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Optimized SRV 2.0 ...room temp ketone in 2 hrs (Page 1)
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Author Topic: Optimized SRV 2.0 ...room temp ketone in 2 hrs
spiceboy
Member posted 11-18-98 09:22 AM
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This is an update on the SRV concept, including a detailed run w/ the unit.
In this dream the ratios were as:
~1 g PdCl2
6 g CuCl2
250 ml denatured alcohol
50 ml ultra clean, vac distilled safrole
After mixing the copper salt w/ alcohol, it was chucked in the SRV.
Same for the PdCl2. Its probably better to put the palladium directly in the SRV via funnel, than to put it in a separate beaker and trying to do the mixing beforehand. The reason why is that the shit sticks to the beaker and is hard to recover when transferring containers.
when you get it all in there, assemble the unit and THROW IN A STIRBAR before you plug it up with the valve stem...this is a minor improvement that makes a BIG difference, because it enables you to get a much more turbulent agitation of the mixture...and that increases the oxygen uptake dramatically.
This was done next;
Plug the unit. Pressurize it w/ the pump.
I have found that you cannot run the electric tire pumps off of a small battery charger because it doesn't have the amps. Go out to your car and pressurize on the ground beside it. Or take a car battery and set up a work station at a bench, whatever.
Pressurize it for ten seconds. Shake it.Presurrize more. Shake it. Pressurize it until it rock hard, all the while shaking strongly. You can get a really good swirling-shaking action going on with the stir bar inside of the unit. If you think about it, this is the principle that engineers use to package spray paints in such a way that the contents can be readily mixed, while being under pressure. I really cant emphasize enough the difference this made in my dream. Your shaking effort is actually reduced, while your mixing efficiency is exponentially increased. Shake some more.
I shook the unit vigorously, nonstop for two hours. Well, stopped every ten minutes to relieve gases, and purge. Squeeze it while holding the valve open,and purge two or three times. Away from your face. Have cold water nearby to immerse the unit in intermittently, while repressurizing. This improves uptake.
Shake it. Shake it. See?
When you first place everything in the unit, the stuff is a light, green-brown-golden.
It evolves to gold-brown, then brown, then brick-red at the end. Really hard shaking was used, and never let up on.
At the end, when it was brick red, I noticed a fine suspension of Pd particles. Then, would purge and add new air. The particles would go away for a short time and come back,
so this was done a few times, and , evidently, as the reaction finished, the catalyst QUIT GOING BACK INTO SOLUTION and would deposit as a fine, granular silt on the sides of the SRV as you slowly rotate it.
The character of the solution seemed to change right about the time the shit went from brown to dark red,too...it seemed less viscous, and kinda acted like it was more easily agitated. I dont know how objective Im being here, just thiught I'd add that.
Remember, Shake It Real Hard.
There were vertical cracks appearing in the unit at the end of the Rx, indicating that it was a hearty shaking affair, replete with purge and binge....
make up dilute acid. Others have said that it's not needed, but in my dreams a much more efficient separation is achieved with dilute HCl being used to bust everything up.
Hit the stuff with about 200 - 300 ml of this
It gets cloudy and tan-crap-greenish color and a HEAVY RED OIL falls out to the bottom.
But its full of catalyst. Get the buchner funnel and your patience together. Assemble them. Filter all this crap about 3-4 times with the paper I have.....dont know about you..A clear red oil is obtained, and believe it or not, ZERO TAR. ZERO.
The result? 37 ml of ketone from 50 ml safrole. Thats over 70%. Its repeatable. It IS NOT A FLUKE.
There was extremely little iso and even less
unconverted olefin.
Removing the catalyst is a bitch, but its not
really bad. You do need vaccuum.
It seems like denatured ethanol is superior, in my dreams, to methanol as a substrate.
well, there you have it. If anyone is not afraid of shaking for two hours, this is a very viable way to get the stuff.....
Low temps seem to favor a better all-round set of kinetics for this reaction.
spiceboy
Member posted 11-18-98 09:46 AM
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Addendum:
After about 45 minutes of prssure/ shaking, 2ml of water was added to the mixture.
This detail was added because it *may* have been important to anyone else finding themselves in this dream. It maybe wasn't necessary, but I have no way of knowing if/how much water is in the denatured (slx) alcohol. The dihydrate was used,salt-wise.
beagle boy
unregistered posted 11-18-98 01:50 PM
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Spiceboy: thanks for the great post!
If you have a stirbar in the SRV is it really necessary to shake? Seems like if you could get a really good vortex going then maybe it wouldn't be.
Bright Star
Member posted 11-18-98 02:41 PM
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Beautiful!
About how many 'prepressurizations' did ya use?
Is the stir-bar just for 'ball-in-paint-can-effect', or did you let it sit on a stri-plate for a while?
Did you use the electric-pump for a reason? Is a tire/bike pump OK?
Kleen-Strip denatured OH... contains ~4% water ... the 2mL of H2O was added on top of the ~10mL of H2O in there. Did you have this information, or were you just making sure?
Lovely!
PS- The benzoquinone method yields for me have always been 70-78% ... The highest yield I ever got was 83% from the SRV. Thank you Spiceboy!
Piperine
Member posted 11-19-98 01:51 AM
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Cool! Was the usual pressure used w air?
Stonium
Member posted 11-19-98 08:01 AM
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NICE goin' Spiceboy. Really, really nice!
And it sounds like just the thing for toning those flabby bicep/tricep muscles too! Hot Damn...
GROOVY!
Over/Out,
Stonium
spiceboy
Member posted 11-19-98 10:50 AM
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Beagle boy- You cant really get a vortex going. The bottom of the 2L bottles in my dreams are stippled, and they cant be stirred while standing up. Lying sideways, a weak stir rate can be achieved...My dreams have convinced me of one thing; There is no substitute for the raw kinetic energy supplied by hard shaking. You do get a vortex going, tho, its just a swirl/shake vortex which the stirbar helps you get going. Holding the unit w/ two hands, horizontally, you keep your left hand a little higher(it has the bottom) than your right one. You wanna keep the sol'n away from the seat of the valve stem.
Bright Star- I probably pressurized it a total of 15-20 times in the 2 hrs. Im pretty sure that I re-upped it every 10 minutes, at least, but that sporadically(which is never good) I would immerse in cold water(~15c) while pressurizing, and then purge it ,like immediately, which really means that I would fill it TWICE in ten mins on a couple of the intervals. I was aiming at really going for the uptake by;
a) Immersion in cold water after a refill followed by immediate purge/refill
with shaking. I shake it hard.
No stir plate was used at any time.
The real utility of the electric pump is this; It has a convenient on/off switch mounted on top of the unit. The chuck allows you to fill the container without detatching/reattaching to air it up. This means all around less fumbling around for me.
Also, I can really put the pressure to it this way. The work is physical enough, so I couldn't really see getting a manual pump too, though Im sure it works that way too, which is great. The whole mentality here is flexibility that enables adaptability.
Piperine- I have had so many of these dreams I just go by feel. I know this is very imprecise(ouch!) but you do get a feel for it. FYI, when its so hard you cant indent it with 'normal' hand sqeeze pressure, its about 40-50 lbs. This is the general area it was in......
ketone
Member posted 11-19-98 12:06 PM
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I concur 100% with spiceboy with shaking versus stirring...even a good vortex doesn't get as much O2/air into solution...and that's exactly what you're trying to achieve.
spiceboy: nice work
-k
ketone
Member posted 11-19-98 12:23 PM
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Oh, a note that might help...
Somebody who is not be has had good success using 50mL olefin, abs. anhydr. EtOH+5mL H2O and CuCl2.2H2O.
(He used abs. anhydr. EtOH because that's what he had available to him at the time).
-k
spiceboy
Member posted 11-19-98 12:49 PM
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On the workup, you will find a difficult emulsion when you wash w/ dilute base.
It looks like thick chocolate. A ringstand and an hour or so, combined w/ a little swirl here and there enables separation in a nalgene funnel.
Does anyone have a definite b.p. for final oil?
Safrole comes over @140 on this ol' aspirator...
Or should I go find my buddy w/ the super
Boekel Cenko?
dito
Member posted 11-27-98 09:04 AM
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Can the SRV be done in glykole used as solvent and insteed of using PdCl2 and CuCl2 one would use Pd(2)OAc and Cu(2)OAc (and maybe use less of the valuble Pd), can this be done with succses?
Another Q for you boys (boys becouse I dont think there is any girls posting here, maybe I wrong):If you would use a bigger SRV let's say a 3l would you be able to repressurise the SRV less times or could the SRV be used with lower pressure (or maybe pressure promotes this reaktion?)?
Last Q: If this is done outside a winter day with a day temp of maybe -5C would this, as I think help produse the ketone insteed of the aldehyde if it was done hot?
How about it boys, what do you say?
dito
Member posted 11-27-98 09:04 AM
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Can the SRV be done in glykole used as solvent and insteed of using PdCl2 and CuCl2 one would use Pd(2)OAc and Cu(2)OAc (and maybe use less of the valuble Pd), can this be done with succses?
Another Q for you boys (boys becouse I dont think there is any girls posting here, maybe I wrong):If you would use a bigger SRV let's say a 3l would you be able to repressurise the SRV less times or could the SRV be used with lower pressure (or maybe pressure promotes this reaktion?)?
Last Q: If this is done outside a winter day with a day temp of maybe -5C would this, as I think help produse the ketone insteed of the aldehyde if it was done hot?
How about it boys, what do you say?
dito
Member posted 11-27-98 09:04 AM
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Can the SRV be done in glykole used as solvent and insteed of using PdCl2 and CuCl2 one would use Pd(2)OAc and Cu(2)OAc (and maybe use less of the valuble Pd), can this be done with succses?
Another Q for you boys (boys becouse I dont think there is any girls posting here, maybe I wrong):If you would use a bigger SRV let's say a 3l would you be able to repressurise the SRV less times or could the SRV be used with lower pressure (or maybe pressure promotes this reaktion?)?
Last Q: If this is done outside a winter day with a day temp of maybe -5C would this, as I think help produse the ketone insteed of the aldehyde if it was done hot?
How about it boys, what do you say?
Stonium
Member posted 11-27-98 09:41 AM
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dito: No "girls" huh? The hell you say!
Over/Out,
Stonium
Piglet
Member posted 11-27-98 10:33 AM
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Some while ago, I began working on a sort of SRV type vessel. I assume that the PRESSURE is needed to help get the O2 into solution? What would happen if one simply bubbled O2 (or even compressed air) through an unpressurized vessel? The bubbling would do all the agitation for you? Maybe just buying a cheap electric air-pump (like for home-mechanics) and bubbling like fuck would be an easy (on the arms) solution?
I KNOW that O2 uptake will be much slower. But, then again, the surface area created by the bubbling should (?) make up for that...
Nice one SB,
Piglet
ketone
Member posted 11-27-98 06:34 PM
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O2 uptake from a 'bubbler' will not be adequate and you'll waste huge amounts of O2...
Severe shaking and higher than atmospheric pressure will result in O2 intake into the solution. The reason for high pressure is to provide a significant reserve of O2. Using a 3L bottle will indeed provide for a large O2 resevoir and thus you can get away with less repressurizations. Higher pressure will also achieve the same result (ketone was brave enough to dream this reaction at 65psi the other day...SCARY SHIT!)
Don't do the reaction approaching 0c...you need some water in the reaction and you don't want to risk it reaching it's freezing point! Cool room temp (~20c) will be just fine. Speed, a constant O2 supply, and reasonable temp are the keys to avoiding the aldehyde.
-ketone
r2d3
Member posted 11-27-98 10:46 PM
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When did everyone change from MeOH to EtOH?
Bright Star
Member posted 11-28-98 11:40 AM
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MeOH works well for me.
Planet E Toon
Member posted 11-28-98 12:50 PM
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Spiceboy, I remember there were comments about aldehyde formation using the SRV. Can you comment on your methods for analyzing the yield of ketone.
Christ, such a great yield at room temp in 2 hours is alot more cost-effective than O2 ballon method for 40+ hours.!
ChemHack
Member posted 11-28-98 07:36 PM
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r2d3 asked: When did everyone change from MeOH to EtOH?
Would you rather buy a gallon container of EtOH from the hardware store or a donzen smaller ones of EtOH from the automotive store?
Even if the cost comes out about the same I'd feel better about the former...
If you are doing a lot of work, especially if you are purifying a bunch of MeAm.HCl it is much more convient...
ketone
Member posted 11-29-98 02:31 PM
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Plus EtOH is marginally nicer to work with from a health point of view...
-k
Osmium
Member posted 11-30-98 02:32 AM
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Ketone: Why do you say water is needed in this reaction? Every single percent of water will slow the reaction down somewhat. Don't add water!
spiceboy
Member posted 11-30-98 09:20 AM
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A few comments:
#1)I believe that there are no differences on a notice-able scale between MeOH and EtOH.
Ethanol isn't as fearsome to handle, its cheaper in bulk,too...
2) Planet E Toon- Distillation followed by amalgamation/reduction. The yields aren't consistent in this stage, yet, so I have refrained from posting about yet more inconsistent results. Sometimes I am guilty of that, but it is usually due to over-enthusiasm more than anything else.
The smell alone tells you that you did something right. There is absolutely no smell of safrole or isosafrole, even though I believe there is a little in there...very little.
There were comments made about the tendency to aldehyde formation. It happens if you starve the stuff of oxygen. It happens if you
let the rx heat up. @20 deg.c there is little, if any, aldehyde formed. An overload of oxygen and cool immersions w/ hard shaking PRODUCES KETONE!!!
Osmium- I don't want to presume to correct you, but my understanding was that water was essential in this scheme. I dont have the refs anymore, but I think optimal water content was ~ 6%. Does anyone still have any of those refs?(on the industrial Wacker)
dito
Member posted 11-30-98 09:49 AM
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Hi boys last time I f***ed up good posting 3 times sorry
But you guys havn't given me answer to my Q and the Q was:
Can the SRV be done in dihydroetan used as solvent? And insteed of using PdCl2 and CuCl2 one would use Pd(2)OAc and Cu(2)OAc (and maybe use less of the valuble Pd), can this be done with succses?
Well I'll try not to f*** up this time
spiceboy
Member posted 11-30-98 10:29 AM
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dito- If you check JOC 34, 'Oxidation of Olefins w/ Alcoholic Pd salts', you'll see that they ran the rx in a variety of solvents. I believe you will even see that they were of your mindset and used glycols as solvents.
If you are really interested this is THE ref.
But if you want me to save you the trouble, I will.
NOTHING CAN TOUCH THE 'BIG THREE'
1) Methanol
2) ethanol
3)isopropyl
these solvents leave glycols gasping in their dust when it comes to these catalytic oxidations. Nothing else can touch them, except maybe DMF, and thats iffy...
Piglet
Member posted 11-30-98 11:09 AM
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I wonder if a cosolvent can be added to increase O2 solubility?
spiceboy
Member posted 11-30-98 11:26 AM
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Probably. This was my thinking when I stumbled onto the article(s) that led to the post I made titled 'Boosting the Wacker with ...shampoo? ' a few weeks ago.
Since O2 is available, and readily so, I think the way to optimize this set of kinetics is to do what Osmium(the pope) did
and go to a tank of O2 for max yields...
Personally, all the other ways to get the ketone are beginning to lose their appeal
Piglet
Member posted 11-30-98 11:35 AM
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The nitrite Wacker is easier on the arms!
ortho
Junior Member posted 12-02-98 08:09 AM
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What is needed is an automated shaker.
I dream of an old heavy-duty window fan.
Straped to each fan blade is a SRV. The speed of the fan is adjusted to get the maxium shake.........maybe some mixing balls added to the SRV.
dito
Member posted 12-04-98 08:10 AM
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Insteed of using PdCl2 and CuCl2, could you use Pd(OAc)2 and Cu(OAc)2 (and maybe use less of the valuble Pd)? Am I right if I think the answer is yes?
Can all platinum metalls be used for this oxidation, like PtCl2?
LIVE HAPPY!
dito
quirks
Member posted 12-04-98 09:41 AM
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I think if it was done in t-BuOH then you wouldn't even need the Cu. The intermediates act in it's place. If I can figure out how to use that stupid IR I'll have a go with the SRV...
I think most of the problems in the Pd(AcO)2/H2O2 rxn result from heating safrole with H2O2. Doing that alone would likely be enough to produce the aldehyde and isosafrole.
spiceboy
Member posted 12-07-98 01:20 PM
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quirks- Before you do, see my latest post,
'The window'
as it tells some more info you may be interested in....
dito
Member posted 12-08-98 09:35 AM
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I think one can use other oxidants then benzoq. and H2O2 maybe one could use KMnO4 and such I can't see any problem with using KMnO4 in acetic acid as the color of it is none, what do you all boys think?
LIVE HAPPY!
dito
dito
Member posted 12-08-98 09:38 AM
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I think one can use other oxidants then benzoq. and H2O2 maybe one could use KMnO4 and such I can't see any problem with using KMnO4 in acetic acid as the color of it is none, what do you all boys think?
LIVE HAPPY!
dito
gyrogearloose
Member posted 12-15-98 04:19 AM
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Spiceboy,
your rxn is good, but....................
the isopropyl nitrite method posted by rev Drone far exceeds it in scope ,simplicity
and effectiveness. Tried both, while yours works, drones gives quantitative yeild and no shaking until your tired of it.
Try it instead, I promiss you you will stop shaking and adding oxygennnnnnn.
ChemHack
Member posted 12-15-98 04:13 PM
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gyrogearloose: Cool! Perhaps you can be the the first to report the details of a dream about the practical application of Drone's theory. Let's hear it. Pretty Please!
Nefertiti
Member posted 12-15-98 08:46 PM
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Yeah - I agree - Please give the goods on this isopropyl nitrite thingy...I've seen some of the technical jargon on this - but I would love to see a kitchen method... including a guide to getting/making the precursors.........Pretty Please - Don't make a girl beg.....
Nefertiti
The Cook
Member posted 12-16-98 04:48 PM
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So I left the 'old-school' and gave the SRV a try. Yeah, this method is tight... One addition my 'partner of doom' forced was addition of more essential oil after the original amt had reacted. (You really can see the Pd sludge when it's finished)
So more was added, and more pressure/shaking occurred, and it seemed to react that stuff too. To make a long story short, an ungodly amount of ketone was made using 1.5g Pd. (Recycling in situ :-)) But I have one gripe: The bisulfite complex HATES to turn back into oil, in Acid or Base... Suggestions?
gyrogearloose
Member posted 12-16-98 10:22 PM
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OK OK.
Here is the poop.
Use his rxn to make the isopropyl nitrite
After combine PDCl2 say one gram with 2 liters ISOpropole alchol, 100 ml olifin of your choice,3.5 grams cupric chloride, it will dark brown redish, then add at least 300 ml of the isopropyl nitrite, it will change color to cocokola and bubble, brown gas.
when it gewts lighter again say after 4 hours at 30 to 40 C. quench. Add touline to extract and distill for some real fun.....
gyrogearloose
Member posted 12-16-98 10:23 PM
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OK OK.
Here is the poop.
Use his rxn to make the isopropyl nitrite
After combine PDCl2 say one gram with 2 liters ISOpropole alchol, 100 ml olifin of your choice,3.5 grams cupric chloride, it will dark brown redish, then add at least 300 ml of the isopropyl nitrite, it will change color to cocokola and bubble, brown gas.
when it gewts lighter again say after 4 hours at 30 to 40 C. quench. Add touline to extract and distill for some real fun.....
ChemHack
Member posted 12-16-98 10:25 PM
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No shaking, stirring, or heating?
Where did the gas go? Was it vented it out the window?
Nefertiti
Member posted 12-16-98 11:01 PM
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I realize I may not be the smartest Egyptian along the Nile - but I had some trouble reading your post gyrogearloose -
I thought I had it - but got lost at "add 300ml Isopropyl Nitrite" I thought that the recipe made the isopropyl nitrite....?
Anyways - my knowledge of this synth is remedial at best - but let me see if I get it:
100ml Safrole
1g PdCl2
2L Isopropyl Alcohol (is 71% good enough?)
3.5g CuCl2
Add these together and heat at 40C to 50C for four hours. After this time quench the reaction with something....(Distilled H2O?)
Take up the Isopropyl Nitrite with an organic solvent (Tolulene) and distill. The resultant substance is ......? (MDP2P?)
Am I way off course or what?
Nefertiti
Nefertiti
Member posted 12-16-98 11:28 PM
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Ahhhh - I see now... I re-read Drone's paper on Rhodium's site and now it makes sense - mostly.
Now my questions are:
Will 71% Isopropyl work? (all I can find)
Where does one find sodium nitrite?
Is the resultant product MDP2P?
Any help would bee greatly appreciated.
Nefertiti - a little wiser - but not much.
Piglet
Member posted 12-17-98 06:46 AM
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Gyro: Wow, only 1g PdCl2 for 100g alkene? That means that the co-catalyst worked!!! You have no idea how happy that makes me. Everyone I know who tried this (with methyl/ethyl nitrite,admittidly) needed more like 6g per 100g, so this is a real breakthrough. I always suspected that some imputity in the nitrite was causing the co-catalyst to be complexated (is that a word? It is now!) out of action.
Please can you write up your dream, I'm anxious to, well, COPY EXACTLY what you did to see for myself.
If it works, I will give you £1!
Good work fella,
Piglet
Nefertiti
Member posted 12-19-98 07:32 AM
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Well - I guess I'm the only one that is crazed about this Iso-nitrite thing.... I see that sodium nitrite can be ordered from the chem houses - any otc source?
Gyro - what is the "stench" factor - do you have to do this in a cornfield or can you get away with doing it in the kitchen? Aspirator - water/fume trap maybe? Can you be just a wee bit more descriptive of your method to get us lowly bees going? Perhaps start a new thread on it with a writeup of your methods......?
Nefertiti
gyrogearloose
Member posted 12-19-98 08:36 AM
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Ok
To 2 liters of isopropyl alchol add 3.5 grams cupric chloride, then 1 gram PdCl.then 100 ml of the ole safrole. this should look brown to red-brown. Then add the 300ml of the isoproply nitrite you made using drones rxn for same. Heat to 30 to 40. for 3-4 hours.
Vac off the IPA then stop. wash with Dh20 then add touline. distill off the touline then the mdp2p. the isopropyl nitrite is made easy by drones rxn posted on rhodium or here.
It works so good you can't believe it.
No shaking only stir it. I arrived at this method from bits and pieces from reading this board relentlessly. After 11 tries I got it.
Someone even posted how to make nitrite from nitrate(more easyly obtained. Fumes are handled by a open window with a fan mounted in it and rxn next to fan. slight brown gas evolves with some bubbles. When its lighter again its finished. Use TLC against the starting material.
quirks
Member posted 12-19-98 09:18 AM
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nefreti: eleusis notes from vogels (I think) on making the alkyl nitrites are probally a little clearer. And the same thing?? What's all this stuff about a "new method"? This is anceint?
ChemHack
Member posted 12-19-98 03:30 PM
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I think the "newness" is the use of isopropyl instead of other alcohols. Around here IPA is the most OTC alcohol. The higher bp of the nitrite affords easier handling and higher rxn temps. So anyway, I don't know if it is so much a NEW way as much a BETTER way... a logical extension.
Niels Bohr
Member posted 12-20-98 09:15 AM
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For improvised sodium nitrite from sodium nitrate, see Army Field manual FM-5-25 "Improvised Explosives". There is a section on making the nitrite from saltpetre and a car battery (high current), in a mason jar.
By the way, the manual is available from Delta Press or probably any local gun show.
Speaking of improvising, this hive board never ceases to amaze me on the methods conjured up to create our most delicioius honey. It emphasises the futile and pointless attempt of the law to stop busy bees from getting their honey. This SRV concept is a great example.
Piglet
Member posted 12-21-98 10:18 AM
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Gyro: I owes ya pound! beautiful
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