Abstract
Tall oil soap as a waste product of the sulphate cellulose production process was treated by single-stage liquid-liquid extraction. The aim of this study was to compare yields of health beneficial matters contained in tall oil soap when several extraction solvents, recommended in literature, were used. Hexane, 1-methyl-4-(1-methylethenyl)-cyclohexene, 2-methylpropan-1-ol, hexan-1-ol, 4-methylpentan-2-one, 2-methoxy-2-methylpropane, and butyl ethanoate were tested. For hydrocarbons it was necessary to add a de-emulsifier into the system, which limits the formation of foams and stable emulsions. The highest yields of total phytosterols (78 %) and especially of β-sitosterol (100 %) were reached when butyl ethanoate was used. However, it was necessary to adjust pH of the treated raw material to approximately 7. The highest yields for feed where pH was not adjusted were obtained with 2-methylpropan-1-ol: 67 % of total sterols and 89 % of β-sitosterol. Disadvantages of most of the tested solvents included the formation of the undesirable solid interphase which could not be removed, partial solubility of the solvents in the water phase, their high boiling point and/or instability. These disadvantages prevent the use of these solvents in industrial applications; they also complicate the treatment of tall oil soap by liquid-liquid extraction or the regeneration of the used organic solvent.
[1] Amundsen, A. L., Ose, L., Nenseter, M. S., & Ntanios, F. Y. (2002). Plant sterol ester-enriched spread lowers plasma total and LDL cholesterol in children with familial hypercholesterolemia. American Journal of Clinical Nutrition, 76, 338–344. 10.1093/ajcn/76.2.338Search in Google Scholar
[2] Auhorn, W. J., & Niemelä, K. (2006). Process chemicals for the production of chemical pulp. Wochenblatt für Papierfabrikation, 134, 1302–1313. (in German) Search in Google Scholar
[3] Awad, A. B., & Fink, C. S. (2000). Phytosterols as anticancer dietary components: Evidence and mechanism of action. Journal of Nutrition, 130, 2127–2130. 10.1093/jn/130.9.2127Search in Google Scholar
[4] Christenson, R. M., & Gloyer, S. W. (1950). U.S. Patent No. 2530809. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[5] Clifton, P. M., Noakes, M., Ross, D., Fassoulakis, A., Cehun, M., & Nestel, P. (2004). High dietary intake of phytosterol esters decreases carotenoids and increases plasma plant sterol levels with no additional cholesterol lowering. Journal of Lipid Research, 45, 1493–1499. DOI: 10.1194/jlr.M400074-JLR200. http://dx.doi.org/10.1194/jlr.M400074-JLR20010.1194/jlr.M400074-JLR200Search in Google Scholar
[6] Demonty, I., Ras, R. T., van der Knaap, H. C. M., Duchateau, G. S. M. J. E., Meijer, L., Zock, P. L., Geleijnse, J. M., & Trautwein, E. A. (2009). Continuous dose-response relationship of the LDL-cholesterol-lowering effect of phytosterol intake. Journal of Nutrition, 139, 271–284. DOI: 10.3945/jn.108.095125. http://dx.doi.org/10.3945/jn.108.09512510.3945/jn.108.095125Search in Google Scholar
[7] Fernandes, P., & Cabral, J. M. S. (2007). Phytosterols: Applications and recovery methods. Bioresource Technology, 98, 2335–2350. DOI: 10.1016/j.biortech.2006.10.006. http://dx.doi.org/10.1016/j.biortech.2006.10.00610.1016/j.biortech.2006.10.006Search in Google Scholar
[8] Fuenzalida Diaz, M. A., Markovits Rojas, A., Leiva Hinojosa, R., & Markovits Schersl, E. (2001). U.S. Patent No. 6297353. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[9] Fuenzalida Diaz, M. A., Markovits Rojas, A., Leiva Hinojosa, R., & Markovits Schersl, E. (1999). European Patent No. EP0952208. Munich, Germany: European Patent Office. Search in Google Scholar
[10] Hamunen, A. (2003). European Patent No. EP1190025. Munich, Germany: European Patent Office. Search in Google Scholar
[11] Hasselstrom, T., & Stoll, M. (1951). U.S. Patent No. 2547208. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[12] Holmbom, B., & Avela, E. (1976). U.S. Patent No. 3965085. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[13] Huibers, D. T. A., Robbins, A. M., & Sullivan, D. H. (2000). U.S. Patent No. 6107456. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[14] Johansson, A. A., Kivikari, R. H. K., & Suokas, E. U. (1977). U.S. Patent No. 4044031. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[15] Jones, P. J. H., Howell, T., MacDougall, D. E., Feng, J. Y., & Parsons, W. (1998). Short-term administration of tall oil phytosterols improves plasma lipid profiles in subjects with different cholesterol levels. Metabolism, 47, 751–756. DOI: 10.1016/S0026-0495(98)90041-5. http://dx.doi.org/10.1016/S0026-0495(98)90041-510.1016/S0026-0495(98)90041-5Search in Google Scholar
[16] Kutney, J. P., Novak, E., & Jones, P. J. (1998). U.S. Patent No. 5770749. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[17] Lin, X., Racette, S. B., Lefevre, M., Spearie, C. A., Most, M., Ma, L., & Ostlund, R. E., Jr. (2010). The effects of phytosterols present in natural food matrices on cholesterol metabolism and LDL-cholesterol: a controlled feeding trial. European Journal of Clinical Nutrition, 64, 1481–1487. DOI: 10.1038/ejcn.2010.180. http://dx.doi.org/10.1038/ejcn.2010.18010.1038/ejcn.2010.180Search in Google Scholar PubMed PubMed Central
[18] Mitchell, D. L., Greebe, F., & Redford, D. A. (1972). Canadian Patent No. CA 901567. Gatineau, Canada: Canadian Intellectual Property Office. Search in Google Scholar
[19] Nijjar, P. S., Burke, F. M., Bloesch, A., & Rader, D. J. (2010). Role of dietary supplements in lowering low-density lipoprotein cholesterol: A review. Journal of Clinical Lipidology, 4, 248–258. DOI: 10.1016/j.jacl.2010.07.001. http://dx.doi.org/10.1016/j.jacl.2010.07.00110.1016/j.jacl.2010.07.001Search in Google Scholar PubMed
[20] Pegel, K. H. (1980). U.S. Patent No. 4188379. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[21] Racette, S. B., Lin, X., Lefevre, M., Spearie, C. A., Most, M. M., Ma, L., & Ostlund, R. E., Jr. (2010). Dose effects of dietary phytosterols on cholesterol metabolism: a controlled feeding study. American Journal of Clinical Nutrition, 91, 32–38. DOI: 10.3945/ajcn.2009.28070. http://dx.doi.org/10.3945/ajcn.2009.2807010.3945/ajcn.2009.28070Search in Google Scholar PubMed PubMed Central
[22] Rousková, M., Heyberger, A., Tříska, J., & Krtička M. (2011). Liquid-liquid extraction of phytosterols and other valuable compounds from tall soap. Chemické listy, 105, 251–255. (in Czech) Search in Google Scholar
[23] Seifert, R., Mostecký, J., Růžiķa, V., & Koudelková, Z. (1988). Czechoslovak Patent No. CS250645. Prague, Czech Republic: Úřad půmyslového vlastnictví. (in Czech) Search in Google Scholar
[24] Steiner, C. S., & Earle, F. (1958). U.S. Patent No. 2835682. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[25] Szykuła, J., Hebda, C., Orpiszewski, J., & Sagańska, K. (1991). Microbial transformation of neutral fraction and upgraded neutral fraction of Polish tall oil. Biotechnology Letters, 13, 917–922. DOI: 10.1007/BF01022099. http://dx.doi.org/10.1007/BF0102209910.1007/BF01022099Search in Google Scholar
[26] Vogel, H. A., & Christenson, R. M. (1950). U.S. Patent No. 2499430. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar
[27] Wong, A., Norman, H. S. O., & MacMillan, A. K. (2003). European Patent No. EP1056767. Munich, Germany: European Patent Office. Search in Google Scholar
© 2011 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Determination of four trace preservatives in street food by ionic liquid-based dispersive liquid-liquid micro-extraction
- Optimisation and validation of liquid chromatographic and partial least-squares-1 methods for simultaneous determination of enalapril maleate and nitrendipine in pharmaceutical preparations
- Chemiluminescence parameters of peroxynitrous acid in the presence of short-chain alcohols and Ru(bpy)32+
- Investigation of multi-layered silicate ceramics using laser ablation optical emission spectrometry, laser ablation inductively coupled plasma mass spectrometry, and electron microprobe analysis
- Simultaneous analysis of three catecholamines by a kinetic procedure: comparison of prediction performance of several different multivariate calibrations
- Enzymatic saccharification of cellulose in aqueous-ionic liquid 1-ethyl-3-methylimidazolium dimethylphosphate-DMSO media
- Statistical and evolutionary optimisation of operating conditions for enhanced production of fungal l-asparaginase
- Extraction of phytosterols from tall oil soap using selected organic solvents
- Dynamic simulations of waste water treatment plant operation
- Influence of recycling and temperature on the swelling ability of paper
- Zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate as an efficient and reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidones under solvent-free conditions
- Toxicity reduction of 2-(5-nitrofuryl)acrylic acid following Fenton reaction treatment
- Synthesis and characterisation of alkaline earth-iron(III) double hydroxides
- Effect of cyclodextrins on pH-induced conformational transition of poly(methacrylic acid)
- Polyamine-substituted epoxy-grafted silica for aqueous metal recovery
- Helical silica nanotubes: Nanofabrication architecture, transfer of helix and chirality to silica nanotubes
- DFT calculations on the Friedel-Crafts benzylation of 1,4-dimethoxybenzene using ZnCl2 impregnated montmorillonite K10 — inversion of relative selectivities and reactivities of aryl halides
- Facile synthesis of 3-aryl-1-((4-aryl-1,2,3-selenadiazol-5-yl)sulfanyl)isoquinolines
- Influence of trimethoxy-substituted positions on fluorescence of heteroaryl chalcone derivatives
- A simple and efficient one-pot synthesis of Hantzsch 1,4-dihydropyridines using silica sulphuric acid as a heterogeneous and reusable catalyst under solvent-free conditions
- Methylprednisolone release from agar-Carbomer-based hydrogel: a promising tool for local drug delivery
- 2-Alkylsulphanyl-4-pyridinecarbothioamides — inhibitors of oxygen evolution in freshwater alga Chlorella vulgaris
Articles in the same Issue
- Determination of four trace preservatives in street food by ionic liquid-based dispersive liquid-liquid micro-extraction
- Optimisation and validation of liquid chromatographic and partial least-squares-1 methods for simultaneous determination of enalapril maleate and nitrendipine in pharmaceutical preparations
- Chemiluminescence parameters of peroxynitrous acid in the presence of short-chain alcohols and Ru(bpy)32+
- Investigation of multi-layered silicate ceramics using laser ablation optical emission spectrometry, laser ablation inductively coupled plasma mass spectrometry, and electron microprobe analysis
- Simultaneous analysis of three catecholamines by a kinetic procedure: comparison of prediction performance of several different multivariate calibrations
- Enzymatic saccharification of cellulose in aqueous-ionic liquid 1-ethyl-3-methylimidazolium dimethylphosphate-DMSO media
- Statistical and evolutionary optimisation of operating conditions for enhanced production of fungal l-asparaginase
- Extraction of phytosterols from tall oil soap using selected organic solvents
- Dynamic simulations of waste water treatment plant operation
- Influence of recycling and temperature on the swelling ability of paper
- Zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate as an efficient and reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidones under solvent-free conditions
- Toxicity reduction of 2-(5-nitrofuryl)acrylic acid following Fenton reaction treatment
- Synthesis and characterisation of alkaline earth-iron(III) double hydroxides
- Effect of cyclodextrins on pH-induced conformational transition of poly(methacrylic acid)
- Polyamine-substituted epoxy-grafted silica for aqueous metal recovery
- Helical silica nanotubes: Nanofabrication architecture, transfer of helix and chirality to silica nanotubes
- DFT calculations on the Friedel-Crafts benzylation of 1,4-dimethoxybenzene using ZnCl2 impregnated montmorillonite K10 — inversion of relative selectivities and reactivities of aryl halides
- Facile synthesis of 3-aryl-1-((4-aryl-1,2,3-selenadiazol-5-yl)sulfanyl)isoquinolines
- Influence of trimethoxy-substituted positions on fluorescence of heteroaryl chalcone derivatives
- A simple and efficient one-pot synthesis of Hantzsch 1,4-dihydropyridines using silica sulphuric acid as a heterogeneous and reusable catalyst under solvent-free conditions
- Methylprednisolone release from agar-Carbomer-based hydrogel: a promising tool for local drug delivery
- 2-Alkylsulphanyl-4-pyridinecarbothioamides — inhibitors of oxygen evolution in freshwater alga Chlorella vulgaris