Origins of Catalyst Inhibition in the Manganese-Catalysed Oxidation of Lignin Model Compounds with H O

Overview

Journal ChemSusChem

Specialty Chemistry

Date 2019 Apr 20

PMID 31001914

Citations 3

Authors

Alessia Barbieri

Johann B Kasper

Francesco Mecozzi

Osvaldo Lanzalunga

Wesley R Browne

Affiliations

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Abstract

The upgrading of complex bio-renewable feedstock, such as lignocellulose, through depolymerisation benefits from the selective reactions at key functional groups. Applying homogeneous catalysts developed for selective organic oxidative transformations to complex feedstock such as lignin is challenged by the presence of interfering components. The selection of appropriate model compounds is essential in applying new catalytic systems and identifying such interferences. Here, it was shown by using as an example the oxidation of a model substrate containing a β-O-4 linkage with H O and an in situ-prepared manganese-based catalyst, capable of efficient oxidation of benzylic alcohols, that interference from compounds liberated during the reaction can prevent its application to lignocellulose depolymerisation.

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Origins of Catalyst Inhibition in the Manganese-Catalysed Oxidation of Lignin Model Compounds with H O.

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References

Saisaha P, Pijper D, van Summeren R, Hoen R, Smit C, de Boer J . Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H(2)O(2). Org Biomol Chem. 2010; 8(19):4444-50. DOI: 10.1039/c0ob00102c. View

Reingold J, Son S, Kim S, Dullaghan C, Oh M, Frake P . Pi-bonded quinonoid transition-metal complexes. Dalton Trans. 2006; (20):2385-98. DOI: 10.1039/b602678h. View

Jensen M, Lange S, Mehn M, Que E, Que Jr L . Biomimetic aryl hydroxylation derived from alkyl hydroperoxide at a nonheme iron center. Evidence for an Fe(IV)=O oxidant. J Am Chem Soc. 2003; 125(8):2113-28. DOI: 10.1021/ja028478l. View

Cui F, Dolphin D . Metallophthalocyanines as possible lignin peroxidase models. Bioorg Med Chem. 1995; 3(5):471-7. DOI: 10.1016/0968-0896(95)00038-i. View

Barbieri A, Kasper J, Mecozzi F, Lanzalunga O, Browne W . Origins of Catalyst Inhibition in the Manganese-Catalysed Oxidation of Lignin Model Compounds with H O. ChemSusChem. 2019; 12(13):3126-3133. PMC: 6617720. DOI: 10.1002/cssc.201900689. View

Lynd L, Cushman J, Nichols R, Wyman C . Fuel ethanol from cellulosic biomass. Science. 1991; 251(4999):1318-23. DOI: 10.1126/science.251.4999.1318. View

Zhang Z, Song J, Han B . Catalytic Transformation of Lignocellulose into Chemicals and Fuel Products in Ionic Liquids. Chem Rev. 2017; 117(10):6834-6880. DOI: 10.1021/acs.chemrev.6b00457. View

Oh N, Seo M, Lim M, Consugar M, Park M, Rohde J . Self-hydroxylation of perbenzoic acids at a nonheme iron(II) center. Chem Commun (Camb). 2005; (45):5644-6. DOI: 10.1039/b511302d. View

Mecozzi F, Dong J, Saisaha P, Browne W . Oxidation of Vicinal Diols to α-Hydroxy Ketones with HO and a Simple Manganese Catalyst. European J Org Chem. 2018; 2017(46):6919-6925. PMC: 5767754. DOI: 10.1002/ejoc.201701314. View

10.

Zakzeski J, Bruijnincx P, Jongerius A, Weckhuysen B . The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev. 2010; 110(6):3552-99. DOI: 10.1021/cr900354u. View

11.

Makhlynets O, Das P, Taktak S, Flook M, Mas-Balleste R, Rybak-Akimova E . Iron-promoted ortho- and/or ipso-hydroxylation of benzoic acids with H(2)O(2). Chemistry. 2009; 15(47):13171-80. DOI: 10.1002/chem.200901296. View

12.

Zhu C, Ding W, Shen T, Tang C, Sun C, Xu S . Metallo-deuteroporphyrin as a biomimetic catalyst for the catalytic oxidation of lignin to aromatics. ChemSusChem. 2015; 8(10):1768-78. DOI: 10.1002/cssc.201500048. View

13.

Chen C, Capanema E, Gracz H . Comparative studies on the delignification of pine kraft-anthraquinone pulp with hydrogen peroxide by binucleus Mn(IV) complex catalysis. J Agric Food Chem. 2003; 51(21):6223-32. DOI: 10.1021/jf034507f. View

14.

Drago R, Corden B, Barnes C . Novel cobalt(II)-catalyzed oxidative cleavage of a carbon-carbon double bond. J Am Chem Soc. 2011; 108(9):2453-4. DOI: 10.1021/ja00269a057. View

15.

Saisaha P, de Boer J, Browne W . Mechanisms in manganese catalysed oxidation of alkenes with H2O2. Chem Soc Rev. 2012; 42(5):2059-74. DOI: 10.1039/c2cs35443h. View

16.

Chen C, Capanema E, Gracz H . Reaction mechanisms in delignification of pine Kraft-AQ pulp with hydrogen peroxide using Mn(IV)-Me4DTNE as catalyst. J Agric Food Chem. 2003; 51(7):1932-41. DOI: 10.1021/jf020992n. View

17.

Lim S, Nahm K, Ra C, Cho D, Yoon U, Latham J . Effects of alkoxy groups on arene rings of lignin β-O-4 model compounds on the efficiencies of single electron transfer-promoted photochemical and enzymatic C-C Bond Cleavage Reactions. J Org Chem. 2013; 78(18):9431-43. DOI: 10.1021/jo401680z. View

18.

Pijper D, Saisaha P, de Boer J, Hoen R, Smit C, Meetsma A . The unexpected role of pyridine-2-carboxylic acid in manganese based oxidation catalysis with pyridin-2-yl based ligands. Dalton Trans. 2010; 39(43):10375-81. DOI: 10.1039/c0dt00452a. View

19.

Dong J, Unjaroen D, Mecozzi F, Harvey E, Saisaha P, Pijper D . Manganese-catalyzed selective oxidation of aliphatic C-H groups and secondary alcohols to ketones with hydrogen peroxide. ChemSusChem. 2013; 6(9):1774-8. DOI: 10.1002/cssc.201300378. View

20.

Koppram R, Tomas-Pejo E, Xiros C, Olsson L . Lignocellulosic ethanol production at high-gravity: challenges and perspectives. Trends Biotechnol. 2013; 32(1):46-53. DOI: 10.1016/j.tibtech.2013.10.003. View