Abstract
Cellulose, (1→4)-β-d-glucopyranan, was for the first time synthesized by cationic ring-opening polymerization of 3,6-di-O-benzyl-α-d-glucose 1,2,4-orthopivalate (5) into 3,6-di-O-benzyl-2-O-pivaloyl-β-d-glucopyranan (6) and subsequent removal of the protective groups. Polymerization of the orthoester 5 by triphenyl carbenium tetrafluoroborate gave 3,6-di-O-benzyl-2-O-pivaloyl-β-d-glucopyranan with [α]D −37.2° and a number-average molecular weight of 8.3 × 103 ( = 19.3). Removal of the pivaloyl and benzyl groups and subsequent acetylation gave acetylated (1→4)-β-d-glucopyranan which was completely identical with cellulose triacetate (CTA) prepared from low molecular weight cellulose. The synthesized CTA was converted by deacetylation to cellulose, which has the cellulose-II crystal structure.
Keywords
ChemistryCationic polymerizationCellulose triacetateCellulosePolymer chemistryPolymerizationOrthoesterRing-opening polymerizationAcetylationTetrafluoroborateRing (chemistry)Organic chemistryPolymerIonic liquidCatalysis
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Publication Info
- Year
- 1996
- Type
- article
- Volume
- 118
- Issue
- 7
- Pages
- 1677-1681
- Citations
- 126
- Access
- Closed
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Cite This
Fumiaki Nakatsubo,
Hiroshi Kamitakahara,
Michiko Hori
(1996).
Cationic Ring-Opening Polymerization of 3,6-Di-<i>O</i>-benzyl-α-<scp>d</scp>-glucose 1,2,4-Orthopivalate and the First Chemical Synthesis of Cellulose.
Journal of the American Chemical Society
, 118
(7)
, 1677-1681.
https://doi.org/10.1021/ja953286u
Identifiers
- DOI
- 10.1021/ja953286u