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quest
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[*] posted on 20-6-2005 at 01:39
Gallic acid from trees


Gallic acid is very expensive to buy so I'm looking for a ceap and easy synthesis for it.

http://www.encyclopedia.com/html/g1/gallicac.asp
In this site it wrote you can synthesis it from oak bark, sumach - and many other plants

But as for how I can synthesis it from this plants, and from where can I collect the most gallic acid it didn't say.

So can any one help me with this synth? how can I make my own gallic acid?

thanks
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sparkgap
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[*] posted on 20-6-2005 at 02:44


IIRC, gallic acid does not occur free in trees; rather, it is combined chemically with other stuff in plants to form the lignins, tannins, and other polyphenolic principles. I think hydrolysis might work, but I'm not really sure. Maybe the ones who have better knowledge in plant biochemistry might have better suggestions? ;)

sparky (~_~)

P.S. The only difficulty I can forsee is that there are (or may be) enzymes, IIRC, that can catalyze oxidation of phenolics in plants that are oxygen-activated.

P.P.S. Heh, thanks Lambda, didn't know about those "whistles". ;)

[Edited on 20-6-2005 by sparkgap]




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Lambda
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[*] posted on 20-6-2005 at 02:45
Would you like a cheap whistle ?


Dear Guest, if you are looking for a loud whistle composition, then Sodium salicylate and Sodium benzoate will work fine. Salicylic acid and Benzoic acid are cheap and easilly obtainable.

You may get the sodium salt by nutralizing the free acids with a basic sodium salt like sodium hydroxide. Sodium hydroxide is widely used as a unblocking agent for kitchen sinks.

Benzoic acid:
http://en.wikipedia.org/wiki/Benzoic_acid
http://www.chemicalland21.com/arokorhi/industrialchem/organi...

Salicylic acid:
http://en.wikipedia.org/wiki/Salicylic_acid

Sites refering to pyrotechnics:
http://www.reference.com/Dir/Science/Technology/Pyrotechnics...

Practical Pyrotechnics: Home page of Wouter Visser
http://www.wfvisser.dds.nl/indexEN.html


A collection of pyrotechnic compositions (please refere to chapter 6 for whistle compositions):
http://www.wfvisser.dds.nl/compoDB.html

However, if you insist on making Galic acid, then you may check this out:
http://en.wikipedia.org/wiki/Gallic_acid
http://www.greatvistachemicals.com/industrial_and_specialty_...

Gallic acid is found in gallnuts, sumach, tea leaves, oak bark, and many other plants, both in its free state and as part of the tannin molecule.

Due to the irratic burning of whistle compositions, sound is produced. These compositions are not only very sensitive to friction, but allso extremely dangerouse. They are all powerfully explosive. The Gallic acid compositions are particulary dangerouse, and are thus best avoided.
Quote:
Have a good and loude whistle !


[Edited on 20-6-2005 by Lambda]
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[*] posted on 20-6-2005 at 03:10


Lambda, I'm indeed want the gallic acid for whistle composition.
I know the danger in this comps and I'm not going to mass prduce it - only try some small portion.

The gallic acid/P-chlorate is said to have the loudest whistle. :)

Most of the other formulas use P-perchlorate , and I can't get this chem

So I'm still want to synthesis Gallic acid.
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[*] posted on 20-6-2005 at 03:23


If you've checked the price of gallic acid, have you also checked the price of gallate esters? If they're cheaper, maybe you can saponify them and get gallic acid.

BTW, browsing through Rhodium, I discovered that gallic acid can be used for making mescal alkaloids, so I might think it's watched. Can anyone verify?

sparky (~_~)




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[*] posted on 20-6-2005 at 07:42


I've been wondering about this too. Tannins (esters with glucose or other more complicated structures) apparently are in great abundance in galls (the little wart looking things on leaves), hence the name gallo-tannic acid or gallic acid itself. Should be able to hydrolyze it with lye then crystallize the salt. I wonder how many other organic acids will come along for the ride, though.

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blazter
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[*] posted on 20-6-2005 at 18:01
Too bad the hive still is down


Back when the Hive was in operation, apparently someone named Halfapint was trying to come up with a viable synthesis of mescaline starting from mountain ash wood and producing gallic acid from that. Unfortunately Halfapint is no longer among the living, since his obituary was posted on the Hive as well. Apparently he was able to get the synthesis started, but was unable to separate out the Gallic acid from the mess that was produced from digesting the wood IIRC.

In any case, if someone could figure out a decent way to go from wood to gallic acid, mescaline is not that far away. I also seem to remember some references that were posted on the hive about some researchers who managed to extract some gallic acid, but I have no idea what it was now.
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[*] posted on 20-6-2005 at 20:39


The acid is not the most convenient precursor, so it would be unwise for LE/govt to watch this. Though of course, wise people need not apply for LE/govt positions.

Cheap sources of tannins that were found with Froogle last year are no longer found or not cheap. Well, its out there somewhere, and if not from a chemical supplier as tannic acid, then as a species(color)-specific tannin for use as a mordant.

There is difference in the hydrolysis products depending on the plant source, so pay attention to that if reasonably pure gallic acid is particularly important. I recall a CA abstract where tea tannin was methylated in the usual way with methyl sulfate, giving equimolar amounts of 3,4 and 3,4,5 trimethoxy benzoic acids.

Thorpe's Dictionary is old but still very much worth downloading. So what are you waiting for? This is what was written about tannins:

http://rapidshare.de/files/2516052/adoac_tannin.djvu.html
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[*] posted on 20-6-2005 at 21:09


An excellent 116 page pdf on tannins:
http://www.users.muohio.edu/hagermae/tannin.pdf

Sources of tara pod powder used to be easier to find as well. I found this, probably from the Hive, on gallic acid from tara:

[Edited on 21-6-2005 by S.C. Wack]

Attachment: tara.pdf (218kB)
This file has been downloaded 1236 times

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Lambda
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[*] posted on 20-6-2005 at 22:11
Extraction of gallic acid from tara powder.


Extraction of gallic acid from tara powder

Tara powder (40 kg: 9% moisture) was extracted for 6h with demineralized water (1:10w/v) at 60°C. The extract was vacuum filtered through celite and concentrated under vacuum at 60°C to one tenth of its original volume. Hydrolysis was carried out with 48% NaOH (1:1.5v/v) for 6h at 102°C. The solution was cooled at 30°C and neutralized with 60% H2SO4 . Adjusting pH at 2 and cooling to 10°C initiated crystallization of crude gallic acid (11 kg). Recrystallization from demineralized water with activated carbon (3: 11 w/w) afforded pure gallic acid (8.9 kg: 97% HPLC purity; 1.48 % moisture content and 25 % yield from tara powder. anhydrous base).
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[*] posted on 20-6-2005 at 22:28
Galluszuur (dutch)


Galluszuur

100 g Chinese galappels wordt fijngebroken en met 300 ml zwavelzuur van 20 % 15 min lang gekookt. Het hete reactieprodukt wordt gefiltreerd, de rest met heet water uitgewassen. De heldere oplossing laat men afkoelen en enige dagen rustig staan. Het galluszuur is in 3 delen heet water en slechts in 130 delen koud water oplosbaar; het kristalliseert na het afkoelen langzaam uit. Waneer de hoeveelheid afgescheiden galluszuur niet meer toeneemt, wordt het zuur afgefiltreerd en onder toevoegen van iets dierlijke kool uit heet water omgekristaliseerd. Een betere opbrengst verkrijgt men door 100 g gebroken Chinese galappels met 1 g gewone bakkersgist en weinig water tot een dune pap aan te roeren. Het mengsel laat men bij 20 - 30 graden celcius staan, waarbij het begint te gisten. Van tijd tot tijd neemt men een kleine proefje, filtreert de oplossing af en voegt iets verdunde lijmoplossing toe. Hierbij mag slechts zeer weinig neerslag gevormd worden. Zodra dit het geval is, hetgeen gewoonlijk einige weken duurt, voegt men de 6-voudige hoeveelheid water toe, kookt even op en filtreert. Uit het filtraat kristalliseert dan langzamerhand het galluszuur uit. Het wordt door omkristalliseren gereinigd.

Bron:
Chemische preparaten.
Drs. L. P. Edel.
Derde druk (1965).
N. V. Uitgeversmaatschappij Kluwer.
Deventer / Antwerpen.
(pagina 243).

Opmerkingen:
lijmoplossing = beenderlijm (?).
Dierlijke kool = Actieve koolstof (vervanging).

Galluszuur:
3,4,5-Trihydroxybenzoezuur.
Mol.gew. 188.13
Verliest kristalwater bij 100 - 120 graden celcius.
Smpt 225 - 250 graden celcius onder ontleding.
S.g. 1.694

Bereiding:
Koken van galnotenextract of tannien met verd. zwavelzuur.

Tannien:
Komt voor in de bast van vele planten, vooral quebracho, mimosa, mangrove, melock, berk, eikenbast, canaigre, gambir, cutch, knoppern, zeer veel (tot 70 %) in gallen, afkomstig uit China of Turkije, en de zamenstelling wisselt.

Quote:
Will be translated from Dutch to English soon !
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[*] posted on 21-6-2005 at 06:27
WHISTLE MIXTURES


Whistle mix #1 [1] [4]
Potassium perchlorate.........................................70
Sodium benzoate...................................................30

Whistle mix #2 [2]
Potassium chlorate................................................75
Gallic acid.................................................................25
Comments: This mixture is quite sensitive to friction and shock.

Whistle mix #3 [3]
Potassium chlorate................................................40
Sodium chlorate......................................................10
Potassium nitrate....................................................30
Sodium salicylate....................................................10
Paraffin oil.................................................................10
Ferric oxide................................................................+0.2

Whistle mix #4 [4]
Potassium perchlorate............................................72.5
Sodium salicylate.....................................................27.5
.
Whistle mix #5 [4]
Potassium nitrate......................................................30
Potassium dinitrophenate.......................................70

Source:
[1] T. Shimizu, "Fireworks: The Art, Science and Technique", Pyrotechnica Publications, Austin, Texas, USA (1981).
[2] R. Lancaster, "Fireworks, Principles and Practice", Chemical publishing Co., Inc. New York (1972).
[3] Composition from Oztap.
[4] H. Ellern, "Modern Pyrotechnics", Chemical Publishing Co., Inc. New York (1961).
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[*] posted on 8-1-2006 at 12:25


Hi all,

I have been tinkering with a whistle mix... I think it corrisponds to mix #4 on this page.

Is there a specific size for the hole/tube to press it into? Also, how hard (how much pressure) do you use to press it? Could you use a C clamp to press it into holes drilled into a 2X4? Can it explode while being pressed? Does the particle size matter a lot with this mix?

I made my sodium salicylate by neutralizing salicylic acid with NaOH, followed by drying and grinding.

I had KClO4 on hand.

The mix burns well (pretty fast), with a yellow flame and a dense white smoke.

Thanks
Endo
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[*] posted on 26-4-2006 at 20:12


2 things.... The below exert is about producing gallic acid from TARA powder(fermintation). The article mentions that gallic acid can be hydrolysized from sulfuric acid and tannic acid. I was wondering if anybody is willing to spare a procedure and if Sodium Hydroxide would work to? This exert vaguely covers both processes.



Gallic acid (3,4,5 –trihydroxybenzoic acid) is a useful chemical with wide applications. It is utilized in the production of trimethoxy benzaldehyde, which is used in the ink industry, dye industry and and most importantly, pharmaceutical industry. In pharmaceutical industry 3,4,5 trimethoxy benzaldehyde is converted to trimethoprim, a broad spectrum antibiotic. A combination of trimethoprim and sulphonamide is effective against many otherwise resistant species of bacteria. Though technological advances have introduced many new antibiotics in the market, trimethoprim is still very significant. In combination with sulphonamides, it is highly effective against many drug-resistant species of bacteria. Of the total requirement of gallic acid of 8000 tons per year, ¾ part is used in the production of trimethoprim. The export of trimethoprim is approximately 450 tons per annum. Considering this, it is important to have an economical indigenous technology for its commercial production. A cost-effective indigenous technology for gallic acid using low-cost raw material can contribute significantly to this. Gallic acid can also be used as a raw material for manufacturing an intermediate for antioxidants, preservatives like propylgallate.

Conventionally gallic acid is produced by the Acid Hydrolysis of tannic acid. It involves acidification of tannic acid with sulphuric acid (10% of the total volume) at a high temperature (110oC – 120oC). This technology has several disadvantages. Yield of gallic acid is only 28-33% of the total tannic acid. Since the process involves heating of tannic acid at high temperature and low pH, corrosion takes place. So recurring cost incurred in equipment investment is high. The purity of the product is also not high because tannic acid extracts are always rich in sugars, resins, gums etc. Acid hydrolysis causes degradation of these polymers as well as sugars. In the final process of crystallization, many of these degraded products interfere and precipritate along with acid. Gallic acid thus produced is unsuitable as a raw material for the manufacturing of drug intermediates.

Achievements

The process of fermentation of tannic acid extracted from tara powder was developed to 100 litre/ batch level, and it gives good yield of gallic acid (90% of available tannic acid) with minimum energy input as compared to acid hydrolysis process. Purity obtained is high (98%). Tara powder being available at low price, production of gallic acid in this process is economical as compared to conventional process.

About the Company

M/s Hi-Tech Bio Laboratories is a contract research organization working in the field of Bio Technology from several years. They have developed several technologies successfully for the industries. Also, they have started a Pvt Ltd. company in the name of Sci Molecules India Pvt.Ltd., a dedicated research & development company recognized by DSIR. The financial performance of the company during the last few years has been as follows:
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[*] posted on 28-4-2006 at 00:14


Quote:
Originally posted by S.C. Wack
Thorpe's Dictionary is old but still very much worth downloading. So what are you waiting for? This is what was written about tannins:
http://rapidshare.de/files/2516052/adoac_tannin.djvu.html

That link is broken.
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[*] posted on 8-5-2006 at 13:49
gallic acid and whistle composition


One thing to watch out for: gallic acid absorbs oxygen at the slightest provocation. The quoted extraction process (from tara tannin) uses many Kg and was probably done in a closed reactor. Gallic acid was used to test the oxygen content of boiler water and air. It's impressive - shake a 15 ml test tube with a little gallic acid solution and air in it with your thumb over the end for a few seconds. Stick the closed end under water and release your thumb. 20% of the air space fills with water.

According to the literature, it's tricky to hydrolize tannic acid to gallic acid with an acid catalyst. The 3,4,5 OHs come off. That's why the procedures sometimes call for protecting them with methyl sulfate. The alkaline hydrolysis doesn't cause this degradation so no protection need be added.

In the US, I'm told that it's inadvisable to have 3,4,5 trimethoxyphenols about without a good lawyer under retainer. It's not controlled, but you'd better have a good reason to have it.

Look up Selcuk Otzap (with a cedilla on the c and an umlaut on the O) for definitive articles on pyrotechnic whistles. In short, whistle mixtures are very sensitive and when confined come close to crossing from deflagration into detonation. Mr. Otzap, the world authority on these things, was killed a few years ago in an explosion. He invented compositions incorporating paraffin or vaseline to reduce the sensitivity and ease of construction.

Useful whistles generally use 3/16" to 1/2" thin walled paper tubing (say 4mm to 13mm). Press (do not pound or hammer) the composition tightly and densely into the tubes. If there are any air pockets the whistle will explode.
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[*] posted on 8-5-2006 at 17:16


Hmmm... Thanks for the heads up. I have plenty of sodium hydroxide so this should not be an issue.

I see that most of the whistle compositions require potassium chlorate/perchlorate. I was wondering if potassium nitrate could be subsituted for the ClOx oxidizer.
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[*] posted on 14-5-2006 at 15:12


@DeAdFX:
IMnsHO, if you want to make pyrotechnic whistles, salicylates, benzoates, and terephthalates would do just as well as gallic acid. In general, authorities agree that gallic acid is not enough better than the previously mentioned aromatics to be worth the trouble.

Unfortunately, AFAIK, you need chlorates or perchlorates for the whistle to work. One explanation of the whistle is a series of detonations which extinguish themselves and are reignited by the pressure wave reflecting from the open end of the tube. It's pretty hard to get a detonation out of a nitrate (though barium nitrate might work).
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[*] posted on 4-2-2007 at 13:29


A little off topic but can the whistle mix consisting of KClO3 and C6H5COONa be made with KBrO3 instead of the KClO3?



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[*] posted on 5-2-2007 at 08:47


I believe the usual entry point for these 3,4,5-trimethoxy compounds is the photographic chemical pyrogallol.

You've got to methylate those three phenolic groups which is a pain and requires you to work with strong methylating agents renowned for being brain carcinogens (dimethyl sulfate, iodomethane, etc.) But there you are.
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