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Current Pharmaceutical Design

Editor-in-Chief

ISSN (Print): 1381-6128
ISSN (Online): 1873-4286

Review Article

Removal and Extraction of Carboxylic Acids and Non-ionic Compounds with Simple Hydroxides and Layered Double Hydroxides

Author(s): Luis E.G. Rodriguez, Alesandro Bail, Rodolfo O. Castillo and Gregorio G.C. Arízaga*

Volume 26, Issue 6, 2020

Page: [650 - 663] Pages: 14

DOI: 10.2174/1381612826666191226103623

Price: $65

Abstract

Carboxylic acids are an important natural component as a final product or intermediates for syntheses. They are produced in plants, animals and also as products from biotechnological processes. This review presents the use of single hydroxide particles and layered double hydroxides as alternative adsorbents to remove carboxylic acids from liquid media. The proposal to use hydroxide particles is based on its affinity to adsorb or intercalate carboxylic acids. Besides, the change in properties of the adsorbate-sorbate product evinces that this intermediate can be used as a vehicle to transport and release carboxylic acids. Additional examples will also be presented to prove that layered hydroxides are capable of removing non-ionic compounds from wine, milk and tomato. The use of layered compounds to remove active ingredients could reduce the number of separations steps, costs and reduce or eliminate solvents, thus encouraging the design of industrial processes of separation using hydroxides particles.

Keywords: Hydroxides, layered double hydroxide, removal, adsorption, carboxylic, composite.

[1]
Dertmont O’Hare. Inorganic intercalation compounds. Inorg Mater, Second. Bruce DW, O’Hare D, Eds. England: John Wiley and Sons 1997; 171-254.Avaialable. http://books.google.com.mx/ books?id=s0o6UG7MZQkC&printsec=frontcover&hl=es&source=gbs_ge_summary_r&cad=0#v=onepage&q&f=false
[2]
Wypych F, Arizaga GGC. Intercalation and functionalization of brucite with carboxylic acids. Quim Nova 2005; 28: 24-9.
[http://dx.doi.org/10.1590/S0100-40422005000100005]
[3]
Guerra Rodríguez LE, Ventura Muñoz MG, Carbajal Arízaga GG, Rosello Matas C, González Suérez E. Nanopartículas de hidróxido de aluminio con estructura de Bayerita en un proceso de producción de ácido cítrico, Rev. Cent Azúcar 2018; 45: 68-75.
[4]
Guerra Rodríguez LE, Ventura Munoz M, Gonzalez Suarez E, Rosello Matas C, Carbajal-Arizaga GG. Citric acid removal from aqueous solution with layered aluminum hydroxide crystals. Iran J Chem Chem Eng 2018; 37: 153-61.
[5]
Mills SJ, Christy AG, Génin J-MR, Kameda T, Colombo F. Nomenclature of the hydrotalcite supergroup: natural layered double hydroxides. Mineral Mag 2012; 76: 1289-336.
[http://dx.doi.org/10.1180/minmag.2012.076.5.10]
[6]
Duan X, Evans DG. Layered Double Hydroxides. 1st ed. Heidelberg: Springer-Verlag 2006.
[http://dx.doi.org/10.1007/b100426]
[7]
Benício LPF. Eulálio D, L. de MGuimarães . F.G. Pinto, L.M. da Costa, J. Tronto. Layered double hydroxides as hosting matrices for storage and slow release of phosphate analyzed by stirred-flow method. Mater Res 2018; 21(6) e20171004
[http://dx.doi.org/10.1590/1980-5373-mr-2017-1004]
[8]
Sasai R, Sato H, Sugata M, et al. Why do carbonate anions have extremely high stability in the interlayer space of layered double hydroxides? Case study of layered double hydroxide consisting of Mg and Al (Mg/Al = 2). Inorg Chem 2019; 58(16): 10928-35.
[http://dx.doi.org/10.1021/acs.inorgchem.9b01365] [PMID: 31393726]
[9]
Carlino S. The intercalation of carboxylic acids into layered double hydroxides: a critical evaluation and review of the different methods. Solid State Ion 1997; 98: 73-84.
[http://dx.doi.org/10.1016/S0167-2738(96)00619-4]
[10]
Cortés Ortega JA, Carbajal Arizaga GG. Dosificación de NaOH mediante hidrogeles para regular el tamaño de partículas de hidróxidos dobles laminares In: Av En Quim. 2019; pp. 67-71.
[11]
Lalikoglu M, Gök A, Gök MK, Aşçi YS. Investigation of lactic acid separation by layered double hydroxide: equilibrium, kinetics, and thermodynamics. J Chem Eng Data 2015; 60: 3159-65.
[http://dx.doi.org/10.1021/acs.jced.5b00324]
[12]
Zhang S, Wang Q, Puthiaraj P, Ahn W-S. Ahn. MgFeAl layered double hydroxide prepared from recycled industrial solid wastes for CO2 fixation by cycloaddition to epoxides. J CO2 Util 2019; 34(2019): 395-403.
[http://dx.doi.org/10.1016/j.jcou.2019.07.035]
[13]
Henrist C, Mathieu J-P, Vogels C, Rulmont A, Cloots R. Morphological study of magnesium hydroxide nanoparticles precipitated in dilute aqueous solution. J Cryst Growth 2003; 249: 321-30.
[http://dx.doi.org/10.1016/S0022-0248(02)02068-7]
[14]
Leont’eva NN, Cherepanova SV, Drozdov VA. Thermal decomposition of layered double hydroxides Mg-Al, Ni-Al, Mg-Ga: Structural features of hydroxide, dehydrated, and oxide phases. J Struct Chem 2014; 55: 1326-41.
[http://dx.doi.org/10.1134/S0022476614070142]
[15]
Shamim M, Dana K. Thermal decomposition of layered double hydroxides: Kinetic modeling and validation. Thermochim Acta 2016; 632: 64-71.
[http://dx.doi.org/10.1016/j.tca.2016.03.029]
[16]
Zhao Y, Xiao F, Jiao Q. Hydrothermal synthesis of Ni/Al layered double hydroxide nanorods. J Nanotechnol 2011; 2011: 1-6.
[http://dx.doi.org/10.1155/2011/646409]
[17]
Liang H, Meng F, Cabán-Acevedo M, et al. Hydrothermal continuous flow synthesis and exfoliation of NiCo layered double hydroxide nanosheets for enhanced oxygen evolution catalysis. Nano Lett 2015; 15(2): 1421-7.
[http://dx.doi.org/10.1021/nl504872s] [PMID: 25633476]
[18]
Mardani HR. (Cu/Ni)-Al layered double hydroxides@Fe3O4 as efficient magnetic nanocomposite photocatalyst for visible-light degradation of methylene blue. Res Chem Intermed 2017; 43: 5795-810.
[http://dx.doi.org/10.1007/s11164-017-2963-y]
[19]
From the Sugar Platform to biofuels and biochemicals. Final report for the European Commission 2015.
[20]
De Corato U, De Bari I, Viola E, Pugliese M. Assessing the main opportunities of integrated biorefining from agro-bioenergy co/by-products and agroindustrial residues into high-value added products associated to some emerging markets: A review. Renew Sustain Energy Rev 2018; 88: 326-46.
[http://dx.doi.org/10.1016/j.rser.2018.02.041]
[21]
Eş I, Mousavi Khaneghah A, Barba FJ, Saraiva JA, Sant’Ana AS, Hashemi SMB. Recent advancements in lactic acid production - a review. Food Res Int 2018; 107: 763-70.
[http://dx.doi.org/10.1016/j.foodres.2018.01.001] [PMID: 29580545]
[22]
Garner FH, Ellis SRM. Extraction of acetic acid from water. Chem Eng Sci 1953; 2: 282-6.
[http://dx.doi.org/10.1016/0009-2509(53)80046-1]
[23]
Schöwe N, Bretz K, Hennig T, Schlüter S, Deerberg G. Succinic acid removal and recovery from aqueous solution using hydrotalcite granules: experiments and modeling. Ind Eng Chem Res 2015; 54: 1123-30.
[http://dx.doi.org/10.1021/ie504306p]
[24]
Kang S, Fu J, Zhang G. From lignocellulosic biomass to levulinic acid: a review on acid-catalyzed hydrolysis. Renew Sustain Energy Rev 2018; 94: 340-62.
[http://dx.doi.org/10.1016/j.rser.2018.06.016]
[25]
Meers JLPME. Ácidos orgánicos y aminoácidos.Kristiansen B, Bu’lock J, EdsBiotecnol. España: Básica, Editorial ACRIBIA 2009; p. 636.
[26]
Kumar N, Goel N. Phenolic acids: natural versatile molecules with promising therapeutic applications. Biotechnol Rep (Amst) 2019; 24e00370
[http://dx.doi.org/10.1016/j.btre.2019.e00370] [PMID: 31516850]
[27]
Kumar S, Babu BV. Separation of carboxylic acids from waste water via reactive extraction (2007); 1-9.http://discovery.bits-pilani.ac.in/discip%0Aline/chemical/BVb/
[28]
Aghazadeh M, Ladisch MR, Engelberth AS. Acetic acid removal from corn stover hydrolysate using ethyl acetate and the impact on Saccharomyces cerevisiae bioethanol fermentation. Biotechnol Prog 2016; 32(4): 929-37.
[http://dx.doi.org/10.1002/btpr.2282] [PMID: 27090191]
[29]
Wasewar KL. Reactive extraction: an intensifying approach for carboxylic acid separation. Int J Chem Eng Appl 2012; 249-55.
[http://dx.doi.org/10.7763/IJCEA.2012.V3.195]
[30]
Sajid M, Basheer C. Layered double hydroxides: emerging sorbent materials for analytical extractions. TrAC Trends Analyt Chem 2016; 75: 174-82.
[http://dx.doi.org/10.1016/j.trac.2015.06.010]
[31]
Skwarek E, Janusz W, Sternik D. Adsorption of citrate ions on hydroxyapatite synthetized by various methods. J Radioanal Nucl Chem 2014; 299(3): 2027-36.
[http://dx.doi.org/10.1007/s10967-013-2825-z] [PMID: 26224967]
[32]
Bastianini M, Faffa C, Sisani M, Petracci A. Caffeic acid-layered double hydroxide hybrid: a new raw material for cosmetic applications. Cosmetics 2018; 5: 51.
[http://dx.doi.org/10.3390/cosmetics5030051]
[33]
Wang X-R, Cheng H-M, Gao X-W, Zhou W, Li S-J, Cao X-L, et al. Intercalation assembly of kojic acid into Zn-Ti layered double hydroxide with antibacterial and whitening performances. Chin Chem Lett 2019; 30(4): 919-23.
[http://dx.doi.org/10.1016/j.cclet.2019.03.050]
[34]
Yang M, Gu L, Yang B, et al. Antifouling composites with self-adaptive controlled release based on an active compound intercalated into layered double hydroxides. Appl Surf Sci 2017; 426: 185-93.
[http://dx.doi.org/10.1016/j.apsusc.2017.07.207]
[35]
Pagano C, Perioli L, Latterini L, et al. Folic acid-layered double hydroxides hybrids in skin formulations: technological, photochemical and in vitro cytotoxicity on human keratinocytes and fibroblasts. Appl Clay Sci 2019; 168: 382-95.
[http://dx.doi.org/10.1016/j.clay.2018.12.009]
[36]
Forte MBS, Elias ÉCL, Pastore HO, Filho FM, Rodrigues MI. Evaluation of clavulanic acid adsorption in MgAl-layered double hydroxides: kinetic, equilibrium and thermodynamic studies. Adsorpt Sci Technol 2012; 30: 65-80.
[http://dx.doi.org/10.1260/0263-6174.30.1.65]
[37]
Gondim DR, Cecilia JA, Santos SO, et al. Influence of buffer solutions in the adsorption of human serum proteins onto layered double hydroxide. Int J Biol Macromol 2018; 106: 396-409.
[http://dx.doi.org/10.1016/j.ijbiomac.2017.08.040] [PMID: 28797808 ]
[38]
Barahuie F, Hussein MZ, Gani SA, Fakurazi S, Zainal Z. Synthesis of protocatechuic acid-zinc/aluminium-layered double hydroxide nanocomposite as an anticancer nanodelivery system. J Solid State Chem 2015; 221: 21-31.
[http://dx.doi.org/10.1016/j.jssc.2014.09.001]
[39]
Gasser MS. Inorganic layered double hydroxides as ascorbic acid (vitamin C) delivery system-intercalation and their controlled release properties. Colloids Surf B Biointerfaces 2009; 73(1): 103-9.
[http://dx.doi.org/10.1016/j.colsurfb.2009.05.005] [PMID: 19502014 ]
[40]
Perera J, Weerasekera M, Kottegoda N. Slow release anti-fungal skin formulations based on citric acid intercalated layered double hydroxides nanohybrids. Chem Cent J 2015; 9: 27.
[http://dx.doi.org/10.1186/s13065-015-0106-3] [PMID: 26023319 ]
[41]
Jiang L, Liu J, Zhang C, et al. Synthesis of layered double hydroxides with fermentation liquid of organic waste to extract short-chain fatty acids as a biodenitrification carbon source. ACS Sustain Chem& Eng 2017; 5: 9095-101.
[http://dx.doi.org/10.1021/acssuschemeng.7b02009]
[42]
Martínez Vargas DR, Oviedo MJ, Lisboa S, Hirata GA, Carbajal Arizaga GG. Phosphor dysprosium-doped layered double hydroxides exchanged with different organic functional groups. J Nanomater 2013; 2013: 730153-8.
[http://dx.doi.org/10.1155/2013/730153]
[43]
Cordeiro C, Arizaga G, Ramos L, Wypych F. A new zinc hydroxide nitrate heterogeneous catalyst for the esterification of free fatty acids and the transesterification of vegetable oils. Catal Commun 2008; 9: 2140-3.
[http://dx.doi.org/10.1016/j.catcom.2008.04.015]
[44]
Babaee S, Daneshfar A, Khezeli T. Determination of carboxylic acids in non-alcoholic beer samples by an ultrasonic-assisted dispersive micro-solid phase extraction based on Ni/Cu-Al layered double hydroxide nanocomposites followed by gas chromatography. Ultrason Sonochem 2017; 34: 847-55.
[http://dx.doi.org/10.1016/j.ultsonch.2016.07.023] [PMID: 27773312 ]
[45]
Mak Yu T, Caroline Reis Meira A, Cristina Kreutz J, et al. Exploring the surface reactivity of the magnetic layered double hydroxide lithium-aluminum: An alternative material for sorption and catalytic purposes. Appl Surf Sci 2019; 467-68: 1195-203.
[http://dx.doi.org/10.1016/j.apsusc.2018.10.221]
[46]
Sheng L, Liu J, Zhang C, Zou L, Li YY, Xu ZP. Pretreating anaerobic fermentation liquid with calcium addition to improve short chain fatty acids extraction via in situ synthesis of layered double hydroxides. Bioresour Technol 2019; 271: 190-5.
[http://dx.doi.org/10.1016/j.biortech.2018.09.086] [PMID: 30268014 ]
[47]
Ma X, Ye J, Jiang L, et al. Alkaline fermentation of waste activated sludge with calcium hydroxide to improve short-chain fatty acids production and extraction efficiency via layered double hydroxides. Bioresour Technol 2019; 279: 117-23.
[http://dx.doi.org/10.1016/j.biortech.2019.01.128] [PMID: 30716603 ]
[48]
Perestrelo R, Silva CL, Silva P, Câmara JS. Establishment of the volatile signature of wine-based aromatic vinegars subjected to maceration. Molecules 2018; 23(2): 499.
[http://dx.doi.org/10.3390/molecules23020499] [PMID: 29473913 ]
[49]
Pagano C, Perioli L, Blasi F, Bastianini M, Chiesi C, Cossignani L. Optimisation of phenol extraction from wine using layered double hydroxides and technological evaluation of the bioactive-rich powder. Int J Food Sci Technol 2017; 52: 2582-8.
[http://dx.doi.org/10.1111/ijfs.13544]
[50]
Hernández DE, Magallon AP, Carbajal Arízaga GG. Green extraction of lycopene from tomato juice with layered double hydroxide nanoparticles. Micro & Nano Lett 2019; 14: 230-3.
[http://dx.doi.org/10.1049/mnl.2018.5437]
[51]
Bojórquez RMC, Gallego JG, Collado PS. Propiedades funcionales y beneficios para la salud del licopeno. Nutr Hosp 2013; 28: 6-15.
[http://dx.doi.org/10.3305/nh.2013.28.1.6302]
[52]
Siwach R, Tokas J, Seth R. Use of lycopene as a natural antioxidant in extending the shelf-life of anhydrous cow milk fat. Food Chem 2016; 199: 541-6.
[http://dx.doi.org/10.1016/j.foodchem.2015.12.009] [PMID: 26776006]
[53]
Campos KKD, Araújo GR, Martins TL, et al. The antioxidant and anti-inflammatory properties of lycopene in mice lungs exposed to cigarette smoke. J Nutr Biochem 2017; 48: 9-20.
[http://dx.doi.org/10.1016/j.jnutbio.2017.06.004] [PMID: 28651168]
[54]
Suwanaruang T. Analyzing lycopene content in fruits. Agric Agric Sci Procedia 2016; 11: 46-8.
[http://dx.doi.org/10.1016/j.aaspro.2016.12.008]
[55]
Poojary MM, Passamonti P. Optimization of extraction of high purity all-trans-lycopene from tomato pulp waste. Food Chem 2015; 188: 84-91.
[http://dx.doi.org/10.1016/j.foodchem.2015.04.133] [PMID: 26041168]
[56]
Eh ALS, Teoh SG. Novel modified ultrasonication technique for the extraction of lycopene from tomatoes. Ultrason Sonochem 2012; 19(1): 151-9.
[http://dx.doi.org/10.1016/j.ultsonch.2011.05.019] [PMID: 21715212]
[57]
Poojary MM, Passamonti P. Extraction of lycopene from tomato processing waste: kinetics and modelling. Food Chem 2015; 173: 943-50.
[http://dx.doi.org/10.1016/j.foodchem.2014.10.127] [PMID: 25466110]
[58]
Perez Magallon A. Síntesis de materiales híbridos de hidróxidos dobles laminares con compuestos de interés en nutrición. Universidad de Guadalajara 2019.
[59]
Phiroonsoontorn N, Sansuk S, Santaladchaiyakit Y, Srijaranai S. The use of dissolvable layered double hydroxide components in an in situ solid-phase extraction for chromatographic determination of tetracyclines in water and milk samples. J Chromatogr A 2017; 1519: 38-44.
[http://dx.doi.org/10.1016/j.chroma.2017.09.005] [PMID: 28899552]
[60]
Stählin W, Oswald HR. The crystal structure of zinc hydroxide nitrate, Zn5(OH)8(NO3)2.2H2O. Acta Crystallogr B 1970; 26: 860-3.
[http://dx.doi.org/10.1107/S0567740870003230]
[61]
Meyn M, Beneke K, Lagaly G. Anion-exchange reactions of hydroxy double salts. Inorg Chem 1993; 32: 1209-15.
[http://dx.doi.org/10.1021/ic00059a030]
[62]
Velazquez-Carriles C, Macias-Rodríguez ME, Carbajal-Arizaga GG, Silva-Jara J, Angulo C, Reyes-Becerril M. Immobilizing yeast β-glucan on zinc-layered hydroxide nanoparticle improves innate immune response in fish leukocytes. Fish Shellfish Immunol 2018; 82: 504-13.
[http://dx.doi.org/10.1016/j.fsi.2018.08.055] [PMID: 30170109]
[63]
Nabipour H, Hosaini Sadr M, Thomas N. Synthesis, characterisation and sustained release properties of layered zinc hydroxide intercalated with amoxicillin trihydrate. J Exp Nanosci 2015; 10: 1269-84.
[http://dx.doi.org/10.1080/17458080.2014.998301]
[64]
Hussein MZ, Rahman NS, Sarijo SH, Zainal Z. Herbicide-intercalated zinc layered hydroxide nanohybrid for a dual-guest controlled release formulation. Int J Mol Sci 2012; 13(6): 7328-42.
[http://dx.doi.org/10.3390/ijms13067328] [PMID: 22837696]
[65]
Hussein Al Ali SH, Al-Qubaisi M, Hussein MZ, Zainal Z, Hakim MN, Al-Qubaisi M. Preparation of hippurate-zinc layered hydroxide nanohybrid and its synergistic effect with tamoxifen on HepG2 cell lines. Int J Nanomedicine 2011; 6: 3099-111.
[http://dx.doi.org/10.2147/IJN.S24510] [PMID: 22163163]
[66]
Tagaya H, Sasaki N, Morioka H, Kadokawa J. Preparation of new inorganic-organic layered compounds, hydroxy double salts, and preferential intercalation of organic carboxylic acids into them. Mol Cryst Liq Cryst Sci Technol Sect. A Mol Cryst Liq Cryst 2000; 341: 413-8.
[http://dx.doi.org/10.1080/10587250008026174]
[67]
Ahmat AM, Thiebault T, Guégan R. Phenolic acids interactions with clay minerals: a spotlight on the adsorption mechanisms of gallic acid onto montmorillonite. Appl Clay Sci 2019; 180105188
[http://dx.doi.org/10.1016/j.clay.2019.105188]
[68]
Massaro M, Cavallaro G, Colletti CG, et al. Chemical modification of halloysite nanotubes for controlled loading and release. J Mater Chem B Mater Biol Med 2018; 6: 3415-33.
[http://dx.doi.org/10.1039/C8TB00543E]
[69]
Capello C, Leandro GC, Maduro Campos CE, Hotza D, Mattar Carciofi BA, Valencia GA. Adsorption and desorption of eggplant peel anthocyanins on a synthetic layered silicate. J Food Eng 2019; 262: 162-9.
[http://dx.doi.org/10.1016/j.jfoodeng.2019.06.010]
[70]
Zhao P, Liu X, Tian W, Yan D, Sun X, Lei X. Adsolubilization of 2,4,6-trichlorophenol from aqueous solution by surfactant intercalated ZnAl layered double hydroxides. Chem Eng J 2015; 279: 597-604.
[http://dx.doi.org/10.1016/j.cej.2015.05.037]
[71]
Kohno Y, Asai S, Shibata M, et al. Improved photostability of hydrophobic natural dye incorporated in organo-modified hydrotalcite. J Phys Chem Solids 2014; 75: 945-50.
[http://dx.doi.org/10.1016/j.jpcs.2014.04.010]
[72]
Cursino ACT, Rives V, Carlos LD, Joao R, Wypych F. Layered zinc hydroxide salts intercalated with anionic surfactants and adsolubilized with UV absorbing organic molecules. J Braz Chem Soc 2015; 26: 1769-80.
[http://dx.doi.org/10.5935/0103-5053.20150152]
[73]
Muda Z, Hashim N, Md Isa I, et al. Adsolubilisation of thiacloprid pesticide into the layered zinc hydroxide salt intercalated with dodecyl sulphate, for controlled release formulation. Mater Res Innov 2019; 1-10. In Press
[http://dx.doi.org/10.1080/14328917.2019.1655620]
[74]
Carbajal Arízaga GG, Sánchez Jiménez C, Parra Saavedra KJ, Macías Lamas AM, Puebla Pérez AM. Folate-intercalated layered double hydroxide as a vehicle for cyclophosphamide, a non-ionic anti-cancer drug. Micro & Nano Lett 2016; 11: 360-2.
[http://dx.doi.org/10.1049/mnl.2016.0106]
[75]
Li C, Liang R, Tian R, et al. A targeted agent with intercalation structure for cancer near-infrared imaging and photothermal therapy. RCS Adv 2016; 6: 16608-14.
[http://dx.doi.org/10.1039/C5RA23686J]
[76]
Borges RM, Arizaga GGC, Wypych F. Immobilization of enzymatic extract from Penicillium camemberti with lipoxygenase activity onto a hybrid layered double hydroxide. Biochem Eng J 2009; 48: 93-8.
[http://dx.doi.org/10.1016/j.bej.2009.08.011]
[77]
Nangoi IM, Tavares SR, Wypych F, Leitão AA. Investigation of benzophenone adsolubilized into Zn3Al-LDH intercalated with dodecylsulfate by DFT calculations. Appl Clay Sci 2019; 179105153
[http://dx.doi.org/10.1016/j.clay.2019.105153]
[78]
Hibino T. Anion selectivity of layered double hydroxides: effects of crystallinity and charge density. Eur J Inorg Chem 2018; 2018: 722-30.
[http://dx.doi.org/10.1002/ejic.201701067]

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