Production of nitrile compounds

• US 8,373,002 B2
• Filed: 01/12/2009
• Issued: 02/12/2013
• Est. Priority Date: 01/18/2008
• Status: Expired due to Fees

• Current Assignee: Centre National De La Recherche Scientifique, Rhodia Operations (Solvac SA)
• Original Assignee: Centre National De La Recherche Scientifique, Rhodia Operations (Solvac SA)
• Inventors: Marion, Philippe, Geantet, Christophe, Hynaux, Amlie, Laurenti, Dorothe
• Primary Examiner(s): POWERS, FIONA
• Application Number:
  US12/812,891
• Publication Number:
  US 20110082310A1
• Time in Patent Office: 1,492 Days
• Field of Search: None
• US Class Current: 558/335
• CPC Class Codes: C01C 3/0212 from hydrocarbons and ammonia in the presence of oxygen, e.g. the Andrussow-process
• CPC Class Codes: C07C 1/323 the hetero-atom being a nitrogen atom
• CPC Class Codes: C07C 253/10 to compounds containing carbon-to-carbon double bonds
• CPC Class Codes: C07C 255/04 containing two cyano groups bound to the carbon skeleton
• CPC Class Codes: C07C 255/07 Mononitriles
• CPC Class Codes: C07C 4/06 Catalytic processes C07C4/025 takes precedence
• CPC Class Codes: C07C 9/04 Methane production by treatment of sewage C02F11/04; natural gas, synthetic natural gas C10L3/06

Abstract

Organic compounds containing at least one site of ethylenic unsaturation are catalytically hydrocyanated and the medium of hydrocyanation is separated into desired linear organic compounds containing at least one nitrile function, e.g., 3-pentenenitrile, and undesired nitrile by-products, e.g., methylglutaronitrile, and the undesired nitrile by-products are hydrodenitrogenated into ammonia and at least one hydrocarbon compound under an absolute hydrogen pressure ranging from 0.1 to 10 MPa at a temperature ranging from 200° to 500° C. and in the presence of a hydrodenitrogenation catalyst.

Claims

1. A process which comprises catalytically hydrocyanating an organic compound containing at least one site of ethylenic unsaturation and separating the medium of hydrocyanation into desired linear organic compounds containing at least one nitrile functional group and undesired nitrile by-products, and further comprising hydrodenitrogenating said undesired nitrile by-products into ammonia and at least one hydrocarbon compound under an absolute hydrogen pressure ranging from 0.1 to 10 MPa at a temperature ranging from 200°

C. to 500°

C. and in the presence of a hydrodenitrogenation catalyst.

2. The process as defined by claim 1, wherein the hydrodenitrogenation catalyst comprises a metallic element selected from the group consisting of platinum, palladium, rhodium, ruthenium and nickel.

3. The process as defined by claim 2, wherein the hydrodenitrogenation catalyst comprises a metallic element supported on a support selected from the group consisting of alumina, silica, aluminosilicates, silica-aluminas, activated carbons, zirconia, titanium oxide and zeolites.

4. The process as defined by claim 3, wherein the hydrodenitrogenation catalyst comprises platinum deposited on a support selected from the group consisting of zirconia, silica, alumina, aluminosilicates and silica aluminas.

5. The process as defined by claim 1, wherein the hydrogen absolute pressure ranges from 0.5 MPa to 3 MPa.

6. The process as defined by claim 1, wherein the temperature ranges from 300°

C. to 400°

C.

7. The process as defined by claim 1, comprising producing adiponitrile by hydrocyanation of butadiene and wherein the desired nitrile compounds comprise adiponitrile, 3-pentenenitrile, 4-pentenenitrile, 2-methyl-3-butenenitrile or mixtures thereof.

8. The process as defined by claim 7, wherein the undesired nitrile by-products comprise methylglutaronitrile, ethylsuccinonitrile, 2-pentenenitrile, 2-methyl-2-butenenitrile or mixtures thereof.

9. The process as defined by claim 1, wherein the hydrocarbon compounds recovered at the end of the hydrodenitrogenation step are treated by steam reforming and methanation to produce at least one lower alkane, after removal of ammonia.

10. The process as defined by claim 9, wherein the steam reforming and methanation is carried out in the presence of a supported nickel-based catalyst at a temperature ranging from 200 to 700°

C. and under a pressure ranging from 5 to 50 bar.

11. The process as defined by claim 9, comprising producing hydrocyanic acid by reaction of ammonia with methane and wherein the ammonia formed in the hydrodenitrogenation step and/or the lower alkane formed in the steam reforming/methanation step are introduced to the step of producing hydrocyanic acid.