2 0 2019 joh kan 0 journal Original John, D.[Deepitha] Kancharlapalli, C. P.[Chinaraga Pitchaiah] Nagarajan, S.[Sivaraman] J. Chem. Eng. Data 2019 2020-09-29 Solubility of Phenylphosphinic Acid in Supercritical Carbon Dioxide and the Influence of Methanol on the Solubility Behavior The solubility of phenylphosphinic acid (PPA) was measured for the first time in supercritical carbon dioxide (SCCO2) at 313, 323 & 333 K with pressure ranging from 10-20 MPa using a dynamic flow technique. The solubility of PPA in neat SCCO2 ranged from 0.1x10-5 to 18x10-5 mol/mole. The influence of co-solvent, methanol on solubility behavior was studied by measuring the solubility of PPA in SCCO2 + methanol medium (1 and 4 mol% methanol) at 313 & 323 K with pressure varying from 10-20 MPa. The highest solubility of PPA in SCCO2+methanol mixture is 29.4x10-4mol/mole at 313 K and 20 MPa with a methanol composition of 4 mol%. The solubilities in neat SCCO2 were correlated using different semi-empirical equations (Mendez-Teja, Chrastil and Bartle) with an average deviation of less than10%. The solubility in the presence of methanol was correlated with four semi-empirical/empirical models (modified Chrastil, modified Mendez-Teja, Garlapati model and Jouyban equation); among these models, Jouyban model resulted in better correlation with an average deviation of 5%. 10.1021/acs.jced.9b00732 12 64 5775-5784 1 InChI=1S/CO2/c2-1-3 CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide CO2 1 Commercial source 1 99.9 3 Stated by supplier 2 InChI=1S/CH4O/c1-2/h2H,1H3 OKKJLVBELUTLKV-UHFFFAOYSA-N methanol methyl alcohol CH4O 1 Commercial source 1 99.8 3 Stated by supplier 3 InChI=1S/C6H7O2P/c7-9(8)6-4-2-1-3-5-6/h1-5,9H,(H,7,8) MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid C6H7O2P 1 Commercial source 1 99 3 Stated by supplier 4 InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid (.+-.)-.alpha.-hydroxybenzeneacetic acid (.+-.)-.alpha.-hydroxyphenylacetic acid (.+-.)-2-hydroxy-2-phenylethanoic acid (.+-.)-mandelic acid (RS)-mandelic acid .alpha.-hydroxy-.alpha.-toluic acid .alpha.-hydroxybenzeneacetic acid .alpha.-hydroxybenzeneethanoic acid .alpha.-hydroxyphenylacetic acid 2-hydroxy-2-phenylacetic acid 2-phenyl-2-hydroxyacetic acid 2-phenylglycolic acid DL-hydroxy(phenyl)acetic acid DL-mandelic acid amygdalic acid benzeneacetic acid, .alpha.-hydroxy- dl-mandelic acid paramandelic acid phenylglycolic acid phenylhydroxyacetic acid uromaline C8H8O3 1 Commercial source 1 99 3 Stated by supplier 1 3 1 1 1 Principal objective of the work EP EP 6/16/2020 1

Mole fraction Chromatography 3

Fluid (supercritical or subcritical phases) Direct value, X 1 Data file compiler Propagation of evaluated standard uncertainties 95 Fluid (supercritical or subcritical phases) Crystal 3 1 Temperature, K Fluid (supercritical or subcritical phases) 2 Pressure, kPa Fluid (supercritical or subcritical phases) 1 313 4 2 10000 1 1 2e-05 2 1 2e-06 1 313 4 2 12000 2 1 4.1e-05 2 1 5e-06 1 313 4 2 14000 2 1 6.1e-05 2 1 7e-06 1 313 4 2 16000 2 1 7.5e-05 2 1 9e-06 1 313 4 2 18000 2 1 9.5e-05 2 1 1.1e-05 1 313 4 2 20000 1 1 0.000109 3 1 1.3e-05 1 323 4 2 10000 1 1 2.6e-06 2 1 4e-07 1 323 4 2 12000 2 1 2.6e-05 2 1 3e-06 1 323 4 2 14000 2 1 5.6e-05 2 1 7e-06 1 323 4 2 16000 2 1 8.6e-05 2 1 1e-05 1 323 4 2 18000 2 1 0.00011 3 1 1.3e-05 1 323 4 2 20000 1 1 0.000124 3 1 1.5e-05 1 333 4 2 10000 1 1 1e-06 2 1 1e-07 1 333 4 2 12000 2 1 8.8e-06 2 1 1.1e-06 1 333 4 2 14000 2 1 3.6e-05 2 1 4e-06 1 333 4 2 16000 2 1 7.1e-05 2 1 9e-06 1 333 4 2 18000 2 1 0.000124 3 1 1.5e-05 1 333 4 2 20000 1 1 0.00016 3 1 1.9e-05 2 3 1 1 1 2 1 Principal objective of the work EP EP 6/16/2020 1

Mole fraction Chromatography 3

Fluid (supercritical or subcritical phases) Direct value, X 1 2 1 Data file compiler Propagation of evaluated standard uncertainties 95 Fluid (supercritical or subcritical phases) Crystal 3 1 Pressure, kPa Fluid (supercritical or subcritical phases) 2 Temperature, K Fluid (supercritical or subcritical phases) 3 Solvent: Mole fraction 2 Fluid (supercritical or subcritical phases) 1 10000 1 2 313 4 3 0.01 1 1 2.8e-05 2 1 1.1e-05 1 12000 2 2 313 4 3 0.01 1 1 0.000103 3 1 2.2e-05 1 14000 2 2 313 4 3 0.01 1 1 0.00011 3 1 3.4e-05 1 16000 2 2 313 4 3 0.01 1 1 0.000201 3 1 5.5e-05 1 18000 2 2 313 4 3 0.01 1 1 0.00029 2 1 8e-05 1 20000 1 2 313 4 3 0.01 1 1 0.0004 2 1 0.0001 1 10000 1 2 323 4 3 0.01 1 1 3e-06 1 1 2e-06 1 12000 2 2 323 4 3 0.01 1 1 1.9e-05 2 1 6e-06 1 14000 2 2 323 4 3 0.01 1 1 4.9e-05 2 1 1.4e-05 1 16000 2 2 323 4 3 0.01 1 1 8.7e-05 2 1 2.7e-05 1 18000 2 2 323 4 3 0.01 1 1 0.000155 3 1 4.6e-05 1 20000 1 2 323 4 3 0.01 1 1 0.00021 2 1 6e-05 1 10000 1 2 313 4 3 0.04 1 1 0.00023 2 1 6e-05 1 12000 2 2 313 4 3 0.04 1 1 0.00062 2 1 0.00011 1 14000 2 2 313 4 3 0.04 1 1 0.00106 3 1 0.00019 1 16000 2 2 313 4 3 0.04 1 1 0.00167 3 1 0.00029 1 18000 2 2 313 4 3 0.04 1 1 0.00234 3 1 0.00039 1 20000 1 2 313 4 3 0.04 1 1 0.00292 3 1 0.00049 1 10000 1 2 323 4 3 0.04 1 1 2.4e-05 2 1 1.5e-05 1 12000 2 2 323 4 3 0.04 1 1 0.000158 3 1 3.7e-05 1 14000 2 2 323 4 3 0.04 1 1 0.000401 3 1 8.1e-05 1 16000 2 2 323 4 3 0.04 1 1 0.00083 2 1 0.00015 1 18000 2 2 323 4 3 0.04 1 1 0.00139 3 1 0.00024 1 20000 1 2 323 4 3 0.04 1 1 0.00181 3 1 0.00031 3 4 1 1 1 Principal objective of the work EP EP 6/16/2020 1

Mole fraction Chromatography 4