# US 8,772,209 B2 · Process for preparing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,772,209 B2 - Document ID: US8772209B2 - Status: Granted - Kind: B2 - Application number: 13/682,172 - Filed: 2012-11-20 - Published: 2014-05-22 - Granted: 2014-07-08 - Earliest claimed: 2012-11-20 - Assignees: Chevron Oronite Company LLS - Applicants: Chevron Oronite Company LLC - Inventors: Cedrick Mahieux; Richard Dutta; Curtis Campbell - Web page: https://patentgrep.com/patent/US8772209B2 ## CPC - C10M 159/20: Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products - C10M 2219/089: Overbased salts - C10N 2030/04: Detergent property or dispersant property - C10N 2030/64: {Environmental friendly compositions} - C10N 2070/00: Specific manufacturing methods for lubricant compositions - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract Disclosed herein is a process for preparing a 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 involves the steps of: (a) providing a composition comprising (i) a salt of a sulfurized alkyl-substituted hydroxyaromatic compound; (ii) an unsulfurized alkyl-substituted hydroxyaromatic compound and (iii) an unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound; wherein the alkyl-substituted hydroxyaromatic compound is derived from alkylation of a hydroxyaromatic compound with one or more olefins comprising C9 to C18 oligomers of monomers selected from propylene, butylene or mixtures thereof; (b) protonating the unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound with an effective amount of an acidic compound capable of protonating the unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound; and (c) removing the unsulfurized alkyl-substituted hydroxyaromatic compound and the protonated unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound from the composition. ## Claims ### Claim 1 A process for preparing a 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 composition comprising (i) a salt of a sulfurized alkyl-substituted hydroxyaromatic compound; (ii) an unsulfurized alkyl-substituted hydroxyaromatic compound and (iii) an unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound; wherein the alkyl-substituted hydroxyaromatic compound is derived from alkylation of a hydroxyaromatic compound with one or more olefins comprising C9 to C18oligomers of monomers selected from propylene, butylene or mixtures thereof; (b) protonating the unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound with an effective amount of an acidic compound capable of protonating the unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound; and (c) removing the unsulfurized alkyl-substituted hydroxyaromatic compound and the protonated unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound from the composition wherein the salt of the sulfurized alkyl-substituted hydroxyaromatic composition obtained in step (c) contains less than or equal to 2.45 wt. % of the unsulfurized alkyl-substituted hydroxyaromatic compound and its metal salt. ### Claim 2 (depends on 1) The process of claim 1, wherein the hydroxyaromatic compound is a phenol and the one or more olefins comprising C9 to C18 oligomers are one or more olefins comprising C9 to C18 propylene oligomers. ### Claim 3 (depends on 1) The process of claim 1, wherein the salt of a sulfurized alkyl-substituted hydroxyaromatic composition provided in step (a) is an overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition. ### Claim 4 (depends on 1) The process of claim 1, wherein the acidic compound is a saturated or unsaturated carboxylic acid. ### Claim 5 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is selected from the group consisting of a saturated or unsaturated aliphatic monocarboxylic acid, a saturated or unsaturated cycloaliphatic monocarboxylic acid, a saturated or unsaturated aromatic monocarboxylic acid, a saturated or unsaturated aliphatic dicarboxylic acid, a saturated or unsaturated cycloaliphatic dicarboxylic acid, a saturated or unsaturated aromatic dicarboxylic acid, a saturated or unsaturated aliphatic tricarboxylic acid, a saturated or unsaturated cycloaliphatic tricarboxylic acid, a saturated or unsaturated aromatic tricarboxylic acid and mixtures thereof. ### Claim 6 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is selected from the group consisting of formic acid, acetic acid, phenylacetic acid, propionic acid, alanine, butyric acid, hydroxybutyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, 2-methylpropionic acid, 2-methylbutyric acid, 3-methylbutyric acid, 2-methylpentanoic acid, 2-ethylhexanoic acid, 2-propylheptanoic acid, pivalic acid, neononanoic acid, neodecanoic acid, neotridecanoic acid, stearic acid, myristic acid, palmitic acid, linolic acid, linoleic acid, oleic acid, lauric acid, acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, and mixtures thereof. ### Claim 7 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is a C4 to C22 linear saturated or unsaturated monocarboxylic acid selected from the group consisting of butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, myristic acid, tridecylic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, myristoleic acid, oleic acid, arachidonic acid, linoleic acid, and mixtures thereof. ### Claim 8 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is an aromatic monocarboxylic acid selected from the group consisting of benzoic acid, nitrobenzoic acid, monohydroxybenzoic acid such as salicylic, 3-hydroxybenzoic acid and 4-hydroxybenzoic acid, alkylhydroxybenzoic acid, chlorobenzoic acid, methoxybenzoic acid, t-butyl benzoic acid, methylbenzoic acid, phenyl acetic acid, 3-phenyl propionic acid, 4-phenyl butyric acid, 3-(p-chlorophenyl) butanoic acid, and mixtures thereof. ### Claim 9 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is an aliphatic dicarboxylic acid selected from the group consisting of oxalic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, malonic acid, succinic acid, glutaric acid, adipic acid, maleic acid and fumaric acid, Examples of aromatic dicarboxylic acids include, but are not limited to, phthalic acid, terephthalic acid, isophthalic acid, 1,5-naphthalene dicarboxylic acid, 1,4-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, 2,8-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, traumatic acid, muconic acid and mixtures thereof. ### Claim 10 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is an aromatic dicarboxylic acid selected from the group consisting of phthalic acid, terephthalic acid, isophthalic acid, 1,5-naphthalene dicarboxylic acid, 1,4-naphthalene dicarboxylic acid, 1,8-naphthalene dicarboxylic acid, 2,8-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, traumatic acid, muconic acid, and mixtures thereof. ### Claim 11 (depends on 4) The process of claim 4, wherein the saturated or unsaturated carboxylic acid is a tricarboxylic acid selected from the group consisting of citric acid, isocitric acid, aconitic acid (unsaturated), carbalyllic acid mellitic (benzenehexacarboxylic) acid, and mixtures thereof. ### Claim 12 (depends on 1) The process of claim 1, wherein the acidic compound is a polyalkenyl succinic acid or anhydride thereof. ### Claim 13 (depends on 1) The process of claim 1, wherein the acidic compound is an aliphatic sulfonic acid, aromatic sulfonic acid or mixtures thereof. ### Claim 14 (depends on 13) The process of claim 13, wherein the aliphatic sulfonic acid is selected from the group consisting of methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butansulfonic acid, pentanesulfonic acid, hexanesulfonic acid and mixtures thereof. ### Claim 15 (depends on 13) The process of claim 13, wherein the aromatic sulfonic acids is selected from the group consisting of benzenesulfonic acid, naphthalenesulfonic acid, p-toluenesulfonic acid, p-methoxybenzenesulfonic acid and mixtures thereof. ### Claim 16 (depends on 1) The process of claim 1, wherein the acidic compound is an amine or ammonium salt. ### Claim 17 (depends on 1) The process of claim 1, wherein the effective amount of the acidic compound is from about 1 wt. % to about 25 wt. %, based on the total amount of the neutral or overbased salt of a sulfurized alkyl-substituted hydroxyaromatic composition. ### Claim 18 (depends on 1) The process of claim 1, wherein the step of removing the unsulfurized alkyl-substituted hydroxyaromatic compound and the protonated unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound from the composition comprises distilling the unsulfurized alkyl-substituted hydroxyaromatic compound and the protonated unsulfurized metal salt of the alkyl-substituted hydroxyaromatic compound from the composition of step (b). ### Claim 19 (depends on 1) The process of claim 1, wherein the salt of the sulfurized alkyl-substituted hydroxyaromatic composition obtained in step (c) contains less than about 1.5 wt. % of the unsulfurized alkyl-substituted hydroxyaromatic compound and its metal salt. ### Claim 20 (depends on 1) The process of claim 1, wherein the salt of the sulfurized alkyl-substituted hydroxyaromatic composition obtained in step (c) contains less than about 0.3 wt. % of the unsulfurized alkyl-substituted hydroxyaromatic compound and its metal salt.