Sciencemadness Discussion Board

Dichloroacetic acid source?

Crowbar - 25-5-2015 at 10:47

I need a small amount of dichloroacetic acid for personal use as a chemical cauterizing agent. I'm wondering about the possibility to synthesize or extract some from materials available to a layman. I can probably get an (impure) salt form as DCA pills which tend to be sold by online scammers as an overhyped anticancer agent, but wouldn't know how to convert to a concentrated acid.

[Edited on 25-5-2015 by Crowbar]

adk - 25-5-2015 at 14:56

Alfa Aesar sell it. Where are you located?

https://www.alfa.com/en/catalog/A14740

aga - 25-5-2015 at 15:05

What would one use dichloroacetic acid for ?

Oh. A quick google brings up certain cancer references.

Please tell more if you can/are wiling.

One Synthesis document i came across :-

http://www.orgsyn.org/demo.aspx?prep=cv2p0181

AvBaeyer - 25-5-2015 at 18:43

Elemental Scientific sells it.

AvB

Crowbar - 26-5-2015 at 03:30

Thanks for these recommendations.
aga: as I mentioned, it's a cauterizing agent. Certainly cheaper/easier than buying/building an electrocautery machine.

adk - 26-5-2015 at 03:41

Quote: Originally posted by Crowbar  
Thanks for these recommendations.
aga: as I mentioned, it's a cauterizing agent. Certainly cheaper/easier than buying/building an electrocautery machine.


Keep in mind that almost all chemical suppliers do not sell materials suitable for therapeutic use. Caveat emptor.

Loptr - 26-5-2015 at 06:22

Quote: Originally posted by Crowbar  
Thanks for these recommendations.
aga: as I mentioned, it's a cauterizing agent. Certainly cheaper/easier than buying/building an electrocautery machine.


Yeah, I would never use something I purchased for a lab supply for oral, internal, or topical use, unless it was certified USP-grade or equivalent. Even then, I would just go to the pharmacy or my doctor in order for then to tell me what the suggested alternative would be in my particular situation.

I am curious as to why you would need cauterizing tool? Do you plan on have to cauterize a lot of trauma wounds? :o

ledob86 - 26-5-2015 at 10:10

If you want more ref. the merck index :

Literature References: Transformation of chloral to dichloroacetic acid: Wallach, Ann. 173, 288 (1874); Frantzen, Fikentscher, ibid. 623, 68 (1959); Rosenblum et al., Chem. & Ind. (London) 1960, 718. Toxicity: Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951); P. W. Stacpoole et al., N. Engl. J. Med. 300, 372 (1979); J. L. Cicmanec et al., Fundam. Appl. Toxicol. 17, 376 (1991). Mutagenicity studies: V. Herbert et al., Am. J. Clin. Nutr. 33, 1179 (1980). Use in treatment of lactic acidosis: P. W. Stacpoole et al., N. Engl. J. Med. 309, 390 (1983).

aga - 26-5-2015 at 12:21

Interest piqued.

Self-surgery ?

Also, how does DCA work as a cauterising agent ?

If it clots the blood fast, then great.

That sounds a lot better than burning both blood and tissues - it/the products will eventually be disposed of by the body, presumably faster than new cell growth occurs.

Edit

New cell growth obviously will have to occur in either case.
It would be interesting to know which heals faster.

[Edited on 26-5-2015 by aga]

Crowbar - 22-6-2015 at 12:45

What prompted my question is that I've have a few recalcitrant plantar (base of foot) warts for around four years. The usual topical salicylic acid did not work, and neither did cryotherapy (freezing them) at the doctor's office. I've also tried to cut them out, though it only takes a few infected cells remaining to result in the warts growing back. I also tried concentrated nitric acid. Nice yellow stain and a good deal of pain, but despite the destruction of tissue, they still grew back.

One of the big issues is that warts have a heavy blood supply, which tends to quickly dilute away whatever chemical agent penetrates below the surface. This is why one of the treatment modalities I've read about is laser tuned to cook capillaries at a depth of a couple of mm.

In my area, finding a doctor who has access to immunotherapy (topical Candida antigen or diphencyprone, or injected interferon) is not likely (there's not a lot of choice in socialized Canadian medical care :( ), and these are agents I would not be able to purchase myself. If I find some poison ivy, that might work, but as I in general have no allergies, I may not be immunosensitive to it. Blistering agent (Bleomycin) is an option, but I won't be able to walk for a good period.

I also came across a French wart treatment which contains a combination of nitric and several organic acids and some metal salts. The patent claims that this functions not by caustic action of the nitric acid, but by generating NO2 which denatures cellular proteins but, critically, does not penetrated the dermoepidermal junction. This means it won't damage tissue below the wart. I can't get this treatment here, but it gave me the idea to try to expose my warts to concentrated NO2, which would be a difficult setup to carry out for more than a few minutes (which may not cut it).

I was thinking as a last resort to get electrocautery at a podiatrist's office, but that pretty much guarantees scars. I'm also looking at some cream sold online which has a mix of cashew nutshell oil extract and greater celadine sap, which are both strong dermatogens and the latter is a cauterizing agent. But I'd rather not spend the $ and risk it not getting across customs (since cashew nutshell derivatives are restricted exactly because they cause contact dermatitis).

Right now I'm trying 5-fluorouracil because it inhibits DNA replication, and the viruses causing warts are DNA viruses. I alternate it with strong salicylic acid to remove excess tissue. It reduces the warts (unlike salicylic acid by itself, which seems unable to cope with the otherwise fast infected tissue growth), but it's pretty much impossible to know when to stop, because I can't tell when I've reached the dermis. I thought I had at one point, because I got to tissue that was uniformly red (as opposed to the light colored wart tissue with interspersed red capillaries); yet, when I stopped applying, they grew back.

I can't say I haven't fantasized about amputation...

[Edited on 22-6-2015 by Crowbar]

Boffis - 22-6-2015 at 14:22

The simplest home route to dichloroacetic acid is by the reduction of trichloroacetic acid (easily available from ebay suppliers) with metallic zinc or copper. I'll dig out the reference later but I think its in J Amer Chem Soc. Basically copper powder was used and the copper in solution precipitated with H2S and concetrated. The metal dissolves in trichloroacetic acid without the evolution of gas to give a solution of copper chloride and copper dichloroacetate. If you don't like working with H2S then you could try powdered zinc and use strong HCl to liberate the free acid and distill, or neutralise with sodium carbonate solution and remove the zinc carbonate by filtration and then acidify and distill.

Attachment: Preparation of Dichloroacetic acid from trichloroacetic acid JACS Doughty & Derge 1931.pdf (204kB)
This file has been downloaded 515 times

CuReUS - 23-6-2015 at 05:48

I have a better method.react HOCl(bleach) with acetylene to get dichloroacetaldehyde,then oxidise aldehyde to acid using oxone or NaClO2(pinnick oxidation)
http://nsdl.niscair.res.in/jspui/bitstream/123456789/777/1/R...-acetylene +HOCl
https://en.wikipedia.org/wiki/Pinnick_oxidation
http://pubs.acs.org/doi/abs/10.1021/ol0340078 oxone oxidation

Boffis - 24-6-2015 at 09:39

@CuReUS I don't want to get into an argument about which route is the better but...

Having read some of the threads on SM on the use/preparation of free hypochlorous acid its isn't that easy and my own experiment into the used of "neutral" hypochlorite solution have proved tricky; fine pH control is necessary or yields become very erratic. Furthermore gas-liquid reactions in which the gas has a low solubility in the solvent tend to be slow or very low yielding since much gas is lost. Have you actually tried this reaction? If so could you post details please.

The oxidation with oxone (K monopersulphate +KHSO4 & K2SO4) or sodium chlorite look "home chemistry friendly" enough though.

One last point is how stable is the dichloroacetaldehyde? the monochloro derivative is supplied as the more stable diacetal because the free compound polymerises.

aga - 24-6-2015 at 10:51

Quote: Originally posted by Boffis  
gas-liquid reactions in which the gas has a low solubility in the solvent tend to be slow or very low yielding since much gas is lost

Trap the gas in a balloon or rubber glove to keep the reactants in close contact.

Eliminates the need to produce then destroy loads of gas, and makes it all a bit safer.

Worked fine for me to contain chlorine whilst making S2Cl2.

Sure, the balloon is no longer party-grade afterwards, but they're cheap, and come in bags of at least 10.

CuReUS - 25-6-2015 at 04:46

Quote: Originally posted by Boffis  

Have you actually tried this reaction? If so could you post details please.

No I haven't done it.I was searching for something else when I stumbled upon it.I was amazed how easily the dichloro acid could be made.
Quote:
Furthermore gas-liquid reactions in which the gas has a low solubility in the solvent tend to be slow or very low yielding since much gas is lost.

spice boy's KRV(ketone reaction vessel) comes to mind;)
Quote:
One last point is how stable is the dichloroacetaldehyde? the monochloro derivative is supplied as the more stable diacetal because the free compound polymerises.

you got me there.Just a few days back,I had read that bromoacetaldehyde was a bad chemical to work with,but no explanation was given.Now I think the polymerisation is to blame.But a one pot synthesis could eliminate that problem(the dichlroacetaldehdye formed could be immediately oxidised to the acid,instead of purifying it.)

one more thing.If you are going to buy trichloroacetic acid,why don't you just buy dichloro;)


[Edited on 26-6-2015 by CuReUS]