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prole
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Need help with prep. of phthalic anhydride from naphthalene
I am interested in preparing phthalic anhydride from naphthalene in order to prepare phthalimide, in an OTC fashion, of course. I have googled, and
found plenty of info on going from the anhydride to phthalimide. Merck gives several refs, which I checked out. Faith, Keys, and Clark's
Industrial Chemicals outlines a great procedure utilizing vanadium pentoxide catalyst and a maze of furnaces, cooling chambers, sublimation
tanks, etc. This is beyond my humble basement/garage/back patio lab space, and I'm a little skittish ordering vanadium pentoxide, even though I would
like some to try SO3 when my balls grow a little bigger. The one process Merck hinted at, using naphthalene with HgSO4 and CuSO4 in the presence of
H2SO4 has thus far eluded me, but seems the most feasable. It was not in the above-mentioned volume, which I at first erroneously believed. Can
anyone please offer a ref. or procedure using these chemicals? These reagents are within my grasp, indeed, they are within my lab. I know I can
simply order phthalic anhydride, but why buy it when I can spend huge amounts of time and money trying to make it? Thank you in advance for your
help, time, insults, and jabs.
I humbly remain,
-prole, the common clay chemist
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leu
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A laboratory scale apparatus for oxidizing napthalene is described in the Fundementals of Dye Chemistry which is available here if one looks
around for it  The process which is probably more suitable for the average
laboratory is to chlorinate coarsely ground napthalene and then oxidize the napthalene tetrachloride with nitric acid:
Commercial nitric acid (sp gr 1.45 10 parts) is gradually added to napthalene tetrachloride (1 part) and the mixture
heated until a clear solution is produced. This is then evaporated to dryness, and the residue distilled, the phthalic anhydride which passes over
being reconverted into phthalic acid by dissolving it in dilute soda: the acid is then precipitated by adding a mineral acid, and the crystalline
precipitate purified by recrystallization. Phthalic acid crystallizes in colorless prisms, and melts at 184 degrees, with the formation of the
anhydride so that if the melting point is taken after solidification it will be 128 degrees, the melting point of phthalic anhydride
The oxidation with concentrated sulfuric acid and a small amount of mercury or mercuric sulfate is carried out at 220-300 degrees(GP 91202); which
seems less easy than the procedure disclosed above. Another old procedure from nitronapthalene was disclosed in British Patent 145071.
[Edited on 8-9-2006 by leu]
Chemistry is our Covalent Bond
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solo
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I also had this from the Hive..........solo
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Chemistry Discourse Thread:
Posts 1 - 3 of 3 Subject: Phthalic Anhydride from Naphthalene
foxy2
(Distinctive Doe)
09-08-01 13:28
No 211336
Phthalic Anhydride from Naphthalene
This maybe of interest to anyone looking at Methaqualone.
Now if only they sold V2O5 at the grocery store!!!
Gibbs Phthalic Anhydride Process; Gibbs-Wohl Oxidation of
Naphthalene.
H. D. Gibbs and C. Conover, U.S. pat. 1,285,117 (1918)
A. Wohl, U.S. pat. 1,787,416-417 (1930)
R. N. Shreve, Chem. & Met. Eng. 52(5), 103, 117 (1943)
Kirk-Othmer, Encycl (New York, 1953)
Faith-Keyes-Clark, Industrial Chernicals, 2nd ed, p 610 (New York,
1957)
Kirk-Othmer, Encyclopedia of Chemical Technology 10, 585
L. F. Fieser and M. Fieser, Advanced Organic Chemistry, p 795 (New
York, 1961).
Do Your Part To Win The War
Rhodium
(Chief Bee)
09-08-01 13:47
No 211340
Re: Phthalic Anhydride from Naphthalene
I believe there is a method on my page for this transformation
using sulfuric acid as oxidant and mercury or mercury sulfate as
catalyst. If not, it is at least posted here.
PolytheneSam
(Master Searcher)
09-08-01 18:37
No 211399
Re: Phthalic Anhydride from Naphthalene
See US patent 729502 on an electrolytic process for making phthalic
acid from naphthalene.
http://www.geocities.com/dritte123/PSPF.html
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and some stuff which you may already know......
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pHarmacist
(Hive Addict)
03-03-03 16:21
No 413466
Two Methods for the Preparation of Phthalimide
(Rated as: excellent) Bookmark
pHarmacist's voice: A very neet way of preparing primary amines is by using Gabriel Synthesis. Most of you are familiar with Gabriel synthesis. For
you that are not; it's basicly conversion of alkyl halides to corresponding primary amines by treatment with potassium phthalimide, followed by
hydrolysis. In my opinion Gabriel Synthesis is a great route to phenetylamines. Below I introduce to you two methods for production of phthalimide - a
reagent that is universaly used for Gabriel synthesis.
Mechanism for Gabriel synthesis:
[image]
Phthalimide:
Method 1. Place 100 g (0.675 mol) of phthalic anhydride and 105 mL of concentrated ammonia solution in a 1-litre round-bottomed flask fitted with a
wide air condenser (10 mm in diameter). Heat on a sand bath, gradually at first until the mixture is in a state of quiet fusion and forms a
homogeneous melt (the temperature reaches 300°C in about 1.5-2 hours; all the water is evaporatedduring the first hour). Shake the flask occasionally
during the heating and push down any material whicj sublimes into the condenser with a glass rod. Pour the contents of the flask while still hot into
a porcelain basin, allow to cool and grind to a fine powder in a mortar.
The phthalimide (95 g, 96%) is practically pure and melts at 233-234°C. It may be recrystallised from EtOH, but the solubility is only slight (about
5%).
Method 2. Intimately mix 99 g (0.67 mol) of pure phthalic anhydride and 20 g (0.33 mol) of urea, and placethe mixture in a 1-litre, long-necked,
round-bottomed flask. Heat the flask in an oil bath at 130-135°C. When the contents have melte, effervescence commences and gradually increases in
vigour; after 10-20 minutes, the mixture suddenly froths up to about three times the original volume (this is accompanied by rise in temperature to
150-160°C) and becomes almost solid. Remove the heat from beneath the bath and allow to cool. Add about 80 mL of water to disintegrate the solid in
the flask, filter at the pump, wash with a little water and then dry at 100°C.
The yield of phthalimide, m.p. 233°C (i.e practically pure), is 86 g (87%). If desired, the phthalimide may be recrystallised from 1200 mL of
industrial spirit; the first crop consists of 34 g of m.p 234°C, but further quantities may be recovered from mother-liquor.
Reference: VOGEL'S Textbook of Practical Organic Chemistry (5:th edition), page 1065-1066
Accept No Imitations, There Can Only Bee One; www.the-hive.ws
Aurelius
(Hive Addict)
03-03-03 16:38
No 413473
Anthranilic Acid Bookmark
Don't know if this has been posted here before, but it's relevant to the use of the Imide:
Take the phthalimide and stir it in 25% aqueous KOH for 1-2 hours at 0*C and then acidify with HCl to give Phthalamidic acid.
This acid reacted with NaOCl gives anthranilic acid.
OR
The Imide can be reacted with basic (NaOH) NaOCl in water at 80*C and then acidified to give Anthranilic acid.
The more anthranilic acid can recovered from solution after initial separation by the use of its Cu salt.
(p 660-661 Org. Chem. 3rd ed. Fieser&Fieser)
Rhodium
(Chief Bee)
03-03-03 16:47
No 413477
Copper anthranilate Bookmark
Aurelius: It has been detailed at my page in the Quaalude FAQ, but that tidbit about copper anthranilate was new to me. I suppose it is the Cu2+ salt?
Aurelius
(Hive Addict)
03-03-03 16:57
No 413487
copper salt Bookmark
I dont' know. the book didn't state which form was used. I would suppose Cupric as it is available more cheaply in the form of CuSO4
Aurelius
(Hive Addict)
03-03-03 18:49
No 413518
Another Anthranilic synthesis Bookmark
Anthranilic acid can be synthesized by the fusion of leucoindigo with KOH at lower temperatures.
Aurelius
(Hive Addict)
03-03-03 19:34
No 413531
Anthranilic acid by hypochlorite Bookmark
Post 108807 (dormouse: "Anthranilic acid from phthalimide using OTC sodiumhypochlorite solution -Methaco(s)m", Novel Discourse)
[Edited on 6-9-2006 by solo]
It's better to die on your feet, than live on your knees....Emiliano Zapata.
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not_important
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The V2O5 catalysed method in "Fundementals of Dye Chemistry" is similar to a lab level method I've seen elsewhere. The complexity of the industrial
process comes about from the quanities used, the need to separate the reactants and products while consuming as little of other reagents as possible,
and to reach maximum overall conversion with recycle of unreacted feedstock and so one. If you're not making multi-Kg amounts, batch isolation of the
products is quite workable and much simplier than the industrial version.
You can get vanadium pentoxide from larger pottery supply sources; pick up some other glaze chemicals at the same time - K2CO3, B(OH)3, MnO2, Cu2O and
CuO, CeO2, cobalt carbonate and oxide.
The trad method using sulfuric acid and mercury catalyst is in a number of older organic chem lab books, it has the advantage that you can be busted
by both your countries drug control and evironmental agencies. The napthalene tetrachloride method might be similar, depending on local views on
haloginated hydrocarbons. Pick the one that uses the easiest to obtain acid, sulferic or nitric.
That electrolytic oxidation is likely one using cerium salts, they tend to turn out not to work well for industrial applications but will work in the
lab with a bit of tinkering. Again, pottery supply stores may stock CeO2, which can be converted to CeCl3 by refluxing with strong hydrochloric acid
with occasional additions of alcohol to help reduce the CeO2.
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unionised
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I'd have a look at phthalate plasticisers --> phthalic acid --> phthalimide before I tried oxidising C10H8
I have certainly got phthalic acid this way from shredded cheap plastic ("vinyl" rather than latex or nitrile) gloves extracted with IPA then
saponified with NaOH
BTW, in my experience CeO2 reacts very slowly with HCl, infuriatingly so.
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Nicodem
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I agree. Obtaining diethyl or dibutyl phthalate should not be difficult trough some specialized polymer resin supplier (and while ordering, buy also
some styrene). (A google search for "plasticizers+phthalate+suppliers" gives 69000 hits!)
Oxidazing naphalene sounds incredibly unpracticale and messy, not to mention stupidly expensive for such a cheap compound like phthalic acid.
Depending on use, one should also ask himself why not using something else instead of phthalimide? If using it in a Gabriel synthesis is the goal,
than there are other imides that perform just as well. For example, succinimide salts are even more nucleophilic*, though also ten times more basic.
It can be just as easily prepared from succinic acid and ammonia, with the difference that buying succinic acid should not be as difficult as phthalic
acid or phthalanhydride. One can even use saccharin in Gabriel synthesis of primary amines.
* J. Chem. Soc. Perkin Trans. II (1993) 1141- 1145.
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prole
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Thanks to all who've replied for your valuable insights and suggestions. I'm going to switch gears from utilizing mercury salts and high temps to
either the vinyl glove approach or oxidising naphthalene tetrachloride with some nitric I've got stored away. I make my own soaps, so saponification
is no mystery to me. Also, it's good to see some Hivespeak again. A bit more research, then it's off to the lab. Hurray! I'll post my results here
when they become available.
-prole
[Edited on 1-5-2007 by Polverone]
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leu
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Some citations to a few articles discussing the synthesis of tetrachloronapthalene:
Turner, Wynne, J. Chem. Soc., 1941, 247.
Turner, Wynne, J. Chem. Soc., 1941, 253.
Turner, Wynne, J. Chem. Soc., 1941, 254.
Turner, Wynne, J. Chem. Soc., 1941, 256.
Piggott, Slinger, J. Chem. Soc., 1952, 259.
Chemistry is our Covalent Bond
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not_important
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Most any vinyl object that has some flex will be plasticised. Construction sites are good as the junk piles frequently have scrap plastic pipe, which
usually is ABS, PVC, or CPVC, and perhaps sections of vinyl siding and trim. These will need to be chopped or ground up, their disadvantage vs being
free.
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leu
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The synthesis of phthalic acid from napthalene via the oxidation of the tetrachloride from Chemical Abstracts 18 1120-2
(1924):
Attachment: ca18-1120+.zip (27kB)
This file has been downloaded 1030 times
Chemistry is our Covalent Bond
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Sauron
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Phthalic anhydride is a very inexpensive compound. If your object is to make phthalimide then you will still have some work ahead of you. I made a kg
or so a few years ago as a 5-finger exercise (still around here somewhere) using three different methods, the least subtle was conc ammonium
hydroxide, but it worked. The others involved a solid mix of urea and.or ammonium carbonate IIRC. You'll need a mantle with a decent top end like a
Glas Col STM and an air condenser, the stuff wants to sublimate and you may get some phthalimide snowflakes so do it in your hood. The stuff after all
is a well known teratogen (remember Thalidomide?)
Then you need to convert to the K-salt if you are going to use this in the Gabriel.
Vogel gives good directions for a couple of these easy preps of phthalimide, I probably got the other from Org.Syn. online.
Suggestion: why not switch to o-Xylene as your starting material? That will oxidize with permanganate readily to phthalic acid or maybe the anhydride,
in either case easily converted to phthalimide. o-Xylene is cheap and unrestricted. You needn't buy a very high grade of it. Lab grade ought to do.
Maybe technical or practical grade if available. Mixed xylenes too wasteful as only the ortho will form what you want.
[Edited on 24-12-2006 by Sauron]
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guy
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| Quote: | Originally posted by unionised
I'd have a look at phthalate plasticisers --> phthalic acid --> phthalimide before I tried oxidising C10H8
I have certainly got phthalic acid this way from shredded cheap plastic ("vinyl" rather than latex or nitrile) gloves extracted with IPA then
saponified with NaOH
BTW, in my experience CeO2 reacts very slowly with HCl, infuriatingly so. |
Can you describe this a little more? I just bought some vinyl gloves. Can denatured alcohol be used instead of IPA? How does the saponification
procedure go?
Edit:
Ok so I added about 20 gloves into 200mL IPA. Heated this for a bit and stirred. The gloves became stiff and hard indicating that the plasticizing
agent had been removed. So then I added a NaOH solution to it. There are 2 separate layers but the smell of the saponified alcohol started to be
present. The smell was sweet but not pleasant and was actually quite nauseating. I wonder what it is; I think it is 2-ethylhexanol.
I haven't acidified it yet but I will tommorow.
[Edited on 3/18/2007 by guy]
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unionised
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Decant the mixed alcohols (the top layer) and acidify the lower aqueous layer. You should get a ppt of the acid you are after.
I think when I did it I used a solution of NaOH in wet ethanol so initially I just got one phase. When this reacted it gave a ppt of the Na salt of
the desired acid but I can't be sure now (it was a while ago). I added water to get 2 phases and added acid to get phthalic acid and recystalised it.
I was going to use it (as the potassium H salt) as a pH standard but (1) I couldn't get the old pH meter I got from ebay to work and (2) I decided it
would be easier to use cream of tartar.
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guy
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Ok I added HCl into the lower phase until it was acidic. Now I have a bunch of white needle crystals. Is this phthalic acid?
Edit:
Finished the box of gloves, 50 gloves. Got at least 15g. Still some more in the alcohol being precipitated out.
[Edited on 3/19/2007 by guy]
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garage chemist
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As fas as I know phthalates as plasticizers are banned in some countries or their use is at least regulated, because of various long-term health
effects.
And, please tell me you arent serious with latex gloves as a source of phthalic acid. If this is a research project as to which gloves contain the
most phthalates then fine, but if this is meant as an actual source for it then its the most ridiculous attempt at OTC chemicals that I've ever seen.
Phthalic anhydride can be obtained by absolutely everyone, there will be no objections if you order it in the pharmacy. There are countless legit uses
of it for the average science fair project (e.g. preparation of fluorescein).
I have also prepared phthalimide from phthalic anhydride, using urea melt. This worked nicely and the product was reasonably pure as indicated by the
melting point.
Athranilic acid from this did not work well however, I got dark brown gunk with too low a melting point and which couldnt be recrystallized. I think
it could be purified by forming the methyl ester, steamdistilling this and then hydrolysing it.
But this is no longer of importance, since I heard that methyl anthranilate can be bought unrestricted contrary to the acid and I got me some.
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unionised
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"And, please tell me you arent serious with latex gloves as a source of phthalic acid. If this is a research project as to which gloves contain the
most phthalates then fine, but if this is meant as an actual source for it then its the most ridiculous attempt at OTC chemicals that I've ever seen.
"
OK, I'm not serious about latex gloves because I can tell PVC from rubber. The gloves are about 50% weight phthalate; if it's the dibutyl ester then
that's about 25% phthalic acid. I have seen much worse yields than that.
I would also like to point out that this method is ridiculous in the rather odd sense that
1 it works
and
2 A couple of us have done it.
BTW, I simply don't want to be seen as "that weird bloke who orders strange chemicals" in the local pharmacy or any other pharmacy.
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guy
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| Quote: | Originally posted by unionised
"And, please tell me you arent serious with latex gloves as a source of phthalic acid. If this is a research project as to which gloves contain the
most phthalates then fine, but if this is meant as an actual source for it then its the most ridiculous attempt at OTC chemicals that I've ever seen.
"
OK, I'm not serious about latex gloves because I can tell PVC from rubber. The gloves are about 50% weight phthalate; if it's the dibutyl ester then
that's about 25% phthalic acid. I have seen much worse yields than that.
I would also like to point out that this method is ridiculous in the rather odd sense that
1 it works
and
2 A couple of us have done it.
BTW, I simply don't want to be seen as "that weird bloke who orders strange chemicals" in the local pharmacy or any other pharmacy.
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So 16g is pretty bad yield? Can you tell me how to improve the yields? This is my procedure:
50 gloves where cut up and dissolved in ~200mL of 99%IPA. This was heated to the boiling point and stirred for about 5 minutes until the plastic
became stiff.
Then I removed the glove pieces. I added a NaOH solution (in water) and shook it. I didnt't measure the amount of NaOH because I didn't know how
much ester I had. Then I separated the layer and added HCl and waited until white needly crystals precipitated.
Maybe for better yields I should use the right amount of NaOH and dissolve that in EtOH to get a more homogenous solution with the IPA.
It seems the ester used in the gloves is <a href="http://en.wikipedia.org/wiki/Di-2-ethyl_hexyl_phthalate">this</a>
[Edited on 3/21/2007 by guy]
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unionised
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How much does a glove weigh? Also, if it's the dioctyl ester the yield will be worse.
I'd try re exttracting the leftover IPA/isooctanol/whatever mixture with NaOH soln and seing if any more ester is there to hydrolyse.
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jon
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is there a way to get the pthalimide from the ester by reaction with ammonia at high temp and pressure?
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guy
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| Quote: | Originally posted by jon
is there a way to get the pthalimide from the ester by reaction with ammonia at high temp and pressure? |
Why would you want to do that though? Its seems harder. But yea, you probably can.
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UnintentionalChaos
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Another thought is that the fluid in glow sticks is the same phthalic acid ester. Im not sure if using them instead would be more cost efficient and
you avoid wasting your IPA. You would have to deal with the dye and phenol oxalate ester as well as what sounds like a significant portion of sodium
salicylate. Since the salicylate salt is very water soluble and the phthalic ester is not, a series of water extractions could also furnish the
salicylate salt for future experiments (plus the little ampoules of 35% H2O2 are probably good for test tube experiments). After hydrolyzing the
hydrophobic remains with alcoholic NaOH and then acidfying, washing the ppt should give you fairly clean phthalic acid. Anyone have glow sticks lying
around?
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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jon
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little off topic but alkali hydrolysis of leuko indigo seems to be the easiest route to anthranilic acid, it tends to easily oxidize back to indigo.
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UnintentionalChaos
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Maybe I'm just really tired, but I don't follow what you mean by alkali hydrolysis of the indoxyl. Could permanganate crack the pyrrole ring in the
right place (Seeing as how it breaks napthalene)? You could sulfonate the indigo first so it is at least soluble (still not very soluble 1g/100ml). I
am not very experienced in organics (next semester) so I could be making no sense right now and wouldn't know it.
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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jon
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lueko indigo looks like two indole rings fused together with a hydroxy group on each ring, you can get a structure of it in wikipedia, if you look
close you'll see what a handy precusor it could be.
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UnintentionalChaos
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Ah, found it on the German page. The english has either leucoindigo or indigo white meaning the same thing. It's an ethylamine short of tryptamine, if
that is what you mean, though I am not interested in that area. I assume that anthranilic acid can be used to make tryptamines and that is why it is
watched, but my point was, if you wanted anthranilic acid from indigo for the heck of getting anthranilic acid, could permanganate get you there?
guy- I also did an extraction (though have not saponified it yet) of 12 gloves which lost about 30% of their mass after extraction. This seems like
too even a number to be a mistake. I used 12 "Mr. Clean" vinyl gloves , shredded and washed them to remove the powder, and left overnight in denatured
alcohol (roughly equal parts methanol and ethanol and 1-4% of methyl isobutyl ketone). I should get roughly 6.9g phthalic acid if yield is perfect and
if your gloves were identical, you would have recovered almost 28.8g. Did you manage to improve your yields any?
[Edited on 3-24-07 by UnintentionalChaos]
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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