Method for the continuous separation by distillation of mixtures that contain morpholine (MO), monoaminodiglycol (ADG), ammonia, water and methoxyethanol (MOE)

Patent metadata

Field	Value
Publication number	US-11518749-B2
Application number	US-201916971650-A
Country	US
Kind code	B2
Filing date	Feb 11, 2019
Priority date	Feb 22, 2018
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

A process for the continuous distillative separation of mixtures comprising morpholine (MO), monoaminodiglycol (ADG), ammonia, water and methoxyethanol (MOE), obtained by reacting diethylene glycol (DEG) with ammonia, wherein ammonia, water, ADG and DEG are removed by distillation and the resulting stream comprising MO and MOE is supplied to a distillation column K40 in which at a top pressure of from 20 to 2000 mbar MO, MOE and organic products having a boiling point 128° C. (1.013 bar) are removed via the bottom and organic products having a boiling point 128° C. are removed overhead, and also MO is removed via a side draw, where K40 is equipped with an evaporator for heating the bottoms, into which is fed heating vapor having a pressure of from 1 to 10 bar.

First claim

The invention claimed is:

1. A process for the continuous distillative separation of mixtures comprising morpholine (MO), monoaminodiglycol (ADG), ammonia, water and methoxyethanol (MOE), obtained by reacting diethylene glycol (DEG) with ammonia, wherein ammonia, water, ADG and DEG are removed by distillation and the resulting stream comprising MO and MOE is supplied to a distillation column K 40 in which at a top pressure of from 20 to 2000 mbar MO, MOE and organic products having a boiling point ≥128° C. (1.013 bar) are removed via the bottom and organic products having a boiling point ≥128° C. are removed overhead, and also MO is removed via a side draw, where K 40 is equipped with an evaporator for heating the bottoms, into which is fed heating vapor having a pressure of from 1 to 10 bar.

2. The process according to claim 1 , wherein, for the distillative removal of ammonia, water, ADG and DEG, a stream comprising ammonia, water, ADG, and DEG is fed to a first distillation column K 10 , ammonia is removed overhead in a first distillation column K 10 , the bottoms output from K 10 is supplied to a second distillation column K 20 , in which water and organic products are removed overhead at a top temperature of from 45 to 198° C. and a top pressure of from 0.1 to 15 bar, the bottoms output from K 20 is supplied to a third distillation column K 30 , in which MO, MOE and organic products having a boiling point <140° C. (1.013 bar) (stream comprising MO and MOE) are removed overhead or via a side draw and ADG, DEG and organic products having a boiling point of >190° C. (1.013 bar) are removed via the bottom.

3. The process according to claim 1 , wherein the reaction of diethylene glycol (DEG) with ammonia is effected in the presence of hydrogen and a heterogeneous hydrogenation catalyst, wherein
the reaction has a conversion based on DEG of 40% to 75% by weight,
the reaction is effected at a pressure of from 100 to 300 bar and a temperature of from 170° C. to 220° C.,
the molar ratio of ammonia to DEG is 4 to 10, and
a catalyst hourly space velocity in the range from 0.05 to 5 kg of diethylene glycol (DEG) per liter of catalyst (bed volume) and per hour.

4. The process according to claim 2 , wherein the stream comprising water and organic products which is removed overhead at column K 20 is partially recycled into a feed or bottom of column K 10 .

5. The process according to claim 2 , wherein the water and organic products removed overhead at column K 20 are supplied to a distillation column K 50 in which aqueous N-ethylmorpholine solution (aqueous EMO solution) is removed overhead or via a liquid side draw and water is removed via the bottom.

6. The process according to claim 2 , wherein the ADG, DEG and organic products having a boiling point of >190° C. (1.013 bar) removed via the bottom of K 30 are supplied to a distillation column K 60 in which an ADG-comprising stream is removed in the side draw, organic products having a boiling point ≤224.8° C. (1.013 bar) are removed overhead and organic products having a boiling point ≥255° C. (1.013 bar) are removed via the bottom.

7. The process according to claim 6 , wherein the ADG-comprising stream which is removed in the side draw at K 60 is supplied to a distillation column K 70 in which ADG is removed via a side draw, organic products having a boiling point ≥224.8° C. (1.013 bar) are removed via the bottom and organic products having a boiling point ≤224.8 (1.013 bar) are removed overhead.

8. The process according to claim 6 , wherein column K 60 is a dividing wall column (DWC).

9. The process according to claim 6 , wherein the ADG-comprising stream which is removed at column K 60 is supplied wholly or partially to a column K 80 in which ADG and organic products having a boiling point ≥224.8° C. (1.013 bar) are removed via the bottom and organic products having a boiling point ≤ 224 . 8 (1.013 bar) are removed overhead.

10. The process according to claim 6 , wherein the organic products having a boiling point ≥255° C. (1.013 bar) removed via the bottom at column K 60 are supplied to an evaporator V 2 in which morpholine aminodiglycol, morpholine diglycol and DEG are removed in gaseous form.

11. The process according to claim 1 , wherein the reaction of DEG with ammonia is effected in a reactor C 1 , wherein DEG and ammonia are heated prior to entry into C 1 by means of a heat exchanger W 2 into which is fed heating vapor having a pressure of from 2 to 50 bar.

12. The process according to claim 7 , wherein columns K 10 , K 20 , K 30 , K 60 and K 70 are each equipped with an evaporator for heating the bottoms, into which is fed heating vapor having a pressure of from 2 to 50 bar.

13. The process according to claim 1 , wherein heating vapor for the column K 40 is obtained by means of flash evaporation of a condensate resulting from the condensation of heating vapor in a heat exchanger, wherein the heating vapor prior to its condensation in the heat exchanger has a pressure of from 2 to 50 bar.

14. The process according to claim 2 , wherein the reaction of DEG with ammonia is effected in a reactor C 1 , wherein DEG and ammonia are heated prior to entry into C 1 by means of a heat exchanger into which is fed heating vapor having a pressure of from 2 to 50 bar.

15. The process according to claim 14 , wherein the heat exchanger is a heat exchanger W 2 or an evaporator of the columns K 10 , K 20 , or K 30 .

16. The process according to claim 2 , wherein the stream comprising ammonia, water, ADG, and DEG fed to the first distillation column K 10 , prior to being supplied to column K 10 , is supplied to an evaporator V 1 in which a portion of the ammonia is removed in gaseous form.

17. The process according to claim 16 , wherein heating vapor having a pressure of from 1 to 10 bar is fed into the evaporator V 1 .

18. The process according to claim 17 , wherein heating vapor for the evaporator V 1 is obtained by means of flash evaporation of a condensate resulting from the condensation of heating vapor in a heat exchanger, wherein the heating vapor prior to its condensation in the heat exchanger has a pressure of from 2 to 50 bar.

19. The process according to claim 7 , wherein the reaction of DEG with ammonia is effected in a reactor C 1 , wherein DEG and ammonia are heated prior to entry into C 1 by means of a heat exchanger into which is fed heating vapor having a pressure of from 2 to 50 bar.

20. The process according to claim 19 , wherein the heat exchanger is a heat exchanger W 2 or an evaporator of one of the columns K 10 , K 20 , K 30 , K 60 or K 70 .

Assignees

• Basf Se

Inventors

• Bussmann Oliver
• Koch Eva
• Heilig Manfred
• Pfeffinger Joachim
• Pastre Joerg
• Melder Johann-Peter

Classifications

• C07C213/02

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07D295/023 Primary

  Preparation; Separation; Stabilisation; Use of additives · CPC title

• C07C41/42

  by distillation · CPC title

• C07C213/10

  Separation; Purification; Stabilisation; Use of additives · CPC title