TBAF and cellulose esters: unexpected deacylation with unexpected regioselectivity.

Biomacromolecules

Department of Wood Science and Forest Products, and Macromolecules and Interfaces Institute, Virginia Tech , 230 Cheatham Hall, Blacksburg, Virginia 24061, United States.

Published: February 2012

Tetrabutylammonium fluoride has been found to catalyze the deacylation of cellulose esters. More surprisingly, the deacylation is highly regioselective. Even more remarkably, in contrast with the C-6 regioselectivity of other reactions of cellulose and its derivatives, this deacylation shows substantial selectivity for the removal of the acyl groups from the esters of the secondary alcohols at C-2 and C-3, affording cellulose-6-O-esters with high regioselectivity by a simple one-step process employing no protective groups.

Download full-text PDF

Source
http://dx.doi.org/10.1021/bm201724sDOI Listing

Publication Analysis

Top Keywords

cellulose esters
8
tbaf cellulose
4
esters unexpected
4
deacylation
4
unexpected deacylation
4
deacylation unexpected
4
unexpected regioselectivity
4
regioselectivity tetrabutylammonium
4
tetrabutylammonium fluoride
4
fluoride catalyze
4

Similar Publications

Interfacial solar vapor generation (ISVG) accompanied by photocatalytic degradation holds immense potential to mitigate water scarcity and pollution. Distinct from the two detached functional components (photothermal agent and photocatalyst) in a conventional evaporator, in this study, an all-in-one photothermal/catalytic agent, nitrogen-containing honeycomb carbon nanosheets (NHC), was engineered for synergistic high-efficiency steam generation and photocatalysis functions. It was demonstrated that the superoxide radical generated on the surface of NHC conferred its catalytic activity to the photodegradation of organic pollutants under full solar spectrum irradiation.

View Article and Find Full Text PDF

This study explored a facile method for converting macadamia nutshells into bio-based nanomaterials, including cellulose nanofibers (CNFs) and lignin nanoparticles (LNPs), through deep eutectic solvent (DES) pretreatment coupled with a nanofabrication strategy. Comparisons of the physicochemical, morphological, and structural properties of the CNF and LNPs produced through acidic choline chloride/oxalic acid dihydrate (ACDES) and alkaline KCO/glycerol DES (ALDES) pretreatments were conducted using SEM, TEM, FTIR, XRD, TGA, GPC and 2D NMR. The CNFs obtained from ACDES pretreatment (ACCNFs) exhibited uniform and long filament-like structures with shorter whisker-like nanocrystals.

View Article and Find Full Text PDF

In this study, we prepared a new multi-functional intelligent hydrogel preservation film using soy hull nanocellulose (SHNC), polyvinyl alcohol (PVA), chitosan (CS), and anthocyanin (Anth) as raw materials. The physicochemicals of the hydrogel preservation film, and its role in monitoring the freshness and freshness of salmon was evaluated. The results showed that the monomers were crosslinked by hydrogen, ester bonds, and electrostatic interactions in the hydrogel film, and there were three-dimensional pores in the hydrogel film.

View Article and Find Full Text PDF

Efficient and accurate determination of the degree of substitution of cellulose acetate using ATR-FTIR spectroscopy and machine learning.

Sci Rep

January 2025

Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT), Karlsruhe, 76344, Germany.

Multiple linear regression models were trained to predict the degree of substitution (DS) of cellulose acetate based on raw infrared (IR) spectroscopic data. A repeated k-fold cross validation ensured unbiased assessment of model accuracy. Using the DS obtained from H NMR data as reference, the machine learning model achieved a mean absolute error (MAE) of 0.

View Article and Find Full Text PDF

Synthesis and characterization of thermoplastic resin from sugar beet polysaccharides via one-step transesterification.

Carbohydr Polym

March 2025

Institute of Science and Engineering, Kanazawa University, Kakuma machi, Kanazawa 920 1192, Japan. Electronic address:

Lignocellulosic biomass-based plastics provide a sustainable alternative to petroleum-based plastics by converting agricultural by-products into value-added materials, promoting a circular economy. This study investigates the development of thermoplastics from sugar beet pulp (SBP), a by-product rich in cellulose and pectin. A one-pot direct transesterification process was used to fully substitute hydroxy groups in SBP with acyl chains of varying lengths (C2-C10), achieving up to 96 % substitution.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!