The Effect of Fatty Acid Esterification on the Thermal Properties of Softwood Kraft Lignin

Klaus A. Y. Koivu, Hasan Sadeghifar, Paula A. Nousiainen, Dimitris Argyropoulos, Jussi Sipilä

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Esterification of kraft lignin inherently addresses its potential for thermoplastic applications either on its own or as a component of polymer blends. In this effort, we have investigated the selectivity of softwood kraft lignin toward esterification via acylation. LignoBoost kraft lignin was esterified with acetyl (C-2), octanoyl (C-8), lauroyl (C-12), and palmitoyl (C-16) chlorides at various molar ratios with respect to the total hydroxyls present. Quantitative P-31 NMR spectroscopy, Fourier transform infrared spectroscopy (FTIR), and gel permeation chromatography (GPC) were used to evaluate the selectivity and efficiency of these reactions on the various hydroxyl groups present. The C-8-C-16 acyl chlorides showed distinct enhanced reactivity toward the aliphatic hydroxyl groups, whereas C-2 acyl chloride was found to react uniformly with any available OH irrespective of their chemical nature. The effects of long chain acylation on the polymer and material properties were also examined using solution viscosity, thermal, and rheological measurements. Polymer blends were also produced and studied by melt extrusion. The long aliphatic chains when installed on the lignin displayed peculiar association effects in solution and enhanced the melt flow characteristics of the lignin polymer blends.
Original languageEnglish
JournalACS Sustainable Chemistry & Engineering
Volume4
Issue number10
Pages (from-to)5238–5247
Number of pages10
ISSN2168-0485
DOIs
Publication statusPublished - 2016
MoE publication typeA1 Journal article-refereed

Fields of Science

  • 116 Chemical sciences

Cite this

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title = "The Effect of Fatty Acid Esterification on the Thermal Properties of Softwood Kraft Lignin",
abstract = "Esterification of kraft lignin inherently addresses its potential for thermoplastic applications either on its own or as a component of polymer blends. In this effort, we have investigated the selectivity of softwood kraft lignin toward esterification via acylation. LignoBoost kraft lignin was esterified with acetyl (C-2), octanoyl (C-8), lauroyl (C-12), and palmitoyl (C-16) chlorides at various molar ratios with respect to the total hydroxyls present. Quantitative P-31 NMR spectroscopy, Fourier transform infrared spectroscopy (FTIR), and gel permeation chromatography (GPC) were used to evaluate the selectivity and efficiency of these reactions on the various hydroxyl groups present. The C-8-C-16 acyl chlorides showed distinct enhanced reactivity toward the aliphatic hydroxyl groups, whereas C-2 acyl chloride was found to react uniformly with any available OH irrespective of their chemical nature. The effects of long chain acylation on the polymer and material properties were also examined using solution viscosity, thermal, and rheological measurements. Polymer blends were also produced and studied by melt extrusion. The long aliphatic chains when installed on the lignin displayed peculiar association effects in solution and enhanced the melt flow characteristics of the lignin polymer blends.",
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year = "2016",
doi = "10.1021/acssuschemeng.6b01048",
language = "English",
volume = "4",
pages = "5238–5247",
journal = "ACS Sustainable Chemistry & Engineering",
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publisher = "American Chemical Society",
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The Effect of Fatty Acid Esterification on the Thermal Properties of Softwood Kraft Lignin. / Koivu, Klaus A. Y.; Sadeghifar, Hasan; Nousiainen, Paula A.; Argyropoulos, Dimitris; Sipilä, Jussi.

In: ACS Sustainable Chemistry & Engineering, Vol. 4, No. 10, 2016, p. 5238–5247.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - The Effect of Fatty Acid Esterification on the Thermal Properties of Softwood Kraft Lignin

AU - Koivu, Klaus A. Y.

AU - Sadeghifar, Hasan

AU - Nousiainen, Paula A.

AU - Argyropoulos, Dimitris

AU - Sipilä, Jussi

PY - 2016

Y1 - 2016

N2 - Esterification of kraft lignin inherently addresses its potential for thermoplastic applications either on its own or as a component of polymer blends. In this effort, we have investigated the selectivity of softwood kraft lignin toward esterification via acylation. LignoBoost kraft lignin was esterified with acetyl (C-2), octanoyl (C-8), lauroyl (C-12), and palmitoyl (C-16) chlorides at various molar ratios with respect to the total hydroxyls present. Quantitative P-31 NMR spectroscopy, Fourier transform infrared spectroscopy (FTIR), and gel permeation chromatography (GPC) were used to evaluate the selectivity and efficiency of these reactions on the various hydroxyl groups present. The C-8-C-16 acyl chlorides showed distinct enhanced reactivity toward the aliphatic hydroxyl groups, whereas C-2 acyl chloride was found to react uniformly with any available OH irrespective of their chemical nature. The effects of long chain acylation on the polymer and material properties were also examined using solution viscosity, thermal, and rheological measurements. Polymer blends were also produced and studied by melt extrusion. The long aliphatic chains when installed on the lignin displayed peculiar association effects in solution and enhanced the melt flow characteristics of the lignin polymer blends.

AB - Esterification of kraft lignin inherently addresses its potential for thermoplastic applications either on its own or as a component of polymer blends. In this effort, we have investigated the selectivity of softwood kraft lignin toward esterification via acylation. LignoBoost kraft lignin was esterified with acetyl (C-2), octanoyl (C-8), lauroyl (C-12), and palmitoyl (C-16) chlorides at various molar ratios with respect to the total hydroxyls present. Quantitative P-31 NMR spectroscopy, Fourier transform infrared spectroscopy (FTIR), and gel permeation chromatography (GPC) were used to evaluate the selectivity and efficiency of these reactions on the various hydroxyl groups present. The C-8-C-16 acyl chlorides showed distinct enhanced reactivity toward the aliphatic hydroxyl groups, whereas C-2 acyl chloride was found to react uniformly with any available OH irrespective of their chemical nature. The effects of long chain acylation on the polymer and material properties were also examined using solution viscosity, thermal, and rheological measurements. Polymer blends were also produced and studied by melt extrusion. The long aliphatic chains when installed on the lignin displayed peculiar association effects in solution and enhanced the melt flow characteristics of the lignin polymer blends.

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