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Title: Determination of hydroxyl groups in biorefinery resources via quantitative 31P NMR spectroscopy [Determination of hydroxyl groups in biorefinery resources via quantitative 31P Nuclear Magnetic Resonance Spectroscopy]

Abstract

The analysis of chemical structural characteristics of biorefinery product streams (such as lignin and tannin) has advanced substantially over the past decade, with traditional wet-chemical techniques being replaced or supplemented by NMR methodologies. Quantitative 31P NMR spectroscopy is a promising technique for the analysis of hydroxyl groups because of its unique characterization capability and broad potential applicability across the biorefinery research community. This protocol describes procedures for (i) the preparation/solubilization of lignin and tannin, (ii) the phosphitylation of their hydroxyl groups, (iii) NMR acquisition details, and (iv) the ensuing data analyses and means to precisely calculate the content of the different types of hydroxyl groups. Compared with traditional wet-chemical techniques, the technique of quantitative 31P NMR spectroscopy offers unique advantages in measuring hydroxyl groups in a single spectrum with high signal resolution. Furthermore, the method provides complete quantitative information about the hydroxyl groups with small amounts of sample (~30 mg) within a relatively short experimental time (~30–120 min).

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3];  [1]; ORCiD logo [4]; ORCiD logo [5]; ORCiD logo [6]
  1. The Univ. of Tennessee, Knoxville, TN (United States)
  2. Ca’ Foscari Univ. of Venice, Venice (Italy)
  3. Qingdao Univ., Qingdao (China)
  4. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  5. The Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); The Univ. of Tennessee Inst. of Agriculture, Knoxville, TN (United States)
  6. North Carolina State Univ., Raleigh, NC (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1558488
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Nature Protocols
Additional Journal Information:
Journal Name: Nature Protocols; Journal ID: ISSN 1754-2189
Publisher:
Nature Publishing Group
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Lignin; tannin; biomass; 31P NMR; hydroxyl; phosphitylation

Citation Formats

Meng, Xianzhi, Crestini, Claudia, Ben, Haoxi, Hao, Naijia, Pu, Yunqiao Joseph, Ragauskas, Arthur J., and Argyropoulos, Dimitris S. Determination of hydroxyl groups in biorefinery resources via quantitative 31P NMR spectroscopy [Determination of hydroxyl groups in biorefinery resources via quantitative 31P Nuclear Magnetic Resonance Spectroscopy]. United States: N. p., 2019. Web. doi:10.1038/s41596-019-0191-1.
Meng, Xianzhi, Crestini, Claudia, Ben, Haoxi, Hao, Naijia, Pu, Yunqiao Joseph, Ragauskas, Arthur J., & Argyropoulos, Dimitris S. Determination of hydroxyl groups in biorefinery resources via quantitative 31P NMR spectroscopy [Determination of hydroxyl groups in biorefinery resources via quantitative 31P Nuclear Magnetic Resonance Spectroscopy]. United States. doi:10.1038/s41596-019-0191-1.
Meng, Xianzhi, Crestini, Claudia, Ben, Haoxi, Hao, Naijia, Pu, Yunqiao Joseph, Ragauskas, Arthur J., and Argyropoulos, Dimitris S. Wed . "Determination of hydroxyl groups in biorefinery resources via quantitative 31P NMR spectroscopy [Determination of hydroxyl groups in biorefinery resources via quantitative 31P Nuclear Magnetic Resonance Spectroscopy]". United States. doi:10.1038/s41596-019-0191-1. https://www.osti.gov/servlets/purl/1558488.
@article{osti_1558488,
title = {Determination of hydroxyl groups in biorefinery resources via quantitative 31P NMR spectroscopy [Determination of hydroxyl groups in biorefinery resources via quantitative 31P Nuclear Magnetic Resonance Spectroscopy]},
author = {Meng, Xianzhi and Crestini, Claudia and Ben, Haoxi and Hao, Naijia and Pu, Yunqiao Joseph and Ragauskas, Arthur J. and Argyropoulos, Dimitris S.},
abstractNote = {The analysis of chemical structural characteristics of biorefinery product streams (such as lignin and tannin) has advanced substantially over the past decade, with traditional wet-chemical techniques being replaced or supplemented by NMR methodologies. Quantitative 31P NMR spectroscopy is a promising technique for the analysis of hydroxyl groups because of its unique characterization capability and broad potential applicability across the biorefinery research community. This protocol describes procedures for (i) the preparation/solubilization of lignin and tannin, (ii) the phosphitylation of their hydroxyl groups, (iii) NMR acquisition details, and (iv) the ensuing data analyses and means to precisely calculate the content of the different types of hydroxyl groups. Compared with traditional wet-chemical techniques, the technique of quantitative 31P NMR spectroscopy offers unique advantages in measuring hydroxyl groups in a single spectrum with high signal resolution. Furthermore, the method provides complete quantitative information about the hydroxyl groups with small amounts of sample (~30 mg) within a relatively short experimental time (~30–120 min).},
doi = {10.1038/s41596-019-0191-1},
journal = {Nature Protocols},
number = ,
volume = ,
place = {United States},
year = {2019},
month = {8}
}

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  • Harton, Shane E.; Pingali, Sai Venkatesh; Nunnery, Grady A.
  • ACS Macro Letters, Vol. 1, Issue 5
  • DOI: 10.1021/mz300045e

Determination of phenolic hydroxyl groups in residual lignin using a modified UV-method
journal, May 1999


Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5
journal, January 2010

  • Kim, Hoon; Ralph, John
  • Org. Biomol. Chem., Vol. 8, Issue 3
  • DOI: 10.1039/B916070A

The occurrence of tricin and its derivatives in plants
journal, January 2016

  • Li, Mi; Pu, Yunqiao; Yoo, Chang Geun
  • Green Chemistry, Vol. 18, Issue 6
  • DOI: 10.1039/C5GC03062E

Determination of Water Content in Olive Oil by 31 P NMR Spectroscopy
journal, March 2008

  • Hatzakis, Emmanuel; Dais, Photis
  • Journal of Agricultural and Food Chemistry, Vol. 56, Issue 6
  • DOI: 10.1021/jf073227n

The Effects on Lignin Structure of Overexpression of Ferulate 5-Hydroxylase in Hybrid Poplar 1
journal, April 2009

  • Stewart, Jaclyn J.; Akiyama, Takuya; Chapple, Clint
  • Plant Physiology, Vol. 150, Issue 2
  • DOI: 10.1104/pp.109.137059

Facile Quantitative Analysis of Hydroxyl End Groups of Poly(2,6-dimethyl-1,4-phenylene oxide)s by 31P NMR Spectroscopy
journal, October 1994

  • Chan, K. P.; Argyropoulos, D. S.; White, D. M.
  • Macromolecules, Vol. 27, Issue 22
  • DOI: 10.1021/ma00100a021

Downregulation of pectin biosynthesis gene GAUT4 leads to reduced ferulate and lignin-carbohydrate cross-linking in switchgrass
journal, January 2019


Chemical Transformations of Buddleja davidii Lignin during Ethanol Organosolv Pretreatment
journal, April 2010

  • Hallac, Bassem B.; Pu, Yunqiao; Ragauskas, Arthur J.
  • Energy & Fuels, Vol. 24, Issue 4
  • DOI: 10.1021/ef901556u

Elucidation of Lignin Structure by Quantitative 2D NMR
journal, June 2011

  • Sette, Marco; Wechselberger, Rainer; Crestini, Claudia
  • Chemistry - A European Journal, Vol. 17, Issue 34
  • DOI: 10.1002/chem.201003045

Lignins as macromonomers for polyurethane synthesis: A comparative study on hydroxyl group determination
journal, January 2008

  • Cateto, Carolina Andreia; Barreiro, Maria Filomena; Rodrigues, Alírio Egídio
  • Journal of Applied Polymer Science, Vol. 109, Issue 5
  • DOI: 10.1002/app.28393

Bioconversion of hybrid poplar to ethanol and co-products using an organosolv fractionation process: Optimization of process yields
journal, January 2006

  • Pan, Xuejun; Gilkes, Neil; Kadla, John
  • Biotechnology and Bioengineering, Vol. 94, Issue 5, p. 851-861
  • DOI: 10.1002/bit.20905

31 P NMR Chemical Shifts of Solvents and Products Impurities in Biomass Pretreatments
journal, November 2017


31P-N.m.r. spectroscopy in wood chemistry. Phosphite derivatives of carbohydrates
journal, November 1991


Phosphorus-31 NMR spectroscopic analysis of coal pyrolysis condensates and extracts for heteroatom functionalities possessing labile hydrogen
journal, November 1988

  • Wroblewski, A. E.; Lensink, C.; Markuszewski, R.
  • Energy & Fuels, Vol. 2, Issue 6
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Determination of Carbonyl Groups of Six Round Robin Lignins by Modified Oximation and FTIR Spectroscopy
journal, January 1998


3D Chemical Image using TOF-SIMS Revealing the Biopolymer Component Spatial and Lateral Distributions in Biomass
journal, October 2012

  • Jung, Seokwon; Foston, Marcus; Kalluri, Udaya C.
  • Angewandte Chemie International Edition, Vol. 51, Issue 48
  • DOI: 10.1002/anie.201205243