DataVXCellulosePaper
journal article·2024-02

Chlorination of hydroxyethyl cellulose enables selective functionalization

Chengzhe Gao, Stella P. Petrova, Kevin J. Edgar

Cellulose· Volume 31· Issue 3
Publisher page
Bibliographic record

Abstract

No abstract is available for this record. The assistant can identify its topic from the title, but cannot infer the study’s results.

Source: Not provided · Quality: missing

Research context

OpenAlex topics: Advanced Cellulose Research Studies · Enzyme-mediated dye degradation · Lignin and Wood Chemistry

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (61)

Show source-provided references
1. Abbas K, Amin M, Hussain MA et al (2017) Design, characterization and pharmaceutical/pharmacological applications of ibuprofen conjugates based on hydroxyethylcellulose. RSC Adv 7:50672–50679. https://doi.org/10.1039/c7ra08502h10.1039/c7ra08502h ↗
2. Afratis N, Gialeli C, Nikitovic D et al (2012) Glycosaminoglycans: key players in cancer cell biology and treatment. FEBS J 279:1177–1197. https://doi.org/10.1111/j.1742-4658.2012.08529.x10.1111/j.1742-4658.2012.08529.x ↗
3. Aoki N, Furuhata K-I, Saegusa Y et al (1996) Reaction of 6-bromo-6-deoxycellulose with thiols in lithium bromide-N,N-dimethylacetamide. J Appl Polym Sci 61:1173–1185. https://doi.org/10.1002/(SICI)1097-4628(19960815)61:7%3c1173::AID-APP13%3e3.0.CO;2-Z10.1002/(SICI)1097-4628(19960815)61:7<1173::AID-APP13>3.0.CO;2-Z ↗
4. Aoki N, Fukushima K, Kurakata H et al (1999) 6-Deoxy-6-mercaptocellulose and its S-substituted derivatives as sorbents for metal ions. React Funct Polym 42:223–233. https://doi.org/10.1016/S1381-5148(98)00076-510.1016/S1381-5148(98)00076-5 ↗
5. Arca HC, Mosquera-Giraldo LI, Bi V et al (2018) Pharmaceutical applications of cellulose ethers and cellulose ether Esters. Biomacromol 19:2351–2376. https://doi.org/10.1021/acs.biomac.8b0051710.1021/acs.biomac.8b00517 ↗
6. Berlin P, Klemm D, Tiller J, Rieseler R (2000) A novel soluble aminocellulose derivative type: its transparent film-forming properties and its efficient coupling with enzyme proteins for biosensors. Macromol Chem Phys 201:2070–2082. https://doi.org/10.1002/1521-3935(20001001)201:15%3c2070. (:AID-MACP2070>3.0.CO;2-E)10.1002/1521-3935(20001001)201:15<2070 ↗
7. Bernkop-Schnürch A, Dünnhaupt S (2012) Chitosan-based drug delivery systems. Eur J Pharm Biopharm 81:463–469. https://doi.org/10.1016/J.EJPB.2012.04.00710.1016/J.EJPB.2012.04.007 ↗
8. Cimecioglu AL, Ball DH, Kaplan DL, Huang SH (1994) Preparation of amylose derivatives selectively modified at c-6. 6-amino-6-deoxyamylose. Macromolecules 27:2917–2922. https://doi.org/10.1021/ma00089a00410.1021/ma00089a004 ↗
9. Codera V, Edgar KJ, Faijes M, Planas A (2016) Functionalized celluloses with regular substitution pattern by glycosynthase-catalyzed polymerization. Biomacromol 17:1272–1279. https://doi.org/10.1021/acs.biomac.5b0145310.1021/acs.biomac.5b01453 ↗
10. Dong Y, Edgar KJ (2015) Imparting functional variety to cellulose ethers via olefin cross-metathesis. Polym Chem 6:3816–382710.1039/C5PY00369E ↗
11. Dong Y, Mosquera-Giraldo LI, Taylor LS, Edgar KJ (2016a) Amphiphilic cellulose ethers designed for amorphous solid dispersion via olefin cross-metathesis. Biomacromol 17:454–465. https://doi.org/10.1021/acs.biomac.5b0133610.1021/acs.biomac.5b01336 ↗
12. Dong Y, Mosquera-Giraldo LI, Troutman J et al (2016b) Amphiphilic hydroxyalkyl cellulose derivatives for amorphous solid dispersion prepared by olefin cross-metathesis. Polym Chem 7:4953–4963. https://doi.org/10.1039/c6py00960c10.1039/c6py00960c ↗
13. Dong Y, Matson JB, Edgar KJ (2017) Olefin cross-metathesis in polymer and polysaccharide chemistry: a review. Biomacromol 18:1661–1676. https://doi.org/10.1021/acs.biomac.7b0036410.1021/acs.biomac.7b00364 ↗
14. Dong Y, Mosquera-Giraldo LI, Taylor LS, Edgar KJ (2017b) Tandem modification of amphiphilic cellulose ethers for amorphous solid dispersion via olefin cross-metathesis and thiol-Michael addition. Polym Chem 8:3129–3139. https://doi.org/10.1039/C7PY00228A10.1039/C7PY00228A ↗
15. Edgar KJ, Buchanan CM, Debenham JS et al (2001) Advances in cellulose ester performance and application. Prog Polym Sci 26:1605–1688. https://doi.org/10.1016/S0079-6700(01)00027-210.1016/S0079-6700(01)00027-2 ↗
16. Eissa AM, Khosravi E, Cimecioglu AL (2012) A versatile method for functionalization and grafting of 2-hydroxyethyl cellulose (HEC) via click chemistry. Carbohydr Polym 90:859–869. https://doi.org/10.1016/j.carbpol.2012.06.01210.1016/j.carbpol.2012.06.012 ↗
17. Evano G, Nitelet A, Thilmany P, Dewez DF (2018) Metal-mediated halogen exchange in aryl and vinyl halides: a review. Front Chem 6:11410.3389/fchem.2018.00114 ↗
18. Evans ME, Long L, Parrish FW (1968) Reaction of carbohydrates with methylsulfonyl chloride in N,N-dimethylformamide. Preparation of some methyl 6-chloro-6-deoxyglycosides. J Org Chem 33:1074–1076. https://doi.org/10.1021/jo01267a02810.1021/jo01267a028 ↗
19. Fox SC, Edgar KJ (2012) Staudinger reduction chemistry of cellulose: synthesis of selectively O-acylated 6-amino-6-deoxy-cellulose. Biomacromolecules 13:992–1001. https://doi.org/10.1021/bm201700410.1021/bm2017004 ↗
20. Fox SC, Li B, Xu D, Edgar KJ (2011) Regioselective esterification and etherification of cellulose: a review. Biomacromol 12:1956–1972. https://doi.org/10.1021/bm200260d10.1021/bm200260d ↗
21. Furuhata K, Koganei K, Chang H-S et al (1992) Dissolution of cellulose in lithium bromide-organic solvent systems and homogeneous bromination of cellulose with N-bromosuccinimide-triphenylphosphine in lithium bromide-N,N-dimethylacetamide. Carbohydr Res 230:165–177. https://doi.org/10.1016/S0008-6215(00)90519-610.1016/S0008-6215(00)90519-6 ↗
22. Gao C, Edgar KJ (2019) Efficient synthesis of glycosaminoglycan analogs. Biomacromol 20:608–617. https://doi.org/10.1021/acs.biomac.8b0115010.1021/acs.biomac.8b01150 ↗
23. Gao C, Liu S, Edgar KJ (2018) Regioselective chlorination of cellulose esters by methanesulfonyl chloride. Carbohydr Polym 193:108–118. https://doi.org/10.1016/J.CARBPOL.2018.03.09310.1016/J.CARBPOL.2018.03.093 ↗
24. Gao C, Fisher ZB, Edgar KJ (2019) Azide reduction by DTT or thioacetic acid provides access to amino and amido polysaccharides. Cellul 26:445–462. https://doi.org/10.1007/s10570-018-2195-310.1007/s10570-018-2195-3 ↗
25. Gericke M, Liebert T, Heinze T (2009) Polyelectrolyte synthesis and in situ complex formation in ionic liquids. J Am Chem Soc 131:13220–1322110.1021/ja905003r ↗
26. Heinze T, Liebert T (2001) Unconventional methods in cellulose functionalization. Prog Polym Sci 26:1689–1762. https://doi.org/10.1016/S0079-6700(01)00022-310.1016/S0079-6700(01)00022-3 ↗
27. Heinze T, Liebert T, Andreas Koschella (2006) Esterification of polysaccharides. Springer, Cham
28. Joubert F, Yeo RP, Sharples GJ et al (2015) Preparation of an antibacterial poly(ionic liquid) graft copolymer of hydroxyethyl cellulose. Biomacromol 16:3970–3979. https://doi.org/10.1021/acs.biomac.5b0130010.1021/acs.biomac.5b01300 ↗
29. Klemm D, Heublein B, Fink H-PH, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393. https://doi.org/10.1002/anie.20046058710.1002/anie.200460587 ↗
30. Knaus S, Mais U, Binder WH (2003) Synthesis, characterization and properties of methylaminocellulose. Cellulose 10:139–150. https://doi.org/10.1023/A:102402440273510.1023/A:1024024402735 ↗
31. Kumar MNVR (2000) A review of chitin and chitosan applications. React Funct Polym 46:1–2710.1016/S1381-5148(00)00038-9 ↗
32. Li F, Fei P, Cheng B et al (2019) Synthesis, characterization and excellent antibacterial property of cellulose acetate reverse osmosis membrane via a two-step reaction. Carbohydr Polym 216:312–321. https://doi.org/10.1016/j.carbpol.2019.04.02610.1016/j.carbpol.2019.04.026 ↗
33. Liebert T, Hänsch C, Heinze T (2006) Click chemistry with polysaccharides. Macromol Rapid Commun 27:208–213. https://doi.org/10.1002/marc.20050068610.1002/marc.200500686 ↗
34. 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. https://doi.org/10.1016/S0008-6215(02)00132-510.1016/S0008-6215(02)00132-5 ↗
35. Liu C, Baumann H (2005) New 6-butylamino-6-deoxycellulose and 6-deoxy-6-pyridiniumcellulose derivatives with highest regioselectivity and completeness of reaction. Carbohydr Res 340:2229–2235. https://doi.org/10.1016/J.CARRES.2005.07.01810.1016/J.CARRES.2005.07.018 ↗
36. Liu S, Edgar KJ (2017) Water-soluble co-polyelectrolytes by selective modification of cellulose esters. Carbohydr Polym 162:1–9. https://doi.org/10.1016/J.CARBPOL.2017.01.00810.1016/J.CARBPOL.2017.01.008 ↗
37. Liu S, Liu J, Esker AR, Edgar KJ (2016) An efficient, regioselective pathway to cationic and zwitterionic N -heterocyclic cellulose ionomers. Biomacromol 17:503–513. https://doi.org/10.1021/acs.biomac.5b0141610.1021/acs.biomac.5b01416 ↗
38. Liu S, Gao C, Mosquera-Giraldo LI et al (2018) Selective synthesis of curdlan ω-carboxyamides by staudinger ylide nucleophilic ring-opening. Carbohydr Polym 190:222–231. https://doi.org/10.1016/J.CARBPOL.2018.02.07410.1016/J.CARBPOL.2018.02.074 ↗
39. Matsui Y, Ishikawa J, Kamitakahara H et al (2005) Facile synthesis of 6-amino-6-deoxycellulose. Carbohydr Res 340:1403–1406. https://doi.org/10.1016/J.CARRES.2005.02.03010.1016/J.CARRES.2005.02.030 ↗
40. McCormick CL, Dawsey TR, Newman JK (1990) Competitive formation of cellulose p-toluenesulfonate and chlorodeoxycellulose during homogeneous reaction of p-toluenesulfonyl chloride with cellulose in N,N-dimethylacetamide-lithium chloride. Carbohydr Res 208:183–191. https://doi.org/10.1016/0008-6215(90)80098-N10.1016/0008-6215(90)80098-N ↗
41. McNamara JT, Morgan JLW, Zimmer J (2015) A molecular description of cellulose biosynthesis. Ann Rev Biochem 84:895–921. https://doi.org/10.1146/annurev-biochem-060614-03393010.1146/annurev-biochem-060614-033930 ↗
42. Meng X, Edgar KJ (2016) Click reactions in polysaccharide modification. Prog Polym Sci 53:52–85. https://doi.org/10.1016/J.PROGPOLYMSCI.2015.07.00610.1016/J.PROGPOLYMSCI.2015.07.006 ↗
43. Mischnick P, Momcilovic D (2010) Chemical structure analysis of starch and cellulose derivatives. Advances in carbohydrate chemistry and biochemistry. Academic Press, Cambridge, pp 117–210
44. Mischnick P, Niedner W, Adden R (2005) Possibilities of mass spectrometry and tandem-mass spectrometry in the analysis of cellulose ethers. Macromol Symp 223:67–78. https://doi.org/10.1002/masy.20055050510.1002/masy.200550505 ↗
45. Mosquera-Giraldo LI, Borca CH, Meng X et al (2016) Mechanistic design of chemically diverse polymers with applications in oral drug delivery. Biomacromolecules 17:3659–3671. https://doi.org/10.1021/acs.biomac.6b0115610.1021/acs.biomac.6b01156 ↗
46. Nichols BLB, Chen J, Mischnick P, Edgar KJ (2020) Selective oxidation of 2-hydroxypropyl ethers of cellulose and dextran: simple and efficient introduction of versatile ketone groups to polysaccharides. Biomacromolecules. https://doi.org/10.1021/acs.biomac.0c01045. (Biomacromolecules 21)10.1021/acs.biomac.0c01045 ↗
47. Nikolaeva D, Verachtert K, Azcune I et al (2021) Influence of ionic liquid-like cationic pendants composition in cellulose based polyelectrolytes on membrane-based CO2 separation. Carbohydr Polym 255:117375. https://doi.org/10.1016/J.CARBPOL.2020.11737510.1016/J.CARBPOL.2020.117375 ↗
48. Petzold-Welcke K, Michaelis N, Heinze T et al (2009) Unconventional cellulose products through nucleophilic displacement reactions. Macromol Symp 280:72–85. https://doi.org/10.1002/masy.20095060910.1002/masy.200950609 ↗
49. Pollak PI, Curtin DY (1950) Stereospecificity in the rearrangement of Amino Alcohols. J Am Chem Soc 72:961–965. https://doi.org/10.1021/JA01158A082/ASSET/JA01158A082.FP.PNG_V0310.1021/JA01158A082/ASSET/JA01158A082.FP.PNG_V03 ↗
50. Reinhart K, Hartog CS (2012) Hydroxyethyl starch in patients with trauma. Br J Anaesth 108:321–322. https://doi.org/10.1093/bja/aer46710.1093/bja/aer467 ↗
51. Ren J, Wang P, Dong F et al (2012) Synthesis and antifungal properties of 6-amino-6-deoxyinulin, a kind of precursors for facile chemical modifications of inulin. Carbohydr Polym 87:1744–1748. https://doi.org/10.1016/J.CARBPOL.2011.09.08210.1016/J.CARBPOL.2011.09.082 ↗
52. Sato T, Koizumi J, Ohno Y, Endo T (1990) An improved procedure for the preparation of chlorinated cellulose with methanesulfonyl chloride in a dimethylformamide–chloral–pyridine mixture. J Polym Sci A Polym Chem 28:2223–2227. https://doi.org/10.1002/pola.1990.08028081710.1002/pola.1990.080280817 ↗
53. Schmidt S, Liebert T, Heinze T (2014) Synthesis of soluble cellulose tosylates in an eco-friendly medium. Green Chem 16:1941–1946. https://doi.org/10.1039/C3GC41994K10.1039/C3GC41994K ↗
54. Svensson A, Sjöström J, Scheel T, Piculell L (2003) Phases and structures of a polyion-surfactant ion complex salt in aqueous mixtures: cationic hydroxyethyl cellulose with dodecylsulfate counterions. Coll Surf A Physicochem Eng Asp 228:91–106. https://doi.org/10.1016/S0927-7757(03)00377-710.1016/S0927-7757(03)00377-7 ↗
55. Wang X, Wu M, Zhang B et al (2019) Phase-transfer method synthesis hydroxyethyl cellulose lauryl ether. Coll Surf A Physicochem Eng Asp 562:383–391. https://doi.org/10.1016/j.colsurfa.2018.11.05510.1016/j.colsurfa.2018.11.055 ↗
56. Wang K, Ye L (2010) Structure and property of cationic hydroxyethyl cellulose. Polym Plast Technol Eng 49:807–811. https://doi.org/10.1080/0360255100374961910.1080/03602551003749619 ↗
57. Winstein S, Holness NJ (1955) Neighboring carbon and hydrogen. XIX. t-butylcyclohexyl derivatives. quantitative conformational analysis. J Am Chem Soc 77:5562–5578. https://doi.org/10.1021/JA01626A037/ASSET/JA01626A037.FP.PNG_V0310.1021/JA01626A037/ASSET/JA01626A037.FP.PNG_V03 ↗
58. Zhang R, Edgar KJ (2014) Synthesis of curdlan derivatives regioselectively modified at C-6: O–(N)-Acylated 6-amino-6-deoxycurdlan. Carbohydr Polym 105:161–168. https://doi.org/10.1016/J.CARBPOL.2014.01.04510.1016/J.CARBPOL.2014.01.045 ↗
59. Zhang R, Edgar KJ (2015) Water-soluble aminocurdlan derivatives by chemoselective azide reduction using NaBH 4. Carbohydr Polym 122:84–92. https://doi.org/10.1016/J.CARBPOL.2014.12.02010.1016/J.CARBPOL.2014.12.020 ↗
60. Zhang R, Liu S, Edgar KJ (2017) Efficient synthesis of secondary amines by reductive amination of curdlan Staudinger ylides. Carbohydr Polym 171:1–8. https://doi.org/10.1016/J.CARBPOL.2017.04.09310.1016/J.CARBPOL.2017.04.093 ↗
61. Zhou S, Xu C, Wang J et al (2004) Phase Behavior of cationic hydroxyethyl cellulose – sodium dodecyl sulfate mixtures: effects of molecular weight and ethylene oxide side chain length of polymers. Langmuir 20:8482–8489. https://doi.org/10.1021/la049142n10.1021/la049142n ↗