Aromatic Monomers by in Situ Conversion of Reactive Intermediates in the Acid-Catalyzed Depolymerization of Lignin

Conversion of lignin into well-defined aromatic chemicals is a highly attractive goal but is often hampered by recondensation of the formed fragments, especially in acidolysis. Here, we describe new strategies that markedly suppress such undesired pathways to result in diverse aromatic compounds pre...

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Vydáno v:Journal of the American Chemical Society Ročník 137; číslo 23; s. 7456 - 7467
Hlavní autoři: Deuss, Peter J., Scott, Martin, Tran, Fanny, Westwood, Nicholas J., de Vries, Johannes G., Barta, Katalin
Médium: Journal Article
Jazyk:angličtina
Vydáno: WASHINGTON Amer Chemical Soc 17.06.2015
Témata:
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OXIDATION
HYDROGENOLYSIS
O BOND-CLEAVAGE
ORGANOSOLV LIGNIN
METAL-CATALYSTS
ETHANOLYSIS PRODUCTS
DEGRADATION
ARYL ETHERS
MODEL COMPOUNDS
RENEWABLE CHEMICALS
ISSN:0002-7863, 1520-5126
On-line přístup:Zjistit podrobnosti o přístupu
Tagy: Přidat tag
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Abstract Conversion of lignin into well-defined aromatic chemicals is a highly attractive goal but is often hampered by recondensation of the formed fragments, especially in acidolysis. Here, we describe new strategies that markedly suppress such undesired pathways to result in diverse aromatic compounds previously not systematically targeted from lignin: Model studies established that a catalytic amount of triflic acid is very effective in cleaving the beta-O-4 linkage, most abundant in lignin. An aldehyde product was identified as the main cause of side reactions under cleavage conditions. Capturing this unstable compound by reaction with diols and by in situ catalytic hydrogenation or decarbonylation lead to three distinct groups of aromatic compounds in high yields acetals, ethanol and ethyl aromatics, and methyl aromatics. Notably, the same product groups were obtained when these approaches were successfully extended to lignin. In addition, the formation of higher molecular weight side products was markedly suppressed, indicating that the aldehyde intermediates play a significant role in these processes. The described strategy has the potential to be generally applicable for the production of interesting aromatic compounds from lignin.
AbstractList Conversion of lignin into well-defined aromatic chemicals is a highly attractive goal but is often hampered by recondensation of the formed fragments, especially in acidolysis. Here, we describe new strategies that markedly suppress such undesired pathways to result in diverse aromatic compounds previously not systematically targeted from lignin. Model studies established that a catalytic amount of triflic acid is very effective in cleaving the β-O-4 linkage, most abundant in lignin. An aldehyde product was identified as the main cause of side reactions under cleavage conditions. Capturing this unstable compound by reaction with diols and by in situ catalytic hydrogenation or decarbonylation lead to three distinct groups of aromatic compounds in high yields acetals, ethanol and ethyl aromatics, and methyl aromatics. Notably, the same product groups were obtained when these approaches were successfully extended to lignin. In addition, the formation of higher molecular weight side products was markedly suppressed, indicating that the aldehyde intermediates play a significant role in these processes. The described strategy has the potential to be generally applicable for the production of interesting aromatic compounds from lignin.
Conversion of lignin into well-defined aromatic chemicals is a highly attractive goal but is often hampered by recondensation of the formed fragments, especially in acidolysis. Here, we describe new strategies that markedly suppress such undesired pathways to result in diverse aromatic compounds previously not systematically targeted from lignin: Model studies established that a catalytic amount of triflic acid is very effective in cleaving the beta-O-4 linkage, most abundant in lignin. An aldehyde product was identified as the main cause of side reactions under cleavage conditions. Capturing this unstable compound by reaction with diols and by in situ catalytic hydrogenation or decarbonylation lead to three distinct groups of aromatic compounds in high yields acetals, ethanol and ethyl aromatics, and methyl aromatics. Notably, the same product groups were obtained when these approaches were successfully extended to lignin. In addition, the formation of higher molecular weight side products was markedly suppressed, indicating that the aldehyde intermediates play a significant role in these processes. The described strategy has the potential to be generally applicable for the production of interesting aromatic compounds from lignin.
Author Deuss, Peter J.
Scott, Martin
Tran, Fanny
Barta, Katalin
Westwood, Nicholas J.
de Vries, Johannes G.
Author_xml – sequence: 1
  givenname: Peter J.
  orcidid: 0000-0002-2254-2500
  surname: Deuss
  fullname: Deuss, Peter J.
  organization: Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
– sequence: 2
  givenname: Martin
  orcidid: 0000-0002-9830-3856
  surname: Scott
  fullname: Scott, Martin
  organization: Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
– sequence: 3
  givenname: Fanny
  surname: Tran
  fullname: Tran, Fanny
  organization: Univ St Andrews, Sch Chem & Biomed Sci Res Complex, St Andrews KY16 9ST, Fife, Scotland
– sequence: 4
  givenname: Nicholas J.
  orcidid: 0000-0003-0630-0138
  surname: Westwood
  fullname: Westwood, Nicholas J.
  organization: Univ St Andrews, Sch Chem & Biomed Sci Res Complex, St Andrews KY16 9ST, Fife, Scotland
– sequence: 5
  givenname: Johannes G.
  orcidid: 0000-0001-5245-7748
  surname: de Vries
  fullname: de Vries, Johannes G.
  email: johannes.devries@catalysis.de
  organization: Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
– sequence: 6
  givenname: Katalin
  surname: Barta
  fullname: Barta, Katalin
  email: k.barta@rug.nl
  organization: Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
BackLink https://www.ncbi.nlm.nih.gov/pubmed/26001165$$D View this record in MEDLINE/PubMed
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Issue 23
Keywords OXIDATION
HYDROGENOLYSIS
O BOND-CLEAVAGE
ORGANOSOLV LIGNIN
METAL-CATALYSTS
ETHANOLYSIS PRODUCTS
DEGRADATION
ARYL ETHERS
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RENEWABLE CHEMICALS
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Snippet Conversion of lignin into well-defined aromatic chemicals is a highly attractive goal but is often hampered by recondensation of the formed fragments,...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Aromatic Monomers by in Situ Conversion of Reactive Intermediates in the Acid-Catalyzed Depolymerization of Lignin
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