Bioseparation of Nutraceuticals Using Supercritical Carbon Dioxide

Food Engineering Series

Volumn , Issue , 2011, Pages 353-392

  Temelli, Feral ^a   Seifried, Bernhard ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Binary Diffusion Coefficient; Deodorizer Distillate; Fatty Acid Ethyl Ester; Supercritical Carbon Dioxide; Supercritical Fluid

Indexed keywords

EID: 84865467755     PISSN: 15710297     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4419-7475-4_16     Document Type: Chapter

References (186)

1. Ackman RG (1988) Oils and fats group international lecture – the year of the fish oils. Chem Ind 7:139–145
2. Ackman RG, Ke PJ, Jangaard PM (1973) Fractional vacuum distillation of Herring oil methylesters. J Am Oil Chem Soc 50:1–8
3. Ambrogi A, Cardarelli DA, Eggers R (2002) Fractional extraction of paprika using supercritical carbon dioxide and on-line determination of carotenoids. J Food Sci 67:3236–3241
4. Ambrogi A, Cardarelli DA, Eggers R (2003) Separation of natural colorants using a combined high pressure extraction-adsorption process. Lat Am Appl Res 33:323–326
5. Bartle KD, Clifford AA, Jafar SA, Shilstone GF (1991) Solubilities of solids and liquids of low volatility in supercritical carbon-dioxide. J Phys Chem Ref Data 20:713–756
6. Baumann D, Adler S, Gr€uner S, Otto F, Weinreich B, Hamburger M (2004) Supercritical carbon dioxide extraction of marigold at high pressures: Comparison of analytical and pilot-scale extraction. Phytochem Anal 15:226–230
7. 2 extraction of b-carotene and lycopene from tomato paste waste. J Agric Food Chem 48:5507–5511
8. Bernardo-Gil MG, Grenha J, Santos J, Cardoso P (2002) Supercritical fluid extraction and characterisation of oil from hazelnut. Eur J Lipid Sci Technol 104:402–409
9. Blaha-Schnabel A, Beyer A, Czech B, Jakob H, Schiemann H, Weidner E, Peter S (1996) Influence of interfacial tension and viscosity on the behavior of a packed column in near-critical fluid extraction. Chem Eng Commun 146:13–31
10. Breivik H, Haraldsson GG, Kristinsson B (1997) Preparation of highly purified concentrates of eicosapentaenoic acid and docosahexaenoic acid. J Am Oil Chem Soc 74:1425–1429
11. Brunner G (1983) Selectivity of supercritical compounds and entrainers with respect to model substances. Fluid Phase Equilib 10:289–298
12. Brunner G (1994) Gas extraction: an introduction to fundamentals of supercritical fluids and the application to separation processes. Springer, New York
13. Brunner G (2005) Supercritical fluids: technology and application to food processing. J Food Eng 67:21–33
14. Brunner G (2009) Counter-current separations. J Supercrit Fluids 47:574–582
15. Brunner G, Peter S (1982) On the solubility of glycerides and fatty acids in compressed gases in the presence of an entrainer. Sep Sci Technol 17:199–214
16. 2 extraction of lycopene and b-carotene from ripe tomatoes. Dyes Pigm 44:27–32
17. Campos L, Michielin EMZ, Danielski L, Ferreira SR (2005) Experimental data and modeling the supercritical fluid extraction of marigold (Calendula officinalis) oleoresin. J Supercrit Fluids 34:163–170
18. Cao X, Ito Y (2003) Supercritical fluid extraction of grape seed oil and subsequent separation of free fatty acids by high-speed counter-current chromatography. J Chromatogr A 1021:117–124
19. Catchpole OJ, King MB (1994) Measurement and correlation of binary diffusion coefficients in near critical fluids. Ind Eng Chem Res 33:1828–1837
20. Catchpole OJ, Von Kamp JC, Grey JB (1997) Extraction of squalene from shark liver oil in a packed column using supercritical carbon dioxide. Ind Eng Chem Res 36:4318–4324
21. 2 plus ethanol mixtures. J Supercrit Fluids 19:25–37
22. Catchpole OJ, MacKenzie AN, Grey JB (2002) Improvements in or relating to separation technology. NZ518504, WO03089399
23. Catchpole OJ, Grey JB, Mitchell KA, Lan JS (2004) Supercritical antisolvent fractionation of propolis tincture. J Supercrit Fluids 29:97–106
24. Catchpole OJ, Tallon SJ, Eltringham WE, Grey JB, Fenton KA, Vagi EM, Vyssotski MV, MacKenzie AN, Ryan J, Zhu Y (2009) The extraction and fractionation of specialty lipids using near critical fluids. J Supercrit Fluids 47:591–597
25. Chimowitz EH, Pennisi KJ (1986) Process synthesis concepts for supercritical gas extraction in the crossover region. AlChE J 32:1665–1676
26. Chrastil J (1982) Solubility of solids and liquids in supercritical gases. J Phys Chem 86:3016–3021
27. Christov M, Dohrn R (2002) High-pressure fluid phase equilibria: experimental methods and systems investigated (1994–1999). Fluid Phase Equilib 202:153–218
28. Cocero MJ, González S, Perez S, Alonso E (2000) Supercritical extraction of unsaturated products Degradation of b-carotene in supercritical extraction processes. J Supercrit Fluids 19:39–44
29. 2 and composition profile. Chem Eng Process 46:99–106
30. Darken LS (1948) Diffusion, mobility and their interrelation through free energy in binary metallic systems. Trans Am Inst Min Metall Eng 175:184–201
31. Dauksas E, Venskutonis PR, Povilaityte V, Sivik B (2001) Rapid screening of antioxidant activity of sage (Salvia officinalis L.) extracts obtained by supercritical carbon dioxide at different extraction conditions. Nahrung 45:338–341
32. de la Fuente JC, Oyarzún B, Quezadaa N, del Valle JM (2006) Solubility of carotenoid pigments (lycopene and astaxanthin) in supercritical carbon dioxide. Fluid Phase Equilib 247:90–95
33. Deiters UK, Schneider GM (1986) High pressure phase equilibria: experimental methods. Fluid Phase Equilib 29:145–160
34. 2 extraction and purification of compounds with antioxidant activity. J Agric Food Chem 54:2441–2469
35. Dobbs JM, Wong JM, Johnston KP (1986) Nonpolar co-solvents for solubility enhancement in supercritical fluid carbon-dioxide. J Chem Eng Data 31:303–308
36. Dohrn R, Brunner G (1995) High-pressure fluid-phase equilibria: experimental methods and systems investigated (1988–1993). Fluid Phase Equilib 106:213–282
37. Duarte C, Moldao-Martins M, Gouveia AF, Beirão da Costa S, Leitão AE, Bernardo-Gil MG (2004) Supercritical fluid extraction of red pepper (Capsicum frutescens L.). J Supercrit Fluids 30:155–161
38. Dyerberg J, Bang HO, Hjorne N (1975) Fatty acid composition of the plasma lipids in Greenland Eskimos. Am J Clin Nutr 28:958–966
39. Eisenbach W (1984) Supercritical fluid extraction: a film demonstration. Phys Chem Chem Phys 88:882–887
40. Ekart MP, Bennett KL, Ekart SM, Gurdial GS, Liotta CL, Eckert CA (1993) Co-solvent interactions in supercritical fluid solutions. AlChE J 39:235–248
41. El Boustani S, Colette C, Monnier L, Descomps B, de Paulet AC, Mendy F (1987) Enteral absorption in man of eicosapentaenoic acid in different chemical forms. Lipids 22:711–714
42. Eltringham W, Catchpole OJ (2008) Processing of fish oils by supercritical fluids. In: Martinez JL (ed) Supercritical fluid extraction of nutraceuticals and bioactive compounds. CRC Press/ Taylor & Francis, Boca Raton, FL
43. Fang T, Goto M, Wang X, Ding X, Geng J, Sasaki M, Hirose T (2007) Separation of natural tocopherols from soybean oil byproduct with supercritical carbon dioxide. J Supercrit Fluids 40:50–58
44. Favati F, King JW, Mazzanti M (1991) Supercritical carbon dioxide extraction of evening primrose oil. J Am Oil Chem Soc 68:422–427
45. FDA (2005) Qualified health claims: letter regarding tomatoes and prostate cancer (Lycopene health claim coalition; Docket no. 2004Q-0201). http://www.fda.gov/food/dietarysupple-ments/consumerInformation/ucm072767.html. Retrieved 1 June 2009
46. Fenghour A, Wakeham WA, Vesovic V (1998) The viscosity of carbon dioxide. J Phys Chem Ref Data 27:31–39
47. 2:high separation efficiency using an automated countercurrent column. J Supercrit Fluids 14:67–74
48. Fornari RE, Alessi P, Kikic L (1990) High pressure fluid phase equilibria: experimental methods and systems investigated (1978–1987). Fluid Phase Equilib 57:1–33
49. Fors SM, Eriksson CE (1990) Characterization of oils extracted from oats by supercritical carbon-dioxide. LWT Food Sci Technol 23:390–395
50. Foster N, Mammucari R, Dehghani F, Barrett A, Bezanehtak K, Coen E, Combes G, Meure L, Ng A, Regtop HL, Tandya A (2003) Processing pharmaceutical compounds using dense gas technology. Ind Eng Chem Res 42:6476–6493
51. 24 unsaturated fatty acid methyl esters in supercritical carbon dioxide. Ind Eng Chem Res 30:1323–1329
52. Funazukuri T, Kong CY, Kagei S (2004a) Effects of molecular weight and degree of unsaturation on binary diffusion coefficients for lipids in supercritical carbon dioxide. Fluid Phase Equilib 219:67–73
53. Funazukuri T, Kong CY, Kagei S (2004b) Impulse response techniques to measure binary diffusion coefficients under supercritical conditions. J Chromatogr A 1037:411–429
54. Gámez-Meza N, Noriega-Rodríguez JA, Medina-Juárez LA, Ortega-García J, Monroy-Rivera FJ, Toro-Vázquez HS, García HS, Angulo-Guerrero O (2003) Concentration of eicosapentaenoic acid and docosahexaenoic acid from fish oil by hydrolysis and urea complexation. Food Res Int 36:721–727
55. Gast K, Jungfer M, Saure C, Brunner G (2005) Purification of tocochromanols from edible oil. J Supercrit Fluids 34:17–25
56. Gironi F, Maschietti M (2006) Separation of fish oils ethyl esters by means of supercritical carbon dioxide: thermodynamic analysis and process modelling. Chem Eng Sci 61:5114–5126
57. Gomez AM, de la Ossa EM (2000) Quality of wheat germ oil extracted by liquid and supercritical carbon dioxide. J Am Oil Chem Soc 77:969–974
58. Gomez-Prieto MS, Caja MM, Herraiz M, Santa-Maria G (2003) Supercritical fluid extraction of all-trans-lycopene from tomato. J Agric Food Chem 51:3–7
59. 2 – solubility and kinetic functions. T ASAE 30:1865–1868
60. Gruger EH, Nelson RW, Stansby ME (1964) Fatty acid composition of oils from 21 species of marine fish, freshwater fish and shellfish. J Am Oil Chem Soc 41:662–667
61. Temelli F (2000) Correlating the solubility behavior of fatty acids, mono-, di-, and triglycerides, and fatty acid esters in supercritical carbon dioxide. Ind Eng Chem Res 39:4756–4766
62. Temelli F (2004) Correlating the solubility behavior of minor lipid components in supercritical carbon dioxide. J Supercrit Fluids 31:235–253
63. Temelli F (2005) Solubility behavior of ternary systems of lipids, co-solvents and supercritical carbon dioxide and processing aspects. J Supercrit Fluids 36:1–15
64. Temelli F (2006) Solubility behavior of ternary systems of lipids in supercritical carbon dioxide. J Supercrit Fluids 38:275–288
65. Temelli F (2007) Column fractionation of canola oil deodorizer distillate using supercritical carbon dioxide. J Am Oil Chem Soc 84:953–961
66. Gupta RB, Shim J-J (2007) Solubility in Supercritical Carbon Dioxide. CRC Press, Boca Raton, FL
67. Gurdial GS, Wells PA, Foster NR, Chaplin RP (1989) The role of polarity in correlations of solid-supercritical fluid phase systems. J Supercrit Fluids 2:85–96
68. Hartono R, Mansoori GA, Suwono A (2001) Prediction of solubility of biomolecules in supercritical solvents. Chem Eng Sci 56:6949–6958
69. He HP, Corke H, Cai JG (2003) Supercritical carbon dioxide extraction of oil and squalene from Amaranthus grain. J Agric Food Chem 51:7921–7925
70. Herrero M, Cifuentes A, Ibanez E (2006) Sub-and supercritical fluid extraction of functional ingredients from different natural sources: Plants, food-by-products, algae and microalgae – A review. Food Chem 98:136–148
71. Hicks CP (1978) A bibliography of thermodynamic quantities for binary fluid mixtures. In: McGlashan ML (ed) Chemical thermodynamics. Chemical Society, London
72. Higashi H, Iwai Y, Nakamura Y, Yamamoto S, Arai Y (1999) Correlation of diffusion coefficients for naphthalene and dimethylnaphthalene isomers in supercritical carbon dioxide. Fluid Phase Equilib 166:101–110
73. Higashi H, Iwai Y, Arai Y (2001) Solubilities and diffusion coefficients of high boiling compounds in supercritical carbon dioxide. Chem Eng Sci 56:3027–3044
74. Horrocks LA, Yeo YK (1999) Health benefits of docosahexaenoic acid (DHA). Pharmacol Res 40:211–225
75. Huang W, Li Z, Niu H, Li D, Zhang J (2008) Optimization of operating parameters for supercritical carbon dioxide extraction of lycopene by response surface methodology. J Food Eng 89:298–302
76. Ibanez E, Palacios J, Senorans FJ, Santa-Maria G, Tabera J, Reglero G (2000) Isolation and separation of tocopherols from olive by-products with supercritical fluids. J Am Oil Chem Soc 77:187–190
77. Jung J, Perrut M (2001) Particle design using supercritical fluids: literature and patent survey. J Supercrit Fluids 20:179–219
78. Kestin J, Zien TF, Whitelaw JH (1964) Viscosity of carbon dioxide in neighbourhood of critical point. Physica 30:161
79. Kim HJ, Lee SB, Park KA, Hong IK (1999) Characterization of extraction and separation of rice bran oil rich in EFA using SFE process. Sep Purif Technol 15:1–8
80. King MB, Mubarak A, Kim JD, Bott TR (1992) The mutual solubilities of water with supercritical and liquid carbon dioxides. J Supercrit Fluids 5:296–302
81. Knapp H, D€oring R, Oellrich L, Pl€ocker U, Prausnitz JM (1981) Vapor-Liquid equilibria for mixtures of low-boiling substances DECHEMA Chem. Data series VI
82. Krichnavaruk, Shotipruk A, Goto M, Pavasant P (2008) Supercritical carbon dioxide extraction of astaxanthin from Haematococcus pluvialis with vegetable oils as co-solvent. Bioresour Technol 99:5556–5560
83. Krokan HE, Bjerve KS, Mørk E (1993) The enteral bioavailability of eicosapentaenoic acid and docosahexaenoic acid is as good from ethyl esters as from glyceryl esters in spite of lower hydrolytic rates by pancreatic lipase in vitro. Biochim Biophys Acta 1168:59–67
84. Lang Q, Wai CM (2001) Supercritical fluid extraction in herbal and natural product studies – a practical review. Talanta 53:771–782
85. Lawson LD, Hughes BG (1988) Human absorption of fish oil fatty acids as triacylglycerols, free acids, or ethyl esters. Biochem Biophys Res Commun 152:328–335
86. Lee SK (2003) Method for isolating high-purified unsaturated fatty acids using crystallization. US Patent 6,664,405
87. Lee KT, Foglia TA (2001) Fractionation of menhaden oil and partially hydrogenated menhaden oil: characterization of triacylglycerol fractions. J Am Oil Chem Soc 78:297–303
88. Leeke G, Gaspar F, Santos R (2002) Influence of water on the extraction of essential oils from a model herb using supercritical carbon dioxide. Ind Eng Chem Res 41:2033–2039
89. Li S (2008) Application of supercritical fluids in traditional Chinese medicines and natural products. In: Martinez JL (ed) Supercritical fluid extraction of nutraceuticals and bioactive compounds. CRC Press/Taylor & Francis, Boca Raton, FL, pp 215–242
90. Li S, Varadarajan GS, Hartland S (1991) Solubilities of theobromine and caffeine in supercritical carbon dioxide: Correlation with density-based models. Fluid Phase Equilib 68:263–280
91. Linder M, Matouba E, Fanni J, Parmentier M (2002) Enrichment of salmon oil with n-3 PUFA by lipolysis, filtration and enzymatic re-esterification. Eur J Lipid Sci Technol 104:455–462
92. Liong KK, Wells PA, Foster NR (1991) Diffusion in supercritical fluids. J Supercrit Fluids 4:91–108
93. Lopes IMG, Bernardo-Gil MG (2005) Characterisation of acorn oils extracted by hexane and by supercritical carbon dioxide. Eur J Lipid Sci Technol 107:12–19
94. Lucien FP, Foster NR (2000) Solubilities of solid mixtures in supercritical carbon dioxide: a review. J Supercrit Fluids 17:111–134
95. Ma Q, Xu X, Gao Y, Wang Q, Zhao J (2008) Optimisation of supercritical carbon dioxide extraction of lutein esters from marigold (Tagetes erect L.) with soybean oil as a co-solvent. Int J Food Sci Technol 43:1763–1769
96. Macias-Sanchez MD, Serrano CM, Rodriguez M, de la Ossa EM, Lubian LM, Montero O (2008) Extraction of carotenoids and chlorophyll from microalgae with supercritical carbon dioxide and ethanol as co-solvent. J Sep Sci 31:1352–1362
97. 2 in a countercurrent packed column. J Supercrit Fluids 39:304–314
98. McHugh MA, Krukonis VJ (1986) Supercritical fluid extraction: principles and practice. Butter-worths, Boston, MA
99. Meireles MAA (2008) Extraction of bioactive compounds from Latin American plants. In: Martinez JL (ed) Supercritical fluid extraction of nutraceuticals and bioactive compounds. CRC Press/Taylor & Francis, Boca Raton, FL, pp 243–274
100. 2 extraction of carotenoids and other lipids from Chlorella vulgaris. Food Chem 53:99–103
101. Mendes RL, Nobre BP, Coelho JP, Palavra AF (1999) Solubility of b-carotene in supercritical carbon dioxide and ethane. J Supercrit Fluids 16:99–106
102. Michels A, Botzen A, Schuurman W (1957) The viscosity of carbon dioxide between 0C and 75C and at pressures up to 2000 atmospheres. Physica 23:95–102
103. Mishra VK, Temelli F, Ooraikul B (1993) Extraction and purification of omega-3-fatty-acids with an emphasis on supercritical-fluid extraction – a review. Food Res Int 26:217–226
104. Moure A, Cruz JM, Franco D, Manuel Domínguez J, Sineiro J, Domínguez H, Núñez MJ, Carlos Parajó J (2001) Natural antioxidants from residual sources. Food Chem 72:145–171
105. Mukhopadhyay M (2008) Processing spices using supercritical fluids. In: Martinez JL (ed) Supercritical fluid extraction of nutraceuticals and bioactive compounds. CRC Press/Taylor & Francis, Boca Raton, FL, pp 337–366
106. Murga R, Ruiz R, Beltran S, Cabezas JL (2000) Extraction of natural complex phenols and tannins from grape seeds by using supercritical mixtures of carbon dioxide and alcohol. J Agric Food Chem 48:3408–3412
107. Nagahama K (1996) VLE measurements at elevated pressures for process development. Fluid Phase Equilib 116:361–372
108. Nagy B, Simandi B (2008) Effects of particle size distribution, moisture content, and initial oil content on the supercritical fluid extraction of paprika. J Supercrit Fluids 46:293–298
109. 2. J Am Oil Chem Soc 65:109–117
110. Nilsson WB, Gauglitz EJ, Hudson JK (1989) Supercritical fluid fractionation of fish oil esters using incremental pressure programming and a temperature gradient. J Am Oil Chem Soc 66:1596–1600
111. NIST (2009) Isothermal properties for carbon dioxide. http://webbook.nist.gov. Retrieved 10 June 2009
112. Nobre BP, Mendes RL, Queiroz EM, Pessoa FP, Coelho JP, Palavra AF (2009) Calculation of solubilities for systems containing multiple non-volatile solutes and supercritical carbon dioxide. Ind Eng Chem Res 48:1551–1555
113. Nordoy A, Barstad L, Connor WE, Hatcher L (1991) Absorption of the n-3 eicosapentaenoic and docosahexaenoic acids as ethyl esters and triglycerides by humans. Am J Clin Nutr 53: 1185–1190
114. 2 extraction of sesame oil from raw seeds. J Food Sci Technol 39:496–501
115. Oliveira R, Rodrigues MF, Bernardo-Gil MG (2002) Characterization and supercritical carbon dioxide extraction of walnut oil. J Am Oil Chem Soc 79:225–230
116. Ollanketo M, Hartonen K, Riekkola ML, Holm Y, Hiltunen R (2001) Supercritical carbon dioxide extraction of lycopene in tomato skins. Eur Food Res Technol 212:561–565
117. Ooi CK, Bhaskar A, Yener MS, Tuan DQ, Hsu J, Rizvi SSH (1996) Continuous supercritical carbon dioxide processing of palm oil. J Am Oil Chem Soc 73:233–237
118. Özogul Y, Özogul F (2007) Fatty acid profiles of commercially important fish species from the Mediterranean, Aegean and Black Seas. Food Chem 100:1634–1638
119. 2 extraction of lipids from roasted pistachio nuts. T ASAE 41:679–684
120. Palma M, Taylor LT, Varela RM, Cutler SJ, Cutler HG (1999) Fractional extraction of compounds from grape seeds by supercritical fluid extraction and analysis for antimicrobial and agrochemical activities. J Agric Food Chem 47:5044–5048
121. Peker H, Srinivasan MP, Smith JM, McCoy BJ (1992) Caffeine extraction rates from coffee beans with supercritical carbon dioxide. AlChE J 38:761–770
122. Perretti G, Motori A, Bravi E, Favati F, Montanari L, Fantozzi P (2007) Supercritical carbon dioxide fractionation of fish oil fatty acid ethyl esters. J Supercrit Fluids 40:349–353
123. Perrut M (2000) Supercritical fluid applications: industrial developments and economic issues. Ind Eng Chem Res 39:4531–4535
124. Peusch M, M€uller-Seitz E, Petz M, M€uller A, Anklam E (1997) Extraction of capsaicinoids from chillies (Capsicum frutescens L.) and paprika (Capsicum annuum L.) using supercritical fluids and organic solvents. Z. Lebensm. Unters. Forsch. Eur Food Res Technol 204:351–355
125. Ramírez Fajardo A, Esteban Cerdán L, Robles Medina A, Muñío Martínez MM, Hita Peña E, Molina Grima E (2006) Concentration of eicosapentaenoic acid by selective esterification using lipases. J Am Oil Chem Soc 83:215–221
126. Raspo I, Nicolas C, Neau E, Meradji S (2008) Diffusion coefficients of solids in supercritical carbon dioxide: modelling of near critical behaviour. Fluid Phase Equilib 263:214–222
127. Ratledge C (2004) Fatty acid biosynthesis in microorganisms being used for Single Cell Oil production. Biochimie 86:807–815
128. Reverchon E (1992) Fractional separation of SCF extracts from marjoram leaves: mass transfer and optimization. J Supercrit Fluids 5:256–261
129. Reverchon E (1997) Supercritical fluid extraction and fractionation of essential oils and related products. J Supercrit Fluids 10:1–37
130. Reverchon E, De Marco I (2006) Supercritical fluid extraction and fractionation of natural matter. J Supercrit Fluids 38:146–166
131. 2 extraction of hiprose seed oil: experiments and mathematical modelling. Chem Eng Sci 55:2195–2201
132. 2. J Supercrit Fluids 17:35–44
133. Riha V, Brunner G (2000) Separation of fish oil ethyl esters with supercritical carbon dioxide. J Supercrit Fluids 17:55–64
134. Rosa PTV, Meireles MAA (2005) Rapid estimation of the manufacturing cost of extracts obtained by supercritical fluid extraction. J Food Eng 67:235–240
135. Rozzi NL, Singh RK, Vierling RA, Watkins BA (2002) Supercritical fluid extraction of lycopene from tomato processing byproducts. J Agric Food Chem 50:2638–2643
136. Ruckenstein E, Shulgin I (2001) Entrainer effect in supercritical mixtures. Fluid Phase Equilib 180:345–359
137. Ruckenstein E, Shulgin I (2002) The solubility of solids in mixtures composed of a supercritical fluid and an entrainer. Fluid Phase Equilib 200:53–67
138. Ruivo R, Cebola MJ, Simoes PC, Nunes da Ponte M (2002) Fractionation of edible oil model mixtures by supercritical carbon dioxide in a packed column. 2. A mass-transfer study. Ind Eng Chem Res 41:2305–2315
139. Ruivo R, Couto R, SimÃmes PC (2008) Supercritical carbon dioxide fractionation of the model mixture squalene/oleic acid in a membrane contactor. Sep Purif Technol 59:231–237
140. 2. Ind Eng Chem Res 42:6641–6646
141. Sacchetti G, Maietti S, Muzzoli M, Scaglianti M, Manfredini S, Radice M, Bruni R (2005) Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods. Food Chem 91:621–632
142. Sakaki K (1992) Solubility of b-carotene in dense carbon-dioxide and nitrous-oxide from 308 to 323 K and from 9.6 to 30 MPa. J Chem Eng Data 37:249–251
143. 2 based on a binary and a multicomponent complex system. J Supercrit Fluids 37:342–349
144. 2 plus ethanol) extraction of b-carotene from apricot pomace using response surface methodology. J Supercrit Fluids 34:331–338
145. Sanderson P, Finnegan YE, Williams CM, Calder PC, Burdge GC, Wootton SA, Griffin BA, Millward DJ, Pegge NC, Bemelmans WJE (2002) UK Food Standards Agency a-linolenic acid workshop report. Br J Nutr 88:573–579
146. Schmitt WJ, Reid RC (1985) The influence of the solvent gas on solubility and selectivity in supercritical extraction. In: Penninger JML, Radosz M, McHugh MA, Krukonis VJ (eds) Supercritical Fluid Technology. Elsevier, New York, pp 123–147
147. Schmitt WJ, Reid RC (1986) The use of entrainers in modifying the solubility of phenanthrene and benzoic acid in supercritical carbon dioxide and ethane. Fluid Phase Equilib 32:77–99
148. Senanayake S, Shahidi F (2000) Concentration of docosahexaenoic acid (DHA) from algal oil via urea complexation. J Food Lipids 7:51–61
149. Shahidi F, Wanasundara UN (1998) Omega-3 fatty acid concentrates: nutritional aspects and production technologies. Trends Food Sci Technol 9:230–240
150. Shen Z, Palmer MV, Ting SST, Fairclough RJ (1996) Pilot scale extraction of rice bran oil with dense carbon dioxide. J Agric Food Chem 44:3033–3039
151. 2. J Food Eng 93:431–436
152. 2. J Agric Food Chem 45:2066–2069
153. 2 and data correlation by a density based model. Fluid Phase Equilib 109:131–138
154. Somayajulu GR (1989) Estimation procedures for critical constants. J Chem Eng Data 34:106–120
155. 2.2. Extraction of grape oil. Chem Eng Sci 49:415–420
156. Srinivasan K (2005) Spices as influencers of body metabolism: an overview of three decades of research. Food Res Int 38:77–86
157. Staby A, Mollerup J (1993) Separation of constituents of fish oil using supercritical fluids: a review of experimental solubility, extraction, and chromatographic data. Fluid Phase Equilib 91:349–386
158. Stahl E, Gerard D (1985) Solubility behaviour and fractionation of essential oils in dense carbon dioxide. Perfum Flavor 10(2):29–30, 32, 34–37
159. Stahl E, Quirin KW (1983) Dense gas extraction on a laboratory scale: a survey of some recent results. Fluid Phase Equilib 10:269–278
160. Stahl HCE, Schilz W (1976) Extraktion mit €uberkritischen Gasen in direkter Kopplung mit der D€unnschicht-Chromatographie Anwendungsm€oglichkeiten auf dem Naturstoffgebiet. Chem Ing Tech 48:773–778
161. Stockfleth R, Brunner G (2001) Holdup, pressure drop, and flooding in packed countercurrent columns for the gas extraction. Ind Eng Chem Res 40:347–356
162. Strøm A, Jensen RA (1951) Mortality from circulatory diseases in Norway 1940–1945. Lancet 1:126–129
163. Suárez JJ, Medina I, Bueno JL (1998) Diffusion coefficients in supercritical fluids: available data and graphical correlations. Fluid Phase Equilib 153:167–212
164. Sun M, Temelli F (2006) Supercritical carbon dioxide extraction of carotenoids from carrot using canola oil as a continuous co-solvent. J Supercrit Fluids 37:397–408
165. Taniguchi M, Tsuji T, Shibata M, Kobayashi T (1985) Extraction of oils from wheat-germ with supercritical carbon-dioxide. Agric Biol Chem 49:2367–2372
166. Temelli F, Saldaña MDA, Moquin PHL, Sun M (2008) Supercritical fluid extraction of specialty oils. In: Martinez JL (ed) Supercritical fluid extraction of nutraceuticals and bioactive compounds. CRC Press/Taylor & Francis, Boca Raton, FL, pp 51–101
167. Thana P, Machmudah S, Goto M, Sasaki M, Pavasant P, Shotipruk A (2008) Response surface methodology to supercritical carbon dioxide extraction of astaxanthin from Haematococcus pluvialis. Bioresour Technol 99:3110–3115
168. Tilly KD, Foster NR, Macnaughton SJ, Tomasko DL (1994) Viscosity correlations for binary supercritical fluids. Ind Eng Chem Res 33:681–688
169. Topal U, Sasaki M, Goto M, Hayakawa K (2006) Extraction of lycopene from tomato skin with supercritical carbon dioxide: Effect of operating conditions and solubility analysis. J Agric Food Chem 54:5604–5610
170. Tuan DQ, Zollweg JA, Harriott P, Rizvi SSH (1999) Measurement and modeling of viscosity of supercritical carbon dioxide/biomaterial(s) mixtures. Ind Eng Chem Res 38:2129–2136
171. Uquiche E, del Valle JM, Ortiz J (2004) Supercritical carbon dioxide extraction of red pepper (Capsicum annuum L.) oleoresin. J Food Eng 65:55–66
172. Vagi E, Simandi B, Suhajda A, Hethelyi E (2005) Essential oil composition and antimicrobial activity of Origanum majorana L. extracts obtained with ethyl alcohol and supercritical carbon dioxide. Food Res Int 38:51–57
173. Vagi E, Simandi B, Vasarhelyine KP, Daood H, Kery A, Doleschall F, Nagy B (2007) Supercritical carbon dioxide extraction of carotenoids, tocopherols and sitosterols from industrial tomato by-products. J Supercrit Fluids 40:218–226
174. Van Alsten JG, Eckert CA (1993) Effect of entrainers and of solute size and polarity in supercritical fluid solutions. J Chem Eng Data 38:605–610
175. 2 extraction of lycopene from tomato in the presence of vegetable oil as co-solvent. J Supercrit Fluids 29:87–96
176. Vega PJ, Balaban MO, Sims CA, O’Keefe SF, Cornell JA (1996) Supercritical carbon dioxide extraction efficiency for carotenes from carrots by RSM. J Food Sci 61:757–759
177. Vesovic V, Wakeham WA, Olchowy GA, Sengers JV, Watson JTR, Millat J (1990) The transport-properties of carbon-dioxide. J Phys Chem Ref Data 19:763–808
178. Visentainer JV, D’Addio Noffs M, De Oliveira Carvalho P, De Almeida VV, De Oliveira CC, De Souza NE (2007) Lipid content and fatty acid composition of 15 marine fish species from the southeast coast of Brazil. J Am Oil Chem Soc 84:543–547
179. Walsh JM, Ikonomou GD, Donohue MD (1987) Supercritical phase-behavior – the entrainer effect. Fluid Phase Equilib 33:295–314
180. Wang C, Harris WS, Chung M, Lichtenstein AH, Balk EM, Kupelnick B, Jordan HS, Lau J (2006) n-3 Fatty acids from fish or fish-oil supplements, but not a-linolenic acid, benefit cardiovascular disease outcomes in primary-and secondary-prevention studies: a systematic review. Am J Clin Nutr 84:5–17
181. Ward OP, Singh A (2005) Omega-3/6 fatty acids: alternative sources of production. Process Biochem 40:3627–3652
182. Weidner E (2009) High pressure micronization for food applications. J Supercrit Fluids 47:556–565
183. Wiebe R (1941) The binary system carbon dioxide-water under pressure. Chem Rev 29:475–481
184. Yener ME, Kashulines P, Rizvi SSH, Harriott P (1998) Viscosity measurement and modeling of lipid supercritical carbon dioxide mixtures. J Supercrit Fluids 11:151–162
185. Ziger DH, Eckert CA (1983) Correlation and prediction of solid-supercritical fluid phase equilibria. Ind Eng Chem Process Des Dev 22:582–588
186. Zuta CP, Simpson BK, Chan HM, Phillips L (2003) Concentrating PUFA from mackerel processing waste. J Am Oil Chem Soc 80:933–936