Substituent Distribution in Cellulose Acetates: Its Control and the Effect on Structure Formation in Solution

Tsunashima, Yoshisuke; Hattori, K.

doi:10.1006/jcis.2000.6952

Cited by 16 publications

(10 citation statements)

References 31 publications

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“…The crystal structures of both 6- O -acetyl-2,3-di- O -propionyl-cellulose and 6- O -propionyl-2,3-di- O -acetyl-cellulose were determined by X-ray and electron diffraction analyses, and the samples were further examined by atomic force microscopy and DSC . Regioselectively acetylated trityl cellulose was also used to investigate the solution behavior of cellulose esters in polar solvents. , It was observed that the position of the ester substituents has a large influence on the cellulose chain conformations and associations in solution. Kasuya et al investigated 6- O -acetyl-2,3-di- O -benzoyl-cellulose and 2,3-di- O -acetyl-6- O -benzoyl-cellulose as stationary phases for chiral separations and found that the location of the specific substituents significantly affected chiral discrimination.…”

Section: Reaction Of Cellulose With Bulky Reagentsmentioning

confidence: 99%

Regioselective Esterification and Etherification of Cellulose: A Review

et al. 2011

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Deep understanding of the structure-property relationships of polysaccharide derivatives depends on the ability to control the position of the substituents around the monosaccharide ring and along the chain. Equally important is the ability to analyze position of substitution. Historically, both synthetic control and analysis of regiochemistry have been very difficult for cellulose derivatives, as for most other polysaccharide derivatives. With the advent of cellulose solvents that are suitable for chemical transformations, it has become possible to carry out cellulose derivatization under conditions sufficiently mild to permit increasingly complete regiochemical control, particularly with regard to the position of the substituents around the anhydroglucose ring. In addition, new techniques for forming cellulose and its derivatives from monomers, either by enzyme-catalyzed processes or chemical polymerization, permit us to address new frontiers in regiochemical control. We review these exciting developments in regiocontrolled synthesis of cellulose derivatives and their implications for in-depth structure-property studies.

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Section: Reaction Of Cellulose With Bulky Reagentsmentioning

confidence: 99%

Regioselective Esterification and Etherification of Cellulose: A Review

et al. 2011

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“…[10] In addition, investigations of the structure in solution revealed large differences to cellulose esters with random distribution of substituents, e.g., the chain conformation, solubility, and clustering mechanism may be different. [11,12] In a comparable way, the preparation of cellulose sulfuric acid half esters with preferred functionalization of the secondary OH functions was achieved. [13] Sulfur trioxide pyridine complex was used as reagent followed by detritylation.…”

Section: Triphenylmethyl Ethers and Subsequent Productsmentioning

confidence: 99%

Regioselectively Functionalized Cellulose Derivatives: A Mini Review

Koschella

Fenn

Illy

et al. 2006

Macromolecular Symposia

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The paper reviews recent developments in synthesis and characterization of regioselectively functionalized cellulose derivatives. It demonstrates the importance of protecting groups like triphenylmethyl-and thexyldimethylsilyl (TDMS) ethers in cellulose chemistry. The protected cellulose derivatives can be used for the preparation of 2,3-O-functionalized polymers. Moreover, the TDMS group opens up the synthesis of 3-O-ethers of cellulose that possess interesting properties in terms of structure in solution, water-solubility, and thermoreversible gelation.

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“…The thickness is 29 nm for 2,3-di-O-acetyl-6-mono-O-propionyl cellulose and 45 nm for 6-mono-O-acetyl-2,3-di-O-propionyl cellulose. The dynamic structures formed in polar solvents of regioselectively substituted cellulose ester samples can be compared with those of commercial cellulose esters with random distribution, revealing large differences in the chain conformation, the solubility, and the clustering mechanism and structures [436,437].…”

Section: Tritylationmentioning

confidence: 99%