Oxidation of cyclic ketones to dicarboxylic acids

Lisicki, Dawid; Orlińska, Beata

doi:10.2478/pjct-2018-0061

Abstract

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%.

References

1. Cornils, B. & Lappe, P. (2010). Dicarboxylic Acids, Aliphatic. Ullmann’s Encyclopedia of Industrial Chemistry, Wiley- -VCH, Weinheim.10.1002/14356007.a08_523.pub2
Search in Google Scholar Back to article
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
Search in Google Scholar Back to article
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
Search in Google Scholar Back to article
4. (2017, June). Adipic Acid. Chemical Economics Handbook. Retrieved March 03, 2018, from https://ihsmarkit.com/products/adipic-acid-chemical-economics-handbook.html
Search in Google Scholar Back to article
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/i200035a010.10.1021/i200035a010
Open DOI Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
7. Weissermel, K. & Arpe, H.J. (1997). Industrial Organic Chemistry (3 th ed.). New York, British Library Cataloguing10.1002/9783527616688
Search in Google Scholar Back to article
8. Krzysztoforski, A. & Rygiel, S. (2016). Produkcja cykloheksanonu. Od fenolu do benzenu i z powrotem? Przem. Chem. 6(95), 1049-1248. DOI: 10.15199/62.2016.6.110.15199/62.2016.6.1
Search in Google Scholar Back to article
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
Search in Google Scholar Back to article
10. Teles, J.H., Hermans, I., Franz, G. & Sheldon R.A. (2015). Oxidation. Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.10.1002/14356007.a18_261.pub2
Search in Google Scholar Back to article
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: 10.15199/62.2017.7.7.10.15199/62.2017.7.7
Search in Google Scholar Back to article
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.200900020.10.1002/cssc.20090002019536755
Open DOI Search in Google Scholar Back to article
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
Search in Google Scholar Back to article
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:1009015223793.10.1023/A:1009015223793
Open DOI Search in Google Scholar Back to article
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.76.1993.10.1246/bcsj.76.1993
Search in Google Scholar Back to article
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.5020230610.10.1002/jctb.5020230610
Open DOI Search in Google Scholar Back to article
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.5040340705.10.1002/jctb.5040340705
Open DOI Search in Google Scholar Back to article
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/jo00073a026.10.1021/jo00073a026
Open DOI Search in Google Scholar Back to article
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.10.1021/op980016y
Open DOI Search in Google Scholar Back to article
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.10.1039/c4gc02333a
Open DOI Search in Google Scholar Back to article
21. Flemming, W. & Speer W. (1935). U.S. Patent No. 2,005,183.
Search in Google Scholar Back to article
22. Flemming W. (1942). U.S. Patent No. 2,299,013.10.1136/bmj.2.4261.299
Search in Google Scholar Back to article
23. Ralph, H.C. & Bergenfield, N.J. (1965). U.S. Patent Np. 3,207,783.10.1038/207783a0
Search in Google Scholar Back to article
24. Baker R.S., Washington, P. & Cohen M.A. (1966). U.S. Patent Np. 3.234.271.
Search in Google Scholar Back to article
25. Lidov, R.E. & Neck G.N.Y. (1968). U.S. Patent Np. 3,361,806.
Search in Google Scholar Back to article
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/jo00239a023.10.1021/jo00239a023
Open DOI Search in Google Scholar Back to article
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.2005.02.037.10.1016/j.cattod.2005.02.037
Open DOI Search in Google Scholar Back to article
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.2012.03.003.10.1016/j.crci.2012.03.003
Open DOI Search in Google Scholar Back to article
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/jp0459662.10.1021/jp045966216851242
Open DOI Search in Google Scholar Back to article
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.2010.07.016.10.1016/j.apcata.2010.07.016
Open DOI Search in Google Scholar Back to article
31. Fumagalli, C., Minisci, F. & Pirola, R. (2001). W.O. Patent No. 01,87815. World Intellectual Property Organization.
Search in Google Scholar Back to article
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.10.1039/b400657g15252477
Open DOI Search in Google Scholar Back to article
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. 0000024586.74168.99.10.1023/B:RJAC.0000024586.74168.99
Open DOI Search in Google Scholar Back to article
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.
Search in Google Scholar Back to article
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)60063-9.10.1016/S1004-9541(07)60063-9
Open DOI Search in Google Scholar Back to article

Oxidation of cyclic ketones to dicarboxylic acids

Abstract

Paradigm

My account