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panziandi
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Yes I suspect that MgCO3 and CaCO3 are probably functioning as weak bases to destroy the HCl that can form and thus stabilise the remaining material.
I'd even suspect MgO to be ok too, but I doubt CaO would be suited. Not sure about ZnO/CO3, I suppose that maybe ok too. Nice to link loxoi to proper
procedure, hopefully safer too 
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-TheMadMen-
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Hmm, if i may be excused for a moment. Chloroacetone definitely seems to be a popular chemical amongst the readers of this board. And as The_Davster
said, it is amusing, not sure what he meant by it exactly, but it is definitely amusing in it's own right as a chemical which presents itself with
such unwelcoming properties, if not handled correctly.
It is also highly useful in many regards. As we all know. But it seems, as far as i am aware, that i am the only one so far, at least in this topic,
who has made it by directly bubbling chlorine gas into acetone, i admit that it was a bold move, it is never nice to be around chlorine gas, even when
everything is well-fitted, some of it still leaks, it is repugnant material, to say the least. I Had a gas mask on however, and i am pretty sure that
i achieved the goal of converting the acetone into chloroacetone, or polychloroacetone/monochloracetone whatever, needless to say, the chlorine
definitely reacted with the acetone, as i have said before, it turned grey, it was a visible reaction, the acetone absorbed all of the chlorine that i
fed it. If memory serves me right however, it did not seem to give off that much heat, interestingly enough. But from previous experiments doing the
same thing, in which i still dread when thinking about, i bubbled some chlorine gas, a smaller amount than i did in my previous mentioned experiment,
into some acetone, and left it in a sealed vacuum-filter flask for a couple of weeks, it turned an evil looking black color very quickly, as it was
exposed to light, and it would form droplets of itself on the rubber stopper above, from the vapor formation, indicating to me what would happen
should i open the stopper, i ended up burying it deep underground in my backyard. Stupid move, but what can ya do, it was a while ago anyway hehe.
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Paddywhacker
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I tried bubbling Cl2 through acetone several years ago, but there was a very low rate of reaction and most of the chlorine was wasted.
Yeah, I did it in the back yard.
From the only slight lacramatory properties of the acetone I figured that the reaction was a failure, and wanted to try bromine, where the reactants
would be together in higher concentration.
I was planning on stablizing the chloroacetone as the bisulfite adduct, where it should be nonvolatile and easy to handle, but never got that far.
Iodoacetone is another amusing compound.
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Nicodem
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The chlorination of acetone with Cl2 is autocatalytic, which means some HCl must first form at a sufficient concentration to promote enolization. If
the temperature is too low, the acetone too dry, or whatever other reason, the reaction will not even start in any decent amount of time.
In alpha-halogenations of ketones with elemental halogens, a tiny amount of a strong acid is commonly added at the beginning to prevent this problem
as well as to avoid reaction runaways. The acid used is almost always AlCl3 (1 mol% is enough), but any strong enough acid will do. Alternatively a
protic solvent that does not react with the halogen is used to promote enolization and the polarization of the halogen. Acetic acid is most suitable
as it does not react with halogens at the reaction conditions.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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-TheMadMen-
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Would it help catalyze the reaction rate if maybe the acetone was heated(bold move i know, considering it's minuscule boiling point) and then the
chlorine passed through? Heat always seems to act in favour of increase in the reaction rate in any chemical reaction doesn't it??? As a matter of
fact, i remember reading in a classic chloroacetone prep patent from the 1940s that if you combine acetone vapour with chlorine vapour in separate
chambers or something, you get an extremely efficient reaction taking place. But that could have been because the acetone vapours themselves where hot
or super-heated?? I Do not recall this procedure requiring anything but raw chlorine gas and acetone, no special or fancy catalysts etc.....
And not to be rude, Nicodem, because what you said did sound interesting, and i took it to heart, so what your basically saying is, is that if i add a
little bit of Aluminium Chloride or even Sodium Bisulphate to the acetone before i start bubbling a large stream of chlorine gas through, then the
chloroacetone will start forming at quicker, greater, and more efficient rates??
[Edited on 12-6-2009 by -TheMadMen-]
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sparkgap
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That's not bold, that's Darwin Award material. You're exposing the vapors of an inflammable starting material to heat, so...
sparky (~_~)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
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-TheMadMen-
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Yah, well maybe i would have learned the hard way hey!! :-) But i realize that though, it's why i spoke with caution..... :-)
Thankyou for reminding me though :p
[Edited on 12-6-2009 by -TheMadMen-]
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Nicodem
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Quote: Originally posted by -TheMadMen-  |
And not to be rude, Nicodem, because what you said did sound interesting, and i took it to heart, so what your basically saying is, is that if i add a
little bit of Aluminium Chloride or even Sodium Bisulphate to the acetone before i start bubbling a large stream of chlorine gas through, then the
chloroacetone will start forming at quicker, greater, and more efficient rates?? |
The acid added is not to increase the rate of the reaction. The reaction itself needs no speeding up or any external catalysis, because it is fast
enough as it is. Like I said, it is autocatalytic (http://en.wikipedia.org/wiki/Autocatalysis) so to catalyse it any further would make little sense. The tiny amount of AlCl3 is only added to
prevent delaying of the reaction initiation. Therefore you don't run the risk of a runaway reaction. When using Br2, runaways are seriously dangerous,
particularly for those chemists, like a lab technician or a clumsy amateur, that do not or do not want to know the theory of the reaction. Seeing the
bromine does not react (discolour) they would automatically add more and more until all of a sudden the autocatalytic cycle kicks in giving them an
exquisite personal experience of a reaction runaway in their face. This problem in ketone alpha-halogenations is described in details in some
classical lab manuals like Organicum, probably also in Vogel's. A serious chemist always takes great care to prevent such accidents.
Nevertheless, this is irrelevant when introducing gaseous Cl2 to acetone on a small scale since you can not build up dangerous amounts of Cl2 in the
reaction mixture due to solubility issues. However even the reaction of acetone and chlorine can have troubles initiating sometimes. In such case
just stop the introduction of Cl2 for some time to allow some HCl to build up and then continue. Heating is unnecessary and inadvisable due to product
selectivity issues, but do not cool it bellow room temperature before the reaction initiates. But anyway, using Cl2 to prepare chloroacetone is pretty
much impractical. Chlorination with trichloroisocyanuric acid is way simpler if done following the patent instructions. But for some reasons some
adventurous members here have this (suicidal) tendency to do this by making some truly idiotic modifications. When one does not understanding what
goes on during his chemical experiment and is doing it on a small scale, he is just being irresponsible. Fine enough. But when such a lazy person, who
never bothers to venture in a library, decides to do it on a large scale, then he is behaving like an imbecile.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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-TheMadMen-
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Hehe, yeah, as amateurs, our art is not exactly fool-proof, and prone to destructive issues, i've been doing it for years though. Most crazy thing i
did, and will never do again, is, by way of a mini-blow-torch held in place by a set of metallic helper hooks, melting sodium hydroxide pellets on an
inverted softdrink can, with two electrodes and a 12 volt current embedded inside. I Watched as the sodium formed, but was rapidly oxidized to some
green shit, with an incredibly foul, toxic, smell. God i was stupid then!!
And yet, i still have all 10 fingers, and 2 eyes, thank god!! :-) Hopefully i speak for us all hehe. :-)
I'm going to investigate the trichloroisocyanuric acid procedure for producing chloroacetone, but somehow, deep in the back of my mind, i still
believe that the patent i mentioned above, and the procedure contained therein, is the best method for makin ' it.
We shall wait and see.
- TheMadMen.
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Formatik
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I've read some of the old literature which state HCl is formed in the Cl2-chlorination. This apparently interferes with yield by undergoing
condensation reactions. No need to add or increase HCl prior or during addition. In one of those preparations, CaCO3 was added prior chlorination to
get the chloroacetones (Fritsch, Ber. 26, 597).
Concerning it's lacrimator properties. Chloroacetone isn't such a big shot, considering stronger irritants like acrolein (which is also much more
lethal though as well as mutagenic). Bromoacetone is considerably stronger than chloroacetone and less lethal, but more instable. Xylyl bromide and
Bromo-MEK both around as strong as the latter. CN stronger lacrimator than all of those. Though judging by lacrimation alone (0.3 mg/m3 vs. 0.5
mg/m3), bromobenzyl cyanide is slightly stronger eye irritant than CN, and maybe a bit less lethal.
Attachment: Ber. 26, 597.pdf (117kB)
This file has been downloaded 810 times
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-TheMadMen-
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Thanks Formatik, the only problem is, chloroacetone is easily the most simple to prepare out of all of those tear gas irritants that you mentioned.
No????
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Sauron
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Every one of those except for CN and BBC has been obsolete for 80-90 years for police use and since WWI for military use.
And both CN and BBC have been utterly eclipsed by CS, which is far more effective, and is easily prepared by the Knoevenagel reaction. I posted prep
of CS with full text some time ago so UTFSE.
Chloroacetone is a JOKE. Calling it a CW agent is a century out of step with reality and thus little better than a lie. This thread is a waste of
time by an obvious troll wannabe. Check out sll the old dope cook threads he has revived. He is a shit-stirrer. Do not assist him.
Sic gorgeamus a los subjectatus nunc.
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Formatik
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| Quote: Originally posted by -TheMadMen- | | Thanks Formatik, the only problem is, chloroacetone is easily the most simple to prepare out of all of those tear gas irritants that you mentioned.
No???? |
I would say a tie between chloroacetone and acrolein. Acrolein is quite a common molecule (responsible for stench and irritation by the burning of
fats). The simplest lacrimator though is maybe thiopropanal S-oxide, the gaseous irritating principal from fresh cut onions.
The most potent lacrimator I've read of is CR (dibenz[b,f]-1,4-oxazepine). CR is a more potent lacrimator than CS (5 to 10 times more potent). Eye
irritation occurs with 2mcg/m3.
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-TheMadMen-
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Shitposts will be deleted
[Edited on 19-6-2009 by Ramiel]
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-TheMadMen-
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Thanks for that info Formatik, i appreciate it bud. Yes you are right about Acrolein, it does indeed have a very foul odour to it i must agree!!!! :-)
Albeit a simple one. :-)
[Edited on 19-6-2009 by -TheMadMen-]
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Sauron
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There are any number of research and industrial chemicals that are lachrymatory, but that does not make them "tear gases" much less "chemical warfare
agents"
In WWI both sides as a matter of urgency pressed into use a nuber of such compounds, most of which proved to be highly unsatisfactory. Now almost a
century later you will still see these on historically based lists of agents but that is just brainless bureaucracy in action not science.
Between the wars the criteria for ideal military and civilian (lae enforcement) lachrymators were established, most of the WWI agents were abandoned
and newer agents such as CN were developed. CS came along and we used it against NVA and VC during the Indochina wars as well as ubiquitously as a
police riot control agent.
In the 70s and 80s some newer agents were developed such as CR but AFAIK have not seen widespread use.
Anyone interested in the chemistry and technology of such agents can access a wealth of accurate information in the open lit but not in this benighted
thread.
Sartori documents in details why chloroacetone and acrolein FAILED snd his book is in the forum library,
Formatik, please don't feed the animals.
Sic gorgeamus a los subjectatus nunc.
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The_Davster
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Thread Split
21-6-2009 at 07:30 |
The_Davster
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Thread Split
21-6-2009 at 09:02 |
SunlightLover
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i didnt mean that btw, ok, sorry.
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Retired_Oz
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Chloroacetone - making it
I have produced chloro-acetone more times than i care to remember - whilst having an understanding of what's going on in literature - there are a few
things to note from experience. - firstly adding cl2 to acetone - never in my considerable experience has it failed to initiate (with marble chips in
it) when the cl2 is bubble in.
From time to time stir the marble chips - bubbles come up when they are stirred indicating reaction with the acid build-up . Cl2 s easiest to produce
by dripping Hcl (32% hardware store is great) in calcium hyperchlorite (pool shop) - reacts vigorously to start with - then as water build up from the
Hcl more slowly.
Some Hcl vapor can come across so a water bubble is inserted then the potential to carry water vapor - a sulfuric acid bubbler then inserted to
remove water. 98% H2so4 will double its volume then cease to take out anymore water so be liberal with the acid in the bubbler.
So bubbling then into the acetone is dry cl2. The reaction is mildly exothermic. Bubble at a rate that keeps the temp under 5 degrees C whilst the
acetone container is immersed in an ice bath. Stir every thirty min or more often. Literature states that the reaction should proceed until 10%
chloroAc saturation - Then filter and distill- vacuum is good and at 5 tor comes over at around 70 degrees. My pump gets to 0.0004 of a tor so i have
to chill the receiver bowl.
Runaways occur with no caco3 present - they dont explode just run away in a second and usually do blow apart the container.
20 liters of Hcl (about 7 liters of avail chlorine (the cl2 comes from the Hcl not the pool chlorine)) into 10kg of pool chlorine gives 3.5 kg of Hcl
build up and 3.5 kg attaches to 5.7 kg of acetone to produce 9 or so kg of mono product minus the dichloro product which as long as the solution at
the point of entry of the cl2 does not get above 5 degrees.
The Hcl neutralized by the caco3 gives calcium chloride plus c02 plus water. The cacl2 then removes the water (its hygroscopic and all settle on the
bottom some what shielding the marble from the solution above - hence the need to stir. A mechanical stirrer is not good as even on slow a lot of cl2
is released into the room.
Using salt and water cooled to -12 or more getting the acetone down to -3 or 4 the blasting in the cl2 and cooling to holding it about 3 degrees gets
you all the chlorine in in around 30 hrs. Not to shabby. The reaction becomes too sluggish at more than -3 degrees to be worthwhile.
I proceed from experience and saturate to 30 - 35 % without a large dichloro build up. At 35% saturation expect 10% di's - the effect it has does
little in most reactions.
Allow to come to room temp when finished and a lot of acid vapor will be present above the acetone if u havent stirred well - bubbles come up from the
marble and the production of mesityl oxide can can continue for hrs. Filter at the pump and u wind up with a dark red solution.
I find a distillation with packed column in a water bath keeping the temp at the top of the column at 56-57 degrees best - its lengthy - distill out
of marble chips - then still through the column vacuum distill - you may get water if the cacl2 didnt remove it all or you filtered thru water when
filtering. Chloroacetone form an aziatrope (common boiling point) when distilled with water.
I have used the trichloro process in the latter years but its harder to distill without disintergration due to impurities present in the commercial
pool stabilizer products.
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The WiZard is In
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| Quote: Originally posted by Nicodem |
I find it unbelievable that after all the warnings and accidents reported here (UTFSE!) there are still people who, rather than
following the original patent procedure of chloroacetone preparation using TCCA, they try to do their own immensely irresponsible and irrational
modifications. |
Amen.
Complete lab prep instructions can be found in the obvious
book in the SciMadOrg library.
And by the by you forgot an essential chemical in its synthesis —
calcium carbonate, in order to neutralise the hydrochloric
acid liberated in the reaction.
Did you say you added HCl.....!
djh
---
The Chymists are a strange Class of Mortals, impelled
by an incomprehensible Impulse to take their Pleasure
amid Smoke and Vapour, Fume and Flame, Poison and
Poverty - Yet among all these Evils, I seem to live so
sweetly that may I die if I would change places with the
Persian King!
Johann Beccher
Physica Subterranea, 1703
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entropy51
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| Quote: Originally posted by The WiZard is In |
And by the by you forgot an essential chemical in its synthesis —
calcium carbonate, in order to neutralise the hydrochloric
acid liberated in the reaction.
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And you think marble chips are composed of what, exactly?
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The WiZard is In
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-----------
The original poster does not mention marble chips. First mention
is by Retired_oz. I was not replying directly to his/her post.
Admittedly — I did not notice their mention of marble chips.
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The WiZard is In
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| Quote: Originally posted by Sauron | Vh;oroacetone is an industrial chemical, period.
It is an OBSOLETE lachrymatory agent and LESS effective as such than chloroacetophenone (CN) or o-chlorobenzalmalononitrile (CS) which are what
eclipsed it almost a century ago.
No one stockpiles haloacetones as CW agents. They are of historical interest only as such. |
-----
I would expand on the historical aspects.
Amos A Fries and Clarence J West
Chemical Warfare
McGraw-Hill 1921
"The first lachrymator used was a mixture of chlorides and
bromides of toluene... Chloroacetone and bromoacetone
are also well know lachrymaotrs, though they are expensive
to manufacture and are none too stable.. Because of this
the French modified their preparation and obtained mixtures
to which they gave the name "martonite." This is a mixture
of 80 per cent bromoacetone and 20 percent chloroacetone,
and can be made with nearly complete utilization of the halogen."
Curt Wachtel
Chemical Warfare
Chemical Publishing 1941
Chloroacetone. French "Tonite"
The early gas mask gave, however, full protection against
choroactone. It was therefore discarded the follow year, 1915.
Technical Properties : It polymerizes on storage and is
transformed into less irritant forms.
Augustin M Prentiss
Chemicals In War
McGraw-Hill 1937
Because charcoal readily absorbs chloreacetone and therefore
even the early gas masks afforded adequate protection against
it and because bromoacetone proved to be a better tear gas,
chloreacetone was displaced in 1915 by bromoacetone and
other more powerful lacrimators then introduced. A relatively
small amount of chloroacetone was used in the war, and it
played but a minor role in the early stages of gas warfare.
----------
Donald Richter
Chemical Soldiers: British Gas Warfare in World War I
U of Kansas Press 1992
Foulkes [Charles Howard b. 1875] considered that the rank of pioneer,
equivalent in the Engineers to the rank of private in the infantry, and the
corresponding daily base pay of one shilling nine pence would hardly
attract the class of men desired for his purposes. French, too, had urged a
higher rank and rate of pay on the grounds that many chemists already
serving in skilled positions in the army, especially those in the electrical
units, would already be receiving higher rates of pay than pioneers. [9]
Accordingly, the Army Council stipulated a rate of pay of three shillings a
day and an entering rank of corporal. " [10]
In late May, Foulkes drew up a poster advertising for volunteers: "Men
with training in Chemistry are required for service in the Royal Engineers
overseas. " The poster promised immediate promotion to corporal,
beginning pay of three shillings a day, and a term of service not to exceed
the duration of the war. Usual standards of height and chest measurement
were to be waived as long as the volunteer was "organically sound and fit
for service in the field." Furthermore, the eyesight examination might be
passed with the aid of eyeglasses." Foulkes suggested that recruiters also
disregard the upper age limit of forty-five, on the assumption that the
chemists would not be called upon to do anything physically more
strenuous than turn gas valves on and off. One would-be recruit, rejected
out of hand by all other units because of a severe foot deformity and
short-sightedness, found an easy entrance to the Special Companies."
Martin Sidney Fox, one of the early recruits, described the initial selection
as "almost willy-nilly. [13] Nor was there a single Regular Army officer in
the entire unit except Foulkes. Until the formation of the enlarged Special
Brigade in 1916, all the officers were carried on the army's General List, a
miscellaneous category of officers not permanently assigned to a
particular unit.
Foulkes continued the recruitment drive initiated earlier by the War Office
among the universities and colleges to identify graduates and advanced
students with chemical knowledge. One such volunteer later jocularly
maintained that he had been "taken in, in more senses than one, "-that he
had been asked about chemistry but not about ability to perform heavy
porterage. [11] "They wanted chemists," a youngster later recalled, "so I
looked up the formula for water and told them it was H2O, and I was in." "
Another soldier remembers being asked only one question at the
recruiting office: "What does H2SO, stand for?"" The Chatham
"examination," as many later came to realize, was the utmost farce, and
the examining officer was primed to admit as many acceptable and
marginally acceptable applicants and transfers as possible.
Foulkes also circulated notices seeking qualified chemists among the
ranks already in service in France, characteristically assuming that his
needs would be accorded high priority and that his requests for transfers
to the Special Companies would be made expeditiously. L. Hague, a
gunner with the Royal Field Artillery, remembers being sent by his ad-
jutant in August 1915 to Chatham where a Royal Engineers recruiter in-
terviewed him: "He reminded me that the Germans had used gas at
Ypres. They might use a new type of gas in the future. If so, could I take a
motorcycle and a vacuum flask to the front, take a sample of the new gas,
return to base and analyze it?" Hague was given a four-day leave and told
to visit his chemistry professor and learn what he could about gas
analysis. "So, almost overnight, I changed from Gunner to Corporal R. E.
(pay 3/- per day) almost unbelievable wealth. " [17]
Foulkes's transfer requests, however urgent, did not always meet with
such swift accommodation. Actually the notices elicited considerable
resistance from commanders asked to release their men. When a Lt.
James Pratt saw the notice, he immediately sought out his commanding
officer: "'As regards chemists,' I said, 'I'm a trained chemist myself and I've
got at least half a dozen more in the company. Do you want me to submit
their names?' He said 'I don't want my men to go into these God-damned
cushy jobs. You'll render a nil return.’ " [18] Foulkes sought support from
the War Office in overcoming such resistance. Occasionally the War
Office simply ordered such transfers despite objections from commanding
officers and not always with the consent of the individual soldier. Lt. Jack
Sewell, a bicyclist with the 28th Division, was repairing telephone
connections in the Ypres area when in mid-1915 "a mysterious wire"
arrived at divisional headquarters ordering him to report for special duty.
Sewell's wording suggests the transfer came as a total surprise. "For
some obscure reason the Staff had insisted on the use of trained or
half-trained chemists with a leavening of chemical labourers combed from
the P.B.I. [poor bloody infantry], to let off gas in the front line. Little Tin
Gods move in a mysterious way their wonders to perform." Sewell
thereupon joined the Company 186. [19] A pharmacist maintained he was
plucked out of the infantry because his recruiting officer had not been able
to spell pharmacist, and so had written chemist instead. Since the Guards
unit to which he had belonged suffered severe losses shortly afterward,
he considered he owed his life to his fluke transfer to the Special
Companies." [20]
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Anders Hoveland
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I made a bromoacetone tear gas by mixing bromide, H2O2, bisulfate and isopropyl alcohal. After putting in the freezer for a few hours, long thin
Na2SO4 crystals appeared and dark brown oily droplet appeared at the bottom; I think these were brominated oil of some sort. The Br2 formed would have
oxidized the alcohal to acetone and then to various bromoacetones. Some of the heavier of these would hydrolyze to make bromoform.
I had also read that an isopropyl ether of acetone can form under these conditions. The vapors that came out when the reaction container where opened
brought tears to my eyes, whereas bromine, as irritating and corrosive smelling as it was, did not.
As a bit of side interest: chlorine reacts with methanol to form methyl hypochlorite. It reacts with ethyl alcohal in the presence of a base to form
chloroform and CO2.
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