Mixtures tetramine

Hexamethylene tetramine (77 g., 0.55 mole) is dissolved in 200 ml. of chloroform, and 88 g. (0.5 mole) of 3-thenyl bromide (p. 96) is added as rapidly as possible with shaking (Note 1). A reflux condenser is attached, and the mixture is refluxed over a steam bath for 30 minutes. After being cooled, the mixture of chloroform and crystalline product (Note 2) is poured into 250 ml. of water and stirred until all the salt dissolves. The chloroform layer is separated and washed twice with 125-ml. portions of water, and the combined water extracts are steam-distilled. When the distillate comes over clear (about 1 1. of distillate is usually collected), it is acidified with a little hydrochloric acid (Note 3) and extracted with three 100-ml. portions of ether. After drying over Drierite, the ether is evaporated, and the residue is distilled. 3-Thenaldehyde is collected at 72-78°/12 mm. or 195-199°/744 mm., = 1.5860 (Note 4). The yield is 30-40 g. (54-71%). 

Bachmann A process for making the explosive RDX. Hexamethylene tetramine is nitrated in acetic acid solution, using a mixture of ammonium nitrate and acetic anhydride. Invented by W. E. Bachmann at the University of Michigan during World War II. See also KA, Woolwich. 

Preparation of 3.5-dimethvl-4-hvdroxvbenzaldehvde. A mixture of 40.6g (0.33 mole) of 2-6-dimethylphenol and 46.2g (0.33 mole) of hexamethylene tetramine was covered with 500ml trifluoroacetic acid and the reaction mixture was refluxed overnight. After evaporation of the trifluoroacetic acid the residue was poured into 3L water and neutralized slowly with sodium carbonate. A brown oily solid was... 

The electrical mobilities of ions in aqueous mixtures are difficult to interpret because the ionic mobility may change as a result of changes in water-structure brought about by the co-solvent and it may also change because the additive simply obstructs the passage of ions. Nevertheless, several studies have shown that the first of these two contributions can be identified. For example, structure enhancement by added hexamethylene tetramine leads to a fall in ionic mobilities for KC1 in water (Barone et al., 1968). Ionic mobilities have been measured for a variety of salt solutions in ethyl alcohol + water (Lee, 1974), THF + water (Renard and Justice, 1974) and for... 

The classical method of production (Henning, 1898) is the nitration of hexamethylene tetramine (C6H12N4) to Hexogen (C3H606N6) using concentrated nitric acid the concentrated reaction mixture is poured into iced water, and the product precipitates out. The structural formula shows that three methylene groups must be destroyed or split off by... 

K process (inventor Knottier) an increased yield is obtained by the addition of ammonium nitrate to the nitration mixture of hexamethylene tetramine and nitric acid, followed by warming. The formaldehyde as a by-product forms more hexamethylenetetramine with the added ammonium nitrate and is converted by the nitric acid into Cyclonite. 

Composition A mixture of caustic soda, phenol, glycerine, and urotropine (hexamet.hylene tetramine) in water solution. 

One other application of modified wood solutions is the formation of filaments or fibers [20]. After making a phenol solution of acetylated wood, hexamethylene tetramine was added and the mixture was heated at 120°C to promote the addition-condensation reaction for a resinified solution with high spinnability. From this solution, filaments were spun and hardened in an oven at a certain heating rate. The maximum temperature for hardening was 250°C, and continuous filaments could easily be obtained by this method. 

Another mixture contains hexamethylene tetramine (CH2)6N4 25, Na202 50 and paraffin (or cylinder oil) 25... 

With alcoholic ammonia, a mixture of mono-, di- and tri-benzylamines is formed. With hexamethylene tetramine an addition product results. ... 

It has a melting point of 169.5°C and boils at 210°C with evolution of nitrous oxide. It forms chloramines on chlorination and is incompatible with acetic acid acetic anhydride, hexamethylene tetramine acetate, and nitric acid mixture ammonia aluminum, calcium nitrate, and formamide mixture metals alkali metals and combustible agents. 

Cyclization, rather than dimerization, can be achieved by this process in the case of dienetetramines. Thus oxidation of N,N,N, N, N",N",N ,N -octamethyl-l,4-penta-diene-l,l,5,5-tetramine (3) affords in high yield a mixture of cis- and frans-cyclo-propylenebis(dimethylaminomethylium) nitrate (4). 

In attempting to increase the yields of formaldehyde by stabilizing it as hexamethylene-tetramine through interaction with ammonia added to the reaction mixture, these workers found that the effect on formaldehyde yield was insignificant. The yield of formic acid, however, was increased to an amount equal to that of the formaldehyde. The lack of methanol production in these experiments is attributed to the greater ease with which methanol is oxidized compared with methane. Methanol is probably formed as a first step and has but a momentary existence under the experimental conditions. 

To overcome the objectionable reoxidation of formaldehyde and decomposition at the temperature of the reaction zone in the oxidation of methane, it has been proposed to react the formaldehyde as fast as formed with some substance to give a compound more stable under the conditions of the reaction and thus to increase the yields obtainable. It is claimed 101 that a reaction between the newly formed formaldehyde and annnonia to form a more stable compound, hexamethylene-tetramine, is possible under certain conditions, so that the formaldehyde is saved from destruction and can be obtained in a technically satisfactory yield. The hexamethylenetetramine is prepared by oxidizing methane with air in the presence of ammonia gas. A mixture consisting of six volumes of methane, twelve volumes of oxygen, and four volumes of ammonia gas is passed through a constricted metal tube which is heated at the constriction. The tube is made of such a metal as copper, silver, nickel, steel, iron, or alloys of iron with tin, zinc, aluminum, or silicon or of iron coated with one of these metals. Contact material to act as a catalyst when non-catalytic tubes are used in the form of wire or sheets of silver, copper, tin, or alloys may be introduced in the tube. At atmospheric pressure a tube temperature... 

Another approach, involving polyamine complexes of transition metal salts, has been studied with specific triamine (IS) and tetramine (12) mixtures. Here again, however, because of protic solvents, the results have been less than adequate to meet the difficult separation problem. 

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