Abstract
A waste feedstock-derived economical basic alternative catalyst is described in this review. Eggshell is one of the household wastes created in tons of weight daily. Therefore, in order to reduce the environmental pollution-related problems, its use in heterogeneous catalysis can be attributed as a great contribution for the chemical and material science society to carry out several known reactions and for the much-needed energy alternative biodiesel production as low-cost catalytic system. Keeping green chemistry in mind, industrial use of these catalysts may also reduce the use of other traditionally used high-cost chemical catalytic systems.
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1 Introduction
1.1 Green Heterogeneous Catalysis and Egg Shell Powder (ESP)
Due to the greater toxicity problem and cost-effectiveness of organic chemicals, it is very necessary to reuse and recycle all the chemicals and catalysts as much as possible for the better and greener future of the environment. Keeping these points in mind, we have to plan our research work in a green manner so that there should be less harmful effects of chemicals on the environment [1]. To undergo a reaction, there should be some kind of catalyst that is responsible for dramatically enhancing the rate of a reaction without altering the thermodynamic equilibrium of a particular reaction [2,3,4,5]. Therefore, the important factor is to adapt the organic transformation with less pollution effects along with a reduction of energy and raw material consumption.
There are two types of catalysts: homogeneous and heterogeneous; however in this review, we will focus on heterogeneous catalysis and we are going to briefly discuss the use of egg shell powder [6,7,8] or calcined egg shell [9, 10]. Homogeneous catalysis are well recognized in synthetic organic chemistry, and have some disadvantages such as difficult separation of the soluble complexes from the reaction mixture, non-recyclability, possibility of breakdown of the complexes, decreasing catalytic activity, etc. [11, 12]. On the other hand, heterogeneous catalysts are easy and simple to recover from the reaction mixture, which furnish the practical importance in both research sectors as well as in the industrial sector, e.g., appropriate in flow reactors [13, 14]. Heterogeneous catalysts are less selective than the homogeneous ones due to the presence of a large number of active sites present on it [15]. In recent years, the development of green heterogeneous catalytic systems has attained great significance for its implication in the chemical processes, which may cause benign environment consequences with high selectivity of the desired molecules, great yield, and lesser amount of side products [16, 17].
With the rapid progress of the industrial sector day by day, there will be a possibility of an energy crisis in near future. Because of this energy crisis, improvements in renewable energies such as wind power, solar energy, and bio-derived solvent extraction have been focused on worldwide [18,19,20]. Therefore, the development of green and ecologically safe energy techniques for a better and sustainable future is always a great initiative with enormous significance [21]. Nowadays, economic and environmental apprehensions encourage researchers and scientists in the application of heterogeneous catalyst to carry out diverse organic transformations, which make the transformation clean, environmentally benign, and with a high product yield [22,23,24]. Thus, heterogeneous catalysis has a great impact on the field of synthetic organic chemistry due to its immense recyclability, reusability, and it attributes all these requirements for the synthetic organic chemistry to overcome the problems faced by the researchers [25,26,27,28,29,30].
1.2 Chemistry of ESP
Egg shell is an important natural calcium feedstock in the form of calcium carbonate along with little percentage of calcium phosphate [31,32,33]. Literature reveals that egg shell contains approximately 95% CaCO3, 2% Ca3(PO4)2, 2% MgCO3 and 1% of organic substances mostly of albuminous character. In egg shell, the content of calcium is 28.2–41.2% and the content of phosphorus is 0.102% [34,35,36]. Due to the basic nature of ESP, [37,38,39] we thought it could be widely used in synthetic organic processes where an external base is necessary for a reaction to proceed. Accordingly, we carried out C–C (Suzuki–Miyaura cross-coupling reactions) and C-hetero atom (peptide coupling, click chemistry) bond formation reactions using ESP as a base alternative as well as solid support (discussed in the later part of this review). SEM-EDAX and TEM-EDAX analysis of the ESP are shown below [40] (Fig. 1):
1.3 Traditionally Used Heterogeneous Catalyst vs. Egg Shell-Based Heterogeneous Catalyst
The principal features for environmentally acceptable processes are based on green heterogeneous catalysts since they are easy to handle and inexpensive in nature.
Literature reports reveal the development of many heterogeneous catalysts to carry out different organic transformations in recent decades. Heterogeneous catalysts are based on impregnation of transition metal on the solid support such as silica [41, 42], clay [43,44,45,46,47,48,49,50,51,52,53], surfactant/clay composites [54, 55], metal exchange clay composite [56, 57], etc.
The use of silica-supported reagents in one-pot multi-component constructions of heterocycles has received considerable importance in organic synthesis since these kinds of catalysts are easy to prepare, inexpensive, and have reusability power due to insolubility in volatile organic compounds (VOCs). Many silica-based reagents such as FeCl3–SiO2 [58], HClO4–SiO2 [59,60,61], Fe3O4@nSiO2–NH2–RhNPs@mSiO2 nanocatalyst [62], Brønsted acids supported on silica [63], TfOH-SiO2 [64] sulfuric acid on nano silica [65], were developed to carry out different organic transformations. These catalysts are very effective and inexpensive along with recyclability power.
Similarly, clay-supported heterogeneous catalysts also find significant applications and the processes using clay-modified catalysts are relatively greener. Since clays are readily available, very cheap, and non-toxic in nature, they have many advantages over other catalysts. A good number of papers are available on the use of Montmorillonite K10 [66,67,68,69,70,71,72,73,74,75,76,77,78], Montmorillonite KSF [79,80,81,82,83,84,85], kaolinite [86,87,88], bentonite [89, 90], etc., as solid supports for the preparation of heterogeneous catalyst.
Some other heterogeneous catalysts were prepared by using zeolite [91,92,93,94,95,96,97], solid acid [98, 99], nano-structured catalyst [100, 101], metal organic framework (MOF) [102,103,104,105,106], chitosan [107,108,109,110,111,112,113,114], hydrotalcite [115,116,117,118,119,120,121,122,123,124,125,126,127], titania [128, 129], alumina [130,131,132,133,134], cellulose [135,136,137,138,139,140,141], carbon/charcoal [142,143,144,145,146,147,148,149,150], polymer and nano-based composite [151, 152], tungstate [153, 154], molecular sieve [155,156,157,158,159], etc., for various organic transformations such as C–H activation [160] and C–C and C–N bond formations [161,162,163].
Comparing egg shell powder with other above-mentioned solid supports, we found that egg shell powder also acts as a solid support with superior selectivity, since calcium carbonate is insoluble in almost all of the organic solvents including water. By using ESP as a solid support, it is easy to recover the catalyst from the reaction mixture and reuse it. Several reports are available in the literature describing the use of egg shell as a solid support for different applications such as in synthesis of hydrogen/syngas, bioactive compound, and in waste-water treatment, etc., but to the best of our knowledge, no reports are available in the literature describing the ESP promoted organic transformations that will be discussed briefly in a later part of this review.
1.4 Importance of Biodiesel and Its Production Through Heterogeneous Catalyst vs. Egg Shell-Modified Catalyst
Due to the limited stock of non-renewable energy sources, researchers have been paying much more attention to energy alternatives since the last decade to meet energy demands. Therefore, to fulfill the increasingly high energy demand in everyday life, the research field has been directed towards the development of alternative and environmental friendly fuel with less pollution effects [164, 165].
Biodiesel, a renewable energy source, is composed of long-chain fatty acid alkyl ester. It has similar physical properties to that of petroleum diesel, with some advantages like being biodegradable, renewable, lower toxicity, and low emission of toxic chemicals. Foremost technique for the synthesis of biodiesel is done by transesterification of vegetable oil or animal fat in the presence of methanol by using low-cost catalysts (Scheme 1) [166,167,168,169]. The usual transesterification reaction for biodiesel production is carried out in the presence of a strong base and it is homogeneous in nature with certain disadvantages like equipment corrosion, formation of unwanted by-products, being hard to separate, difficult to recycle, high temperature, along with certain environment-related problems. Therefore, the development of solid catalysts for biodiesel production always has a great importance and recently gained attention due to their ease of separation, lack of corrosion, and less toxicity problems.
Use of waste material-derived solid catalyst in biodiesel production has a great impact on the environment as well as on the cost-effectiveness of the catalyst. One of these kinds of waste solid catalysts was derived from eggshell, which is a household waste in daily life with a high percentage of calcium components. These kinds of eggshell-derived solid catalyst were used as heterogeneous catalysts for biodiesel production in batch reactors. Various research groups [166,167,168,169,170] derived such low-cost catalysts for biodiesel production, which is discussed in detail in the later part of this review.
Use of eggshell:
- A.
As heterogeneous catalysts in synthetic organic chemistry:
There are two ways through which eggshell can act as a heterogeneous catalyst: (i) through calcinations of the eggshell, and (ii) eggshell without calcinations. It is very hard to compare the efficiency between them since both contain calcium as the major source while the difference is that upon calcinations traces of organic matters are removed from the eggshell. Upon calcination, eggshell, which mainly contains CaCO3, is converted to CaO and it is free from organic content. Therefore, both these catalysts are equally efficient towards different organic transformations and their applications are listed below in detail.
- a.
Use of CaO (from calcined egg shell) as catalyst for organic transformations:
The synthesis of Schiff base is always an important reaction in synthetic organic chemistry by the simple condensation of an aldehyde and an amine. Patil and coworkers [9] synthesized functionalized Schiff bases by using the natural catalyst (calcined egg shell or CES) under solvent-free conditions in which CES acts as a dehydrating agent (Scheme 2).
Similarly, Knoevenagel condensation reaction is another base catalyzed reaction in which condensation of an aldehyde and active methylene compound takes place. CES mainly contains calcium carbonate as the major component, which is basic in nature, and due to this, the condensation of the above compounds takes place. Patil et al. [171] also extended the work on CES, showing its application on the Knoevenagel condensation in aqueous medium as a heterogeneous catalyst as well as a base alternative (Scheme 3).
Khazaei et al. [172] carried out Suzuki–Miyaura cross-coupling reaction in the presence of nano-Fe3O4@SiO2 supported Pd(0), which is a magnetically recoverable nanocatalyst. Here, the silica was synthesized from rice husk and considered as a natural support for the stabilization of magnetic palladium nanoparticles. Due to the combination of palladium source and egg shell, Suzuki–Miyaura reactions easily proceeded giving the desired biaryl moieties in the presence of calcium oxide with the binary mixture of water and ethanol as solvent (1:1) at 85 °C. The synthesized catalyst was well characterized by different spectroscopic analyses such as UV–Vis, FT-IR, X-ray diffraction (XRD), scanning electron microscope (SEM), transmission electron microscope (TEM) and energy-dispersive X-ray spectroscopy (EDX), etc. (Scheme 4).
Waghadhare and coworkers [173] also synthesized a magnetically separable cobalt-iron nano-catalyst based on egg shell as a heterogeneous catalyst as well as a base alternative for Knoevenagel condensation reaction (Scheme 5).
Morbale et al. [174] synthesized 1,4-dihydropyridine and polyhydroquinoline through a green and efficient catalytic system by the simple summarizing of aldehydes, dimedone, or ethylacetoacetate and ammonium acetate using an alternative heterogeneous basic catalyst “modified eggshells” (MES) in a water:ethanol system at 80 °C (Scheme 6).
Riadi et al. [175] also carried out the Knoevenagel reaction in methanol at room temperature using calcined eggshell meal (CEM), which was considered as an alternative green solid support as heterogeneous media since it was easy to separate and reuse. Due to these advantages, egg shell can be considered as a well-established solid support for organic transformations (Scheme 7).
Taleb et al. [176] synthesized oxime derivatives by simple condensation of aldehyde and hydroxylamine hydrochloride by the use of chemically treated eggshell as a heterogeneous catalyst in ethanol at reflux conditions. The catalytic activity of this newly developed heterogeneous catalyst can be used up to seven times (Scheme 8).
Gao et al. [177] synthesized dimethyl carbonate (DMC) using waste eggshell as a heterogeneous catalyst by the treatment of propylene carbonate and methanol at 25 °C and 1 atm pressure. Calcined eggshell was found to be a highly active base, reusable solid heterogeneous catalyst for organic transformations instead of using traditional solid supports, and characterized by using various analytical techniques such as TGA, XRD, nitrogen physisorption, and energy-dispersive X-ray spectroscopy (EDS) (Scheme 9).
- b.
Use of CaCO3 (from uncalcined egg shell) as catalyst for organic transformations:
M. Khazaei et al. [178] developed reusable and efficient Pd nanoparticles using barberry fruit extract through in situ greener reduction method and then supported over eggshell. Here, barberry fruit extract has a dual role of reducing agent as well as stabilizing agent for palladium nanoparticles. These newly developed Pd nanoparticles were applied for ligand-free ipso-hydroxylation of phenylboronic acid and catalytic reduction of different organic dyes, such as 4-nitrophenol, methylene blue, Congo red, and methyl orange by using NaBH4 and aqueous media at room temperature (Scheme 10).
Montilla et al. [179] developed a feasible way to produce lactulose from lactose by employing egg shell as a catalyst (which accelerates the formation of lactulose) through ultra filtrate, which is an alternative for consumption of these industrial wastes. Here, the reaction was stirred and refluxed at 98 °C in glycerol for 60 min using 6 mg/ml of egg shell catalyst loading giving the optimal production of lactulose (Scheme 11).
Youseftabar-Miri et al. [180] carried out the organic transformations for the synthesis of pyrano[3,2-c]quinoline derivatives using eggshell as a heterogeneous catalyst at 60 °C and ethanol as a solvent and described that the eggshell catalyst can be recovered and reused for several times without losing its activity (Scheme 12).
Mallampati et al. [181] also reported a simple method for synthesis of nanoparticle in which metal cations are reduced by eggshell membrane to metal atoms. Eggshell membrane (ESM) stabilized these nanoparticles and acts as a supporting material for the nanoparticles. These newly developed membrane-supported nanoparticles were employed as a heterogeneous catalyst for the nitro reduction and synthesis of propargylamine and these nanoparticles were used for the testing of their catalytic efficiency (Scheme 13).
Our group extended the scope of eggshell heterogeneous catalyst and successfully carried out several reactions such as click or azide-alkyne cycloaddition, peptide coupling reaction, and palladium catalyzed Suzuki–Miyaura reaction using ESP [40, 182, 183]. The role of eggshell in these reactions is a base alternative/reducing agent. Moreover, eggshell is insoluble in water; therefore it also acts as a solid support for these reactions. In case of peptide synthesis, ESP neutralizes the amino acid methyl ester hydrochloride, a coupling partner of the peptide synthesis. Again, in Suzuki–Miyaura reaction, ESP acts as an internal base as well as a solid support for incorporation of in situ-generated palladium nanoparticles. The Pd nanoparticles, stabilized by several components of eggshell powder, were characterized by SEM, SEM-EDAX, TEM, TEM-EDAX, and XRD analysis [40] (Fig. 2 and Scheme 14).
Kuhn et al. [184] developed Pd–Ag/Al2O3 egg-shell catalysts with different Pd/Ag mole ratios and tested for selective hydrogenation of acetylene under tail-end conditions in H2 atmosphere. Here, the total number of Pd surface atoms has been reduced and isolation of large Pd ensembles takes place, and it is confirmed from characterization data (Scheme 15).
Shao et al. [185] have developed a simple and efficient approach in which eggshell Pd/SiO2–Al2O3 catalyst proceeds through CO reduction deposition of PdCl2 at room temperature and aqueous ethanolic solution. Compared to a traditionally used catalyst, this catalytic system has appreciably higher activity in the partial hydrogenation of phenyl acetylene and the formation of ethylbenzene is suppressed due to uniform active metal distribution over the surface of eggshell (Scheme 16).
Wen et al. [186] also worked on selective hydrogenation of pyrolysis gasoline by using eggshell Ni/Al2O3 catalyst in a micro-flow reactor. Here, Wen and coworkers derived this catalyst from LDHs precursor with advanced catalytic hydrogenation efficiency, mainly due to the deposition of Ni metal on Al2O3 as a solid support with stronger interaction between the nickel metal and Al2O3 support (Scheme 17).
Badano et al. [187] developed a supported Pd catalyst over two new polymeric composite materials UTAI (made from triethylene glycol dimethacrylate (TEG), benzoyl peroxide (BPO) and diurethane dimethacrylate (UDMA) and mixed with alumina in monomer ratio of 1:1) and BTAI [made from TEG, BPO and bisphenol A glycerolate dimethacrylate (BGMA) and mixed with alumina in monomer ratio of 1:1] which was found to be extremely active for the selective hydrogenation of styrene stirred in tank reactor at 353 K and H2 pressure in toluene as a solvent. With smaller diffusive restriction of the catalyst than other supported Pd catalysts made the catalyst more efficient for hydrogenation reaction (Scheme 18).
Khajavi et al. [188] developed an eggshell-based Pt-metal organic framework catalyst that can be applied in the selective hydrogenations of olefin mixtures to 1-octene, benzonitrile to benzylamine, and linoleic acid to oleic and stearic acid (Scheme 19).
Gao et al. [189] also developed TiO2-modified porous hollow silica nanoparticles supported Pd-based eggshell nano-catalysts for selective hydrogenation of acetylene. Here, modified TiO2, as support, promotes the selectivity for hydrogenation of acetylene, which showed better performance in the reaction to reduce the temperature and time to 300 °C and 1 h instead of 500 °C and 3 h in TiO2 alone (Scheme 20).
Richter et al. [190] carried out nitric oxide selective catalytic reduction by using novel eggshell MnOx/NaY composite over ammonia, which was operated at temperatures lower than 470 K in water as a solvent giving around 80–100% NO conversion (Scheme 21).
Silva et al. [191] synthesized an efficient and novel Fe–Ni/γ–Al2O3 eggshell catalyst for the decomposition of ammonia to H2 at 650 °C and water as a solvent (Scheme 22). Here, the eggshell catalyst shows superior activity towards ammonia decomposition and can reduce the ammonia trace concentration to equilibrium level.
Yang et al. [192] described wet air oxidation of waste water of coke-plant over eggshell/ruthenium-based catalyst for high chemical oxygen demand (COD) and ammonia/ammonium compounds (NH3–N) exclusion at temperature (250 °C), which is relatively efficient compared to other ruthenium-based catalysts with the same amount of loading. The reason for the high activity of eggshell catalyst towards treatment of waste water of coke-plant can be ascribed to the higher density of active Ru sites in the eggshell layer compared to other uniform catalysts with the same amount of Ru loading (Scheme 23).
Khandelwal et al. [193] developed a method for the synthesis of hydroxyapatite (HA) with the chemical formula Ca10(PO4)6(OH)2, which is the major chemical constituent of human bone tissue (70%). This is the reason why it has been widely engaged in the dental and non-load bearing implantations, to cope up with the bone response as a bioactive material. Here, wet chemical method was employed to synthesize HA powder using eggshells and phosphoric acid (H3PO4). HA powder was characterized by XRD, SEM, EDX FTIR, and TGA-DTA analysis (Scheme 24).
- B.
As heterogeneous catalysts for biodiesel production
Buasri et al. [165] described an eggshell waste-derived catalyst through calcination of eggshell, which converts eggshell calcium carbonate to calcium oxide at 600–900 °C for 4 h. For catalyst testing, it was applied in transesterification of palm oil in the presence of methanol for the synthesis of biodiesel for 1–5 h, at 50–70 °C with 10–30 wt% catalyst loading (Table 1, entry 1).
Wei et al. [166] also described an eggshell-based solid catalyst by calcination of egg shell at 200–1000 °C for 2 h in a muffle furnace under static air. The catalytic activity was confirmed by applying it for the biodiesel synthesis from soybean oil and methanol in a batch reactor under 65 °C and vigorous stirring with 3 wt% of catalyst loading (Table 1, entry 2).
Yin et al. [194] also developed an eggshell catalyst for the biodiesel synthesis from soybean oil deodorizer distillate (SODD). Here, eggshells were calcined in a muffle furnace up to 900 °C to get the CaO particles. This catalyst was then employed for the transesterification of pre-esterified SODD with methanol in varying catalyst loading, time, and temperatures for the synthesis of biodiesel (Table 1, entry 3).
Navajas et al. [195] derived a catalyst based on eggshell that was calcined in a muffle furnace at 900 °C for 2 h. This catalyst was applied in used cooking oil (UCO) in a batch-type reactor along with previously mixed 2% sulfuric acid–methanol solution at 60 °C for 3 h to obtain the desired biodiesel (Table 1, entry 4).
Jazie et al. [196] developed an egg shell eco-friendly catalyst for transesterification of rapeseed oil for the biodiesel production in which eggshell was calcined in a muffle furnace up to a temperature of 1000 °C for 2 h under static air. This eco-friendly catalyst was characterized by XRD, N2 adsorption–desorption, BET surface area, and FTIR analysis. This catalyst was applied for biodiesel production by the treatment of methanol along with rapeseed oil, which was previously heated at 378 K for 1 h in N2-atmosphere to remove water and other volatile organic impurities and cooled (Table 1, entry 5).
Boro et al. [197] synthesized eggshell-derived CaO/Li-doped catalyst which was calcined at 800 °C for 2 h and was used for biodiesel production from nonedible oil feedstock with 94% of conversion with 5% catalyst along and 2% of lithium loading. This derived catalyst was characterized by using XRD, FTIR, and BET surface area analysis. This catalyst was used for esterification of Mesua ferrea Linn (Nahor oil) with concentrated H2SO4 and methanol for 3 h at 60 °C (Table 1, entry 6).
Chen et al. [198] described calcium oxide derived from eggshell and explored the effectiveness of the catalyst for the biodiesel synthesis through transesterification of palm oil. Here, the ostrich eggshells were calcined at 800 °C for 4 h with a heating rate of 10 °C/min. The catalyst was used in the reaction along with palm oil and methanol at 60 °C for 1–3 h with varying amount of ultra power and low amount of catalyst loading (3–10 wt%) (Table 1, entry 7).
Viriya-empikul et al. [199] described a catalyst derived from eggshell CaCO3, which was transformed to CaO by calcinations in the presence of air at 800 °C for 4 h for the biodiesel production from palm olein oil. This catalyst was characterized and confirmed by using XRD, TG/DTA, SEM, EDXRF, N2 adsorption, and BET surface area analysis and applied in palm olein oil and methanol at 60 °C with 10 wt% of catalyst (Table 1, entry 8).
Niju et al. [170, 200,201,202] described biodiesel production using waste egg shells as heterogeneous catalyst derived from eggshell through calcination in a muffle furnace at 900 °C for 2.5 h under static air in order to form active CaO catalyst which was characterized by using XRD, SEM, EDAX, and BET surface area analyzer. Afterwards, this newly developed calcined catalyst was applied in biodiesel synthesis from waste frying oil (WFO) with methanol at 65 °C in a reactive distillation (RD) system. The general method for the production of biodiesel was also employed by using the same catalyst from WFO giving around 95% of conversion with 3 wt% of the catalyst in methanol at 65 °C for 3 h. Similarly, Niju and coworkers also derived highly active CaO catalyst through calcination-hydration-dehydration technique of egg shells. It was used for biodiesel production from WFO with methanol for 1 h at 65 °C (Table 1, entry 9).
2 Conclusions
The use of eggshell, a household waste material, -derived feedstock reduces the probable pollution-related problems and can be used as a better renewable catalyst/product for maximum use of feedstock. Again, the production of biodiesel using eggshell as catalyst/solid support has gained much interest in the field of chemistry and chemical engineering for a better and sustainable future. The industrialization of this kind of waste feedstock for synthesis of the above-mentioned reactions may also get high significance and thus it is expected that eggshell will definitely play an important role in biodiesel production and heterogeneous catalysis in the near future.
References
Mollersten K, Yan J, Westermark M (2003) Energy 28:691–710
Roy I, Gupta MN (2005) Enzyme Microb Technol 36:896–899
Sugihara T, Yamada M, Ban H, Yamaguchi M, Kaneko C (1997) Angew Chem Int Ed Engl 36:2801–2804
Evans MG, Polany M (1936) Trans Faraday Soc 32:1333–1360
Hepburn C (1992) Reaction rates, catalysis and surfactants. Elsevier Science Publishers Ltd, Amsterdam, pp 107–121
Mizuno N, Misono M (1998) Chem Rev 98:199–217
Rodriguez-Reinoso F (1998) Carbon 36:159–175
Hincke MT, Nys Y, Gautron J, Mann K, Rodriguez-Navarro AB, McKee MD (2012) Front Biosci 17:1266–1280
Patil S, Jadhav SD, Shinde SK (2012) Org Chem Int. https://doi.org/10.1155/2012/153159
Tan YH, Abdullah MO, Nolasco-Hipolito C, Taufiq-Yap YH (2015) Appl Energy 160:58–70
Sabbe MK, Reyniers MF, Reuter K (2012) Catal Sci Technol 2:2010–2024
Sheldon RA, Dakka J (1994) Catal Today 19:15–246
Irfan M, Glasnov TN, Kappe CO (2011) Chemsuschem 4:300–316
Hartman RL, McMullen JP, Jensen KF (2011) Angew Chem Int Ed 50:7502–7519
Fache F, Schulz E, Tommasino ML, Lemaire M (2000) Chem Rev 100:2159–2232
Ziolek M (2004) Catal Today 90:145–150
Corma A, Garcia H (2003) Chem Rev 103:4307–4365
Paggiola G, Hunt AJ, McElroy CR, Sherwood J, Clark JH (2014) Green Chem 16:2107–2110
Mohan D, Pittman CU Jr, Steele PH (2006) Energy Fuels 20:848–889
Li Z, Smith KH, Stevens GW (2016) Chin J Chem Eng 24:215–220
Kokel A, Schafer C, Torok B (2017) Green Chem 19:3729–3751
Kim JH, Kim JW, Shokouhimehr M, Lee YS (2005) J Org Chem 70:6714–6720
Hagiwara H, Shimizu Y, Hoshi T, Suzuki T, Ando M, Ohkubo K, Yokoyama C (2001) Tetrahedron Lett 42:4349–4351
Chaminand J, Djakovitch L, Gallezot P, Marion P, Pinel C, Rosier C (2004) Green Chem 6:359–361
Das B, Thirupathi P, Mahender I, Reddy VS, Rao YK (2006) J Mol Catal A Chem 247:233–239
Rezayati S, Erfani Z, Hajinasiri R (2015) Chem Pap 69:536–543
Chtchigrovsky M, Primo A, Gonzalez P, Molvinger K, Robitzer M, Quignard F, Taran F (2009) Angew Chem 121:6030–6034
Baig RBN, Varma RS (2013) Green Chem 15:1839–1843
Lipshutz BH, Taft BR (2006) Angew Chem 118:8415–8418
Hudson R, Li CJ, Moores A (2012) Green Chem 14:622–624
Hirasawa T, Omi N, Ezawa I (2001) J Bone Miner Metab 19:84–88
Ganesh V, Sudhir VS, Kundu T, Chandrasekaran S (2011) Chem Asian J 6:2670–2694
Brun LR, Lupo M, Delorenzi DA, Di Loreto VE, Rigalli A (2013) Int J Food Sci Nutr 64:740–743
Scheideler SE (1998) J Appl Poult Res 7:69–74
Rao TR (1996) Chem Eng Technol 19:373–377
Halikia I, Zoumpoulakis L, Christodoulou E, Prattis D (2001) Eur J Miner Process Environ Prot 1:89–102
Mohamed M, Yusup S, Maitra S (2012) J Eng Sci Technol 7:1–10
Galan I, Glasser FP, Andrade C (2013) J Therm Anal Calorim 111:1197–1202
Rodriguez-Navarro C, Ruiz- Agudo E, Luque A, Rodriguez-Navarro AB, Ortega-Huertas M (2009) Am Mineral 94:578–593
Konwar M, Boruah PR, Saikia PJ, Khupse ND, Sarma D (2017) ChemistrySelect 2:4983–4987
Navalon S, Alvaro M, Garcia H (2010) Appl Catal B 99:1–26
Climent MJ, Corma A, Iborra S (2012) RSC Adv 2:16–58
Laszlo P (1987) Science 235:1473–1477
Laszlo P (1986) Acc Chem Res 19:121–127
Varma RS, Dahiya R, Kumar S (1997) Tetrahedron Lett 38:2039–2042
Chalais S, Cornelis A, Gerstmans A, Kolodziejski W, Laszlo P, Mathy A, Metra P (1985) Helv Chim Acta 68:1196–1203
Nierop KGJ, van Bergen PF (2002) J Anal Appl Pyrolysis 63:197–208
Roudier JF, Foucaud A (1984) Tetrahedron Lett 25:4315–4318
Rittles JA, Chaudhuri AK, Besson SW (1964) J Polym Sci Part A Polym Chem 2:1221–1231
Garrido-Ramírez EG, Theng BKG, Mora ML (2010) Appl Clay Sci 47:182–192
Vaccari A (1999) Appl Clay Sci 14:161–198
Shaikh NS, Deshpande VH, Bedekar AV (2001) Tetrahedron 57:9045–9048
Varma RS (2002) Tetrahedron 58:1235–1255
Varma RS, Pitchumani K, Naicker KP (1999) Green Chem 1:95–97
Varma RS (1999) Green Chem 1:43–55
Jeganathan M, Dhakshinamoorthy A, Pitchumani K (2014) ACS Sustain Chem Eng 2:781–787
Jeganathana M, Pitchumani K (2014) RSC Adv 4:38491–38497
Nasrollahzadeh M, Bayat Y, Habibi D, Moshae S (2009) Tetrahedron Lett 50:4435–4438
Bigdeli MA, Nemati F, Mahdavinia GH (2007) Tetrahedron Lett 48:6801–6804
Chakraborti AK, Gulhane R (2003) Chem Commun 15:1896–1897
Bigdeli MA, Heravi MM, Mahdavini GH (2007) J Mol Catal A Chem 275:25–29
Zhou J, Li Y, Sun HB, Tang Z, Qi L, Liu L, Ai Y, Li S, Shao Z, Liang Q (2017) Green Chem 19:3400–3407
Kaur M, Sharma S, Bedi PMS (2015) Chin J Catal 36:520–549
Wang B, Hu J, Zhang F, Zheng H (2016) Heterocycles 92:103–113
Ghodrati K, Farrokhi A, Karami C, Hamidi Z (2015) Synth React Inorg M 45:15–20
Dintzner MR, Little AJ, Pacilli M, Pileggi DJ, Osner ZR, Lyons TW (2007) Tetrahedron Lett 48:1577–1579
Avalos M, Babiano R, Bravo JL, Cintas P, Jimenez JL, Palacios JC (1998) Tetrahedron Lett 39:9301–9304
Soriente A, Arienzo R, Rosa MD, Palombi L, Spinella A, Scettri A (1999) Green Chem 1:157–162
Borah BJ, Borah SJ, Saikia K, Dutta DK (2014) Appl Catal A 469:350–356
Gajare AS, Shaikh NS, Jnaneshwara GK, Deshpande VH, Ravindranathan T, Bedekar AV (2000) J Chem Soc Perkin Trans 1:999–1001
Gajare AS, Shaikh NS, Bonde BK, Deshpande VH (2000) J Chem Soc Perkin Trans 1:639–640
Saikia PK, Sarmah PP, Borah BJ, Saikia L, Dutta DK (2016) J Mol Catal A Chem 412:27–33
Phukan A, Borah SJ, Bordoloi P, Sharma K, Borah BJ, Sarmah PP, Dutta DK (2017) Adv Powder Technol 28:1585–1592
Choudhary VR, Dumbre DK, Patil SK (2012) RSC Adv 2:7061–7065
Deville JP, Behar V (2001) J Org Chem 66:4097–4098
Bahulayan D, Das SK, Iqbal J (2003) J Org Chem 68:5735–5738
Marvi O, Fekri LZ, Takhti M (2014) Russ J Gen Chem 84:1837–1840
Shanmugam P, Rajasingh P (2002) Chem Lett 31:1212–1213
Yadav JS, Reddy BVS, Eeshwaraiah B, Srinivas M (2004) Tetrahedron 60:1767–1771
Yadav JS, Reddy BVS, Kumar GM, Murthy CVSR (2001) Tetrahedron Lett 42:89–91
Yadav JS, Reddy BVS, Sadasiv K, Reddy PSR (2002) Tetrahedron Lett 43:3853–3856
Dintzner MR, Morse KM, McClelland KM, Coligado DM (2004) Tetrahedron Lett 45:79–81
Yadav JS, Reddy BVS, Satheesh G (2004) Tetrahedron Lett 45:3673–3676
Meshram HM, Sekhar KC, Ganesh YSS, Yadav JS (2000) Synlett 9:1273–1274
Babu M, Pitchumani K, Ramesh P (2013) Helv Chim Acta 96:1269–1272
Bizaia N, de Faria EH, Ricci GP, Calefi PS, Nassar EJ, Castro KADF, Nakagaki S, Ciuffi KJ, Trujillano R, Vicente MA, Gil A, Korili SA (2009) ACS Appl Mater Interfaces 1:2667–2678
Bandgar BP, Kasture SP (2000) Green Chem 2:154–156
Yadav JS, Reddy BVS, Madan C (2001) Synlett 7:1131–1133
Feng J, Hu X, Yue PL (2004) Environ Sci Technol 38:269–275
Yip AC, Lam FL, Hu X (2005) Ind Eng Chem Res 44:7983–7990
Nasrollahzadeh M, Habibi D, Shahkarami Z, Bayat Y (2009) Tetrahedron 65:10715–10719
Smith K, Almeer S, Black SJ (2000) Chem Commun 17:1571–1572
Davis ME (1998) Microporous Mesoporous Mater 21:173–182
Cejka J, Centi G, Pariente JP, Roth WJ (2012) Catal Today 179:2–15
Tajbakhsh M, Heidary M, Hosseinzadeh R (2016) Res Chem Intermed 42:1425–1439
Teimouri A, Chermahini AN (2011) Polyhedron 30:2606–2610
Srivastava R, Srinivas D, Ratnasamy P (2005) Appl. Catal. A 289:128–134
Bokade VV, Yadav GD (2012) Ind Eng Chem Res 51:1209–1217
Tandiary MA, Masui Y, Onaka M (2015) RSC Adv 5:15736–15739
Soni VK, Sharma RK (2016) ChemCatChem 8:1763–1768
Mirsafaei R, Delzendeh S, Abdolazimi A (2016) Int J Environ Sci Technol 13:2219–2226
Alkordi MH, Liu Y, Larsen RW, Eubank JF, Eddaoudi M (2008) J Am Chem Soc 130:12639–12641
Dhakshinamoorthy A, Asiric AM, Garcia H (2015) Chem Soc Rev 44:1922–1947
Wu CD, Hu A, Zhang L, Lin W (2005) J Am Chem Soc 127:8940–8941
Gao S, Zhao N, Shu M, Che S (2010) Appl Catal A 388:196–201
Li Z, Meng F, Zhang J, Xie J, Dai B (2016) Org Biomol Chem 14:10861–10865
Krajewska B (2004) Enzyme Microb Technol 35:126–139
Hardy JJE, Hubert S, Macquarrie DJ, Wilson AJ (2004) Green Chem 6:53–56
Ahmed N, Siddiqui ZN (2015) ACS Sustain Chem Eng 3:1701–1707
Guibal E (2005) Prog Polym Sci 30:71–109
Leonhardt SES, Stolle A, Ondruschka B, Cravotto G, De Leo C, Jandt KD, Keller TF (2010) Appl Catal A 379:30–37
Khalil KD, Al-Matar HM (2013) Molecules 2013(18):5288–5305
Murugadoss A, Chattopadhyay A (2008) Nanotechnology 19(015603):1–9. https://doi.org/10.1088/0957-4484/19/01/015603
Qin Y, Zhao W, Yang L, Zhang X, Cui Y (2012) Chirality 24:640–645
Khan FA, Dash J, Satapathy R, Upadhyay SK (2004) Tetrahedron Lett 45:3055–3058
Zhu H, Zhou M, Zeng Z, Xiao G, Xiao R (2014) Korean J Chem Eng 31:593–597
Ramirez JP, Kapteijn F, Moulijn JA (1999) Catal Lett 60:133–138
Ramani A, Chanda BM, Velu S, Sivasanker S (1999) Green Chem 1:163–165
Choudary BM, Kantam ML, Reddy CV, Rao KK, Figueras F (1999) Green Chem 1:187–189
Nishimura T, Kakiuchi N, Inoue M, Uemura S (2000) Chem Commun 14:1245–1246
Abello S, Medina F, Tichit D, Perez-Ramirez J, Cesteros Y, Salagrea P, Sueiras JE (2005) Chem Commun 11:1453–1455
Debecker DP, Gaigneaux EM, Busca G (2009) Chem Eur J 15:3920–3935
Ebitani K, Motokura K, Mizugaki T, Kaneda K (2005) Angew Chem 117:3489–3492
Sels BF, De Vos DE, Jacobs PA (2001) Cat Rev Sci Eng 43:443–488
Zhoua H, Zhuob GL, Jiang XZ (2006) J Mol Catal A Chem 248:26–31
Kantam ML, Kumar KBS, Raja KP (2006) J Mol Catal A Chem 247:186–188
Gao L, Teng G, Xiao G, Wei R (2010) Biomass Bioenergy 34:1283–1288
Enache DI, Edwards JK, Landon P, Espriu BS, Carley AF, Herzing AA, Watanabe M, Kiely CJ, Knight DW, Hutchings GJ (2006) Science 311:362–365
McTiernan CD, Leblanc X, Scaiano JC (2017) ACS Catal 7:2171–2175
Bujdak J, Rode BM (1997) J Mol Evol 45:457–466
Bujdak J, Rode BM (1999) Origins Life Evol Biosphere 290:451–461
Ernst JB, Muratsugu S, Wang F, Tada M, Glorius F (2016) J Am Chem Soc 138:10718–10721
Gniewek A, Ziolkowski JJ, Trzeciak AM, Zawadzki M, Grabowska H, Wrzyszcz J (2008) J Catal 254:121–130
Pocostales P, Alvarez P, Beltran FJ (2011) Chem Eng J 168:1289–1295
Kumbhar A, Jadhav S, Kamble S, Rashinkar G, Salunkhe R (2013) Tetrahedron Lett 54:1331–1337
Jamwal N, Sodhi RK, Gupta P, Paul S (2011) Int J Biol Macromol 49:930–935
Wanga X, Hua P, Xuea F, Wei Y (2014) Carbohydr Polym 114:476–483
Reddy KR, Kumar NS, Reddy PS, Sreedhar B, Kantam ML (2006) J Mol Catal A Chem 252:12–16
Azambre B, Heintz O, Krzton A, Zawadzki J, Weber JV (2000) J Anal Appl Pyrolysis 55:105–117
Shaabani A, Maleki A (2007) Appl Catal A 331:149–151
Shaabani A, Rahmati A, Badri Z (2008) Catal Commun 9:13–16
Lipshutz BH, Tasler S, Chrisman W, Spliethoff B, Tesche B (2003) J Org Chem 68:1177–1189
Lipshutz BH, Taft BR (2006) Angew Chem 118:8415–8418
Lipshutz BH, Nihan DM, Vinogradova E, Taft BR, Boskovic ZV (2008) Org Lett 10:4279–4282
Maegawa T, Fujiwara Y, Inagaki Y, Esaki H, Monguchi Y, Sajiki H (2008) Angew Chem 120:5474–5477
Sharghi H, Khalifeh R, Doroodmand MM (2009) Adv Synth Catal 351:207–218
Garcia-Suarez EJ, Tristany M, Garcia AB, Colliere V, Philippot K (2012) Microporous Mesoporous Mater 153:155–162
Liao M, Hu Q, Zheng J, Li Y, Zhou H, Zhong CJ, Chen BH (2013) Electrochim Acta 111:504–509
Patil NM, Bhanage BM (2015) Catal Today 247:182–189
Tang W, Li J, Jin X, Sun J, Huang J, Li R (2014) Catal Commun 43:75–78
Wang MS, Pinnavaia TJ (1994) Chem Mater 6:468–474
Razmi H, Abdollahi V, Mohammad-Rezaei R (2016) Environ Chem Lett 14:521–526
Ganga VSR, Choudhary MK, Tak R, Kumari P, Abdi SHR, Kureshy RI, Khan NH (2017) Catal Commun 94:5–8
He J, Li B, Chen F, Xu Z, Yin G (2009) J Mol Catal A Chem 304:135–138
Kumar P, Pandey RK (2000) Green Chem 2:29–32
Dapurkar SE, Sakthivel A, Selvam P (2003) New J Chem 27:1184–1190
Huang J, Jiang T, Gao H, Han B, Liu Z, Wu W, Chang Y, Zhao G (2004) Angew Chem 116:1421–1423
Mehnert CP, Weaver DW, Ying JY (1998) J Am Chem Soc 120:12289–12296
Son YC, Makwana VD, Howell AR, Suib SL (2001) Angew Chem 113:4410–4413
Santoro S, Kozhushkov SI, Ackermann L, Vaccaro L (2016) Green Chem 18:3471–3493
Yin L, Liebscher J (2007) Chem Rev 107:133–173
Chetia M, Ali AA, Bhuyan D, Saikia L, Sarma D (2015) New J Chem 39:5902–5907
Chetia M, Ali AA, Bordoloi A, Sarma D (2017) J Chem Sci 129:1211–1217
Boro J, Deka D, Thakur AJ (2012) Renew Sustain Energy Rev 16:904–910
Buasri A, Chaiyut N, Loryuenyong V, Wongweang C, Khamsrisuk S (2013) Sustain Energy 1:7–13
Wei Z, Xu C, Li B (2009) Bioresour Technol 100:2883–2885
Cho YB, Seo G (2010) Bioresour Technol 101:8515–8519
Jazie AA, Pramanik H, Sinha ASK (2012) Egg Shell Waste-Catalyzed Transesterification of Mustard Oil: Optimization Using Response Surface Methodology (RSM), 2012 2nd International conference on power and energy systems (ICPES 2012) 56, https://doi.org/10.7763/ipcsit.2012.v56.10
Chakraborty R, Bepari S, Banerjee A (2010) Chem Eng J 165:798–805
Niju S, Meera KM, Begum S, Anantharaman N (2014) RSC Adv 4:54109–54114
Patil S, Jadhav SD, Deshmukh MB (2013) J Chem Sci 125:851–857
Khazaei A, Khazaei M, Nasrollahzadeh M (2017) Tetrahedron 73:5624–5633
Waghadhare SS, Naravane VM, Pathare SV (2014) Novel egg shell based magnetically separable nano catalyst for Knoevenagel condensation reaction, Vidnyan Sanshodhan Puraskar Contest, Marathi Vidnyan Parishad
Morbale ST, Shinde SS, Jadhav SD, Deshmukh MB, Patil SS (2015) Der Pharmacia Lettre 7:169–182
Riadi Y, Slimani R, Haboub A, Antri SE, Safi M, Lazar S (2013) Mor J Chem 1:24–28
Taleb MA, Mamouni R, Benomar MA, Bakka A, Mouna A, Taha ML, Benlhachemi A, Bakiz B, Villain S (2017) J Environ Chem Eng 5:1341–1348
Gao Y, Xu C (2012) Catal Today 190:107–111
Khazaei M, Khazaei A, Nasrollahzadeh M, Tahsili MR (2017) Tetrahedron 73:5613–5623
Montilla A, del Castillo MD, Sanz ML, Olano A (2005) Food Chem 90:883–890
Youseftabar-Miri L, Akbari F, Ghraghsahar F (2014) Iran J Catal 4:85–89
Mallampati R, Valiyaveettil S (2014) ACS Sustain Chem Eng 2:855–859
Konwar M, Ali AA, Sarma D (2016) Tetrahedron Lett 57:2283–2285
Konwar M, Ali AA, Chetia M, Saikia PJ, Khupse ND, Sarma D (2016) ChemistrySelect 1:6016–6019
Kuhn M, Lucas M, Claus P (2015) Ind Eng Chem Res 54:6683–6691
Shao Z, Li C, Chen X, Pang M, Wang X, Liang C (2010) ChemCatChem 2:1555–1558
Wen X, Li R, Yang Y, Chen J, Zhang F (2013) Appl Catal A 468:204–215
Badano JM, Betti C, Rintoul I, Berlanga JV, Cagnola E, Torres G, Vera C, Yori J, Quiroga M (2010) Appl Catal A 390:166–174
Khajavi H, Stil HA, Kuipers HPCE, Gascon J, Kapteijn F (2013) ACS Catal 3:2617–2626
Gao J, Zhu Q, Wen L, Chen J (2010) Particuology 8:251–256
Richter M, Trunschke A, Bentrup U, Brzezinka KW, Schreier E, Schneider M, Pohl MM, Fricke R (2002) J Catal 206:98–113
Silva H, Nielsen MG, Fiordaliso EM, Damsgaard CD, Gundlach C, Kasama T, Chorkendorff I, Chakraborty D (2015) Appl Catal A 505:548–556
Yang M, Sun Y, Xu AH, Lu XY, Du HZ, Sun CL, Li C (2007) Bull Environ Contam Toxicol 79:66–70
Khandelwal H, Prakash S (2016) J Miner Mater Charact Eng 4:119–126
Yin X, Duan X, You Q, Dai C, Tan Z, Zhu X (2016) Energy Convers Manage 112:199–207
Navajas A, Issariyakul T, Arzamendi G, Gandia LM, Dalai AK (2013) Asia-Pac J Chem Eng 6:7. https://doi.org/10.1002/apj.1715
Jazie AA, Pramanik H, Sinha ASK, Jazie AA (2013) Int J Sustain Dev Green Econ 2:2315–4721
Boro J, Konwar LJ, Deka D (2014) Fuel Process Technol 122:72–78
Chen G, Shan R, Shi J, Yan B (2014) Bioresour Technol 171:428–432
Viriya-empikul N, Krasae P, Puttasawat B, Yoosuk B, Chollacoop N, Faungnawakij K (2010) Bioresour Technol 101:3765–3767
Niju S, Begum KMMS, Anantharaman N (2014) RSC Adv 4:54109–54114
Niju S, Begum KMMS, Anantharaman N (2014) Environ Prog Sustain Energy 6:1–7. https://doi.org/10.1002/ep.11939
Niju S, Begum KMMS, Anantharaman N (2014) J Saudi Chem Soc 18:702–706
Acknowledgements
MK is thankful to UGC, New Delhi for UGC-BSR fellowship. D.S. is thankful to DST, New Delhi, India, for a research grant (no. EMR/2016/002345). The authors acknowledge the Department of Science and Technology for financial assistance under DST-FIST program and UGC, New Delhi for Special Assistance Programme (UGC-SAP) to the Department of Chemistry, Dibrugarh University.
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Konwar, M., Chetia, M. & Sarma, D. A Low-Cost, Well-Designed Catalytic System Derived from Household Waste “Egg Shell”: Applications in Organic Transformations. Top Curr Chem (Z) 377, 6 (2019). https://doi.org/10.1007/s41061-018-0230-3
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DOI: https://doi.org/10.1007/s41061-018-0230-3