342
J. A. Delgado and C. Godard
128. Vilé G, Almora-Barrios N, Mitchell S, López N, Pérez-Ramírez J (2014) From the Lindlar
catalyst to supported ligand-modified palladium nanoparticles: selectivity patterns and
accessibility constraints in the continuous-flow three-phase hydrogenation of acetylenic
compounds. Chem Eur J 20(20):5926–5937. https://doi.org/10.1002/chem.201304795
129. Albani D, Vile G, Mitchell S, Witte PT, Almora-Barrios N, Verel R, Lopez N, Perez-Ramirez
J (2016) Ligand ordering determines the catalytic response of hybrid palladium nanoparticles
in hydrogenation. Catal Sci Technol 6(6):1621–1631. https://doi.org/10.1039/C5CY01921D
130. La Sorella G, Sperni L, Canton P, Coletti L, Fabris F, Strukul G, Scarso A (2018) Selective
hydrogenations and dechlorinations in water mediated by anionic surfactant-stabilized Pd
nanoparticles. J Org Chem 83(14):7438–7446. https://doi.org/10.1021/acs.joc.8b00314
131. Zhang H, Yang Y, Dai W, Yang D, Lu S, Ji Y (2012) An aqueous-phase catalytic process
for the selective hydrogenation of acetylene with monodisperse water soluble palladium
nanoparticles as catalyst. Catal Sci Technol 2(7):1319–1323. https://doi.org/10.1039/c2cy20
179h
132. Crespo-Quesada M, Andanson J-M, Yarulin A, Lim B, Xia Y, Kiwi-Minsker L (2011) UV–
ozone cleaning of supported poly(vinylpyrrolidone)-stabilized palladium nanocubes: effect
of stabilizer removal on morphology and catalytic behavior. Langmuir 27(12):7909–7916.
https://doi.org/10.1021/la201007m
133. Borodzi´ nski A, Bond GC (2006) Selective hydrogenation of ethyne in ethene-rich streams
on palladium catalysts. Part 1. Effect of changes to the catalyst during reaction. Catal Rev
48(2):91–144. https://doi.org/10.1080/01614940500364909
134. García-Mota M, Bridier B, Pérez-Ramírez J, López N (2010) Interplay between carbon
monoxide, hydrides, and carbides in selective alkyne hydrogenation on palladium. J Catal
273(2):92–102. https://doi.org/10.1016/j.jcat.2010.04.018
135. Studt F, Abild-Pedersen F, Bligaard T, Sørensen RZ, Christensen CH, Nørskov JK (2008)
On the role of surface modifications of palladium catalysts in the selective hydrogenation of
acetylene. Angew Chem Int Ed 47(48):9299–9302. https://doi.org/10.1002/anie.200802844
136. Delannay F (1984) Characterization of heterogeneous catalysts
137. Bae W, Mehra RK (1998) J Inorg Biochem 70:125
138. Brown CA, Ahuja VK (1973) Catalytic hydrogenation. VI. Reaction of sodium borohydride
with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure. J Organ Chem 38(12):2226–2230.
https://doi.org/10.1021/jo00952a024
139. Brown CA, Ahuja VK (1973) “P-2 nickel” catalyst with ethylenediamine, a novel system
for highly stereospecific reduction of alkynes to cis-olefins. J Chem Soc Chem Commun
15:553–554. https://doi.org/10.1039/c39730000553
140. Kwon SG, Krylova G, Sumer A, Schwartz MM, Bunel EE, Marshall CL, Chattopadhyay
S, Lee B, Jellinek J, Shevchenko EV (2012) Capping ligands as selectivity switchers in
hydrogenation reactions. Nano Lett 12(10):5382–5388. https://doi.org/10.1021/nl3027636
141. Shevchenko EV, Talapin DV, Rogach AL, Kornowski A, Haase M, Weller H (2002) Colloidal
synthesis and self-assembly of CoPt 3 nanocrystals. J Am Chem Soc 124(38):11480–11485.
https://doi.org/10.1021/ja025976l
142. Fiorio JL, Lopez N, Rossi LM (2017) Gold-ligand catalyzed selective hydrogenation of
alkynes into cis-alkenes via H 2 heterolytic activation by frustrated Lewis pairs. ACS Catal.
https://doi.org/10.1021/acscatal.6b03441
143. Nikoshvili LZ, Bykov AV, Khudyakova TE, LaGrange T, Heroguel F, Luterbacher JS,
Matveeva VG, Sulman EM, Dyson PJ, Kiwi-Minsker L (2017) Promotion effect of alkali
metal hydroxides on polymer-stabilized pd nanoparticles for selective hydrogenation of C–C
triple bonds in alkynols. Ind Eng Chem Res 56(45):13219–13227. https://doi.org/10.1021/
acs.iecr.7b01612
144. Borodzi´ nski A, Bond GC (2008) Selective Hydrogenation of ethyne in ethene-rich streams on
palladium catalysts, part 2: steady-state kinetics and effects of palladium particle size, carbon
monoxide, and promoters. Catal Rev 50(3):379–469. https://doi.org/10.1080/016149408021
42102
J. A. Delgado and C. Godard
128. Vilé G, Almora-Barrios N, Mitchell S, López N, Pérez-Ramírez J (2014) From the Lindlar
catalyst to supported ligand-modified palladium nanoparticles: selectivity patterns and
accessibility constraints in the continuous-flow three-phase hydrogenation of acetylenic
compounds. Chem Eur J 20(20):5926–5937. https://doi.org/10.1002/chem.201304795
129. Albani D, Vile G, Mitchell S, Witte PT, Almora-Barrios N, Verel R, Lopez N, Perez-Ramirez
J (2016) Ligand ordering determines the catalytic response of hybrid palladium nanoparticles
in hydrogenation. Catal Sci Technol 6(6):1621–1631. https://doi.org/10.1039/C5CY01921D
130. La Sorella G, Sperni L, Canton P, Coletti L, Fabris F, Strukul G, Scarso A (2018) Selective
hydrogenations and dechlorinations in water mediated by anionic surfactant-stabilized Pd
nanoparticles. J Org Chem 83(14):7438–7446. https://doi.org/10.1021/acs.joc.8b00314
131. Zhang H, Yang Y, Dai W, Yang D, Lu S, Ji Y (2012) An aqueous-phase catalytic process
for the selective hydrogenation of acetylene with monodisperse water soluble palladium
nanoparticles as catalyst. Catal Sci Technol 2(7):1319–1323. https://doi.org/10.1039/c2cy20
179h
132. Crespo-Quesada M, Andanson J-M, Yarulin A, Lim B, Xia Y, Kiwi-Minsker L (2011) UV–
ozone cleaning of supported poly(vinylpyrrolidone)-stabilized palladium nanocubes: effect
of stabilizer removal on morphology and catalytic behavior. Langmuir 27(12):7909–7916.
https://doi.org/10.1021/la201007m
133. Borodzi´ nski A, Bond GC (2006) Selective hydrogenation of ethyne in ethene-rich streams
on palladium catalysts. Part 1. Effect of changes to the catalyst during reaction. Catal Rev
48(2):91–144. https://doi.org/10.1080/01614940500364909
134. García-Mota M, Bridier B, Pérez-Ramírez J, López N (2010) Interplay between carbon
monoxide, hydrides, and carbides in selective alkyne hydrogenation on palladium. J Catal
273(2):92–102. https://doi.org/10.1016/j.jcat.2010.04.018
135. Studt F, Abild-Pedersen F, Bligaard T, Sørensen RZ, Christensen CH, Nørskov JK (2008)
On the role of surface modifications of palladium catalysts in the selective hydrogenation of
acetylene. Angew Chem Int Ed 47(48):9299–9302. https://doi.org/10.1002/anie.200802844
136. Delannay F (1984) Characterization of heterogeneous catalysts
137. Bae W, Mehra RK (1998) J Inorg Biochem 70:125
138. Brown CA, Ahuja VK (1973) Catalytic hydrogenation. VI. Reaction of sodium borohydride
with nickel salts in ethanol solution. P-2 Nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure. J Organ Chem 38(12):2226–2230.
https://doi.org/10.1021/jo00952a024
139. Brown CA, Ahuja VK (1973) “P-2 nickel” catalyst with ethylenediamine, a novel system
for highly stereospecific reduction of alkynes to cis-olefins. J Chem Soc Chem Commun
15:553–554. https://doi.org/10.1039/c39730000553
140. Kwon SG, Krylova G, Sumer A, Schwartz MM, Bunel EE, Marshall CL, Chattopadhyay
S, Lee B, Jellinek J, Shevchenko EV (2012) Capping ligands as selectivity switchers in
hydrogenation reactions. Nano Lett 12(10):5382–5388. https://doi.org/10.1021/nl3027636
141. Shevchenko EV, Talapin DV, Rogach AL, Kornowski A, Haase M, Weller H (2002) Colloidal
synthesis and self-assembly of CoPt 3 nanocrystals. J Am Chem Soc 124(38):11480–11485.
https://doi.org/10.1021/ja025976l
142. Fiorio JL, Lopez N, Rossi LM (2017) Gold-ligand catalyzed selective hydrogenation of
alkynes into cis-alkenes via H 2 heterolytic activation by frustrated Lewis pairs. ACS Catal.
https://doi.org/10.1021/acscatal.6b03441
143. Nikoshvili LZ, Bykov AV, Khudyakova TE, LaGrange T, Heroguel F, Luterbacher JS,
Matveeva VG, Sulman EM, Dyson PJ, Kiwi-Minsker L (2017) Promotion effect of alkali
metal hydroxides on polymer-stabilized pd nanoparticles for selective hydrogenation of C–C
triple bonds in alkynols. Ind Eng Chem Res 56(45):13219–13227. https://doi.org/10.1021/
acs.iecr.7b01612
144. Borodzi´ nski A, Bond GC (2008) Selective Hydrogenation of ethyne in ethene-rich streams on
palladium catalysts, part 2: steady-state kinetics and effects of palladium particle size, carbon
monoxide, and promoters. Catal Rev 50(3):379–469. https://doi.org/10.1080/016149408021
42102