https://www.thevespiary.org/rhodium/Rhodium/chemistry/eleusis/methylamine27.html#Hexamine (https://www.thevespiary.org/rhodium/Rhodium/chemistry/eleusis/methylamine27.html#Hexamine)
Under hydrolysis of Hexamine. I started at the adding 140gms of hexamine to the acid. I also didnt used any heat during the 16 hr mixing period. It doesnt say to.
I want to allow myself to link to this post of mine:
Post 488683 (https://www.thevespiary.org/talk/index.php?topic=9498.msg48868300#msg48868300)
(Organikum: "For the vindication of Eleusis - Methylamine", Methods Discourse)
Please read the whole thread - nice picture in one of the followup posts!
These ratios:
100g hexamine
100g water
310g HCl 30%
100g ethylalcohol denat.
20g ammoniumchloride
Extraction by IPA yields 120g+ methylamine.HCl in clear colorless crystals (theory: 145g).
Washing with chloroform showed that dimethylamine was only present in traces if at all.
Hexamine is a charm in my opinion as it represents an ultracompact nonsmelling unsuspicious source of formaldehyde and ammoniumchloride (1mol hexa with 4mole HCl gives 4mole ammoniumchloride and 6mole formaldehyde... whatta want more?)
The ethylformate produced (about 3mole per 1mol hexamine) dissociates in water into EtOH and formic acic, but who needs formic acid.... ;D
Please dont poison yourself and your environment with this frypan-evap-shit procedure. It is a simple reflux/distillation setup for clean product and zero smell.
Actually, I too made the mistake of forgetting to add water (just alcohol, hexamine and acid) - noticeable exotherm reaction, placed it in a water bath and was just about to start slow heating - suddenly I remembered there was still a reactant missing! I then added the water immediately, continued as if nothing had happened (2h reflux, 3.5h distillation of ethylformate, reflux 1h, alcohol removed using vacuum) and got still good yield...
(but also got some strange white substance, insoluble in acetone/alcohol/water - it appeared after alcohol removal, was filtered and found to be hard, crunchy and not crystalline. I suspect it to be something similar to hexamethylene(triperoxide)diamine or HMTD, see also Post 512495 (https://www.thevespiary.org/talk/index.php?topic=9498.msg51249500#msg51249500)
(armageddon: "explosive by-product?", Methods Discourse)
Greetz A
This seems to be the right thread for posting this:
Methenamine
CAS 100-97-0; 587-23-5; 5714-73-8
(Formamine, Hexamethylenetetramine, HMT, HHMTA, Methenamine, Urotropine)
full name: 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane
or: 1,3,5,7-tetraazaadamantane
Made by reacting formaldehyde and ammonia:
6 CH2O + 4 NH3 ---> HMTA
see also Patent US2763799 (http://l2.espacenet.com/dips/viewer?PN=US2763799&CY=gb&LG=en&DB=EPD)
and Patent US2762800 (http://l2.espacenet.com/dips/viewer?PN=US2762800&CY=gb&LG=en&DB=EPD)
Hexamine is commonly used as an urinary antisepticum, and it is sold under the brand names:
Aci-Steril, Antihydral, Hiprex, Mandelamine, Prioherp, Urotractan (germany)
Aromalgyl, Formocarbine (france)
Hiprex, Mandelamine (GB)
Elmitolo, Jodoibs (italy)
Hexamine (japan; they apparently don't like trade names :P )
Uro-Phosphate, Hiprex, Urex, Mandelamine, Thiacide, Uroquid-Acid (USA)
In case you dislike your pharmacist ;) :
Well branded fuel tablets are said to contain 99.9% hexamine, too...
..and are WAY cheaper..
Greetz A