Tetrabutylammonium Hydroxide 30-Hydrate as Novel Reaction Medium for Lignin Conversion

ACS Sustainable Chemistry and Engineering

Volumn 5, Issue 11, 2017, Pages 10111-10115

  Yamamoto, Kohei ^a   Hosoya, Takashi ^a   Yoshioka, Koichi ^a   Miyafuji, Hisashi ^a   Ohno, Hiroyuki ^b   Yamada, Tatsuhiko ^c  

^a KYOTO PREFECTURAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^c FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

Author keywords

Bu4NOH; Degradation; Lignocellulosic biomass; Oxidation; Vanillin

Indexed keywords

DEGRADATION; FORESTRY; LIGNIN; OXIDATION; POSITIVE IONS; SODIUM COMPOUNDS; WOOD PRODUCTS;

BU4NOH; JAPANESE CEDARS (CRYPTOMERIA JAPONICA); LIGNOCELLULOSIC BIOMASS; P-HYDROXYBENZALDEHYDE; SELECTIVE DEGRADATION; SODIUM LIGNOSULFONATES; TETRABUTYLAMMONIUM HYDROXIDES; VANILLIN;

WOOD;

ALKALI LIGNINS; CHAMAECYPARIS OBTUSA; CHEMICAL REACTIONS; LIGNINS; LIGNOCELLULOSE; MILLED WOOD LIGNINS;

EID: 85033449180     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.7b02106     Document Type: Article

References (29)

1. Calvo-Flores, F. G.; Dobado, J. A. Lignin as renewable raw mateial ChemSusChem 2010, 3, 1227-1235 10.1002/cssc.201000157
2. Upton, B. M.; Kasko, A. M. Strategies for the conversion of lignin to high-value polymeric materials: review and perspective Chem. Rev. 2016, 116, 2275-2306 10.1021/acs.chemrev.5b00345
3. Hocking, M. B. Vanillin: synthetic flavoring from spent sulfite liquor J. Chem. Educ. 1997, 74, 1055-1059 10.1021/ed074p1055
4. Llevot, A.; Grau, E.; Carlotti, S.; Grelier, S.; Cramail, H. From lignin-derived aromatic compounds to novel biobased polymers Macromol. Rapid Commun. 2016, 37, 9-28 10.1002/marc.201500474
5. Borges da Silva, A. E.; Zabkova, M.; Araujo, D. J.; Cateto, A. C.; Barreiro, F. M.; Belgacem, N. M.; Rodrigues, E. A. An integrated process to produce vanillin and lignin-based polyurethanes from kraft lignin Chem. Eng. Res. Des. 2009, 87, 1276-1292 10.1016/j.cherd.2009.05.008
6. Araujo, J. D. P.; Grande, C. A.; Rodrigues, A. E. Structured packed bubble column reactor for continuous production of vanillin from kraft lignin oxidation Catal. Today 2009, 147, S330-S335 10.1016/j.cattod.2009.07.016
7. Araujo, J. D. P.; Grande, C. A.; Rodrigues, A. E. Vanillin production from lignin oxidation in a batch reactor Chem. Eng. Res. Des. 2010, 88, 1024-1032 10.1016/j.cherd.2010.01.021
8. Pinto, P. C. R.; Costa, C. E.; Rodrigues, A. E. Oxidation of lignin from eucalyptus globulus pulping liquors to produce syringaldehyde and vanillin Ind. Eng. Chem. Res. 2013, 52, 4421-4428 10.1021/ie303349j
9. Mathias, L. A.; Rodrigues, E. A. Production of vanillin by oxidation of pine kraft lignins with oxygen Holzforschung 1995, 49, 273-278 10.1515/hfsg.1995.49.3.273
10. Fargues, C.; Mathias, A.; Rodrigues, A. Kinetic of vanillin production from kraft lignin oxidation Ind. Eng. Chem. Res. 1996, 35, 28-36 10.1021/ie950267k
11. Jiang, G.; Nowakowski, D. J.; Bridgwater, A. V. Effect of the temperature on the composition of lignin pyrolysis products Energy Fuels 2010, 24, 4470-4475 10.1021/ef100363c
12. Kang, S.; Li, X.; Fan, J.; Chang, J. Hydrothermal conversion of lignin Renewable Sustainable Energy Rev. 2013, 27, 546-558 10.1016/j.rser.2013.07.013
13. Ogawa, S.; Miyafuji, H. Reaction behavior of milled wood lignin in an ionic liquid, 1-ethyl-3-methylimidazolium chloride J. Wood Sci. 2015, 61, 285-291 10.1007/s10086-015-1461-3
14. Forss, K. G.; Talka, E. T.; Fremer, K. E. Isolation of vanillin from alkaline oxidized spent sulfite liquor Ind. Eng. Chem. Prod. Res. Dev. 1986, 25, 103-108 10.1021/i300021a023
15. Tomlinson, G. H.; Hibbert, H. Studies on lignin and related compounds. XXIV. The formation of vanillin from waste sulfite liquor J. Am. Chem. Soc. 1936, 58, 345-348 10.1021/ja01293a046
16. Tomlinson, G. H.; Hibbert, H. Studies on lignin and related compounds. XXV. Mechanism of vanillin formation from spruce lignin sulfonic acids in relation to lignin structure J. Am. Chem. Soc. 1936, 58, 348-353 10.1021/ja01293a047
17. Triumph Venture Capitals Limited. Part3 Aroma chemicals from petrochemical feedstocks. In Study into the Establishment of an Aroma and Fragrance Fine Chemicals Value Chain in South Africa; 2004; pp 31-40.
18. Chang, H. M.; Allan, G. G. In Lignins-Occurrence, Formation, Structure and Reactions; Wiley: 1971; pp 433-485.
19. Schultz, T. P.; Templeton, M. C. Holzforschung 1986, 40, 93-97 10.1515/hfsg.1986.40.2.93
20. Bjorkman, A. Studied on finely divided wood. part1. Extraction of lignin with neutral solvents Svensk Papperstidning 1956, 59, 477-485
21. Gierer, J. Chemistry of delignification Wood Sci. Technol. 1985, 19, 289-312
22. Gierer, J. Aryl migrations during pulping J. Wood Chem. Technol. 1992, 12, 367-386 10.1080/02773819208545787
23. Dimmel, D. R.; Schuller, L. F. Structural/reactivity studies (I): Soda reactions of lignin model compounds J. Wood Chem. Technol. 1986, 6, 535-564 10.1080/02773818608085244
24. Hubbard, T. F.; Schultz, T. P.; Fisher, T. H. Alkaline hydrolysis of nonphenolic β-O-4 lignin model dimers: Substituent effects on the leaving phenoxide in neighboring group vs direct nucleophilic attack Holzforschung 1992, 46, 315-320 10.1515/hfsg.1992.46.4.315
25. Collier, W. E.; Fisher, T. H.; Ingram, L. L., Jr.; Harris, A. L.; Schultz, T. P. Alkaline hydrolysis of nonphenolic β-O-4 lignin model dimers: further studies of the substituent effect on the leaving phenoxide Holzforschung 1996, 50, 420-424 10.1515/hfsg.1996.50.5.420
26. Lundquist, K.; Unge, S. Stability of arylglycerols during alkaline cooking Holzforschung 2004, 58, 330-333 10.1515/HF.2004.051
27. Kubo, S.; Hashida, K.; Hishiyama, S.; Yamada, T.; Hosoya, S. Possibilities of the formation of enol-ethers in lignin by soda pulping J. Wood Chem. Technol. 2015, 35, 62-72 10.1080/02773813.2014.921825
28. Dimmel, D. R.; Bovee, L. F. Pulping reactions of vinyl ethers J. Wood Chem. Technol. 1993, 13, 583-592 10.1080/02773819308020535
29. Kuroda, K. Mokushitsukagakuzikken manual 2000, 97