06-25-03 22:17
No 442513
I've looked through TFSE, and everyone seems to agree that trioxane can be used in place of paraformaldehyde in the NH4Cl+Paraformaldehyde synth for methylamine. I also saw a ref where it was used for chloromethylations. My question is, does anyone have any actual, real-life success stories using trioxane in either the methylamine synth or a chloromethylation?
It is seductive, way too seductive. -Eleusis
(Chief Bee)
06-26-03 03:23
No 442563
(Rated as: good read)
Trioxane (1,3,5-Trioxymethylene:
) seems to be a perfectly good (para)formaldehyde substitute, among other things as a source od the methylene unit (-CH2-) in chloromethylation of aromatics. See the following articles for details:
Kinetic Equation for the Chloromethylation of Benzene with Trioxane and Hydrogen Chloride Using Zinc Chloride as a Catalyst
Ind. Eng. Chem. hod. Res. Dev. 21, 87-93 (1982) (../rhodium/pdf /chloromethyl
Chloromethylation of Benzene and Alkylbenzenes with Bis(chloromethyl) Ether, 1,4-Bis(chloromethoxy)butane, 1-Chloro-4-chloromethoxybutane, and Formaldehyde Derivatives
J. Org. Chem., Vol. 41, No. 9, pp. 1627-1631 (1976) (../rhodium/pdf /chloromethyl
Trioxane as a Source of Formaldehyde
Ind. Eng. Chem. 39(8), 974-977 (1947) (../rhodium/pdf /trioxane-for
(Hive Addict)
06-26-03 16:05
No 442683
Chloromethylation of Benzene and Alkylbenzenes with Bis(chloromethyl) Ether, 1,4-Bis(chloromethoxy)butane, 1-Chloro-4-chloromethoxybutane, and Formaldehyde Derivatives
So am I correct in thinking that all they did in this ref was do a normal chloromethylation, but use GAA as the solvent, trioxane as the formaldehyde source, and SnCl4 as the acid catalyst, and then just bubble in HCl as usual?
I like this little idea, considering that trioxane can be had in the form of fuel tablets for about $15US for 3.5kg.
It is seductive, way too seductive. -Eleusis