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Author Topic: Benzaldehyde via cycloknights cinnamin aldehyde  (Read 201 times)

shroomedalice

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Benzaldehyde via cycloknights cinnamin aldehyde
« on: January 23, 2010, 05:13:54 PM »
well I just tried this route to benzaldehyde and it works but it is not as nice as he would lead us to belive.
maby I have done something wrong.

I manged to get around 20ml of benzaldehyde from a 500ml reaction flask after 4 hours of distilling over water
and benzaldehyde.

the caustic turned all my glass to a one peice outfit by glueing it all together and making it near impossible to
open half the joints. I lost three pieces of nice glass today oh well shit happens I have more but the big thing
that got me was the tar and the amoung of cinnamin aldehyde that came over with the distalate.

when reading his post on SM one would think the majority was benzaldehyde and that cinnamin aldehyde does not
come over in great quantities due to the difference in vapour pressure.

this is not what happened at all I found that I got around a 50/50 percent benzaldehyde cinnamin aldehyde from the
distillation and this is with a ph corrected solution and a fractionating collumn that was not insulated so as the
aldehyde had a large reflux ratio. yes there was benzaldehyde but at the rates it came over and the
amount of impurity I wonder if I am better of using my old route of lummins and sommelet rather than
useing cinnamin aldehyde or trying the persulfate cell.

I will try this again and post the exact rate of cinnamin that is droped into solution and the amount of drops of distillate
collected in the near future.
I used roughly one drop of cinnamin too three drops of distillate beliving that the oil came over in around 30% volume.

I am now having to order more glass due to this route and I belive that any one trying it should use either teflon sleeves or
rap there joints with teflon.

one thing I did do different was use the boiling solution as my steam source rather than use an external steam source.
this may be the cause of the tar and high cinnamin aldehyde content though I belive it would only make the
content of the cinnamin aldehyde higher in the distallate if I used and external source of steam.

I tried this about a week ago with out the fractionating collumn and instead of dripping in the cinnamin I put it all in whole sale.

this produced a high benzaldehyde containing oil but a lot more tar.

I belive organikum had simular problems if you read SM so if you have had any experiance with this reaction
please comment and let me know.

this was just a test for my mantle and glass setup as I just got it all together pitty if fused so many pieces.

truly it is not what I am aiming at but if some one has knowlage of this reaction I can have some use for it
if not some one else will.

mesmerized

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Re: Benzaldehyde via cycloknights cinnamin aldehyde
« Reply #1 on: January 25, 2010, 12:12:17 PM »
sorry, I personally don't have any experience with this process however I did have a lot of interest in it prior to becoming more interested in the oxidation of C6H5CH3 route also in same thread.  iirc org not only had issues with it, at one point didnt he say he couldnt get it to work?  Too many people have since validated this procedure but many have said the workup is far from a snap.  Though I intended to re-read the thread since imo it is mandatory reading should one becomes interested in either of these routes to C6H5CHO, I do remember that rate of feed was very much an issue with it being highly suggested by the author that C9H8O be added dropwise to avoid additional polymerization and supposedly boosts yeilds over 20 some odd percent, An absolute deal breaker was in maintaining a ph of 12-13 which slightly differes but not much from the patent pyschokitty threw out their during the threads formation, I am sure you have a copy but just in case I have attached it for you.  It makes for good reading when comparing both procedures side-by-side.  I would have asked that you make sure some of the steps utilized were in line changes that he made towards the end of his involvement in the thread, which happened to derive from his sidetalks with org. and also the patent itself (ie change in type of surfactant, I think ?) also NaOH over the carbonate. However your quandry with NaOH verifys pretty much that you have,   :(

Also I think there was mention that after the first 10 minutes of the process discontinue the additions of C6H5CHO in order to check both the rate and concentration of distillate, if either faltered not to continue with the addition but to adjust the ph accordingly.  The rate of distillate should be balanced with rate of addtion thus providing a very dilute solution in the reaction vessel. There is a hint that there would be major problems if the addition proceded too quickly even though the conversion rate itself was relatively fast moving.  Not sure if this helps you but it may help you isolate your problem.  If possible could you include some of the reactionary conditions employed?  Type and amount of surfactant use, frequency in checking ph levels and the actual ph level one decided was best.  Lastly what type of steam distillation setup did one work with and has it been effective in the past.  These may bee the areas in which problems could occur as they were also a point of contention with cycloknight iirc.



much love
mez
« Last Edit: January 25, 2010, 12:34:53 PM by mesmerized »

mesmerized

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Re: Benzaldehyde via cycloknights cinnamin aldehyde
« Reply #2 on: January 25, 2010, 12:25:55 PM »
sorry, just re-read your post and you did cover the rate of addition already.  Though is seems a bit lower than the author's suggestion, Maybe some of the more chemically gifted members can scratch out a hypothesis on this one but just a guess would be that part of the success in this procedure is again geared around not only the rate in which the addition occurs but its volume as well.  The best as I can tell it has to do with not wanting an excess of C9H8O sitting in the reactionary vessel prior to it utilization in the process.  This only affords the oppurtunity to botch things up (maybe the tar and/or formed emulsions, etc, etc).  By adding the product into the reactionary vessel drop by drop one minimized this possibility.  This of course is furthered by both a relatively quick conversion rate and keeping the addition balanced with the rate in which the distillate is collected.  The reason this is causing the red flags so to speak is you did mention adding in larger amounts of C9H8O?

Still this doesnt seem to be an isolated occurance as I do recall various other threads where experimenters also had the same issue

mez

shroomedalice

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Re: Benzaldehyde via cycloknights cinnamin aldehyde
« Reply #3 on: January 26, 2010, 06:54:58 AM »
thankyou for your reply I shall read the patent you have posted.

also I did not use a surfricant so this may also be the problem though it may also be the lack of steam distillation setup.

I remeber that I used no fractionating collumn with the first run that I added it all in whole sale and got a good percentage of benzaldehyde
on my distillate.

this may be the key for me as I am using the solution as the steam source. maby the need of a fractionating collumn is only needed if excess steam is
introduced into the system.

iknowjt

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Re: Benzaldehyde via cycloknights cinnamin aldehyde
« Reply #4 on: March 27, 2010, 02:27:20 AM »
Thank you for the report shroom, i'm pretty dead set on giving this one a try as well.  on a side note, i never could seperate a seized joint until I did it the glassblower's way,  which always works.  Big hot flame, no more than 10 seconds of rotation, then pull.
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