# US 5,344,967 A · Treatment of organic sulfonic acid > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,344,967 A - Document ID: US5344967A - Status: Granted - Kind: A - Application number: 07/723,144 - Filed: 1991-06-28 - Granted: 1994-09-06 - Earliest claimed: 1991-06-28 - Assignees: The Lubrizol Corporation - Inventors: Eric R. Schnur; David L. Westfall - Web page: https://patentgrep.com/patent/US5344967A ## CPC - C07C 303/42: Separation; Purification; Stabilisation; Use of additives - C07G 99/0024: {Overbased compounds} - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07G: COMPOUNDS OF UNKNOWN CONSTITUTION (sulfonated fats, oils or waxes of undetermined constitution C07C309/62) ## Abstract The present invention describes treating an organic sulfonic acid with an olefin to obtain an improvement in color of the resultant salts and to lessen the amount of inactive components in the composition. ## Claims ### Claim 1 In the process of treating an organic sulfonic acid the steps comprising; contacting the organic sulfonic acid with at least 0.3 weight part of an unsaturated hydrocarbon per 100 weight parts of the organic sulfonic acid to obtain a mixture, wherein the unsaturated hydrocarbon has a number average molecular weight between about 600 and 3,000 wherein the organic sulfonic acid is neutralized and contacted with a filter aid. ### Claim 2 (depends on 1) The process of claim 1 wherein the mixture of the sulfonic acid and the unsaturated hydrocarbon are at about 70.degree. F. (23.degree. C.) to about 175.degree. F. (80.degree. C.) immediately after forming the mixture. ### Claim 3 (depends on 1) The process of claim 1 wherein the mixture of the organic sulfonic acid and the unsaturated hydrocarbon are heated to a temperature of about 140.degree. F. (60.degree. C.) to about 350.degree. F. (177.degree. C.) after the mixture is formed. ### Claim 4 (depends on 1) The process of claim 1 wherein the organic sulfonic acid is contacted with a non-reactive gas. ### Claim 5 (depends on 3) The process of claim 3 wherein the amount of unsaturated hydrocarbon added to the organic sulfonic acid is sufficient to improve the color of the resultant mixture when compared to an organic sulfonic acid which is not treated with the unsaturated hydrocarbon. ### Claim 6 (depends on 1) The process of claim 1 wherein the organic sulfonic acid further contains a second unsaturated hydrocarbon having a number average molecular weight of about 200 to about 599. ### Claim 7 (depends on 1) The process of claim 1 wherein the organic sulfonic acid is an alkyl substituted aromatic sulfonic acid. ### Claim 8 (depends on 4) The process of claim 4 wherein the contacting of the organic sulfonic acid with the non-reactive gas lowers the level of any sulfur dioxide present. ### Claim 9 (depends on 8) The process of claim 8 wherein the treatment of the organic sulfonic acid with the non-reactive gas to lower the presence of sulfur dioxide is done prior to, or substantially contemporaneously with, the introduction of the unsaturated hydrocarbon. ### Claim 10 (depends on 1) The process of claim 1 wherein the unsaturated hydrocarbon is an alpha olefin. ### Claim 11 (depends on 3) The process of claim 3 wherein the mixture of the organic sulfonic acid and the unsaturated hydrocarbon are heated to a temperature of about 180.degree. F. (82.degree. C.) to about 300.degree. F. (149.degree. C.) after the mixture is formed. ### Claim 12 (depends on 11) The process of claim 11 wherein the organic sulfonic acid is an alkyl substituted aromatic sulfonic acid. ### Claim 13 (depends on 2) The process of claim 2 wherein the mixture of the organic sulfonic acid and the unsaturated hydrocarbon are at about 80.degree. F. (27.degree. C.) to about 165.degree. F. (74.degree. C.) immediately after forming the mixture. ### Claim 14 (depends on 12) The process of claim 12 wherein the alkyl substituted aromatic sulfonic acid is an alkyl substituted toluene sulfonic acid. ### Claim 15 (depends on 4) The process of claim 4 wherein the non-reactive gas is selected from the group consisting of nitrogen, air and carbon dioxide and mixtures thereof. ### Claim 16 (depends on 12) The process of claim 12 wherein the alkyl substituted aromatic sulfonic acid is an alkyl substituted xylene sulfonic acid. ### Claim 17 (depends on 12) The process of claim 12 wherein the alkyl substituted aromatic sulfonic acid is an alkyl substituted benzene sulfonic acid. ### Claim 18 (depends on 12) The process of claim 12 wherein the mixture of the organic sulfonic acid and the unsaturated hydrocarbon are heated to a temperature of about 140.degree. F. (60.degree. C.) to about 300.degree. F. (149.degree. C.) after the mixture is formed. ### Claim 19 (depends on 1) The process of claim 1 wherein the unsaturated hydrocarbon is selected from the group consisting of polypropylene and a polybutene and mixtures thereof. ### Claim 20 (depends on 19) The process of claim 19 wherein the unsaturated hydrocarbon is polyisobutylene. ### Claim 21 The process of treating a mixture of an alkyl substituted aromatic sulfonic acid and a source of sulfur dioxide wherein an alkyl substituted aromatic compound is contacted with a sulfonating agent to obtain the alkyl substituted aromatic sulfonic acid, and the alkyl substituted aromatic sulfonic acid and source of sulfur dioxide is then processed to reduce the sulfur dioxide content of the mixture by introducing a relatively non-reactive gas to the mixture and maintaining the mixture at a temperature of about 70.degree. F. (23.degree. C.) to about 175.degree. F. (80.degree. C.) for a period of time sufficient to reduce the sulfur dioxide content, and contacting the alkyl substituted aromatic sulfonic acid with an unsaturated hydrocarbon having a number average molecular weight between about 600 and 3,000 wherein the alkyl substituted aromatic sulfonic acid is neutralized and contacted with a filter aid. ### Claim 22 (depends on 21) The process of claim 21 wherein the mixture following contacting with the unsaturated hydrocarbon is heated to a temperature of from 140.degree. F. (60.degree. C.) to 350.degree. F. (177.degree. C.). ### Claim 23 (depends on 21) The process of claim 21 wherein the alkyl substituted aromatic sulfonic acid is contacted with a second unsaturated hydrocarbon having a number average molecular weight of about 200 to about 599. ### Claim 24 (depends on 22) The process of claim 22 wherein the amount of unsaturated hydrocarbon added to the alkyl substituted aromatic sulfonic acid is sufficient to improve the color of the resultant mixture when compared to an alkyl substituted sulfonic acid which is not treated with the unsaturated hydrocarbon. ### Claim 25 (depends on 21) The process of claim 21 wherein sulfur dioxide is generated during the formation of the alkyl substituted aromatic sulfonic acid. ### Claim 26 (depends on 21) The process of claim 21 wherein the treatment of the alkyl substituted aromatic sulfonic acid with the non-reactive gas to reduce the presence of sulfur dioxide is done prior to, or substantially contemporaneously with, the introduction of the unsaturated hydrocarbon. ### Claim 27 (depends on 21) The process of claim 21 wherein the unsaturated hydrocarbon is an alpha olefin. ### Claim 28 (depends on 21) The process of claim 21 wherein the mixture of the alkyl substituted aromatic sulfonic acid and the unsaturated hydrocarbon are heated to a temperature of about 180.degree. F. (82.degree. C.) about 399.degree. F. (149.degree. C.) after the mixture is formed. ### Claim 29 (depends on 21) The process of claim 21 wherein the unsaturated hydrocarbon is selected from the group consisting of polypropylene and a polybutene and mixtures thereof. ### Claim 30 (depends on 29) The process of claim 29 wherein the unsaturated hydrocarbon is polyisobutylene. ### Claim 31 (depends on 21) The process of claim 21 wherein the mixture of the alkyl substituted aromatic sulfonic acid and the unsaturated hydrocarbon are at about 80.degree. F. (27.degree. C.) to about 165.degree. F. (74.degree. C.) immediately after forming the mixture. ### Claim 32 (depends on 21) The process of claim 21 wherein the alkyl substituted aromatic sulfonic acid is an alkyl substituted toluene sulfonic acid. ### Claim 33 (depends on 21) The process of claim 21 wherein the alkyl substituted aromatic sulfonic acid is an alkyl substituted benzene sulfonic acid. ### Claim 34 (depends on 21) The process of claim 21 wherein the alkyl substituted aromatic sulfonic acid is an alkyl substituted xylene sulfonic acid. ### Claim 35 (depends on 21) The process of claim 21 wherein the non-reactive gas is selected from the group consisting of nitrogen, air and carbon dioxide and mixtures thereof.