IP Library Granted Patent US 8,461,375
Granted Patent B2
US 8,461,375 · App. 10/541,307 · Granted Jun 11, 2013

Method for the continuous production of alkyl(meth)acrylates with multiple catalyst recycling

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Quick Facts
Patent No.
US 8,461,375
App. No.
10/541,307
Granted
Jun 11, 2013
Kind
B2
Abstract

The invention relates to an improved method for the continuous production of alkyl(methyl)acrylates by transesterification of methyl(meth)acrylate with alcohols that are heavy in comparison with methanol. A special processing technique makes it possible to obtain new levels of product quality. Very high space-time-overall yields can also be obtained. The invention is characterized by the multiple use of a homogeneous catalyst which thereby reduces the costs of auxiliary agents significantly.

Claims (40)

1. A process for continuously preparing higher (meth)acrylic esters (C) in a plant comprising a reaction apparatus and a vacuum evaporation stage for receiving a bottom product remaining after separation of a highly pure ester product, the process comprising:

transesterifying methyl(meth)acrylate (A) with a higher alcohol (B) in the presence of a catalyst or catalyst mixture in the reaction apparatus;

dividing a bottom effluent from the vacuum evaporation stage into a first portion and a second portion; and

recycling the first portion to the reaction apparatus;

wherein dividing the bottom effluent from the vacuum evaporation stage comprises selecting a proportion of the bottom effluent that will constitute the first portion based on current catalyst activity.

2. A process for continuously preparing higher (meth)acrylic esters (C) in a plant comprising a reaction apparatus and a film evaporator for separating a highly pure ester product, the process comprising:

transesterifying methyl(meth)acrylate (A) with a higher alcohol (B) in the presence of a catalyst or catalyst mixture in the reaction apparatus;

dividing a bottom effluent from the film evaporator into a first portion and a second portion; and

recycling the first portion to the reaction apparatus;

wherein dividing the bottom effluent from the film evaporator comprises selecting a proportion of the bottom effluent that will constitute the first portion based on current catalyst activity.

3. A process for continuously preparing higher (meth)acrylic esters (C) in a plant comprising a reaction apparatus, a film evaporator for separating a highly pure ester product, and a vacuum evaporation stage for receiving a bottom product remaining after separation of a highly pure ester product, the process comprising:

transesterifying methyl(meth)acrylate (A) with a higher alcohol (B) in the presence of a catalyst or catalyst mixture in the reaction apparatus;

dividing a bottom effluent from the film evaporator into a first portion and a second portion;

recycling the first portion to the reaction apparatus;

dividing a bottom effluent of the vacuum evaporation stage into a third portion and a fourth portion; and

recycling the third portion to the reaction apparatus;

wherein:

dividing the bottom effluent from the film evaporator comprises selecting a proportion of the bottom effluent from the film evaporator that will constitute the first portion based on current catalyst activity; and

dividing the bottom effluent from the vacuum evaporation stage comprises selecting a proportion of the bottom effluent from the vacuum evaporation stage that will constitute the third portion based on current catalyst activity.

4. The process of claim 1 , wherein the higher alcohol comprises at least one member selected from the group consisting of n-butanol, isobutanol, and 2-ethylhexanol.

5. The process of claim 1 , wherein the catalyst used comprises a homogeneous catalyst.

6. The process according to claim 5 , wherein the catalyst comprises a titanate of the higher alcohol (B).

7. The process according to claim 1 , wherein the first portion comprises 1-95% by weight of the bottom effluent from the vacuum evaporation stage.

8. The process according to claim 7 , wherein the first portion comprises 40-90% by weight of the bottom effluent from the vacuum evaporation stage.

9. The process according to claim 8 , wherein the first portion comprises 60-85% by weight of the bottom effluent from the vacuum evaporation stage.

10. The process according to claim 2 , wherein the first portion comprises 1-95% by weight of the bottom effluent from the film evaporator.

11. The process according to claim 10 , wherein the first portion comprises 40-90% by weight of the bottom effluent from the film evaporator.

12. The process according to claim 11 , wherein the first portion comprises 60-85% by weight of the bottom effluent from the film evaporator.

13. The process according to claim 3 , wherein the first portion and the third portion together comprise 1-95% by weight of the bottom effluents from the film evaporator and the vacuum evaporation stage.

14. The process according to claim 13 , wherein the first portion and the third portion together comprise 40-90% by weight of the bottom effluents from the film evaporator and the vacuum evaporation stage.

15. The process according to claim 14 , wherein the first portion and the second portion together comprises 60-85% by weight of the bottom effluents from the film evaporator and the vacuum evaporation stage.

16. The process of claim 2 , wherein the higher alcohol comprises at least one member selected from the group consisting of n-butanol, isobutanol, and 2-ethylhexanol.

17. The process of claim 3 , wherein the higher alcohol comprises at least one member selected from the group consisting of n-butanol, isobutanol, and 2-ethylhexanol.

18. The process of claim 2 , wherein the catalyst comprises a homogeneous catalyst.

19. The process of claim 3 , wherein the catalyst comprises a homogeneous catalyst.

20. A process for continuously preparing higher (meth)acrylic esters (C) in a plant comprising a reaction apparatus and a vacuum evaporation stage for receiving a bottom product remaining after separation of a highly pure ester product, the process comprising:

transesterifying methyl(meth)acrylate (A) with a higher alcohol (B) in the presence of a catalyst or catalyst mixture in the reaction apparatus;

dividing a bottom effluent from the vacuum evaporation stage into a first portion and a second portion; and

recycling the first portion to the reaction apparatus;

wherein the first portion is recycled directly to the reaction apparatus.

Assignments (7)
CHANGE OF NAME Recorded Mar 20, 2020
From: EVONIK RÖHM GMBH
To: RÖHM GMBH
Reel/Frame 052194/0462 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2020
From: RÖHM GMBH
To: EVONIK OIL ADDITIVES GMBH
Reel/Frame 052194/0550 →
MERGER Recorded Mar 20, 2020
From: EVONIK OIL ADDITIVES GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 052195/0001 →
CHANGE OF NAME Recorded Mar 20, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 052195/0226 →
CHANGE OF ENTITY Recorded Feb 25, 2010
From: ROHM GMBH & CO. KG
To: ROHM GMBH
Reel/Frame 023998/0760 →
CHANGE OF NAME Recorded Feb 25, 2010
From: ROHM GMBH
To: EVONIK ROHM GMBH
Reel/Frame 023998/0789 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 10, 2006
From: ACKERMANN, JOCHEN; HILTNER, HORST; SIEGERT, HERMANN
To: ROEHM GMBH & CO. KG
Reel/Frame 017768/0660 →