Humic Acid: A Green Acid Catalyzed by Acylation of Amine, Phenol, and Thiols Derivatives under Solvent-Free Conditions
- Lovely Professional University Ringgold standard institution, Chemistry Phagwara, India
- Savitribai Phule Pune University Ringgold standard institution, Chemistry Karjat, India
- Department of Engineering Chemistry, Andhra University, Visakhapatnam Hyderabad, India
- Aragen Life Science Pvt. Ltd, Mallapur Hyderabad, India
Received: 2024-08-25
Revised: 2025-07-03
Accepted: 2025-07-10
Published in Issue 2025-09-30
Published Online: 2025-07-25
Copyright (c) 2025 Shripad Patil, Atnv Sairaju, Abhishek Saxena, Nowduri Aannapurna (Author)

This work is licensed under a Creative Commons Attribution 4.0 International License.
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Abstract
Humic acid has been the catalyst in a novel process that effectively and environmentally acylates amine, phenol, and thiol derivatives. This method works well with aliphatic, aromatic, and heteroaromatic substrates, among other functionalized molecules. There is only one step involved in the simple method, which yields a high yield without any unintended side effects. In addition, the humic acid catalyst may be recycled at least four times, and the process is simpler, quicker, and greener than earlier research. The current work presented aniline (10 mmol, 0.93 mL), acetic anhydride (10 mmol, 1 mL), and humic acid catalyst (15 mg), which were stirred at room temperature for 10 minutes under solvent-free conditions to get a 97% yield.
Highlights
· A development of the protocol under Green methodology.
· Acylation of phenol, amines, alcohol, and thiol derivatives under solvent-free condition.
· Humic acid as a biodegradable catalyst.
· After complete the reaction product was easily isolated from reaction mixture.
· Humic acid is easily recyclable from reaction mixture.
Keywords
- Acetylation,
- Humic acid,
- Solvent-free conditions,
- Green catalyst,
- Pphenol
References
- K. Datta, B. Mitra, B. S. Sharma, Chemistry Select., 7 (2022): e202103602. https://doi.org/10.1002/slct.202103602
- M. Torabi, M. Yarie, M. Zolfigol, Appl. Organomet. Chem., 33 (2019): e4933. https://doi.org/10.1002/aoc.4933
- X. Cao, L. Qiao, H. Zheng, H. Yang, P. Zhang, RSC Adv., 8 (2018): 170. https://doi.org/10.1039/C7RA11259A
- G. Yashwantrao, V. Jejurkar, R. Kshatriya, S. Saha, ACS Sustainable Chem. Eng., 15 (2019): 13551-13558. https://doi.org/10.1021/acssuschemeng.9b03199
- M. Foumeshi, A. Halimehjani, H. Paghandeh, P. Beier, Tetrahedron Lett., 61 (2020): 152270. https://doi.org/10.1016/j.tetlet.2020.152270
- W. Shi, G. Sun, G. Zou, Tetrahedron Lett., 61 (2020): 152140. https://doi.org/10.1016/j.tetlet.2020.152140
- M. Rajca Catalysts, 10 (2020): 249. https://doi.org/10.3390/catal10020249
- B. Mitra, P. Ghosh, Chem. Sel., 6 (2021): 68-81. https://doi.org/10.1002/slct.202004245
- V. Polshettiwar, R. S. Varma, Chem. Soc. Rev., 37 (2008): 1546. https://doi.org/10.1039/B716534J
- P. Anastas, J. Warner Green Chemistry Theory and Practice; Oxford University Press: Oxford, 1998.
- M. T. Reetz, M. Maase, Adv. Mater., 11 (1999): 773. https://doi.org/10.1002/(SICI)1521-4095(199906)11:9%3C773::AID-ADMA773%3E3.0.CO;2-1
- T. W. Green, P. C. M. Wuts, Protective groups in organic synthesis, Wiley, New York, 3rd ed. 1999.
- J. Otera, Esterification: Methods, Reactions, Applications 1st ed, Wiley-VCH, 2003.
- I. Inaloo, Mol. Catal., 492 (2020), 110915. https://doi.org/10.1016/j.mcat.2020.110915
- A. Sardarian, Catal. Let. 148, (2018): 642-652. https://doi.org/10.1007/s10562-017-2277-0
- W. Steglich, G. Hofle, Angew. Chem. Int. Ed., 8 (1969): 981. https://doi.org/10.1002/anie.196909811
- E. Vedejs, T. S. Diver, J. Am. Chem. Soc., 115 (1993): 3358. https://doi.org/10.1021/ja00061a056
- E. F. V. Scriven, Chem. Soc. Rev., 12 (1983): 129. https://doi.org/10.1039/CS9831200129
- S. Tomohumi, Synth. 1 (1999): 1141. https://doi.org/10.1055/s-1999-3521
- A. Orita, C. Tanahashi, A. Kakuda, J. Otera, Angew. Chem. Int. Ed., 39 (2000): 2877. https://doi.org/10.1002/1521-3773(20000818)39:16%3C2877::aid-anie2877%3E3.0.co;2-v
- R. Alleti, M. Perambuduru, S. Samanha, V. P. Reddy, J. Mol. Catal. A Chem., 226 2005: 57. https://doi.org/10.1007/s00706-007-0814-z
- B. Karimi, J. Maleki, J. Org. Chem., 68 (2003): 4951. https://doi.org/10.1021/jo026678+
- N. Ghaffari Khaligh, J. Mol. Catal. A Chem., 90 (2012): 363-364. http://dx.doi.org/10.1016/j.molcata.2012.05.021
- K. Datta, B. Mitra, P. Ghosh Chem. Sel., 8 (2023): e202301255. https://doi.org/10.1002/slct.202301255
- S. Patil, A. Ingale, A. Pise, R. Bhondave Chem. Sel., 7 (2022): e202201590. https://doi.org/10.1002/slct.202201590
- I. Inaloo, M. Esmaeilpour, S. Majnooni, A. Oveisi. Chem. Cat Chem., 12 (2020): 5486-5491. https://doi.org/10.1002/cctc.202000876
- I. Inaloo, S Majnooni, Eur. J. of Org. Chem., 37 (2019): 6359-6368. https://doi.org/10.1002/ejoc.201901140
- A. J. Hajipour, H. Karimi, Chin, J, Catal., 35 (2014): 1982-1989. https://doi.org/10.1002/jccs.201300522
- P. Kumar, R. K. Pandey, M. S. Bodas, S. P. Dagade, M. K. Dogare, A. V. Ramaswamy, J. Mol. Catal. A. Chem., 181 (2002): 207. https://doi.org/10.1016/S1381-1169(01)00365-X
- R. Gupta, A. Gupta, P. Kachru ChemInform., 26 (1995): 1. https://doi.org/10.1002/CHIN.199521065
- J. Albadi, A. Alihosseinzadeh, M. Mardani, Chin. J. Catal., 36 (2015): 308-313. https://doi.org/10.1016/S1872-2067(14)60259-X
- S. Patil, Journal of the Indian Chem. Soc., 101 (2024) 101261. https://doi.org/10.1016/j.jics.2024.101261
- K. Niknam, J. Mol. Catal. A: Chem., 316, (2010): 1. https://doi.org/10.1002/cjoc.201180261
- F. Tamaddon, M. A. Amrollahi, L. Sharafat, Tetrahedron Let., 46, (2005): 46, 7841. https://doi.org/10.1016/j.tetlet.2005.09.005
- H. Veisi, S. Taheri, S. Hemmati, Green Chem., 18, (2016), 18, 6337-6348. https://doi.org/10.1039/C6GC01975G
- N. Tandon, S. Patil, R. Tandon, P. Kumar, RSC Adv., 11 (2021): 29333-29353. https://doi.org/10.1039/D1RA03874E
- N. Tandon, S. Patil, R. Tandon, P. Kumar, RSC Adv., 11 (2021): 21291-21300. https://doi.org/10.1039/D1RA02222A
- S. Patil, R. Tandon, N. Tandon, RSC Adv., 13 (2023): 17051-17061. https://doi.org/10.1039/D3RA01522J
- R. Tandon, Shripad. M. Patil, N. Tandon Lett. Org. Chem., 19 (2022): 616-626. https://doi.org/10.2174/1570178619666220112112901
- S. Patil, R. Tandon, N. Tandon Curr. Res. Green and Sus. Chem., 4 (2021): 100063. https://doi.org/10.1016/j.crgsc.2021.100063
- A. Ingale, S. Patil, S. Shinde Tet. Let. 58 (2017): 4845-4848. https://doi.org/10.1016/j.tetlet.2017.11.032
- S. Patil, R. Tandon, N. Tandon Journal of Physics: Conference series., (2022): 2267, 012107. DOI-10.1088/1742-6596/2267/1/012107
- S. Patil IJPR., 2 (2021): 317. https://doi.org/10.31838/ijpr/2021.13.02.317
- S. Patil, R. Tandon, N. Tandon ACS Omega., 07 (2022): 24190-24201. https://doi.org/10.1021/acsomega.2c01107
- S. Patil, R. Tandon, N. Tandon Pharmaceutical Patent Anal., 11 (2022): 175-186. https://doi.org/10.4155/ppa-2022-0010
- S. Patil, A. Bedre, V. Gade, M. Jopale J. of Chem. Sci., 135 (2023): 50. https://doi.org/10.1007/s12039-023-02172-3
- S. Patil, A. Bedre, V. Gade, M. Jopale, R. Bhagat, A. Pise Synthetic Commun., 53 (2023) 1-11. https://doi.org/10.1080/00397911.2023.2236258
- R. Manjul, T. Gaikwad, V. Gade, B. Rajbhoj, S. Patil, D. Gaikwad, N. Suryawanshi, P. Shinde, D. Suvarna Lett. in Org. Chem. 20 (2023): 967-975. https://doi.org/10.2174/1570178620666230510122033
- A. Pise, A. Ingale, S. Patil Pol. Arom. Comp., 1 (2023): 956 https://doi.org/10.1080/10406638.2023.225956.
- S. Patil, A. Bedre Iran. J of catal., 13 (2023): 235-270. https://doi.org/10.30495/ijc.2023.1991397.2024
- A. Hosseini, M. Halvagar, M. Khalilzadeh, E. Alaee, M. Tajbakhsh Journal of Chemical Res., 1 (2005): 48-49. doi:10.3184/0308234053431202.
- S. Peiman, B. Maleki, & M. Ghani. Sci. Rep., 14 (2024): 21488. https://doi.org/10.1038/s41598-024-72212-6
10.57647/j.ijc.2025.1503.36