# US 9,039,870 B2 · Method for producing alkaline (meth)acrylamides

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- Number: US 9,039,870 B2
- Document ID: US9039870B2
- Status: Granted
- Kind: B2
- Application number: 12/444,678
- Filed: 2007-10-05
- Published: 2010-02-11
- Granted: 2015-05-26
- Earliest claimed: 2006-10-09
- Assignees: Clariant Finance (BVI) Limited
- Applicants: Matthias Krull; Christoph Kayser; Roman Morschhaeuser; Helmut Ritter; Sarah Schmitz
- Inventors: Matthias Krull; Christoph Kayser; Roman Morschhaeuser; Helmut Ritter; Sarah Schmitz
- Web page: https://patentgrep.com/patent/US9039870B2

## CPC

- C07C 231/02: from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- B01J 19/126: {Microwaves}
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to a method for producing alkaline amides or imides of ethylenically unsaturated C3 to C6 carboxylic acids by reacting amines that contain at least one primary and/or secondary amino group and at least one tertiary amino group with ethylenically unsaturated C3 to C6 carboxlic acids to form an ammonium salt and said ammonium salt is subsequently converted into the alkaline amide or imide by means of microwave radiation, with the proviso that the primary and/or secondary amino group is devoid of alkoxy groups.

## Claims

### Claim 1

A process for preparing a basic amide of an ethylenically unsaturated C3- to C6-carboxylic acid, where the unsaturation is between the alpha and beta carbons of the carboxylic acid, by reacting at least one amine which contains at least one primary and/or secondary amino group and at least one tertiary amino group with at least one ethylenically unsaturated C3- to C6-carboxylic acid to give an ammonium salt, and subsequently converting the ammonium salt to the basic amide or imide under microwave irradiation, with the proviso that the primary and/or secondary amino group does not comprise any alkoxy groups.

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein the at least one amine corresponds to the formula
HNR1-(A)n-Z
wherein
R1 is hydrogen, C1-C12-alkyl, C5-C12-cycloalkyl, C6-C12-aryl, C7-C12 aralkyl or a heteroaromatic group having from 5 to 12 ring members,
A is an alkylene radical having from 1 to 12 carbon atoms, a cycloalkylene radical having from 5 to 12 ring members, an arylene radical having from 6 to 12 ring members or a heteroarylene radical having from 5 to 12 ring members,
n is 0 or 1,
Z is a group of the formula —NR2R3 or a nitrogen-containing cyclic hydrocarbon radical having at least 5 ring members and
R2 and R3 are each independently C1- to C20-hydrocarbon radicals or polyoxyalkylene radicals.

### Claim 3 (depends on 2)

The process as claimed in claim 2, in which R1 is hydrogen or methyl.

### Claim 4 (depends on 2)

The process as claimed in claim 2, wherein A is a linear or branched alkylene radical having from 1 to 12 carbon atoms and n is 1.

### Claim 5 (depends on 2)

The process as claimed in claim 2, wherein R2 and R3 are each independently aliphatic, aromatic and/or araliphatic hydrocarbon radicals having from 1 to 20 carbon atoms.

### Claim 6 (depends on 5)

The process as claimed in claim 5, wherein R2 and R3 are each independently alkyl radicals having from 1 to 14 carbon atoms.

### Claim 7 (depends on 2)

The process as claimed in claim 2, wherein R2 and/or R3 are each independently polyoxyalkylene radicals of the formula
—(B—O)m—R4
wherein
B is a linear or branched C2-C4-alkylene radical,
m is from 1 to 100,
R4 is hydrogen, an alkyl radical having from 1 to 20 carbon atoms, a cycloalkyl radical having from 5 to 12 ring atoms, an aryl radical having from 6 to 12 ring atoms, an aralkyl radical having from 7 to 30 ring atoms, a heteroaryl radical having from 5 to 12 ring atoms or a heteroaralkyl radical having from 6 to 12 carbon atoms.

### Claim 8 (depends on 2)

The process as claimed in claim 2, wherein Z is a nitrogen-containing cyclic hydrocarbon radical whose nitrogen atom is incapable of forming amides.

### Claim 9 (depends on 1)

The process as claimed in claim 1, wherein the at least one amine is selected from the group consisting of N,N-dimethylethylenediamine, N,N-dimethyl-1,3-propanediamine, N,N diethyl-1,3-propanediamine and N,N-dimethyl-2-methyl-1,3-propanediamine.

### Claim 10 (depends on 1)

The process as claimed in claim 1, wherein the at least one ethylenically unsaturated carboxylic acid is selected from the group consisting of acrylic acid, methacrylic acid, crotonic acid, 2,2-dimethylacrylic acid, maleic acid, fumaric acid and itaconic acid.

### Claim 11 (depends on 1)

The process as claimed in claim 1, wherein the microwave irradiation is performed in the presence of a dehydrating catalyst.

### Claim 12 (depends on 1)

The process as claimed in claim 1, wherein the microwave irradiation is performed in the presence of a solvent.

### Claim 13 (depends on 12)

The process as claimed in claim 12, wherein the solvent has a dielectric loss value of below 10.

### Claim 14 (depends on 1)

The process as claimed in claim 1, wherein the microwave irradiation is performed at temperatures below 300° C.

### Claim 15 (depends on 1)

The process as claimed in claim 1, wherein the reaction is performed at a pressure between 0.1 and 200 bar.

### Claim 16 (depends on 1)

The process as claimed in claim 1, wherein the reaction is effected continuously by irradiating with microwaves in a reaction tube through which the ammonium salt flows.

### Claim 17 (depends on 16)

The process as claimed in claim 16, wherein the reaction tube consists of a nonmetallic, microwave-transparent material.

### Claim 18 (depends on 16)

The process as claimed in claim 16, wherein the residence time of the reaction mixture in the reaction tube is less than 30 minutes.

### Claim 19 (depends on 16)

The process as claimed in claim 16, wherein the reaction tube has a ratio of length to diameter of at least 5.