SUPPLEMENTARY INFORMATION. New multicomponent catalysts for the selective aerobic oxidative. condensation of benzylamines to N-benzylidenbenzylamine
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1 Eletroni Supplementry Mteril (ESI) for Ctlysis Siene & Tehnology. This journl is The Royl Soiety of Chemistry 2014 SUPPLEMENTARY INFORMATION New multiomponent tlysts for the seletive eroi oxidtive ondenstion of enzylmines to N-enzylidenenzylmine Cristin Mdlin Opris, Otvin Pvel, Alin Morgues, Jml El Hskouri,, Dniel Beltrán, Pedro Amorós, * M. Dolores Mros, d Lur Elen Stofle, e Vsile I. Prvulesu * University of Buhrest, Deprtment of Orgni Chemistry nd Ctlysis, Bdul Regin Eliset 4-12, Buhrest, Romni, vsile.prvulesu@g.uniu.ro Institut de Cieni dels Mteril, Universitt de Vleni, P. O. Box 22085, Vleni E46071, Spin, pedro.moros@uv.es Fundió Generl, Universitt de Vlèni. P. O. Box 22085, Vleni, Spin d Centro de Reonoimiento Moleulr y Desrrollo Tenológio (IDM), Deprtmento de Quími, Universidd Politéni de Vleni, Cmino de Ver s/n, Vleni, Spin e Ntionl Institute of Mterils Physis, PO Box MG-07, Buhrest-Mgurele, Romni Ctlysts hrteriztion Figures S1 nd S2 show the high-ngle XRD ptterns of ll synthesized UVM-7-sed mterils, fter nd efore the gold inorportion nd thermlly proessed t 200 nd 500ºC. Figures S3 nd S4 orrespond to TEM imges nd N 2 dsorption-desorption isotherms of the goldfree support/tlysts. The nikel inlusion does not ffet the mesostruture when ompred with TEM imge of UVM-7 pure sili. The two pore systems (intrprtile surftnt generted mesopore system nd the interprtile disordered lrge pores) result lerly ppreited. The Ce nd Sn inlusion lthough does not ffet in qulittive wy the originl mesostruture, the inorportion of these heteroelements fvors ertin interprtile ondenstion with the susequent reltively loss of texturl-type porosity.
2 Cristin Mdlin Opris, Otvin Pvel, Alin Morgues, Jml El Hskouri,, Dniel Beltrán, Pedro Amorós, * M. Dolores Mros, d Lur Elen Stofle, e Vsile I. Prvulesu * University of Buhrest, Deprtment of Orgni Chemistry nd Ctlysis, Bdul Regin Eliset 4-12, Buhrest, Romni, vsile.prvulesu@g.uniu.ro Institut de Cieni dels Mteril, Universitt de Vleni, P. O. Box 22085, Vleni E46071, Spin, pedro.moros@uv.es Fundió Generl, Universitt de Vlèni. P. O. Box 22085, Vleni, Spin d Centro de Reonoimiento Moleulr y Desrrollo Tenológio (IDM), Deprtmento de Quími, Universidd Politéni de Vleni, Cmino de Ver s/n, Vleni, Spin e Ntionl Institute of Mterils Physis, PO Box MG-07, Buhrest-Mgurele, Romni Ctlysts hrteriztion Fig. SI1. Low-ngle XRD ptterns of the gold-free supports. () Ni60, () Ni30, () Ni10, (d) Ce 60, (e) Ce 30, (f) Ce 10, (g) Sn 60, (h) Sn 30 nd (i) Sn 10.
3 Figures SI2 nd SI3 show the high-ngle XRD ptterns of ll synthesized UVM-7-sed mterils, fter nd efore the gold inorportion nd thermlly proessed t 200 nd 500ºC. Figures SI4 nd SI5 orrespond to TEM imges nd N 2 dsorption-desorption isotherms of the goldfree support/tlysts. The nikel inlusion does not ffet the mesostruture when ompred with TEM imge of UVM-7 pure sili. The two pore systems (intrprtile surftnt generted mesopore system nd the interprtile disordered lrge pores) result lerly ppreited. The Ce nd Sn inlusion lthough does not ffet in qulittive wy the originl mesostruture, the inorportion of these heteroelements fvors ertin interprtile ondenstion with the susequent reltively loss of texturl-type porosity. Figs. SI5 nd SI6 present N 2 dsorption desorption isotherms of tlysts : SI5 () Au/Sn 10 -UVM- 7, () Au/Sn 30 nd () Au/Sn 60, proessed t (i) 200ºC nd (ii) 500ºC. SI6 () Au/Ce 10, () Au/Ce 30 nd () Au/Ce 60, proessed t (i) 200ºC nd (ii) 500ºC Figs. SI7 nd SI8 present the BJH pore size distriutions from the dsorption rnhes of the N 2 dsorption-desorption isotherms of tlysts: SI7 () Au/Ce 10, () Au/Ce 30 nd () Au/Ce 60, proessed t (i) 200ºC nd (ii) 500ºC. SI8. () Au/Sn 10, () Au/Sn 30 nd () Au/Sn 60, proessed t (i) 200ºC nd (ii) 500ºC. Figs. SI9 nd SI10 present onversion results in reyling experiments
4 Ce 10 Ce 30 Ce 60 Au/Ce 10 (200) Au/Ce 30 (200) Au/Ce 60 (200) Au/Ce 10 (500) Au/Ce 30 (500) Au/Ce 60 (500) Intensity (.u.) SiO 2 (111) (200) (220) (311) (222) (400) (331) (420) thet (degrees) Fig. SI2. High-ngle XRD ptterns of the supports nd finl tlysts ontining Ce. Intensity (.u.) Sn 10 Sn 30 Sn 60 Au/Sn 10 (200) Au/Sn 30 (200) Au/Sn 60 (200) Au/Sn 10 (500) Au/Sn 30 (500) Au/Sn 60 (500) SiO 2 SnO 2 (110) SnO 2 (101) SnO 2 (111) SnO 2 (211) thet (degrees) Fig. SI3. High-ngle XRD ptterns of the supports nd finl tlysts ontining Sn.
5 Fig. SI4. Representtive TEM imge of Ni x smples (x=10). Fig. SI5. N 2 dsorption desorption isotherms of tlysts () Au/Sn 10, () Au/Sn 30 - UVM-7 nd () Au/Sn 60, proessed t (i) 200ºC nd (ii) 500ºC.
6 Fig. SI6. Representtive N 2 dsorption-desorption isotherms of the gold-free supports. () Ni 60, () Ce 60 - UVM-7 nd () Sn (i) 3.0 (i) dv/dlog(d) Pore Volume (m³/g Å) dv/dlog(d) Pore Volume (m³/g Å) Pore Dimeter (nm) Pore Dimeter (nm)
7 Fig. SI7. BJH pore size distriutions from the dsorption rnhes of the N 2 dsorption-desorption isotherms of tlysts () Au/Ce 10, () Au/Ce 30 nd () Au/Ce 60, proessed t (i) 200ºC nd (ii) 500ºC. dv/dlog(d) Pore Volume (m³/g Å) (i) Pore Dimeter (nm) dv/dlog(d) Pore Volume (m³/g Å) (ii) Pore Dimeter (nm) Fig. SI8. BJH pore size distriutions from the dsorption rnhes of the N 2 dsorption desorption isotherms of tlysts () Au/Sn 10, () Au/Sn 30 nd () Au/Sn 60, proessed t (i) 200ºC nd (ii) 500ºC. Conversion (%) Cyle
8 Conversion (%) Cyle Fig. SI9. Conversion of enzylmine on Au/Ce 60 (200) () nd Au/Ce 30 -UVM- 7(200) () tlysts over 10 suessive yles t 5 r O 2 (115 o C, 4h, seletivity 100%)..
9 50 Au/Ce60-Ni10(200) Au/Ce30-Ni10(200) Conversion (%) Cyle Fig. SI10. Conversion of enzylmine on Au/Ce 60 (200) nd Au/Ce 30 -UVM- 7(200) tlysts over 6 suessive yles t 2 r O 2 (115 o C, 4h, seletivity 100%).
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