Formic acid and the high-temperature reductive desulfurization of aromatic sulfides
When diphenyl sulfide is heated with formic acid to 450/sup 0/C, it is converted to benzene, toluene, thiophenol, thioanisole, and benzoic acid. By increasing the time of reaction, diphenyl sulfide is converted completely to benzene and toluene. The mechanism of toluene and benzoic acid formation is...
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| Veröffentlicht in: | J. Org. Chem.; (United States) 1982-10, Vol.47 (21), p.4107-4110 |
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| container_issue | 21 |
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| container_title | J. Org. Chem.; (United States) |
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| creator | Van Buren, Rick L Baltisberger, Richard J Woolsey, Neil F Stenberg, Virgil I |
| description | When diphenyl sulfide is heated with formic acid to 450/sup 0/C, it is converted to benzene, toluene, thiophenol, thioanisole, and benzoic acid. By increasing the time of reaction, diphenyl sulfide is converted completely to benzene and toluene. The mechanism of toluene and benzoic acid formation is studied by kinetic data and by comparing CO and CO/sub 2/ as possible sources for the extra carbon. It is concluded that PhS. and CO are the precursors to benzoic acid, toluene, thiophenol, and thioanisole. Formic acid reacts primarily via the metal surface of the reactor and most probably with radical initiation. |
| doi_str_mv | 10.1021/jo00142a019 |
| format | Article |
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By increasing the time of reaction, diphenyl sulfide is converted completely to benzene and toluene. The mechanism of toluene and benzoic acid formation is studied by kinetic data and by comparing CO and CO/sub 2/ as possible sources for the extra carbon. It is concluded that PhS. and CO are the precursors to benzoic acid, toluene, thiophenol, and thioanisole. Formic acid reacts primarily via the metal surface of the reactor and most probably with radical initiation.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00142a019</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>01 COAL, LIGNITE, AND PEAT ; 010402 - Coal, Lignite, & Peat- Purification & Upgrading ; 400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987) ; AROMATICS ; CARBOXYLIC ACIDS ; CHEMICAL REACTION KINETICS ; CHEMICAL REACTIONS ; CONVERSION ; DESULFURIZATION ; FORMIC ACID ; HIGH TEMPERATURE ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; KINETICS ; MONOCARBOXYLIC ACIDS ; ORGANIC ACIDS ; ORGANIC COMPOUNDS ; ORGANIC SULFUR COMPOUNDS ; REACTION KINETICS ; TEMPERATURE EFFECTS</subject><ispartof>J. Org. 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Org. Chem.; (United States)</title><addtitle>J. Org. Chem</addtitle><description>When diphenyl sulfide is heated with formic acid to 450/sup 0/C, it is converted to benzene, toluene, thiophenol, thioanisole, and benzoic acid. By increasing the time of reaction, diphenyl sulfide is converted completely to benzene and toluene. The mechanism of toluene and benzoic acid formation is studied by kinetic data and by comparing CO and CO/sub 2/ as possible sources for the extra carbon. It is concluded that PhS. and CO are the precursors to benzoic acid, toluene, thiophenol, and thioanisole. Formic acid reacts primarily via the metal surface of the reactor and most probably with radical initiation.</description><subject>01 COAL, LIGNITE, AND PEAT</subject><subject>010402 - Coal, Lignite, & Peat- Purification & Upgrading</subject><subject>400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)</subject><subject>AROMATICS</subject><subject>CARBOXYLIC ACIDS</subject><subject>CHEMICAL REACTION KINETICS</subject><subject>CHEMICAL REACTIONS</subject><subject>CONVERSION</subject><subject>DESULFURIZATION</subject><subject>FORMIC ACID</subject><subject>HIGH TEMPERATURE</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>KINETICS</subject><subject>MONOCARBOXYLIC ACIDS</subject><subject>ORGANIC ACIDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC SULFUR COMPOUNDS</subject><subject>REACTION KINETICS</subject><subject>TEMPERATURE EFFECTS</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1982</creationdate><recordtype>article</recordtype><recordid>eNpt0E1LAzEQBuAgCtbqyT8QvHiQ1XxssrtHKbYKBQut4i2k-XBTu7slyYr6601ZEQ_OZRjm4YUZAM4xusaI4JtNhxDOiUS4OgAjzAjKeIXyQzBCiJCMEk6PwUkIG5SKMTYCy2nnG6egVE5D2WoYawNr91pn0TQ742XsvYHe6F5F926gNqHf2t67Lxld18LOQum7Jg0K7jcugVNwZOU2mLOfPgZP07vV5D6bP84eJrfzTFJSxkzjilKGqsrmBSvztdZcFSVF1LKccZ6bnGtrUSElNpxKqmlpizxZtF5XpDB0DC6G3C5EJ4Jy0ahadW1rVBScEVpymtDVgJTvQvDGip13jfSfAiOxf5r487Sks0G7EM3HL5X-TfCCFkysFkuBp_RlQmYL8Zz85eClCimo9206-N_kb08FeoU</recordid><startdate>19821001</startdate><enddate>19821001</enddate><creator>Van Buren, Rick L</creator><creator>Baltisberger, Richard J</creator><creator>Woolsey, Neil F</creator><creator>Stenberg, Virgil I</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>19821001</creationdate><title>Formic acid and the high-temperature reductive desulfurization of aromatic sulfides</title><author>Van Buren, Rick L ; Baltisberger, Richard J ; Woolsey, Neil F ; Stenberg, Virgil I</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a328t-d19335099f47584bdd6c78303f545664e46dff07aa1e63a3d38f744750bb927e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1982</creationdate><topic>01 COAL, LIGNITE, AND PEAT</topic><topic>010402 - Coal, Lignite, & Peat- Purification & Upgrading</topic><topic>400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)</topic><topic>AROMATICS</topic><topic>CARBOXYLIC ACIDS</topic><topic>CHEMICAL REACTION KINETICS</topic><topic>CHEMICAL REACTIONS</topic><topic>CONVERSION</topic><topic>DESULFURIZATION</topic><topic>FORMIC ACID</topic><topic>HIGH TEMPERATURE</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>KINETICS</topic><topic>MONOCARBOXYLIC ACIDS</topic><topic>ORGANIC ACIDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC SULFUR COMPOUNDS</topic><topic>REACTION KINETICS</topic><topic>TEMPERATURE EFFECTS</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Van Buren, Rick L</creatorcontrib><creatorcontrib>Baltisberger, Richard J</creatorcontrib><creatorcontrib>Woolsey, Neil F</creatorcontrib><creatorcontrib>Stenberg, Virgil I</creatorcontrib><creatorcontrib>Univ. of North Dakota, Grand Forks</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>J. Org. Chem.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Van Buren, Rick L</au><au>Baltisberger, Richard J</au><au>Woolsey, Neil F</au><au>Stenberg, Virgil I</au><aucorp>Univ. of North Dakota, Grand Forks</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formic acid and the high-temperature reductive desulfurization of aromatic sulfides</atitle><jtitle>J. Org. Chem.; (United States)</jtitle><addtitle>J. Org. Chem</addtitle><date>1982-10-01</date><risdate>1982</risdate><volume>47</volume><issue>21</issue><spage>4107</spage><epage>4110</epage><pages>4107-4110</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>When diphenyl sulfide is heated with formic acid to 450/sup 0/C, it is converted to benzene, toluene, thiophenol, thioanisole, and benzoic acid. By increasing the time of reaction, diphenyl sulfide is converted completely to benzene and toluene. The mechanism of toluene and benzoic acid formation is studied by kinetic data and by comparing CO and CO/sub 2/ as possible sources for the extra carbon. It is concluded that PhS. and CO are the precursors to benzoic acid, toluene, thiophenol, and thioanisole. Formic acid reacts primarily via the metal surface of the reactor and most probably with radical initiation.</abstract><cop>United States</cop><pub>American Chemical Society</pub><doi>10.1021/jo00142a019</doi><tpages>4</tpages></addata></record> |
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| issn | 0022-3263 1520-6904 |
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| source | ACS Publications |
| subjects | 01 COAL, LIGNITE, AND PEAT 010402 - Coal, Lignite, & Peat- Purification & Upgrading 400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987) AROMATICS CARBOXYLIC ACIDS CHEMICAL REACTION KINETICS CHEMICAL REACTIONS CONVERSION DESULFURIZATION FORMIC ACID HIGH TEMPERATURE INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY KINETICS MONOCARBOXYLIC ACIDS ORGANIC ACIDS ORGANIC COMPOUNDS ORGANIC SULFUR COMPOUNDS REACTION KINETICS TEMPERATURE EFFECTS |
| title | Formic acid and the high-temperature reductive desulfurization of aromatic sulfides |
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