IP Library Granted Patent US 7,834,196
Granted Patent B2
US 7,834,196 · App. 11/570,179 · Granted Nov 16, 2010

Process for the preparation of N-alkyl-pyrrolidones

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Quick Facts
Patent No.
US 7,834,196
App. No.
11/570,179
Granted
Nov 16, 2010
Kind
B2
Abstract

A process for the production of N-alkylpyrrolidone from γ-butyrolactone and monoalkylamine in the liquid phase comprising the steps of: feeding monoalkylamine and γ-butyrolactone, in the absence of water or in the presence of less than about 1 wt % of water, to a reaction zone to form a reaction mixture; heating the reaction mixture; withdrawing a product stream from the reaction zone and passing the stream to a distillation zone comprising at least one distillation column operated at sub-atmospheric pressure; adding water to the distillation zone; isolating at least one overhead stream from the distillation zone comprising monoalkylamine, water and optionally N-alkyl-pyrrolidone and condensing the overhead stream against cooling water.

Claims (15)

1. A process for the production of N-alkyl-pyrrolidone from γ-butyrolactone and monoalkylamine in the liquid phase comprising the steps of:

feeding monoalkylamine and γ-butyrolactone, in the absence of water or in the presence of less than about 1 wt % of water, to a reaction zone to form a reaction mixture;

heating the reaction mixture;

withdrawing a product stream from the reaction zone and passing the stream to a distillation zone comprising at least one distillation column operated at sub-atmospheric pressure;

adding water to the distillation zone;

isolating at least one overhead stream from the distillation zone comprising monoalkylamine, water and optionally N-alkyl-pyrrolidone and condensing the overhead stream against cooling water.

2. A process according to claim 1 wherein the reaction mixture comprises a molar excess of monoalkylamine to γ-butyrolactone.

3. A process according to claim 2 where the molar excess is at least 1.05:1.

4. A process according to claim 1 wherein the water present in the reaction mixture is less than 0.2 wt %.

5. A process according to claim 1 wherein two or three distillation columns are used.

6. A process according to claim 5 wherein each distillation column is operated at sub-atmospheric pressure.

7. A process according to claim 1 wherein the pressure of the at least one distillation column is from about 0.05 bar absolute to about 0.3 bar absolute.

8. A process according to claim 1 wherein the water added to the distillation zone is added directly to the at least one distillation column operated at sub-atmospheric pressure.

9. A process according to claim 1 wherein the temperature of the cooling water is from about 5° C. to about 35° C.

10. A process according to claim 1 wherein the monoalkylamine is monomethylamine and the product is N-methyl-pyrrolidone.

Assignments (2)
CHANGE OF NAME Recorded Oct 10, 2017
From: DAVY PROCESS TECHNOLOGY LIMITED
To: JOHNSON MATTHEY DAVY TECHNOLOGIES LIMITED
Reel/Frame 044168/0964 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2007
From: HENSMAN, JOHN RICHARD; KHAMBATI, RIYAZ EZZUDDIN
To: DAVY PROCESS TECHNOLOGY LIMITED
Reel/Frame 019468/0025 →