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Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2

Year 2024, Volume: 6 Issue: 2, 78 - 90, 20.12.2024
https://doi.org/10.51435/turkjac.1503828

Abstract

This study aimed to improve the conditions for the oxidation of benzaldehyde to benzoic acid using chlorine dioxide generated from sodium chlorite, across various pH ranges and different catalysts. The powerful oxidation capability of chlorine dioxide played a crucial role in enhancing the kinetic efficiency of the reactions. In our research, we examined various reaction conditions, including sodium dihydrogen phosphate, sodium dihydrogen phosphate together with sodium chlorite, sodium dihydrogen phosphate combined with sodium chlorite and potassium permanganate, and sodium dihydrogen phosphate with sodium chlorite and V2O5. Additionally, different oxidation combinations were tested, such as sodium chlorite with sodium tripolyphosphate (STPP), 1-hydroxyethylidene-1,1-diphosphonic acid (HEDP), and formic acid, as well. The stabilized chlorine dioxide solution was also used directly as an oxidation reagent. The role of chlorine dioxide in these combinations significantly impacted the selectivity and yield in terms of product.
Furthermore, some Mn (III) complexes (Cat.1 and Cat.2) were used as catalysts in this study, and the findings revealed that chlorine dioxide is an effective oxidant in the selective oxidation of aromatic aldehydes to aromatic acids. For the catalytic application in buffer solutions, a leveling effect was observed. When Mn (III) complexes were used, it showed a similar leveling effect in buffer solutions with a pH >1, which was resulting in slow ClO₂ formation. With these findings it was found that the use of Mn (III) complexes in NaH2PO4+NaClO2 combination provided the highest yield in the oxidation of aromatic aldehydes to acids. These results underscore the importance of chlorine dioxide as a powerful oxidant in chemical transformation processes.

References

  • BÄCKVALL, Jan-Erling (ed.), Modern oxidation methods (2nd edition), 2011, USA, John Wiley & Sons.
  • B.O. Lindgren, T. Nilsson, Preparation of carboxylic acids from aldehydes (including hydroxylated benzaldehydes) by oxidation with chlorite, Prep Org Chem, 4, 1973, 35.
  • G. Tojo, M. Fernández, Oxidation of primary alcohols to carboxylic acids: A guide to current common practice (Basic Reactions in Organic Synthesis), (2007th edition), 2006, USA, Springer.
  • A. Raach, O. Reiser, Sodium chlorite‐hydrogen peroxide—A mild and selective reagent for the oxidation of aldehydes to carboxylic acids, J Prakt Chem, 342:6, 2000, 605-608.
  • J.M. Grill, J.W. Ogle, S.A. Miller, An efficient and practical system for the catalytic oxidation of alcohols, aldehydes, and α, β-unsaturated carboxylic acids, J Org Chem, 71:25, 2006, 9291-9296.
  • G. Pass, Practical Inorganic Chemistry: Preparations, Reactions and Instrumental Methods (2nd edition), 2013, USA, Springer Science & Business Media.
  • G. Lunn, E.B. Sansone, Destruction of Hazardous Chemicals in the Laboratory (4th edition), 2023, USA, John Wiley & Sons.
  • A. Asghar, A.A.A. Raman, W.M.A.W. Daud, Advanced oxidation processes for in-situ production of hydrogen peroxide/hydroxyl radical for textile wastewater treatment: A review, J Clean Prod, 87, 2015, 826–838.
  • H.B. Ji, β-Cyclodextrin promoted oxidation of aldehydes to carboxylic acids in water, Chin Chem Lett, 20, 2009, 139–142.
  • T. Beddoes, Davy, In A History of Chemistry (Latest edition), 1964, Palgrave, London.
  • N. Riegels, M.J. Richards, Humphry Davy: His life, works, and contribution to anesthesiology, J Am Soc Anesthesiol, 114, 2011, 1282–1288.
  • M. Zhao, Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach, J Org Chem, 64(7), 1999, 2564–2566.
  • S.B. Jonnalagadda, S. Nadupalli, Chlorine dioxide for bleaching, industrial applications and water treatment, Indian Chem Eng, 56(2), 2014, 123–136.
  • W. Gan, Y. Ge, Y. Zhong, X. Yang, The reactions of chlorine dioxide with inorganic and organic compounds in water treatment: Kinetics and mechanisms, Environ Sci Water Res Technol, 6(9), 2020, 2287–2312.
  • A.R. Mohite, R.G. Bhat, A practical and convenient protocol for the synthesis of (E)-α, β-unsaturated acids, Org Lett, 15(17), 2013, 4564–4567.
  • A.P. Krapcho, Uses of sodium chlorite and sodium bromate in organic synthesis: A review, Org Prep Proced Int, 38(2), 2009, 177–216.
  • S. Erdemir, Schiff bazı ve polimerlerinin geçiş metal komplekslerinin sentezi karakterizasyonu ve oksidasyon katalizörü olarak etkilerinin incelenmesi, Doktora Tezi, Çukurova Üniversitesi, Fen Bilimleri Enstitüsü, 2007.
  • S. Abramovici, R. Neumann, Y. Sasson, Sodium hypochlorite as oxidant in phase transfer catalytic systems: Part I. Oxidation of aromatic aldehydes, J Mol Catal, 29(3), 1985, 291–297.
  • S.D. Hicks, Non-heme manganese catalysts for on-demand production of chlorine dioxide in water and under mild conditions, J Am Chem Soc, 136, 2014, 3680–3686.
  • K. Ohkubo, Dihydroxylation of styrene by sodium chlorite with scandium triflate, J Phys Org Chem, 30(e3619), 2016, 5.
  • M.Y. Xu, Y.L. Lin, T.Y. Zhang, C.Y. Hu, Y.L. Tang, J. Deng, B. Xu, Chlorine dioxide-based oxidation processes for water purification: A review, J Hazard Mater, 436, 2022, 129195.
  • V. Rougé, Y. Lee, U. von Gunten, S. Allard, Kinetic and mechanistic understanding of chlorite oxidation during chlorination: Optimization of ClO2 pre-oxidation for disinfection byproduct control, Water Res, 220, 2022, 118515.
  • K. Furukawa, M. Shibuya, Y. Yamamoto, Chemoselective catalytic oxidation of 1,2-diols to α-hydroxy acids controlled by TEMPO–ClO2 charge-transfer complex, Org Lett, 17(9), 2015, 2282–2285.
  • J. Cubillos, S. Vásquez, C.M. de Correa, Salen manganese (III) complexes as catalysts for R-(+)-limonene oxidation, Appl Catal A Gen, 373(1-2), 2010, 57–65.
  • A.V. Kutchin, I.V. Fedorova, I.V. Loginova, I.Y. Chukicheva, Features of the use of ClO2 in the oxidation of some alkylphenols, Russ Chem Bull, 72(1), 2023, 202–212.
  • A. Westphal, A. Klinkebiel, H.M. Berends, H. Broda, P. Kurz, F. Tuczek, Electronic structure and spectroscopic properties of mononuclear manganese (III) Schiff base complexes: A systematic study on [Mn (acen) X] complexes by EPR, UV/vis, and MCD spectroscopy (X= Hal, N CS), Inorg Chem, 52(5), 2013, 2372–2387.
  • R. Habib, Method for the production of chlorine dioxide, 1993, US5380518A.
  • S.S. Nielsen, C. Tyl, B. P. Ismail, Preparation of reagents and buffers, Food Analysis Laboratory Manual (5th edition), 2017, 21–32.
  • P. Sen, D. Kara Simsek, S.Z. Yildiz, Functional zinc (II) phthalocyanines bearing Schiff base complexes as oxidation catalysts for bleaching systems, Appl Organomet Chem, 29(8), 2015, 509–516.
  • G. Kaya, Oksidasyon katalizörü olarak çeşitli koordinasyon bileşiklerinin hazırlanması, karakterizasyonu ve etkinliklerinin ölçülmesi, Doctoral Thesis, Sakarya University, Fen Bilimleri Enstitüsü, 2018.
  • E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker, L. Deng, Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane, J Am Chem Soc, 113(18), 1991, 7063–7064.
  • S.D. Hicks, S. Xiong, C. J. Bougher, G. A. Medvedev, J. Caruthers, M.M. Abu-Omar, Mechanistic study of a manganese porphyrin catalyst for on-demand production of chlorine dioxide in water, J Porphyrins Phthalocyanines, 19(01n03), 2015, 492–499.
  • P. Barman, A. S. Faponle, A. K. Vardhaman, D. Angelone, A. M. Löhr, W.R. Browne, S.P. de Visser, Influence of ligand architecture in tuning reaction bifurcation pathways for chlorite oxidation by non-heme iron complexes, Inorg Chem, 55(20), 2016, 10170–10181.
  • Z. Hu, H. Du, W.L. Man, C.F. Leung, H. Liang, T.C. Lau, Catalytic reactions of chlorite with a polypyridylruthenium (II) complex: Disproportionation, chlorine dioxide formation and alcohol oxidation, Chem Commun, 48(8), 2012, 1102–1104.
  • I. Fábián, The reactions of transition metal ions with chlorine (III), Coord Chem Rev, 216, 2001, 449–472.
  • S. Z. Yıldız, S. Dursun, The investigation of the effect of sodium chlorite and phosphonic acid catalysts on cotton bleaching process conditions, Turk J Anal Chem, 5(1), 2023, 61–69.
  • S. Dursun, S.Z. Yıldız, Eco-friendly bleaching of cotton fabrics without heating using direct process water in the presence of sodium chlorite and phosphonate, J Nat Fibers, 20(1), 2023, 2146248.

Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2

Year 2024, Volume: 6 Issue: 2, 78 - 90, 20.12.2024
https://doi.org/10.51435/turkjac.1503828

Abstract

References

  • BÄCKVALL, Jan-Erling (ed.), Modern oxidation methods (2nd edition), 2011, USA, John Wiley & Sons.
  • B.O. Lindgren, T. Nilsson, Preparation of carboxylic acids from aldehydes (including hydroxylated benzaldehydes) by oxidation with chlorite, Prep Org Chem, 4, 1973, 35.
  • G. Tojo, M. Fernández, Oxidation of primary alcohols to carboxylic acids: A guide to current common practice (Basic Reactions in Organic Synthesis), (2007th edition), 2006, USA, Springer.
  • A. Raach, O. Reiser, Sodium chlorite‐hydrogen peroxide—A mild and selective reagent for the oxidation of aldehydes to carboxylic acids, J Prakt Chem, 342:6, 2000, 605-608.
  • J.M. Grill, J.W. Ogle, S.A. Miller, An efficient and practical system for the catalytic oxidation of alcohols, aldehydes, and α, β-unsaturated carboxylic acids, J Org Chem, 71:25, 2006, 9291-9296.
  • G. Pass, Practical Inorganic Chemistry: Preparations, Reactions and Instrumental Methods (2nd edition), 2013, USA, Springer Science & Business Media.
  • G. Lunn, E.B. Sansone, Destruction of Hazardous Chemicals in the Laboratory (4th edition), 2023, USA, John Wiley & Sons.
  • A. Asghar, A.A.A. Raman, W.M.A.W. Daud, Advanced oxidation processes for in-situ production of hydrogen peroxide/hydroxyl radical for textile wastewater treatment: A review, J Clean Prod, 87, 2015, 826–838.
  • H.B. Ji, β-Cyclodextrin promoted oxidation of aldehydes to carboxylic acids in water, Chin Chem Lett, 20, 2009, 139–142.
  • T. Beddoes, Davy, In A History of Chemistry (Latest edition), 1964, Palgrave, London.
  • N. Riegels, M.J. Richards, Humphry Davy: His life, works, and contribution to anesthesiology, J Am Soc Anesthesiol, 114, 2011, 1282–1288.
  • M. Zhao, Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach, J Org Chem, 64(7), 1999, 2564–2566.
  • S.B. Jonnalagadda, S. Nadupalli, Chlorine dioxide for bleaching, industrial applications and water treatment, Indian Chem Eng, 56(2), 2014, 123–136.
  • W. Gan, Y. Ge, Y. Zhong, X. Yang, The reactions of chlorine dioxide with inorganic and organic compounds in water treatment: Kinetics and mechanisms, Environ Sci Water Res Technol, 6(9), 2020, 2287–2312.
  • A.R. Mohite, R.G. Bhat, A practical and convenient protocol for the synthesis of (E)-α, β-unsaturated acids, Org Lett, 15(17), 2013, 4564–4567.
  • A.P. Krapcho, Uses of sodium chlorite and sodium bromate in organic synthesis: A review, Org Prep Proced Int, 38(2), 2009, 177–216.
  • S. Erdemir, Schiff bazı ve polimerlerinin geçiş metal komplekslerinin sentezi karakterizasyonu ve oksidasyon katalizörü olarak etkilerinin incelenmesi, Doktora Tezi, Çukurova Üniversitesi, Fen Bilimleri Enstitüsü, 2007.
  • S. Abramovici, R. Neumann, Y. Sasson, Sodium hypochlorite as oxidant in phase transfer catalytic systems: Part I. Oxidation of aromatic aldehydes, J Mol Catal, 29(3), 1985, 291–297.
  • S.D. Hicks, Non-heme manganese catalysts for on-demand production of chlorine dioxide in water and under mild conditions, J Am Chem Soc, 136, 2014, 3680–3686.
  • K. Ohkubo, Dihydroxylation of styrene by sodium chlorite with scandium triflate, J Phys Org Chem, 30(e3619), 2016, 5.
  • M.Y. Xu, Y.L. Lin, T.Y. Zhang, C.Y. Hu, Y.L. Tang, J. Deng, B. Xu, Chlorine dioxide-based oxidation processes for water purification: A review, J Hazard Mater, 436, 2022, 129195.
  • V. Rougé, Y. Lee, U. von Gunten, S. Allard, Kinetic and mechanistic understanding of chlorite oxidation during chlorination: Optimization of ClO2 pre-oxidation for disinfection byproduct control, Water Res, 220, 2022, 118515.
  • K. Furukawa, M. Shibuya, Y. Yamamoto, Chemoselective catalytic oxidation of 1,2-diols to α-hydroxy acids controlled by TEMPO–ClO2 charge-transfer complex, Org Lett, 17(9), 2015, 2282–2285.
  • J. Cubillos, S. Vásquez, C.M. de Correa, Salen manganese (III) complexes as catalysts for R-(+)-limonene oxidation, Appl Catal A Gen, 373(1-2), 2010, 57–65.
  • A.V. Kutchin, I.V. Fedorova, I.V. Loginova, I.Y. Chukicheva, Features of the use of ClO2 in the oxidation of some alkylphenols, Russ Chem Bull, 72(1), 2023, 202–212.
  • A. Westphal, A. Klinkebiel, H.M. Berends, H. Broda, P. Kurz, F. Tuczek, Electronic structure and spectroscopic properties of mononuclear manganese (III) Schiff base complexes: A systematic study on [Mn (acen) X] complexes by EPR, UV/vis, and MCD spectroscopy (X= Hal, N CS), Inorg Chem, 52(5), 2013, 2372–2387.
  • R. Habib, Method for the production of chlorine dioxide, 1993, US5380518A.
  • S.S. Nielsen, C. Tyl, B. P. Ismail, Preparation of reagents and buffers, Food Analysis Laboratory Manual (5th edition), 2017, 21–32.
  • P. Sen, D. Kara Simsek, S.Z. Yildiz, Functional zinc (II) phthalocyanines bearing Schiff base complexes as oxidation catalysts for bleaching systems, Appl Organomet Chem, 29(8), 2015, 509–516.
  • G. Kaya, Oksidasyon katalizörü olarak çeşitli koordinasyon bileşiklerinin hazırlanması, karakterizasyonu ve etkinliklerinin ölçülmesi, Doctoral Thesis, Sakarya University, Fen Bilimleri Enstitüsü, 2018.
  • E.N. Jacobsen, W. Zhang, A.R. Muci, J.R. Ecker, L. Deng, Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane, J Am Chem Soc, 113(18), 1991, 7063–7064.
  • S.D. Hicks, S. Xiong, C. J. Bougher, G. A. Medvedev, J. Caruthers, M.M. Abu-Omar, Mechanistic study of a manganese porphyrin catalyst for on-demand production of chlorine dioxide in water, J Porphyrins Phthalocyanines, 19(01n03), 2015, 492–499.
  • P. Barman, A. S. Faponle, A. K. Vardhaman, D. Angelone, A. M. Löhr, W.R. Browne, S.P. de Visser, Influence of ligand architecture in tuning reaction bifurcation pathways for chlorite oxidation by non-heme iron complexes, Inorg Chem, 55(20), 2016, 10170–10181.
  • Z. Hu, H. Du, W.L. Man, C.F. Leung, H. Liang, T.C. Lau, Catalytic reactions of chlorite with a polypyridylruthenium (II) complex: Disproportionation, chlorine dioxide formation and alcohol oxidation, Chem Commun, 48(8), 2012, 1102–1104.
  • I. Fábián, The reactions of transition metal ions with chlorine (III), Coord Chem Rev, 216, 2001, 449–472.
  • S. Z. Yıldız, S. Dursun, The investigation of the effect of sodium chlorite and phosphonic acid catalysts on cotton bleaching process conditions, Turk J Anal Chem, 5(1), 2023, 61–69.
  • S. Dursun, S.Z. Yıldız, Eco-friendly bleaching of cotton fabrics without heating using direct process water in the presence of sodium chlorite and phosphonate, J Nat Fibers, 20(1), 2023, 2146248.
There are 37 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry (Other)
Journal Section Research Articles
Authors

Ecem Bellikan 0009-0006-8022-0215

Salih Zeki Yıldız 0000-0001-5086-8770

Gizem Boyoğlu 0009-0008-0333-6366

Ahmet Berat Karabina 0000-0001-6533-2637

Publication Date December 20, 2024
Submission Date June 24, 2024
Acceptance Date August 22, 2024
Published in Issue Year 2024 Volume: 6 Issue: 2

Cite

APA Bellikan, E., Yıldız, S. Z., Boyoğlu, G., Karabina, A. B. (2024). Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2. Turkish Journal of Analytical Chemistry, 6(2), 78-90. https://doi.org/10.51435/turkjac.1503828
AMA Bellikan E, Yıldız SZ, Boyoğlu G, Karabina AB. Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2. TurkJAC. December 2024;6(2):78-90. doi:10.51435/turkjac.1503828
Chicago Bellikan, Ecem, Salih Zeki Yıldız, Gizem Boyoğlu, and Ahmet Berat Karabina. “Catalytic Oxidation of Aromatic Aldehydes to Carboxylic Acids in Mild Conditions With NaClO2”. Turkish Journal of Analytical Chemistry 6, no. 2 (December 2024): 78-90. https://doi.org/10.51435/turkjac.1503828.
EndNote Bellikan E, Yıldız SZ, Boyoğlu G, Karabina AB (December 1, 2024) Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2. Turkish Journal of Analytical Chemistry 6 2 78–90.
IEEE E. Bellikan, S. Z. Yıldız, G. Boyoğlu, and A. B. Karabina, “Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2”, TurkJAC, vol. 6, no. 2, pp. 78–90, 2024, doi: 10.51435/turkjac.1503828.
ISNAD Bellikan, Ecem et al. “Catalytic Oxidation of Aromatic Aldehydes to Carboxylic Acids in Mild Conditions With NaClO2”. Turkish Journal of Analytical Chemistry 6/2 (December 2024), 78-90. https://doi.org/10.51435/turkjac.1503828.
JAMA Bellikan E, Yıldız SZ, Boyoğlu G, Karabina AB. Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2. TurkJAC. 2024;6:78–90.
MLA Bellikan, Ecem et al. “Catalytic Oxidation of Aromatic Aldehydes to Carboxylic Acids in Mild Conditions With NaClO2”. Turkish Journal of Analytical Chemistry, vol. 6, no. 2, 2024, pp. 78-90, doi:10.51435/turkjac.1503828.
Vancouver Bellikan E, Yıldız SZ, Boyoğlu G, Karabina AB. Catalytic oxidation of aromatic aldehydes to carboxylic acids in mild conditions with NaClO2. TurkJAC. 2024;6(2):78-90.

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