Sorbic Acid as a Renewable Resource for Atom-Economic and Selective Production of p-Toluic Acid and Alkyl-p-Toluates: Intermediates to Bioterephthalic Acid and Esters

Industrial and Engineering Chemistry Research

Volumn 54, Issue 28, 2015, Pages 7164-7168

  Bérard, Sandrine ^a   Vallée, Christophe ^a   Delcroix, Damien ^a  

^a IFP ENERGIES NOUVELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; ETHYLENE; INDUSTRIAL CHEMICALS;

ATOM ECONOMIC; COMMODITY CHEMICALS; DIELS-ALDER REACTION; RENEWABLE RESOURCE; SELECTIVE PRODUCTION; TEREPHTHALATE; TOLUIC ACIDS;

SORBIC ACID;

EID: 84937796066     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/acs.iecr.5b01972     Document Type: Article

References (34)

1. Ma, F.; Hanna, M. A. Biodiesel production: A review Bioresour. Technol. 1999, 70, 1-15 10.1016/S0960-8524(99)00025-5
2. Gallezot, P. Conversion of biomass to selected chemical products Chem. Soc. Rev. 2012, 41, 1538-1558 10.1039/C1CS15147A
3. Colonna, M.; Berti, C.; Fiorini, M.; Binassi, E.; Mazzacurati, M.; Vannini, M.; Karanam, S. Synthesis and radiocarbon evidence of terephthalate polyesters completely prepared from renewable resources Green Chem. 2011, 13, 2543-2548 10.1039/c1gc15400a
4. Balu, A. M.; Budarin, V.; Shuttleworth, P. S.; Pfaltzgraff, L. A.; Waldron, K.; Luque, R.; Clark, J. H. Valorisation of orange peel residues: Waste to biochemicals and nanoporous materials ChemSusChem 2012, 5, 1694-1697 10.1002/cssc.201200381
5. Bruijnincx, Pieter C A; Weckhuysen, B. M. Shale gas revolution: An opportunity for the production of biobased chemicals? Angew. Chem., Int. Ed. 2013, 52, 11980-11987 10.1002/anie.201305058
6. http://www.gbiresearch.com/report-store/market-reports/archive/purified-terephthalic-acid-global-market-to-2020-overcapacity-and-declining-margins-to-hinder-global-demand-in-the-short-term/contents.
7. Li, M.; Niu, F.; Busch, D. H.; Subramaniam, B. Kinetic Investigations of p -Xylene Oxidation to Terephthalic Acid with a Co/Mn/Br Catalyst in a Homogeneous Liquid Phase Ind. Eng. Chem. Res. 2014, 53, 9017-9026 10.1021/ie403446b
8. Tomás, R. A. F.; Bordado, J. C. M.; Gomes, J. F. P. p -Xylene oxidation to terephthalic acid: A literature review oriented toward process optimization and development Chem. Rev. 2013, 113, 7421-7469 10.1021/cr300298j
9. Lin, Z.; Nikolakis, V.; Ierapetritou, M. Alternative Approaches for p -Xylene Production from Starch: Techno-Economic Analysis Ind. Eng. Chem. Res. 2014, 53, 10688-10699 10.1021/ie402469j
10. Wang, B.; Gruter, G. J.; Dam, M. A.; Kriegel, R. M. Process for the preparation of benzene derivatives from furan derivatives. Patent WO14065657-A1, 2014.
11. Blommel, P.; Held, A.; Goodwin, R.; Cortright, R. Process for converting biomass to aromatic hydrocarbons. U.S. Patent US2014349361-A1, 2014.
12. Jae, J.; Coolman, R.; Mountziaris, T. J.; Huber, G. W. Catalytic fast pyrolysis of lignocellulosic biomass in a process development unit with continual catalyst addition and removal Chem. Eng. Sci. 2014, 108, 33-46 10.1016/j.ces.2013.12.023
13. Peters, M. W.; Taylor, J. D.; Jenni, M.; Manzer, L. E.; Henton, D. E. Integrated process to selectively convert renewable isobutanol to p-xylene. U.S. Patent US2011087000-A1, 2011.
14. Kraus, G. A.; Riley, S.; Cordes, T. Aromatics from pyrones: Para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate Green Chem. 2011, 13, 2734-2736 10.1039/c1gc15650k
15. Lyons, T. W.; Guironnet, D.; Findlater, M.; Brookhart, M. Synthesis of p -xylene from ethylene J. Am. Chem. Soc. 2012, 134, 15708-15711 10.1021/ja307612b
16. Williams, C. L.; Chang, C.-C.; Do, P.; Nikbin, N.; Caratzoulas, S.; Vlachos, D. G.; Lobo, R. F.; Fan, W.; Dauenhauer, P. J. Cycloaddition of Biomass-Derived Furans for Catalytic Production of Renewable p -Xylene ACS Catal. 2012, 2, 935-939 10.1021/cs300011a
17. Brandvold, T. A. Carbohydrate route to para-xylene and terephthalic acid. U.S. Patent US8314267-B2, 2012.
18. Nikbin, N.; Do, P. T.; Caratzoulas, S.; Lobo, R. F.; Dauenhauer, P. J.; Vlachos, D. G. A DFT study of the acid-catalyzed conversion of 2,5-dimethylfuran and ethylene to p -xylene J. Catal. 2013, 297, 35-43 10.1016/j.jcat.2012.09.017
19. Lin, Z.; Ierapetritou, M.; Nikolakis, V. Aromatics from Lignocellulosic Biomass: Economic Analysis of the Production of p -Xylene from 5-Hydroxymethylfurfural AIChE J. 2013, 59, 2079-2087 10.1002/aic.13969
20. Chang, C.-C.; Green, S. K.; Williams, C. L.; Dauenhauer, P. J.; Fan, W. Ultra-selective cycloaddition of dimethylfuran for renewable p -xylene with H-BEA Green Chem. 2014, 16, 585-588 10.1039/C3GC40740C
21. Shiramizu, M.; Toste, F. D. On the Diels-Alder approach to solely biomass-derived polyethylene terephthalate (PET): Conversion of 2,5-dimethylfuran and acrolein into p -xylene Chem.-Eur. J. 2011, 17, 12452-12457 10.1002/chem.201101580
22. Pacheco, J. J.; Davis, M. E. Synthesis of terephthalic acid via Diels-Alder reactions with ethylene and oxidized variants of 5-hydroxymethylfurfural Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 8363-8367 10.1073/pnas.1408345111
23. Detoni, C.; Gierlich, C. H.; Rose, M.; Palkovits, R. Selective Liquid Phase Adsorption of 5-Hydroxymethylfurfural on Nanoporous Hyper-Cross-Linked Polymers ACS Sustainable Chem. Eng. 2014, 2, 2407-2415 10.1021/sc5004264
24. Tachibana, Y.; Kimura, S.; Kasuya, K.-I. Synthesis and verification of biobased terephthalic Acid from furfural Sci. Rep. 2015, 5, 8249-8253 10.1038/srep08249
25. Frost, J. W. Preparation of trans,trans muconic acid and trans,trans muconates. U.S. Patent US2010314243-A1, 2010.
26. Averesch, N. J.; Krömer, J. O. Tailoring strain construction strategies for muconic acid production in S. cerevisiae and E. coli Metab. Eng. Commun. 2014, 1, 19-28 10.1016/j.meteno.2014.09.001
27. http://www.rnrmarketresearch.com/market-research-report-on-global-and-chinese-sorbic-acid-industry-2009-2019-market-report.html.
28. Dorko, C. L.; Ford, G. T., Jr.; Baggett, M. S.; Behling, A. R.; Carman, H. E. Sorbic Acid. In Kirk-Othmer Encyclopedia of Chemical Technology; Wiley-Interscience: Hoboken, NJ, 2008, (DOI: 10.1002/0471238961.1915180204151811.a01) (ISBN: 978-0-470-17448-7).
29. McAdams, C. A. Manufacture and use of alkyl p-toluates. U.S. Patent US2009286912-A1, 2009.
30. Dauben, W. G.; Baker, W. R. Organic reactions at high pressure. The Diels-Alder reaction of p -benzoquinone with dienic esters Tetrahedron Lett. 1982, 23, 2611-2614 10.1016/S0040-4039(00)87410-9
31. 2, oxidative dehydrogenations Synth. Commun. 1982, 12, 637-645 10.1080/00397918208061895
32. Xiao, B.; Zheng, M.; Pang, J.; Jiang, Y.; Wang, H.; Sun, R.; Wang, A.; Wang, X.; Zhang, T. Synthesis and Characterization of Poly(ethylene terephthalate) from Biomass-Based Ethylene Glycol: Effects of Miscellaneous Diols Ind. Eng. Chem. Res. 2015, 54, 5862-5869 10.1021/acs.iecr.5b00487
33. Pang, J.; Zheng, M.; Wang, A.; Zhang, T. Catalytic Hydrogenation of Corn Stalk to Ethylene Glycol and 1,2-Propylene Glycol Ind. Eng. Chem. Res. 2011, 50, 6601-6608 10.1021/ie102505y
34. Zhao, G.; Zheng, M.; Zhang, J.; Wang, A.; Zhang, T. Catalytic Conversion of Concentrated Glucose to Ethylene Glycol with Semicontinuous Reaction System Ind. Eng. Chem. Res. 2013, 52 (28) 9566-9572 10.1021/ie400989a