Abstract
A screening study of the chromatographic separation of Glyceric Acid (GCA) and Tartronic Acid (TTA) was performed using three different polystyrene-divinylbenzene ion-exchange resins in hydrogen form (Dowex® 50WX-8, Dowex® 50WX-4, Dowex® 50WX-2). The experiments were described by the axial dispersion flow model with the LDF approximation incorporated into the software gPROMS. From the three investigated adsorbents differing by the crosslinking, Dowex® 50WX-2 has presented the higher adsorption capacity, as well as the highest bed efficiency expressed by the number of theoretical plates. The adsorption equilibrium constants were determined from single breakthrough experiments, and a very good agreement between experimental and simulated data was achieved for both single components and binary mixtures. Therefore, the fundamental data determined within this work represents a key contribution to the design of continuous chromatographic processes for the purification of GCA and TTA.
Similar content being viewed by others
Abbreviations
- \(C\) :
-
Liquid-phase concentration (kg m−3)
- \({C_0}\) :
-
Feed concentration (kg m−3)
- \({C_{i,o}}\) :
-
Molar concentration of compound i in the bulk phase at the beginning of a breakthrough experiment (mol L−1)
- \({C_{out,i}}\) :
-
Molar concentration of compound i at the fixed bed reactor outlet during a breakthrough experiment mol L−1)
- \({D_{ax}}\) :
-
Axial dispersion coefficient (m2 s−1)
- \({D_{p,i}}\) :
-
Effective diffusivity of compound i (m2 s−1)
- \({D_c}\) :
-
Column diameter (m)
- \(E(t)\) :
-
Residence time distribution (m−1)
- \(EC\) :
-
Eluent consumption (m3 eluent kgProduct −1)
- \(K\) :
-
Linear adsorption equilibrium constant
- \({k_h}\) :
-
Mass transfer coefficient (s−1)
- \(L\) :
-
Fixed bed length (cm)
- \(Pe\) :
-
Peclet number
- \(Prod\) :
-
Productivity (kgProdcut (m3 Adsorbent day)−1)
- \(PUR\) :
-
Raffinate purity
- \(PUX\) :
-
Extract purity
- \(\bar{q}_{i}\) :
-
Average resin-phase concentration (kg m−3)
- \(q_i^*\) :
-
Equilibrium resin retained concentration (kg m−3)
- \(Q\) :
-
Volumetric flow-rate (m3 s−1)
- \({R_p}\) :
-
Radius of the resin particle (m)
- \(t\) :
-
Time variable (s)
- \({t_r}\) :
-
Residence time (s)
- \(T\) :
-
Temperature (K)
- \({V_c}\) :
-
Volume of the column (m3)
- \(u~\) :
-
Interstitial liquid velocity (m s−1)
- \({u_s}\) :
-
Solid velocity (m s−1)
- z:
-
Axial coordinate (m)
- \(\alpha\) :
-
Separation factor
- \(\varepsilon\) :
-
Bed porosity
- \({\gamma _j}\) :
-
Interstitial velocity ratio between the liquid and the solid phases in section j of the TMB
- \(\tau\) :
-
Space time (s)
- \({\sigma ^2}\) :
-
Residence time distribution variance (min2)
References
Accorsi, C.A., Blo, G.: Determination of volatile and non-volatile organic acids in technical sugar solutions by ion-exclusion chromatography. J. Chromatogr. A 555(1), 65–71 (1991). doi:10.1016/S0021-9673(01)87167-3
Binder, T.P.: Simulated moving bed chromatographic purification of amino acids. Archer-Daniels-Midland Company, p. 18 (2008)
Brainer, J.E.N., Sales, D.C.S., Medeiros, E.B.M., Lima Filho, N.M., Abreu, C.A.M.: Wet oxidation of glycerol into fine organic acids: catalyst selection and kinetic evaluation. Braz. J. Chem. Eng. 31(4), 913–923 (2014). doi:10.1590/0104-6632.20140314s00002655
Chambers, T.K., Fritz, J.S.: Effect of polystyrene-divinylbenzene resin sulfonation on solute retention in high-performance liquid chromatography. J. Chromatogr. A. 797(1–2), 139–147 (1998). doi:10.1016/S0021-9673(97)01208-9
Chinnici, F., Spinabelli, U., Riponi, C., Amati, A.: Optimization of the determination of organic acids and sugars in fruit juices by ion-exclusion liquid chromatography. J. Food Compos. Anal. 18(2–3), 121–130 (2005). doi:10.1016/j.jfca.2004.01.005
Ciriminna, R., Pina, C.D., Rossi, M., Pagliaro, M.: Understanding the glycerol market. Eur. J. Lipid Sci. Technol. 116(10), 1432–1439 (2014). doi:10.1002/ejlt.201400229
Dasari, M.A., Kiatsimkul, P.-P., Sutterlin, W.R., Suppes, G.J.: Low-pressure hydrogenolysis of glycerol to propylene glycol. Appl. Catal. A. 281(1–2), 225–231 (2005). doi:10.1016/j.apcata.2004.11.033
Davis, W.R., Tomsho, J., Nikam, S., Cook, E.M., Somand, D., Peliska, J.A.: Inhibition of HIV-1 reverse transcriptase-catalyzed DNA strand transfer reactions by 4-chlorophenylhydrazone of mesoxalic acid. BioChemistry 39(46), 14279–14291 (2000)
Doyon, G., Gaudreau, G., St-Gelais, D., Beaulieu, Y., Randall, C.J.: Simultaneous HPLC determination of organic acids, sugars and alcohols1. Can. Inst. Food Sci. Technol. J. 24(1–2), 87–94 (1991). doi:10.1016/S0315-5463(91)70025-4
Eriksson, C.J.P., Saarenmaa, T.P.S., Bykov, I.L., Heino, P.U.: Acceleration of ethanol and acetaldehyde oxidation by d-glycerate in rats. Metabolism 56(7), 895–898 (2007). doi:10.1016/j.metabol.2007.01.019
Fan, X., Burton, R., Zhou, Y.: Glycerol (byproduct of biodiesel production) as a source for fuels and chemicals: mini review. Open Fuels Energy Sci. J. 3(1), 17–22 (2010). doi:10.2174/1876973X01003010017
Faria, R.P.V., Pereira, C.S.M., Silva, V.M.T.M., Loureiro, J.M., Rodrigues, A.E.: Sorption enhanced reactive process for the synthesis of glycerol ethyl acetal. Chem. Eng. J. 258, 229–239 (2014). doi:10.1016/j.cej.2014.07.073
Fischer, K.: Environmental analysis of aliphatic carboxylic acids by ion-exclusion chromatography. Anal. Chim. Acta 465(1–2), 157–173 (2002). doi:10.1016/S0003-2670(02)00204-0
Fordham, P., Besson, M., Gallezot, P.: Selective catalytic oxidation of glyceric acid to tartronic and hydroxypyruvic acids. Appl. Catal. A. 133(2), L179–L184 (1995). doi:10.1016/0926-860X(95)00254-5
Glueckauf, E., Coates, J.I.: 241. Theory of chromatography. Part IV. The influence of incomplete equilibrium on the front boundary of chromatograms and on the effectiveness of separation. J. Chem. Soc. (1947). doi:10.1039/JR9470001315
Gomes, P.S., Zabkova, M., Zabka, M., Minceva, M., Rodrigues, A.E.: Separation of chiral mixtures in real SMB units: The FlexSMB-LSRE®. AlChE J. 56(1), 125–142 (2010). doi:10.1002/aic.11962
Guiochon, G.: Preparative liquid chromatography. J. Chromatogr. A. 965(1–2), 129–161 (2002). doi:10.1016/s0021-9673(01)01471-6
Habe, H., Shimada, Y., Fukuoka, T., Kitamoto, D., Itagaki, M., Watanabe, K., Yanagishita, H., Sakaki, K.: Two-stage electrodialytic concentration of glyceric acid from fermentation broth. J. Biosci. Bioeng. 110(6), 690–695 (2010). doi:10.1016/j.jbiosc.2010.07.003
Handa, S.S., Sharma, A., Chakraborti, K.K.: Natural products and plants as liver protecting drugs. Fitoterapia 57(5), 307–351 (1986)
Juza, M.: Development of an high-performance liquid chromatographic simulated moving bed separation from an industrial perspective. J. Chromatogr. A. 865(1–2), 35–49 (1999). doi:10.1016/S0021-9673(99)00982-6
Kano, M.R., Bae, Y., Iwata, C., Morishita, Y., Yashiro, M., Oka, M., Fujii, T., Komuro, A., Kiyono, K., Kaminishi, M., Hirakawa, K., Ouchi, Y., Nishiyama, N., Kataoka, K., Miyazono, K.: Improvement of cancer-targeting therapy, using nanocarriers for intractable solid tumors by inhibition of TGF-β signaling. Proc. Natl. Acad. Sci. USA 104(9), 3460–3465 (2007). doi:10.1073/pnas.0611660104
Kerr, B.J., Dozier, W.A. III, Bregendahl, K.: Nutritional value of crude glycerin for nonruminants. In: Proceedings of the 23rd Annual Carolina Swine Nutrition Conference, Raleigh, NC (2007)
Kimura, H.: Oxidation assisted new reaction of glycerol. Polym. Adv. Technol. 12(11–12), 697–710 (2001). doi:10.1002/pat.91
Kimura, H., Tsuto, K.: Catalytic synthesis ofdl-serine and glycine from glycerol. J. Am. Oil Chem. Soc. 70(10), 1027–1030 (1993). doi:10.1007/BF02543031
Lei, W.L.: High inventory weighs on Asia refined glycerine market. (2012). Accessed 05 Oct 2016
Lesova, K., Sturdikova, M., Proksa, B., Pigos, M., Liptaj, T.: OR-1-a mixture of esters of glyceric acid produced by Penicillium funiculosum and its antitrypsin activity. Folia Microbiol. 46(1), 21–23 (2001)
Li, S., Fritz, J.S.: Organic modifiers for the separation of organic acids and bases by liquid chromatography. J. Chromatogr. A. 964(1–2), 91–98 (2002)
Luz, D.A., Rodrigues, A.K.O., Silva, F.R.C., Torres, A.E.B., Cavalcante, C.L. Jr., Brito, E.S., Azevedo, D.C.S: Adsorptive separation of fructose and glucose from an agroindustrial waste of cashew industry. Bioresour. Technol. 99(7), 2455–2465 (2008). doi:10.1016/j.biortech.2007.04.063
McCoy, M.: Glycerin Surplus. Chem. Eng. News Arch. 84(6), 7 (2006). doi:10.1021/cen-v084n006.p007a
McCulloch, B., Goodman, W.H.: Process for purifying phenylalanine. US Patent (1991)
Nesterenko, P.N., Kebets, P.A., Volgin, Y.V.: Use of sulfonated cation-exchange resin based on hypercrosslinked polystyrene for the separation of organic acids. J. Anal. Chem. 56(8), 715–720 (2001). doi:10.1023/a:1016777409132
Nicoud, R.M.: The separation of optical isomers by simulated moving bed chromatography (Part I). Pharm. Technol. Eur. 11(3), 36–44 (1999)
Oil Price Information Service Inc.: Ethanol & Biodiesel Information Service, vol. 13. p. 18. OPIS Publication (2016)
Otero, M., Zabkova, M., Rodrigues, A.E.: Comparative study of the adsorption of phenol and salicylic acid from aqueous solution onto nonionic polymeric resins. Sep. Purif. Technol. 45(2), 86–95 (2005). doi:10.1016/j.seppur.2005.02.011
Pagliaro, M., Ciriminna, R., Kimura, H., Rossi, M., Della Pina, C.: From glycerol to value-added products. Angew. Chem. Int. Ed. Engl. 46(24), 4434–4440 (2007). doi:10.1002/anie.200604694
Pedruzzi, I., Silva, E., Rodrigues, A.: Selection of resins, equilibrium and sorption kinetics of lactobionic acid, fructose, lactose and sorbitol. Sep. Purif. Technol. 63(3), 600–611 (2008). doi:10.1016/j.seppur.2008.07.001
Rodrigues, A.E., Pereira, C., Minceva, M., Pais, L.S., Ribeiro, A.M., Ribeiro, A., Silva, M., Graça, N., Santos, J.C.: Simulated moving bed technology: principles, design and process applications. Simulated moving bed technology. Elsevier, Oxford (2015)
Scharlemann, J.P.W., Laurance, W.F.: How green are biofuels? Science. 319(5859), 43–44 (2008)
Seidel-Morgenstern, A.: Experimental determination of single solute and competitive adsorption isotherms. J. Chromatogr. A. 1037(1–2), 255–272 (2004). doi:10.1016/j.chroma.2003.11.108
Shirao, M., Furuta, R., Suzuki, S., Nakazawa, H., Fujita, S., Maruyama, T.: Sixth international symposium on high performance capillary electrophoresis determination of organic acids in urine by capillary zone electrophoresis. J. Chromatogr. A 680(1), 247–251 (1994). doi:10.1016/0021-9673(94)80074-X
Taylor, J.: OUTLOOK’12: New uses make refined glycerine oleochem leader (2012). Accessed 05 Oct 2016
Thompson, J.C., He, B.B.: Characterization of crude glycerol from biodiesel production from multiple feedstocks. Appl. Eng. Agric. 22(2), 261–265 (2006)
Vente, J.A., Bosch, H., de Haan, A.B., Bussmann, P.J.T: Evaluation of sugar sorption isotherm measurement by frontal analysis under industrial processing conditions. J. Chromatogr. A 1066(1–2), 71–79 (2005). doi:10.1016/j.chroma.2004.12.071
Walser, P.: New ion-exclusion phase for organic acids. J. Chromatogr. A 439(1), 71–81 (1988). doi:10.1016/S0021-9673(01)81676-9
Wilke, C.R., Chang, P.: Correlation of diffusion coefficients in dilute solutions. AlChE J. 1(2), 264–270 (1955). doi:10.1002/aic.690010222
Worz, N., Brandner, A., Claus, P.: Platinum–bismuth-catalyzed oxidation of glycerol: kinetics and the origin of selective deactivation. J. Phys. Chem. C. 114(2), 1164–1172 (2010). doi:10.1021/jp909412h
Acknowledgements
LCDC thanks to the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) for financial support through a PhD Scholarship and to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), which supported this specify work through Sandwich Scholarship at the University of Porto. This work was also financially supported by: Project POCI-01-0145-FEDER-00698 - Associate Laboratory LSRE-LCM funded by FEDER funds through COMPETE2020 - Programa Operacional Competitividade e Internacionalização (POCI) - and by national funds through FCT - Fundação para a Ciência e a Tecnologia.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Coelho, L.C.D., Filho, N.M.L., Faria, R.P.V. et al. Selection of a stationary phase for the chromatographic separation of organic acids obtained from bioglycerol oxidation. Adsorption 23, 627–638 (2017). https://doi.org/10.1007/s10450-017-9882-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10450-017-9882-5