Selective Hydrogenation of Lactic Acid to 1,2-Propanediol over Highly Active Ruthenium-Molybdenum Oxide Catalysts
Modification of Ru/C with a small amount of MoOx (RuMoOx/C) enhanced the catalytic activity in the hydrogenation of L‐lactic acid to form 1,2‐propanediol and maintained high selectivity. The turnover frequency based on the amount of Ru over the optimized RuMoOx/C catalyst (Mo/Ru molar ratio=1:16)...
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| Veröffentlicht in: | ChemSusChem 2015-04, Vol.8 (7), p.1170-1178 |
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| creator | Takeda, Yasuyuki Shoji, Tomohiro Watanabe, Hideo Tamura, Masazumi Nakagawa, Yoshinao Okumura, Kazu Tomishige, Keiichi |
| description | Modification of Ru/C with a small amount of MoOx (RuMoOx/C) enhanced the catalytic activity in the hydrogenation of L‐lactic acid to form 1,2‐propanediol and maintained high selectivity. The turnover frequency based on the amount of Ru over the optimized RuMoOx/C catalyst (Mo/Ru molar ratio=1:16) was 114 h−1 at 393 K, which was about 4 times higher than that over Ru/C. The same effect of MoOx was obtained over RuMoOx/SiO2, although RuMoOx/SiO2 showed slightly lower activity than that of RuMoOx/C. RuMoOx/C achieved a high yield of 95 % in 18 h at 393 K and was applicable to various carboxylic acids to provide the corresponding alcohols in high yields. Modification with MoOx also brought about suppression of racemization and (S)‐1,2‐propanediol was obtained in high enantiomeric excess at 353 K. Based on kinetic analysis and characterization data, such as XRD, TEM, CO adsorption by a volumetric method, FTIR spectroscopy, and X‐ray absorption spectroscopy, for RuMoOx/C and RuMoOx/SiO2, the catalyst structure and reaction mechanism are proposed.
Minor adjustment for major effects: Modification of supported ruthenium catalysts with a small amount of molybdenum oxide (RuMoOx/C, RuMoOx/SiO2) enhances the catalytic activity for the hydrogenation of L‐lactic acid to give (S)‐1,2‐propanediol with high selectivity. The turnover frequency is roughly four times higher than over Ru/C. The results reported are encouraging for the design of selective hydrogenation catalysts and the development of synthesis methods of alcohols. |
| doi_str_mv | 10.1002/cssc.201403011 |
| format | Article |
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Minor adjustment for major effects: Modification of supported ruthenium catalysts with a small amount of molybdenum oxide (RuMoOx/C, RuMoOx/SiO2) enhances the catalytic activity for the hydrogenation of L‐lactic acid to give (S)‐1,2‐propanediol with high selectivity. The turnover frequency is roughly four times higher than over Ru/C. The results reported are encouraging for the design of selective hydrogenation catalysts and the development of synthesis methods of alcohols.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.201403011</identifier><identifier>PMID: 25510671</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Adsorption ; carboxylic acids ; Catalysis ; enantioselectivity ; Hydrogenation ; Kinetics ; Lactic Acid - chemistry ; molybdenum ; Molybdenum - chemistry ; Oxides - chemistry ; Propylene Glycol - chemistry ; ruthenium ; Ruthenium - chemistry ; Spectrum analysis ; X-rays</subject><ispartof>ChemSusChem, 2015-04, Vol.8 (7), p.1170-1178</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5841-debe2e025efe72a8652a127ac17d5fb5a22d19e4b769a02d4f9c02419c895a623</citedby><cites>FETCH-LOGICAL-c5841-debe2e025efe72a8652a127ac17d5fb5a22d19e4b769a02d4f9c02419c895a623</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcssc.201403011$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.201403011$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25510671$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Takeda, Yasuyuki</creatorcontrib><creatorcontrib>Shoji, Tomohiro</creatorcontrib><creatorcontrib>Watanabe, Hideo</creatorcontrib><creatorcontrib>Tamura, Masazumi</creatorcontrib><creatorcontrib>Nakagawa, Yoshinao</creatorcontrib><creatorcontrib>Okumura, Kazu</creatorcontrib><creatorcontrib>Tomishige, Keiichi</creatorcontrib><title>Selective Hydrogenation of Lactic Acid to 1,2-Propanediol over Highly Active Ruthenium-Molybdenum Oxide Catalysts</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>Modification of Ru/C with a small amount of MoOx (RuMoOx/C) enhanced the catalytic activity in the hydrogenation of L‐lactic acid to form 1,2‐propanediol and maintained high selectivity. The turnover frequency based on the amount of Ru over the optimized RuMoOx/C catalyst (Mo/Ru molar ratio=1:16) was 114 h−1 at 393 K, which was about 4 times higher than that over Ru/C. The same effect of MoOx was obtained over RuMoOx/SiO2, although RuMoOx/SiO2 showed slightly lower activity than that of RuMoOx/C. RuMoOx/C achieved a high yield of 95 % in 18 h at 393 K and was applicable to various carboxylic acids to provide the corresponding alcohols in high yields. Modification with MoOx also brought about suppression of racemization and (S)‐1,2‐propanediol was obtained in high enantiomeric excess at 353 K. Based on kinetic analysis and characterization data, such as XRD, TEM, CO adsorption by a volumetric method, FTIR spectroscopy, and X‐ray absorption spectroscopy, for RuMoOx/C and RuMoOx/SiO2, the catalyst structure and reaction mechanism are proposed.
Minor adjustment for major effects: Modification of supported ruthenium catalysts with a small amount of molybdenum oxide (RuMoOx/C, RuMoOx/SiO2) enhances the catalytic activity for the hydrogenation of L‐lactic acid to give (S)‐1,2‐propanediol with high selectivity. The turnover frequency is roughly four times higher than over Ru/C. The results reported are encouraging for the design of selective hydrogenation catalysts and the development of synthesis methods of alcohols.</description><subject>Adsorption</subject><subject>carboxylic acids</subject><subject>Catalysis</subject><subject>enantioselectivity</subject><subject>Hydrogenation</subject><subject>Kinetics</subject><subject>Lactic Acid - chemistry</subject><subject>molybdenum</subject><subject>Molybdenum - chemistry</subject><subject>Oxides - chemistry</subject><subject>Propylene Glycol - chemistry</subject><subject>ruthenium</subject><subject>Ruthenium - chemistry</subject><subject>Spectrum analysis</subject><subject>X-rays</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU1v1DAURS0EoqWwZYkssWFBBj8ndpJlFZVOxUARw0d3lmO_tC5JPLWTtvn3ZJgyQmxY2ZLPPX56l5CXwBbAGH9nYjQLziBjKQN4RA6hkFkiZHbxeH9P4YA8i_GaMclKKZ-SAy4EMJnDIblZY4tmcLdIl5MN_hJ7PTjfU9_QlZ4fDD02ztLBU3jLk8_Bb3SP1vmW-lsMdOkur9ppZn4rvozDFfZu7JKPvp1qi_3Y0fN7Z5FWetDtFIf4nDxpdBvxxcN5RL69P_laLZPV-elZdbxKjCgySCzWyJFxgQ3mXBdScA081wZyK5paaM4tlJjVuSw14zZrSsN4BqUpSqElT4_Im513E_zNiHFQnYsG23ae349Rgcy5BC6KLfr6H_Taj6Gfp9tSAIWYf56pxY4ywccYsFGb4DodJgVMbctQ2zLUvow58OpBO9Yd2j3-Z_szUO6AO9fi9B-dqtbr6m95ssu6OOD9PqvDTyXzNBfqx6dTxdcfLtLvRapW6S-kTaT_</recordid><startdate>20150413</startdate><enddate>20150413</enddate><creator>Takeda, Yasuyuki</creator><creator>Shoji, Tomohiro</creator><creator>Watanabe, Hideo</creator><creator>Tamura, Masazumi</creator><creator>Nakagawa, Yoshinao</creator><creator>Okumura, Kazu</creator><creator>Tomishige, Keiichi</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20150413</creationdate><title>Selective Hydrogenation of Lactic Acid to 1,2-Propanediol over Highly Active Ruthenium-Molybdenum Oxide Catalysts</title><author>Takeda, Yasuyuki ; Shoji, Tomohiro ; Watanabe, Hideo ; Tamura, Masazumi ; Nakagawa, Yoshinao ; Okumura, Kazu ; Tomishige, Keiichi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5841-debe2e025efe72a8652a127ac17d5fb5a22d19e4b769a02d4f9c02419c895a623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Adsorption</topic><topic>carboxylic acids</topic><topic>Catalysis</topic><topic>enantioselectivity</topic><topic>Hydrogenation</topic><topic>Kinetics</topic><topic>Lactic Acid - chemistry</topic><topic>molybdenum</topic><topic>Molybdenum - chemistry</topic><topic>Oxides - chemistry</topic><topic>Propylene Glycol - chemistry</topic><topic>ruthenium</topic><topic>Ruthenium - chemistry</topic><topic>Spectrum analysis</topic><topic>X-rays</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Takeda, Yasuyuki</creatorcontrib><creatorcontrib>Shoji, Tomohiro</creatorcontrib><creatorcontrib>Watanabe, Hideo</creatorcontrib><creatorcontrib>Tamura, Masazumi</creatorcontrib><creatorcontrib>Nakagawa, Yoshinao</creatorcontrib><creatorcontrib>Okumura, Kazu</creatorcontrib><creatorcontrib>Tomishige, Keiichi</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Takeda, Yasuyuki</au><au>Shoji, Tomohiro</au><au>Watanabe, Hideo</au><au>Tamura, Masazumi</au><au>Nakagawa, Yoshinao</au><au>Okumura, Kazu</au><au>Tomishige, Keiichi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Hydrogenation of Lactic Acid to 1,2-Propanediol over Highly Active Ruthenium-Molybdenum Oxide Catalysts</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2015-04-13</date><risdate>2015</risdate><volume>8</volume><issue>7</issue><spage>1170</spage><epage>1178</epage><pages>1170-1178</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>Modification of Ru/C with a small amount of MoOx (RuMoOx/C) enhanced the catalytic activity in the hydrogenation of L‐lactic acid to form 1,2‐propanediol and maintained high selectivity. The turnover frequency based on the amount of Ru over the optimized RuMoOx/C catalyst (Mo/Ru molar ratio=1:16) was 114 h−1 at 393 K, which was about 4 times higher than that over Ru/C. The same effect of MoOx was obtained over RuMoOx/SiO2, although RuMoOx/SiO2 showed slightly lower activity than that of RuMoOx/C. RuMoOx/C achieved a high yield of 95 % in 18 h at 393 K and was applicable to various carboxylic acids to provide the corresponding alcohols in high yields. Modification with MoOx also brought about suppression of racemization and (S)‐1,2‐propanediol was obtained in high enantiomeric excess at 353 K. Based on kinetic analysis and characterization data, such as XRD, TEM, CO adsorption by a volumetric method, FTIR spectroscopy, and X‐ray absorption spectroscopy, for RuMoOx/C and RuMoOx/SiO2, the catalyst structure and reaction mechanism are proposed.
Minor adjustment for major effects: Modification of supported ruthenium catalysts with a small amount of molybdenum oxide (RuMoOx/C, RuMoOx/SiO2) enhances the catalytic activity for the hydrogenation of L‐lactic acid to give (S)‐1,2‐propanediol with high selectivity. The turnover frequency is roughly four times higher than over Ru/C. The results reported are encouraging for the design of selective hydrogenation catalysts and the development of synthesis methods of alcohols.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25510671</pmid><doi>10.1002/cssc.201403011</doi><tpages>9</tpages></addata></record> |
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| subjects | Adsorption carboxylic acids Catalysis enantioselectivity Hydrogenation Kinetics Lactic Acid - chemistry molybdenum Molybdenum - chemistry Oxides - chemistry Propylene Glycol - chemistry ruthenium Ruthenium - chemistry Spectrum analysis X-rays |
| title | Selective Hydrogenation of Lactic Acid to 1,2-Propanediol over Highly Active Ruthenium-Molybdenum Oxide Catalysts |
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