Studies on regioselective acylation of cellulose with bulky acid chlorides

Cellulose

Volumn 18, Issue 2, 2011, Pages 405-419

  Xu, Daiqiang ^a   Li, Bin ^a   Tate, Courtney ^a   Edgar, Kevin J ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Cellulose 2,4,6 trimethylbenzoate; Cellulose adamantate; Cellulose pivalate; Distribution pattern; Mesitoyl cellulose; NMR spectroscopy; Regioselective acylation; Regioselective substitution

Indexed keywords

DISTRIBUTION PATTERN; MESITOYL CELLULOSE; NMR SPECTROSCOPY; REGIOSELECTIVE ACYLATION; REGIOSELECTIVE SUBSTITUTION;

ACYLATION; CHLORINE COMPOUNDS; ESTERIFICATION; ESTERS; IONIC LIQUIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REGIOSELECTIVITY;

CELLULOSE;

EID: 79952538700     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-010-9476-9     Document Type: Article

References (44)

1. Cai S, Hakomori S, Toyokuni T (1992) Application of protease-catalyzed regioselective esterification in synthesis of 6′-deoxy-6′-fluoro- and 6-deoxy-6-fluorolactosides. J Org Chem 57(12): 3431-3437.
2. Camacho Gomez JA, Erler UW, Klemm DO (1996) 4-Methoxy substituted trityl groups in 6-O protection of cellulose: homogeneous synthesis, characterization, detritylation. Macromol Chem Phys 197(3): 953-964.
3. Chan BKM, Chang N-H, Grimmett MR (1977) The synthesis and thermolysis of imidazole quaternary salts. Aust J Chem 30(9): 2005-2013.
4. Corey EJ, Achiwa K, Katzenellenbogen JA (1969) Total synthesis of dl-sirenin. J Am Chem Soc 91(15): 4318-4320.
5. Dawsey TR, McCormick CL (1990) The lithium chloride/dimethylacetamide solvent for cellulose: a literature review. Polym Rev 30: 405-440.
6. Edgar KJ, Arnold KM, Blount WW, Lawniczak JE, Lowman DW (1995) Synthesis and properties of cellulose acetoacetates. Macromolecules 28(12): 4122-4128.
7. Einfeldt L, Guenther W, Klemm D, Heublein B (2005) Peracetylated cellulose: end group modification and structural analysis by means of 1H-NMR spectroscopy. Cellulose 12(1): 15-24.
8. El Seoud OA, Koschella A, Fidale LC, Dorn S, Heinze T (2007) Applications of ionic liquids in carbohydrate chemistry: a window of opportunities. Biomacromolecules 8(9): 2629-2647. doi: 10. 1021/bm070062i.
9. Graebner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9(2): 193-201.
10. Granstroem M, Kavakka J, King A, Majoinen J, Maekelae V, Helaja J, Hietala S, Virtanen T, Maunu S-L, Argyropoulos DS, Kilpelaeinen I (2008) Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride. Cellulose 15(3): 481-488.
11. Hattori A, Kawahara T, Uemoto T, Suzuki F, Tada H, Ito S (2000) Ultrathin SiOx film coating effect on the wettability change of TiO2 surfaces in the presence and absence of UV light illumination. J Colloid Interface Sci 232(2): 410-413.
12. Heinze T (2004) Chemical functionalization of cellulose. Dumitriu polysaccharides 551-590.
13. Heinze T, Liebert T (2001a) Unconventional methods in cellulose esterification. Prog Polym Sci 26: 1689-1762.
14. Heinze T, Liebert T (2001b) Unconventional methods in cellulose functionalization. Prog Polym Sci 26(9): 1689-1762.
15. Heinze T, Dicke R, Koschella A, Kull AH, Klohr E-A, Koch W (2000) Effective preparation of cellulose derivatives in a new simple cellulose solvent. Macromol Chem Phys 201(6): 627-631.
16. 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(9): 916-920.
17. Iwata IO T, Okamura K, Azuma J, Tanaka F (1996) Molecular and crystal structure of cellulose acetate dipropanoate (CADP, 6-O-Acetyl-2, 3-di-O-propanoyl cellulose). Cellulose 3: 107-124.
18. Iwata K, Azuma J, Tanaka F (1996) Molecular and crystal structure of cellulose propanoate diacetate (CPDA, 2, 3-Di-O-acetyl-O-propanoyl cellulose). Cellulose 3: 91-106.
19. Iwata T, Azuma J, Okamura K, Muramoto M, Chun B (1992) Preparation and NMR assignments of cellulose mixed esters regioselectively substituted by acetyl and propanoyl groups. Carbohydr Res 224: 277-283.
20. Iwata T, Fukushima A, Okamura K, Azuma J (1997) DSC study on regioselectively substituted cellulose heteroesters. J Appl Polym Sci 65: 1511-1515.
21. Kamide K, Saito M (1994) Recent advances in molecular and supermolecular characterization of cellulose and cellulose derivatives. In: Macromolecular symposia 83 (international conference on advanced polymer materials, 1993), pp 233-271.
22. Klemm DO (1998) Regiocontrol in cellulose chemistry: principles and examples of etherification and esterification. In: ACS symposium series 688 (cellulose derivatives), pp 19-37.
23. Klemm D, Heinze T, Philipp B, Wagenknecht W (1997) New approaches to advanced polymers by selective cellulose functionalization. Acta Polym 48: 277-297.
24. Kohler S, Heinze T (2007) New solvents for cellulose: dimethyl sulfoxide/ammonium fluorides. Macromol Biosci 7(3): 307-314. doi: 10. 1002/mabi. 200600197.
25. Koschella A, Klemm D (1997) Silylation of cellulose regiocontrolled by bulky reagents and dispersity in the reaction media. In: Macromolecular symposia 120 (functional polysaccharides II), pp 115-125.
26. 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(1): 49-54.
27. Liang T-s, Hu Y-l (2007) Preparation of 2, 4, 6-trimethylbenzoyl chloride. Huaxue Gongchengshi 21(11): 11-12.
28. Liebert T, Heinze T (2005) Tailored cellulose esters: synthesis and structure determination. Biomacromolecules 6: 333-340.
29. Liebert T, Wotschadlo J, Gericke M, Kohler S, Laudeley P, Heinze T (2009) Modification of cellulose in ionic liquids towards biomedical applications. In: Edgar KJ, Heinze T, Buchanan CM (eds) Polysaccharide materials: performance by design, vol 1017. American Chemical Society, Washington, DC.
30. Liebert T, Heinze TL, Edgar KJ (2010) Cellulose solvents: for analysis, shaping, and chemical modification. In: ACS symposium series, vol 1033. American Chemical Society, Washington, DC.
31. Matsushita Y-I, Sugamoto K, Kita Y, Matsui T (1997) Silica gel-catalyzed beta-O-glucosylation of alcohols with 1, 2-anhydro-3, 4, 6-tri-O-pivaloyl-alpha-d-glucopyranose. Tetrahedron Lett 38(50): 8709-8712.
32. Oestlund A, Lundberg D, Nordstierna L, Holmberg K, Nyden M (2009) Dissolution and gelation of cellulose in TBAF/DMSO solutions: the roles of fluoride ions and water. Biomacromolecules 10(9): 2401-2407.
33. Petzold K, Koschella A, Klemm D, Heublein B (2003) Silylation of cellulose and starch-selectivity, structure analysis, and subsequent reactions. Cellulose 10(3): 251-269.
34. Rao CB, Chinnababu B, Venkateswarlu Y (2009) An efficient protocol for alcohol protection under solvent- and catalyst-free conditions. J Org Chem 74(22): 8856-8858.
35. Sakairi N, Nomura K, Nishi N, Tokhura S (1997) A novel procedure for the preparation of fully 6-O-pivaloylated derivatives of cyclodextrin. Carbohydr Lett 2(4): 253-258.
36. Schlufter K, Schmauder H-P, Dorn S, Heinze T (2006) Efficient homogeneous chemical modification of bacterial cellulose in the ionic liquid 1-N-butyl-3-methylimidazolium chloride. Macromol Rapid Commun 27(19): 1670-1676.
37. Schnabelrauch M, Vogt S, Klemm D, Nehls I, Philipp B (1992) Readily hydrolyzable cellulose esters as intermediates for the regioselective derivatization of cellulose. Die Angewandte Makromolekulare Chemie 198: 155-164.
38. Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun (23): 2399-2407.
39. Silverstein RM, Webster FX, Kiemle DJ (2005) Spectrometric identification of organic compounds 87-88.
40. Sun H, DiMagno SG (2005) Anhydrous tetrabutylammonium fluoride. J Am Chem Soc 127(7): 2050-2051. doi: 10. 1021/ja0440497.
41. Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124(18): 4974-4975.
42. Takimoto S, Inanaga J, Katsuki T, Yamaguchi M (1976) Preparation of hindered esters from acid chlorides and alcohols in the presence of silver cyanide. Bull Chem Soc Japan 49(8): 2335-2336.
43. Tasaka K et al (2007) Cellulose ester film, its manufacturing method, optical retardation film, optical compensation sheet, elliptic polarizing plate, and image display. US Patent.
44. Tsunashima Y, Hattori K (2000) Substituent distribution in cellulose acetates: its control and the effect on structure formation in solution. J Colloid Interface Sci 228(2): 279-286.