Tosyl hóa và acyl hóa cellulose trong 1-allyl-3-methylimidazolium chloride

Springer Science and Business Media LLC - Tập 15 - Trang 481-488 - 2008
Mari Granström1, Jari Kavakka1, Alistair King1, Johanna Majoinen1, Valtteri Mäkelä1, Juho Helaja2, Sami Hietala3, Tommi Virtanen3, Sirkka-Liisa Maunu3, Dimitris S. Argyropoulos4, Ilkka Kilpeläinen1
1Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, Helsinki, Finland
2Department of Chemistry, University of Helsinki, Helsinki, Finland
3Laboratory of Polymer Chemistry, Department of Chemistry, University of Helsinki, Helsinki, Finland
4Organic Chemistry of Wood Components Laboratory, North Carolina State University, Raleigh, USA

Tóm tắt

Tosyl hóa và acyl hóa cellulose được thực hiện dưới các điều kiện phản ứng nhẹ nhàng bằng cách sử dụng các dung môi là các chất lỏng ion imidazolium (ILs). Tính chất không phân hủy, độ nhớt thấp cũng như khả năng hòa tan cao của cellulose trong [amim]Cl đã khuyến khích chúng tôi thực hiện các phản ứng trong môi trường này. Các phản ứng được mô tả ở đây đã được tối ưu hóa cho dung môi cụ thể này nhằm thu được các dẫn xuất cellulose khác nhau với hiệu suất cao, đồng nhất và mức độ thay thế (DS) cao. Hai chất phản ứng được sử dụng để kích hoạt dạng in situ của axit cacboxylic là N,N′-carbonyldiimidazole (CDI) và 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCI). Các sản phẩm cuối cùng được phân tích bằng các kỹ thuật NMR trong dung dịch và trạng thái rắn.

Từ khóa


Tài liệu tham khảo

Barthel S, Heinze T (2006) Acylation and carbanilation of cellulose in ionic liquids. Green Chem 8:301–306 Bruckner R (2002) Advanced organic chemistry, reaction mechanisms. Harcourt/Academic Press, USA, p 242 Eastman Kodak Co. (1969) Process for strengthening swellable fibrous material with an amine oxide and the resulting material. US3447956 Einfeldt J, Heinze T, Liebert T, Kwasniewski A (2002) Influence of the p-toluenesulphonylation of cellulose on the polymer dynamics investigated by dielectric spectroscopy. Carbohydr Polym 49:357–365 El Seoud OA, Marson AG, Ciacco TG, Frollini E (2000) An efficient, one-pot acylation of cellulose under homogeneous reaction conditions. Macromol Chem Phys 201:882–889 Heinze T, Rahn K, Jaspers M, Berghmans H (1996) Thermal studies on homogeneously synthesized cellulose p-toluenesulfonates. J Appl Polym Sci 60:1891–1900 Heinze T, Liebert T (2001a) Unconventional methods in cellulose functionalization. Prog Polym Sci 26:1689–1726 Heinze T, Rahn K (1997) Cellulose p-toluenesulfonates: a valuable intermediate in cellulose chemistry. Macromol Symp 120:103–113 Heinze T, Dicke R, Koschella A, Henning Kull A, Klohr EA, Koch W (2000) Effective preparation of cellulose derivatives in a new simple cellulose solvent. Macromol Chem Phys 201:627–631 Heinze T, Koschella A, Magdaleno-Maiza L, Ulrich AS (2001b) Nucleophilic displacement reactions on tosyl cellulose by chiral amines. Polym Bull 46:7–13 Heinze T, Liebert T, Pfeiffer K, Hussain M (2003) Unconventional cellulose esters: synthesis, characterization and structure–property relations. Cellulose 10:283–296 Heinze T, Schwikai K, Barthel S (2005) Ionic liquids as reaction medium in cellulose functionalization. Macromol Biosci 5:520–525 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 Iriyama K, Shikari M, Yoshiura M (1979) An improved for extraction, partial purification, separation and isolation of chlorophyll from spinach leaves. J Liq Chromatogr 2:255–276 Kavakka JS, Heikkinen S, Kilpeläinen I, Mattila M, Lipsanen H, Helaja J (2007) Noncovalent attachment of pyro-pheophorbide a to a carbon nanotube. Chem Commun 5:519–521 Kern H, Choi S, Wenz G, Heinrich J, Ehrhardt L, Mischnick P, Garidel P, Blume A (2000) Synthesis, control of substitution pattern and phase transitions of 2,3-di-O-methylcellulose. Carbohydr Res 326:67–79 Kondo T (1997) The relationship between intramolecular hydrogen bonds and certain physical properties of regioselectively substituted cellulose derivatives. J Polym Sci B Polym Phys 35:717–723 Koschella A, Heinze T (2001) Novel regioselectively 6-functionalized cationic cellulose polyelectrolytes prepared via cellulose sulfonates. Macromol Biosci 1:178–184 Koschella A, Heinze T (2003) Unconventional cellulose products by fluorination of tosyl cellulose. Macromol Symp 197:243–245 Krouit M, Granet R, Branland P, Verneuil B, Krausz P (2006) New photoantimicrobial films composed of porphyrinated lipophilic cellulose esters. Bioorg Med Chem Lett 16:1651–1655 Krässig HA (1993) In: Huglin MB (ed) Cellulose, 1st edn, vol 11. Gordon and Breach Science Publishers, Amsterdam, p 31 Liu C, Baumann H (2002) Exclusive and complete introduction of amino groups and their N-sulfo and N-carboxymethyl groups into the 6-position of cellulose without the use of protecting groups. Carbohydr Res 337:1297–1307 Mais U, Binder W, Knaus S, Gruber H (2000) Synthesis and 13C CP MAS NMR spectroscopy of cellulose-graft-poly(N-acetylethylenimine). Macromol Chem Phys 201:2115–2122 McCormick CL, Callais PA (1987) Derivatization of cellulose in lithium chloride and N-N-dimethylacetamide solutions. Polymer 13:2317 Myllymäki V, Aksela R (2005) Dissolution method for lignocellulosic materials. WO2005017001 Rahn K, Diamantoglou M, Klemm D, Heinze T (1996) Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamide/LiCl solvent system. Angew Makromol Chem 238:143–163 Regiani AM, Frollini E, Marson GA, Arantes GA, El Seoud OA (1999) Some aspects of acylation of cellulose under homogeneous solution conditions. J Polym Sci A Polym Chem 37:1357–1363 Samaranayake G., Glasser WG (1993) Cellulose derivatives with low DS-I: a novel acylation system. Carbohydr Polym 22:1–7 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 27:1670–1676 Srokova I, Tomanova V, Ebringerova A, Malovikova A, Heinze T (2004) Water-soluble amphiphilic O-(carboxymethyl)cellulose derivatives – Synthesis and properties. Macromol Mater Eng 289:63–69 Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975 Swatloski R, Rogers R, Holbrey J (2003) WO03/029329 Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2004) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5:266–268 Zhang H, Wu J, Zhang J, He J (2005) 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 38:8272–8277 Zhu S, Wu Y, Chen Q, Yu Z, Wang C, Jin S, Ding Y, Wu G (2006) Dissolution of cellulose with ionic liquids and its application: a mini-review. Green Chem 8:325–327