Non-catalytic oxidative depolymerization of lignin in perfluorodecalin to produce phenolic monomers

Hafezisefat, Parinaz; Lindstrom, Jake K.; Brown, Robert C.; Qi, Long

doi:10.1039/d0gc02505d

Cited by 27 publications

(25 citation statements)

References 41 publications

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“…Recently, a milder and more sustainable, noncatalytic oxidative depolymerization reaction of lignin using molecular oxygen with perfluorodecalin has been reported. 293 Up to about 10-fold of PAs monomer could be achieved in a short time by this method compared to conventional methods under similar conditions. 293 Therefore, PAs are abundant and renewable feedstocks which can provide unique natural properties for further construction of valuable chemicals.…”

Section: Phenolic Acid-derived Productsmentioning

confidence: 91%

“…293 Up to about 10-fold of PAs monomer could be achieved in a short time by this method compared to conventional methods under similar conditions. 293 Therefore, PAs are abundant and renewable feedstocks which can provide unique natural properties for further construction of valuable chemicals. Moreover, a high amount of PAs cannot be excreted to freshwater resources without proper treatment because it would create toxicity to animals.…”

Section: Phenolic Acid-derived Productsmentioning

confidence: 91%

“…It is important to note that these reported methods normally involve the use of organic solvents and noble metal or alkaline metal catalysts. Recently, a milder and more sustainable, noncatalytic oxidative depolymerization reaction of lignin using molecular oxygen with perfluorodecalin has been reported . Up to about 10-fold of PAs monomer could be achieved in a short time by this method compared to conventional methods under similar conditions …”

Section: Production Of Lignocellulosic Biomass-derived Productsmentioning

confidence: 99%

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Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

et al. 2021

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Since the industrial revolution, the rapid growth and development of global industries have depended largely upon the utilization of coal-derived chemicals, and more recently, the utilization of petroleum-based chemicals. These developments have followed a linear economy model (produce, consume, and dispose). As the world is facing a serious threat from the climate change crisis, a more sustainable solution for manufacturing, i.e., circular economy in which waste from the same or different industries can be used as feedstocks or resources for production offers an attractive industrial/business model. In nature, biological systems, i.e., microorganisms routinely use their enzymes and metabolic pathways to convert organic and inorganic wastes to synthesize biochemicals and energy required for their growth. Therefore, an understanding of how selected enzymes convert biobased feedstocks into special (bio)chemicals serves as an important basis from which to build on for applications in biocatalysis, metabolic engineering, and synthetic biology to enable biobased processes that are greener and cleaner for the environment. This review article highlights the current state of knowledge regarding the enzymatic reactions used in converting biobased wastes (lignocellulosic biomass, sugar, phenolic acid, triglyceride, fatty acid, and glycerol) and greenhouse gases (CO 2 and CH 4 ) into value-added products and discusses the current progress made in their metabolic engineering. The commercial aspects and life cycle assessment of products from enzymatic and metabolic engineering are also discussed. Continued development in the field of metabolic engineering would offer diversified solutions which are sustainable and renewable for manufacturing valuable chemicals.

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Section: Phenolic Acid-derived Productsmentioning

confidence: 91%

Section: Phenolic Acid-derived Productsmentioning

confidence: 91%

Section: Production Of Lignocellulosic Biomass-derived Productsmentioning

confidence: 99%

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Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

et al. 2021

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“…[20][21][22][23][24][25] Among the alternatives from biomass valorization, the production of 5-hydroxymethylfurfural (HMF) from hexoses is a versatile platform for the synthesis of furan-based chemicals such as furyl diamide, diamidine, diimidate, and diformylfuran. [26][27] Therefore, oxidative depolymerization of lignin and lignin model compounds can obtain aromatic aldehydes and ketones [28][29][30][31][32][33][34][35][36][37][38] such as vanillin veratraldehyde, acetovanillone, acetosyringone, and syringaldehyde. To further demonstrate the utility of our protocol, we used our one-pot strategy for the efficacious synthesis of 2,5-dicyanofuran from biomass-derived 2,5-diformylfuran.…”

Section: Introductionmentioning

confidence: 99%

Tandem Triphosgene-Assisted Metal-Free One-pot Preparation of Nitriles and Amides from Aldehydes and Ketones

Liu¹,

Wei

Ma³

2021

Preprint

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Here we report a facile and efficient triphosgene-assisted one-pot conversion of aldehydes/ketones into nitriles/amides. The triphosgene, a kind of phosgene alternative, containing both ester linkage and chloromethyl units, easily reacts with oximes for the preparation of nitriles/amides. However, the reaction of oximes with triphosgene can’t fully convert corresponding nitriles/amides due to hydrolysis of oximes to aldehydes or ketones. Our protocol tandem proceeds smoothly without the use of organic base and metal catalysts. Diverse functionalized aromatic, aliphatic, and allylic aldehydes/ketones incorporating biomass-derived platform compounds were successfully converted to nitriles and amides in excellent yields. Compared to step-by-step reaction, this tandem strategy is characterized by multi-step reaction in one pot, mild reaction conditions, and fewer by-products.

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“…%) без образования твердого остатка [20]. Основная проблема производства монофенильных продуктов из лигнина -это нежелательная реполимеризация фрагментированных структур лигнина [21].…”

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Catalytic Hydrogenolysis of Lignin Peroxidase Oxidation Products

Шиманская¹,

Гребенникова²,

Филатова³

2021

Вестник Тверского Государственного Университета. Серия: Химия

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Продукты переработки лигнина могут быть использованы в качестве компонентов биотоплив. Однако переработка лигнина является энергозатратным процессом с низким выходом химически ценных продуктов. Предобработка лигнина биокаталитическим способом позволяет в мягких условиях разбить полимер на более короткие отрезки, которые проще подвергаются в дальнейшем процессу гидрогенолиза, таким образом, понижая энергозатратность процесса получения мономерных фрагментов. В статье приведены экспериментальные данные по каталитическому гидрогенолизу лигнина, предварительно обработанного пероксидом водорода в присутствии перокcидазы хрена. The products of lignin processing can be used as components of biofuels. However, lignin processing is an energy-consuming process with a low yield of chemically valuable products. The pretreatment of lignin by the biocatalytic method allows, under mild conditions, to break the polymer into shorter segments, which are easier to undergo further hydrogenolysis, thus reducing the energy consumption of the process of obtaining monomer fragments. The article presents experimental data on the catalytic hydrogenolysis of products of lignin peroxidase oxidation.

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Non-catalytic oxidative depolymerization of lignin in perfluorodecalin to produce phenolic monomers

Abstract: We demonstrate for the first time non-catalytic, oxidative cracking with molecular oxygen (O2) to depolymerize native lignin into oxygenated phenolic monomers. Maximum monomer yield of 10.5 wt% was achieved at...

Cited by 27 publications

References 41 publications

Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

Tandem Triphosgene-Assisted Metal-Free One-pot Preparation of Nitriles and Amides from Aldehydes and Ketones

Catalytic Hydrogenolysis of Lignin Peroxidase Oxidation Products

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