› Issue (4) : 661 -671.

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Progress in Chemistry ›› 2026, Vol. 38 ›› Issue (4) : 661-671 DOI: 10.7536/PC20250631
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Hydrodeoxygenation of Lignin and its Derivatives to Liquid Hydrogen Storage Materials
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Abstract

Novel and efficient techniques for low-cost and environmentally-friendly energy storage systems are imminent， in regard to the excessive consumption of non-renewable fossil energy. Hydrogen shows the advantages of high energy density， carbon neutrality and pollution-free， so it has been considered as a promising energy carrier to replace fossil fuels. However， the practical application of hydrogen is challenged by the low density， difficult storage and transportation. Therefore， efficient hydrogen storage materials for hydrogen are of great significance. Liquid organic hydrogen carriers （LOHCs） promote the release and absorption of hydrogen through chemical reactions， so it has attracted increasing attention. Lignin is the most abundant aromatic source of natural， renewable organic carbon on Earth. The technologies of converting lignin into LOHCs through catalytic upgrading meet the demands of "carbon neutrality" and have huge application potential. Therefore， we summarized here the recent research progress in the hydrodeoxygenation of lignin and its derivatives to LOHCs. The effects of different catalyst carriers on the catalytic performance for producing LOHCs were demonstrated. The application of the saturated products from lignin and its derivatives， which are considered to be promising LOHCs， was also reviewed. In addition， we also provided a prospect on the future technical development of the production of liquid hydrogen storage materials from lignin and its derivatives.

Contents

1 Introduction

2 LOHCs

2.1 Aromatic compounds

2.2 Dehydrogenation and hydrogenation of liquid hydrogen storage materials

3 Influence of catalyst carriers on the performance of lignin-based liquid hydrogen storage materials production

3.1 Carbon material

3.2 Metallic oxide

3.3 Molecular sieve

4 Conclusion and outlook

Graphical abstract

Keywords

hydrogen energy / liquid organic hydrogen carrier / lignin / hydrodeoxygenation / heterogeneous catalyst

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Nian Qu, Yonghui Ling, Xuehui Li, Zhengjian Chen, Jinxing Long. Hydrodeoxygenation of Lignin and its Derivatives to Liquid Hydrogen Storage Materials. Progress in Chemistry, 2026, 38(4): 661-671 DOI:10.7536/PC20250631

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1 Introduction

The technological revolution based on fossil fuels has promoted the rapid development of human civilization[1], but the large-scale use of non-renewable fossil resources such as coal, oil, and natural gas has led to massive emissions of carbon dioxide and other pollutants, triggering a series of ecological and environmental problems including global warming and widespread smog[2-4]. To avoid the depletion of natural resources and environmental pollution, and to respond to the national "Dual Carbon" policy[5], there is an urgent need to develop efficient, low-cost, and environmentally friendly energy storage systems[6]. Hydrogen, with its advantages of high energy density, carbon neutrality, and zero pollution, is a promising energy carrier to replace fossil fuels; however, its storage and transportation remain bottlenecks for practical applications, making it essential to find suitable hydrogen storage materials[7-8]. Currently, hydrogen storage methods are mainly divided into physical storage and chemical storage (Figure 1)[9]. Physical storage mainly involves compressing or cooling and liquefying hydrogen for storage and transportation; this method imposes high requirements on hydrogen storage equipment and process safety. Chemical storage refers to storing hydrogen in matrix materials through chemical adsorption or chemical reactions. Based on the storage and release mechanisms of hydrogen in matrix materials, chemical storage materials can be classified into irreversible and reversible hydrogen storage materials. Irreversible hydrogen storage materials undergo permanent changes in their chemical structure during dehydrogenation and cannot be restored to their original state through simple re-hydrogenation, such as borohydrides and aluminohydrides. In contrast, reversible hydrogen storage materials can repeatedly adsorb and desorb hydrogen under specific temperature and pressure conditions while maintaining basic stability of their chemical structure, examples include aromatic compounds and MOFs. Relatively speaking, reversible hydrogen storage materials offer advantages such as cyclic stability, milder operating conditions, and higher safety[9]; if hydrogen storage materials can be recycled and re-hydrogenated, it will reduce costs while enabling broader application of hydrogen storage technology.
In material-based storage methods, compared to other hydrogen storage materials (Figure 2)[10], liquid organic hydrogen carriers (LOHCs) have a hydrogen storage capacity of 5~8 wt%, offering advantages such as reversibility, moderate dehydrogenation temperatures, commercial availability, and compatibility with existing gasoline infrastructure. LOHCs facilitate hydrogen release and absorption through chemical reactions, demonstrating significant advantages in hydrogen storage and energy applications. In a broader sense, any chemical substance that exists in the liquid phase during use and has a hydrogen-lean form and a hydrogen-rich counterpart can serve as an LOHC, such as isopropanol, cyclohexanol, and cyclohexane.[11-12], among which cyclohexane has a high hydrogen storage capacity (7.2 wt%), and methylcyclohexane also has a high hydrogen storage capacity (6.1 wt%), far exceeding the target set by the U.S. Department of Energy for on-board hydrogen storage (5.5 wt%). They have become promising hydrogen storage materials for on-board and large-scale long-distance hydrogen transport. Therefore, from the perspective of practical application and sustainability, developing the conversion of widely available natural resources such as biomass into alkyl cycloalkanes, C6+cycloalkanols, aromatic compounds, and other LOHCs holds great development prospects.
Biomass is the most abundant natural renewable organic carbon source, primarily composed of three components (cellulose, hemicellulose, and lignin)[13], and is considered a promising candidate with advantages such as availability and carbon neutrality[14]. Taking lignin as an example, it is a natural polymer material mainly composed of syringyl (S), guaiacyl (G), and p-hydroxyphenyl (H) units linked by C―O and C―C bonds, along with their corresponding derived structural units (Figure 3), accounting for 15%~30% of the mass and about 40% of the energy of lignocellulosic biomass[15-16]. Through thermochemical conversion, lignin depolymerization products can be further hydrodeoxygenated to generate aromatic compounds, biofuels, light aromatics, etc.[17-18]. Theoretically, these compounds can be used for hydrogen storage and release through reversible reactions and can be transported as LOHCs[19].
Therefore, as a hydrogen storage energy carrier with characteristics such as carbon neutrality and renewability, lignin holds immense development potential for deriving renewable LOHCs. Based on this, this paper summarizes typical lignin-based LOHCs and their hydrogen storage mechanisms, and systematically elaborates on the influence of catalyst supports on the performance of producing LOHCs via hydrodeoxygenation of lignin and its derivatives.

2 Liquid Organic Hydrogen Carriers (LOHCs)

Currently, the most commonly used hydrogen storage materials include liquid organic hydrogen carriers (LOHCs), liquid ammonia hydrogen storage (LAH2), and carbon-based hydrogen storage (CMH2)[20]. Among these, LOHC technology uses unsaturated liquid organic compounds as hydrogen storage agents and their corresponding saturated forms as hydrogen carriers. Their reversible catalytic hydrogenation reactions enable them to store and release hydrogen; therefore, LOHCs are a promising hydrogen storage material with good development prospects.[21]. For example, in the benzene/cyclohexane hydrogen storage system, which was the earliest to be studied, benzene and hydrogen are introduced into a reactor under a pressure of 4 MPa and a temperature of 150 °C during catalytic hydrogenation to produce saturated cyclohexane. During this reaction, approximately 68.8 kJ/mol of energy is released. At 300 °C and 0.1 MPa hydrogen pressure, cyclohexane absorbs approximately 68.8 kJ/mol of energy, gradually releasing hydrogen and ultimately dehydrogenating back into benzene.[22].

2.1 Aromatic compounds

Ideally, LOHCs will offer the advantages of high safety, high purity, low cost, ease of transport, and reversibility, while being compatible with existing fossil fuel infrastructure as liquid energy carriers[23]. First, for current transportation systems, the liquid state is more suitable for storage and transport; second, organic compounds have relatively high hydrogen storage capacities, and the hydrogen release process can proceed at high dehydrogenation rates under mild operating temperatures and in the presence of catalysts[7]. According to previous studies, organic liquid hydrogen carriers are generally aromatic compounds or N-doped compounds (Figure 4)[24]; compared to other organic molecules, the aromatic rings possessed by aromatic compounds exhibit unique resonance interactions, making them more prone to hydrogenation and dehydrogenation reactions. Most aromatic compounds are derived from the cracking of fossil energy sources, but traditional fossil energy reserves are limited and non-renewable. Biomass, as the only renewable carbon resource in nature, yields depolymerization products including high-value chemicals such as monophenols and biofuels like alcohols, which can also serve as one of the sources for organic liquid hydrogen carriers[19].

2.2 Dehydrogenation and Hydrogenation of Liquid Hydrogen Storage Materials

For LOHCs, the hydrogenation and dehydrogenation processes are crucial for their development. To accelerate these hydrogenation/dehydrogenation processes, catalysts must be added to the reaction system to reduce activation energy while increasing the reaction rate.[25]. Researchers have extensively studied noble metals such as palladium, platinum, and ruthenium, as well as transition metals like nickel and cobalt, for applications in hydrogenation/dehydrogenation. Multimetallic catalysts have also been explored for their potential to improve reaction rates, selectivity, and durability.[26]. To date, most relevant catalysts possess a single function, meaning they can be used for either hydrogenation or dehydrogenation, but not both simultaneously.[27]. Cycloalkanes offer advantages including relatively high hydrogen capacity (6~8 wt%), liquid state at room temperature, high boiling points, production of CO-freexhydrogen, and low toxicity. Methylcyclohexane, with its methyl side chain, undergoes dehydrogenation more readily than cyclohexane and has been proposed and studied as a liquid hydrogen carrier.[28], while Pt-based catalysts have been confirmed to exhibit excellent catalytic performance in dehydrogenation reactions. Wang et al.[29]prepared Pt/Ce-Mg-Al layered double hydroxides with varying Ce content via a one-step precipitation method. After calcination and reduction, Pt/Ce-Mg-Al-O catalysts were obtained. The results showed that on the Pt/Ce14-Mg-Al-O-350 catalyst, the only liquid dehydrogenation product of methylcyclohexane was toluene, with a selectivity exceeding 99.9%. At 350 °C, the conversion rate and hydrogen release rate reached 98.5% and 1358.6 mmol/gPt/min, respectively. This is because the addition of CeO2promoted Pt dispersion and reduced Pt particle size, thereby improving dehydrogenation efficiency. Furthermore, this catalyst exhibits strong coking resistance and good stability, indicating significant potential for industrial applications. Recently, it was discovered that oxygen vacancies near Pt atomic sites can promote the adsorption of cyclic molecules and drive stepwise dehydrogenation reactions via ultra-synergistic effects involving redox coupling between Pt and Ce atoms. Chen et al.[30]found that reaction sites composed of single Pt atoms and adjacent oxygen vacancies (VO) could be used to prepare CeO2(Pt1/CeO2</sub>/molPt/h, which is 309 times that of traditional supported Pt nanoparticles. Through a series of characterizations and experiments with model compounds, the dehydrogenation reaction pathway of cyclohexane on this catalyst was determined as follows (Figure 5).
In addition to Pt, scholars have explored the influence of different metal active centers on dehydrogenation performance, finding that their initial catalytic activity for dehydrogenation reactions follows the order Pd > Pt > Ru > Rh[31]. Ge et al.[32]prepared two-dimensional magnesium hydroxide nanosheets supported Pd for the dehydrogenation of dodecahydro-N-ethylcarbazole. When the metal loading was 0.5 wt%, the substrate conversion rate of this catalyst was 100%, and the hydrogen release amount was 5.7 wt%; under the same conditions, the hydrogen release amount of the Pd/MgO catalyst was only 2.3 wt%, with a conversion rate of 71.0%. The research results indicate that catalysts prepared using magnesium hydroxide nanosheets as supports can be effectively used for the dehydrogenation of nitrogen-containing aromatics. Studies have shown that, in addition to single-metal catalysts with single functionality, bimetallic nanocatalysts can be simultaneously used for both hydrogenation and dehydrogenation reactions of LOHCs[33]. Zhu et al.[34]prepared Ru-Pd/Al2O3 catalysts via an impregnation-hydrogen reduction method and applied them to the complete hydrogenation of N-propylcarbazole and the dehydrogenation of the hydrogenated products. The results demonstrated that the Ru-Pd/Al2O3 catalyst possesses excellent hydrogenation and dehydrogenation activity, along with good selectivity and stability. This is due to the positive synergistic effect between palladium and ruthenium nanoparticles, which enhances the activity of the Ru-Pd/Al2O3 catalyst.

3 Effect of catalyst support on lignin depolymerization for LOHCs preparation

Currently, in the reaction of lignin conversion to prepare LOHCs, different types of catalysts exhibit distinct characteristics, among which heterogeneous catalysts are the most widely applied. Heterogeneous catalysts are divided into unsupported catalysts and supported catalysts[35]. Unsupported catalysts refer to those where the active component itself serves as the catalyst without relying on other supports, mainly including metals, metal oxides, and solid acids/bases. Supported catalysts generally consist of active centers, promoters, and supports. The active center primarily facilitates the catalytic reaction; the promoter mainly enhances the activity, selectivity, or stability of the active center; and the support primarily provides physical support, increases specific surface area, improves the dispersion of active centers, and enhances thermal stability. Supported catalysts improve the utilization efficiency of expensive or scarce active components and enhance the necessary mechanical strength and stability of the catalyst, thereby reducing costs and achieving large-scale, long-term stable operation[36]. Therefore, supported catalysts are more widely used in lignin depolymerization. For supported catalysts, selecting an appropriate support to catalyze lignin conversion is key to improving their catalytic efficiency.
Therefore, this article reviews the application of supported catalysts in the lignin depolymerization process based on different supports, mainly categorized into carbon materials, metal oxides, and molecular sieves. Different catalysts can be applied to different stages of the depolymerization process to improve efficiency and produce desired products. In the lignin depolymerization process, these catalysts each have their own advantages and disadvantages; for example, carbon materials can efficiently cleave C—C bonds in lignin but suffer from the drawback of easy coking.[37]; metal oxides can provide acid/base sites for synergistic catalysis but suffer from the drawback of irreversible sintering.[38]; molecular sieves possess shape selectivity but suffer from the drawback of pore blockage leading to deactivation.[39], there are also studies focusing on composite supports to enable them to simultaneously possess the advantages of two types of supports, with specific comparisons as shown inTable 1.

3.1 Carbon materials

Carbon materials possess advantages such as wide availability, well-developed pore structures, large specific surface areas, and strong adsorption capacities, and have been widely applied in various fields including batteries, adsorption, detection, and catalysis.[40]. Lignin features characteristics such as high molecular weight and complex spatial structure; matching carrier pore structures can improve lignin depolymerization efficiency. Furthermore, physical and chemical treatments of carbon materials can adjust their pore structures, specific surface areas, and other properties. Therefore, carbon materials are commonly used as catalyst supports in research on catalytic lignin hydrogenolysis.[41]. Common categories of carbon materials include activated carbon[42-43], carbon nanotubes[44-45], metal-organic frameworks[46-47], etc.

3.1.1 Activated Carbon

Activated carbon is a type of carbon prepared by special treatment of organic raw materials through carbonization and physical or chemical activation. It features wide sources, well-developed pore structure, large specific surface area, and strong adsorption capacity, making it the most common carbon material.[33]. Activated carbon can not only load noble metals such as Ru and Pd, but also combine with transition metals like Ni and Fe to achieve excellent catalytic activity.[48]. Gao et al.[49]prepared high-performance activated carbon-supported ruthenium-based catalysts (Ru/AC) via the impregnation method. The results showed that on the 5% Ru/AC catalyst, lignin-derived phenolic compounds could be hydrogenated to produce cycloalkanols and cycloalkanes, exhibiting good effectiveness for the selective cleavage of C—O bonds. By using diphenyl ether as a substrate, they studied the conversion reaction pathway of diphenyl ether at 180 °C and 2 MPa H2 (Figure 6), finding that the catalyst possesses not only high aromatic ring hydrogenation activity but also the ability to cleave C—O bonds, providing a new pathway for converting lignin into high-value biofuels and chemicals. Long et al.[15]proposed the synergistic catalysis of lignin in situ hydrocracking using Ru/C and NaOH. The results indicated a lignin conversion rate as high as 92.5%, yielding 12.69% phenolic monomers and 6.12% aliphatic alcohols.
Furthermore, introducing Ni as a second metal component in activated carbon-supported noble metal catalysts is an effective method to reduce the noble metal content in the catalyst composition. Jin et al.[50]proposed a method for preparing cyclohexanol by combining aqueous phase reforming and hydrodeoxygenation of guaiacol using a Ni-Pt/AC bimetallic catalyst. The results showed that when the Pt loading increased from 0.5% to 1%, the selectivity of the Ni-Pt/AC catalyst towards cyclohexanol significantly improved. In addition, Pt can inhibit the oxidation of Ni and slow down the sintering of Ni-Pt, thereby enhancing the stability of the catalyst.

3.1.2 Carbon nanotubes

Carbon nanotubes are graphene sheets rolled into cylindrical shapes, classified into single-walled carbon nanotubes and multi-walled carbon nanotubes. Carbon nanotubes possess a large surface area, good electrochemical activity, and unique metal support capabilities, making them a catalyst support with immense development potential.[51]. Xiao et al.[52]prepared a nanostructured MoOx/CNT catalyst for the hydrogenolysis of enzymatic lignin. The results showed that under optimal reaction conditions, the catalyst exhibited high selectivity towards phenolic compounds, achieving a monomeric phenol yield of up to 47 wt%. This is because, under an H2 atmosphere, the cleavage of β-O-4 bonds takes precedence over the addition of double bonds. Studies have indicated that rare earth metals such as cerium and lanthanum exhibit excellent catalytic performance in the hydrogenolysis of lignin and its derivatives.[53]. Ma et al.[54]prepared a series of rare earth metal catalysts supported on carbon nanotubes for the catalytic depolymerization of lignin. The results showed that under reaction conditions of 260 °C for 1 h, the Ce/CNT catalyst achieved a lignin liquefaction rate of 86.1%. Furthermore, the catalyst maintained high activity after four recycling runs, with the liquid product yield remaining at 82.0%.
Reports indicate that carbon nanotubes can serve not only as supports for supported catalysts but also as supports for confined catalysts (Figure 7)[55]. Confined catalysts enhance the activity and selectivity of catalysts by controlling nanoscale active sites within their channels, which strengthens the electronic interaction between the active centers and the inner surface of the carbon nanotubes compared to supported catalysts. Furthermore, the confinement effect of confined catalysts enriches reactants within the cavities of the carbon nanotubes, thereby further promoting reactant conversion.

3.1.3 Metal-Organic Frameworks

Metal-organic frameworks (MOFs) are a class of novel porous polymer materials formed by connecting inorganic metal ions/clusters and organic ligands through coordination bonds. In recent years, MOFs and their derived materials have attracted widespread attention due to their excellent properties.[56]. Mei et al.[57]prepared Ni/C catalysts using Ni-MOF as a precursor and investigated the effects of catalyst calcination temperature and reaction conditions on catalytic performance. It was found that catalyst performance is significantly influenced by calcination temperature, with the catalyst calcined at 500 °C exhibiting the best performance, efficiently cracking various lignin model compounds and natural lignin into monomers with high yields. The molecular structure of lignin contains abundant active functional groups that can coordinate with various metal ions to form metal-biopolymer hybrid materials.[58]; therefore, some studies have also used lignin as a carbon source to prepare MOF-derived catalysts. Su et al.[59]used lignosulfonate as a carbon source, incorporated it into the MOF structure, and prepared catalysts with different Ni/Co metal ratios via a hydrothermal method. Under optimal conditions, 5-hydroxymethylfurfural was converted to 5-methylfurfuryl alcohol with high selectivity. The catalyst preparation process using lignin as a carbon source not only provides a new pathway for the high-value utilization of biomass resources but also demonstrates good catalytic performance and promising application prospects. Ge et al.[60]used lignin as a carbon source and metal-organic frameworks (MOFs) as structure-directing agents to synthesize a series of cobalt-based catalysts via a hydrothermal method (Figure 8). Under the optimal reaction conditions of 240 °C, 0 MPa N2, and 4 h, the guaiacol conversion rate reached 100%, and the cyclohexanol yield reached 90%. Furthermore, it was found that the catalyst maintained high activity after five cycles under optimal conditions, indicating good stability.

3.1.4 Nitrogen-doped carbon materials

Doping carbon materials with other elements is a common method for modifying carbon materials, which can effectively alter their chemical properties and functionality.[61]Introducing nitrogen atoms into the carbon lattice can promote interactions between the carbon structure and metal particles, enhancing the dispersion of active metals with high thermal aggregation and leaching stability. Furthermore, nitrogen doping alters the acid-base properties of the support surface, improving the catalytic activity of the catalyst, thus holding broad application prospects in various catalytic processes.[62]. Yang et al.[63]reported a simple method for the in-situ preparation of Ru@NC catalysts (Figure 9). This method prepares the catalyst by direct pyrolysis of a mixture of ruthenium and urea loaded on activated carbon. The results show that the prepared Ru@NC-800 catalyst possesses a high specific surface area and graphitic structure, exhibiting excellent catalytic activity and selectivity for the HDO reaction of vanillin under mild conditions.
Apart from noble metals, non-noble metals are also frequently used as active metals in catalytic hydrogenation to reduce economic costs[64]. Wang et al.[65]prepared highly active nickel nanoparticle catalysts on defective nitrogen-doped carbon supports using molten amine as a soft template. The results showed that under mild conditions, most representative lignin model compounds were converted into aromatic monomers with 100% conversion, and the nitrogen-doped catalyst exhibited higher activity than the non-nitrogen-doped catalyst. Wu et al.[66]prepared a lignin-MOF derivative N-doped support loaded with Co catalyst via a one-step hydrothermal method and applied it to the modification of lignin-derived phenols and lignin depolymerization. The results indicated that under optimal conditions (180 °C, 0.5 MPa N2, 2 h), the conversion rate of vanillin was 100%, and the yield of 2-methoxy-4-methylphenol reached a maximum of 92%. This is because N doping induced strong electronic interactions between cobalt nanoparticles, thereby increasing the number of surface active sites on cobalt. Based on the structural characterization of the catalyst and the hydrodeoxygenation reaction results, the authors proposed a mechanism for the hydrodeoxygenation process of vanillin (Figure 10).
In addition to nitrogen doping, other heteroatoms such as O are often incorporated into carbon materials[67], S[68], etc., and oxygen-containing groups on the surface of carbon materials facilitate hydrodeoxygenation reactions[69]. Mo et al.[70]used benzylamine and catechol as nitrogen and oxygen sources to synthesize a polymer via alkylation, followed by in situ pyrolytic reduction and H2O2post-treatment to prepare a Pd/Ni alloy-supported N,O co-doped porous carbon bimetallic catalyst. The results showed that under optimal reaction conditions, the conversion of vanillin was 98.3%, the selectivity to 4-methylguaiacol was 99.1%, and the catalyst maintained good catalytic performance after seven cycles.

3.2 Metal oxide

Metal oxides have broad application value in the field of catalysis and are commonly used as main catalysts, co-catalysts, or supports for lignin depolymerization[62]. Different metal oxides exhibit distinct catalytic properties in lignin hydrogenolysis; common metal oxides include Al2O3[71], TiO2[72], ZrO2[73], MgO[74-75], etc. Among them, Al2O3possesses acidity that can effectively promote bond cleavage and ring opening of lignin. Different preparation conditions can yield alumina with various morphologies, among which γ-Al2O3is the most common catalyst support morphology. It features tunable pore size distributions (2~50 nm), which facilitate mass transfer of large lignin molecules, and has been extensively studied in lignin hydrogenolysis[76]. Liu et al.[77]prepared a series of palladium-based catalysts and applied them to the hydrogenation of various lignin-derived phenols and dimers. The results showed that the 2.0 wt% Pd/γ-Al2O3catalyst exhibited the best performance. Under optimized reaction conditions, the substrate conversion reached 100%, and the yield of cyclohexanol was 94.9%. TiO2offers multiple advantages such as high catalytic activity, low cost, and non-toxicity, and is also widely used as a catalyst support in lignin hydrogenolysis. For instance, Dou et al.[78]conducted self-hydrogen-transfer hydrogenolysis of native lignin over a Pd-PdO/TiO2catalyst. At 180 °C without an external hydrogen source, the catalyst converted poplar lignin into lignin monomers with a 40 wt% yield. A series of experiments with model compounds demonstrated (Figure 11) that in this reaction, Pd acts as a dehydrogenation center while PdO activates C—O bonds. The coexistence of Pd and PdO promotes the cleavage of β—O—4 and C—O bonds. Furthermore, MgO possesses strong basicity, which favors the further hydrogenation of lignin-derived phenols. Long et al.[79]constructed a CuxNiy/MgO catalytic system, achieving yields of 88.6% for ethylbenzene and 98.3% for cyclohexanol from lignin dimers, and obtained colorless fuel with high heating value from lignin bio-oil. They proposed that basic MgO can effectively inhibit the re-condensation of phenolic products.
Mixed metal oxides have been proven to effectively prevent product recombination, suppress coke formation, improve lignin conversion rates, and extend catalyst lifespan. For example, we[80]constructed a Cu-Ni/MgCrOxcatalyst system that, by balancing the acidity and basicity of Ni0, Cu+, as well as MgO and MgCr2O4, achieved hydrogenolysis of lignin to obtain alcohols. Under optimal reaction conditions, Cu6Ni20/MgCr0.5Oxcatalyzed lignin conversion, achieving a monomer yield of 30.1%, with a selectivity of 59.5% and a yield of 17.9% for 4-ethylcyclohexanol. Furthermore, CeO2-supported Al2O3possesses both the high specific surface area of Al2O3and the ability of CeO2to improve the dispersion and reactivity of surface metals, among other benefits[81]. Xiu et al.[82]prepared Ni-Fe/CeO bimetallic catalysts with different Ni-Fe ratios via chemical reduction. The results showed that under optimal process conditions, the maximum bio-oil yield was 67.14 wt%; the maximum quantitative yield of phenolic monomers was 8.77 wt%. In an isopropanol reaction system using formic acid as an internal hydrogen donor, with a Ni-to-Fe mass ratio of 1:1, a depolymerization temperature of 240 °C, and a depolymerization time of 8 h, the depolymerization products of lignin reached 95%. Shu et al.2-Al2O3bimetallic catalysts, the results indicated that under optimal process conditions, the maximum bio-oil yield was 67.14 wt%; the maximum quantitative yield of phenolic monomers was 8.77 wt%. In an isopropanol reaction system using formic acid as an internal hydrogen donor, with a Ni-to-Fe mass ratio of 1:1, a depolymerization temperature of 240 °C, and a depolymerization time of 8 h, the depolymerization products of lignin reached 95%. Shu et al.[83]introduced MoO3intoγ-Ni/ZrO2, which altered both the phase of ZrO2and the acidity/basicity of the catalyst, enabling the mixed metal oxide catalyst to achieve a mono-phenol yield of 15.4% from lignin hydrogenolysis, which is twice as high as that of the single metal oxide catalyst (7.8%).

3.3 Molecular sieve

Molecular sieves are hydrated aluminosilicates or natural zeolites. According to the SiO2 and Al2O3molar ratios, molecular sieves with different pore sizes can be obtained. Molecular sieves possess Lewis acid sites and Brønsted acid sites, making them environmentally friendly with tunable acidity. Furthermore, their excellent thermal stability and easily controllable pore sizes make them suitable catalysts or supports for industrial reactions. In recent years, molecular sieves have been widely used as hydrodeoxygenation catalyst supports for bio-oil upgrading, particularly for the refining of lignin-derived bio-oils[84]. Hu et al.[85]prepared a novel supported HZSM-5 activated carbon catalyst for the online upgrading of soybean straw pyrolysis products. Through a series of characterizations (Figure 12), it was found that the HZSM-5 molecular sieve was wrapped on the surface of the activated carbon, and the addition of activated carbon gave the catalyst a mesoporous structure and more acid sites. The results showed that the catalyst with an HZSM-5 to activated carbon mass ratio of 18:5 exhibited the highest catalytic efficiency for converting biomass into aromatics, with a selectivity of 99.5%. Among these, the conversion rate of benzene, toluene, and xylene (BTX) was 75.7%, and the yield was 74.7 mg/g.
As a type of molecular sieve, the acidity and pore structure of zeolites are key factors influencing the degree of lignin pyrolysis and product distribution[86]. Wu et al.[87]synthesized a series of 12-MR β-zeolites with varying acidity and porosity for the catalytic fast pyrolysis of lignin. The results indicated that β-zeolites with moderate acidity promoted the production of aromatic compounds, while the introduction of mesopores further enhanced lignin deoxygenation. At 600 °C, the moderately acidic Beta (36) zeolite exhibited the highest bio-oil yield and aromatic selectivity.

4 Conclusion and Outlook

This article reviews the latest research progress on the hydrodeoxygenation of lignin and its derivatives to prepare liquid organic hydrogen carriers (LOHCs). It proposes that biomass-derived organic compounds, such as alcohols and aromatics, can serve as LOHCs, and summarizes catalysts commonly used for dehydrogenation and hydrogenation reactions of these materials. Current research indicates that, in addition to catalysts with single functionality for either dehydrogenation or hydrogenation, bimetallic nanocatalysts can simultaneously facilitate both processes for LOHCs, offering significant development prospects. Finally, the influence of catalyst supports on the preparation of LOHCs from lignin is discussed in detail. The main conclusions of the paper are as follows.
(1) Carbon materials possess advantages such as wide availability and well-developed porous structures. By regulating their pore structure, specific surface area, and other properties, they can efficiently catalyze lignin hydrogenolysis to produce liquid hydrogen storage materials. Common carbon materials used as supports include activated carbon, carbon nanotubes, and metal-organic frameworks. Furthermore, nitrogen doping of carbon materials can enhance the interaction between the support and the metal; meanwhile, nitrogen elements can serve to anchor metal elements, improve metal dispersion, and increase the catalytic activity of the catalyst.
(2) Metal oxides are commonly used catalyst supports for lignin hydrogenolysis. Different metal oxides possess distinct catalytic properties, while mixed metal oxide supports not only improve lignin conversion but also offer advantages such as suppressing coke formation.
(3) Molecular sieves have been widely used in lignin hydrogenolysis due to their advantages such as adjustable acidity/basicity, controllable pore size, and good thermal stability.
Due to the limited and non-renewable nature of fossil resources, their depletion has become an irreversible trend[97], hydrogen energy is a promising alternative to fossil fuels, but it suffers from difficulties in storage and transportation. Liquid hydrogen storage materials can effectively solve these problems and hold great application prospects. As a green renewable resource, the development and utilization of lignin are particularly important. Current research on lignin mainly focuses on producing bio-oxygenated fuels from lignin and using lignin as a catalyst support. In recent years, progress has been made in using compounds derived from renewable lignin as liquid hydrogen storage materials; however, research on the one-step preparation of alcohol-based liquid hydrogen storage materials from lignin remains scarce. Meanwhile, achieving hydrogenation and dehydrogenation of biomass-based liquid hydrogen storage materials faces many challenges regarding their practical application. Therefore, future efforts could consider constructing catalytic systems to achieve the one-step depolymerization of lignin for preparing alcohol-based liquid hydrogen storage materials. Simultaneously, by regulating the acidity/basicity of the catalyst or reaction conditions, conversion between alcohol-based and phenol-based liquid hydrogen storage materials within the same catalytic system can be realized, which is of significant importance for the ultimate realization of lignin-based liquid hydrogen storage materials.

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Funding

National Natural Science Foundation of China(22378145)

National Natural Science Foundation of China(22178129)

State Key Laboratory of Pulp and Paper Engineering(202407)

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