Alkylphenols to phenol and olefins by zeolite catalysis: a pathway to valorize raw and fossilized lignocellulose

Verboekend, Danny; Liao, Yuhe; Schutyser, Wouter

doi:10.1039/c5gc01868d

Cited by 112 publications

(87 citation statements)

References 65 publications

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“…The lignin‐derived alkylmethoxyphenols can be used in the fragrance industry or upgraded to produce alkylbenzenes or alkylphenols by catalytic hydrodeoxygenation . Another interesting option is to demethoxylate and dealkylate the obtained methoxylphenols to obtain phenol, which is a valuable base chemical …”

Section: Figurementioning

confidence: 99%

Effective Release of Lignin Fragments from Lignocellulose by Lewis Acid Metal Triflates in the Lignin‐First Approach

et al. 2016

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Adding value to lignin, the most complex and recalcitrant fraction in lignocellulosic biomass, is highly relevant to costefficient operation of biorefineries. We report the use of homogeneous metal triflates to rapidly release lignin from biomass. Combined with metal-catalyzed hydrogenolysis, the process separates woody biomass into few lignin-derived alkylmethoxyphenols and cellulose under mild conditions. Model compound studies show the unique catalytic properties of metal triflates in cleaving lignin-carbohydrate interlinkages. The lignin fragments can then be disassembled by hydrogenolysis. The tandem process is flexible and allows obtaining good aromatic monomer yields from different woods (36-48 wt %, lignin base). The cellulose-rich residue is an ideal feedstock for established biorefining processes. The highly productive strategy is characterized by short reaction times, low metal triflate catalyst requirement, and leaving cellulose largely untouched.

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Section: Figurementioning

confidence: 99%

Effective Release of Lignin Fragments from Lignocellulose by Lewis Acid Metal Triflates in the Lignin‐First Approach

et al. 2016

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“…Similarly,M n(OAc) 2 exhibited higher activity compared to MnSO 4 and MnCl 2 (see Table S3, entries 11 and 12). We also performed the reaction using either Ni(OAc) 2 ,Z n(OAc) 2 or Cu(OAc) 2 in the presence of Mn(OAc) 2 and KBr (see Table S3, entries [15][16][17], but the yield of TPAwas much lower (< 10 %).…”

Section: Angewandte Chemiementioning

confidence: 99%

Production of Terephthalic Acid from Corn Stover Lignin

et al. 2019

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Funneling and functionalization of am ixture of lignin-derived monomers into as ingle high-value chemical is fascinating.R eported herein is at hree-step strategy for the production of terephthalic acid (TPA) from lignin-derived monomer mixtures,i nw hichr edundant, non-uniform substitutes such as methoxy groups are removed and the desired carboxyg roups are introduced. This strategy begins with the hydro-treatment of corn-stover-derived lignin oil over as upported molybdenum catalyst to selectively remove methoxy groups.T he generated 4-alkylphenols are converted into 4alkylbenzoic acids by carbonylation with carbon monoxide. The Co-Mn-Br catalyst then oxidizes various alkylchains into carboxyg roups,transforming the 4-alkylbenzoic acid mixture into asingle product:TPA.F or this route,the overall yields of TPAb ased on lignin content of corn stover could reach 15.5 wt %, and importantly,TPA with greater than 99 %purity was obtained simply by first decanting the reaction mixture and then washing the solid product with water.

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“…[37] The aluminatedm aterials were active in the dealkylationo fp ropylphenol (Figure 8). The cracking of alkylated aromaticsp lays an important role in modern-day petroleum refineries, and is likelyt og ain high attention in future biorefineries.T hisr eactioni sc atalyzed by Brønsted and Lewis acid sites in the gas phase, but zeolites are required to achieve high phenol selectivity (> 90 %).…”

Section: Catalytic Functionalitymentioning

confidence: 99%

“…The cracking of alkylated aromaticsp lays an important role in modern-day petroleum refineries, and is likelyt og ain high attention in future biorefineries.T hisr eactioni sc atalyzed by Brønsted and Lewis acid sites in the gas phase, but zeolites are required to achieve high phenol selectivity (> 90 %). [37] The aluminatedm aterials were active in the dealkylationo fp ropylphenol (Figure 8). S-x-b samples display similarc onversions of propylphenol (X pp )t os ample ASA-6, whereas AS1-x-b samples resulted in slightly lower conversions ( Figure 8a,b).…”

Section: Catalytic Functionalitymentioning

confidence: 99%

Synthetic and Catalytic Potential of Amorphous Mesoporous Aluminosilicates Prepared by Postsynthetic Aluminations of Silica in Aqueous Media

et al. 2018

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Amorphous aluminosilicate catalysts have been used industrially on a large scale for almost a century. However, the influence of the pH on the alumination of silica in aqueous solutions has remained largely unclear. Herein, room temperature aluminations of different mesoporous amorphous silicas (fumed silica, dried silica gel, SBA‐15, MCM‐41, and COK‐12) with aqueous solutions of various pH (3–13) are explored. The aqueous solutions are prepared using different aluminum sources (Al(NO3)3 or NaAlO2) and alkaline additives (NaOH or NH4OH). The decoupling of pH and Al source using alkaline additives results in a vast experimental potential to prepare unique aluminosilicates, whereby an important role is played by the pH development during the treatment. The bulk and surface composition, acidity, aluminum coordination, morphology, hydrothermal stability, and porosity of the obtained materials are characterized. Optimal samples possess large surface areas and superior acidities (up to 50 % higher) and outstanding stabilities compared to aluminosilicates prepared with state‐of‐the‐art methods. The obtained materials are evaluated in a series of acid‐catalyzed model reactions involving substrates of various chemical reactivity and size, enabling insight in the catalytic functionality of the introduced Brønsted and Lewis sites. The potential of the obtained materials is emphasized by the similar or superior acidity and catalytic performance compared to several benchmark industrial silica–alumina‐based catalysts.

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Alkylphenols to phenol and olefins by zeolite catalysis: a pathway to valorize raw and fossilized lignocellulose

Cited by 112 publications

References 65 publications

Effective Release of Lignin Fragments from Lignocellulose by Lewis Acid Metal Triflates in the Lignin‐First Approach

Effective Release of Lignin Fragments from Lignocellulose by Lewis Acid Metal Triflates in the Lignin‐First Approach

Production of Terephthalic Acid from Corn Stover Lignin

Synthetic and Catalytic Potential of Amorphous Mesoporous Aluminosilicates Prepared by Postsynthetic Aluminations of Silica in Aqueous Media

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