EXP308

=Researcher= Matthew McBride =Objective= To determine the solubility of trans-dibenzalacetone (Product 307B from EXP307) in Benzene, THF, Cyclohexane, Cyclohexanone, and Toluene by SAMS HNMR using the Shake Plate method to dissolve. =Procedure= Approximately 0.1 g of the trans-dibenzalacetone was added to five 1-dram screw cap vial and 0.5 mL of a different solvent was added to each vial. The vials were sealed and allowed to mix on the shake plate (vortex) overnight. The vials were removed from the shake plate and allowed to cool to room temperature. If crystals were present in the solution, it was determined that the solution was saturated. A few drops of the saturated solution was then analyzed by HNMR and the solubility was determined using a SAMS Sheet. The vials were sealed again and placed back on the shake plate to mix the solutions for another 24 hours. The saturated solutions were again analyzed by HNMR and the solubility determined. The second solubility measurement was obtained to be sure the solution was saturated (the measured solubility should be the same after both measurements). =Results= [|SAMS Sheet 1] - solubility in benzene: Vial 1 24 Hours: 0.769M at 24°C 72 Hours: 0.940M at 25°C

[|SAMS Sheet 2] - solubility in THF: Vial 2 24 Hours: Unable to obtain a Value 72 Hours: 1.290M at 25°C 96 Hours: 1.485M at 25°C

[|SAMS Sheet 3] - solubility in cyclohexane: Vial 3 24 Hours: 0.034M at 24°C 72 Hours: 0.027M at 25°C

[|SAMS Sheet 4] - solubility in cyclohexanone: Vial 4 24 Hours: 0.620M at 24°C 72 Hours: 0.919M at 25°C 96 Hours: 0.909M at 25°C

[|SAMS Sheet 5] - solubility in toluene: Vial 5 24 Hours: 0.714M at 24°C 72 Hours: 0.751M at 25°C =Discussion= The [|Solvent Selector] lists the predicted solubility values for trans-dibenzalacetone in each of these solvents using Model003 and Abraham Descriptors. =Conclusion= The solubility of trans-dibenzalacetone was measured to be 0.940M in benzene at room temperature. The solubility of trans-dibenzalacetone was measured to be 1.485M in THF at room temperature. The solubility of trans-dibenzalacetone was measured to be 0.027M in cyclohexane at room temperature. The solubility of trans-dibenzalacetone was measured to be 0.909M in cyclohexanone at room temperature. The solubility of trans-dibenzalacetone was measured to be 0.751M in toluene at room temperature. =Log=

2012-07-02
20:38 Added 0.1084 g of trans-dibenzalacetone (Product B from EXP307) into 1-dram screw cap Vial 1. 20:40 Added 0.1154 g of trans-dibenzalacetone into 1-dram screw cap Vial 2. 20:42 Added 0.0992 g of trans-dibenzalacetone into 1-dram screw cap Vial 3. 20:44 Added 0.1180 g of trans-dibenzalacetone into 1-dram screw cap Vial 4. 20:46 Added 0.1390 g of trans-dibenzalacetone into 1-dram screw cap Vial 5. 20:51 Added approximately 0.5 mL of benzene to Vial 1. 20:54 Added approximately 0.5 mL of tetrahydrofuran (THF) to Vial 2. 20:57 Added approximately 0.5 mL of cyclohexane to Vial 3. 20:59 Added approximately 0.5 mL of cyclohexanone to Vial 4. 21:01 Added approximately 0.5 mL of toluene to Vial 5. 21:04 Added an additional 0.0345 g of trans-dibenzalacetone to Vial 1. 21:07 Added an additional 0.0527 g of trans-dibenzalacetone to Vial 2. 21:10 Added an additional 0.1378 g of trans-dibenzalacetone to Vial 4. 21:13 Added an additional 0.1270 g of trans-dibenzalacetone to Vial 5. 21:16 Added an additional 0.0823 g of trans-dibenzalacetone to Vial 1. 21:18 Added an additional 0.0983 g of trans-dibenzalacetone to Vial 2. 21:21 Added an additional 0.0953 g of trans-dibenzalacetone to Vial 5. 21:25 Crystals were visible in each vial. Each vial was sealed with parafilm. Picture #1 was taken of each vial. The vials were secured on the shake plate standing vertically and the shake plate was turned on. =2012-07-03= 11:45 Removed the vials from the shake plate. Crystals were easily visible in vials 3 and 5. The vials were allowed to sit at room temperature (lab temperature was 24°C). 12:54 A few drops of the supernatant from Vial 3 was placed in an inner coaxial tube. 12:58 The outer NMR tube was filled with CDCl3. 13:02 The coaxial tube was placed into NMR Tube 3 containing the CDCl3. This supernatant from Vial 3 (solubility in cyclohexane) was analyzed by 500MHz HNMR. The file of the spectrum was saved as ONSEXP308Vial3. 13:56 A very small amount of crystals were barely visible in Vials 1,2,3 and 4. 14:11 Transferred a few drops of the supernatant from Vial 1 into NMR Tube 1 (used a coaxial tube). 14:18 Transferred a few drops of the supernatant from Vial 2 into NMR Tube 2 (used a coaxial tube). 14:23 Transferred a few drops of the supernatant from Vial 4 into NMR Tube 4 (used a coaxial tube). 14:28 Transferred a few drops of the supernatant from Vial 5 into NMR Tube 5 (used a coaxial tube). 14:30 Each of the samples was analyzed by 500MHz HNMR in an outer tube holding CDCl3. The files of the spectrums were saved as ONSEXP308Vial1, ONSEXP308Vial2, ONSEXP308Vial4 and ONSEXP308Vial5. 15:26 0.0686 g of the crystals were added to Vial 1. 15:30 0.0528 g of the crystals were added to Vial 2. 15:34 0.1005 g of the crystals were added to Vial 4. 15:36 0.0205 g of the crystals were added to Vial 5. 16:10 Crystals were clearly visible in each vial. The vials were sealed with parafilm and secured vertically on the shake plate. The shake plate was then turned on.

2012-07-05
10:48 The vials had fallen forward slightly on the shake plate, but were still upright. 11:04 The vials were removed from the shake plate. Crystals were visible in each of the five vials. The vials were allowed to sit on the counter to cool to room temperature (lab temperature was 25°C). 12:55 Took Picture #2 of the five vials. 12:59 Crystals were visible in each vial. 13:03 Filled the inner coaxial NMR Tube 1 with the supernatant from Vial 1. 13:08 Filled the inner coaxial NMR Tube 2 with the supernatant from Vial 2. 13:13 Filled the inner coaxial NMR Tube 3 with the supernatant from Vial 3. 13:19 Filled the inner coaxial NMR Tube 4 with the supernatant from Vial 4. 13:25 Filled the inner coaxial NMR Tube 5 with the supernatant from Vial 5. 17:00 Each of the samples was analyzed by 500MHz HNMR in an outer thin-walled NMR tube holding CDCl3. The files of the spectrums were saved as ONSEXP308Vial1_72hours, ONSEXP308Vial2_72hours, ONSEXP308Vial3_72hours, ONSEXP308Vial4_72hours, and ONSEXP308Vial5_72hours. 18:18 Vials 2 and 4 were sealed with parafilm and secured in a vertical position on the shake plate. The shake plate was then turned on.

2012-07-06
10:48 Removed Vials 2 and 4 from the shake plate. Crystals were visible in each vial and the vials were placed on the lab counter to cool to room temperature (lab temperature was (25°C). 13:26 Filled the inner coaxial NMR Tube 1 with the supernatant from Vial 2. 13:31 Filled the inner coaxial NMR Tube 2 with the supernatant from Vial 4. 15:24 Each of the samples was analyzed by 500MHz HNMR in an outer thin-walled NMR tube holding CDCl3. The files of the spectrums were saved as ONSEXP308Vial2_96hours and ONSEXP308Vial4_96hours.