Sulfurized additives with low levels of alkyl phenols

Patent metadata

Field	Value
Publication number	US-11976250-B2
Application number	US-202218145155-A
Country	US
Kind code	B2
Filing date	Dec 22, 2022
Priority date	Jan 26, 2022
Publication date	May 7, 2024
Grant date	May 7, 2024

Abstract

The present disclosure provides a detergent additives and methods for preparing a sulfurized alkyl phenate product to achieve a high sulfurization ratio and low levels of unsulfurized alkyl phenols.

First claim

What is claimed is:

1. A sulfurized metal phenate detergent comprising a compound of Formula I and a compound of Formula II:

wherein
each R 1 , independently, is a C12 to C20 alkyl group;
R 2 is hydrogen, an alkyl group, an alkylamino group, or a hydroxyalkyl group;
x is an integer from 1 to 4;
n is an integer from 1 to 3;
m is an integer of 0 or 1; and
M 2+ is a divalent metal ion.

2. The sulfurized metal phenate detergent of claim 1 , wherein R 2 is methyl.

3. The sulfurized metal phenate detergent of claim 1 , wherein R 2 has a structure of —R 4 N(R 5 )(R 5 ) wherein R 4 is a C1 to C10 hydrocarbyl group and each R 5 is, independently, a C1 to C4 alkyl group.

4. The sulfurized metal phenate detergent of claim 1 , wherein the detergent includes about 0.01 to about 0.5 weight percent of the compound of Formula II.

5. The sulfurized metal phenate detergent of claim 4 , further comprising about 0.5 weight percent or less of an unsulfurized alkyl phenol.

6. The sulfurized metal phenate detergent of claim 1 , wherein the detergent has a TBN of 0 to 300 mg KOH as measured by the method of ASTM D-2896.

7. The sulfurized metal phenate detergent of claim 1 , wherein each of the compound of Formula I, the compound of Formula II, or both has less than about 15 weight percent of R 1 substitution at the ortho position.

8. The sulfurized metal phenate detergent of claim 1 , wherein the detergent includes up to about 100,000 ppm of the metal provided by an alkali or alkaline metal and up to about 65,000 ppm of sulfur.

9. The sulfurized metal phenate detergent of claim 8 , wherein the alkali or alkaline metal is one of lithium, potassium, sodium, magnesium, calcium, barium, aluminum, or combinations thereof.

10. A sulfurized metal phenate detergent comprising a compound of Formula I and a compound of Formula II:

wherein
each R 1 , independently, is an alkyl group, an aryl group, an alkylaryl group, or arylalkyl group;
R 2 is hydrogen, an alkyl group, an alkylamino group, or a hydroxyalkyl group;
x is an integer from 1 to 4;
n is an integer from 1 to 3;
m is an integer of 0 or 1; and
M 2+ is a divalent metal ion, and
wherein the detergent includes about 0.01 to about 0.5 weight percent of the compound of Formula II.

11. The sulfurized metal phenate detergent of claim 10 , wherein R 1 is a C8 to C20 alkyl group.

12. The sulfurized metal phenate detergent of claim 10 , wherein R 2 is methyl.

13. The sulfurized metal phenate detergent of claim 10 , wherein R 2 has a structure of —R 4 N(R 5 )(R 5 ) wherein R 4 is a C1 to C10 hydrocarbyl group and each R 5 is, independently, a C1 to C4 alkyl group.

14. The sulfurized metal phenate detergent of claim 10 , wherein the detergent has a TBN of 0 to 300 mg KOH as measured by the method of ASTM D-2896.

15. The sulfurized metal phenate detergent of claim 10 , wherein each of the compound of Formula I, the compound of Formula II, or both has less than about 15 weight percent of R 1 substitution at the ortho position.

16. A sulfurized metal phenate detergent comprising a compound of Formula I and a compound of Formula II:

wherein
each R 1 , independently, is an alkyl group, an aryl group, an alkylaryl group, or arylalkyl group;
R 2 is hydrogen, an alkyl group, an alkylamino group, or a hydroxyalkyl group;
x is an integer from 1 to 4;
n is an integer from 1 to 3;
m is an integer of 0 or 1; and
M 2+ is a divalent metal ion, and
wherein the detergent includes up to about 100,000 ppm of the metal provided by an alkali or alkaline metal and up to about 65,000 ppm of sulfur.

17. The sulfurized metal phenate detergent of claim 16 , wherein R 1 is a C8 to C20 alkyl group.

18. The sulfurized metal phenate detergent of claim 16 , wherein R 2 is methyl.

19. The sulfurized metal phenate detergent of claim 16 , wherein R 2 has a structure of —R 4 N(R 5 )(R 5 ) wherein R 4 is a C1 to C10 hydrocarbyl group and each R 5 is, independently, a C1 to C4 alkyl group.

20. The sulfurized metal phenate detergent of claim 16 , wherein each of the compound of Formula I, the compound of Formula II, or both has less than about 15 weight percent of R 1 substitution at the ortho position.

Assignees

• Afton Chemical Corp

Inventors

• Kondracki Paul
• Standefer Edward
• Hou Peter

Classifications

• C10N2030/52

  Base number [TBN] · CPC title

• C10N2030/04

  Detergent property or dispersant property · CPC title

• C10N2010/04

  Groups 2 or 12 · CPC title

• C10M2219/089

  Overbased salts · CPC title

• C10M2219/088

  Neutral salts · CPC title