Post-treated sulfurized salt of an alkyl-substituted hydroxyaromatic composition

Patent metadata

Field	Value
Publication number	US-9249091-B2
Application number	US-201213727892-A
Country	US
Kind code	B2
Filing date	Dec 27, 2012
Priority date	Dec 27, 2011
Publication date	Feb 2, 2016
Grant date	Feb 2, 2016

Abstract

Disclosed herein is a post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition which is a reaction product of (a) a salt of a sulfurized alkyl-substituted hydroxyaromatic composition, wherein the alkyl-substituted hydroxyaromatic compound is derived from alkylation of a hydroxyaromatic compound with one or more olefins comprising C 9 to C 18 oligomers of monomers selected from propylene, butylene or mixtures thereof, (b) a source of an aldehyde and (c) a primary and/or secondary monoamine compound having at least one active hydrogen. The post-treated salt of a sulfurized alkylhydroxyaromatic composition disclosed herein has a reduced content of unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt as compared to the content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt present in the non-post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition.

First claim

What is claimed is:

1. A post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition which is a reaction product of (a) a salt of a sulfurized alkyl-substituted hydroxyaromatic composition, wherein the alkyl-substituted hydroxyaromatic compound is derived from alkylation of a hydroxyaromatic compound with one or more olefins comprising C 9 to C 18 oligomers of monomers selected from propylene, butylene or mixtures thereof, (b) a source of an aldehyde and (c) a primary and/or secondary monoamine compound having at least one active hydrogen.

2. The post-treated salt of a sulfurized alkylhydroxyaromatic composition of claim 1 , wherein the salt of a sulfurized alkyl-substituted hydroxyaromatic composition is produced by (i) alkylating a hydroxyaromatic compound with one or more olefins comprising C 9 to C 18 oligomers of monomers selected from propylene, butylene or mixtures thereof; and (ii) sulfurizing and neutralizing the alkyl-substituted hydroxyaromatic compound in any order.

3. The post-treated salt of a sulfurized alkylhydroxyaromatic composition of claim 1 , wherein the salt of a sulfurized alkyl-substituted hydroxyaromatic composition is an overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition.

4. The post-treated salt of a sulfurized alkylhydroxyaromatic composition of claim 1 , wherein the aldehyde is selected from the group consisting of formaldehyde, paraformaldehyde, formal in and mixtures thereof.

5. The post-treated salt of a sulfurized alkylhydroxyaromatic composition of claim 1 , wherein the primary and/or secondary monoamine compound is a primary monoamine compound selected from the group consisting of methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tetradecylamine, hexadodecylamine, stearylamine, octadecylamine, eicosylamine, cyclopentylamine, cyclohexylamine, aniline, benzylamine, 2-aminotoluene, 3-aminotoluene, 4-aminotoluene, methanolamine, ethanolamine, 2,4-dimethylaniline, 2,3-dimethylaniline, 2,5-dimethylaniline, 2,6-dimethylaniline, 3,4-dimethylaniline, 3,5-dimethylaniline, 2,4,5-trimethylaniline, 2,4,6-trimethylaniline, 3,4,5,6-tetramethylaniline, 2,4,5,6-tetramethylaniline, 2,3,5,6-tetramethylaniline, 2-ethyl-3-hexylaniline, 2-ethyl-4-hexylaniline, 2-ethyl-S-hexylaniline, 2-ethyl-6-hexylaniline, 3-ethyl-4-hexylaniline, 3-ethyl-5-hexylaniline, 3-ethyl-2-hexylaniline, 4-ethyl-2-hexylaniline, 5-ethyl-2-hexylaniline, 6-ethyl-2-hexylaniline, 4-ethyl-3-hexylaniline, 5-ethyl-3-hexylaniline, 3,4,6-triethyltoluene, 2-methoxyaniline, 3-methoxyaniline, 4-methoxyaniline, 2-methoxy-3-methylaniline, 2-methoxy-4-methylaniline, 2-methoxy-5-methylaniline, 2-methoxy-6-methylaniline, 3-methoxy-2-methylaniline, 3-methoxy-4-methylaniline, 3-methoxy-5-methylaniline, 3-methoxy-6-methylaniline, 4-methoxy-2-methylaniline, 4-methoxy-3-methylaniline, 2-ethoxyaniline, 3-ethoxyaniline, 4-ethoxyaniline, 4-methoxy-5-methylaniline, 4-methoxy-6-methylaniline, 2-methoxy-3-ethylaniline, 2-methoxy-4-ethylaniline, 2-methoxy-5-ethylaniline, 2-methoxy-6-ethylaniline, 3-methoxy-2-ethylaniline, 3-methoxy-4-ethylaniline, 3-methoxy-5-ethylaniline, 3-methoxy-6-ethylaniline, 4-methoxy-2-ethylaniline, 4-methoxy-3-ethylaniline, 2-methoxy-2,3,4-trimethylaniline, 3-methoxy-2,4,5-trimethylaniline, 4-methoxy-2,3,5-trimethylaniline, and mixtures thereof.

6. The post-treated salt of a sulfurized alkylhydroxyaromatic composition of claim 1 , wherein the primary and/or secondary monoamine compound is a secondary monoamine compound selected from the group consisting of dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, diundecylamine, didodecylamine, ditetradecylamine, dihexadecylamine, dimethanolamine, diethanolamine, diphenylamine, dicyclohexylamine and mixtures thereof.

7. The post-treated salt of a sulfurized alkylhydroxyaromatic composition of claim 1 , which is prepared by a process comprising:
(a) providing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition containing an unsulfurized alkyl-substituted bydroxyaromatic compound and its unsulfurized metal salt; wherein the alkyl-substituted hydroxyaromatic compound is derived from alkylation of a hydroxyaromatic compound with one or more olefins comprising C 9 to C 18 oligomers of monomers selected from propylene, butylene or mixtures thereof, and
(b) reacting the salt of a sulfurized alkyl-substituted hydroxyaromatic composition with an effective amount of an aldehyde and a primary and/or secondary monoamine compound having at least one active hydrogen and under reaction conditions sufficient to provide a post-treated salt of the sulfurized alkyl-substituted hydroxyaromatic composition having at least about 70% reduced content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt, compared to the content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt present in the non-post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition.

8. The post-treated salt of a sulfurized alkylhydroxyaromatic compound of claim 7 , having at least about 80% reduced content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt, compared to the content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt present in the non-post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition.

9. The post-treated salt of a sulfurized alkylhydroxyaromatic compound of claim 7 , having at least about 90% reduced content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt, compared to the content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt present in the non-post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition.

10. A process for preparing a post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition having a reduced content of unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt, the process comprising the steps of:
(a) providing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition containing an unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt; wherein the alkyl-substituted hydroxyaromatic compound is derived from alkylation of a hydroxyaromatic compound with one or more olefins comprising C 9 to C 18 oligomers of monomers selected from propylene, butylene or mixtures thereof; and
(b) reacting the salt of a sulfurized alkyl-substituted hydroxyaromatic composition with an effective amount of an aldehyde and a primary and/or secondary monoamine compound having at least one active hydrogen and under reaction conditions sufficient to provide a post-treated salt of the sulfurized alkyl-substituted hydroxyaromatic composition having at least about 70% reduced content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt, compared to the content, by combined mass, of the unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt present in the non-post-treated salt of a sulfurized alkyl-substituted hydroxyaromatic composition.

11. The process of claim 10 , wherein the salt of a

Assignees

• Gibbs Andrew R
• Campbell Curtis
• Chevron Oronite Co

Inventors

• Gibbs Andrew R
• Campbell Curtis

Classifications

• C10N2060/10

  by sulfur or a compound containing sulfur · CPC title

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title

• C10N2040/30

  Refrigerators lubricants {or compressors lubricants} · CPC title

• C10N2040/252

  Diesel engines · CPC title

• C10N2040/04

  Oil-bath; Gear-boxes; Automatic transmissions; Traction drives · CPC title