IP Library Granted Patent US 11,746,101
Granted Patent B2
US 11,746,101 · App. 17/864,170 · Granted Sep 5, 2023

Chemical products for surface protection

Inventors: Charles Zha (Stafford, TX); Jan Beetge (Stafford, TX)
Assignee: HEXION INC.
C07D403/10C02F5/12C07C233/78C07D207/00C07D233/24C09D5/1625C02F2103/023C02F2103/365C02F2303/20C02F2305/04
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Quick Facts
Patent No.
US 11,746,101
App. No.
17/864,170
Granted
Sep 5, 2023
Kind
B2
Abstract

Some implementations of the present disclosure prevent, reduce or at least slow equipment fouling using passivation as a treatment prior to contacting metallic components with hydrocarbon containing fluid, that is, an environment where fouling occurs. For example, one implementation includes a method of passivating heat exchangers in a SAGD process or system using the compositions and compounds of the present disclosure. The composition may be applied to a component prior to its first inclusion in an online system or following placing the system offline for maintenance. The composition may be used to treat metallic equipment surface(s), for example, via contacting them with a suspension or solution of the composition described herein, prior placing the system online. The method may further include treatment of the process fluid, for example, via injection or batch treatment of the composition with the compositions described herein into the process fluid.

Claims (60)

1. A composition, comprising:

a compound represented by formula (IV):

a salt thereof, an isomer thereof, or combinations thereof, wherein:

R 1 and R 2 are each independently selected from the group consisting of —H, C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, and C 1 -C 24 alkanoalkyl, C 1 -C 36 alkylcarboxy, and C 7 -C 20 arylalkyl;

R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of —H, —OH, C 1 -C 4 alkyl, and C 1 -C 4 alkylcarboxy;

R 7 and R 8 are each independently selected from the group consisting of C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, C 1 -C 24 alkanoalkyl, C 1 -C 36 alkylcarboxy, C 7 -C 20 arylalkyl, —P(OH)O 2 − , and —SO 3 − ;

X and Y are each independently selected from the group consisting of an alkylamino group (—R 11 NH—), an alkylamido group (—R 11 NHC(O)—), an alkylether group (—R 11 O—), methylene group, and an alkylester group (—R 11 C(O)O—); and

R 11 is a C 1 -C 4 alkyl.

2. The composition of claim 1 , wherein R 7 and R 8 are each independently a C 1 -C 36 alkylcarboxy.

3. The composition of claim 1 , wherein R 7 and R 8 are each independently a C 1 -C 4 alkylcarboxy.

4. The composition of claim 1 , wherein:

X and Y are each independently selected from the group consisting of an alkylamino group (—R 11 NH—), an alkylamido group (—R 11 NHC(O)—), an alkylether group (—R 11 O—), methylene group, and an alkylester group (—R 11 C(O)O—);

X and Y are the same; and

each of R 1 and R 2 are the same or different.

5. The composition of claim 1 , wherein the compound represented by formula (IV) is represented by formula (IV-D-1) or formula (IV-D-2):

wherein, for formula (IV-D-1) and formula (IV-D-2):

R 1 and R 2 are each independently selected from the group consisting of —H, C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, C 1 -C 24 alkanoalkyl, —P(OH)O 2 − , —SO 3 − , and C 7 -C 20 arylalkyl;

R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of —H, —OH, C 1 -C 4 alkyl, and C 1 -C 4 alkylcarboxy; and

R 7 and R 8 are each independently selected from the group consisting of C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, C 1 -C 24 alkanoalkyl, —P(OH)O 2 − , —SO 3 − , and C 7 -C 20 arylalkyl.

6. The composition of claim 1 , wherein the compound represented by formula (IV) is represented by formula (IV-E):

wherein, for formula (IV-E):

R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of —H, —OH, C 1 -C 4 alkyl, and C 1 -C 4 alkylcarboxy;

R 7 and R 8 are each independently selected from the group consisting of —CH 2 CH 2 NHR 1 , —CH 2 CH 2 NHR 2 , —CH 2 CH 2 NHC(O)R 1 , —CH 2 CH 2 NHC(O)R 2 , —CH 2 CH 2 OR 1 , —CH 2 CH 2 OR 2 , —CH 2 CH 2 OC(O)R 1 , and —CH 2 CH 2 OC(O)R 2 ; and

R 1 and R 2 are each independently selected from the group consisting of H, C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, and C 1 -C 24 alkanoalkyl.

7. The composition of claim 1 , further comprising an additive selected from the group consisting of surfactants, acids, film forming agents, solvents, freeze point depressors, scale inhibitors, wetting agents, and alkylene oxides.

8. The composition of claim 1 , further comprising a scale inhibitor selected from the group consisting of: phosphate esters, acetylenic alcohols, fatty acids and/or alkyl-substituted carboxylic acids and anhydrides, quaternary amines, sulfur-oxygen phosphates and/or polyphosphate esters, and combinations thereof.

9. The composition of claim 1 , further comprising a surfactant selected from the group consisting of: quaternary alkyl amines, tetrabutylammomium acetate, tetrabutylammonium bromide, tetrabutylammonium nitrate, sodium lauryl sulfate, sodium lauryl ether sulfate, polyamines, polymers or copolymers comprising ethylene oxide, propylene oxide, alkoxylates of alkylphenol or alkylphenol based resins, and combinations thereof.

10. The composition of claim 1 , further comprising a solvent selected from the group consisting of: formamide, propylene carbonate, tetrahydrofuran, alcohols, glycols, methanol, isopropanol, ethanol, acetone, toluene, xylene, monobutyl ether, dimethoxyethane, diglyme, naphtha, dimethyl amine, n-methyl pyrrolidone, biodegradable solvents, or renewable solvents, and mixtures thereof, with or without water.

11. A method of treating fouling of a metallic component, the method comprising:

contacting a metallic component with the composition of claim 1 ; and

contacting the metallic component with a hydrocarbon-containing process fluid stream.

12. The method of claim 11 , wherein contacting the metallic component comprises continuously injecting the composition into the hydrocarbon-containing process fluid stream during operation.

13. The method of claim 12 , wherein between about 1 ppm and about 1000 ppm of the composition is injected into the hydrocarbon-containing process fluid stream.

14. The method of claim 13 , wherein between about 5 ppm and about 750 ppm of the composition is injected into the hydrocarbon-containing process fluid stream.

15. The method of claim 11 , wherein the metallic component is a heat exchanger.

16. The method of claim 11 , wherein the hydrocarbon-containing process fluid stream is a steam assisted oil recovery system.

17. A composition, comprising:

a surfactant;

a corrosion inhibitor;

a solvent; and

a compound represented by formula (IV):

a salt thereof, an isomer thereof, or combinations thereof, wherein:

R 1 and R 2 are each independently selected from the group consisting of —H, C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, and C 1 -C 24 alkanoalkyl, C 1 -C 36 alkylcarboxy, and C 7 -C 20 arylalkyl;

R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of —H, —OH, C 1 -C 4 alkyl, and C 1 -C 4 alkylcarboxy;

R 7 and R 8 are each independently selected from the group consisting of C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, C 1 -C 24 alkanoalkyl, C 1 -C 36 alkylcarboxy, C 7 -C 20 arylalkyl, —P(OH)O 2 − , and —SO 3 − ;

X and Y are each independently selected from the group consisting of an alkylamino group (—R 11 NH—), an alkylamido group (—R 11 NHC(O)—), an alkylether group (—R 11 O—), methylene group, and an alkylester group (—R 11 C(O)O—); and

R 11 is a C 1 -C 4 alkyl.

18. The composition of claim 17 , wherein R 7 and R 8 are each independently a C 1 -C 36 alkylcarboxy.

19. The composition of claim 17 , wherein the compound represented by formula (IV) is represented by formula (IV-B):

wherein, for formula (IV-B):

R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of —H, —OH, C 1 -C 4 alkyl, and C 1 -C 4 alkylcarboxy;

R 7 and R 8 are each independently selected from —CH 2 C(O)O − , —CH 2 CH 2 C(O)O − , —P(OH)O 2 − , —SO 3 − , and C 7 -C 20 arylalkyl;

R 9 and R 10 are each independently selected from the group consisting of

—CH 2 CH 2 NHCH 2 CH(OH)CH 2 OC(O)R 1 ,

—CH 2 CH 2 NHCH 2 CH(OH)CH 2 OC(O)R 2 ,

—CH 2 CH 2 OCH 2 CH(OH)CH 2 OC(O)R 1 ,

—CH 2 CH 2 OCH 2 CH(OH)CH 2 OC(O)R 2 , and

and

R 1 and R 2 are each independently selected from the group consisting of —H, C 1 -C 24 alkyl, C 1 -C 24 aminoalkyl, and C 1 -C 24 alkanoalkyl.

20. The composition of claim 19 , wherein R 7 and R 8 are each independently a C 1 -C 4 alkylcarboxy.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2022
From: ZHA, CHARLES; BEETGE, JAN
To: HEXION INC.
Reel/Frame 060509/0457 →
Continuity (5)
Division 17072682 · Oct 16, 2020
Division 15349650 · Nov 11, 2016
Provisional Application 62260777 · Nov 30, 2015
Provisional Application 62258023 · Nov 20, 2015
Related Publication 20220372307A1 · Nov 24, 2022