Recent developments in maleic acid synthesis from bio-based chemicals

Sustainable Chemical Processes

Robert Wojcieszak⁵  Francesco Santarelli¹  Sébastien Paul³  Franck Dumeignil²  Fabrizio Cavani¹  Renato V Gonçalves⁴ 

[1] Dipartimento di Chimica Industriale “Toso Montanari”, Università di Bologna, Viale Risorgimento 4, Bologna, 40136, Italy

[2] Institut Universitaire de France, IUF, Maison des Universités, 103 Boulevard Saint-Michel, Paris 75005, France

[3] Ecole Centrale de Lille, ECLille, Cité Scientifique, Villeneuve d’Ascq, 59650, France

[4] Institute of Chemistry, USP, Av. Professor Lineu Prestes, 748, São Paulo 05508-000, SP, Brazil

[5] CNRS UMR 8181, Unité de Catalyse et Chimie du Solide (UCCS), Université Lille 1 Sciences et Technologies, Villeneuve d’Ascq Cedex, 59655, France

关键词: Nanomaterials;    Oxidation reaction;    HMF;    Furan;    Furfural;    Heterogeneous catalysis;    Maleic acid;   

Others  :  1219290
DOI  :  10.1186/s40508-015-0034-5

 received in 2014-11-27, accepted in 2015-06-02,  发布年份 2015

【 摘 要 】

This review paper presents the current state of the art on maleic acid synthesis from biomass-derived chemicals over homogeneous or heterogeneous catalysts. It is based on the most recent publications on the topic, which are discussed in details with respect to the observed catalytic performances. The recent developments and the technical drawbacks in the gas and the liquid phases are also reported. In addition, recent results on the mechanistic aspect are discussed giving insights into the probable reaction mechanisms depending on the starting molecule (furan, furfural and 5-hydroxymethylfurfural).

【 授权许可】

   
2015 Wojcieszak et al.

【 图 表 】

Figure1.

Figure2.

【 参考文献 】

• [1]Hoffman RL (1980) Monsanto Company. US Patent, US 4238572 A.. http://www.google.com/patents/US4238572 webcite
• [2]Sabu T, Kuruvilla J, Malhotra SK, Goda K, Sreekala MK (eds) (2012) Polymer Composites, Macro- and Microcomposites, vol 1. ISBN 978-3-527-32624-2
• [3]Otto G: Piringer ALB: plastic packaging materials for food: barrier function, mass transport, quality assurance, and legislation. Wiley-VCH, New York; 2008.
• [4]Yang CQ, Chen D, Guan J, He Q: Cross-linking cotton cellulose by the combination of maleic acid and sodium hypophosphite. 1. fabric wrinkle resistance. Indus Eng Chem Res 2010, 49:8325-8332.
• [5]Klaus Weissermel H-JA (2008) Industrial organic chemistry, 3rd, Completely Revised Edition. Wiley, New York
• [6]Mabee W, Gregg D, Saddler J: Assessing the emerging biorefinery sector in Canada. Appl Biochem Biotechnol 2005, 123:765-778.
• [7]Lohbeck K, Haferkorn H, Fuhrmann W, Fedtke N (2000) Maleic and fumaric acids. In: Ullmann’s encyclopedia of industrial chemistry. Wiley, GmbH & Co. KGaA
• [8]Doscher CK, Kane JH, Cragwall GO, Staebner WH: Industrial applications of fumaric acid. Indus Eng Chem 1941, 33:315-319.
• [9]Felthouse TR, Burnett JC, Horrell B, Mummey MJ, Kuo Y-J (2001) Maleic anhydride, maleic acid, and fumaric acid. In: Kirk-Othmer Encyclopedia of Chemical Technology, Wiley
• [10]Skinner WA, Tieszen D: Production of maleic acid by oxidizing butenes. Ind Eng Chem 1961, 53:557-558.
• [11]Beach LK (1951) Cis-butene oxidation. US Patent, US 2537568 A.. http://www.google.fr/patents/US2537568 webcite
• [12]Slotterbeck OC, Tribit SW (1941) Preparation of maleic acid. Google Patents
• [13]Harry O, Mitchell B, Russell JL (1964) Preparation of fumaric acid by catalytically isomerizing maleic acid produced by the oxidation of butene-2. Google Patents
• [14]Weiss Downs: Catalytic oxidation of benzene to maleic acid. J Chem Educ 1925, 2:1178.
• [15]Bhattacharyya SK, Venkataraman N: Catalytic vapour-phase oxidation of benzene to maleic acid. J Appl Chem 1958, 8:728-737.
• [16]Cornils B (2004) Handbook of commercial catalysts. In: Rase HF (eds) Heterogeneous catalysts. Angew Chem Int Ed 43:2324–2325
• [17]Xu Q, Li S, Huang H, Wen J: Key technologies for the industrial production of fumaric acid by fermentation. Biotechnol Adv 2012, 30:1685-1696.
• [18]Das RK, Brar SK, Verma M (2014) Enhanced fumaric acid production from brewery wastewater by immobilization technique. J Chem Technol Biotechnol
• [19]Roa Engel C, Straathof AJ, Zijlmans T, van Gulik W, van der Wielen LM (2008) Fumaric acid production by fermentation. Appl Microbiol Biotechnol 78:379–389
• [20]Podgorska E, Kasprzak M, Szwajgier D (2004) Fumaric acid production by rhizpous nigricans and rhizopus oryzae using apple juice. Pol J Food Nutr Sci 13/54:47–50
• [21]Lichtenthaler FW (2000) Carbohydrates as organic raw materials. In: Ullmann’s encyclopedia of industrial chemistry. Wiley, GmbH & Co. KGaA
• [22]Milbrandt A, Kinchin C, McCormick R (2013) The feasibility of producing and using biomass-based diesel and jet fuel in the United States. National Renewable Energy Laboratory, US, Department of Energy, Technical Report NREL/TP-6A20-58015.. http://www.nrel.gov/docs/fy14osti/58015.pdf webcite
• [23]Shahbazali E (2013) Biorefinery: from biomass to chemicals and fuels. In: Volker H, De Gruyter (eds) Green Processing and Synthesis, vol 2. No 1 pp 87–88
• [24]Visioli L, Enzweiler H, Kuhn R, Schwaab M, Mazutti M: Recent advances on biobutanol production. Sustain Chem Process 2014, 2:15. BioMed Central Full Text
• [25]Somerville C, Youngs H, Taylor C, Davis SC, Long SP: Feedstocks for lignocellulosic biofuels. Science 2010, 329:790-792.
• [26]Alonso DM, Bond JQ, Dumesic JA: Catalytic conversion of biomass to biofuels. Green Chem 2010, 12:1493-1513.
• [27]Corma A, delaTorre O, Renz M, Villandier N (2011) Production of high-quality diesel from biomass waste products. Angew Chem Int Edn 50:2375–2378
• [28]Aresta M, Dibenedetto A, Dumeignil F (eds) from biomass to chemicals and fuels. De Gruyter, ISBN: 978-3-11-026028-1
• [29]Triantafyllidis K, Lappas A, Stöcker M (2013) The role of catalysis for the sustainable production of bio-fuels and bio-chemicals. Elsevier
• [30]Guo H, Yin G: Catalytic aerobic oxidation of renewable furfural with phosphomolybdic acid catalyst: an alternative route to maleic acid. J Phys Chem C 2011, 115:17516-17522.
• [31]Du Z, Ma J, Wang F, Liu J, Xu J: Oxidation of 5-hydroxymethylfurfural to maleic anhydride with molecular oxygen. Green Chem 2011, 13:554-557.
• [32]Shi S, Guo H, Yin G: Synthesis of maleic acid from renewable resources: catalytic oxidation of furfural in liquid media with dioxygen. Catal Commun 2011, 12:731-733.
• [33]Choudhary H, Nishimura S, Ebitani K: Highly efficient aqueous oxidation of furfural to succinic acid using reusable heterogeneous acid catalyst with hydrogen peroxide. Chem Lett 2012, 41:409-411.
• [34]Muzychenko GF, Badovskaya LA, Kul’nevich VG: Role of water in the oxidation of furfural with hydrogen peroxide. Chem Heterocycl Compd 1972, 8:1311-1313.
• [35]Fagundez NA, Agirrezabal-Telleria I, Arias P, Fierro JLG, Mariscal Lopez R, Lopez Granados M: Aqueous-phase catalytic oxidation of furfural with H 2 O 2 : high yield of maleic acid by using titanium silicalite-1. RSC Adv 2014, 4:54960-54972.
• [36]Nielsen ER: Vapor phase oxidation of furfural. Indus Eng Chem 1949, 41:365-368.
• [37]Sessions WV: Catalytic oxidation of furfural in the vapor phase. J Am Chem Soc 1928, 50:1696-1698.
• [38]Zumstein F (1929) A process for the preparation of maleic acid. Patent DE478726 C.. http://www.google.je/patents/DE478726C?cl=en webcite
• [39]Zurnetein F (1934) Process for preparing maleic anhydride and maleic acid. American Patent 1956482
• [40]Alonso-Fagúndez N, Granados ML, Mariscal R, Ojeda M: Selective conversion of furfural to maleic anhydride and furan with VO x /Al 2 O 3 catalysts. Chem Sus Chem 2012, 5:1984-1990.
• [41]Chun WSLYLFHCY (2009) Catalytic oxidation of furfural in vapor-gas phase for producing maleic anhydride. Chem Ind Eng Prog 28:10–19
• [42]Kreile DR, Slavinskaya VA, Shimanskaya MV, Lukevits EY: The reactivity of furan compounds in vapor-phase catalytic oxidation. Chem Heterocycl Compd 1969, 5:429-430.
• [43]Badovskaya LA, Povarova LV: Oxidation of furans (Review). Chem Heterocycl Comp 2009, 45:1023-1034.
• [44]Lan J, Chen Z, Lin J, Yin G: Catalytic aerobic oxidation of renewable furfural to maleic anhydride and furanone derivatives with their mechanistic studies. Green Chem 2014, 16:4351-4358.
• [45]Murthy MS, Rajamani K: Kinetics of vapour phase oxidation of furfural on vanadium catalyst. Chem Eng Sci 1974, 29:601-609.
• [46]Choudhary H, Nishimura S, Ebitani K: Metal-free oxidative synthesis of succinic acid from biomass-derived furan compounds using a solid acid catalyst with hydrogen peroxide. Appl Catal A General 2013, 458:55-62.