Objective

To ascertain the solubility of octylamine Chemspider, cyclohexylamine Chemspider, benzylamine Chemspider, aniline Chemspider, and o-chloroaniline Chemspider in methanol Chemspider.


Procedure

A solution of octylamine in methanol was prepared by addition of octylamine drop-wise, using a Pasteur pipette, to a one dram vial charged with 300μl of methanol. Also, a solution of methanol in octylamine was prepared by adding methanol drop-wise, using a Pastuer pipette, to a one dram vial charged with 300μl of octylamine.
A solution of cyclohexylamine in methanol was prepared by addition of cyclohexylamine drop-wise, using a Pastuer pipette, to a one dram vial charged with 300μl of methanol. Also, a solution of methanol in cyclohexylamine was prepared by adding methanol drop-wise, using a Pastuer pipette, to a one dram vial charged with 300μl of cyclohexylamine.
A solution of benzylamine in methanol was prepared by addition of benzylamine drop-wise, using a Pastuer pipette, to a one dram vial charged with 300μl of methanol. Also, a solution of methanol in benzylamine was prepared by adding methanol drop-wise, using a Pasteur pipette, to a one dram vial charged with 300μl of benzylamine.
A solution of aniline in methanol was prepared by addition of aniline drop-wise, using a Pasteur pipette, to a one dram vial charge with 300μl of methanol. Also, a solution of methanol in aniline was prepared by adding methanol drop-wise, using a Pasteur pipette, to a one dram vial charged with 300μl of aniline.
A solution of o-chloroaniline in methanol was prepared by addition of o-chloroaniline drop-wise, using a Pasteur pipette, to a one dram vial charged with 300μl of methanol. Also, a solution of methanol in o-chloroaniline was prepared by adding methanol drop-wise, using a Pasteur pipette, to a one dram vial charged with 300μl of o-chloroaniline.
Brief stints of swirling were used during the make-up of octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline so that their miscibility in methanol and methanol in each component could be visually confirmed; and the concentration of pure components could be taken as that of its saturated solution in methanol.


Observation

Use care when micropipetting methanol, perhaps due to its relative high weight to density [The italicized phrase is unclear to me -- please explain. (I think perhaps you are talking about density vs viscosity...?) Can you think of an alternative mechanism to explain the "leakage"?-BH], the solvent begins to "leak" out of the pipette tip.

Addition of droplets of octylamine to methanol produced an oil-like appearance as it mixed in. No visible layers were seen in vials "A" or "B".

Addition of cyclohexylamine to methanol in vial "C" produced no visible layers, solution went from a light brown color (1-5 droplets) to dark brown in appearance. The addition of methanol to vial "D" containing cyclohexylamine saw a slight reversal in color progression, however the solution remained a brown color (was not light brown). No layers formed in vial "D".

Adding benzylamine to vial "E" turned the solution of methanol from clear to a yellowish tint. Vial "F" progressed from a slight yellow to a clearish hue with a bit of yellow. Both vials had no layer formations.

Adding aniline to vial "G" turned to clear methanol to a yellow (1-7 drops) and finally to a golden color (Use care aniline leaks out of micropipette quickly). In vial "H", the addition of approximately 1mL of methanol turned the solution from a slight gold to a clear with a hint of color.

Vial "I" was filled with methanol and the addition of o-chloroaniline transformed the solution from a clear to a hazel color with a few droplets. Finally, the solution progressed to a bronze/brown. Adding approximately 1mL methanol to the vial "J", filled with 300μl of o-chloroaniline, produced a layer in which methanol was found on top of the o-chloroaniline. However, this was a result of the methanol being less dense than the o-chloroaniline and with some swirling the solution mixed in together. The color of the solution progressed from a bronze to a peach/hazel color. No layers were seen in either vials after swirling.



Discussion

When determining the solubility of a liquid solute in a liquid solvent, saturation can be easily observed by the viewing of the separation of components in differing layers. During the addition of octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline into methanol yielded no separation into layers at anytime (even after swirling and allowing the components to settle). Furthermore, the use of a different combination of analysis (methanol into octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline) yielded the same results.
The concentration of the separate saturated solutions of octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline in methanol were similar to each solute in their pure forms; which can be defined using their densities 0.782 g/mL (Source), 0.867g/mL (Source), 0.981 g/mL (Source), 1.022 g/mL (Source), and 1.213 g/mL (Source) respectively. This is rationalized given the observation that all proportions of octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline were soluble in methanol and that no matter the extent of volume of octylamine, cyclohexylamine, benzylamine, aniline, or o-chloroaniline added, the volume of methanol in the solution would henceforth be neglible. Therefore, the concentrations of pure octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline can be looked as the concentration of their saturated solutions in methanol; which were calculated to be 6.05M, 8.74M, 9.16M, 10.97M, and 9.509M, respectively at room temperature.

Conclusion

Octylamine, cyclohexylamine, benzylamine, aniline, and o-chloroaniline are all completely miscible in a methanol solvent.

Results

Exp029.jpg
Octylamine.jpg Cyclohexylamine.jpg Benzylamine.jpg Aniline.jpg o-chloroaniline.jpg

Spreadsheet

Log

2009-1-17

14:38 Using a micropipette, 300μl of methanol were added to the one dram vials "A, C, E, G, & I" and afterward they were capped.
14:43 Approximately 1mL of octylamine was added drop-wise to vial "A" using a Pasteur pipette.
14:46 Vial "A" was briefly swirled.
14:48 300μl of octylamine was added to vial "B".
14.49 Approximately 1mL of methanol was added drop-wise to vial "B".
14:52 Approximately 1mL of cyclohexylamine was added to vial "C".
14:56 300
μl of cyclohexylamine was added to vial "D"
15:02 Approximately 1mL of benzylamine was added to vial "E".
15:05 Vials "A-D" were swirled. No visible layers occurred.
15:06 Added 300μl of benzylamine to vial "F".
15:06 Added approximately 1mL of methanol drop-wise to vial "F".
15:09 Swirled vial "F". No visible layers.
15:10 Added approximately 1mL of aniline to vial "G".
15:13 Swirled vial "G". No visible layers.
15:14 Add 300μl of aniline to vial "
H".
15:15 Approximately 1mL of methanol was added to vial "H".
15:17 Added approximately 1mL of o-chloroaniline to vial "I".
15:19 Briefly swirled vial "I". No visible layers formed.
15:21 Swirled vials "E-H". No observed layers formed.
15:22 300μl of o-chloroaniline added to vial "J".
15:24 Approximately 1mL of methanol added to vial "J" drop-wise.
15:26 Swirled vial "J". No observed layers formed.
15:32 Photos of experiment were taken.


Tags


Compound
Inchi Key
Inchi
Octylamine
IOQPZZOEVPZRBK-UHFFFAOYAR
InChI=1/C8H19N/c1-2-3-4-5-6-7-8-9/h2-9H2,1H3
Cyclohexylamine
PAFZNILMFXTMIY-UHFFFAOYAP
InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
Benzylamine
WGQKYBSKWIADBV-UHFFFAOYAL
InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
Aniline
PAYRUJLWNCNPSJ-UHFFFAOYAP
InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
o-chloroaniline
AKCRQHGQIJBRMN-UHFFFAOYAL
InChI=1/C6H6ClN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2
Methanol
OKKJLVBELUTLKV-UHFFFAOYAX
InChI=1/CH4O/c1-2/h2H,1H3