10 Progress in the Selective Semi-hydrogenation of Alkynes …
335
13. Liu L, Corma A (2018) Metal catalysts for heterogeneous catalysis: from single atoms to
nanoclusters and nanoparticles. Chem Rev 118(10):4981–5079. https://doi.org/10.1021/acs.
chemrev.7b00776
14. Huang X, Xia Y, Cao Y, Zheng X, Pan H, Zhu J, Ma C, Wang H, Li J, You R, Wei S, Huang
W, Lu J (2017) Enhancing both selectivity and coking-resistance of a single-atom Pd1/C3N4
catalyst for acetylene hydrogenation. Nano Res 10(4):1302–1312. https://doi.org/10.1007/
s12274-016-1416-z
15. Delgado JA, Benkirane O, Claver C, Curulla-Ferre D, Godard C (2017) Advances in the
preparation of highly selective nanocatalysts for the semi-hydrogenation of alkynes using
colloidal approaches. Dalton Trans 46(37):12381–12403. https://doi.org/10.1039/C7DT01
607G
16. Liu Y, Hu L, Chen H, Du H (2015) An alkene-promoted borane-catalyzed highly stereoselective hydrogenation of alkynes to Give Z- and E-alkenes. Chem Eur J 21(8):3495–3501.
https://doi.org/10.1002/chem.201405388
17. Alonso F, Osante I, Yus M (2007) Highly selective hydrogenation of multiple carbon–carbon
bonds promoted by nickel(0) nanoparticles. Tetrahedron 63(1):93–102. https://doi.org/10.
1016/j.tet.2006.10.043
18. Huang B, Wang T, Yang Z, Qian W, Long J, Zeng G, Lei C (2017) Iron-based bimetallic
nanocatalysts for highly selective hydrogenation of acetylene in N,N-dimethylformamide at
room temperature. ACS Sustain Chem Eng 5(2):1668–1674. https://doi.org/10.1021/acssus
chemeng.6b02413
19. Liang S, Hammond GB, Xu B (2016) Supported gold nanoparticles catalyzed cis-selective
semihydrogenation of alkynes using ammonium formate as the reductant. Chem Commun
52(35):6013–6016. https://doi.org/10.1039/C6CC01318J
20. Slack ED, Gabriel CM, Lipshutz BH (2014) A palladium nanoparticle-nanomicelle combination for the stereoselective semihydrogenation of alkynes in water at room temperature.
Angew Chem Int Ed 53(51):14051–14054. https://doi.org/10.1002/anie.201407723
21. Zhong J-J, Liu Q, Wu C-J, Meng Q-Y, Gao X-W, Li Z-J, Chen B, Tung C-H, Wu L-Z (2016)
Combining visible light catalysis and transfer hydrogenation for in situ efficient and selective
semihydrogenation of alkynes under ambient conditions. Chem Commun 52(9):1800–1803.
https://doi.org/10.1039/C5CC08697C
22. Lian J, Chai Y, Qi Y, Guo X, Guan N, Li L, Zhang F (2020) Unexpectedly selective hydrogenation of phenylacetylene to styrene on titania supported platinum photocatalyst under 385 nm
monochromatic light irradiation. Chin J Catal 41(4):598–603. https://doi.org/10.1016/S18722067(19)63453-4
23. Duca D, Arena F, Parmaliana A, Deganello G (1998) Hydrogenation of acetylene in ethylene
rich feedstocks: comparison between palladium catalysts supported on pumice and alumina.
App Catal A Gen 172(2):207–216. https://doi.org/10.1016/S0926-860X(98)00123-9
24. Osswald J, Giedigkeit R, Jentoft RE, Armbrüster M, Girgsdies F, Kovnir K, Ressler T, Grin Y,
Schlögl R (2008) Palladium–gallium intermetallic compounds for the selective hydrogenation
of acetylene: part I: preparation and structural investigation under reaction conditions. J Catal
258(1):210–218. https://doi.org/10.1016/j.jcat.2008.06.013
25. Yarulin AE, Crespo-Quesada RM, Egorova EV, Kiwi-Minsker LL (2012) Structure sensitivity of selective acetylene hydrogenation over the catalysts with shape-controlled palladium
nanoparticles. Kinet Catal 53(2):253–261. https://doi.org/10.1134/s0023158412020152
26. Zhang Y, Diao W, Monnier JR, Williams CT (2015) Pd-Ag/SiO 2 bimetallic catalysts prepared
by galvanic displacement for selective hydrogenation of acetylene in excess ethylene. Catal
Sci Technol 5(8):4123–4132. https://doi.org/10.1039/c5cy00353a
27. Börger L, Cölfen H (1999) Prog Colloid Polym Sci 113:23
28. Molnár Á, Sárkány A, Varga M (2001) Hydrogenation of carbon–carbon multiple bonds:
chemo-, regio- and stereo-selectivity. J Mol Catal A Chem 173(1–2):185–221. https://doi.
org/10.1016/S1381-1169(01)00150-9
29. Bond GC (1962) Catalysis by metals. Academic Press, New York
335
13. Liu L, Corma A (2018) Metal catalysts for heterogeneous catalysis: from single atoms to
nanoclusters and nanoparticles. Chem Rev 118(10):4981–5079. https://doi.org/10.1021/acs.
chemrev.7b00776
14. Huang X, Xia Y, Cao Y, Zheng X, Pan H, Zhu J, Ma C, Wang H, Li J, You R, Wei S, Huang
W, Lu J (2017) Enhancing both selectivity and coking-resistance of a single-atom Pd1/C3N4
catalyst for acetylene hydrogenation. Nano Res 10(4):1302–1312. https://doi.org/10.1007/
s12274-016-1416-z
15. Delgado JA, Benkirane O, Claver C, Curulla-Ferre D, Godard C (2017) Advances in the
preparation of highly selective nanocatalysts for the semi-hydrogenation of alkynes using
colloidal approaches. Dalton Trans 46(37):12381–12403. https://doi.org/10.1039/C7DT01
607G
16. Liu Y, Hu L, Chen H, Du H (2015) An alkene-promoted borane-catalyzed highly stereoselective hydrogenation of alkynes to Give Z- and E-alkenes. Chem Eur J 21(8):3495–3501.
https://doi.org/10.1002/chem.201405388
17. Alonso F, Osante I, Yus M (2007) Highly selective hydrogenation of multiple carbon–carbon
bonds promoted by nickel(0) nanoparticles. Tetrahedron 63(1):93–102. https://doi.org/10.
1016/j.tet.2006.10.043
18. Huang B, Wang T, Yang Z, Qian W, Long J, Zeng G, Lei C (2017) Iron-based bimetallic
nanocatalysts for highly selective hydrogenation of acetylene in N,N-dimethylformamide at
room temperature. ACS Sustain Chem Eng 5(2):1668–1674. https://doi.org/10.1021/acssus
chemeng.6b02413
19. Liang S, Hammond GB, Xu B (2016) Supported gold nanoparticles catalyzed cis-selective
semihydrogenation of alkynes using ammonium formate as the reductant. Chem Commun
52(35):6013–6016. https://doi.org/10.1039/C6CC01318J
20. Slack ED, Gabriel CM, Lipshutz BH (2014) A palladium nanoparticle-nanomicelle combination for the stereoselective semihydrogenation of alkynes in water at room temperature.
Angew Chem Int Ed 53(51):14051–14054. https://doi.org/10.1002/anie.201407723
21. Zhong J-J, Liu Q, Wu C-J, Meng Q-Y, Gao X-W, Li Z-J, Chen B, Tung C-H, Wu L-Z (2016)
Combining visible light catalysis and transfer hydrogenation for in situ efficient and selective
semihydrogenation of alkynes under ambient conditions. Chem Commun 52(9):1800–1803.
https://doi.org/10.1039/C5CC08697C
22. Lian J, Chai Y, Qi Y, Guo X, Guan N, Li L, Zhang F (2020) Unexpectedly selective hydrogenation of phenylacetylene to styrene on titania supported platinum photocatalyst under 385 nm
monochromatic light irradiation. Chin J Catal 41(4):598–603. https://doi.org/10.1016/S18722067(19)63453-4
23. Duca D, Arena F, Parmaliana A, Deganello G (1998) Hydrogenation of acetylene in ethylene
rich feedstocks: comparison between palladium catalysts supported on pumice and alumina.
App Catal A Gen 172(2):207–216. https://doi.org/10.1016/S0926-860X(98)00123-9
24. Osswald J, Giedigkeit R, Jentoft RE, Armbrüster M, Girgsdies F, Kovnir K, Ressler T, Grin Y,
Schlögl R (2008) Palladium–gallium intermetallic compounds for the selective hydrogenation
of acetylene: part I: preparation and structural investigation under reaction conditions. J Catal
258(1):210–218. https://doi.org/10.1016/j.jcat.2008.06.013
25. Yarulin AE, Crespo-Quesada RM, Egorova EV, Kiwi-Minsker LL (2012) Structure sensitivity of selective acetylene hydrogenation over the catalysts with shape-controlled palladium
nanoparticles. Kinet Catal 53(2):253–261. https://doi.org/10.1134/s0023158412020152
26. Zhang Y, Diao W, Monnier JR, Williams CT (2015) Pd-Ag/SiO 2 bimetallic catalysts prepared
by galvanic displacement for selective hydrogenation of acetylene in excess ethylene. Catal
Sci Technol 5(8):4123–4132. https://doi.org/10.1039/c5cy00353a
27. Börger L, Cölfen H (1999) Prog Colloid Polym Sci 113:23
28. Molnár Á, Sárkány A, Varga M (2001) Hydrogenation of carbon–carbon multiple bonds:
chemo-, regio- and stereo-selectivity. J Mol Catal A Chem 173(1–2):185–221. https://doi.
org/10.1016/S1381-1169(01)00150-9
29. Bond GC (1962) Catalysis by metals. Academic Press, New York