SU1249015A1 - Method of producing beta-(hydanto-5-yl)propionic aldehyde - Google Patents

Description

The invention relates to an improved process for the production of (p- (hydanto-5-yl) propionic aldehyde, which is an intermediate product in the synthesis, the essential amino acid -Bb-tryptophan.

The purpose of the invention is to simplify the process technology.

The goal is achieved by using the process of the mass ratio of the nickel-aluminum alloy to, (5-cyan ethyl) -hydantoin 5 equal to 1: 5-10.

Example. Catalyst treatment "

0.5 g of nickel-aluminum (Ni 50%, A1 50%) are placed in a 100 ml round-bottom heat-resistant flask and treated with 10 ml of 15% NaOH solution at 18 ° C for 1.5 h, after which the catalyst is washed from the alkali with distilled water until neutral and left under a layer of water.

Prepare a solution of cyanoethyl hydantoyl (5-CEG) for hydrogenation, as follows. OjIS m (2.6 g) 5-CEG in 115 ml of distilled water is heated until stirred until complete dissolution, then the solution is cooled to room temperature and mixed with 3.5 ml (d 1;, 723) of phosphoric acid,

Hydrogenation of 5-CEG,

A 0.5 L autoclave is charged with a catalyst and a solution of 5-CEG in phosphoric acid. The hydrogenation is carried out at a mass ratio of catalyst: 5-CEG 1: 5j hydrogen pressure of 2 atm, temperature 25 ° C

Mass ratio of catalyst:; 5-CEG, g / g

Ni-Al alloying temperature Alloy C

Ni-Al leaching time. wah

1: 5 1:10 1: 4

1: 5 1: 5 1.-5 1: 5 1: 5

1: 5 1: 5

18 18

18 18

30 20 22 22 20 20 22 23 23 23

1.5 1.5 1.5 1.5 1.5 2.0 1.3 2.5 2.0 2.0 2.0 2.0 2.0 2.0 2.0

490152

constant stirring until the absorption of OjIG mol of hydrogen. Then the mixture is filtered from the catalyst and neutralized to pH 5-555, Yield 70%. h. 138 ° C

Glowing up phgoa.

1.75 g of fe- {ylhydrazine is added to the filtrate, the mixture is cooled for 4-5 hours at 0 ° C. The phgo formed is filtered off, washed with water and dried. Yield 2.9 g (72%). T, pl. 122 ° C.

Found,%: C 56.0; H 6.2; N 21.9.

c, H ,, N, o, -1/2 n; o

5 Calculated,%: C 56.5; H 5.93; N21.9.

The remaining examples are carried out similarly. The obtained data is entered into the table.

20 As can be seen from examples 1-14, the proposed intervals: by mass ratio of the catalyst: 5-CEG

 1: 5-10, the leaching temperature of the NL-AI alloy 18–30 ° C, at the time of extinction 1.5–2 h, the concentration of the alkali solution 15–20%, the hydrogen pressure 2–10 atm (positive, for example, 1.2, 6.9 and 12) provide simplification of the technology, intensification of the 5-CEG hydrogenation process and high yield of the final product. Increasing - the time of hydrogenation is non-technological (example 4), the violation of the interval in the direction of decreasing the leaching temperature or increasing is impractical (example 5), increasing the leaching time is not consistent (example 8), increasing the alkali concentration is not technological

(example 11).

1: 5 1: 5 1.-5 1: 5 1: 5

1: 5 1: 5

30 20 22 22 20 20 22 23 23 23

Concentration of alkaline solution,% 15 1515 1515 15 15 15 20 13 22 15 15 15

Pressure

hydrogen,

atm

The output of aldegvda,% 72 7267 7071 70 60 71 72 58 71 72 55 65

Editor N. Bobkova

Compiled by N. Podhalyuzina

Tehred G. GerberKorrektor M. Samborska

Order 4196/24 Circulation 379Subscription

VNIIPI USSR State Committee

for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5

Production and printing company, Uzhgorod, st. Project, 4

22 22

10 1.5 12

Claims (1)

METHOD FOR PRODUCING- (HYDANTO-5-IL) PROPIONIC ALDEHYDE by catalytic hydrogenation of ^ - (5-cyanoethyl) -hydantoin with hydrogen using a leached nickel-aluminum alloy in an acidic medium at a hydrogen pressure of 2-10 atm, which is due to the fact that, with In order to simplify the process technology, hydrogenation is carried out at a mass ratio of nickel-aluminum alloy and f- (5-cyanoethyl) hydantoin equal to 1: 5-10.