Manufacture of carboxylic acid amides

• US 4,176,137 A
• Filed: 11/13/1978
• Issued: 11/27/1979
• Est. Priority Date: 11/17/1977
• Status: Expired due to Term

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Krug, Herbert, Dockner, Toni, Platz, Rolf, Heners, Jurgen
• Primary Examiner(s): Demers, Arthur P.
• Application Number:
  US05/959,733
• Time in Patent Office: 379 Days
• Field of Search: 260/561 N, 260/557 R, 260/558 R, 260/561 R, 252/457
• US Class Current: 502/234
• CPC Class Codes: C07C 231/065 By hydration using metals or metallic ions as catalyst
• CPC Class Codes: C07C 233/09 with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton

Abstract

A process for the manufacture of carboxylic acid amides by addition reaction of water with nitriles in the presence of a catalyst which contains copper and magnesium silicate and has been treated with a reducing gas, to which catalyst cement of a certain particle size has been admixed. The amides obtainable by the process are starting materials for the manufacture of solvents, flocculants, wetting agents, pesticides, crop protection agents, textile assistants, e.g. brighteners, water repellent agents, foam stabilizers and detergents.

Claims

1. A process for the manufacture of carboxylic acid amides by addition reaction of water with nitriles in the presence of a copper-containing catalyst, wherein the reaction is carried out with a catalyst which contains copper and a magnesium silicate produced in the presence of a copper compound by precipitation of a magnesium compound with an alkali metal silicate, the catalyst being treated with a reducing gas at an elevated temperature, and wherein the magnesium silicate prepared as described above and separated from the precipitation medium is mixed with from 3 to 50 percent by weight, based on magnesium silicate, of a cement having a particle size of from 1 to 100 micrometers.

2. A process as claimed in claim 1, wherein the reaction is carried out with a starting material of the formula

3. A process as claimed in claim 1, wherein the reaction with water is carried out using a ratio of from 1 to 50 moles of water per nitrile group of one mole of the starting material.

4. A process as claimed in claim 1, wherein the reaction is carried out at from 50°

to 150°

C.

5. A process as claimed in claim 1, wherein the reaction is carried out at from 60°

to 110°

C.

6. A process as claimed in claim 1, wherein the reaction is carried out with from 50 to 100% by weight of total copper, based on the amount by weight of magnesium silicate contained in the catalyst.

7. A process as claimed in claim 1, wherein the reaction is carried out with from 0.5 to 2 moles of nitrile starting material per gram atom of magnesium contained in the catalyst.

8. A process as claimed in claim 1, wherein the reaction is carried out with from 1 to 30% by weight, based on the amount by weight of magnesium contained in the catalyst, of additional metal in the catalyst.

9. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst which has been manufactured by mixing aqueous solutions, of from 10 to 50 percent strength by weight, of copper compounds, magnesium compounds and additional metal compounds, if any, and aqueous solutions, of from 10 to 30 percent strength by weight, of an alkali metal silicate at the above precipitation temperature, effecting the precipitation for from 1 to 60 minutes, and then filtering off the precipitate, washing it with water, pre-drying it at from 20°

to 30°

C., molding it, and then drying it at from 50°

to 70°

C.

10. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst which after its preparation and drying is first kept under nitrogen at from 100°

to 180°

C. and is then treated with reducing gases from 100°

to 230°

C.

11. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst which has been reduced with from 5 to 15 moles of hydrogen or a corresponding equivalent of another reducing gas per kilogram of catalyst.

12. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst which contains from 0 to 1 percent by weight of copper in the form of copper oxide, from 0 to 49 percent by weight of copper in the form of copper silicate and from 51 to 100 percent by weight of copper in the form of non-ionized copper, the said percentages being based on total copper.

13. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst obtained using a magnesium silicate which before mixing with the cement has a specific surface area of from 100 to 200 m² /g, a pore volume of from 0.3 to 1.0 cm³ /g and an average pore radius of from 200 to 800 nanometers.

14. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst obtained using a cement which before mixing with the magnesium silicate has a specific surface area of from 0.5 to 5 m² /g, a tap density of from 800 to 900 g/l and a particle size of from 2 to 70 micrometers.

15. A process as claimed in claim 1, wherein the reaction is carried out with a finished molded catalyst which after reduction has a specific surface area of from 80 to 180 m² /g, a pore volume of from 0.19 to 0.3 cm³ /g and a particle size of from 100 to 400 micrometers.

16. A process as claimed in claim 1, wherein the reaction is carried out with a catalyst obtained using a cement in an amount of from 3 to 50 percent by weight, based on magnesium silicate.