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Author: Subject: Competition — Lab from five OTC items
hyfalcon
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[*] posted on 13-4-2016 at 04:09


That final step sounds like fun in and of itself. I hate working with ether and combining those chemicals in it just sounds like an explosion waiting to happen.
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[*] posted on 15-4-2016 at 18:42


Well, it is time to look at some results and announce the winner.

Only one formal submission was made and so I hereby declare Volanschemia to be winner of this competition. Congratulations and enjoy your prize. You deserve it. I am in the process of organising the account credit with Onyxmet and will U2U you when the money is ready to spend.

A big thanks to all who participated – even if it was only to float a few ideas around and send a couple of U2Us. I have some thoughts about what has been learned through this exercise but that can wait for a follow-up post. What I want to do here is to give the details of Volanschemia’s entry and what impressed me about it.

First, the entry can be read here:
Attachment: Lab from 5 OTC Products - Volanschemia.pdf (1.8MB)
This file has been downloaded 846 times

Write-up
I thought this was well presented. Lovely clear procedures written up with great photos of equipment setup. Attention is given to safety considerations relevant supporting theory and limitations and possible improvements to the procedures. I think this is a rather nice document that someone could easily follow to get a good basic introduction to organic syntheses.

Conformation to the rules and the spirit of the competition
Astute readers may note a couple of occasions where Volanschemia used reagents not derived from his five OOTC products. He actually checked with me on each occasion – the key thing being that none of these made their way into the final product. I treated them as extraction agents and lab disposables. Given that none of them were particularly esoteric reagents and that in each case there were a variety of commonly-used suitable substitutes I think it was perfectly acceptable.
As far as the spirit of the competition goes, I think this was embraced wholeheartedly. The products obtained are both interesting and useful. The procedures are standard but there is some variety there and it serves as a pretty good introduction to OC I think.
In keeping with the instructions, some procedures were not actually performed but suitable reference was given to them.

Products obtained
There was a good range here. I like the IUPAC nomenclature but I will list them by more common names:
  • Potassium phthalate
  • Phthalic acid
  • Phthalic anhydride
  • Manganese dioxide
  • Acetyl salicylic acid
  • Salicylic acid
  • Phenol
  • Phenolphthalein
  • Ethyl salicylate
  • Ethyl acetate
  • Diethyl ether
  • Acetylaldehyde
  • Acetic acid
  • Manganese heptoxide


Yields
Yields were not always great, but that I think is one of the compromises of the competition setup.
In every case however, enough product was obtained in sufficient purity to demonstrate the effectiveness of the procedure. Therefore this submission demonstrates the procedures well. In some cases, even though the product yield may have been low, it was demonstrated that a useful quantity of a lab reagent could be made through OTC sources. The usefulness of having some reagents should not be underestimated and the percentage yield is really a secondary consideration. (How much phenolphthalein do your really need anyway?)

Procedures Undertaken
From my own perspective, as one who has done little OC, this has been interesting. I admit to being something of an OC novice and that at the time when this comp was posed, most of these procedures were unfamiliar. A few months of watching Chemplayer, NileRed, Doug’s Lab and others have made a difference here and so while reading Volanschemia’s work, everything was reasonably familiar. Nice to be able to track my own progress. There are still a number of procedures that I have not done myself yet and so this will be a pretty good resource for my own practical learning.
Anyway, there is a range of techniques shown:
  • Oxidation to carboxylic acid
  • Oxidation to aldehyde
  • Acid extraction
  • Thermal decomposition to acid anhydride
  • Crystallisation via sublimation
  • Solvent extraction
  • Acid catalysed hydrolysis
  • Thermal decarboxylation
  • Fischer esterification (3)
  • Acid catalysed condensation
  • And whatever that reaction to produce M2O7 is called – acid dehydration I guess.


As well as these are the standard filtration, crystallisation, distillation that are normal parts of a work-up.
I think this represents a good variety of techniques and is actually suitable as a teaching sequence with few modifications. Overall, this is really impressive.

Of particular Note
I thought the production of phenolphthalein was worthy of special mention. It seems that this was one of the key target compounds and inspired much of what else transpired. Admittedly this is a tried and well-known route to the product but it was impressive to see it demonstrated nonetheless. What we have here is a multiple step synthesis involving several procedures and a number of (useful) intermediate compounds to result in a chemical of reasonable complexity. And phenolphthalein is such an important lab basic – it was really good to have its synthesis placed within reach of a competent home chemist.
I think there are a few such compounds that make for really good targets – luminol is another. They are challenging but doable for the amateur chemist and I think a lot can be learned by attempting them. Beginning with OTC items only adds to the sense of accomplishment. Something of a rite of passage or a notch in the belt I guess. If someone wants to get into amateur chemistry and asks where to start, I think it is possible to say, “Make some phenolphthalein” and learn everything you can along the way. And by the time you have done that you will have a good skill set and reasonable knowledge to attempt all kinds of things.

In Conclusion
I think that this represents a really good effort and fine presentation of a well-thought sequence of some really interesting and useful synths – perfectly in keeping with the competition. It is well deserving of a prize and would have taken some beating even if there had been other entries.
So, well done Volanschemia. Enjoy the spoils.

j_sum1.


Next post – some other thoughts on ideas mentioned and on home chemistry and competitions in general. But I need to take some time out to play with my kids.




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[*] posted on 15-4-2016 at 19:17


congrats to volanschemia




Beginning construction of periodic table display
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Volanschemia
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[*] posted on 15-4-2016 at 19:38


:D:D:D:D

First of all I'd like to deeply thank j_sum for conceiving and running this competition. It was a truly wonderful idea and I'm just disappointed that there weren't more entries. Thank you also for your feedback, it means a lot. I am quite proud that I managed to do it in 10 days as well, a holiday well spent I think. I can tell you though that it isn't pleasant when your lab smells of Wintergreen, Phenol, Phthalic Anhydride, Xylene, Ethanal and Ethanoic Acid all at the same time.

I'm glad you appreciated the use if systematic names j_sum, there aren't many who do I'm afraid. I am well known for being a bit of a stickler for them. To quote Albus Dumbledore: "Always use the proper name for things".

I did indeed first think up Phenolphthalein as my target compound, and the others were spawned from that. The step where I actually made Phenolphthalein was definitely the highlight because of the sense of accomplishment in getting there from Xylene and Potassium Permanganate.

Once again, thank you to j_sum and everyone else who helped to support the competition.

Now it's time to visit Onyxmet and have a look through their catalogue...




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[*] posted on 15-4-2016 at 19:52


Congratulations.
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[*] posted on 15-4-2016 at 20:08


Thanks JJay, I reckon you would have had me beat if not for the reactor failure, OTC Lithium Aluminium Hydride is definitely nothing to be sniffed at.

I look forward to reading your entry, partial or otherwise.




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[*] posted on 15-4-2016 at 20:30


I extend the congratulations! Excellent work. However, I must mention that the formation of phenolphthalein is actually a friedel-crafts reaction. I am very impressed you were able to form phthalic anhydride and use it in this reaction from mixed xylenes (did you get their composition from msds?) Some more rigorous referencing would be useful overall.
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[*] posted on 15-4-2016 at 20:37


Thank you HeYBrO!

I apologise for the error in terms there. I did reference the MSDS for the Xylenes in my writeup. It does not, however, specify the concentration of each individual isomer, only that it contains Xylenes.




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[*] posted on 15-4-2016 at 21:03


FC?
Well I have heard the term but have not done the research on it. I thought FC involved such species as anhydrous AlCl3. So, that's another to add to the list. Two Fischers and one Friedel Crafts.

Two obvious questions get opened up on the whole xylene thing
1. Is there a straightforward method to isolate or partially isolate isomers from a mixed xylene?
2. O-xylene is obviously very useful. What can be done with the other two?




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[*] posted on 15-4-2016 at 21:11


The only two methods I can think of to possibly effectively separate the isomers is freezing and column chromatography.

I think p-Xylene is the most useful isomer industrially because it is used to make plastics, m-Xylene being the least useful (and therefore the highest concentration in the paint stripper). I'm not sure about lab use, obviously p-Xylene can be used to make p-Phthalic Acid.




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[*] posted on 18-4-2016 at 02:27


Well, done and dusted -- almost.

This has been a really fun exercise for me. It would have been even better if more had been able to participate and make submissions But things are what they are. Volanschemia's work is really good and I will have some fun duplicating some of those procedures myself. (Scroll up a few posts if you missed it.) Phthalic anhydride might be an idea.

I have some thoughts on the whole competition process and, at the risk of boring some, I thought I might wax lyrical for a bit.

This won't be the last competition or challenge that I sponsor or get involved in. I really like the idea and the opportunity to coordinate with others and bounce ideas around. I think it is a great way of encouraging newcomers, of promoting new ideas and giving a bit of focus and direction to experimentation.

Getting philosophical now. Sometimes the most important thing to do is simply show up. I think there have been a couple of competitions with small turn-out. The odds get stacked greatly in favour of the ones who give things a try.

Which brings me to my main point... It seems that the hardest thing for hobby chemists to do is to get a stretch of quality time in the lab. It is harder than organising chemicals or equipment. And although we often complain about restrictions and regulations, the biggest hurdle we face is time. If you are anything like me, all manner of important and worthwhile things take precedence. Indeed, they must on occasions. Time with my family is more important than a nitric acid distillation. But there are some here who manage to tip the balance in the direction of getting actual stuff done in the lab and my hat goes off to you.

So a few specific tributes -- in no particular order. And please don't get offended if I miss someone from the list:
  • Volanschemia -- for getting off your chuff and doing what no one else was able to do this time around
  • Chemplayer, Nurdrage, Praxichys, NileRed, MrHomeScientist and others who not only get some chemistry done but are also able to periodically post some informative and educational stuff to YT
  • crystalgrower and hegi who seem to be doing a great job of making interesting crystals and taking high quality photos
  • Arkoma who manages to always have an interesting project on the go in his lab -- whether it is chickens, pecans or ethanol -- and isn't going too let anything stop him from pursuing his interest
  • Magpie for the range of gidgets an gadgets you make and tweak. Truly superb stuff. Thanks for sharing.
  • JJay for adding a range of quality posts to the everyday chemistry thread.
  • Bluamine - You will get white phos one day -- if it does not get you first. Stay safe. Thanks for posting your progress.
  • ave369. It is always interesting to read from someone who is culturally far removed from me. I love what you are able to make in a small (and often crazy-looking) space with simple reagents and limited equipment. I'm inspired.
  • blogfast and woelen. Even when you can't get practical time in the lab you are so generous with your knowledge and your time to answer the often dumb questions that we frequently raise.
  • there are dozens more -- everyone who actually gets something done and shares their findings

A big thank you to all of you. I have learned a lot from what you have shared. This competition was a small effort to give something back. ll going well I will be able to contribute something of a chemistry nature myself. (My last effort kind of failed -- I need to engineer something different to get it to work. I have not given up yet though.)

So, if you have not done so yet, take a look at Volnschemia's submission and see what can be done in 10 days. It's pretty cool. :cool:

J.




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[*] posted on 6-6-2016 at 12:00


Just poppin in to say that I was following this contest before I got an account and even though there was only one official entry there was a lot of excellent conversation about the topic. I think its an interesting restriction of 5 otc items. I would love to see some more contests like this that beginning amateurs such as myself could partake in and learn from.

Hope there is another one soon! I probably wont win seeing the experience a lot of you have but I would definitely participate.
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[*] posted on 6-6-2016 at 14:43


Thanks for that pepe.
Yeah, I too would like to see more competitions and more participation in competitions. I will definitely do another at some stage. But probably not for some time. My lab is out of action while I sell house and buy another. Life is unusually busy atm.



(Come to think of it, I haven't finished my final attempt at aga's HNO3 competition. I would still like to complete that: I still have my marinated lentils around. But in the process of moving I will probably have to discard the equipment I built from junk and can't see it resurrecting at my new place.)




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[*] posted on 29-6-2016 at 23:45


j_sum, I seem to remember you mentioning something about a U2U from MolecularWorld where he rattled off some 55 compounds. I was wondering if you were planning on posting it here for the benefit of others?

I for one would definitely be interested in having a look.

On a different note, something I forgot to mention a few months ago is that if anyone else attempts anything from my writeup and feels like reporting how they went, I would love to know how you went. I'm looking for improvements, anomalies, failures, the works!

For instance, I know that aga tried out the oxidation of Xylenes recently, have you done anything else with that aga?

[Edited on 30-6-2016 by Volanschemia]




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[*] posted on 30-6-2016 at 00:04


Good question, volanschemia. MW specified quite explicitly that his ideas were not an entry and so I decided not to post them. I can U2U you the details when I am not on my phone.



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[*] posted on 30-6-2016 at 00:08


That would be great j_sum, thanks.



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[*] posted on 17-8-2016 at 19:50


this is really fascinating, not sure I am following but I will have plenty of homework
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[*] posted on 17-8-2016 at 21:02


Competition finished some time ago Sparrowpatch.

I have an idea for another competition but it will have to wait until I build my lab -- which, I am afraid, is a long-term project.




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[*] posted on 18-8-2016 at 06:49


Quote: Originally posted by woelen  
I put this thread on top, it will remain so until the end of the competition.
Quote: Originally posted by j_sum1  
Competition finished some time ago
The "sticky" should probably be removed, then.

[Edited on 18-8-2016 by zwt]
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