Multi-scale cellulose based new bio-aerogel composites with thermal super-insulating and tunable mechanical properties

Carbohydrate Polymers

Volumn 138, Issue , 2016, Pages 335-348

  Seantier, Bastien ^a   Bendahou, Dounia ^a,b   Bendahou, Abdelkader ^a   Grohens, Yves ^a   Kaddami, Hamid ^b  

^a UNIVERSITÉ DE BRETAGNE SUD   (France)

^b CADI AYYAD UNIVERSITY   (Morocco)

Author keywords

Cellulose; Cellulose nanocrystals (CNC); Freeze drying; Mechanical properties; Multi scale architecture; Nanofibrillated cellulose (NFC); porosity; Super insulation

Indexed keywords

AEROGELS; ASPECT RATIO; CELLULOSE; CRYSTALLINE MATERIALS; INSULATION; LOW TEMPERATURE DRYING; MECHANICAL PROPERTIES; NANOPARTICLES; NETWORK ARCHITECTURE; POROSITY; THERMAL CONDUCTIVITY;

CELLULOSE NANOCRYSTAL (CNC); CELLULOSE NANOPARTICLES; FREEZE DRYING; INTRINSIC CHARACTERISTICS; NANOFIBRILLATED CELLULOSE (NFC); ORGANIZATION STRUCTURES; PHYSICOCHEMICAL CHARACTERISTICS; SUPER INSULATION;

CELLULOSE FILMS;

CELLULOSE; DRYING; MECHANICAL PROPERTIES; POROSITY;

CELLULOSE; GEL; NANOFIBER; NANOMATERIAL;

ATOMIC FORCE MICROSCOPY; CHEMISTRY; GEL; INFRARED SPECTROSCOPY; POROSITY; THERMAL CONDUCTIVITY; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

CELLULOSE; GELS; MICROSCOPY, ATOMIC FORCE; MICROSCOPY, ELECTRON, TRANSMISSION; NANOFIBERS; NANOSTRUCTURES; POROSITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMAL CONDUCTIVITY; X-RAY DIFFRACTION;

EID: 84954121320     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.11.032     Document Type: Article

References (84)

1. J. Araki, M. Wada, S. Kuga, and T. Okano Flow properties of microcrystalline cellulose suspension prepared by acid treatment of native cellulose Colloids and Surfaces A: Physicochemical and Engineering Aspects 142 1 1998 75 82 http://doi.org/10.1016/S0927-7757(98)00404-X
2. R. Baetens, B.P. Jelle, and A. Gustavsen Aerogel insulation for building applications: A state-of-the-art review Energy and Buildings 43 4 2011 761 769 http://doi.org/10.1016/j.enbuild.2010.12.012
3. S. Beck-Candanedo, M. Roman, and D.G. Gray Effect of reaction conditions on the properties and behavior of wood cellulose nanocrystal suspensions Biomacromolecules 6 2 2005 1048 1054 http://doi.org/10.1021/bm049300p
4. A. Bendahou, Y. Habibi, H. Kaddami, and A. Dufresne Physico-chemical characterization of palm from phoenix dactylifera-L, preparation of cellulose whiskers and natural rubber-based nanocomposites Journal of Biobased Materials and Bioenergy 3 1 2009 81 90 http://doi.org/10.1166/jbmb.2009.1011
5. A. Bendahou, H. Kaddami, and A. Dufresne Investigation on the effect of cellulosic nanoparticles' morphology on the properties of natural rubber based nanocomposites European Polymer Journal 46 4 2010 609 620 http://doi.org/10.1016/j.eurpolymj.2009.12.025
6. D. Bendahou, A. Bendahou, B. Seantier, Y. Grohens, and H. Kaddami Nano-fibrillated cellulose-zeolites based new hybrid composites aerogels with super thermal insulating properties Industrial Crops and Products 65 2015 374 382 http://doi.org/10.1016/j.indcrop.2014.11.012
7. K. Benhamou, A. Dufresne, A. Magnin, G. Mortha, and H. Kaddami Control of size and viscoelastic properties of nanofibrillated cellulose from palm tree by varying the TEMPO-mediated oxidation time Carbohydrate Polymers 99 2014 74 83 http://doi.org/10.1016/j.carbpol.2013.08.032
8. P. Bonnardel, G. Pouleyrn, P. Florent, M. de Candido, P. Achard, A. Rigacci, and et al. Preparation of silica xerogels comprises: Treating organo silica gel with hydrophobing agent in the presence of weak acid and solvent February 2006 France Patent 2873677-A1
9. J. Broekhoff Studies on pore systems in catalysts XIII. Pore distributions from the desorption branch of a nitrogen sorption isotherm in the case of cylindrical pores B Applications, Journal of Catalysis 10 4 1968 377 390 http://doi.org/10.1016/0021-9517(68)90153-X
10. S. Brunauer, P.H. Emmett, and E. Teller Adsorption of gases in multimolecular layers Journal of the American Chemical Society 60 2 1938 309 319 http://doi.org/10.1021/ja01269a023
11. P.S. Chang, and J.F. Robyt Oxidation of primary alcohol groups of naturally occurring polysaccharides with 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion Journal of Carbohydrate Chemistry 15 7 1996 819 830 http://doi.org/10.1080/07328309608005694
12. W. Chen, H. Zhou, M. Tang, M.D. Weir, C. Bao, and H.H.K. Xu Gas-foaming calcium phosphate cement scaffold encapsulating human umbilical cord stem cells Tissue Engineering, A 18 7-8 2012 816 827 http://doi.org/10.1089/ten.tea.2011.0267
13. H.J. Chung, and T.G. Park Surface engineered and drug releasing pre-fabricated scaffolds for tissue engineering Advanced Drug Delivery Reviews 59 4-5 2007 249 262 http://doi.org/10.1016/j.addr.2007.03.015
14. A.R. Costa-Pinto, V.M. Correlo, P.C. Sol, M. Bhattacharya, P. Charbord, B. Delorme, and et al. Osteogenic differentiation of human bone marrow mesenchymal stem cells seeded on melt based chitosan scaffolds for bone tissue engineering applications Biomacromolecules 10 8 2009 2067 2073 http://doi.org/10.1021/bm9000102
15. D. Da Silva Perez, S. Montanari, and M.R. Vignon TEMPO-mediated oxidation of cellulose III Biomacromolecules 4 5 2003 1417 1425 http://doi.org/10.1021/bm034144s
16. Z. Dang, J. Zhang, and A.J. Ragauskas Characterizing TEMPO-mediated oxidation of ECF bleached softwood kraft pulps Carbohydrate Polymers 70 3 2007 310 317 http://doi.org/10.1016/j.carbpol.2007.04.014
17. A.E.J. De Nooy, A.C. Besemer, and H. van Bekkum Selective oxidation of primary alcohols mediated by nitroxyl radical in aqueous solution. Kinetics and mechanism Tetrahedron 51 29 1995 8023 8032 http://doi.org/10.1016/0040-4020(95)00417-7
18. X.M. Dong, J.-F. Revol, and D.G. Gray Effect of microcrystallite preparation conditions on the formation of colloid crystals of cellulose Cellulose 5 1 1998 19 32 http://doi.org/10.1023/A:1009260511939
19. W.N. Dos Santos Thermal properties of melt polymers by the hot wire technique Polymer Testing 24 7 2005 932 941 http://doi.org/10.1016/j.polymertesting.2005.06.001
20. F. Fischer, A. Rigacci, R. Pirard, S. Berthon-Fabry, and P. Achard Cellulose-based aerogels Polymer 47 22 2006 7636 7645 http://doi.org/10.1016/j.polymer.2006.09.004
21. J. Fricke, E. HüMmer, H.-J. Morper, and P. Scheuerpflug Thermal properties of silica aerogels Le Journal de Physique Colloques 24 1989 C4-87-C4-97, http://doi.org/10.1051/jphyscol:1989414
22. H. Fukuzumi, T. Saito, S. Iwamoto, Y. Kumamoto, T. Ohdaira, R. Suzuki, and et al. Pore size determination of tempo-oxidized cellulose nanofibril films by positron annihilation lifetime spectroscopy Biomacromolecules 12 11 2011 4057 4062 http://doi.org/10.1021/bm201079n
23. N.L. Garcia de Rodriguez, W. Thielemans, and A. Dufresne Sisal cellulose whiskers reinforced polyvinyl acetate nanocomposites Cellulose 13 3 2006 261 270 http://doi.org/10.1007/s10570-005-9039-7
24. C.A. García-González, M. Alnaief, and I. Smirnova Polysaccharide-based aerogels - Promising biodegradable carriers for drug delivery systems Carbohydrate Polymers 86 4 2011 1425 1438 http://doi.org/10.1016/j.carbpol.2011.06.066
25. L.J. Gibson, and M.F. Ashby 2nd ed. Cellular solids: Structure and properties vol. 1 1997 Cambridge University Press Cambridge (UK)
26. S. Gomez-Bujedo, E. Fleury, and M.R. Vignon Preparation of cellouronic acids and partially acetylated cellouronic acids by TEMPO/NaClO oxidation of water-soluble cellulose acetate Biomacromolecules 5 2 2004 565 571 http://doi.org/10.1021/bm034405y
27. X. Gong, Y. Wang, Z. Tian, X. Zheng, and L. Chen Controlled production of spruce cellulose gels using an environmentally "green" system Cellulose 21 3 2014 1667 1678 http://doi.org/10.1007/s10570-014-0200-z
28. E. Guilminot, R. Gavillon, M. Chatenet, S. Berthon-Fabry, A. Rigacci, and T. Budtova New nanostructured carbons based on porous cellulose: Elaboration, pyrolysis and use as platinum nanoparticles substrate for oxygen reduction electrocatalysis Journal of Power Sources 185 2 2008 717 726 http://doi.org/10.1016/j.jpowsour.2008.08.030
29. Y. Habibi, H. Chanzy, and M.R. Vignon TEMPO-mediated surface oxidation of cellulose whiskers Cellulose 13 6 2006 679 687 http://doi.org/10.1007/s10570-006-9075-y
30. C.A. Hall, K.A. Le, C. Rudaz, A. Radhi, C.S. Lovell, R.A. Damion, and et al. Macroscopic and microscopic study of 1-ethyl-3-methyl-imidazolium acetate-water mixtures The Journal of Physical Chemistry B 116 42 2012 12810 12818 http://doi.org/10.1021/jp306829c
31. Y. Han, X. Zhang, X. Wu, and C. Lu Flame retardant, heat insulating cellulose aerogels from waste cotton fabrics by in situ formation of magnesium hydroxide nanoparticles in cellulose gel nanostructures ACS Sustainable Chemistry & Engineering 3 8 2015 1853 1859 http://doi.org/10.1021/acssuschemeng.5b00438
32. R. Haul S. J. Gregg, K. S. W. Sing: Adsorption, Surface Area and Porosity. 2. Auflage Academic Press, London 1982. 303 Seiten, Preis: $ 49.50 Berichte Der Bunsengesellschaft Für Physikalische Chemie 86 1982 957 http://doi.org/10.1002/bbpc.19820861019
33. F.W. Herrick, R.L. Casebier, J.K. Hamilton, and K.R. Sandberg Microfibrillated cellulose: Morphology and accessibility Journal of Applied Polymer Science: Applied Polymer Symposium 37 1983 797 813
34. Q. Hou, D.W. Grijpma, and J. Feijen Porous polymeric structures for tissue engineering prepared by a coagulation, compression moulding and salt leaching technique Biomaterials 24 11 2003 1937 1947 http://doi.org/10.1016/S0142-9612(02)00562-8
35. A. Isogai, and Y. Kato Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation Cellulose 5 3 1998 153 164 http://doi.org/10.1023/A:1009208603673
36. Hao Jin, Y. Nishiyama, M. Wada, and S. Kuga Nanofibrillar cellulose aerogels Colloids and Surfaces A: Physicochemical and Engineering Aspects 240 1-3 2004 63 67 http://doi.org/10.1016/j.colsurfa.2004.03.007
37. Jin Hua, A. Cao, E. Shi, J. Seitsonen, L. Zhang, R.H.A. Ras, and et al. Ionically interacting nanoclay and nanofibrillated cellulose lead to tough bulk nanocomposites in compression by forced self-assembly Journal of Materials Chemistry B 1 6 2013 835 840 http://doi.org/10.1039/C2TB00370H
38. H. Kaddami, A. Dufresne, B. Khelifi, A. Bendahou, M. Taourirte, M. Raihane, and et al. Short palm tree fibers - Thermoset matrices composites Composites, A: Applied Science and Manufacturing 37 9 2006 1413 1422 http://doi.org/10.1016/j.compositesa.2005.06.020
39. A. Kadimi, K. Benhamou, Z. Ounaies, A. Magnin, A. Dufresne, H. Kaddami, and et al. Electric field alignment of nanofibrillated cellulose (NFC) in silicone oil: Impact on electrical properties ACS Applied Materials & Interfaces 6 12 2014 9418 9425 http://doi.org/10.1021/am501808h
40. S.S. Kistler Coherent expanded aerogels and jellies Nature 127 3211 1931 741-741, http://doi.org/10.1038/127741a0
41. S.S. Kistler Coherent expanded-aerogels The Journal of Physical Chemistry 36 1 1931 52 64 http://doi.org/10.1021/ja01269a023
42. Y. Kobayashi, T. Saito, and A. Isogai Aerogels with 3D ordered nanofiber skeletons of liquid-crystalline nanocellulose derivatives as tough and transparent insulators Angewandte Chemie 126 39 2014 10562 10565 http://doi.org/10.1002/ange.201405123
43. J.P.F. Lagerwall, C. Schütz, M. Salajkova, J. Noh, J. Hyun Park, G. Scalia, and et al. Cellulose nanocrystal-based materials: From liquid crystal self-assembly and glass formation to multifunctional thin films NPG Asia Materials 6 1 2014 e80 http://doi.org/10.1038/am.2013.69
44. N. Lavoine, I. Desloges, A. Dufresne, and J. Bras Microfibrillated cellulose - Its barrier properties and applications in cellulosic materials: A review Carbohydrate Polymers 90 2 2012 735 764 http://doi.org/10.1016/j.carbpol.2012.05.026
45. M.-C. Li, Q. Wu, K. Song, S. Lee, Y. Qing, and Y. Wu Cellulose nanoparticles: Structure-morphology-rheology relationships ACS Sustainable Chemistry & Engineering 3 5 2015 821 832 http://doi.org/10.1021/acssuschemeng.5b00144
46. M.-C. Li, Q. Wu, K. Song, Y. Qing, and Y. Wu Cellulose nanoparticles as modifiers for rheology and fluid loss in bentonite water-based fluids ACS Applied Materials & Interfaces 7 8 2015 5006 5016 http://doi.org/10.1021/acsami.5b00498
47. F. Liebner, E. Haimer, A. Potthast, D. Loidl, S. Tschegg, M.-A. Neouze, and et al. Cellulosic aerogels as ultra-lightweight materials Part 2: Synthesis and properties 2nd ICC 2007 Tokyo, Japan, October 25-29, 2007. Holzforschung, vol. 63 (1) 2009 http://doi.org/10.1515/HF.2009.002
48. J. Liu Physical characterization of pharmaceutical formulations in frozen and freeze-dried solid states: Techniques and applications in freeze-drying development Pharmaceutical Development and Technology 11 1 2006 3 28 http://doi.org/10.1080/10837450500463729
49. X. Lu, R. Caps, J. Fricke, C.T. Alviso, and R.W. Pekala Correlation between structure and thermal conductivity of organic aerogels Journal of Non-Crystalline Solids 188 3 1995 226 234 http://doi.org/10.1016/0022-3093(95)00191-3
50. Y. Maréchal, and H. Chanzy The hydrogen bond network in Iβ cellulose as observed by infrared spectrometry Journal of Molecular Structure 523 1-3 2000 183 196 http://doi.org/10.1016/S0022-2860(99)00389-0
51. T. Mehling, I. Smirnova, U. Guenther, and R.H.H. Neubert Polysaccharide-based aerogels as drug carriers Journal of Non-Crystalline Solids 355 50-51 2009 2472 2479 http://doi.org/10.1016/j.jnoncrysol.2009.08.038
52. S. Montanari, M. Roumani, L. Heux, and M.R. Vignon Topochemistry of carboxylated cellulose nanocrystals resulting from TEMPO-mediated oxidation Macromolecules 38 5 2005 1665 1671 http://doi.org/10.1021/ma048396c
53. J. Nemoto, T. Soyama, T. Saito, and A. Isogai Nanoporous networks prepared by simple air drying of aqueous TEMPO-oxidized cellulose nanofibril dispersions Biomacromolecules 13 3 2012 943 946 http://doi.org/10.1021/bm300041k
54. S.T. Nguyen, J. Feng, S.K. Ng, J.P.W. Wong, V.B.C. Tan, and H.M. Duong Advanced thermal insulation and absorption properties of recycled cellulose aerogels Colloids and Surfaces A: Physicochemical and Engineering Aspects 445 2014 128 134 http://doi.org/10.1016/j.colsurfa.2014.01.015
55. B. Notario, J. Pinto, E. Solorzano, J.A. de Saja, M. Dumon, and M.A. Rodríguez-Pérez Experimental validation of the Knudsen effect in nanocellular polymeric foams Polymer 56 2015 57 67 http://doi.org/10.1016/j.polymer.2014.10.006
56. Y. Okita, T. Saito, and A. Isogai Entire surface oxidation of various cellulose microfibrils by TEMPO-mediated oxidation Biomacromolecules 11 6 2010 1696 1700 http://doi.org/10.1021/bm100214b
57. R.W. Pekala Organic aerogels from the polycondensation of resorcinol with formaldehyde Journal of Materials Science 24 9 1989 3221 3227 http://doi.org/10.1007/BF01139044
58. R.W. Pekala, S.T. Mayer, J.L. Kaschmitter, and F.M. Kong Carbon aerogels: An update on structure, properties, and applications Y.A. Attia, Sol-Gel processing and applications 1994 Springer US Boston, MA 369 377 Retrieved from http://link.springer.com/10.1007/978-1-4615-2570-7-32
59. W. Pekala Richard Low density, resorcinol-formaldehyde aerogels March 1991 US patente US 4873218 A
60. F. Peng, M.T. Shaw, J.R. Olson, and M. Wei Hydroxyapatite needle-shaped particles/poly(l-lactic acid) electrospun scaffolds with perfect particle-along-nanofiber orientation and significantly enhanced mechanical properties The Journal of Physical Chemistry C 115 32 2011 15743 15751 http://doi.org/10.1021/jp201384q
61. V. Pimenov, V.S. Drozhzhin, and A. Sakharov Ultra-low-density microcellular aerogels based on cellulose acetate Polymer Science Series B 45 1-2 2003 4 6
62. Pyrogel XT-E. (2015). (http://www.aerogel.com/products-and-solutions/pyrogel-xt-e/) consulted in April 2015.
63. L. Qian, and H. Zhang Controlled freezing and freeze drying: A versatile route for porous and micro-/nano-structured materials Journal of Chemical Technology & Biotechnology 86 2 2011 172 184 http://doi.org/10.1002/jctb.2495
64. C. Rudaz, and T. Budtova Rheological and hydrodynamic properties of cellulose acetate/ionic liquid solutions Carbohydrate Polymers 92 2 2013 1966 1971 http://doi.org/10.1016/j.carbpol.2012.11.066
65. T. Saito, M. Hirota, N. Tamura, S. Kimura, H. Fukuzumi, L. Heux, and et al. Individualization of nano-sized plant cellulose fibrils by direct surface carboxylation using TEMPO catalyst under neutral conditions Biomacromolecules 10 7 2009 1992 1996 http://doi.org/10.1021/bm900414t
66. T. Saito, and A. Isogai TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions Biomacromolecules 5 5 2004 1983 1989 http://doi.org/10.1021/bm0497769
67. A. Sbiai, H. Kaddami, H. Sautereau, A. Maazouz, and E. Fleury TEMPO-mediated oxidation of lignocellulosic fibers from date palm leaves Carbohydrate Polymers 86 4 2011 1445 1450 http://doi.org/10.1016/j.carbpol.2011.06.005
68. Y. Scudeller, and J.P. Bardon Simultaneous measurement of the thermal conductivity and diffusivity of small size elements: Application to the characterization of integrated circuit package samples International Journal of Heat and Mass Transfer 34 3 1991 673 680 http://doi.org/10.1016/0017-9310(91)90115-U
69. L. Segal, J.J. Creely, A.E. Martin, and C.M. Conrad An empirical method for estimating the degree of crystallinity of native cellulose using the X-ray diffractometer Textile Research Journal 29 10 1959 786 794 http://doi.org/10.1177/004051755902901003
70. H. Sehaqui, Q. Zhou, and L.A. Berglund High-porosity aerogels of high specific surface area prepared from nanofibrillated cellulose (NFC) Composites Science and Technology 71 13 2011 1593 1599 http://doi.org/10.1016/j.compscitech.2011.07.003
71. S. Sequeira, D.V. Evtuguin, and I. Portugal Preparation and properties of cellulose/silica hybrid composites Polymer Composites 30 9 2009 1275 1282 http://doi.org/10.1002/pc.20691
72. R. Sescousse, R. Gavillon, and T. Budtova Aerocellulose from cellulose-ionic liquid solutions: Preparation, properties and comparison with cellulose-NaOH and cellulose-NMMO routes Carbohydrate Polymers 83 4 2011 1766 1774 http://doi.org/10.1016/j.carbpol.2010.10.043
73. I. Shibata, and A. Isogai Depolymerization of cellouronic acid during TEMPO-mediated oxidation Cellulose 10 2 2003 151 158 http://doi.org/10.1023/A:1024051514026
74. R. Shinoda, T. Saito, Y. Okita, and A. Isogai Relationship between length and degree of polymerization of TEMPO-oxidized cellulose nanofibrils Biomacromolecules 13 3 2012 842 849 http://doi.org/10.1021/bm2017542
75. T.C.F. Silva, Y. Habibi, J.L. Colodette, T. Elder, and L.A. Lucia A fundamental investigation of the microarchitecture and mechanical properties of tempo-oxidized nanofibrillated cellulose (NFC)-based aerogels Cellulose 19 6 2012 1945 1956 http://doi.org/10.1007/s10570-012-9761-x
76. G. Siqueira, J. Bras, and A. Dufresne Cellulose whiskers versus microfibrils: Influence of the nature of the nanoparticle and its surface functionalization on the thermal and mechanical properties of nanocomposites Biomacromolecules 10 2 2009 425 432 http://doi.org/10.1021/bm801193d
77. P.T. Sudheesh Kumar, S. Srinivasan, V.-K. Lakshmanan, H. Tamura, S.V. Nair, and R. Jayakumar β-Chitin hydrogel/nano hydroxyapatite composite scaffolds for tissue engineering applications Carbohydrate Polymers 85 3 2011 584 591 http://doi.org/10.1016/j.carbpol.2011.03.018
78. C. Tahiri, and M.R. Vignon TEMPO-oxidation of cellulose: Synthesis and characterisation of polyglucuronans Cellulose 7 2 2000 177 188 http://doi.org/10.1023/A:1009276009711
79. C. Tan, B.M. Fung, J.K. Newman, and C. Vu Organic aerogels with very high impact strength Advanced Materials 13 9 2001 644 646 http://doi.org/10.1002/1521-4095(200105)13:9<644::AID-ADMA644>3.0.CO;2-
80. P. Tsou Silica aerogel captures cosmic dust intact Journal of Non-Crystalline Solids 186 1995 415 427 http://doi.org/10.1016/0022-3093(95)00065-8
81. A. Venkateswara Rao, N.D. Hegde, and H. Hirashima Absorption and desorption of organic liquids in elastic superhydrophobic silica aerogels Journal of Colloid and Interface Science 305 1 2007 124 132 http://doi.org/10.1016/j.jcis.2006.09.025
82. X. Xu, F. Liu, L. Jiang, J.Y. Zhu, D. Haagenson, and D.P. Wiesenborn Cellulose nanocrystals vs cellulose nanofibrils: A comparative study on their microstructures and effects as polymer reinforcing agents ACS Applied Materials & Interfaces 5 8 2013 2999 3009 http://doi.org/10.1021/am302624t
83. H. Yun, S. Kim, Y. Hyun, S. Heo, and J. Shin Three-dimensional mesoporous-giantporous inorganic/organic composite scaffolds for tissue engineering Chemistry of Materials 19 26 2007 6363 6366 http://doi.org/10.1021/cm7023923
84. M. Zhao, J. Li, E. Mano, Z. Song, D.M. Tschaen, E.J.J. Grabowski, and et al. Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach The Journal of Organic Chemistry 64 7 1999 2564 2566 http://doi.org/10.1021/jo982143y