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01-04-2012 | Issue 2/2012

Simple synthesis of mixed cellulose acylate phosphonates applying n-propyl phosphonic acid anhydride

Journal:: Cellulose > Issue 2/2012

Authors:: Thomas Heinze, Velina Sarbova, Matilde Calado Vieira Nagel

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Important notes

Thomas Heinze—Member of the European Polysaccharide Network of Excellence (EPNOE). http://www.epnoe.de.eu.

Abstract

Cellulose mixed esters containing alkylphosphonate and carboxylate groups were prepared homogeneously by a new one-pot method using n-propyl phosphonic acid anhydride (T3P^®) in LiCl/N-methyl-2-pyrrolidone (NMP). n-Propyl phosphonic acid anhydride acts as both an activating agent for carboxylic acids and phosphonation reagent. Cellulose mixed esters with DS_acyl ranging from 1.4 to 1.8, and DS_phos up to 0.7 could be prepared. The structure of the cellulose mixed esters was elucidated by FTIR- and NMR spectroscopy, as well as by GPC and solubility tests.

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Edgar KJ, Buchanan CM, Debenham JS, Rundquist PA, Seiler BD, Shelton MC, Tindall D (2001) Advances in cellulose ester performance and application. Prog Polym Sci 26:1605–1688 CrossRef

Glasser WG (2004) Prospects for future applications of cellulose acetate. Macromol Symp 208:371–394 CrossRef

Glasser WG, Becker U, Todd JG (2000) Novel cellulose derivatives. Part VI. Preparation and thermal analysis of two novel cellulose esters with fluorine-containing substituents. Carbohydr Polym 42:393–400 CrossRef

Gräbner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9:193–201 CrossRef

Granja PL, De Jéso B, Bareille R, Rouais F, Baquey C, Barbosa MA (2006) Cellulose phosphates as biomaterials. In vitro biocompatibility studies. React Funct Polym 66:728–739 CrossRef

Heinze T, Liebert T, Koschella A (2006) Esterification of polysaccharides. Springer, Berlin

Holla W, Napierski B, Rebenstock HP (1999) Preparation of imidazole derivatives, useful as intermediates for angiotensin II receptor antagonists, by cyclization of aminoacrylate esters. DE 19802969. CAN 131:131507

Hussain MA, Liebert T, Heinze T (2004) Acylation of cellulose with N,N′-carbonyldiimidazole-activated acids in the novel solvent dimethyl sulfoxide/tetrabutylammonium fluoride. Macromol Rapid Commun 25:916–920 CrossRef

Inagaki N, Katsuura K (1980) Reaction of cellulose phosphonate with N-Vinyl-2- pyrrolidone and flame-retardant properties of the product. J Polym Sci Polym Chem Ed 18:441–448 CrossRef

Meudt A, Scherer S, Nerdinger S (2005) Method for producing nitriles and isonitriles by using dehydration reactors with propanephosphonic anhydrides. WO 2005070879. CAN 143:172649

Monge S, Cannicioni B, Graillot A, Robin JJ (2011) Phosphorus-containing polymers: a great opportunity for the biomedical field. Biomacromolecules 12:1973–1982 CrossRef

Nagel MCV, Heinze T (2010) Esterification of cellulose with acyl-1 H-benzotriazole. Polym Bul 65:873–881 CrossRef

Nehls I, Loth F (1991) ¹³C-NMR-spektroskopische untersuchungen zur phosphatierung von celluloseprodukten im system H ₃PO ₄/harnstoff. Acta Polym 42:233–235 CrossRef

Nuessle AC, Ford FM, Hall WP, Lippert AL (1956) Some aspects of the cellulose-phosphate-urea reaction. Text Res J 26:32–39 CrossRef

Pieschel F, Lange E, Camacho J, Fieseler C, Ikier H (1999) Biosorbents and process for producing the same. WO 9928372. CAN 131:33163

Samaranayake G, Glasser WG (1993) Cellulose derivatives with low DS. I. A novel acylation system. Carbohydr Polym 22:1–7 CrossRef

Sealey JE, Frazier CE, Samaranayake G, Glasser WG (2000) Novel cellulose derivatives. V. Synthesis and thermal properties of esters with trifluoroethoxy acetic acid. J Polym Sci Part B Polym Phys 38:486–494 CrossRef

Shimizu Y, Hayashi J (1988) A new method for cellulose acetylation with acetic acid. Sen-I Gakkaishi 44:451–456 CrossRef

Tesoro GC, Sello SB, Willard JJ (1968) Flame-retardant properties of phosphonate derivatives of cotton cellulose. Text Res J 38:245–255 CrossRef

Touey GP (1956) Preparation of cellulose phosphates. US 2759924. CAN 51:3440

Tsang J, Madden O, Coughlin M, Maiorana A, Watson J, Little NC, Speakman RJ (2009) Degradation of ‘Lumarith’ cellulose acetate. Stud Conserv 54:90–105

Ueda M, Honma T (1988) Synthesis of polyamides by direct polycondensation with propylphosphonic anhydride as an activating agent. Polym J 20:477–483 CrossRef

Vasantha B, Hemantha HP, Sureshbabu VV (2010) 1-Propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the lossen rearrangement: application to the synthesis of urea and carbamate derivatives. Synthesis 17:2990–2996

Vigo TL, Welch CM (1973) Recent advances in the reaction of cotton. Textilveredlung 8:93–97

Wedel M, Walter A, Montforts FP (2001) Synthesis of metalloporphyrins and metallochlorins for immobilization on electrode surfaces. Eur J Org Chem 2001:1681–1687 CrossRef

Wissmann H (1987) Synthesis of peptides and amides with alkylphosphonic-and dialkylphosphinic anhydrides. Phosphorous Sulfur 30:645–648 CrossRef

Wissmann H, Kleiner HJ (1980) New peptide synthesis. Angew Chem Int Ed 19:133–134 CrossRef

Title: Simple synthesis of mixed cellulose acylate phosphonates applying n-propyl phosphonic acid anhydride
Authors:: Thomas Heinze
Velina Sarbova
Matilde Calado Vieira Nagel
Publication date: 01-04-2012
DOI: https://doi.org/10.1007/s10570-011-9646-4
Publisher: Springer Netherlands
Journal: Cellulose
Issue 2/2012
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X

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