The method of obtaining simple diaminopropionic ether or simple gidroksiaminopirimidinov ether

 

(57) Abstract:

The invention relates to a new method of obtaining simple diaminopropionic ether or simple gidroksiaminopirimidinov ester by the interaction of dipropyleneglycol with ammonia and hydrogen at 150-190oC and at a pressure of 75-250 bar in the presence of Nickel-copper-chromium catalyst containing 35-58 mol.% Nickel, 10 to 30 mol.% copper and 12-55 mol.% chromium. The method allows to obtain products without changing the structure of the parent compounds in the rearrangement.

The invention relates to a method for simple diaminopropionic ether or simple gidroksiaminopirimidinov ether by catalytic amination of dipropyleneglycol.

From U.S. patent 3654370 know getting polyoxyalkylene of polyoxyalkylene by reacting with ammonia and hydrogen in the presence of Nickel catalyst. However, it will be rearranged polyoxyalkylene skeleton (see Japan patent 49-29313 (1974)).

The present invention is to develop a method by which you can obtain a simple diaminodiphenyl ether and simple hydroxyaminobuteroyl ester with high yield without aetsa way to obtain simple diaminopropionic ether or simple gidroksiaminopirimidinov ester by the interaction of dipropyleneglycol with ammonia and hydrogen at elevated temperature and under pressure in the presence of Nickel catalyst, the distinctive feature of which is that the process is carried out at 150-190oC and at a pressure of 75 to 250 bar in the presence of a Nickel catalyst nickelode-chromium catalyst containing 35-58 mol.% Nickel, 10-30 mol. % copper and 12-55 mol.% chrome.

According to the invention interact with the corresponding diamines or amine alcohols can be subjected to, for example, commercially available standard dipropyleneglycol (representing a mixture of 1,1'-oxydi-2-propanol, 2-(2'-hydroxypropoxy)-1-propanol and 2,2'-oxide-1-propanol).

The interaction can be performed in a flow reactor, provided with a layer of catalyst at 150 - 190oC and at a pressure of 70 to 250 bar.

As the catalyst preferably take gidrirovannoe hydrogen mixture of Nickel oxide, copper oxide and chromium oxide containing 35-58 mol.% Nickel, 10 to 30 mol.% copper and 12-55 mol.% chromium. Typically, the catalyst is used as the fixed layer. It exists in the form of particles with a size of about 1 to 10 mm, for example in the form of solid tablets.

Such catalysts are known in General (see, for example, React. Kinet. Catal. Lett., volume 44; 1, 215-222 (1991)).

As raw materials use of clean or p is a mixture of simple diaminopropionic ether and simple gidroksiaminopirimidinov ether, the molar ratio ranging from 1:1.5 to 1:20. In that case, if using the proposed method want to get clean simple diaminopropionic the ether, or as raw materials can use a mixture of dipropyleneglycol and simple gidroksiaminopirimidinov ether.

Obtained according to the invention compounds can be used as intermediates to obtain plastics.

Example 1

Using a flow reactor with a fixed catalyst bed. In the reactor serves 100 ml of catalyst containing 55 mol.% Nickel, 18 mol.% copper and 27 mol.% chromium. The catalyst is subjected to reduction with a mixture of nitrogen and hydrogen.

Then injected into the reactor per hour 100 l of hydrogen measured under normal conditions), 200 ml of liquid ammonia and 13 ml of liquid dipropyleneglycol. The reaction is carried out at 170oC and at a pressure of 200 bar. Exemptions from ammonia, the reaction product contains of 14.3 wt.% simple diaminopropionic ether, 22,1 weight. % simple gidroksiaminopirimidinov ether, a 27.4 wt.% dimethylmorpholine, to 15.4 wt.% water and 20.7 wt.% dipropyleneglycol. Conversion dipropyleneglycol is 76,9% with relative selectivity for simple diaminopropionic ether, the composition is bringing 32,4 mol.%.

In the distillation distillation pure simple diaminodiphenyl ether (boiling point 74-75oWith 13 mbar) and a simple hydroxyaminobuteroyl ester with a purity of above 99 wt.%.

Example 2

Danny example by analogico example 1, and using the same catalyst. To the reactor is introduced into h 100 l of hydrogen measured under normal conditions), 200 ml of liquid ammonia and 13 ml of liquid dipropyleneglycol. The reaction is carried out at 150oC and at a pressure of 200 bar. Free from ammonia, the reaction products include a 0.9 wt.% simple diaminopropionic ether, and 19.8 wt.% simple gidroksiaminopirimidinov ether, 3.3 wt.% dimethylmorpholine, 4 weight. % of water and 72 wt.% dipropyleneglycol. Conversion dipropyleneglycol thus is 25.6 wt.% with relative selectivity for simple diaminopropionic ether component of 3.1 mol.%, and relative selectivity for simple gidroksiaminopirimidinov ether, component 80,5 mol.%.

Example 3

This example is carried out analogously to example 1. In the reactor serves 200 ml of catalyst containing 38 mol.% Nickel, 11 mol.% copper and 51 mol.% chromium. As described in example 1, the catalyst is subjected to the reduction of the s conditions), 400 ml of liquid ammonia and 26 ml of liquid dipropyleneglycol. The reaction is carried out at 175oC and at a pressure of 200 bar. Free from ammonia, the reaction products consist of 10.7 wt.% simple diaminopropionic ether, 26,7% wt. simple gidroksiaminopirimidinov ether, 26,7% wt. dimethylmorpholine, 14.9 weight. % water and 20.9 weight. % dipropyleneglycol. Conversion dipropyleneglycol is of 76.8 wt.% with relative selectivity for simple diaminopropionic ether component of 15.7 mol.%, and relative selectivity for simple gidroksiaminopirimidinov ether, component 39 mol.%.

Example 4

This example is carried out analogously to example 3, and take the same catalyst with the only difference that instead of dipropyleneglycol using a mixture of 53 weight. % dipropyleneglycol and 47 wt.% obtained from the reaction of simple gidroksiaminopirimidinov ether. Free from ammonia, the reaction product contains about 7.6 wt.% simple diaminopropanol ether, 45,9% wt. simple gidroksiaminopirimidinov ether, 10.6 wt.% the research, 5.5 wt.% water and 30.4 wt.% dipropyleneglycol. That is, the conversion dipropyleneglycol is 40,4 weight. % with relative selectivity towards simple diamenter is simple gidroksiaminopirimidinov ester by the interaction of dipropyleneglycol with ammonia and hydrogen at elevated temperature and under pressure in the presence of Nickel catalyst, characterized in that the process is carried out at 150-190oC and at a pressure of 75-250 bar in the presence of a Nickel catalyst, Nickel-copper-chromium catalyst containing 35-58 mol. % Nickel, 10-30 mol. % copper and 12-55 mol. % chromium.

 

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(1′) (1)

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,

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