참고문헌
- M. H. Jung, Bioplastics, 1-152, Research and Policy Center for Chemical Technology, KRICT, Korea (2010).
- J. Jegal, K. M. Cho, and B. K. Song, Research trends of biomass based polymeric materials, Polym. Sci. Technol., 19, 307-317 (2008).
- C. -H. Hong, B. U. Nam, and D. -S. Han, The present situation and prediction of biomass-based nylon, Polym. Sci. Technol., 21, 321-325 (2010).
- M. T. Mussser, Adipic acid, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, Germany (2000).
- W. Niu, M. Draths, and J. W. Frost, Benzene-free synthesis of adipic acid, Biotechnol. Prog., 18, 201-211 (2002). https://doi.org/10.1021/bp010179x
- T. R. Boussie, E. L. Dias, Z. M. Fresco, U. J. Murphy, V. J. Shoemaker, R. Archer, and H. Jiang, Production of adipic acid and derivatives from carbohydrate-containing materials, US Patent 0317823 A1 (2010).
- T. R. Boussie, E. L. Dias, Z. M. Fresco, and U. J. Murphy, Production of glutaric acid and derivatives from carbohydrate-containing materials, US Patent 0317825 A1 (2010).
- T. R. Boussie, E. L. Dias, Z. M. Fresco, U. J. Murphy, V. J. Shoemaker, R. Archer, and H. Jiang, Composition of matter, US Patent 0218318 A1 (2011).
- T. R. Boussie, E. L. Dias, Z. M. Fresco, U. J. Murphy, V. J. Shoemaker, R. Archer, and H. Jiang, Adipic acid composition, WO 2011/108051 A1 (2011).
- A. M. Unrau, Constitution of a galactomannoglycan from the seed of Leucaena glauca, J. Org. Chem., 24, 3097-3263 (1961).
- H. Howell and G. S. Fisher, The dissociation constants of some of the terpene acid, J. Am. Chem. Soc., 80, 6316-6319 (1958). https://doi.org/10.1021/ja01556a038
- S. Qu, Y. Dang, M. Wen, and Z. Wang, Mechanism of the methyltrioxorhenium-catalyzed deoxydehydration of polyols: A new pathway revealed, Chem. Eur. J., 19, 3827-3832 (2013). https://doi.org/10.1002/chem.201204001
-
P. Liu and K. M. Nicholas, Mechanism of sulfite-driven,
$MeReO_3$ catalyzed deoxydehydration of glycols, Organometallics, 32, 1821-1831 (2013). https://doi.org/10.1021/om301251z - S. Liu, A. Senocak, J. L. Smeltz, L. Yang, B. Wegenhart, J. Yi. H. I. Kenttamaa, E. A. Ison, and M. M. Abu-Omar, Mechanism of MTO-catalyzed deoxydehydration of diols to alkenes using sacrificial alcohols, Organometallics, 32, 3210-3219 (2013). https://doi.org/10.1021/om400127z
- S. Vlitiri, G. Chapman, I. Ahmad, and K. M. Nicolas, Rheniumcatalyzed deoxydehydration of glycols by sulfite, Inorg. Chem., 49, 4744-4746 (2010). https://doi.org/10.1021/ic100467p
- I. Ahmad, G. Chanpmann, and K. M. Nicholas, Sulfite-driven, oxorhenium-catalyzed deoxydehydration of glycols, Organometallics, 30, 2810-2818 (2011). https://doi.org/10.1021/om2001662
-
G. K. Cook and M. A. Andrews, Toward nonoxidative routes to oxygenated organics: stereospecific deoxydehydration of diols and polyols to alkenes and allylic alcohols catalyzed by the metal oxo complex
$(C_5Me_5)ReO_3$ , J. Am. Chem. Soc., 118, 9448-9449 (1996). https://doi.org/10.1021/ja9620604 -
J. E. Ziegler, M. J. Zdilla, A. J. Evans, and M. M. Abu-Omar,
$H_2$ -driven deoxygenation of epoxides and diols to alkenes catalyzed by methyltrioxorhenium, Inorg. Chem., 48, 9998-10000 (2009). https://doi.org/10.1021/ic901792b - E. Arceo, J. A. Eiiman, and R. G. Bergman, Rhenium-catalyzed didehydroxylation of vicinal diols to alkenes using a simple alcohol as a reducing agent, J. Am. Chem. Soc., 132, 11408-11409 (2010). https://doi.org/10.1021/ja103436v
- J. O. Metzger, Catalytic deoxygenation of carbohydrate renewable resources, ChemCatChem, 5, 680-682 (2013). https://doi.org/10.1002/cctc.201200796
- M. Shiramizu and F. D. Toste, Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration, Angew. Chem. Int. Ed., 52, 12905-12909 (2013). https://doi.org/10.1002/anie.201307564
- X. Li, D. Wu, T. Lu, G, Yi, H. Su, and Y. Zhang, Highly efficient chemical process to convert mucic acid into adipic acid and DFT studies of the mechanism of the rhenium-catalyzed deoxydehydration, Angew. Chem. Int. Ed., 53, 1-6 (2014). https://doi.org/10.1002/anie.201310509
- V. Canale, L. Tonucci, M. Bressan, and N. d'Alessandro, Deoxydehydration of glycerol to allyl alcohol catalyzed by rhenium derivatives, Catal. Sci. Technol., 4, 3697-3704 (2014). https://doi.org/10.1039/C4CY00631C
- G. Chapman Jr. and K. M. Nicholas, Vanadium-catalyzed deoxydehydration of glycols, Chem. Commun., 49, 8199-8201 (2013). https://doi.org/10.1039/c3cc44656e
- L. Hills, R. Moyano, F. Montilla, A. Pastor, A. Galindo, E. Alvarez, F. Marchetti, and C. Pettinari, Dioxomolybdenum (VI) complexes with acylpyrazolonate ligands: Synthesis, structures, and catalytic properties, Eur. J. Inorg. Chem., 19, 3352-3361 (2013).
- J. R. Dethlesen, D. Lupp, B. Oh, and P. Fristrup, Molybdenum-catalyzed deoxydehydration of vicinal diols, ChemSusChem, 7, 425-428 (2014). https://doi.org/10.1002/cssc.201300945
- S. Li and Y. Zhang, Highly efficient process for the conversion of glycerol to acrylic acid via gas phase catalytic oxidation of an allyl alcohol intermediate, ACS Catal., 6, 143-150 (2016). https://doi.org/10.1021/acscatal.5b01843
- J. R. Dethlefsen and P. Fristrup, Rhenium-catalyzed deoxydehydration of diols and polyols, ChemSusChem, 8, 767-775 (2015). https://doi.org/10.1002/cssc.201402987
- S. Raju, M. Moret, and R. J. M. K. Gebbink, Rhenium-catalyzed dehydration and deoxydehydration of alcohols and polyols: Opportunities for the formation of olefins from biomass, ACS Catal., 5, 281-300 (2015). https://doi.org/10.1021/cs501511x
- S. C. Ameta, P. B. Punjabi, R. Ameta, and C. Ameta, Microwave-assisted Organic Synthesis: A Green Chemical Approach, Apple Academic Press, Oakville, Canada (2015).
- P. Lidstrom, J. Tierney, B. Wathey, and J. Westman, Microwave assisted organic synthesis-a review, Tetrahedron, 57, 9225-9233 (2001). https://doi.org/10.1016/S0040-4020(01)00906-1
- J. Jacob, Microwave assisted reactions in organic chemistry: A review of recent advances, Int. J. Chem., 4, 29-43 (2012).
- Y. M. Zhang, P. Wang, N. Han, and H. F. Lei, Microwave irradiation: A novel method for rapid synthesis of D, L-Lactide, Macromol. Rapid Commun., 28, 417-421 (2007). https://doi.org/10.1002/marc.200600668
- J. M. H. Dirkx and H. S. van der Vaan, The oxidation of glucose with platinum on carbon as catalyst, J. Catal., 67, 1-13 (1981). https://doi.org/10.1016/0021-9517(81)90256-6
- J. M. H. Dirkx and H. S. van der Vaan, The oxidation of gluconic acid with platinum on carbon as catalyst, J. Catal., 67, 14-20 (1981). https://doi.org/10.1016/0021-9517(81)90257-8