Heterogeneous Metal-Free Hydrogenation over Defect-Laden Hexagonal Boron Nitride
Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this process utilize metals as the active species. Until recently, catalytic heterogeneous hydrogenation over a metal-free solid was unknown; implementa...
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Published in | ACS omega Vol. 1; no. 6; pp. 1343 - 1354 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
31.12.2016
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Abstract | Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this process utilize metals as the active species. Until recently, catalytic heterogeneous hydrogenation over a metal-free solid was unknown; implementation of such a system would eliminate the health, environmental, and economic concerns associated with metal-based catalysts. Here, we report good hydrogenation rates and yields for a metal-free heterogeneous hydrogenation catalyst as well as its unique hydrogenation mechanism. Catalytic hydrogenation of olefins was achieved over defect-laden h-BN (dh-BN) in a reactor designed to maximize the defects in h-BN sheets. Good yields (>90%) and turnover frequencies (6 × 10–5–4 × 10–3) were obtained for the hydrogenation of propene, cyclohexene, 1,1-diphenylethene, (E)- and (Z)-1,2-diphenylethene, octadecene, and benzylideneacetophenone. Temperature-programmed desorption of ethene over processed h-BN indicates the formation of a highly defective structure. Solid-state NMR (SSNMR) measurements of dh-BN with high and low propene surface coverages show four different binding modes. The introduction of defects into h-BN creates regions of electronic deficiency and excess. Density functional theory calculations show that both the alkene and hydrogen-bond order are reduced over four specific defects: boron substitution for nitrogen (BN), vacancies (VB and VN), and Stone–Wales defects. SSNMR and binding-energy calculations show that VN are most likely the catalytically active sites. This work shows that catalytic sites can be introduced into a material previously thought to be catalytically inactive through the production of defects. |
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AbstractList | Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this process utilize metals as the active species. Until recently, catalytic heterogeneous hydrogenation over a metal-free solid was unknown; implementation of such a system would eliminate the health, environmental, and economic concerns associated with metal-based catalysts. Here, we report good hydrogenation rates and yields for a metal-free heterogeneous hydrogenation catalyst as well as its unique hydrogenation mechanism. Catalytic hydrogenation of olefins was achieved over defect-laden h-BN (dh-BN) in a reactor designed to maximize the defects in h-BN sheets. Good yields (>90%) and turnover frequencies (6 × 10–5–4 × 10–3) were obtained for the hydrogenation of propene, cyclohexene, 1,1-diphenylethene, (E)- and (Z)-1,2-diphenylethene, octadecene, and benzylideneacetophenone. Temperature-programmed desorption of ethene over processed h-BN indicates the formation of a highly defective structure. Solid-state NMR (SSNMR) measurements of dh-BN with high and low propene surface coverages show four different binding modes. The introduction of defects into h-BN creates regions of electronic deficiency and excess. Density functional theory calculations show that both the alkene and hydrogen-bond order are reduced over four specific defects: boron substitution for nitrogen (BN), vacancies (VB and VN), and Stone–Wales defects. SSNMR and binding-energy calculations show that VN are most likely the catalytically active sites. This work shows that catalytic sites can be introduced into a material previously thought to be catalytically inactive through the production of defects. Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this process utilize metals as the active species. Until recently, catalytic heterogeneous hydrogenation over a metal-free solid was unknown; implementation of such a system would eliminate the health, environmental, and economic concerns associated with metal-based catalysts. Here, we report good hydrogenation rates and yields for a metal-free heterogeneous hydrogenation catalyst as well as its unique hydrogenation mechanism. Catalytic hydrogenation of olefins was achieved over defect-laden h- BN ( dh -BN) in a reactor designed to maximize the defects in h- BN sheets. Good yields (>90%) and turnover frequencies (6 × 10 –5 –4 × 10 –3 ) were obtained for the hydrogenation of propene, cyclohexene, 1,1-diphenylethene, ( E )- and ( Z )-1,2-diphenylethene, octadecene, and benzylideneacetophenone. Temperature-programmed desorption of ethene over processed h -BN indicates the formation of a highly defective structure. Solid-state NMR (SSNMR) measurements of dh -BN with high and low propene surface coverages show four different binding modes. The introduction of defects into h- BN creates regions of electronic deficiency and excess. Density functional theory calculations show that both the alkene and hydrogen-bond order are reduced over four specific defects: boron substitution for nitrogen (B N ), vacancies (V B and V N ), and Stone–Wales defects. SSNMR and binding-energy calculations show that V N are most likely the catalytically active sites. This work shows that catalytic sites can be introduced into a material previously thought to be catalytically inactive through the production of defects. Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this process utilize metals as the active species. Until recently, catalytic heterogeneous hydrogenation over a metal-free solid was unknown; implementation of such a system would eliminate the health, environmental, and economic concerns associated with metal-based catalysts. Here, we report good hydrogenation rates and yields for a metal-free heterogeneous hydrogenation catalyst as well as its unique hydrogenation mechanism. Catalytic hydrogenation of olefins was achieved over defect-laden BN ( -BN) in a reactor designed to maximize the defects in BN sheets. Good yields (>90%) and turnover frequencies (6 × 10 -4 × 10 ) were obtained for the hydrogenation of propene, cyclohexene, 1,1-diphenylethene, ( )- and ( )-1,2-diphenylethene, octadecene, and benzylideneacetophenone. Temperature-programmed desorption of ethene over processed -BN indicates the formation of a highly defective structure. Solid-state NMR (SSNMR) measurements of -BN with high and low propene surface coverages show four different binding modes. The introduction of defects into BN creates regions of electronic deficiency and excess. Density functional theory calculations show that both the alkene and hydrogen-bond order are reduced over four specific defects: boron substitution for nitrogen (B ), vacancies (V and V ), and Stone-Wales defects. SSNMR and binding-energy calculations show that V are most likely the catalytically active sites. This work shows that catalytic sites can be introduced into a material previously thought to be catalytically inactive through the production of defects. Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this process utilize metals as the active species. Until recently, catalytic heterogeneous hydrogenation over a metal-free solid was unknown; implementation of such a system would eliminate the health, environmental, and economic concerns associated with metal-based catalysts. We report good hydrogenation rates and yields for a metal-free heterogeneous hydrogenation catalyst as well as its unique hydrogenation mechanism. We achieved catalytic hydrogenation of olefins over defect-laden h-BN (dh-BN) in a reactor designed to maximize the defects in h-BN sheets. Good yields (>90%) and turnover frequencies (6 × 10–5–4 × 10–3) were obtained for the hydrogenation of propene, cyclohexene, 1,1-diphenylethene, (E)- and (Z)-1,2-diphenylethene, octadecene, and benzylideneacetophenone. Temperature-programmed desorption of ethene over processed h-BN indicates the formation of a highly defective structure. Solid-state NMR (SSNMR) measurements of dh-BN with high and low propene surface coverages show four different binding modes. The introduction of defects into h-BN creates regions of electronic deficiency and excess. Density functional theory calculations show that both the alkene and hydrogen-bond order are reduced over four specific defects: boron substitution for nitrogen (BN), vacancies (VB and VN), and Stone–Wales defects. SSNMR and binding-energy calculations show that VN are most likely the catalytically active sites. Our work shows that catalytic sites can be introduced into a material previously thought to be catalytically inactive through the production of defects. |
Author | Penabade, Rachel A Le, Duy Blair, Richard G Nash, David J Giesler, Kyle E Farha, Omar K Parra, Natalia S Aminpour, Maral Li, Zhanyong Harper, James K Restrepo, David T Rahman, Talat S |
AuthorAffiliation | Department of Chemistry Cluster for the Rational Design of Catalysts for Energy Applications and Propulsion Center for Advanced Turbomachinery and Energy Research Department of Chemistry, International Institute for Nanotechnology Northwestern University University of Central Florida Department of Physics |
AuthorAffiliation_xml | – name: – name: Department of Chemistry – name: University of Central Florida – name: Department of Physics – name: Department of Chemistry, International Institute for Nanotechnology – name: Northwestern University – name: Cluster for the Rational Design of Catalysts for Energy Applications and Propulsion – name: Center for Advanced Turbomachinery and Energy Research |
Author_xml | – sequence: 1 givenname: David J surname: Nash fullname: Nash, David J – sequence: 2 givenname: David T surname: Restrepo fullname: Restrepo, David T – sequence: 3 givenname: Natalia S surname: Parra fullname: Parra, Natalia S – sequence: 4 givenname: Kyle E surname: Giesler fullname: Giesler, Kyle E – sequence: 5 givenname: Rachel A surname: Penabade fullname: Penabade, Rachel A – sequence: 6 givenname: Maral surname: Aminpour fullname: Aminpour, Maral – sequence: 7 givenname: Duy surname: Le fullname: Le, Duy – sequence: 8 givenname: Zhanyong orcidid: 0000-0002-3230-5955 surname: Li fullname: Li, Zhanyong – sequence: 9 givenname: Omar K orcidid: 0000-0002-9904-9845 surname: Farha fullname: Farha, Omar K – sequence: 10 givenname: James K surname: Harper fullname: Harper, James K – sequence: 11 givenname: Talat S surname: Rahman fullname: Rahman, Talat S – sequence: 12 givenname: Richard G orcidid: 0000-0002-8208-9787 surname: Blair fullname: Blair, Richard G email: Richard.Blair@ucf.edu |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31457200$$D View this record in MEDLINE/PubMed https://www.osti.gov/biblio/1336965$$D View this record in Osti.gov |
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Snippet | Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this... Catalytic hydrogenation is an important process used for the production of everything from foods to fuels. Current heterogeneous implementations of this... |
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SubjectTerms | Catalysts Hydrogenation INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Organic compounds and Functional groups Quantum mechanical methods |
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Title | Heterogeneous Metal-Free Hydrogenation over Defect-Laden Hexagonal Boron Nitride |
URI | http://dx.doi.org/10.1021/acsomega.6b00315 https://www.ncbi.nlm.nih.gov/pubmed/31457200 https://search.proquest.com/docview/2281851619 https://www.osti.gov/biblio/1336965 https://pubmed.ncbi.nlm.nih.gov/PMC6640807 https://doaj.org/article/e4f19122d8fa4201a8848c5288e84f36 |
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