IP Library Granted Patent US 9,512,062
Granted Patent B2
US 9,512,062 · App. 13/119,244 · Granted Dec 6, 2016

Method for producing N-isopropyl(meth)acrylamide

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Quick Facts
Patent No.
US 9,512,062
App. No.
13/119,244
Granted
Dec 6, 2016
Kind
B2
Abstract

A novel process is described which allows N-isopropyl(meth)acrylamide to be obtained in high purity and yield in a simple manner, by reacting methacrylic anhydride with isopropylamine, optionally in a solvent.

Claims (25)

1. A process for preparing an amide of (meth)acrylic anhydride, the process comprising:

metering an amine, which is a primary or a secondary amine, into a mixture consisting of (meth)acrylic anhydride and a polymerization inhibitor at a maximum metering temperature of 35° C. so that the amine reacts with the anhydride in the presence of the polymerization inhibitor at a maximum reaction temperature of 45° C. to yield the amide and a mother liquor comprising (meth)acrylic anhydride; and

removing the amide from the mother liquor.

2. The process according to claim 1 , further comprising

neutralizing the mother liquor after said removing to precipitate out further amide; and

removing the further amide.

3. The process according to claim 1 , further comprising

distilling the mother liquor after said removing to remove (meth)acrylic acid and obtain a distillation residue comprising further amide; and

removing the further amide.

4. The process according to claim 1 , wherein

the amine is a primary amine.

5. The process according to claim 1 , wherein

the amine is a secondary amine.

6. A process for preparing N-isopropylmethacrylamide, the process comprising:

metering isopropylamine into a mixture consisting of methacrylic anhydride and a polymerization inhibitor at a maximum metering temperature of 30° C. so that methacrylic anhydride reacts with isopropylamine to yield N-isopropylmethacrylamide in the presence of the polymerization inhibitor at a maximum reaction temperature of 40° C.; and

isolating N-isopropylmethacrylamide.

7. A method for preparing a polymer or copolymer, the method comprising:

metering an amine, which is a primary or a secondary amine, into a mixture consisting of (meth)acrylic anhydride and a polymerization inhibitor at a maximum metering temperature of 35° C. so that the amine reacts with the anhydride in the presence of the polymerization inhibitor at a maximum reaction temperature of 45° C. to yield an amide and a mother liquor comprising (meth)acrylic anhydride; and

removing the amide from the mother liquor

polymerizing a monomer comprising the amide of (meth)acrylic anhydride to obtain the polymer or copolymer.

8. A process for preparing an amide of an unsaturated carboxylic acid, the process comprising:

metering an amine, which is a primary or a secondary amine, into a mixture consisting of an anhydride of the unsaturated carboxylic acid, and a polymerization inhibitor at a maximum metering temperature of 30° C. so that the anhydride reacts with the amine in the presence of the polymerization inhibitor to form the amide and a mother liquor comprising the unsaturated carboxylic acid; and

removing the amide from the mother liquor.

9. The process according to claim 8 , wherein the anhydride of the unsaturated carboxylic acid is an anhydride of an unsaturated aliphatic carboxylic acid.

10. The process according to claim 9 , wherein the anhydride of the unsaturated aliphatic carboxylic acid is selected from the group consisting of acrylic anhydride, methacrylic anhydride, and itaconic anhydride.

Assignments (5)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2011
From: KNEBEL, JOACHIM; KARNBROCK, WILHELM; KERSCHER, VOLKER
To: EVONIK ROEHM GMBH
Reel/Frame 026002/0385 →