Thermodynamics and reaction pathways of furfuryl alcohol oligomer formation

Taejin Kim; Rajeev S. Assary; Richard E. Pauls; Christopher L. Marshall; Larry A. Curtiss; Peter C. Stair

doi:10.1016/j.catcom.2013.11.030

Thermodynamics and reaction pathways of furfuryl alcohol oligomer formation

Taejin Kim
, Rajeev S. Assary
, Richard E. Pauls
, Christopher L. Marshall
, Larry A. Curtiss
, Peter C. Stair

Materials Science and Engineering

Argonne National Laboratory
Northwestern University

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

The acid-catalyzed transformation of furfuryl alcohol (FA) monomer to oligomers has been studied in the liquid phase to investigate the reaction mechanisms and intermediate species by using a combination of quantitative reaction product measurements and density functional theory calculations. FA monomer was converted into oligomers with a broad range of carbon number: C ₉-C₁₀, C₁₄-C₁₅, C ₁₉-C₂₉, > C₂₉. Based on the calculations, terminal CH₂OH dimer formation is both kinetically and thermodynamically favored, consistent with the experimental results. The order for dimer production in the C₉-C₁₀ range follows terminal CH₂OH > ether bridged-methylene bridged dimer > OH-carbon bridge.

Original language	English
Pages (from-to)	66-70
Number of pages	5
Journal	Catalysis Communications
Volume	46
DOIs	https://doi.org/10.1016/j.catcom.2013.11.030
State	Published - Feb 10 2014

Keywords

Density functional theory calculation
Furfuryl alcohol
Oligomerization
Terminal CHOH dimer

Access to Document

10.1016/j.catcom.2013.11.030

Cite this

@article{d7f82ecbc9624a248ea5c73b90223d5b,

title = "Thermodynamics and reaction pathways of furfuryl alcohol oligomer formation",

abstract = "The acid-catalyzed transformation of furfuryl alcohol (FA) monomer to oligomers has been studied in the liquid phase to investigate the reaction mechanisms and intermediate species by using a combination of quantitative reaction product measurements and density functional theory calculations. FA monomer was converted into oligomers with a broad range of carbon number: C 9-C10, C14-C15, C 19-C29, > C29. Based on the calculations, terminal CH2OH dimer formation is both kinetically and thermodynamically favored, consistent with the experimental results. The order for dimer production in the C9-C10 range follows terminal CH2OH > ether bridged-methylene bridged dimer > OH-carbon bridge.",

keywords = "Density functional theory calculation, Furfuryl alcohol, Oligomerization, Terminal CHOH dimer",

author = "Taejin Kim and Assary, \{Rajeev S.\} and Pauls, \{Richard E.\} and Marshall, \{Christopher L.\} and Curtiss, \{Larry A.\} and Stair, \{Peter C.\}",

year = "2014",

month = feb,

day = "10",

doi = "10.1016/j.catcom.2013.11.030",

language = "English",

volume = "46",

pages = "66--70",

journal = "Catalysis Communications",

issn = "1566-7367",

}

TY - JOUR

T1 - Thermodynamics and reaction pathways of furfuryl alcohol oligomer formation

AU - Kim, Taejin

AU - Assary, Rajeev S.

AU - Pauls, Richard E.

AU - Marshall, Christopher L.

AU - Curtiss, Larry A.

AU - Stair, Peter C.

PY - 2014/2/10

Y1 - 2014/2/10

N2 - The acid-catalyzed transformation of furfuryl alcohol (FA) monomer to oligomers has been studied in the liquid phase to investigate the reaction mechanisms and intermediate species by using a combination of quantitative reaction product measurements and density functional theory calculations. FA monomer was converted into oligomers with a broad range of carbon number: C 9-C10, C14-C15, C 19-C29, > C29. Based on the calculations, terminal CH2OH dimer formation is both kinetically and thermodynamically favored, consistent with the experimental results. The order for dimer production in the C9-C10 range follows terminal CH2OH > ether bridged-methylene bridged dimer > OH-carbon bridge.

AB - The acid-catalyzed transformation of furfuryl alcohol (FA) monomer to oligomers has been studied in the liquid phase to investigate the reaction mechanisms and intermediate species by using a combination of quantitative reaction product measurements and density functional theory calculations. FA monomer was converted into oligomers with a broad range of carbon number: C 9-C10, C14-C15, C 19-C29, > C29. Based on the calculations, terminal CH2OH dimer formation is both kinetically and thermodynamically favored, consistent with the experimental results. The order for dimer production in the C9-C10 range follows terminal CH2OH > ether bridged-methylene bridged dimer > OH-carbon bridge.

KW - Density functional theory calculation

KW - Furfuryl alcohol

KW - Oligomerization

KW - Terminal CHOH dimer

UR - https://www.scopus.com/pages/publications/84890479110

U2 - 10.1016/j.catcom.2013.11.030

DO - 10.1016/j.catcom.2013.11.030

M3 - Article

AN - SCOPUS:84890479110

SN - 1566-7367

VL - 46

SP - 66

EP - 70

JO - Catalysis Communications

JF - Catalysis Communications

ER -

Thermodynamics and reaction pathways of furfuryl alcohol oligomer formation

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this