Researcher

Matthew McBride

Objective

To determine solubility of phenanthrene-9-carboxaldehyde in THF and methanol and to investigate the solubility of 2-naphthaldehyde in ethanol, 1:1 ethanol/water mixture and methanol.

Procedure

Add the solute to a vial with the solvent and allow the solution to shake on the 25°C shake flask apparatus. Measure solubility using SAMS HNMR.

Results

Picture #1: Crystals still present in the 0.156M solution of 2-naphthaldehyde in a 1:1 ethanol/water mixture
flashtalk 2-naph not soluble.png


Vial D: phenanthrene-9-carboxaldehyde in THF
SAMS Sheet
24 hours: 1.602 M
48 hours: 1.471 M

Vial E: phenanthrene-9-carboxaldehyde in methanol
SAMS Sheet
24 hours: 0.038 M
48 hours: 0.031 M

Discussion

Two consecutive values for the solubility measurements were obtained, so the solution was saturated. 2-naphthaldehyde cannot be more than 0.156M soluble in a 1:1 ethanol/water mixture due to the fact that crystals were still present in the solution at 24 hours of shaking on the shake flask.

Conclusion

The solubility of phenanthrene-9-carboxaldehyde is about 1.5M in THF and 0.03M in methanol. 2-naphthaldehyde is less than 0.156M soluble in 1:1 ethanol/water mixture.

Log

2012-08-15

16:14 Added 0.0205 g of 2-naphthaldehyde to 1-dram screw cap vial A. Added 0.0244 g of 2-naphthaldehyde to 1-dram screw cap vial B. Added 0.0194 g of 2-naphthaldehyde to 1-dram screw cap vail C. Added 0.2782 g of phenanthrene-9-carboxaldehyde to 1-dram screw cap vial D. Added 0.1173 g of phenanthrene-9-carboxaldehyde to 1-dram screw cap vial E.
16:33 Added 1 mL of ethanol to vial A. Added 1 mL of 1:1 ethanol/water mixture to vial B. Added 1 mL of methanol to vial C.
16:40 Added 1 mL of THF to vial D. Added 1 mL of methanol to vial E.
16:50 Sealed the screw cap vials with parafilm and placed on the 25°C shake flask apparatus.

2012-08-16

10:49 Crystals were visible in vial B and E. Added 0.1176 g of phenanthrene-9-carboxaldehyde to vial D. Placed vial D back on the shake flask. Took picture of vial B with solid.
16:29 Removed vial D and E from shake flask. Added supernatant from vial D to NMR Tube 1 and supernatant from vial E to NMR Tube 2. Both were inner coaxial NMR tubes and were placed in a thin walled NMR tube holding CDCl3. Analyzed by 500MHz HNMR.

2012-08-17

10:41 Removed the vials D and E from the shake flask. Crystals were visible in both vials.
10:55 Added the supernatant from Vial D to NMR Tube 1 and the supernatant from Vial E to NMR Tube 2. Both were inner coaxial NMR tubes and analyzed by 500MHz HNMR using CDCl3 in a thin walled NMR tube as the reference.