IP Library Granted Patent US 8,445,723
Granted Patent B2
US 8,445,723 · App. 12/194,267 · Granted May 21, 2013

Processes for producing N-alkyl (alkyl)acrylamides

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Quick Facts
Patent No.
US 8,445,723
App. No.
12/194,267
Granted
May 21, 2013
Kind
B2
Abstract

Methods of producing the N-alkyl(alkyl)acrylamides. In a general embodiment, the present disclosure provides a method of producing an N-alkyl (alkyl)acrylamide comprising providing an aqueous solution comprising an N-alkyl amine and adding to the aqueous solution a base and an (alkyl)acrylic anhydride to form a precipitated N-alkyl(alkyl)acrylamide.

Claims (14)

1. A method of producing an N-alkyl (alkyl)acrylamide, the method comprising:

providing an aqueous solution comprising isopropylamine; and

adding to the aqueous solution a base and an amount of methacrylic anhydride to form a precipitated N-alkyl (alkyl)acrylamide,

wherein the precipitated N-alkyl (alkyl)acrylamide has the following structure:

wherein R′ is methyl and R is isopropyl,

wherein the methacrylic anhydride and the base are added to the aqueous solution at a temperature of about 20 to about 30° C., and

wherein an approximate equimolar amount of the methacrylic anhydride and the base is added to the aqueous solution.

2. The method of claim 1 further comprising filtering the aqueous solution to remove the precipitated N-alkyl (alkyl)acrylamide from the aqueous solution.

3. The method of claim 1 , wherein the base is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonium hydroxide and combinations thereof.

4. The method of claim 2 further comprising washing the precipitated N-alkyl (alkyl)acrylamide that was filtered to remove any contaminant from the N-alkyl (alkyl)acrylamide.

5. The method of claim 1 wherein the base is aqueous sodium hydroxide.

6. The method of claim 5 wherein the methacrylic anhydride and the aqueous sodium hydroxide are added simultaneously to the aqueous solution of isopropylamine.

7. The method of claim 2 , further comprising drying under vacuum the precipitated and filtered N-alkyl (alkyl)acrylamide.

8. The method of claim 7 , wherein the precipitated, filtered, and dried N-alkyl (alkyl)acrylamide under nuclear magnetic resonance (NMR) analysis reveals a product comprising of 93% N-isopropyl methacrylamide, 4% water, and 3% impurities.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2017
From: NALCO COMPANY
To: ECOLAB USA INC.
Reel/Frame 042147/0420 →
CHANGE OF NAME Recorded Feb 28, 2017
From: NALCO COMPANY
To: NALCO COMPANY LLC
Reel/Frame 041835/0903 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2017
From: NALCO COMPANY LLC; CALGON CORPORATION; CALGON LLC; ONDEO NALCO ENERGY SERVICES, L.P.
To: ECOLAB USA INC.
Reel/Frame 041836/0437 →
RELEASE OF SECURITY INTEREST Recorded Feb 24, 2017
From: BANK OF AMERICA, N.A.
To: NALCO COMPANY
Reel/Frame 041808/0713 →
RELEASE OF SECURITY INTEREST Recorded Jun 18, 2015
From: BANK OF AMERICA, N.A.
To: NALCO COMPANY
Reel/Frame 035976/0609 →
SECURITY AGREEMENT Recorded May 18, 2009
From: NALCO COMPANY; CALGON LLC; NALCO ONE SOURCE LLC; NALCO CROSSBOW WATER LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 022703/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 29, 2008
From: MORRIS, JOHN D.
To: NALCO COMPANY
Reel/Frame 021627/0785 →