Process for preparing a polyetheramine

Patent metadata

Field	Value
Publication number	US-10414716-B2
Application number	US-201515534856-A
Country	US
Kind code	B2
Filing date	Dec 1, 2015
Priority date	Dec 12, 2014
Publication date	Sep 17, 2019
Grant date	Sep 17, 2019

Abstract

A process for producing a polyetheramine by reacting a polyether alcohol, previously synthesized in the presence of a basic potassium or sodium compound as catalyst, with ammonia in the presence of hydrogen and a catalyst in one reactor or a plurality of reactors, wherein the employed polyether alcohol when previously synthesized in the presence of a basic potassium compound as catalyst has a content of potassium ions of less than 50 wppm and when previously synthesized in the presence of a basic sodium compound as catalyst has a content of sodium ions of less than 50 wppm.

First claim

The invention claimed is:

1. A process for producing a polyetheramine by reacting a polyether alcohol, previously synthesized in the presence of a basic potassium compound as catalyst, with ammonia in the presence of hydrogen and a catalyst in one reactor or a plurality of reactors, wherein the employed polyether alcohol has a content of potassium ions from 1 to 18 wppm.

2. The process according to claim 1 , wherein the employed polyether alcohol has a content of potassium ions of 1 to less than 10 wppm.

3. The process according to claim 1 , wherein the reaction of the polyether alcohol to afford the polyetheramine is carried out in the liquid phase at an absolute pressure in the range of from 50 to 220 bar.

4. The process according to claim 1 , wherein the reaction of the polyether alcohol to afford the polyetheramine is carried out at a temperature in the range of from 150° C. to 240° C.

5. The process according to claim 1 , wherein the reaction of the polyether alcohol to afford the polyetheramine is carried out using ammonia in a molar ratio per mole of alcoholic hydroxyl group in the polyether alcohol in the range of from 1.5 to 500.

6. The process according to claim 1 , wherein in the reaction of the polyether alcohol to afford the polyetheramine the catalyst is arranged in the reactor/in the reactors as a fixed bed.

7. The process according to claim 1 , which is carried out continuously.

8. The process according to claim 1 , wherein the reaction of the polyether alcohol to afford the polyetheramine is carried out in one or more tubular reactor(s) or tube bundle reactor(s).

9. The process according to claim 1 , wherein the reaction is carried out in a fresh gas mode or a cycle gas mode.

10. The process according to claim 9 , wherein the reaction is carried out with a cycle gas flow rate in the range of from 50 to 1000 normal cubic meters of cycle gas/(m 3 cat. ·h) or a fresh gas flow rate in the range of from 1 to 200 normal cubic meters of fresh gas/(m 3 cat. ·h).

11. The process according to claim 1 , wherein the reaction of the polyether alcohol to afford the polyetheramine is carried out at a catalyst space velocity in the range of from 0.01 to 10 kg of polyether alcohol/(l cat. ·h).

12. The process according to claim 1 , wherein the basic potassium compound is potassium hydroxide.

13. The process according to claim 1 , wherein the polyether alcohol to be reacted is a secondary alcohol and the polyetheramine produced is a primary amine.

14. The process according to claim 1 , for producing polyetheramine of the following formula by reaction of polyether alcohol of formula IIa with ammonia:

wherein the polyether alcohol and the polyetheramine are each in the form of a mixture of molecules where n is on average in the range of from 2.3 to 3.0 and the molar mass of the polyetheramine is on average in the range of from 210 to 250 g/mol.

15. The process according to claim 1 for producing polyetheramine of the following formula by reaction of polyether alcohol of formula IIb with ammonia:

wherein the polyether alcohol and the polyetheramine are each in the form of a mixture of molecules where n is on average in the range of from 31.5 to 35.0 and the molar mass of the polyetheramine is on average in the range of from 1900 to 2100 g/mol.

16. The process according to claim 1 , wherein the catalyst for the reaction of the polyether alcohol to afford the polyetheramine comprises copper and/or cobalt and/or nickel.

17. The process according to claim 1 , wherein prior to its reduction with hydrogen, for the reaction of the polyether alcohol to afford the polyetheramine, the catalytically active mass of the catalyst comprises oxygen-containing compounds of aluminum and/or zirconium and/or chromium and oxygen-containing compounds of copper.

18. The process according to claim 1 , wherein prior to its reduction with hydrogen, for the reaction of the polyether alcohol to afford the polyetheramine, the catalytically active mass of the catalyst comprises oxygen-containing compounds of aluminum and/or zirconium and/or chromium and oxygen-containing compounds of copper and nickel.

19. The process according to claim 1 , wherein prior to its reduction with hydrogen, for the reaction of the polyether alcohol to afford the polyetheramine, the catalytically active mass of the catalyst comprises oxygen-containing compounds of aluminum and/or zirconium and oxygen-containing compounds of copper and cobalt and nickel.

20. The process according to claim 1 , wherein prior to its reduction with hydrogen, for the reaction of the polyether alcohol to afford the polyetheramine, the catalytically active mass of the catalyst comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and in the range of from 0.2 to 5.0 wt % of oxygen-containing compounds of tin calculated as SnO.

21. The process according to claim 1 , wherein prior to its reduction with hydrogen, for the reaction of the polyether alcohol to afford the polyetheramine, the catalytically active mass of the catalyst comprises in the range of from
15 to 80 wt % of oxygen-containing compounds of aluminum, calculated as Al 2 O 3 ,
from 1 to 20 wt % of oxygen-containing compounds of copper, calculated as CuO,
from 5 to 35 wt % of oxygen-containing compounds of nickel, calculated as NiO,
from 5 to 35 wt % of oxygen-containing compounds of cobalt, calculated as CoO and
from 0.2 to 5.0 wt % of oxygen-containing compounds of tin, calculated as SnO.

22. The process according to claim 1 , wherein prior to its reduction with hydrogen, for the reaction of the polyether alcohol to afford the polyetheramine, the catalytically active mass of the catalyst comprises in the range of from
20 to 85 wt % of oxygen-containing compounds of zirconium, calculated as ZrO 2 ,
from 1 to 30 wt % of oxygen-containing compounds of copper, calculated as CuO,
from 14 to 70 wt % of oxygen-containing compounds of nickel, calculated as NiO, and
from 0 to 5 wt % of oxygen-containing compounds of molybdenum, calculated as MoO 3 .

23. The process according to claim 1 , wherein for the reaction of the polyether alcohol to afford the polyetheramine the catalyst is a cobalt-containing catalyst comprising manganese and phosphorus.

24. The process according to claim 1 , wherein for the reaction of the polyether alcohol to afford the polyetheramine the catalyst is a cobalt sponge catalyst or a nickel sponge catalyst.

25. The process according to claim 1 , wherein from the reaction product of the reaction, by distillation,
(1) initially any unconverted ammonia is removed overhead,
(ii) water is removed overhead,
(iii) any by-products present and having a lower boiling point than the process product are removed overhead together with any remaining water,
(iv) the process product polyetheramine is removed as bottom product.

26. The process according to claim 1 , wherein the employed polyether alcohol has a content of potassium ions from 1 to 15 wppm.

Assignees

• Basf Se

Inventors

• Wigbers Christof Wilhelm
• Mägerlein Wolfgang
• Krug Thomas
• Melder Johann-Peter

Classifications

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C08G65/2696

  characterised by the process or apparatus used · CPC title

• C08G65/2648

  Alkali metals or compounds thereof · CPC title

• C08G65/2621 Primary

  containing amine groups · CPC title

• B01J21/04

  Alumina · CPC title