# US 10,501,408 B2 · Methods for producing thiol compounds and sulfide compounds using diphenylamine or a phenol compound > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,408 B2 - Document ID: US10501408B2 - Status: Granted - Kind: B2 - Application number: 16/210,404 - Filed: 2018-12-05 - Published: 2019-04-11 - Granted: 2019-12-10 - Earliest claimed: 2016-09-12 - Assignees: Chevron Phillips Chemical Company LP - Applicants: Chevron Phillips Chemical Company LP - Inventors: Kenneth M. Lassen - Web page: https://patentgrep.com/patent/US10501408B2 ## CPC - C07C 319/18: by addition of thiols to unsaturated compounds - B01J 19/123: {Ultraviolet light} - C07C 319/04: by addition of hydrogen sulfide or its salts to unsaturated compounds - C07C 2601/14: The ring being saturated - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS ## Abstract The present invention discloses processes for producing a thiol compound or a sulfide compound from an olefin compound. Diphenylamine or a phenol compound can be used to increase the rate of conversion of the olefin compound to the thiol compound or the sulfide compound. ## Claims ### Claim 1 A process for producing a thiol compound, the process comprising: i) contacting: a) an olefin compound; b) H2S; c) diphenylamine and/or a phenol compound; and d) a photoinitiator and/or a free radical initiator; and ii) forming the thiol compound. ### Claim 2 (depends on 1) The process of claim 1, wherein the phenol is an alkyl phenol. ### Claim 3 (depends on 1) The process of claim 1, wherein a molar ratio of H2S to carbon-carbon double bonds of the olefin compound is from about 2:1 to about 150:1. ### Claim 4 (depends on 1) The process of claim 1, wherein: an amount of diphenylamine and/or the phenol compound is in a range from about 0.1 wt. % to about 1 wt. %, based on the weight of the olefin compound; and an amount of the photoinitiator and/or the free radical initiator is in a range from about 0.05 wt. % to about 5 wt. %, based on the weight of the olefin compound. ### Claim 5 (depends on 1) The process of claim 1, wherein the thiol compound is formed in the presence of ultraviolet light. ### Claim 6 (depends on 1) The process of claim 1, wherein the olefin compound comprises ethylene, propylene, 1-butene, 2-butene, 3-methyl-1-butene, isobutylene, 1-pentene, 2-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 1-hexene, 2-hexene, 3-ethyl-1-hexene, 1-heptene, 2-heptene, 3-heptene, 1-octene, 1-decene, 1-dodecene, styrene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, or any combination thereof. ### Claim 7 (depends on 1) The process of claim 1, wherein the olefin compound comprises limonene, butadiene, isoprene, cyclobutadiene, cyclopentadiene, cyclohexadiene, cyclooctadiene, norbornadiene, vinylcyclohexene, vinylnorbornene, divinylbenzene, cyclopentadiene dimer, trivinylcyclohexane, trivinylbenzene, cycloheptatriene, dimethyl heptatriene, octatriene, cyclooctatriene, cyclododecatriene, cyclooctatetraene, cyclododecatetraene, a polybutadiene, or any combination thereof. ### Claim 8 (depends on 1) The process of claim 1, wherein the process comprises: contacting the olefin compound, H2S, diphenylamine, and the photoinitiator; and forming the thiol compound in the presence of ultraviolet light; wherein a molar percent conversion of the olefin compound is at least about 90%; and wherein a percent conversion of the olefin compound is greater than a percent conversion obtained by conducting the process without diphenylamine, under the same reaction conditions. ### Claim 9 (depends on 1) The process of claim 1, wherein the process comprises: contacting the olefin compound, H2S, the phenol compound, and the photoinitiator; and forming the thiol compound in the presence of ultraviolet light; wherein a percent conversion of the olefin compound is greater than a percent conversion obtained by conducting the process without the phenol compound, under the same reaction conditions. ### Claim 10 (depends on 1) The process of claim 1, wherein a molar percent conversion of the olefin compound is at least about 90%. ### Claim 11 (depends on 1) The process of claim 1, wherein the process further comprises a step of removing at least a portion of the olefin compound, of the H2S, of the diphenylamine and/or the phenol compound, of the photoinitiator and/or the free radical initiator, or combinations thereof, from the thiol compound. ### Claim 12 (depends on 1) The process of claim 1, wherein the thiol compound is formed in the presence of a solvent. ### Claim 13 (depends on 1) The process of claim 1 wherein at least 65% of the carbon-carbon double bonds of the olefin compound react to form a thiol group. ### Claim 14 A process for producing a sulfide compound, the process comprising: i) contacting: a) an olefin compound; b) a mercaptan compound; and c) diphenylamine and/or a phenol compound; and ii) forming the sulfide compound; wherein an amount of diphenylamine and/or the phenol compound is in a range from about 0.05 wt. % to about 5 wt. %, based on the weight of the olefin compound. ### Claim 15 (depends on 14) The process of claim 14, wherein a molar ratio of —SH of the mercaptan compound to carbon-carbon double bonds of the olefin compound is in a range from about 2:1 to about 1:2. ### Claim 16 (depends on 14) The process of claim 14, wherein the mercaptan compound comprises methyl mercaptan, ethyl mercaptan, n-propyl mercaptan, n-butyl mercaptan, t-butyl mercaptan, n-pentyl mercaptan, phenyl mercaptan, mercaptomethanol, 2-mercaptoethanol, 3-mercaptopropanol, 4-mercaptobutanol, 5-mercaptopentanol, 6-mercaptohexanol, or any combination thereof. ### Claim 17 (depends on 14) The process of claim 14, wherein the amount of diphenylamine and/or the phenol compound is in a range from about 0.1 wt. % to about 1 wt. %, based on the weight of the olefin compound. ### Claim 18 (depends on 14) The process of claim 14, wherein the process comprises: contacting the olefin compound, the mercaptan compound, diphenylamine, and a photoinitiator and/or free radical initiator; and forming the sulfide compound in the presence of ultraviolet light; wherein a percent conversion of the olefin compound is greater than a percent conversion obtained by conducting the process without diphenylamine, under the same reaction conditions. ### Claim 19 (depends on 14) The process of claim 14, wherein the process comprises: contacting the olefin compound, the mercaptan compound, the phenol compound, and a photoinitiator and/or free radical initiator; and forming the sulfide compound in the presence of ultraviolet light; wherein a percent conversion of the olefin compound is greater than a percent conversion obtained by conducting the process without the phenol compound, under the same reaction conditions. ### Claim 20 A process for producing a sulfide compound, the process comprising: i) contacting: a) an olefin compound; b) a mercaptan compound; and c) diphenylamine and/or a phenol compound; and ii) forming the sulfide compound; wherein a molar percent conversion of the olefin compound is at least about 90%. ### Claim 21 (depends on 20) The process of claim 20, wherein the process comprises: contacting the olefin compound, the mercaptan compound, diphenylamine, and a photoinitiator and/or free radical initiator; and forming the sulfide compound in the presence of ultraviolet light. ### Claim 22 (depends on 20) The process of claim 20, wherein the process comprises: contacting the olefin compound, the mercaptan compound, the phenol compound, and a photoinitiator and/or free radical initiator; and forming the sulfide compound in the presence of ultraviolet light.