Method for producing C4-C15 lactams

Patent metadata

Field	Value
Publication number	US-10618873-B2
Application number	US-201716073941-A
Country	US
Kind code	B2
Filing date	Jan 30, 2017
Priority date	Feb 1, 2016
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

Abstract

The present invention relates to a process for preparing C4-C15 lactams, in which a C1-C10-alkyl nitrite is reacted with a C4-C15-cycloalkane and is illuminated with a light-emitting diode during the reaction. This forms a C4-C15-cyclohexanone oxime which is then converted further to a C4-C15 lactam; the C1-C10 alcohol formed is recycled into the preparation of the C1-C10-alkyl nitrite.

First claim

The invention claimed is:

1. A process for preparing C 4 -C 15 lactams, comprising the steps of:
a) converting a first mixture (M1) comprising a C 1 -C 10 alcohol, nitrogen oxides and oxygen to obtain a C 1 -C 10 -alkyl nitrite,
b) converting a second mixture (M2) comprising the C 1 -C 10 -alkyl nitrite obtained in step a) and a C 4 -C 15 -cycloalkane to obtain a first product mixture (P1) comprising a C 4 -C 15 -nitrosocycloalkane, a dimeric C 4 -C 15 -nitrosocycloalkane, a C 4 -C 15 -cycloalkanone oxime and a C 1 -C 10 alcohol,
wherein the second mixture (M2) is illuminated during the conversion with a light-emitting diode that emits light having a wavelength in the range from 300 to 500 nm,

c) preparing the C 4 -C 15 lactam by conversion of the C 4 -C 15 -cycloalkanone oxime obtained in step b) in the presence of a catalyst by one of the following steps:
c1) separating the C 1 -C 10 alcohol from the first product mixture (P1) obtained in step b) to obtain a second product mixture (P2) comprising the C 4 -C 15 -cycloalkanone oxime,
recycling the C 1 -C 10 alcohol removed into the first mixture (M1) in step a) and
converting the C 4 -C 15 -cycloalkanone oxime present in the second product mixture (P2) in the presence of the catalyst to obtain the C 4 -C 15 lactam,

or
c2) converting the C 1 -C 15 -cycloalkanone oxime present in the first product mixture (P1) in the presence of the catalyst to obtain a third product mixture (P3) comprising the C 4 -C 15 lactam and the C 1 -C 10 alcohol,
removing the C 1 -C 10 alcohol present in the third product mixture (P3) to obtain the C 4 -C 15 lactam and
recycling the C 1 -C 10 alcohol removed into the first mixture (M1) in step a).

2. The process according to claim 1 , wherein the light-emitting diode in step b) emits light having a wavelength in the range from 340 to 390 nm.

3. The process according to claim 1 , wherein the conversion of the first mixture (M1) in step a) is conducted at a temperature in the range from 10 to 300° C.

4. The process according to claim 1 , wherein the conversion of the first mixture (M1) in step a) is conducted at a pressure in the range from 1 to 50 bar.

5. The process according to claim 1 , wherein the conversion of the second mixture (M2) in step b) is conducted at a temperature in the range from −30 to 150° C.

6. The process according to claim 1 , wherein the conversion of the second mixture (M2) in step b) is conducted at a pressure in the range from 1 to 10 bar.

7. The process according to claim 1 , wherein the catalyst in step c) is selected from the group consisting of zeolites and inorganic acids.

8. The process according to claim 1 , wherein the C 4 -C 15 -cycloalkanone oxime is in gaseous form during the conversion of the C 4 -C 15 -cycloalkanone oxime in step c).

9. The process according to claim 1 , wherein the conversion of the C 4 -C 15 -cycloalkanone oxime in step c) is conducted at a temperature in the range from 50 to 500° C.

10. The process according to claim 1 , wherein the conversion of the C 4 -C 15 -cycloalkanone oxime in step c) is conducted at a pressure in the range from 0.05 to 10 bar.

11. The process according to claim 1 , wherein the C 4 -C 15 -cycloalkane in step b) is selected from the group consisting of cyclopentane, cyclohexane and cyclododecane.

12. The process according to claim 1 , wherein the C 1 -C 10 alcohol present in the first mixture (M1) in step a) is selected from the group consisting of methanol, tert-butanol and neopentanol.

Assignees

• Basf Se

Inventors

• Dehn Richard
• Dehestani Ahmad
• Massonne Klemens
• Waglöhner Steffen
• Teles Joaquim Henrique
• Schaub Thomas
• Brüggemann Till Christian
• Tellaeche Herranz Carlos
• Trapp Oliver
• Wysocki Jedrzej

Classifications

• C07D201/10 Primary

  from cycloaliphatic compounds by simultaneous nitrosylation and rearrangement · CPC title

• B01J29/06

  Crystalline aluminosilicate zeolites; Isomorphous compounds thereof · CPC title

• C07D201/02

  Preparation of lactams · CPC title

• C07B43/06

  of amide groups · CPC title

• C07B43/02

  of nitro or nitroso groups · CPC title