Polyalphaolefin phenols with high para-position selectivity

Patent metadata

Field	Value
Publication number	US-11976252-B2
Application number	US-202318171560-A
Country	US
Kind code	B2
Filing date	Feb 20, 2023
Priority date	Feb 21, 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 from polyalphaolefins.

First claim

What is claimed is:

1. A sulfurized alkyl phenate comprising a polyalphaolefin substituted bridged hydroxyaromatic compound or salt thereof, wherein the polyalphaolefin is derived from one or more C6 to C14 monomers forming an oligomer in the form of a dimer, a trimer, a tetramer, a pentamer or combinations thereof, or copolymers of the oligomer, copolymer variants of the oligomer, or combinations thereof; and wherein about 40 mol percent or greater of the polyalphaolefin includes a carbon atom configured to form a tertiary carbocation positioned to react with the hydroxyaromatic compound at the para-position.

2. The sulfurized alkyl phenate of claim 1 , wherein at least one alkyl group adjacent the tertiary carbocation is an alkyl group having 1, 2, or 3 carbon atoms.

3. The sulfurized alkyl phenate of claim 1 , wherein the polyalphaolefin is obtained from one or more C8 to C12 monomers forming the oligomer in the form of the dimer, the trimer, the tetramer, the pentamer, or combinations thereof.

4. The sulfurized alkyl phenate of claim 1 , wherein about 50 mol percent or greater of the polyalphaolefin includes a carbon atom configured to form a tertiary carbocation.

5. The sulfurized alkyl phenate of claim 1 , wherein the polyalphaolefin contains vinylidene olefins, trisubstituted olefins, or mixtures thereof.

6. The sulfurized alkyl phenate of claim 5 , wherein the polyalphaolefin contains greater than about 40 mol percent of the vinylidene olefins, the trisubstituted olefins, or mixtures thereof.

7. The sulfurized alkyl phenate of claim 5 , wherein the polyalphaolefin is a trisubstituted olefin and includes about 40 weight percent or more of the dimer.

8. The sulfurized alkyl phenate of one or claim 7 , wherein the polyalphaolefin includes about 40 weight percent or less of the trimer; and/or about 20 weight percent or less of the tetramer; and/or about 5 weight percent or less of the pentamer.

9. The sulfurized alkyl phenate of claim 1 , wherein the polyalphaolefin contains predominately vinylidene olefins, trisubstituted olefins, or mixtures thereof and includes about 40 weight percent or more of the C3 or shorter alkyl group adjacent the tertiary carbocation.

10. The sulfurized alkyl phenate of claim 1 , wherein the polyalphaolefin includes double bonds having a vinylidene structure and/or a tri-substituted structure.

11. The sulfurized alkyl phenate of claim 1 , wherein the polyalphaolefin includes about 40 mol percent or more of a vinylidene olefin, a tri-substituted olefin, or combinations thereof.

12. A detergent composition including a sulfurized alkyl phenate having a structure of Formula IX:

wherein
each R 24 independently, is a polyalphaolefin derived from one or more C6 to C14 monomers forming an oligomer in the form of a dimer, a trimer, a tetramer, a pentamer, or combinations thereof, or copolymers of the oligomer, copolymer variants of the oligomer, or combinations thereof including a residue of a tertiary carbocation forming the bond to the aromatic ring, wherein at least 50 mol percent of R 24 is bonded to the aromatic ring at the para-position; wherein each R 24 , independently, has about 40 weight percent or more of at least one alkyl group adjacent the tertiary carbocation having 1, 2, or 3 carbon atoms;
x is an integer from 1 to 4; and
M 2+ is a divalent metal ion.

13. The detergent composition of claim 12 , wherein each R 24 , independently, is formed from one or more C8 to C12 monomers forming the oligomer in the form of the dimer, the trimer, the tetramer, the pentamer, or combination thereof.

14. The detergent composition of claim 12 , wherein R 24 is derived from vinylidene olefins, trisubstituted olefins, or mixtures thereof.

15. The detergent composition of claim 14 , wherein the R 24 contains about 40 mol percent or greater of the vinylidene olefins, the trisubstituted olefins, or mixtures thereof.

16. The detergent composition of claim 14 , wherein the R 24 is a trisubstituted olefin and about 40 weight percent or more of R 24 is a dimer.

17. The detergent composition of claim 16 , wherein about 40 weight percent or less of R 24 is a trimer, about 20 weight percent or less of R 24 is a tetramer, and/or about 5 weight percent or less of R 24 is a pentamer.

18. The detergent composition of claim 12 , wherein the R 24 group is derived from a mixture of oligomers and a majority of oligomers in the mixture have the structure of Formula VI and/or Formula VII below:

wherein
R 11 is an alkyl group;
each of R 12 , R 13 , R 14 , R 15 , and/or R 16 , is the same or different at each occurrence, and independently represents a hydrogen or a substituted or unsubstituted hydrocarbyl group;
only one of R 17 , R 18 and R 19 is hydrogen and one of the remaining two of R 17 , R 18 and R 19 is a substituted or unsubstituted hydrocarbyl group having 1, 2, or 3 carbons and the other of the remaining two of R 17 , R 18 and R 19 is a substituted or unsubstituted hydrocarbyl group;
each of R 20 , R 21 , R 22 , and/or R 23 , is the same or different at each occurrence, and independently represents a hydrogen or a substituted or unsubstituted hydrocarbyl group;
each n is, independently, an integer of 0 to 3.

19. A lubricating oil composition including the sulfurized alkyl phenate of claim 1 and one or more base oils of lubricating viscosity.

20. A lubricating oil composition including the detergent composition of claim 12 and one or more base oils of lubricating viscosity.

Assignees

• Afton Chemical Corp

Inventors

• Tian Xin
• Bell Jason
• Anderson Steven

Classifications

• C10N2030/04

  Detergent property or dispersant property · CPC title

• C10N2020/071

  Branched chain compounds · CPC title

• C10N2010/04

  Groups 2 or 12 · CPC title

• C10M2219/089

  Overbased salts · CPC title

• C10M2219/088

  Neutral salts · CPC title