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Novel 3-mono-O-hydroxyethyl cellulose: synthesis and structure characterization

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Abstract

The synthesis of 3-mono-O-hydroxyethyl cellulose using orthogonal protecting groups was realized. The reaction of 2,6-di-O-thexyldimethylsilyl cellulose with 2-(2-bromoethoxy)tetrahydropyran leads to a completely functionalized cellulose derivative. The complete removal of the protecting groups was possible by split off of the TDMS functions with tetrabutylammonium fluoride trihydrate and subsequently the tetrahydropyran moieties with hydrochloric acid. The structure of 3-mono-O-hydroxyethyl cellulose was confirmed by applying one and two-dimensional NMR spectroscopy. The novel polymer is soluble in water and does not show thermoreversible gelation.

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References

  • Arisawa M, Kato C, Kaneko H, Nishida A, Nakagawa M (2000) Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM). J Chem Soc Perkin Trans 1 12:1873–1876. doi:10.1039/b002117m

    Article  Google Scholar 

  • Bar-Nir BB-A, Kadla JF (2009) Synthesis and structural characterization of 3-O-ethylene glycol functionalized cellulose derivatives. Carbohydr Polym 76:60–67. doi:10.1016/j.carbpol.2008.09.026

    Article  Google Scholar 

  • Brandt L (1986) In: Gerhartz W, Yamamoto YS, Campbell FT, Pfefferkorn R, Rounsaville JF (eds) Ullmann’s encyclopedia of industrial chemistry, vol A5. VCH, Weinheim, p 461

    Google Scholar 

  • Fenn D, Pfeifer A, Heinze T (2007) Studies on the synthesis of 2,6-di-O-thexyldimethylsilyl cellulose. Cellul Chem Technol 41:87

    CAS  Google Scholar 

  • Heinze T, Koschella A (2008) Water-soluble 3-O-methoxyethyl cellulose: synthesis and characterization. Carbohydr Res 343:668. doi:10.1016/j.carres.2008.01.018

    Article  CAS  Google Scholar 

  • Heinze T, Petzold K (2008) Cellulose chemistry: novel products and synthesis paths. In: Belgacem MN, Gandini A (eds) Monomers, oligomers, polymers, composites from renewable resources. Elsevier, Oxford, pp 343–368

    Chapter  Google Scholar 

  • Heinze T, Pfeifer A, Petzold K (2008) Regioselective reaction of cellulose with tert-butyldimethylsilyl chloride in N,N-dimethyl acetamide/LiCl. BioResources 3:79

    CAS  Google Scholar 

  • Kadla JF, Asfour FH, Bar-Nir B (2007) Micropatterned thin film honeycomb materials from regiospecifically modified cellulose. Biomacromolecules 8:161. doi:10.1021/bm060808x

    Article  CAS  Google Scholar 

  • Koschella A, Heinze T, Klemm D (2001) First synthesis of 3-O-functionalized cellulose ethers via 2,6-di-O-protected silyl cellulose. Macromol Biosci 1:49. doi:10.1002/1616-5195(200101)1:1<49::AID-MABI49>3.0.CO;2-C

    Article  CAS  Google Scholar 

  • Koschella A, Fenn D, Heinze T (2006a) Water soluble 3-mono-O-ethyl cellulose: synthesis and characterization. Polym Bull 57:33. doi:10.1007/s00289-006-0534-2

    Article  CAS  Google Scholar 

  • Koschella A, Fenn D, Illy N, Heinze T (2006b) Regioselectively functionalized cellulose derivatives: a mini review. Macromol Symp 244:59. doi:10.1002/masy.200651205

    Article  CAS  Google Scholar 

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Acknowledgments

We are indebted to Dr. W. Günther for conducting the NMR experiments. The authors thank the Fachagentur Nachwachsende Rohstoffe (FNR)/BMVEL (project. no. 22003504 04NR035) for generous financial support. D. Fenn wishes to thank Dr. K. Petzold-Welcke and Dr. A. Koschella for helpful discussions regarding the synthesis.

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  1. Kompetenzzentrum Polysaccharidforschung, Friedrich-Schiller-Universität Jena, Humboldtstraße 10, 07743, Jena, Germany

    Dominik Fenn & Thomas Heinze

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  1. Dominik Fenn
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  2. Thomas Heinze
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Correspondence to Thomas Heinze.

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Fenn, D., Heinze, T. Novel 3-mono-O-hydroxyethyl cellulose: synthesis and structure characterization. Cellulose 16, 853–861 (2009). https://doi.org/10.1007/s10570-009-9297-x

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