Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Cyanoform and derivates
Hazard to Others

Posts: 496
Registered: 16-2-2012
Member Is Offline

Mood: No Mood

[*] posted on 8-6-2023 at 09:36
Cyanoform and derivates

Cyanoform was for over a century a notoriously missing substance. While cyanoform salts could be produced and production of cyanoform from its salts was tried already by 1896 - what are the easiest synthetic routes to sodium cyanoformide? - it always decomposed on separation.
Cyanoform was finally separated in 2015. And that was duh. Cold hydrofluoric acid. Decomposes at -40 C. Handling cold acids should have been a standard technology. A 1960 preparative inorganic chemistry includes synthesis for thiocyanic acid, that decomposes at -85 C.

What other cold acids are good to produce cyanoform?(Fluorosulphonic? Chlorosulphonic? Hydrochloric?)

Another related substance, for which I could not figure out a name which would return consistent useful references is HC(COOH)3. What is it called?

And other substances in between - HCCN(COOH)2 and HCCOOH(CN)2. How are they called? How labile are they?
View user's profile View All Posts By User
International Hazard

Posts: 5098
Registered: 1-11-2003
Location: UK
Member Is Offline

Mood: No Mood

[*] posted on 8-6-2023 at 13:52

I don't know if methanetricarboxylic acid exists, but you can buy its ester.

Getting back to cyanoform, the synthesis starts with sodium tricyanomethanide.
But does anyone know how you get that?
View user's profile View All Posts By User
National Hazard

Posts: 757
Registered: 30-12-2018
Location: not so United Kingdom
Member Is Offline

[*] posted on 10-6-2023 at 15:29

I, too, was curious how sodium tricyanomethanide could be made. I hypothesised reacting chloroform with sodium cyanide in alkaline condition to deprotonate the tricyanomethanide as soon as it forms.

I searched for a procedure and found a patent that reacts malononitrile with cyanogen chloride. Melononitrile can be prepared by reacting cyanogen chloride with acetonitrile. I guess you could go directly from actonitrile to sodium tricyanomethanide.

Here is the patent:

Attachment: metal-tricyanomethanides-EP2674416A1.pdf (208kB)
This file has been downloaded 111 times

Please note this procedure is potentially very dangerous, I don’t recommend anybody try it.

[Edited on 6/10/2023 by wg48temp9]

I am wg48 but not on my usual pc hence the temp handle.
Thank goodness for Fleming and the fungi.
Old codger' lives matters, wear a mask and help save them.
Be aware of demagoguery, keep your frontal lobes fully engaged.
I don't know who invented mRNA vaccines but they should get a fancy medal and I hope they made a shed load of money from it.
View user's profile View All Posts By User

  Go To Top