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Organic Esters of Cellulose: New Perspectives for Old Polymers

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Polysaccharides I

Part of the book series: Advances in Polymer Science ((POLYMER,volume 186))

Abstract

The impetus for the increased interest in the synthesis of functionalized natural polymers, in particular esters of cellulose, is their easy biodegradability and conformity to the principles of green chemistry. This review is concerned with the preparation of cellulose esters under homogeneous reaction conditions, including products that cannot be obtained by the (industrial) heterogeneous reaction. This scheme, which leads to products of reproducible properties, includes three stages: Cellulose activation (by solvent exchange or heat), dissolution (in derivatizing or non-derivatizing solvent systems), and functionalization of the solubilized polymer. Dissolution in non-derivatizing solvent systems, in particular LiCl/DMAc; (C4H9)4NF ·hydrate/DMSO and ionic liquids (green solvents) is due to the disruption of the H-bonding within the polymer structure. Dissolution in derivatizing solvents, e.g., acid-anhydrides leads to functionalization of cellulose, and may be fruitfully employed in controlling the regioselectivity of polymer substitution. Optimization of each of the above-mentioned reaction stages is a pre-requisite in order to meet the requirements of green chemistry.

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Abbreviations

AGU:

anhydroglucose unit of cellulose

CA:

cellulose acetate

CDI:

N,N-carbonyldiimidazole

Cell:

cellulose

Cell-Tos:

cellulose tosylate

CMC:

carboxymethyl cellulose

DCC:

dicyclohexylcarbodiimide

DMAc:

N,N-dimethylacetamide

DMF:

N,N-dimethylformamide

DMSO:

dimethyl sulfoxide

DS:

average degree of substitution in the AGU

DSC:

differential scanning calorimetry

Et3N:

triethylamine

EWNN:

alkaline solution of iron sodium tartarate

HEC:

hydroxyethylcellulose

HRC:

homogenous reaction conditions

Ic:

index of crystallinity of cellulose

IL:

ionic liquid

LS:

light scattering

Py:

pyridine

SEC:

size exclusion chromatography

TBAF:

tetra-n-butyl ammonium fluoride·3H2O

TFA:

trifluoroacetic acid

Tos-Cl:

tosyl chloride

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  1. Instituto de Química, Universidade de São Paulo, C.P. 26077, 05513-970, São Paulo, S.P., Brazil

    Omar A. El Seoud

  2. Friedrich Schiller University of Jena, Humboldtstrasse 10, D-07743, Jena, Germany

    Thomas Heinze

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El Seoud, O.A., Heinze, T. Organic Esters of Cellulose: New Perspectives for Old Polymers . In: Heinze, T. (eds) Polysaccharides I. Advances in Polymer Science, vol 186. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136818

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