| Wednesday and Thursday research |
[Dec. 10th, 2006|05:00 am] |
I removed the solvent of the azine we made. Because I wasn't trained to run the NMR machine, I had to give the sample to the grad student and he ran it on Friday. I did not go into the lab on Friday, so I do not know how it goes. I will find out about it on Monday.
Aside from that, the phenyl phosphine we ordered from China has finally arrived. We then set up the reaction of this phenyl phosphine with the hydrazine monohydrate under Nitrogen. The phosphine smells really bad. The box it came with even smell really bad too. I wish all of you can smell it too, so that you all know how bad it is. After adding them together, I left the reaction to run overnight. Over the weekend, I am working on the poster for the poster session on Monday. I'm looking forward to see everyone's. |
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| Update on my research |
[Dec. 6th, 2006|01:21 am] |
So, last week and this week I tried to run the reaction again. As I said before my research is looking at synthesis of 3,4-diazaphospholanes using two different routes. The first route was to react a primary phosphine with aqueous formaldehyde, followed by hydrazine. The second approach was to make an azine from an aldehyde and hydrazine before reacting it with a primary phosphine.
The first path failed because instead of producing 3,4-diazaphospholane, we got two-five membered rings of phospholane based on NMR spectra. We couldn’t try this reaction again as we are out of the reagent and it is still on its way from China (I believe). It’s been three weeks now. Because of that, I ran the reaction as shown in the second path. However, before running the reaction itself, I had to purify the isobutyraldehyde by distillation because the chemical looked really old and NMR taken shows a lot of impurities. After running the reaction overnight, the intermediary product was obtained, but again there are some impurities. Therefore, I had to run a column to purify it before reacting it again.
Today, I ran the column and took 52 fractions. Based on previous column experience, I found that there are three different products (two of which are unwanted) eluting from the column. That’s why I collected that many fractions. Tomorrow, we will run the NMR and hopefully it will be pure enough that I can proceed to the next step, reacting the intermediary product further to make 3,4-diazaphospholane, I hope. |
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| Research Continuation |
[Nov. 25th, 2006|03:24 pm] |
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So, we found out that neither of the NMR shows a strong present of the product we desired. There were still a lot of impurities and thus, we decided to purify the isobutyraldehyde we are using by simple distillation on Wednesday. Because of the break, I haven't been able to go into the lab yet. However, when I go in on Monday, we should be able to re-do the reaction with a purer reactant.... Time really flies!! |
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| Independent Research |
[Nov. 17th, 2006|03:33 am] |
Since the last time I posted, I have done many things. First, I reacted the product I got from the first reaction (cyclohexylphosphine and formaldehyde) with hydrazine. We were hoping to get 3,4-diazaphospholane by adding the hydrazine dropwise. The method was proposed to avoid a further hydrolysis of the hydrogen from nitrogen, which was the result of the paper from which the reaction is based on. Upon taking the mass spec of the product, however, we found that the unwanted product was still made instead of the 3,4-diazaphospholane.
Because of that, we tried another route of using chiral aldehyde. In this case, we chose isobutyraldehyde and reacted it with hydrazine. The solvent used for the reaction is ethanol and the reaction was stirred overnight. Then, the solvent was removed using a rotary evaporator and an NMR spec was taken. The NMR spec shows that there are a lot of impurities in the product that we made. So, today I ran a column to purify the product using DCM as the solvent. It was found using TLC that there are 2 compounds present in the product. Running the column resulted in the separation of the two product and fractions were collected (I collected a total of 47 fractions!!!). Solvent will be rotavaped tomorrow and we will see how the NMR spec looks like this time to determine which of the two compounds is the product. |
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| Independent Research Lab |
[Nov. 7th, 2006|01:42 am] |
So, for the second part of this class I am working in the Landis group. My project is a small part of a bigger project, which is Asymmetric Hydroformylation of Enamides. The objective of the project is to make 3,4-diazaphospholane ligands that are enantioselective.
So, I've been to the lab twice so far and it has been really interesting. All of the reactions that I am running have to be oxygen free and I have been shown around on how to deal with this. We have this big bad where things are put under nitrogen gas and if I need to get something out of it there are quite a number of steps to avoid the contamination of oxygen.
Last Monday, I started the first reaction. Cyclohexylphosphine was reacted with formaldehyde in ethanol solvent. The reaction was left overnight and actually once everything's added, the reaction can be left unattended. Most of the works come from setting up. First I had to degass all the reactants and reaction glassware. Everything went pretty well and I am psyched to go back into the lab tomorrow to continue working on my project. More updates on tomorrow's lab will come shortly. |
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| Catalyst Synthess and Enantioselective Epoxidation |
[Oct. 29th, 2006|04:12 pm] |
Last Monday, we inserted the metal to our Jacobsen ligand and everything went pretty smoothly. We were supposed to use polarimeter to check the optical rotation of our ligand, but it was broken. As a result, we had to skip it. The melting point of the catalyst was found to be 342 degrees. It was a little higher in comparison to the reference melting point.
Then, on Wednesday, we did the enantioselective epoxidation with the catalyst we made earlier. I used styrene as the alkene and the reaction proceeded faster than I had expected. The procedure said the reaction would be completed in two hours, but my reactants were all gone in under an hour as checked by TLC. Then the epoxide was filtered and it was saved for Monday to be purified by flash column chromatography. |
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| Ligand Synthesis - (R,R)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine |
[Oct. 22nd, 2006|02:36 pm] |
That's a very long name. Let's just refer it as the Jacobsen Ligand. So, last Wednesday we synthesized our Jacobsen ligand. Everything went smoothly and we obtained the yellow solid. The melting point of the product was found to be 197 degrees C, which is only 3 degrees lower than the reference melting point of 200 degrees C. The experience at the lab on Wednesday was quite satisfying because we did not screw up. That gave me such a relief!
Also on Wednesday, all of us who are taking the 2nd credit option got assigned to the professor whom we will be working for on the special project thing. I emailed the professor and have yet to receive a reply. To be honest, I am kind of nervous about what to expect and what kind of project will I be getting. I guess, I won't know until he gets back to me.
Anyway, tomorrow we will check the polarizability of our Jacobsen ligand and then insert Mn into it to make our catalyst. Seems like it will be a long lab period because we are required to heat things up several times for either 30 minutes or 1 hour. Hope things will go well. |
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| Interesting Natural Product |
[Oct. 18th, 2006|01:59 am] |
I like spicy food and I found that the active component in chili pepper that produces the burning sensation is a type of organic compound - Capsaicin (8-Methyl-N-vanillyl-6-nonenamide).
This molecule is non polar and therefore, drinking water to reduce the burning sensation is actually ineffective. The reason for this is because capsaicin is unable to dissolve water, so instead it spread the burning across the surface of mouth.
Another interesting thing about capsaicin is that it can be used to temporarily relieve minor aches and pain of muscles and joins. Capsaicin can also be used to deter pest. So, from now on, eat more of those HOT chili pepper.. =) |
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| End of Piperine Purification and Start of Epoxidation |
[Oct. 18th, 2006|12:52 am] |
So, isolating nnd purifying of the piperine from black pepper was not really that bad. It's worse, especially when I had to redo my column because I didn't pack it properly. It was frustrating, but I finally got it to work and I am quite proud of my accomplishment. Thanks to Teshik and Chris who had been helping me throughout the lab. Now, I should be able to run a similar column better =)
Anyway, last Monday we started the epoxidation reaction. Everything went fine. I hope it'll be this way for the rest of the experiment. I wish! |
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| Synthesis of Piperine |
[Oct. 8th, 2006|01:41 pm] |
So, on Wednesday we continued the synthesis of piperine after it was being refluxed for 40 hours. Turned out, it was not very hot after all. The precipitate that was first collected was a yellow solid instead of beige powder as obtained by the other two groups. When we tried to recystallize it, no crystal was formed. We tried rotavaporized it and re-added the ethyl acetate + hexane. No such luck. So, we put a parafilm on the flask and we will see what happens tomorrow. Unsuccessful synthesis can be quite frustrating. I really don't know what to say and can't really think of what errors have been done in this process.
Anyway, I'll just have to wait until tomorrow. Plus, tomorrow we will isolate piperine from ground black pepper, which should be interesting. |
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| Recrystallization of methyl piperate and Synthesis of Piperine |
[Oct. 2nd, 2006|11:00 pm] |
Today we took the methyl piperate made on Wednesday from the fridge. The mixture was poured into cold water and then stirred for 45 minutes. In between, we had a lecture on SciFinder and RefWork. I think both are really cool and they will definitely help me out in writing the second lab report. I actually had similar tutorial on them this past summer when I took CBE 424, but I don't remember how to use them especially that we only have 7 licenses to get into SciFinder.
Back to the lab, we filtrated the solid formed and then did recrystallization of the solid from ethyl acetate. We obtained light yellow crystals and upon weighing, the product was 1.506 grams. I am quite happy with the yield even though the amount is still less than 3.5 grams for the next step. Because we didn't obtain as much methyl piperate as we wanted, we had to scale down the amount of the other reagents. Currently, sodium methoxide, methyl piperate and distilled piperidine are being refluxed for 40 hours until Wednesday. Hopefully, it goes well.
For the next lab period we will continue on the piperine synthesis as well as isolating piperine from ground black pepper. Sounds interesting eh? |
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| Synthesis of Methyl Piperate |
[Sep. 28th, 2006|12:26 am] |
In the lecture before the lab today, we went over a sample of lab report on sulfanilamide from last semester and we discussed about it. Basically, we talked about the good things as well as the bad things of the report. We were really critical about it and I felt really bad somehow. After the discussion, I felt like going back into my report and starting to scratch + add things here and there. Maybe it's just me. The discussion did help me to understand more on how to write a good report. I can only hope that I can write better on the next lab report.
Meanwhile in the lab today, we synthesized methyl piperate from different chemicals, including methyl 4-(diethoxyphosphinyl)-2-butenoate made from the previous lab period. The reaction was kind of cool, especially that we made sodium methoxide solution initially. We started from sodium metal and placed it in methanol. When methanol was added, bubble started to form, showing that hydrogen gas was produced. It was also very exothermic because the flask felt warm when it was touched. After that, we added this solution drop wise to the product we made from last period, piperonal, and dimethoxyethane. The color of the solution turned brown and it got darker as more sodium methoxide was added.
Then.. we left it stirred and we were done. It was 3 pm and it felt nice to leave the lab early for the second time this week. Chris said that he was going to check our mixtures after 2 hours and store them in the refrigerator for us. So, thanks Chris!
Anyway, that's all for now. Next week we're going to synthesize piperine and it should be exciting. |
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| Synthesis of Methyl 4-(diethoxyphosphinyl)-2-butenoate |
[Sep. 27th, 2006|07:02 am] |
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So, on Monday we started the first step of experiment #2. At the end of the whole experiment, we're going to synthesize a natural product called piperine, usually found in black pepper. The first step that we did was to synthesize methyl 4-(diethoxyphosphinyl)-2-butenoate by adding methyl 4-bromo-2-butenoate and triethylphospite. Then, we distilled ethyl bromide and save the rest of the crude product. Few thoughts on Monday. We finished the lab early on Monday and that really gave me time to do other things like writing the report for experiment #1. We also had a lecture on natural product and it just amazed me looking at all the structure of these products. Finally, we did this lab in the fume hood because of the toxicity of ethyl bromide and the stench of triethylphosphite. It was interesting to see how the whole class squeezed into one corner where the fume hood was. To be honest, the distillate did smell really bad. I could still smell the odor although it was placed in the fume hood. I guess that's all about this lab. On Wednesday we will synthesize methyl piperate and we will see how it goes. |
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| Synthesis of Sulfanilamide |
[Sep. 22nd, 2006|04:09 pm] |
Wednesday was the last day for the first experiment. I think all of us managed to synthesize of sulfanilamide. The final product looked really cool with metallic shiny color. Overall, I feel that I am starting to get a hang of working in an organic lab. At the beginning, I really did not feel comfortable with equipments, IR, and NMR spectrum because I have not dealt with O-chem for the past three years. So, it's been a while. Now, slowly I start to gain more confidence.
The only thing that concern me right now is the lab report that's due next Wednesday. I will try to write a draft over the weekend and see how it goes from there.
Also, next week we will do a synthesis of piperine. I am quite excited about that. We'll see how it goes next week. Alright, I hope everyone has a good weekend. |
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| Synthesis of 4-Acetamidobenzenesulfonyl Chloride and 4-Acetamidobenzenesulfonamide |
[Sep. 19th, 2006|09:42 pm] |
So, the last product (acetanilide) we thought we recovered was not acetanilide. Apparently, everyone in the lab did not realize that the HCl solution had to be diluted. As a result, noone had the right product. That made it two in a row for me and my partner! I guess, mistakes do happen and we just need to learn from them.
Anyway, yesterday we did two synthesis. The first was 4-acetamidobenzenesulfonyl chloride and the second was 4-acetamidobenzenesulfonamide. I think it went well and we dealt with the most dangerous chemical so far in this class: chlorosulfonic acid. I believe we did obtain the right product this time after using the anilide from both the other section and Sigma. We ran NMR for our product, so I hope it will turn out fine. Tomorrow's the last day for the first experiment and the first lab report is due a week after. Fun!
Alright, more to come people... |
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| Synthesis of Acetanilide |
[Sep. 13th, 2006|09:01 pm] |
Second day of lab went relatively well. We synthesized acetanilide from aniline. Since we didn't get aniline from previous lab, we used the commercially available aniline provided. I believe, we obtained the right product although the amount recovered seems pretty small. We were also introduced to the software called NUTS for our NMR data. It was confusing at first, but I hope I will get a hang of it once I get to use it more often.
Alright people, I will post more updates next week. |
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| Synthesis of Sulfanilamide - First day |
[Sep. 11th, 2006|09:26 pm] |
Today was the first day for real experiment. The experiment was both exciting and frustating. It was exciting since I learned a new technique and recalled many of my laboratory techniques. The rotary evaporator we used to remove diethyl ether was very interesting. However, it was frustating to find out that upon rotating our product solidifed. It did not sound good eh? Well, we also recovered some-what seemed like- an organic solution through the condenser of this evaporator. Therefore, we put both samples in to be tested using NMR. Hopefully, one of them was aniline. I would really feel bad if none turned out to be aniline, especially after staying in the lab until almost 6 pm. It has been a really long day for me!
Hopefully good news will come on Wednesday. |
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| Introduction - About Me |
[Sep. 7th, 2006|02:49 pm] |
Hello Chem 346 bloggers,
I have never blogged before, so let's see how well I describe myself.
My name is Chilwin Tanamal and I am a senior in Chemical Engineering and Business Certificate. I am actually graduating this December and am very excited about this. I have always enjoyed chemistry classes since high school and this is the my reason for taking this class to fulfill my advanced chemistry lab elective. I hope that I can learn as many things as possible about synthesis from this lab.
My plan upon graduation is to work in industry, most likely in the R&D department.
Well, I think that this should be enough as an introduction. Thank you for stopping by and I will see many of you in class. Please keep checking back as I will update this weblog after every experiment I do throughout the semester.
Adios! |
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