DOI: https://doi.org/10.14710/jksa.25.8.280-285

Solvent-less Oxidation of Aromatic Alcohols Using CrO3/Al2O3 under Ultrasonic Irradiation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta, Indonesia

Received: 3 Aug 2022; Revised: 30 Aug 2022; Accepted: 7 Sep 2022; Published: 30 Sep 2022.
Open Access Copyright 2022 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract
Alcohol oxidation plays an essential contribution to the chemical industry. Innovative green techniques, such as ultrasound irradiation, could be economically remarkable by enhancing reaction yield. In this research, the design and improvement of a new green ultrasound-assisted oxidation of alcohols procedure using CrO3 supported by Al2O3 with the addition of a small amount of t- butanol were reported. The oxidation of alcohols was also done without ultrasound irradiation to study the sonochemical effect. Based on FTIR and GC/MS analyses, the alcohols were effectively oxidized into their corresponding aldehydes in satisfactory yields (74–93%). The yield of the obtained aldehydes was increased by applying the ultrasonic irradiation technique, and no over-oxidation products were found. Overall, the innovative procedure offers several benefits, such as being easy to use, environmentally friendly, capable of improving yields, and having shorter oxidation times.
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Keywords: CrO3/Al2O3; oxidation; sonochemistry; ultrasound irradiation
Funding: Kementerian Riset Teknologi Dan Pendidikan Tinggi Republik Indonesia

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Section: Research Articles
Language : EN
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  1. Bradford L. Ryland, Shannon S. Stahl, Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems, Angewandte Chemie International Edition, 53, 34, (2014), 8824-8838 https://doi.org/10.1002/anie.201403110
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  3. Sugang Meng, Susheng Chang, Shifu Chen, Synergistic effect of photocatalyst CdS and thermalcatalyst Cr2O3-Al2O3 for selective oxidation of aromatic alcohols into corresponding aldehydes, ACS Applied Materials & Interfaces, 12, 2, (2019), 2531-2538 https://doi.org/10.1021/acsami.9b19473
  4. C. Parmeggiani, Camilla Matassini, F. Cardona, A step forward towards sustainable aerobic alcohol oxidation: new and revised catalysts based on transition metals on solid supports, Green Chemistry, 19, 9, (2017), 2030-2050 https://doi.org/10.1039/C7GC00406K
  5. Ngadiwiyana Ngadiwiyana, Ismiyarto Ismiyarto, Jumina Jumina, Chairil Anwar, Sintesis 3-(3, 4-Dimetoksifenil)-Propanal sebagai Senyawa Antara dalam Pembuatan Turunan Antiboitik C-9154 dari Minyak Daun Cengkeh, Jurnal Kimia Sains dan Aplikasi, 11, 2, (2008), 38-42 https://doi.org/10.14710/jksa.11.2.38-42
  6. Lianyue Wang, SenSen Shang, Guosong Li, Lanhui Ren, Ying Lv, Shuang Gao, Iron/ABNO-catalyzed aerobic oxidation of alcohols to aldehydes and ketones under ambient atmosphere, The Journal of Organic Chemistry, 81, 5, (2016), 2189-2193 https://doi.org/10.1021/acs.joc.6b00009
  7. Maximilian N. Kopylovich, Ana P. C. Ribeiro, Elisabete C. B. A. Alegria, Nuno M. R. Martins, Luísa M. D. R. S. Martins, Armando J. L. Pombeiro, Catalytic oxidation of alcohols: Recent advances, Advances in Organometallic Chemistry, 63, (2015), 91-174 https://doi.org/10.1016/bs.adomc.2015.02.004
  8. Maulidan Firdaus, Triana Kusumaningsih, Annisa Istiqomah, Grinding not stirred, solvent-less oxidation of alcohols using CrO3/SiO2, Journal of Chemical Technology and Metallurgy, 57, 1, (2022), 96-100
  9. Walid Amer, Karima Abdelouahdi, Hugo R. Ramananarivo, Mohamed Zahouily, Mokhtar El Essassi, Aziz Fihri, Abderrahim Solhy, Oxidation of benzylic alcohols into aldehydes under solvent-free microwave irradiation using new catalyst-support system, Current Organic Chemistry, 17, 1, (2013), 72-78 http://dx.doi.org/10.2174/138527213805289132
  10. María Elena González-Núñez, Rossella Mello, Andrea Olmos, Rafael Acerete, Gregorio Asensio, Oxidation of alcohols to carbonyl compounds with CrO3.SiO2 in supercritical carbon dioxide, The Journal of Organic Chemistry, 71, 3, (2006), 1039-1042 https://doi.org/10.1021/jo052137j
  11. A. R. Kiasat, F. Kazemi, K. Nourbakhsh, CrO3/Al2O3: Rapid oxidation of alcohols to carbonyl compounds in a solvent-free system, ChemInform, 36, 46, (2005), 1524-1526 https://doi.org/10.1002/chin.200546041
  12. Roger A. Sheldon, Fundamentals of green chemistry: efficiency in reaction design, Chemical Society Reviews, 41, 4, (2012), 1437-1451 https://doi.org/10.1039/C1CS15219J
  13. Juan C. Colmenares, Weiyi Ouyang, Manuel Ojeda, Ewelina Kuna, Olga Chernyayeva, Dmytro Lisovytskiy, Sudipta De, Rafael Luque, Alina M. Balu, Mild ultrasound-assisted synthesis of TiO2 supported on magnetic nanocomposites for selective photo-oxidation of benzyl alcohol, Applied Catalysis B: Environmental, 183, (2016), 107-112 https://doi.org/10.1016/j.apcatb.2015.10.034
  14. Fernando Sineriz, Christine Thomassigny, Ji-Dong Lou, Recent advances in solvent-free oxidation of alcohols, Current Organic Synthesis, 1, 2, (2004), 137-154 http://dx.doi.org/10.2174/1570179043485376
  15. Maulidan Firdaus, Nestri Handayani, Lina Tri Marfu’ah, Reduction of Aldehydes Using Sodium Borohydride under Ultrasonic Irradiation, Indonesian Journal of Chemistry, 16, 2, (2016), 229-232 https://doi.org/10.22146/ijc.21168
  16. Ali Maleki, Green oxidation protocol: Selective conversions of alcohols and alkenes to aldehydes, ketones and epoxides by using a new multiwall carbon nanotube-based hybrid nanocatalyst via ultrasound irradiation, Ultrasonics Sonochemistry, 40, (2018), 460-464 https://doi.org/10.1016/j.ultsonch.2017.07.020
  17. Vaishakh Nair, Juan Carlos Colmenares, Dmytro Lisovytskiy, Ultrasound assisted ZnO coating in a microflow based photoreactor for selective oxidation of benzyl alcohol to benzaldehyde, Green Chemistry, 21, 6, (2019), 1241-1246 https://doi.org/10.1039/C8GC03131B
  18. Başak Savun-Hekimoğlu, A review on sonochemistry and its environmental applications, Acoustics, 2, 4, (2020), 766-775 https://doi.org/10.3390/acoustics2040042
  19. Ali Maleki, Jamal Rahimi, Oleg M. Demchuk, Agnieszka Z. Wilczewska, Radomir Jasiński, Green in water sonochemical synthesis of tetrazolopyrimidine derivatives by a novel core-shell magnetic nanostructure catalyst, Ultrasonics Sonochemistry, 43, (2018), 262-271 https://doi.org/10.1016/j.ultsonch.2017.12.047
  20. Ali Maleki, Morteza Aghaei, Ultrasonic assisted synergetic green synthesis of polycyclic imidazo (thiazolo) pyrimidines by using Fe3O4@clay core-shell, Ultrasonics Sonochemistry, 38, (2017), 585-589 https://doi.org/10.1016/j.ultsonch.2016.08.024
  21. MS NIST, in, National Institute of Standards and Technology Gaithersburg, USA, 2005,
  22. Susan Budavari, Maryadele J. O’Neil, Ann Smith, Patricia. E. Heckelman, The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 11 ed., Merck and Co., Inc., Rahway, The USA, 1989,
  23. Shawn Pugh, Rebekah McKenna, Ibrahim Halloum, David R. Nielsen, Engineering Escherichia coli for renewable benzyl alcohol production, Metabolic Engineering Communications, 2, (2015), 39-45 https://doi.org/10.1016/j.meteno.2015.06.002
  24. Kakasaheb Y. Nandiwale, Ashwini M. Pande, Vijay V. Bokade, One step synthesis of ethyl levulinate biofuel by ethanolysis of renewable furfuryl alcohol over hierarchical zeolite catalyst, RSC Advances, 5, 97, (2015), 79224-79231 https://doi.org/10.1039/C5RA13520F
  25. Maulidan Firdaus, Ahmad Ainurofiq, Aulia Vellarani, A New Approach for the Synthesis of p-Anisyl Ethyl Fumarate: A C-9154 Antibiotic Analogue, Chemistry Bulgarian Journal of Science Education, 25, 6, (2016), 874-880

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