IP Library › Granted Patent US 12,344,581
Granted Patent B2
US 12,344,581 · App. 18/191,225 · Granted Jul 1, 2025

Antifoulant compositions for high-severity processing of vinylic monomer streams

Inventors: Jonathan Masere (Richmond, TX); Zhenxing Xi (Katy, TX); Pedro Carvalho Campos (Perre, PT); David Dixon (Baton Rouge, LA); Gregory Appel Melancon, Jr. (Baton Rouge, LA); Ramon Colorado, Jr. (Stafford, TX)
Assignee: ECOLAB USA Inc.
C07C7/20C07C51/50C07C67/62C07C211/51C07D221/00C07C11/167C07C11/18C07C13/15C07C15/46C07C57/04C07C69/15
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Quick Facts
Patent No.
US 12,344,581
App. No.
18/191,225
Granted
Jul 1, 2025
Kind
B2
Abstract

Inhibitor compositions for abating undesirable polymerization during processing of hydrocarbon stream laden with reactive vinylic monomers are provided. The polymerization inhibitor compositions include at least a first inhibitor compound having a stable nitroxide radical and a second inhibitor including phenylenediamine. Methods of inhibiting the polymerization of monomers using the compositions of the disclosure are also provided. The methods of inhibiting polymerization of monomers include a step of adding a composition of the disclosure to the monomer. In some instances, the monomer is an ethylenically unsaturated monomer. Such ethylenically unsaturated monomers include, but are not limited to, vinyl acetate, acrylonitrile, acrylates, methacrylates, 1,3-butadiene, styrene, isoprene, (meth)acrylic acid, and combinations thereof. Methods of preparing the polymerization inhibitors and compositions of the disclosure are also provided.

Claims (25)

1. A composition for inhibiting monomer polymerization consisting essentially of:

a first inhibitor compound comprising a stable nitroxide radical; and

a second inhibitor compound comprising a phenylenediamine.

2. The composition of claim 1 , wherein the first inhibitor compound is of formula (I):

wherein R 1 is C 1 -C 22 alkyl or aryl, wherein the alkyl and aryl are optionally substituted with one or more C 1 -C 22 alkyl or aryl.

3. The composition of claim 1 , wherein the first inhibitor is selected from the group consisting of: 1-oxyl-2,2,6,6-tetramethylpiperin-4-ol; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-ethoxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-propoxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-butoxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-pentoxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-hexyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-heptyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-octyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-nonyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-decyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-undecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-dodecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-tridecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-tetradecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-pentadecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-hexadecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-heptadecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-octadecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-nodecyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-decyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-icosyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-henicosyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-docosyloxy-2,2,6,6-tetramethylpiperidin-1-oxy; 4-(phenoxy) 2,2,6,6-tetramethylpiperidin-1-oxy; 4-(benzyloxy)-2,2,6,6-tetramethylpiperidin-1-oxy; 2,2,6,6-tetramethyl-4-(naphthalen-2-yloxy) piperidin-1-oxy; and any combination thereof.

4. The composition of claim 1 , wherein the first inhibitor is a compound of formula III:

wherein R 3 is —O, or —OH; and R 4 is C 1 -C 22 alkyl or aryl, wherein the alkyl and aryl are optionally substituted with one or more C 1 -C 22 alkyl or aryl.

5. The composition of claim 4 , wherein the first inhibitor is selected from the group consisting of: 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl acetate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl propanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl butyrate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl pentanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl hexanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl heptanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl octanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl nonanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl decanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl undecanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl dodecanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl 2-ethylhexanoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl stearate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl benzoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl palmitoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl behenoate; 1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl 4-tert-butylbenzoate; and any combination thereof.

6. The composition of claim 1 , wherein the second inhibitor compound is a phenylenediamine of formula (IV) or formula (V):

wherein X 1 and X 2 are independently C 1 -C 22 alkyl, or aryl, wherein the alkyl and aryl are optionally substituted with one or more C 1 -C 22 alkyl or aryl.

7. The composition of claim 1 , wherein the second inhibitor is selected from the group consisting of: 1,2-phenylenediamine, 1,4-phenylenediamine, N,N′-di-methyl-p-phenylenediamine, N,N′-di-sec-butyl-1,4-phenylenediamine, N,N′-di-1,4-dimethylpentyl-1,4-phenylenediamine, N,N′-di-acetyl-1,4-phenylenediamine, N-tert-butyl-N′-phenyl-1,4-phenylenediamine, N,N′-di-phenyl-1,4-phenylenediamine, and any combination thereof.

8. The composition of claim 1 , wherein the first inhibitor compound is present in the composition at a concentration of about 0.01% by weight to about 80% by weight.

9. The composition of claim 1 , wherein the second inhibitor compound is present in the composition at a concentration of about 0.01% by weight to about 50% by weight.

10. The composition of claim 1 , wherein a mole ratio of the first inhibitor compound to the second inhibitor compound is about 100:1 to about 1:100.

11. The composition of claim 1 , wherein the composition further comprises an organic solvent.

12. The composition of claim 1 , wherein the composition further comprises an ethylenic unsaturated monomer selected from the group consisting of vinyl acetate, acrylonitrile, an acrylate, a methacrylate, 1,3-butadiene, styrene, isoprene, cyclopentadiene, dicyclopentadiene, acrylic acid, methacrylic acid and any combination thereof.

13. A method of inhibiting polymerization of a monomer, the method comprising:

adding the composition of claim 1 to the monomer.

14. The method of claim 13 , wherein the monomer is provided within a solution.

15. The method of claim 14 , wherein the solution further comprises one or more additional components selected from: an acid, an organic solvent, and water.

16. The method of claim 13 , wherein the monomer is an ethylenic unsaturated monomer.

17. The method of claim 13 , wherein the composition is added to the monomer such that a concentration of the first inhibitor compound is about 0.1 ppm to about 10,000 ppm.

18. The method of claim 13 , wherein the composition is added to the monomer such that a concentration of the second inhibitor compound is about 0.1 ppm to about 10,000 ppm.

19. The method of claim 13 , wherein the monomer is selected from the group consisting of vinyl acetate, acrylonitrile, an acrylate, a methacrylate, 1,3-butadiene, styrene, divinyl benzene, isoprene, cyclopentadiene, dicyclopentadiene, acrylic acid, methacrylic acid and any combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2023
From: MASERE, JONATHAN; XI, ZHENXING; CAMPOS, PEDRO CARVALHO; DIXON, DAVID; MELANCON, GREGORY APPEL, JR.; COLORADO, RAMON, JR.
To: ECOLAB USA INC.
Reel/Frame 063512/0872 →
Continuity (2)
Provisional Application 63326373 · Apr 1, 2022
Related Publication 20230312440A1 · Oct 5, 2023
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