Oxidation of cyclic ketones to dicarboxylic acids

• Autorzy: Lisicki D. , Orlińska B.

Identyfikatory

DOI

10.2478/pjct-2018-0061

• Języki publikacji: EN

Abstrakty

EN

This paper reports the results of studies concerning an alternative method of obtaining dicarboxylic acids, which consist of the oxidation of cyclic ketones with oxygen or air. The raw materials used were cyclopentanone, cycloheptanone, cyclooctanone, cyclododecanone, 1-tetralon, 2-methylhexanone, 3-methylcyclohexanone and 4-methylcyclohexanone. Oxidation reactions were conducted at 70-100°C, under pressure of 0.1 or 0.4 MPa, for 6 h, utilizing the salts of transition metals as catalyst and acetic acid as solvent. For example, when cyclopentanone was oxidized in the presence of Mn(II) salt, a conversion above 98% and selectivity to glutaric acid up to 68% were obtained. Among synthesized dicarboxylic acids, 1,12-dodecanoic acid was obtained with the highest selectivity of 76%.

Słowa kluczowe

EN

Dicarboxylic acids; cyclic ketones; oxidation; cyclopentanone; glutaric acid

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2018
• Tom: Vol. 20, nr 4
• Strony: 102--107
• Opis fizyczny: Bibliogr. 35 poz., rys., tab.

Twórcy

autor

Lisicki D.

• Silesian University of Technology, Faculty of Chemistry, Department of Chemical Organic Technology and Petrochemistry, Krzywoustego 4, 44-100 Gliwice, Poland

autor

Orlińska B.

• Silesian University of Technology, Faculty of Chemistry, Department of Chemical Organic Technology and Petrochemistry, Krzywoustego 4, 44-100 Gliwice, Poland

Bibliografia

• 1. Cornils, B. & Lappe, P. (2010). Dicarboxylic Acids, Aliphatic. Ullmann’s Encyclopedia of Industrial Chemistry, Wiley- -VCH, Weinheim.
• 2. (2018, Febuary). Malic Acid Market Size, Share, Trend Analysis Report By End-use (Beverage, Confectionery, Personal Care & Cosmetics), By Region, Competitive Landscape, And Segment Forecasts, 2014-2024. Retrieved March 03, 2018, from https://www.grandviewresearch.com/industry-analysis/malic-acid-market
• 3. (2015, November). Another biobased dicarboxylic acid moves toward commercial production, by Verdezyne. Retrieved March 03, 2018, from https://www.biobasedpress.eu/2015/11/another-biobased-dicarboxylic-acid-comes-into-commercialproduction-by-verdezyne
• 4. (2017, June). Adipic Acid. Chemical Economics Handbook. Retrieved March 03, 2018, from https://ihsmarkit.com/products/adipic-acid-chemical-economics-handbook.html
• 5. Krzysztoforski, A., Wojcik, Z., Pohorecki, R. & Baldyga, J. (1986). Industrial contribution to the reaction engineering of cyclohexane oxidation. Ind. Eng. Chem. Process Des. Dev. Industrial 25(4), 894-898. DOI: 10.1021/i200035a010.
• 6. Oczkowicz, S., Rygiel S., Wais, J., Koziol, A., Gruszka, M., Kondrat, A., Pohorecki, R., Wierzchowski, P., Moniuk, W., Krzysztoforski, A., Mijal, W., Wójcik, Z. & Zylinski, M. (2006). EP Patents No. 1,720,641. Paris, European Patent Office.
• 7. Weissermel, K. & Arpe, H.J. (1997). Industrial Organic Chemistry (3 th ed.). New York, British Library Cataloguing.
• 8. Krzysztoforski, A. & Rygiel, S. (2016). Produkcja cykloheksanonu. Od fenolu do benzenu i z powrotem? Przem. Chem. 6(95), 1049-1248. DOI: 10.15199/62.2016.6.1
• 9. (2015, September). Global Markets for Adipic Acid. Retrieved March 03, 2018, from http://www.researchandmarkets.com/reports/3641969/global-markets-for-adipic-acid#relc2
• 10. Teles, J.H., Hermans, I., Franz, G. & Sheldon R.A. (2015). Oxidation. Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.
• 11. Lisicki, D., Dobras, G., Orlińska, B. & Zawadiak, J. (2017). Metody otrzymywania kwasu adypinowego o potencjalnym zastosowaniu przemysłowym. Przem. Chem. 96(7), 1485-1489. DOI: 10.15199/62.2017.7.7.
• 12. Cavani, F. & Teles, J.H. (2009). Sustainability in catalytic oxidation: An alternative approach or a structural evolution? Chem. Sus. Chem. 2(6), 508-534. DOI: 10.1002/cssc.200900020.
• 13. (1998, December). One Step Phenol from Benzene by the AlphOx Process. Retrieved March 03, 2018, from https://ihsmarkit.com/products/chemical-technology-pep-reviews-onestep-phenol-from-benzene-1998.html
• 14. Notté, P.P. (2000). The AlphOx TM process or the onestep hydroxylation of benzene into phenol by nitrous oxide. Understanding and tuning the ZSM-5 catalyst activities. Top. Catal.13, 387-394. DOI: 10.1023/A:1009015223793.
• 15. Shimizu, A., Tanaka, K., Ogawa, H., Matsuoka, Y., Fujimori, M., Nagamori, Y., Hamachi, H. & Kimura, K. (2003). An Industrial Process for Adipic Acid Production by the Liquid- Phase Oxidation of Cyclohexanone with Molecular Oxygen. Bull. Chem. Soc. Jpn. 76(10), 1993-2001. DOI:10.1246/bcsj.76.1993.
• 16. Kamath, S.S. & Chandalia, S.B. (1973). Liquid phase oxidation of cyclohexanone to adipic acid by air in acetic acid solution. J. Appl. Chem. Biotechnol. 23(6), 469-478. DOI: 10.1002/jctb.5020230610.
• 17. Rao, D.G. & Raghunathan, T.S. (1984). Oxidation of Cyclohexanone to Adipic Acid with a Cobalt Acetate/Oxygen/ Acetic Acid System. J. Chem. Tech. Biotechnol. 34A, 381-386. DOI: 10.1002/jctb.5040340705.
• 18. Atlamsani, A., Brégeault, J.M. & Ziyad, M. (1993). Oxidation of 2-Methylcyclohexanone and Cyclohexanone by Dioxygen Catalyzed by Vanadium-Containing Heteropolyanions. J. Org. Chem. 58(21), 5663-5665. DOI: 10.1021/jo00073a026.
• 19. Iwahama, T., Syojyo, K., Sakaguchi, S. & Ishii, Y. (1998). Direct Conversion of Cyclohexane into Adipic Acid with Molecular Oxygen Catalyzed by N -Hydroxyphthalimide Combined with Mn(acac) 2 and Co(OAc) 2. Org. Process Res. Dev. 2(4), 255-260. DOI: 10.1021/op980016y.
• 20. Zou, G., Zhong, W., Mao, L., Xu, Q., Xiao, J., Yin, D., Xiao, Z., Kirk, S.R. & Shu, T. (2015). A non-nitric acid method of adipic acid synthesis: Organic solvent- and promoter-free oxidation of cyclohexanone with oxygen over hollow-structured Mn/TS-1 catalysts. Green Chem. 17(3), 1884-1892. DOI: 10.1039/c4gc02333a.
• 21. Flemming, W. & Speer W. (1935). U.S. Patent No. 2,005,183.
• 22. Flemming W. (1942). U.S. Patent No. 2,299,013.
• 23. Ralph, H.C. & Bergenfield, N.J. (1965). U.S. Patent Np. 3,207,783.
• 24. Baker R.S., Washington, P. & Cohen M.A. (1966). U.S. Patent Np. 3.234.271.
• 25. Lidov, R.E. & Neck G.N.Y. (1968). U.S. Patent Np. 3,361,806.
• 26. Osowska-Pacewicka, K. & Alper, H. (1988). Oxidation of Cyclic Ketones Catalyzed by Polyethylene Glycol and Rhenium Carbonyl under Basic and Exceptionally Mild Conditions, J. Org. Chem. 2(1), 808-810. DOI: 10.1021/jo00239a023.
• 27. Besson, M., Gallezot, P., Perrard, A. & Pinel, C. (2005). Active carbons as catalysts for liquid phase reactions. Catal. Today, 102-103, 160-165. DOI: 10.1016/j.cattod.2005.02.037.
• 28. Dakkach, M., Atlamsani, A. & Sebti, S. (2012). Le phosphate naturel modifié au vanadium : un nouveau catalyseur pour l’oxydation des cycloalcanones et des α-cétols en présence de l’oxygène moléculaire. C. R. Chimie 15(6), 482-492. DOI: 10.1016/j.crci.2012.03.003.
• 29. Besson, M., Gauthard, F., Horvath, B. & Gallezot, P. (2005). Catalytic oxidation with air of cyclohexanone to dicarboxylic acids on synthetic carbons. Effect of supported metals and solvents. J. Phys. Chem. B 109(6), 2461-2467. DOI: 10.1021/jp0459662.
• 30. Vennat, M. & Brégeault, J.M. (2010). Oxidative cleavage of cycloalkanones with dioxygen catalyzed by supported catalysts or homogeneous systems: Evidence for novel active ruthenium (II) and/or (III) species. Appl. Catal. A-Gen. 386(1-2), 9-15. DOI: 10.1016/j.apcata.2010.07.016.
• 31. Fumagalli, C., Minisci, F. & Pirola, R. (2001). W.O. Patent No. 01,87815. World Intellectual Property Organization.
• 32. Vennat, M., Bregeault, J.M. & Herson, P. (2004). Mixed crystals containing the dioxo complex [[Ph3SiO]2VO2]- and novel pentacoordinated oxoperoxo complex [[Ph3SiO]2VO- (O2)]-: X-ray crystal structure and assessment as oxidation catalysts. Dalton Trans. (6), 908-13. DOI: 10.1039/b400657g.
• 33. Syroezhko, A.M. & Begak, O.Yu. (2004). Ozonolysis of Methylcyclohexanols and Methylcyclohexanones. Russian J. Appl. Chem. 77(1), 102-105 . DOI: 10.1023/B:RJAC. 0000024586.74168.99.
• 34. Renukdas, S.V., Patil, S. & Patel, N.T. (2014). Kinetics of oxidation of 3-methyl cyclohexanone by periodate catalyzed by Ru(III) in alkaline medium. Physical Chem. 9(4), 141-143.
• 35. Song, W., Ma, P., Fan, L. & Xiang, Z. (2007). Solubility of Glutaric Acid in Cyclohexanone, Cyclohexanol, Their Five Mixtures and Acetic Acid. Chin. J. Chem. Eng. 15(2), 228-232. DOI: 10.1016/S1004-9541(07)60063-9.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).