Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine.

http://en.wikipedia.org/wiki/Ethylamine

You can get propanoic acid from HOCl + MEK,

Have you ever done this or have a source for you claim? I can see how it would work, but I'd like more information on it, what sort of yields I can expect, etc.

Looks interesting. I assume it also produces formic acid? This also suggests that acetic acid might be able to be produced from acetone? I'm a bit skeptical.

Quote

You can get propanoic acid from HOCl + MEK,

Have you ever done this or have a source for you claim? I can see how it would work, but I'd like more information on it, what sort of yields I can expect, etc.

Looks interesting. I assume it also produces formic acid? This also suggests that acetic acid might be able to be produced from acetone? I'm a bit skeptical.

http://en.wikipedia.org/wiki/Haloform_reaction

Acetone produces trichloroacetic acid, which hydrolyses further to carbonic acid and an extra chloroform, since both methyl groups on the ketone are attacked. I can't say I'm entirely sure that the hypochlorite won't attack the other side of the ketone in MEK; I do know that you'll get some sort of carboxylic acid.

All the non-Wiki refs on the haloform are hard to find because the literature is ancient. Here's a chemistry textbook:

http://bio-che.mc.edu/valente/ch18.pdf

so the haloform reaction with iodine and MEK apparently does produce propanoate. Also, doing the reaction with ethanol, iodine and NaOH apparently makes formate. Whether hypochlorite will give you side reactions, no idea. Bromine might work better, and the resulting bromoform is safer to handle (unless you want chloroform, for e.g. a Reimer-Tiemann).

You can get propanoic acid from HOCl + MEK,

Have you ever done this or have a source for you claim? I can see how it would work, but I'd like more information on it, what sort of yields I can expect, etc.

Looks interesting. I assume it also produces formic acid? This also suggests that acetic acid might be able to be produced from acetone? I'm a bit skeptical.

The Action of Bleaching Powder on Methyl Ethyl Ketone
Charles D. Hurd and Charles L. Thomas
JACS 55, 1646-1649 (1933)

In contrast to the general familiarity of the reaction between acetone and bleaching powder, very little is known of the action of bleaching powder on other ketones. Ethyl methyl ketone was selected to see if the reaction would yield chloroform and calcium propionate or ethylidene chloride and calcium acetate. Only the first of these two possibilities was realized. This provides a convenient source of propionic acid.

The general equation for this type of synthesis is:

2 RCOCH3 + 6 CaOCl2 -> (RCOO)2Ca + 3 CaCl2 + 2 Ca(OH)2 + 2 CHCl3

In this case R represents C2H5-

Experimental Part

Three hundred grams of commercial bleaching powder (24% available chlorine) was made into a paste with 750 mL of water at 15°C. The temperature of the water must be above 10°C, otherwise too viscous a paste results. This mixture was put into a 3-liter flask which was equipped with a dropping funnel, mercury-sealed stirrer and condenser. Then 25 mL of ethyl methyl ketone was gradually introduced with stirring, care being taken to avoid frothing over. The mixture became quite warm and 10 mL of chloroform, a 45% yield, distilled. The refractive index of the distillate was 1.4452 (for chloroform 1.4458; for ethylidene chloride, 1.4165).

The residue in the flask was neutralized with nitric acid. Then more nitric acid was added to liberate the propionic acid, purposely adding less than the calculated amount to avoid subsequent extraction of nitric acid. Even with an excess, however, ether extracts but insignificant quantities of nitric acid from a dilute aqueous solution.

The acidified solution was made up to 2000 mL with water. An aliquot portion of 500 mL of this was extracted four times with ether for the organic acid and the extracts made up to 250 mL Titration of an aliquot portion of 50 mL of this ether solution with 0.2016 N alkali required 27.5 mL This corresponds to a yield of 8.18 g or 40.7% of the calculated amount of propionic acid.