Vanillin, a key-intermediate of biobased polymers

European Polymer Journal

Volumn 68, Issue , 2015, Pages 488-502

  Fache, Maxence ^a   Boutevin, Bernard ^a   Caillol, Sylvain ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Biobased; Lignin; Phenolic; Polymers; Vanillin

Indexed keywords

LIGNIN; POLYESTER RESINS;

BENZOXAZINE RESIN; BIO-BASED; BIO-BASED POLYMERS; METHACRYLATE POLYMERS; PHENOLIC; RENEWABLE RESOURCE; SCIENTIFIC COMMUNITY; VANILLIN;

POLYMERS;

EID: 84938966365     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2015.03.050     Document Type: Review

References (66)

1. M.M. Bomgardner Following many routes to naturally derived vanillin Chem Eng News 92 6 2014
2. M.B. Hocking Vanillin: synthetic flavoring from spent sulfite liquor J Chem Educ 74 9 1997 1055
3. N.J. Walton, M.J. Mayer, and A. Narbad Molecules of interest: vanillin Phytochemistry 63 2003 505 515
4. H. Priefert, J. Rabenhorst, and A. Steinbüchel Biotechnological production of vanillin Appl Microbiol Biotechnol 56 3-4 2001 296 314
5. D. Havkin-Frenkel, and F. Belanger Biotechnological production of vanillin Biotechnol Flavor Prod 2008 83 98
6. R. Rana, A. Mathur, C. Jain, S. Sharma, and G. Mathur Microbial production of vanillin Braz J Microbiol 41 2010 519 530
7. L. Lesage-Meessen, C. Stentelaire, A. Lomascolo, D. Couteau, M. Asther, S. Moukha, and et al. Fungal transformation of ferulic acid from sugar beet pulp to natural vanillin J Sci Food Agric 79 3 1999 487 490
8. L. Zheng, P. Zheng, Z. Sun, Y. Bai, J. Wang, and X. Guo Production of vanillin from waste residue of rice bran oil by Aspergillus niger and Pycnoporus cinnabarinus Bioresour Technol 98 5 2007 1115 1119
9. E.H. Hansen, B.L. Moller, G.R. Kock, C.M. Bunner, C. Kristensen, O.R. Jensen, and et al. De novo biosynthesis of vanillin in fission yeast (Schizosaccharomyces pombe) and baker's yeast (Saccharomyces cerevisiae) Appl Environ Microbiol 75 9 2009 2765 2774
10. P. Barghini, D. Di Gioia, F. Fava, and M. Ruzzi Vanillin production using metabolically engineered Escherichia coli under non-growing conditions Microb Cell Fact 6 1 2007 1 11
11. K. Li, and J. Frost Synthesis of vanillin from glucose J Am Chem Soc 120 40 1998 10545 10546
12. Hansen J, Hansen EH, Sompalli HP, Sheridan JM, Heal JR, Hamilton WDO. Compositions and methods for the biosynthesis of vanillin or vanillin beta-d-glucoside. WO2013022881A8; 2013.
13. C. Brazinha, D.S. Barbosa, and J.G. Crespo Sustainable recovery of pure natural vanillin from fermentation media in a single pervaporation step Green Chem 13 8 2011 2197 2203
14. E.A. Borges da Silva, M. Zabkova, J.D. Araújo, C.A. Cateto, M.F. Barreiro, M.N. Belgacem, and et al. An integrated process to produce vanillin and lignin-based polyurethanes from kraft lignin Chem Eng Res Des 87 9 2009 1276 1292
15. Sandborn LT, Richter SJ, Clemens HG. Process of making vanillin. US2057117; 1936.
16. V.E. Tarabanko, and D.V. Petukhov Study on mechanism and improvement of the process of oxidative cleavage of lignins into the aromatic aldehydes Chem Sust Dev 11 2003 655
17. S. Chu, A.V. Subrahmanyam, and G.W. Huber The pyrolysis chemistry of a β-O-4 type oligomeric lignin model compound Green Chem 15 1 2013 125 136
18. S.G. Santos, A.P. Marques, D.L.D. Lima, D.V. Evtuguin, and V.I. Esteves Kinetics of eucalypt lignosulfonate oxidation to aromatic aldehydes by oxygen in alkaline medium Ind Eng Chem Res 50 1 2010 291 298
19. C. Fargues, Á. Mathias, and A. Rodrigues Kinetics of vanillin production from kraft lignin oxidation Ind Eng Chem Res 35 1 1996 28 36
20. J.D.P. Araújo, C.A. Grande, and A.E. Rodrigues Vanillin production from lignin oxidation in a batch reactor Chem Eng Res Des 88 8 2010 1024 1032
21. H.-R. Bjørsvik, and F. Minisci Fine chemicals from lignosulfonates. 1. Synthesis of vanillin by oxidation of lignosulfonates Org Process Res Dev 3 5 1999 330 340
22. T. Voitl, and PRv. Rohr Demonstration of a process for the conversion of kraft lignin into vanillin and methyl vanillate by acidic oxidation in aqueous methanol Ind Eng Chem Res 49 2 2009 520 525
23. M. Zabkova, E.A. Borges da Silva, and A.E. Rodrigues Recovery of vanillin from kraft lignin oxidation by ion-exchange with neutralization Sep Purif Technol 55 1 2007 56 68
24. M. Žabková, E.A.B. da Silva, and A.E. Rodrigues Recovery of vanillin from lignin/vanillin mixture by using tubular ceramic ultrafiltration membranes J Membr Sci 301 1-2 2007 221 237
25. Derouane EG, Powell RA. Vanillin extraction process using large pore, high silica/alumina ratio zeolites. US4652684; 1987.
26. J. Zakzeski, P.C. Bruijnincx, A.L. Jongerius, and B.M. Weckhuysen The catalytic valorization of lignin for the production of renewable chemicals Chem Rev 110 6 2010 3552 3599
27. H. Lange, S. Decina, and C. Crestini Oxidative upgrade of lignin - recent routes reviewed Eur Polymer J 49 6 2013 1151 1173
28. P.C. Rodrigues Pinto, E.A. Borges da Silva, and A.E. Rodrigues Biomass conversion - chapter 12 - lignin as source of fine chemicals: vanillin and syringaldehyde 2012 Springer 381 420
29. I.A. Pearl Reactions of vanillin and its derived compounds. I. The reaction of vanillin with silver oxide1 J Am Chem Soc 68 3 1946 429 432
30. Holladay J, Bozell J, White J, Johnson D. Top value-added chemicals from biomass - volume II - results of screening for potential candidates from biorefinery lignin. US Department of Energy: Springfield, VA; 2007. p. 1-77.
31. H. Chung, and N.R. Washburn Chemistry of lignin-based materials Green Mater 1 3 2012 137 160
32. S. Laurichesse, and L. Avérous Chemical modification of lignins: towards biobased polymers Prog Polym Sci 2013
33. D. Stewart Lignin as a base material for materials applications: chemistry, application and economics Ind Crops Prod 27 2 2008 202 207
34. T. Koike Progress in development of epoxy resin systems based on wood biomass in Japan Polym Eng Sci 52 4 2012 701 717
35. C. Aouf, J. Lecomte, P. Villeneuve, E. Dubreucq, and H. Fulcrand Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers Green Chem 14 8 2012 2328
36. M. Fache, E. Darroman, V. Besse, R. Auvergne, S. Caillol, and B. Boutevin Vanillin, a promising biobased building-block for monomer synthesis Green Chem 16 4 2014 1987
37. M. Fache, S. Caillol, R. Auvergne, and B. Boutevin New vanillin-derived diepoxy monomers for the synthesis of biobased thermosets Eur Polym J. 67 2015 527 538
38. L. Gu, G. Chen, and Y. Yao Two novel phosphorus-nitrogen-containing halogen-free flame retardants of high performance for epoxy resin Polym Degrad Stab 108 2014 68 75
39. T. Shimasaki, S. Yoshihara, and M. Shibata Preparation and properties of biocomposites composed of sorbitol-based epoxy resin, pyrogallol-vanillin calixarene, and wood flour Polym Compos 33 10 2012 1840 1847
40. N.P.S. Chauhan Facile synthesis of environmental friendly halogen-free microporous terpolymer from renewable source with enhanced physical properties Des Monomers Polym 15 6 2012 587 600
41. N.P.S. Chauhan Preparation and characterization of bio-based terpolymer derived from vanillin oxime, formaldehyde, and p-hydroxyacetophenone Des Monomers Polym 17 2 2013 176 185
42. J.F. Stanzione III, J.M. Sadler, J.J. La Scala, K.H. Reno, and R.P. Wool Vanillin-based resin for use in composite applications Green Chem 14 8 2012 2346
43. A.L. Holmberg, J.F. Stanzione, R.P. Wool, and T.H. Epps A facile method for generating designer block copolymers from functionalized lignin model compounds ACS Sust Chem Eng 2 4 2014 569 573
44. E. Renbutsu, S. Okabe, Y. Omura, F. Nakatsubo, S. Minami, H. Saimoto, and et al. Synthesis of UV-curable chitosan derivatives and palladium (II) adsorption behavior on their UV-exposed films Carbohydr Polym 69 4 2007 697 706
45. F. Pion, A.F. Reano, P.-H. Ducrot, and F. Allais Chemo-enzymatic preparation of new bio-based bis- and trisphenols: new versatile building blocks for polymer chemistry RSC Adv 3 23 2013 8988
46. H. Liu, B. Lepoittevin, C. Roddier, V. Guerineau, L. Bech, J.-M. Herry, and et al. Facile synthesis and promising antibacterial properties of a new guaiacol-based polymer Polymer 52 9 2011 1908 1916
47. L. Mialon, A.G. Pemba, and S.A. Miller Biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid Green Chem 12 10 2010 1704
48. WO2011143379A2. Poly(dihydroferulic acid) a biorenewable polyethylene terephthalate mimic derived from lignin and acetic acid; 2011.
49. L. Mialon, R. Vanderhenst, A.G. Pemba, and S.A. Miller Polyalkylenehydroxybenzoates (PAHBs): biorenewable aromatic/aliphatic polyesters from lignin Macromol Rapid Commun 2011
50. W. Lange, and O. Kordsachia Darstellung und Eigenschaften von aus Vanillin und Syringaaldehyd erhältlichen Polyestern Holz als Roh-und Werkstoff 39 3 1981 107 112
51. C. Pang, J. Zhang, G. Wu, Y. Wang, H. Gao, and J. Ma Renewable polyesters derived from 10-undecenoic acid and vanillic acid with versatile properties Polym Chem 5 8 2014 2843
52. C. Pang, J. Zhang, Q. Zhang, G. Wu, Y. Wang, and J. Ma Novel vanillic acid-based poly(ether-ester)s: from synthesis to properties Polym Chem 6 5 2015 797 804
53. J. Kwon, J. Kim, S. Park, G. Khang, P.M. Kang, and D. Lee Inflammation-responsive antioxidant nanoparticles based on a polymeric prodrug of vanillin Biomacromolecules 14 5 2013 1618 1626
54. A.G. Pemba, M. Rostagno, T.A. Lee, and S.A. Miller Cyclic and spirocyclic polyacetal ethers from lignin-based aromatics Polym Chem 5 9 2014 3214
55. R.S. Jagadish, K.N. Divyashree, P. Viswanath, P. Srinivas, and B. Raj Preparation of N-vanillyl chitosan and 4-hydroxybenzyl chitosan and their physico-mechanical, optical, barrier, and antimicrobial properties Carbohydr Polym 87 1 2012 110 116
56. H. Peng, H. Xiong, J. Li, M. Xie, Y. Liu, C. Bai, and et al. Vanillin cross-linked chitosan microspheres for controlled release of resveratrol Food Chem 121 1 2010 23 28
57. L. Marin, B. Simionescu, and M. Barboiu Imino-chitosan biodynamers Chem Commun (Camb) 48 70 2012 8778 8780
58. L. Marin, I. Stoica, M. Mares, V. Dinu, B.C. Simionescu, and M. Barboiu Antifungal vanillin-imino-chitosan biodynameric films J Mater Chem B 1 27 2013 3353
59. A.R. Cestari, E.F.S. Vieira, and C.R.S. Mattos Thermodynamics of the Cu(II) adsorption on thin vanillin-modified chitosan membranes J Chem Thermodyn 38 9 2006 1092 1099
60. A.S. Amarasekara, and A. Razzaq Vanillin-based polymers - part II: synthesis of schiff base polymers of divanillin and their chelation with metal ions ISRN Polym Sci 2012 2012 1 5
61. A. Van, K. Chiou, and H. Ishida Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring Polymer 55 6 2014 1443 1451
62. N.K. Sini, J. Bijwe, and I.K. Varma Renewable benzoxazine monomer from vanillin: Synthesis, characterization, and studies on curing behavior J Polym Sci, Part A: Polym Chem 52 1 2014 7 11
63. N.K. Sini, J. Bijwe, and I.K. Varma Thermal behaviour of bis-benzoxazines derived from renewable feed stock 'vanillin' Polym Degrad Stab 109 2014 270 277
64. M. Firdaus, and M.A.R. Meier Renewable co-polymers derived from vanillin and fatty acid derivatives Eur Polymer J 49 1 2013 156 166
65. A.S. Amarasekara, B. Wiredu, and A. Razzaq Vanillin based polymers: I. An electrochemical route to polyvanillin Green Chem 14 9 2012 2395
66. B.G. Harvey, A.J. Guenthner, H.A. Meylemans, S.R.L. Haines, K.R. Lamison, T.J. Groshens, and et al. Renewable thermosetting resins and thermoplastics from vanillin Green Chem 17 2 2015 1249 1258