Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis

Zhao, Xiaohong; Zhang, Yanjuan; Wei, Liping; Hu, Huayu; Huang, Zuqiang; Yang, Mei; Huang, Aimin; Wu, Juan; Feng, Zhenfei

doi:10.1039/c7ra10482k

Cited by 39 publications

(26 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Blending at higher temperatures, viz. at 170 and 190 °C revealed a new shoulder around 1759 cm –1 , which is characteristic of ester carbonyls . In the normal preparation conditions of the blends, this shoulder is not detected, suggesting that esterification does not take place.…”

Section: Resultsmentioning

confidence: 99%

Potential of Organosolv Lignin Based Materials in Pressure Sensitive Adhesive Applications

Sivasankarapillai

Eslami

Laborie

2019

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

Blending lignin with other polymers has long been utilized as a potent approach to explore novel applications for lignin. Yet, combinations of organosolv lignin (OSL) with superplasticizer have been hardly explored as a potential to design novel material properties. In this study, a commercial superplasticizer, a polycarboxylate polyether (PCE) is blended with a beech-based organosolv lignin, and their miscibility and adhesive properties are studied over the entire compositional range. All blend compositions exhibit a single glass transition temperature (T g) that follows the Kwei model of miscible polymer blends, while a thermal stabilization effect is evidenced in blends containing up to 50% lignin. Fourier transform infrared spectroscopy (FTIR) investigations reveal specific interactions between functional groups in PCE and lignin OH groups as molecular basis for miscibility. The rheological properties, tackiness, and adhesive peel strength suggest that these blends have potential as a base formulation for pressure sensitive adhesive applications, albeit needing some fine-tuning.

show abstract

Section: Resultsmentioning

confidence: 99%

Potential of Organosolv Lignin Based Materials in Pressure Sensitive Adhesive Applications

Sivasankarapillai

Eslami

Laborie

2019

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…3a). 23,26,[50][51][52][53][54][55][56][57][58] Many of these chemical modifications have attempted to convert lignin macromolecules into macromonomers and subsequently graft classical monomers or polymers, and in this way, synthetize ligninbased functional polymers. 23,[26][27][28] Well-defined lignin graft copolymers can be elaborated by two main methodologies: ''grafting from'' and ''grafting to'' ( Fig.…”

Section: Roadmap To Lignin-based Smart Materialsmentioning

confidence: 99%

Lignin-based smart materials: a roadmap to processing and synthesis for current and future applications

2020

View full text Add to dashboard Cite

show abstract

“…The highest conversion of K1 HH and yields of PhOH and PhCOOH were obtained in acetic acid (Table 2, entry 3). However, lignin is rich of alcohol moieties that may be esterified by acetic acid, giving rise to a lignin more recalcitrant to oxidation [43]. Consequently, in spite of these results, acetonitrile was preferred to acetic acid provided that some further optimization would be done.…”

Section: K1 Hh Aerobic Cleavagementioning

confidence: 99%

Vanadium-Substituted Phosphomolybdic Acids for the Aerobic Cleavage of Lignin Models—Mechanistic Aspect and Extension to Lignin

2020

View full text Add to dashboard Cite

This work deals with the aerobic oxidative cleavage of C-C and C-O bonds catalyzed by the Keggin-type phosphovanadomolybdic acid (H 6 [PMo 9 V 3 O 40 ], noted H 6 PV 3 ). The latter was synthesized by an adapted hydrothermal procedure classically used for lower vanadium content and was tested as a catalyst for the aerobic cleavage of 2-phenoxyacetophenone (noted K1 HH ) and 1-phenyl-2-phenoxyethanol (A1 HH ) used as two lignin models. The operative conditions (solvent, catalytic loading, etc.) were adjusted on K1 HH and extrapolated to A1 HH . The cleavage of the alcohol model required more drastic conditions and therefore further optimization. Preliminary attempts on an Organosolv wheat straw lignin were performed too. From the kinetic study, high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) data, a mechanism of the cleavage of both models was proposed.

show abstract

Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis

Abstract: Four lignin model compounds were used in the reaction with acetic anhydride, with 4-dimethyl amino pyridine, sodium acetate, and sulfuric acid as catalysts to learn about the esterification mechanism of lignin by MASPS technology.

Cited by 39 publications

References 35 publications

Potential of Organosolv Lignin Based Materials in Pressure Sensitive Adhesive Applications

Potential of Organosolv Lignin Based Materials in Pressure Sensitive Adhesive Applications

Lignin-based smart materials: a roadmap to processing and synthesis for current and future applications

Vanadium-Substituted Phosphomolybdic Acids for the Aerobic Cleavage of Lignin Models—Mechanistic Aspect and Extension to Lignin

Contact Info

Product

Resources

About