EXP270

=Researcher= Stephanie Costa

=Objective=

To determine the solubility of [|cinnamic acid] in [|ethylene glycol] and [|1,2 propanediol] at 25C. The additivity of the volumes is [|assumptive].

=Procedure=

A test tube containing cinnamic acid and ethylene glycol (1) and anther containing cinnamic acid and propanediol (2) were heated and then cooled to room temperature. Using the NMR method, the solubilities were found.

=Results= [|Calculations sheet] [|NMR sheet]

The samples were zeroed using TMS

NMR A

In the sample 1A TMS peak was seen at 0ppm. Ethylene glycol peak was seen at 3.703ppm The cinnamic acid peaks were seen at 7.402 and 7.542ppm. Coupling was seen at two doublets: peaks 1 (6.415 and 6.447ppm) and peaks 2 (7.707 and 7.739ppm). The distance between the peaks was 16Hz. The CDCl3 peak was seen at 7.275 ppm.

In the sample 2A TMS peak was seen at 0ppm. The propanediol peak was at 1.134ppm. The cinnamic acid peak was at 7.529. Coupling was seen at two doublets: peaks 1 (6.409 and 6.442ppm) and peaks 2 (7.680 and 7.711ppm). The distance between the peaks was 16Hz. The CDCl3 peak was seen at 7.395ppm.

NMR B

In the sample 1B TMS peak was seen at 0ppm Ethylene glycol peak was seen at 3.705ppm Coupling for cinnamic acid was seen: peaks 1 (6.416 and 6.448ppm) and peaks 2 (7.710 and 7.742ppm). The peak distance was 16Hz. CDCl3 peak was seen at 7.274ppm.

In sample 2B TMS peak was seen at 0ppm. The propanediol peak was at 1.120ppm cinnamic acid peak was seen at 7.530ppm Coupling for cinnamic acid was seen: peaks 1 (6.394 and 6.426ppm) and peaks 2 (7.665 and 7.697ppm). The peak distance was 16Hz. CDCl3 peak was seen at 7.382ppm.

=Discussion= NMR A The ethylene glycol peak can not accurately be determine because a small broad peak was seen at the base of the ethylene glycol peak. This peak may be due to an impurity or bad spectra. An NMR of pure ethylene glycol will be taken at a later date to determine the cause of this unknown peak.

NMR B The ethylene glycol peak can not accurately be determined due to a broad peak at the base of the ethylene glycol peak. The solubility of propanediol was unable to be determined becase there was no precipitate.

=Conclusion= NMR A and B The solubility of cinnamic acid in ethylene glycol can not be accurately measured because an unknown peak was seen at the base of the ethylene glycol peak. The solubility of propanediol was unable to be determined because there was no precipitate present.

=Log=

2012-03-12
12:29- a hot water bath was started, the temperature was 22C. 12:31- .6537g of cinnamic acid was weighed out and added into a 20mL test tube labeled 1 12:36- the hot water bath was 31C, the room temperature bath was 19C 12:54- .6927g cinnamic acid was added to test tube 2 12:59- about 15mL ethylene glycol was added to test tube 1, parafilm was wrapped around the cap and the tube was inverted. The hot water bath was 60C and was turned down to a lower temperature. 13:10- about 15mL propanediol was added to test tube 2, parafilm was wrapped around the cap and the tube was inverted. teh hot water bath was 58C 13:11- the test tubes were placed into the hot water bath, which was 58C 13:20- the hot water bath was 58C. solute was seen in both test tubes. the tubes were inverted multiple times 13:23- the room temperature bath was 19C and was adjusted with warm water 12:25- the room temperature bath was 22C. 13:27- the hot water bath was 58.5C. solute was seen in both tubes. both tubes were inverted twenty times 13:33- the hot water bath was 58.5C. the room temperature bath was 22C and was adjusted with warm water. solute was seen in both tubes. 13:40- the test tubes were inverted five times. solute was seen in both tubes. the hot water bath was 58C. the room temperature bath was 24C and was adjusted with warm water. 13:45- the room temperature bath was 25C. the hot water bath was 58C and was turned off. solute was seen in both tubes. 13:50- the supernatants of both test tubes were poured off and the tubes were relabeled and parafilm was placed around the caps 13:55- the test tubes were palced in a room temperature bath (25C)

2012-3-19
10:57- no precipitate was seen in either samples. The room temperature bath was 22C. a hot water bath was started (22C). 11:00- the samples were sonicated for 30 seconds. No precipitate was seen. The hot water bath was 55C. 11:07- the samples were sonicated for 5 minutes and no precipitation was seen. 11:14- .5 mL of each solution was placed into a vial for the NMR 11:19- .4193g of cinnamic acid was added to test tube 1. Parafilm was stretched around the cap and the sample was inverted. 11:25- .4158g of cinnamic acid was added to test tube 2. Paraflim was stretched around the cap and the sample was inverted. 11:28- the hot water bath was 65C 11:33- the test tubes were placed in the hot water bath (65C). 11:47- a little less than 1mL of CDCl3 was added to each vial and the solutions were mixed. The solutions were then placed into the NMR tubes 11:56- the test tubes were inverted and replaced into the 65C bath 12:06- a NMR was run on sample 1. A 500 Hz NMR machine was used. The sample was saved as ONSCEXP270-1A_ethyleneglycolandcinnamicacid_scosta.dx. 12:25- the second sample was run on the NMR and saved as ONSCEXP270-2A_propanediolandcinnamicacid_scosta.dx. 12:43- the test tubes were inverted. The hot water bath was 65C 12:49- the hot water bath (65C) was turned off. The test tubes were left to rest in room temperature (22.5C). Parafilm melted at 65C in the hot water bath. No solute was seen in either of the samples

2012-4-13
10:58- precipitate was seen in sample 1. no precipitate was seen in sample 2. 11:01- about.5 mL of sample 1 was placed into a vial (1) 11:04- a little less than 1mL of CDCl3 was added to vial 1, where it was mixed and transferred into an NMR tube. 11:10- about.5 mL of sample 2 was placed into a vial (2). less than 1mL of CDCl3 was added to vial 1, where it was mixed and transferred into another NMR tube 13:26- An NMR of sample 2 was taken using the 500 NMR. The results were saved as "ONSCEXP270-2B_NMR1_propandieolandcinnamicacid_scosta.dx" 13:43- An NMR of sample 1 was taken using the 500 NMR. The results were saved as "ONSCEXP270-1B_NMR1_cinnamicacidandcinnamicacid_scosta.dx"