Abstract
The application of solid organic waste-originated products in the preparation of synthetically and biologically significant compounds in aqueous media or pure water is a highly desired task in chemical synthesis that shows an effective solution to the circular economy and sustainable environment. In this article, we describe our research on the development of highly economic and sustainable protocols for the synthesis of biologically important oxygen-heterocycles (using a multicomponent reaction) and synthetically important olefins (via the Knoevenagel condensation reaction) using water extract of tamarind seed ash (WETS) as catalyst and aqueous reaction medium. The reactions are carried out at room temperature (RT) under toxic/problematic/volatile organic solvent-free conditions. Products of the current methods have been purified by using recrystallization technique. WETS was characterized from its FTIR, powder XRD, SEM, and EDAX data. Problematic and non-renewable solvents were avoided throughout the process from their synthesis to purification. The utilization of solid organic waste-originated catalyst and aqueous media, avoid of non-renewable substances as catalysts, media, separation solvents and promoters, and unobligating heating conditions can surely attract the attention of chemists towards exploring the waste-based products in chemical transformations.
Graphical abstract
Similar content being viewed by others
Data availability
The melting points, spectroscopic data, and copies of 1H & 13C NMR spectra of the products have been provided in supporting information which can be found at online along with this article.
References
Abdullah HSTSH, Asseri SNARM, Mohamad WNKW, Kan S-Y, Azmi AA, Julius FSY, Chia PW (2021) Green synthesis, characterization and applications of silver nanoparticle mediated by the aqueous extract of red onion peel. Environ Pollut 271:116295
Aljaddua HI, Alhumaimess MS, Hassan HMA (2022) CaO nanoparticles incorporated metal organicframework (NH2-MIL-101) for Knoevenagel condensation reaction. Arabian J Chem 15:103588
Al-Shehri BM, Shabaan MR, Shkir M, Kaushik A, Hamdy MS (2021) Single-step fabrication of Na-TUD-1 novel heterogeneous base nano-catalyst for Knoevenagel condensation reaction. J Nanostruct Chem 11:259–269
Anbu N, Maheswari R, Elamathi V, Varalakshmi P, Dhakshinamoorthy A (2020) Chitosan as a biodegradable heterogeneous catalyst for Knoevenagel condensation between benzaldehydes and cyanoacetamide. Catal Commun 138:105954
Anahmadi H, Fathi M, El Hajri F, Benzekri Z, Sibous S, El Idrissi BC, El Youbi MS, Souizi A, Boukhris S (2022) Synthesis, characterization and application of α-Ca3(PO4)2 as a heterogeneous catalyst for the synthesis of 2,3-diphenylquinoxaline derivatives and Knoevenagel condensation under green conditions. J Mol Struct 1248:131449
Appa RM, Naidu BR, Venkateswarlu D, Hanafiah MM, Lakkaboyana SK, Lakshmidevi J, Venkateswarlu K (2021a) Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes. Green Chem Lett Rev 14:700–712
Appa RM, Raghavendra P, Lakshmidevi J, Naidu BR, Sarma LS, Venkateswarlu K (2021b) Structure controlled Au@Pd NPs/rGO as robust heterogeneous catalyst for Suzuki coupling in biowaste-derived water extract of pomegranate ash. Appl Organomet Chem 35:e6188
Appaturi JN, Pulingam T, Rajabathar JR, Khoerunnisa F, Ling TC, Tan SH, Ng E-P (2021a) Acid-base bifunctional SBA-15 as an active and selective catalyst for synthesis of ethyl α-cyanocinnamate via Knoevenagel condensation. Micropor Mesopor Mater 320:111091
Appaturi JN, Ratti R, Phoon BL, Batagarawa SM, Din IU, Selvaraj M, Ramalingam RJ (2021b) A review of the recent progress on heterogeneous catalysts for Knoevenagel condensation. Dalton Trans 50:4445–4469
Boominathan M, Nagaraj M, Muthusubramanian S, Krishnakumar RV (2011) Efficient atom economical one-pot multicomponent synthesis of densely functionalized 4H-chromene derivatives. Tetrahedron 67:6057–6064
Borah P, Naidu PS, Majumder S, Bhuyan PJ (2013) An efficient one-pot three-component reaction for the synthesis of novel functionalized pyrano[3,2-c]coumarins catalyzed by Na2CO3 in aqueous medium. RSC Adv 3:20450–20455
Chen H, Fan L, Hu T, Zhang X (2021) 6s-3d {Ba3Zn4}–organic framework as an effective heterogeneous catalyst for chemical fixation of CO2 and Knoevenagel condensation reaction. Inorg Chem 60:3384–3392
Chia PW, Chee PS, Asseri SNARM, Yong FSJ, Kan S-Y (2018) Synthesis of 2-aminobiaryl derivatives promoted by water extract of onion peel ash. Malaysian J Anal Sci 22:742–749
Chia PW, Chee PS, Aziz MH, Radzi SAM, Yong FSJ, Kan S-Y (2019a) Water extract of onion peel ash: an efficient green catalytic system for the synthesis of isoindoline-1,3-dione derivatives. Malaysian J Anal Sci 23:23–30
Chia PW, Chee PS, Mazlan NW, Yong FSJ, Rozaini MZH, Kan S-Y (2020) Acetylation of alcohols and amines catalyzed by onion peel ash under a base- and solvent-free condition. Songklanakarin J Sci Technol 42:602–607
Chia PW, Lim BS, Tan KC, Yong FSJ, Kan S-Y (2019b) Water extract of onion peel for the synthesis of bisindolylmethanes. J King Saud Univ Sci 31:642–647
Choudhary P, Sen A, Kumar A, Dhingra S, Nagaraja CM, Krishnan V (2021) Sulfonic acid functionalized graphitic carbon nitride as solid acid–base bifunctional catalyst for Knoevenagel condensation and multicomponent tandem reactions. Mater Chem Front 5:6265–6278
Chowdhury S, Rakshit A, Acharjee A, Saha B (2021) Future trends in green synthesis. In Inamuddin, Boddula R, Ahamed MI, Khan A (eds) Advances in Green Synthesis. Advances in Science, Technology & Innovation (IEREK Interdisciplinary Series for Sustainable Development). Springer, Cham. pp. 41–74
da Silva JF, da Silva FD, Cardoso D (2021) Improved accessibility of Na-LTA zeolite catalytic sites for the Knoevenagel condensation reaction. Micropor Mesopor Mater 331:111640
Das A, Anbu N, Gogoi C, Dhakshinamoorthy A, Biswas S (2020) Amino group functionalized Hf-based metal-organic framework for Knoevenagel-Doebner condensation. Eur J Org Chem 2021:3396–3403
Dewan M, Dutta K, Rana D, Basu D, Basu A, Bhattacharya A, Adhikary A, Chattopadyay D (2020) Effect of tamarind seed polysaccharide on thermogelation property and drug release profile of poloxamer 407-based ophthalmic formulation. New J Chem 44:15708–15715
Erichsen MN, Huynh THV, Abrahamsen B, Bastlund JF, Bundgaard C, Monrad O, Bekker-Jensen A, Nielsen CW, Frydenvang K, Jensen AA, Bunch L (2010) Structure-Activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101). J Med Chem 53:7180–7191
Fan M, Wu H, Shi M, Zhanf P, Jiang P (2019) Well-dispersive K2O–KCl alkaline catalyst derived from waste banana peel for biodiesel synthesis. Green Energy Environ 4:322–327
Gao M-L, Qi M-H, Han Z-B (2019) An exceptionally stable core–shell MOF/COF bifunctional catalyst for a highly efficient cascade deacetalization–Knoevenagel condensation reaction. Chem Commun 55:6377–6380
Gohain M, Laskar K, Phukon H, Bora U, Kalita D, Deka D (2020) Towards sustainable biodiesel and chemical production: multifunctional use of heterogeneous catalyst from littered Tectona grandis leaves. Waste Manag 102:212–221
Halder B, Maity HS, Banerjee F, Kachave AB, Nag A (2021) Water extract of Tamarindus indica seed ash: an agro-waste green medium for one-pot trhee-component approach for the synthesis of 4H-pyran derivatives. Polycycl Aromat Compd. https://doi.org/10.1080/10406638.2020.1858885
Hartmann P, Bender CL, Sann J, Dürr AK, Jansen M, Janek J, Adelhelm P (2013) A comprehensive study on the cell chemistry of the sodium superoxide (Na2O) battery. Phys Chem Chem Phys 15:11661–11672
Heravi MM, Janati F, Zadsirjan V (2020) Applications of Knoevenagel condensation reaction in the total synthesis of natural products. Monatsh Chem 151:439–482
Karimkhah F, Elhamifar D, Shaker M (2021) Ag2CO3 containing magnetic nanocomposite as a powerful and recoverable catalyst for Knoevenagel condensation. Sci Rep 11:18736
Kaur R, Naaz F, Sharma S, Mehndiratta S, Gupta MK, Bedi PMS, Nepali K (2015) Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies. Med Chem Res 24:3334–3349
Kawano A, Moteki T, Ogura M (2020) Effect of delamination on active base site formation over nitrided MWW-type zeolite for Knoevenagel condensation. Micropor Mesopor Mater 299:110104
Kazemi B, Javanshir S, Maleki A, Safari M, Khavasi HR (2012) An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions. Tetrahedron Lett 53:6977–6981
Kemnitzer W, Drewe J, Jiang S, Zhang H, Crogan-Grundy C, Labreque D, Bubenick M, Attardo G, Denis R, Lamothe S, Gourdeau H, Tseng B, Kasibhatla S, Cai SX (2008) Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high throughput screening assay. 4. Structure–activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions. J Med Chem 51:417–423
Kumar CS, Bhattacharya S (2008) Tamarind seed: properties, processing and utilization. Crit Rev Food Sci Nutr 48:1–20
Kumbhar V, Pandey A, Varghese A, Wanjari S (2020) An overview of production, properties and prospects of tamarind seed oil biodiesel as an engine fuel. Int J Ambient Energy. https://doi.org/10.1080/01430750.2020.1824946
Lakshmidevi J, Appa RM, Naidu BR, Prasad SS, Sarma LS, Venkateswarlu K (2018) WEPA: a bio-derived medium for added base, π-acid and ligand free Ullmann coupling of aryl halides using Pd(OAc)2. Chem Commun 54:12333–12336
Lakshmidevi J, Naidu BR, Reddy SSS, Venkateswarlu K (2022) Oxidative iododeborylation reaction of (hetero)arylboronic acids in water extract of pomegranate ash: a novel and sustainable synthesis of iodo(hetero)arenes. Waste Biomass Valor 13:2207–2216
Lakshmidevi J, Vakati V, Naidu BR, Raghavender M, Rao KSVK, Venkateswarlu K (2021) Pd(5%)-KIT-6, Pd(5%)-SBA-15 and Pd(5%)-SBA-16 catalysts in water extract of pomegranate ash: A case study in heterogenization of Suzuki-Miyaura reaction under external base and ligand free conditions. Sustain Chem Parm 19:100371
Li JR, Chen C, Hu YL (2020) Novel and efficient Knoevenagel condensation over mesoporous SBA-15 supported acetate-functionalized basic ionic liquid catalyst. ChemistrySelect 5:14578–14582
Markad D, Khullar S, Kandal SK (2018) Engineering a nanoscale primary amide-functionalized 2D coordination polymer as an efficient and recyclable heterogeneous catalyst for the Knoevenagel condensation reaction. ACS Appl Nano Mater 1:5226–5236
Murugan M, Subramanian E (2006) Studies on defluoridation of water by Tamarind seed, an unconventional biosorbent. J Water Health 4:453–461
Naidu BR, Lakshmidevi J, Naik BSS, Venkateswarlu K (2021) Water extract of pomegranate ash as waste-originated biorenewable catalyst for the novel synthesis of chiral tert-butanesulfinyl aldimines in water. Mol Catal 511:111719
Ng E-P, Ahmad NH, Ling TC, Khoerunnisa F, Daou TJ (2021) Offretite zeolite templated by amphiphile and its catalytic performance in microwave-assisted Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate. Mater Chem Phys 272:125001
Nikoorazm M, Khanmoradi M, Mohammadi M (2020) Guanine-La complex supported onto SBA-15: a novel efficient heterogeneous mesoporous nanocatalyst for one-pot, multi-component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions. Appl Organomet Chem 34:e5504
Oladipo B, Ojumu TV, Latinwo LM, Betiku E (2020) Pawpaw (Carica papaya) peel waste as a novel green heterogeneous catalyst for moringa oil methyl esters synthesis: process optimization and kinetic study. Energies 13:5834
Pandit AP, Koyate KR, Kedar AS, Mute VM (2019) Spongy wound dressing of pectin/carboxymethyl tamarind seed polysaccharide loaded with moxifloxacin beads for effective wound heal. Int J Biol Macromol 140:1106–1115
Pradhan K, Paul S, Das AR (2014) Magnetically retrievable nano crystalline CuFe2O4 catalyzed multi-component reaction: a facile and efficient synthesis of functionalized dihydropyrano[2,3-c]pyrazole, pyrano[3,2-c]coumarin and 4H-chromene derivatives in aqueous media. Catal Sci Technol 4:822–831
Rajendran M, Ramanathan R, Ganesan P, Shanmugavel R (2021) Experimental analysis of tamarind seed powder-based flash powder composition for eco-friendly firecrackers. J Therm Anal Calorim 143:3009–3021
Rajendran M, Shanmugavel R, Ramanathan R, Mahendraprabhu K (2019) Study on noise level reduction in tamarind seed powder based fire cracker. AIP Conf Proc 2128:050021
Raju TD, Reji AK, Raheem N, Sasikumar S (2018) Role of moringa oleifera and tamarind seeds in water treatment. Int J Eng Res Technol 7:454–462
Samanta S, Chowdhury S, DasSharma D, Halder G (2020) The biosorptive uptake of enrofloxacin from synthetically produced contaminated water by tamarind seed derived activated carbon. RSC Adv 10:1204–1218
Sampathkumar L, Selvin PC, Selvasekarapandian S, Perumal P, Chitra R, Muthukrishnan M (2019) Synthesis and characterization of biopolymer electrolyte based on tamarind seed polysaccharide, lithium perchlorate and ethylene carbonate for electrochemical applications. Ionics 25:1067–1082
Schmitt F, Gold M, Rothemund M, Andronache I, Biersack B, Schobert R, Mueller T (2019) New naphthopyran analogues of LY290181 as potential tumor vascular-disrupting agents. Eur J Med Chem 163:160–168
Shen Y, Yuan C, Zhu X, Chen Q, Lu S, Xie H (2021) Engineering cellulose into water soluble poly(protic ionic liquid) electrolytes in the DBU/CO2/DMSO solvent system as an organocatalyst for the Knoevenagel condensation reaction. Green Chem 23:9922–9934
Sundaram MS, Hemshekhar M, Santosh MS, Paul M, Sunitha K, Thushara RM, NaveenKumar SK, Naveen S, Devaraja S, Rangappa KS, Kemparaju K, Girish KS (2015) Tamarind seed (Tamarindus indica) extract ameliorates adjuvant-induced arthritis via regulating the mediators of cartilage/bone degeneration, inflammation and oxidative stress. Sci Rep 5:11117
Tan VA, Quynh LTN, Vo T-TT, Nguyen PA, Don TN, Vasseghian Y, Phan H, Lee S-W (2022) Experimental and computational investigation of a green Knoevenagel condensation catalyzed by zeolitic imidazolate framework-8. Environ Res 204:112364
Vallapudi DR, Makineni HK, Pisipaty SK, Venu H (2018) Combined impact of EGR and injection pressure in performance improvement and NOx control of a DI diesel engine powered with tamarind seed biodiesel blend. Environ Sci Pollut Res 25:36381–36393
van Beurden K, de Koning S, Molendijk D, van Schijndel J (2020) The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds. Green Chem Lett Rev 13:349–364
Venkateswarlu K (2021) Ashes from organic waste as reagents in synthetic chemistry: a review. Environ Chem Let 19:3887–3950
Vidhya E, Vijayakumar S, Nilavukkarasi M, Punitha VN, Snega S, Praseetha PK (2021) Green fabricated MgO nanoparticles as antimicrobial agent: characterization and evaluation. Mater Today Proceed 45:5579–5583
Yap YH, Azmi AA, Mohd NK, Yong FSJ, Kan S-Y, Thirmizir MZA, Chia PW (2020) Green synthesis of silver nanoparticle using water extract of onion peel and application in the acetylation reaction. Arab J Sci Eng 45:4797–4807
Yuan X, Wang J, Wan Z, Zhang Q, Luo J (2021) One-pot Suzuki coupling-Knoevenagel condensation tandem reaction catalyzed by a recyclable magnetic bifunctional catalyst. ChemistrySelect 6:1238–1243
Zhang X, He X, Zhao S (2021a) Preparation of a novel Fe3O4@SiO2@propyl@DBU magnetic core–shell nanocatalyst for Knoevenagel reaction in aqueous medium. Green Chem Lett Rev 14:85–98
Zhang X, Wang L, Xie F, Yaseen A, Chen B, Zhang G-l, Wang M-k, Shen X-f, Li F (2021b) A polysaccharide TKP-2-1 from Tamarindus indica L: purification, structural characterization and immunomodulating activity. J Funct Foods 78:104384
Zhang Z, Wang C, Ma L, Jiang X, Wu C, Wang Y, Jiang Y, Zheng W, Yang Y, Ma Y, Yang J (2019) Molecular mechanism of crolibulin in complex with tubulin provides a rationale for drug design. Biochem Biophy Res Commun 511:381–386
Acknowledgements
BRN thanks Council of Scientific and Industrial Research (CSIR), New Delhi, for fellowship (No. 09/1076(0003)/2018-EMR-I) and JL thanks Science and Engineering Research Board (SERB), New Delhi, for INSPIRE Fellowship (ID: IF150772).
Funding
Authors received financial support from the Science and Engineering Research Board (SERB), New Delhi, via the Grant No. SB/FT/CS-009/2014.
Author information
Authors and Affiliations
Contributions
KVL and SKL designed and KVL supervised the research present in this article. BRN and JL conducted the experiments. All the authors are analyzed the data, drafted, edited and approved the manuscript.
Corresponding author
Ethics declarations
Ethics approval
This manuscript does not contain the studies with human participants or animals performed by any of the others.
Consent of participate
Not applicable.
Consent for publication
Not applicable.
Conflict of interest
The authors declare no competing interests.
Additional information
Responsible Editor: Philippe Garrigues
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
ESM 1
(DOCX 328 kb)
Rights and permissions
About this article
Cite this article
Naidu, B.R., Lakshmidevi, J., Venkateswarlu, K. et al. Highly economic and waste valorization strategy for multicomponent and Knoevenagel reactions using water extract of tamarind seed ash. Environ Sci Pollut Res 30, 71420–71429 (2023). https://doi.org/10.1007/s11356-022-20124-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11356-022-20124-1