Method of producing acrylamide with a Raney copper catalyst
AssigneeNalco Chemical Company
InventorsKarl H. Hoffmann, Donald R. Anderson
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Abstract
An improved process for making acrylamide from a composition of acrylonitrile and water utilizing an improved Raney copper catalyst. The catalyst is prepared by contacting particulate copper/aluminum alloy particles with an aqueous solution containing aliphatic hydrocarbon compound having at least two carbon atoms per molecule and further having at least two oxygen containing groups per molecule.
Claims35
In an improved process of the type wherein acrylonitrile is hydrolyzed to acrylamide under aqueous liquid phase conditions in the presence of a Raney copper catalyst, the improvement which comprises using as said Raney copper catalyst one which has been prepared by contacting particles of a metal alloy comprised of copper and aluminum with an aqueous solution which has dissolved therein on a 100 weight percent total by-product free solution basis from greater than 0 to about 25 weight percent alkali metal hydroxide and from about greater than 0 to about 25 weight percent, or the solubility limit thereof in water, whichever is lower, of at least one aliphatic hydroxylated hydrocarbon compound, said aliphatic hydroxylated hydrocarbon compound having at least two carbon atoms per molecule, and at least two groups per molecule each of which is independently selected from the class consisting of hydroxyl, carboxyl, aldehyde, alkali metal carboxylate and esterified carboxylate, at least one of said groups being hydroxyl, said contacting being conducted at a temperature of below about 80.degree.C.
An improved process for making acrylamide from acrylonitrile comprising the steps of:
- A. activating a Raney copper catalyst through contact of aqueous alkali metal hydroxide with a metal alloy in particulate form and comprised of copper and aluminum thereby to remove from such allow particles at least about 25 weight percent of the aluminum initially present therein, at least a portion of such contacting being conducted over a time interval of from 1/2 to 30 hours using an aqueous alkali metal hydroxide solution which additionally has dissolved therein a hydroxylated hydrocarbon compound, said hydroxylated hydrocarbon compound having at least three carbon atoms per molecule, and at least three groups per molecule each of which is independently selected from the class consisting of hydroxyl, carboxyl, aldehyde, alkali metal carboxylate and esterified carboxylate, at least one of said groups being hydroxyl,
- B contacting the so activated Raney copper catalyst with an aqueous composition comprising from about 10 to 75 weight percent acrylonitrile with the remainder up to 100 weight percent thereof being water while maintaining a temperature of from about 60.degree. to 150.degree.C thereby to hydrolyze at least a portion of said acrylonitrile to acrylamide.
In a process for catalytically hydrolyzing acrylonitrile to acrylamide by contacting acrylonitrile in the presence of water with a Raney copper catalyst, the improvement which comprises the steps of:
- A. first contacting an aqueous solution of a hydroxylated hydrocarbon compound with a group of metal alloy particles comprised of copper and aluminum, said hydroxylated hydrocarbon compound having at least three carbon atoms per molecule, and at least three groups per molecule each of which is independently selected from the class consisting of hydroxyl, carboxyl, aldehyde, alkali metal carboxylate and esterified carboxylate, at least one of said groups being hydroxyl,
- 1. said solution containing from about 0.01 to 1 weight percent of said hydroxylated hydrocarbon compound in dissolved form,
- 2. said group having an average particle size diameter in the range from about 0.001 to 0.5 inch,
- 3. said alloy having a copper to aluminum weight ratio of from about 30:70 to 70:30,
- 4. said solution having a temperature in the range from about 0.degree. to 80.degree. C,
- B. secondly contacting the resulting said group of alloy particles with an aqueous caustic solution,
- 1. said aqueous caustic solution containing from greater than 0 to about 5 weight percent dissolved alkali metal hydroxide,
- 2. said contacting being accomplished over a total time interval of from about 1/2 to 30 hours,
- 3. said caustic solution being added gradually to said group over said time interval,
- 4. the contact rate of starting caustic solution being added to said group during such contacting being from about 0.01 to 10 pounds caustic per pound of said starting group of alloy particles per hour,
- 5. the total quantity of caustic so added being in the range of from about 0.5 to 25 pounds of caustic per pound of said starting group of particles,
- 6. said aqueous caustic solution and the resulting aqueous medium produced in such contacting each having a temperature in the range from about 0.degree. to 80.degree. C,
- 7. said group being maintained in said contact with said solution of said hydroxylated hydrocarbon compound during said contacting with said aqueous caustic solution by admixture of such respective solutions,
- C. washing the so-treated group of product particles to separate therefrom remaining unreacted caustic, and
- D. thirdly contacting at a temperature of from about 60.degree. to 150.degree. C the so-washed group of particles with an aqueous composition comprising from about 10 to 75 weight percent acrylonitrile with the remainder to 100 weight percent thereof being water.
Dependencies are inferred from the claim text.