Supporting Information
Phase Equilibrium and Bioproduction of the Aroma Compound 2–Phenylethanol in a Biphasic Aqueous System
Urszula Domańska†
Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Thermodynamic Research Unit, School of Chemical Engineering, University of KwaZulu-Natal, Howard College Campus, King George V Avenue, Durban 4001, South Africa
Marcin Okuniewski
Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Patrycja Okuniewska
Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Kamil Paduszyński
Department of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Tomasz Turowski
Faculty of Chemistry, Institute of Biotechnology, Warsaw University of Technology, 00-664 Noakowskiego 3, Warsaw, Poland
Table 1S The sources, CAS numbers, mass fraction purities, purification methods and experimental and literature temperature of fusion and density of materials used
CAS No / Source / Initial mass fraction purity / Purification method / Exp. Temp. of fusion, Tfus,e
Lit. Temp. of fusion, Tfus,l / Exp. Density
r/g cm-3
(298.15; 101.33 kPa) / Lit. Density
r/g cm-3
(298.15; 101.33 kPa) /
2-Phenylethanol (PEA) / Sigma-Aldrich Chemie GmbH, Germany / ≥ 0.99 / Destilation
Molec. Sieves 4A / 1.02659 / 1.026565a
L-Penylalanine (L-Phe) / Sigma-Aldrich Chemie GmbH, Germany / ≥ 0.99 / - / - / Solid phase / Solid phase
Decan-1-ol / Fluka / ≥ 0.99 / Molec. Sieves 4A / Tfus,e = 280,0 K
Tfus,l = 279.5 Kb / 0.82296 / 0.82292a
Hexadecan-1-ol / Sigma-Aldrich Chemie GmbH, Germany / ≥ 0.99 / - / Tfus,e = 322.6 K
Tfus,l = 322.6 Ka
Otadecan-1-ol / Sigma-Aldrich Chemie GmbH, Germany / ≥ 0.99 / - / Tfus,e = 331.0K
Tfus,l = 331.1K
Eicosan-1-ol / Sigma-Aldrich Chemie GmbH, Germany / >0.95 / - / Tfus,e = 337.9 K
Tfus,l = 336.6 Ka
Eicosane / Sigma-Aldrich Chemie GmbH, Germany / >0.95 / Tfus,e = 309.8 K
Tfus,l = 309.7 Kc
Oleic acid / Sigma-Aldrich Chemie GmbH, POCH, Poland Germany / ≥0.99
Ph.Eur. / Molec. Sieves 4A / Tfus,e = 286.3 K / 0.89182 / 0.89187a
Agar / Sigma-Aldrich Chemie GmbH, Germany / for microbiology / - / Solid phase / Solid phase
Yeast extract / Fluka / for microbiology / - / Solid phase / Solid phase
Yeast peptone dextrose / Fluka / for microbiology / - / Solid phase / Solid phase
Glucose / POCH, Poland / Pure P. A. / - / Tfus,e = 430.8 K
Tfus,l = 429.7 Kd
KH2PO4 / POCH, Poland / Pure P. A / - / Solid phase / Solid phase
MgSO4×7H2O / Chempur / Pure P. A / - / Solid phase / Solid phase
a DIPPR
b Yaws, C. L. Yaws’ Thermophysical Properties ofChemicals and Hydrocarnbons (Electronic Editio) Knovel. Online version available at: http://knovel.com/web/portal/browse/display?_EXT_KNOVEL_DISPLAY_bookid=29068&VerticalID=0(accesse May 2013).
c M.J.M. Van Oort, M.A. White, Thermochim. Acta, 86 (1985) 1-6.
d A. Magoń, M. Pyda, Carbohydr. Res. 346 (2011) 2558–2566.
Table 2S Experimental solid-liquid phase equilibrium data for {an alcohol (1) + PEA (2)} binary systems
Decan-1-ol
1.0000 / 280.0 / 0.6609 / 272.6 / 0.2861 / 262.9
0.9457 / 279.3 / 0.6107 / 271.5 / 0.2331 / 260.9
0.9045 / 277.7 / 0.5587 / 270.3 / 0.1828 / 258.1
0.8526 / 277.0 / 0.5059 / 269.1 / 0.1329 / 255.3
0.8010 / 275.7 / 0.4266 / 267.2 / 0.1009 / 252.7
0.7557 / 274.8 / 0.3879 / 266.1 / 0.0489 / 250.0
0.7077 / 273.5 / 0.3370 / 264.4 / 0.0000 / 246.0
Hexadecan-1-ol
1.0000 / 322.6 / 0.7011 / 317.5 / 0.3996 / 312.0
0.9529 / 321.4 / 0.6884 / 317.8 / 0.3961 / 310.8
0.9419 / 321.1 / 0.6638 / 317.4 / 0.3500 / 309.7
0.9358 / 321.7 / 0.6440 / 317.4 / 0.3080 / 309.1
0.8936 / 320.9 / 0.6231 / 317.0 / 0.2766 / 307.8
0.8669 / 320.5 / 0.6011 / 316.3 / 0.2424 / 306.7
0.8416 / 320.3 / 0.5789 / 315.9 / 0.2122 / 306.1
0.8290 / 320.6 / 0.5601 / 315.4 / 0.1890 / 304.7
0.8221 / 320.1 / 0.5424 / 314.9 / 0.1649 / 303.8
0.8031 / 319.8 / 0.5271 / 314.5 / 0.1398 / 301.8
0.7852 / 319.2 / 0.5063 / 314.3 / 0.1063 / 299.9
0.7761 / 319.0 / 0.5012 / 314.1 / 0.0803 / 297.7
0.7630 / 318.8 / 0.4747 / 313.7 / 0.0602 / 294.2
0.7562 / 318.6 / 0.4692 / 313.4 / 0.0399 / 291.3
0.7434 / 318.8 / 0.4510 / 313.3 / 0.0305 / 288.2
0.7382 / 318.7 / 0.4374 / 312.7 / 0.0204 / 284.8
0.7358 / 318.4 / 0.4235 / 312.4 / 0.0116 / 312.0
0.7190 / 318.1 / 0.3996 / 312.0
Octadecan-1-ol
1.0000 / 331.0 / 0.6209 / 322.3 / 0.2006 / 312.8
0.9498 / 329.4 / 0.5732 / 321.3 / 0.1504 / 311.4
0.8869 / 328.7 / 0.5109 / 319.2 / 0.1047 / 309.8
0.8475 / 327.7 / 0.4586 / 318.4 / 0.0502 / 305.2
0.7995 / 326.5 / 0.4008 / 315.4 / 0.0353 / 302.5
0.7641 / 325.5 / 0.3496 / 315.0 / 0.0000 / 246.0
0.7227 / 324.7 / 0.2998 / 314.9
0.6822 / 323.8 / 0.2492 / 313.7
Eicosan-1-ol
1.0000 / 337.9 / 0.5368 / 326.7 / 0.2196 / 317.7
0.9607 / 336.3 / 0.5021 / 325.8 / 0.1902 / 316.8
0.9239 / 335.5 / 0.4734 / 325.2 / 0.1610 / 315.6
0.8811 / 334.5 / 0.4477 / 324.4 / 0.1315 / 314.5
0.8431 / 333.6 / 0.4217 / 323.9 / 0.1012 / 313.5
0.8002 / 332.7 / 0.3972 / 323.3 / 0.0911 / 312.9
0.7611 / 331.9 / 0.3733 / 322.8 / 0.0810 / 313.3
0.7278 / 331.5 / 0.3506 / 322.2 / 0.0841 / 313.6
0.6904 / 330.0 / 0.3271 / 321.9 / 0.0595 / 312.9
0.6502 / 329.2 / 0.3050 / 321.2 / 0.04043 / 310.9
0.6160 / 328.5 / 0.2806 / 320.0 / - / -
0.5735 / 327.7 / 0.2506 / 318.7 / - / -
Table 3S Experimental solid-liquid and liquid-liquid phase equilibrium data for {solvent (1) + PEA (2)} binary systems
Eicosane
1.0000 / 309.8 / 0.3848 / 357.7
0.9624 / 309.4 / 0.3491 / 358.9
0.9311 / 309.2 / 0.2915 / 358.9
0.8909 / 309.0 / 0.2357 / 359.0
0.8648 / 308.9 / 0.1996 / 359.2
0.8391 / 308.9 / 0.1854 / 359.0
0.7949 / 323.0 / 0.1550 / 358.0
0.7521 / 329.2 / 0.0950 / 352.7
0.7088 / 334.5 / 0.0773 / 350.4
0.6667 / 339.8 / 0.0649 / 344.5
0.6190 / 344.4 / 0.0452 / 334.9
0.5600 / 349.4 / 0.0308 / 323.6
0.5100 / 352.8 / 0.0201 / 309.9
0.4355 / 356.0 / 0.0093 / 303.9
Oleic acid
1.0000 / 286.3 / - / 0.5041 / 282.9 / 306.4
0.9536 / 285.9 / - / 0.4548 / 282.9 / 310.4
0.9126 / 285.6 / - / 0.4022 / 282.8 / 310.4
0.8997 / 285.9 / - / 0.3613 / - / 305.1
0.8908 / 285.6 / - / 0.3189 / 282.8 / 300.3
0.8702 / 285.5 / - / 0.2872 / 282.8 / 296.4
0.8625 / 285.5 / - / 0.2608 / - / 294.1
0.8599 / 285.4 / - / 0.2437 / 282.7 / 293.1
0.8488 / 285.2 / - / 0.2203 / 274.6 / 291.7
0.8193 / - / 285.9 / 0.1982 / 270.7 / 289.0
0.7773 / - / 287.0 / 0.1805 / 281.8 / 288.1
0.7244 / 283.4 / 287.7 / 0.1789 / - / 288.2
0.6779 / 283.1 / 289.5 / 0.1508 / - / 285.4
0.6192 / 283.1 / 292.7 / 0.1203 / - / 282.8
0.5784 / 283.0 / 295.8 / 0.0804 / 274.3 / -
0.5429 / - / 300.6 / 0.0367 / 268.8 / -
Table 4S Experimental solid-liquid phase equilibrium data at high pressure for {decan-1-ol (1) + PEA (2)} binary systems
x1 / p/MPa / x1 / p/MPa / x1 / p/MPa
1.0000 / 108 / 1.0000 / 166 / 1.0000 / 223
0.8827 / 125 / 0.8827 / 179 / 0.8827 / 233
0.7836 / 137 / 0.7836 / 195 / 0.7836 / 258
0.6907 / 151 / 0.6907 / 210 / 0.6907 / 270
0.5621 / 174 / 0.5621 / 231 / 0.5621 / 306
0.4502 / 195 / 0.4502 / 256 / 0.4502 / 334
0.3527 / 227 / 0.3527 / 299 / 0.3527 / 374
0.2942 / 246 / 0.2942 / 316 / 0.2942 / 400
0.2409 / 272 / 0.2409 / 364 / 0.2409 / 438
0.1969 / 290 / 0.1969 / 412 / 0.1969 / 480
0.1455 / 376 / 0.1455 / 461 / 0.1455 / 560
0.1040 / 444 / 0.1040 / 552 / 0.1040 / 667
0.0457 / 649 / 0.0457 / 720 / 0.0457 / 1000
2