DE946984C - Process for the production of N-alkyl-substituted ureas - Google Patents

Description

Process for the production of N-alkyl-substituted ureas It is known To produce mono- and dialkyl ureas by transamidation of urea with amines, furthermore by alkylation of urea with tertiary alcohols, in the latter case If the yields do not go far above 30% of theory. Through direct action from carbon dioxide to amines, through phosgenation of amines, through addition of amines on cyanic acid or its salts, by acylation of amines using carbamic acid chlorides, the action of amines on isocyanates can be converted into more, depending on the reaction or produce N-substituted ureas with a poor yield. The desulfurization from thioureas to N-substituted ureas is only of preparative importance.

It has now been found, surprisingly, that you can then easily Way to get N-alkyl-substituted ureas, if one thinks of long-chain aliphatic Aldehydes or ketones goes out and these amidated in a hydrogenating manner in the presence of urea. One works here in a suitable solvent - with methanol as has proven particularly beneficial - with hydrogen and catalyst and maintains the corresponding N-alkyl-substituted ureas in almost quantitative yield. One chooses hydrogen prints from around 50 to 100 at and temperatures from about 60 to 1500, with predominantly monosubstituted at temperatures from 60 to 100 ° Urea is formed, while at temperatures above 100 to 1500 in the main di-substituted ureas are obtained. So you get z. B. from Stearon Pentatriakontan- (18) -urea and from palmiton at 100 ° the N-hentriakontan- (X6) -urea, while at I40 to I500 the corresponding di-substituted ureas are obtained will.

It is thus possible in a relatively simple manner to convert to N-substituted To get ureas, which are otherwise difficult to access in a technical manner. The products obtained in this way are suitable for use as plasticizers and lubricants for plastic masses and textile auxiliaries.

Examples I. N-Pentatriakontan- (18) -urea 500g stearon, 125 g of urea, 1.5 g of methanol and 15 g of Raney nickel are placed in an autoclave with a stirrer filled in and 80 at hydrogen pressed out. It is heated up to 100 ° and this Maintained temperature for 4 hours. Then the poorly soluble in methanol becomes Urea product isolated with a yield of 525 g (95 ovo of theory). Q: 77 to 780.

2. N-Hentriakontan- (16) -urea 200 g palmiton, 60 g urea, are in 600 ccm of methanol with 10 g of Raney nickel at 100 ° and 100 at hydrogen Hydrogenated for 3 hours The urea derivative, which is sparingly soluble in methanol, is isolated Yield: 205 g (92% of theory).

F: 7I to 720.

3. Urea derivative from Ct4-Cl8 ketone 2p0 g C14-C10 ketone (from first run fatty acids), 70 g of urea are dissolved in 600 cc of methanol with 10 g of Raney nickel at 100 ° and 100 ° hydrogenated at hydrogen for 2 hours. The monourea product is produced with a yield isolated from 200 g (850/0 of theory). F: 830.

4. Octadecyl urea 260 g stearic aldehyde and 65 g urea in 500 cc of methanol are mixed with 10 g of Raney nickel at 100 ° and 80 to 100 atmospheres hydrogen pressure hydrogenated. After filtering off the Raney nickel and boiling the residue with Methanol, 231 g of octadecylurea were obtained (740/0 of theory). F: 98 to 990.

Claims (1)

PATENT CLAIM: Process for the production of N-alkyl-substituted ureas, characterized in that long-chain aliphatic ketones or Aldehydes in the presence of urea and a suitable solvent, expediently methanol, and a catalyst, hydrogen can act namely at about 50 to 100 atmospheres hydrogen pressure and about 60 to 1500. Publications considered: Journ. amer.chem. soc. 45, 1819, last paragraph; Houben-Weyl, Methods of Organic Chemistry, Vol. VIII (I952), pp. I53, paragraph 3.