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Sustainable Production of Benzene from Lignin

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Sustainable Production of Benzene from Lignin ARTICLE https://doi.org/10.1038/s41467-021-24780-8 OPEN Sustainable production of benzene from lignin ✉ Qinglei Meng1 , Jiang Yan1,2, Ruizhi Wu1,2, Huizhen Liu 1,2, Yang Sun3, NingNing Wu3, Junfeng Xiang 3, ✉ Lirong Zheng4, Jing Zhang4 & Buxing Han 1,2,5 Benzene is a widely used commodity chemical, which is currently produced from fossil resources. Lignin, a waste from lignocellulosic biomass industry, is the most abundant renewable source of benzene ring in nature. Efficient production of benzene from lignin, which requires total transformation of Csp2-Csp3/Csp2-O into C-H bonds without side 1234567890():,; hydrogenation, is of great importance, but has not been realized. Here, we report that high- silica HY zeolite supported RuW alloy catalyst enables in situ refining of lignin, exclusively to benzene via coupling Bronsted acid catalyzed transformation of the Csp2-Csp3 bonds on the local structure of lignin molecule and RuW catalyzed hydrogenolysis of the Csp2-O bonds using the locally abstracted hydrogen from lignin molecule, affording a benzene yield of 18.8% on lignin weight basis in water system. The reaction mechanism is elucidated in detail by combination of control experiments and density functional theory calculations. The high- performance protocol can be readily scaled up to produce 8.5 g of benzene product from 50.0 g lignin without any saturation byproducts. This work opens the way to produce ben- zene using lignin as the feedstock efficiently. 1 Beijing National Laboratory for Molecular Sciences, CAS Laboratory of Colloid and Interface and Thermodynamics, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China. 2 School of Chemical Science, University of Chinese Academy of Sciences, Beijing, China. 3 Center for Physicochemical Analysis and Measurement, Chinese Academy of Sciences, Beijing, China. 4 Institute of High Energy Physics, Chinese Academy of Sciences, Beijing, China. 5 Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of ✉ Chemistry and Molecular Engineering, East China Normal University, Shanghai, China. email: [email protected]; [email protected] NATURE COMMUNICATIONS | (2021) 12:4534 | https://doi.org/10.1038/s41467-021-24780-8 | www.nature.com/naturecommunications 1 ARTICLE NATURE COMMUNICATIONS | https://doi.org/10.1038/s41467-021-24780-8 owadays, benzene is an indispensable commodity in methane to benzene (Fig. 1b)6–8. However, all of the above routes chemical industry with world production of more than 61 depend on fossil resource, and has several disadvantages, such as N 1 million metric tons in 2019 (www.statista.com/statistics/ complicated and severe conditions, high energy consumption and 1108114/global-benzene-capacity). The global benzene demand is serious environmental pollution9–11. Thus, more benign and anticipated to grow with a rate of 2.9% annually in the next sustainable strategy, such as utilization of renewable resources as decade1 (www.chemanalyst.com/industry-report/benzene- raw materials to economically produce benzene, is highly desired, market-56). Especially in the manufacturing industry, benzene which can liberate us from the reliance on fossil resource and is of is widely used in many sectors, where it is combined and pro- great industrial and social significance12,13. Such an attractive, cessed with other basic chemicals (e.g. ethylene and propylene) to cheap and non-edible material is lignocellulosic biomass, gener- produce valuable consumer goods, such as clothing, packaging, ated from forestry and agricultural activity worldwide14.Asa car parts, building materials, pharmaceuticals, cosmetics, flame main constituent of lignocellulose, lignin is the most abundant retardant, compact discs, eyeglass lenses, carpet, medical renewable source composed of aromatic building blocks in implants, foam insulation, adhesives, footwear, contact lens, dyes, nature15, with an annual production of around 50 billion metric agrochemicals (Supplementary Fig. 1)1,2 (www.statista.com/ tons16. In terms of molecular structure, the aromatic character of statistics/1108114/global-benzene-capacity), (www.chemanalyst. lignin springs from the benzene ring structures, which renders com/industry-report/benzene-market-56). Currently, benzene is itself a sustainable and desirable candidate feedstock for benzene dominantly produced from petroleum and coal via catalytic production16–18. reforming, steam cracking and toluene disproportionation pro- In recent years, valorizing lignin into fossil-based chemicals has cesses, as well as coal processing (Supplementary Note 1) received extensive attention, and various valuable chemicals used (Fig. 1a)3–5. Besides, there is also ongoing research to convert for transport fuels and industrial manufactures have been Fig. 1 Strategies employed for the benzene production. a Traditional industry route for benzene production. b Natural gas route for benzene production. c Lignin-to-benzene route. 2 NATURE COMMUNICATIONS | (2021) 12:4534 | https://doi.org/10.1038/s41467-021-24780-8 | www.nature.com/naturecommunications NATURE COMMUNICATIONS | https://doi.org/10.1038/s41467-021-24780-8 ARTICLE obtained employing lignin as the feedstock19–28. For example, acting as the cheap and green reaction medium, no other advances in the seminal work of Luterbacher and co-workers on reductant or reactant is needed. This efficient strategy affords aldehyde stabilization of lignin improved the lignin depolymer- mild-condition abstraction of benzene from lignin molecule ization efficiency and yielded the mixture of guaiacyl and syringyl structures with a benzene yield as high as 18.8% on lignin weight monomers, such as alkyl-substituted guaiacol/syringol20,21, basis, and our high-performance protocol can be readily scaled up hydroxypropyl-substituted guaiacol/syringol20,21 and guaiacyl/ to produce 8.5 g of benzene product from 50.0 g lignin without syringyl propane diones22, via hydrogenolysis and oxidation any saturation byproducts. approaches. In the pioneering work of Stahl and co-workers23, lignin could be depolymerized into syringaldehyde and vanillin via successive oxidation-formylation-hydrolysis processes. Wang Results and co-workers conducted the direct hydrodeoxygenation of Optimization study. We focused our in situ refining strategy 24 – lignin to alkyl-substituted arenes and hydrocarbons . Sels and studies initially on the overall transformation of the Csp2 Csp3/ 25 fi – co-workers developed an integrated biore nery process that Csp2 O bonds by using 1-(4-methoxyphenyl)-1-propanol (1a)as converted lignin into phenol with high yield. Wang and co- the model compound because of its lignin-mimetic phenylpro- 26 – workers also obtained phenol product from lignin by a multi- panol structure [(CH3O)Ph-Csp3(OH) ] with only one methoxy fi – step oxidation and decarboxylation methodology. These ndings group [Csp2 O(CH3)] and one 1-hydroxypropyl group – place a premium on strategies that pursue benzene from lignin, [Csp2 Csp3(OH)] substituted on the benzene ring, which sim- however in the currently reported methodologies, such as cata- plifies the study. After extensive screening of various conditions, lytic pyrolysis29–31, hydrodeoxygenation32–34 and combined cat- we identified the optimized catalytic system and reaction condi- alytic processing15,35, benzene could only be detected in quite a tions shown in Table 1 and Supplementary Fig. 3, which low yield in the complex mixture containing the aforementioned employed cheap and commercially available hydrogen-type fau- = phenolic hydroxyl, methoxyl and alkyl-substituted aromatic jasite Y zeolite (HY30, Si/Al ratio 30) with supported RuW alloy products. Although there is ongoing research on lignin valor- component using water as the reaction medium at 180 °C under ization, efficient lignin-to-benzene route has not been reported so nitrogen atmosphere (Table 1, entries 1–3, Supplementary Fig. 3a, – – far. Obviously, the complex chemical bonding environment, b). As expected, the transformations of the Csp2 Csp3/Csp2 O especially the stable aromatic carbon–aliphatic carbon bonds in 1a did not occur without the catalyst, despite the – – – (Csp2 Csp3) and aromatic carbon oxygen (Csp2 O) bonds func- achievable dehydroxylation (1h) in the blank experiment 45 fi tionalized on the benzene rings truly limited the abstraction of (Table 1, entry 1) . It is clear that HY30 zeolite ef ciently cata- – – benzene from the lignin structure. In this context, further clea- lyzed the deconstruction of the Csp2 Csp3 bond in 1a into Csp2 H – – – vage of the unbroken Csp2 Csp3/Csp2 O bonds in the above bond, but unfortunately the Csp2 O bond in anisole (1d) was not generated alkylbenzenes and alkylphenols for desired benzene reactive when only HY30 was used as the catalyst (Table 1, entry product can only be realized via dealkylation, dealkenylation and 2). With RuW alloy introduced into the catalytic system, these reductive cleavage processes under quite harsh conditions (for unreacted anisole molecules could be further converted into 36–40 example, high temperature, etc.) . Moreover, such required benzene (1b) via the SSH process of the Csp2–O bond (Table 1, reaction conditions often lead to inevitable side reactions33. For entry 3). It can be found that the selectivity to benzene (1b) could example, the concurrent hydrogenation of the benzene ring in the be 97.3% with a remained anisole (1d) selectivity of 2.5% at 99.9% hydroprocessing stage of the lignin
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