Claims
- 1. A method for the production of .omega.-aminonitriles which comprises contacting at least one lactam with a catalyst comprising Type A molecular sieves, Type X molecular sieves, or mordenites, in the presence of at least one mole of ammonia per mole of lactam converted and under reaction conditions including temperatures and pressures sufficient to effect ammonialytic cleavage of said lactam to said .omega.-aminonitrile, wherein said reaction temperatures in the range of about 250.degree. to 750.degree. C.,
- wherein said lactam is represented by ##STR5## wherein R is hydrogen, alkyl, cycloalkyl, aryl, or combination thereof, having up to about 8 carbon atoms per R group and a maximum of about 10 carbon atoms in all R groups,
- wherein n is an integer of 3 to 19 when said catalyst comprises said Type A molecular sieve or said mordenite,
- and wherein n is an integer of 3 to 9 when said catalyst comprises said Type X molecular sieves.
- 2. A method for the production of .omega.-aminonitriles which comprises contacting at least one lactam with a catalyst consisting essentially of Type X molecular sieves, in the presence of at least one mole of ammonia per mole of lactam converted and under reaction conditions including temperatures and pressures sufficient to effect ammonialytic cleavage of said lactam to said .omega.-aminonitrile, wherein said pressure is in the range of about 0.1 to 1,000 atmospheres, said ammonia is employed in the range of about 1 to 1,000 moles per mole of said lactam, and said reaction time is in the range of about 0.1 second to 10 hours,
- wherein said lactam is 6-aminohexanoic acid lactam, 4-aminobutyric acid lactam, 10-aminodecanoic acid lactam, 10-amino-3-ethyl-5-octyldecanoic acid lactam, 4-amino-2-methylbutyric acid lactam, 10-amino-3-cyclohexyldecanoic acid lactam, 8-amino-4,4-dicyclopentyloctanoic acid lactam, 10-amino-6-phenyldecanoic acid lactam, 10-amino-4-butyl-6-phenyldecanoic acid lactam, 6-amino-3-benzyl-hexanoic acid lactam, 5-amino-4-(3-ethylcyclohexyl)pentanoic acid lactam, 7-amino-5-(3,5-dimethylphenyl)heptanoic acid lactam, 8-amino-3-(4-ethylcyclohexyl)octanoic acid lactam, 8-amino-2,2,4,4,6,6,-hexamethyloctanoic acid lactam, 9-amino-2-ethyl-3-methyl-6-phenylnonanoic acid lactam, or 5-aminopentanoic acid lactam.
- 3. A method for the production of .omega.-aminonitriles which comprises contacting at least one lactam with a catalyst consisting essentially of Type A molecular sieves or mordenites, in the presence of at least one mole of ammonia per mole of lactam converted and under reaction conditions including temperatures and pressures sufficient to effect ammonialytic cleavage of said lactam to said .omega.-aminonitrile, wherein said pressure is in the range of about 0.1 to 1,000 atmospheres, said ammonia is employed in the range of about 1 to 1,000 moles per mole of said lactam, and said reaction time is in the range of about 0.1 second to 10 hours,
- wherein said lactam is 6-aminohexanoic acid lactam, 4-aminobutyric acid lactam, 10-aminodecanoic acid lactam, 10-amino-3-ethyl-5-octyldecanoic acid lactam, 4-amino-2-methylbutyric acid lactam, 10-amino-3-cyclohexyldecanoic acid lactam, 8-amino-4,4-dicyclopentyloctanoic acid lactam, 10-amino-6-phenyl-decanoic acid lactam, 10-amino-4-butyl-6-phenyldecanoic acid lactam, 6-amino-3-benzylhexanoic acid lactam, 5-amino-4-(3-ethylcyclohexyl)pentanoic acid lactam, 7-amino-5-(3,5-dimethylphenyl)heptanoic acid lactam, 8-amino-3-(4-ethylcyclohexyl)octanoic acid lactam, 8-amino-2,2,4,4,6,6,-hexamethyloctanoic acid lactam, 9-amino-2-ethyl-3-methyl-6-phenylnonanoic acid lactam, 5-aminopentanoic acid lactam, 20-aminoeicosanoic acid lactam, 20-amino-2,14,15,18-tetramethyl-3,5,15-triethyleicosanoic acid lactam, 20-amino-4-benzyleicosanoic acid lactam, 12-aminododecanoic acid lactam, or 11-aminoundecanoic acid lactam.
- 4. A method for the production of an .omega.-aminonitrile which comprises contacting at least one lactam with a catalyst selected from the group consisting of Type A molecular sieves, Type X molecular sieves, and mordenites, in the presence of sufficient ammonia and under reaction conditions of temperature, pressure, and time sufficient to effect ammonialytic cleavage of said lactam to said .omega.-aminonitrile,
- wherein said lactam is represented by ##STR6## wherein R is hydrogen, alkyl, cycloalkyl, aryl, or a combination thereof, having up to 8 carbon atoms per R group, and a maximum of 10 carbon atoms in all R groups,
- wherein n is an integer of 3 to 19 when said catalyst is said Type A molecular sieve or said mordenite,
- and wherein n is an integer of 3 to 9 and when said catalyst is said Type X molecular sieve,
- wherein said reaction temperature is in the range of about 250.degree. to 750.degree. C, said pressure is in the range of about 0.01 to 1000 atmospheres, said ammonia is employed in the range of about 1 to 1000 moles of ammonia per mole of said lactam, and said contacting is conducted for a time interval of about 0.01 second to 10 hours, and
- wherein said .omega.-aminonitrile is represented by ##STR7## wherein R is as defined hereinabove.
- 5. The method according to claim 1 wherein said process comprises the steps of:
- (a) converting said lactam to a liquid lactam,
- (b) passing a stream of ammonia gas through said liquid lactam, thereby producing an admixture comprising said ammonia and said lactam, and
- (c) contacting said admixture with said catalyst, thereby convertsaid lactam to said corresponding .omega.-aminonitrile.
- 6. The process of claim 5 wherein said step (a) is a heating step, said step (b) employs said ammonia at about 1 to about 1000 moles of said ammonia per mole of said lactam, and said contacting step (c) is conducted under a pressure of about 0.1 to about 1000 atmospheres, and during a time of about 0.1 second to 10 hours.
- 7. The process of claim 5 wherein said step (a) is a dissolving step employing a diluent and said lactam is substantially dispersed in said diluent such that said admixture further includes said diluent, and wherein said step (b) further employs said ammonia gas at about 1 to about 1000 moles of said ammonia per mole of said lactam; and wherein in said step (c) said contacting is at a temperature of about 250.degree. to about 750.degree. C.
- 8. The process of claim 7 wherein said admixture is vaporized prior to said contacting.
- 9. The process of claim 7 wherein said diluent constitutes about 1 to 90 weight percent of the total of diluent, ammonia, and lactam, and said diluent is essentially nonreactive under the said ammonialytic cleavage conditions.
- 10. The process of claim 9 wherein said diluent is selected from the group consisting of cyclic paraffinic hydrocarbons, aromatic hydrocarbons, cyclic ethers, mixtures thereof, and wherein said diluent contains 5 to 20 carbon atoms per molecule.
- 11. The process according to claim 6 wherein said lactam is caprolactam, and said catalyst is Type A or Type X molecular sieve.
- 12. The process of claim 7 wherein said lactam is dodecano-lactam, and said catalyst is Type A molecular sieve or mordenite.
- 13. The process according to claim 1 wherein said pressure is in the range of about 0.1 to 1,000 atmospheres, said ammonia is employed in a range of about 1 to 1000 moles per mole of said lactam, and wherein said reaction time is in the range of about 0.1 second to 10 hours.
- 14. The process according to claim 13 wherein said reaction temperature is in the range of about 350.degree. to 500.degree. C, and wherein said reaction pressure is substantially atmospheric pressure.
- 15. The process according to claim 4 wherein said lactam is caprolactam, and said catalyst is said Type A or Type X molecular sieve.
- 16. The process according to claim 4 wherein said lactam is dodecanolactam and said catalyst is said Type A molecular sieve or mordenite.
Parent Case Info
This application is a continuation-in-part of Ser. No. 856,807 filed Sept. 10, 1969 now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
2830072 |
Garritsen et al. |
Apr 1958 |
|
3567757 |
Ida et al. |
Mar 1971 |
|
3579558 |
Immel et al. |
May 1971 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
856807 |
Sep 1969 |
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