Liquid-phase hydrogenation of benzaldehyde
2. Divakar D, Manikandan D, Kalidoss G, Sivakumar T (2008)
Catal Lett 125:277
Catalytic measurements
3. Han M, Zhang H, Du Y, Yang P, Deng Z (2011) React Kinet
Mech Catal 102:393
4. Clarke ML, Roff GJ (2007) In: de Vries JG, Elsevier CJ (eds) The
handbook of homogeneous hydrogenation. Wiley-VCH,
Weinheim
Pretreatment of the catalyst samples prior to catalytic ex-
periments included drying in argon at 423 K for 0.5 h and
reduction in flowing hydrogen at 523 K for 2 h.
Liquid-phase hydrogenation of benzaldehyde (98 %,
Acros Organics) in the presence of synthesized catalysts was
studied using a 180 cm3 steel autoclave. A 0.5-g catalyst
sample was placed in the autoclave with 30 cm3 of ethanol
(96 %). Air components were removed from the catalyst
pore space by pre-reduction with hydrogen at a temperature
of 353 K and a pressure of 0.5 MPa for 1 h. The reaction
mixture was heated to a specified temperature using the
circulation of heated water through the external jacket. To
stir the mixture, the autoclave was mounted on a shaker.
After pre-reduction, 5.0 cm3 of benzaldehyde and 65 cm3
of ethanol were loaded into the autoclave. The hydrogena-
tion was performed for 5 h at 313 and 333 K and a hydrogen
pressure of 0.5 MPa under vigorous stirring of the reaction
mixture, which excluded external diffusion limitations. The
reaction products were identified by GC–MS (Agilent
5973 N/6890 N). The quantitative determination of the re-
action products was carried out every hour by GC (Hewlett
Packard 5890 Series II) in a capillary column HP-PONA
(50 m 9 0.20 mm, Agilent Technologies) with linear
heating from 313 to 473 K during analysis.
´
5. Rosales M, Gonzalez A, Alvarado Y, Rubio R, Andriollo A,
´
Sanchez-Delgado RA (1992) J Mol Catal 75:1
6. Casey CP, Beetner SE, Johnson JB (2008) J Am Chem Soc
130:2285
7. Johnstone RAW, Wilby AH, Entwistle ID (1985) Chem Rev
85:129
8. Baidossi M, Joshi AV, Mukhopadhyay S, Sasson Y (2004) Synth
Commun 34:643
9. Gao Y, Jaenicke S, Chuah G-K (2014) Appl Catal A: Gen 484:51
ˇ
ˇ
´
´
´
´
´
´
10. Prochazkova D, Zamostny P, Bejblova M, Cerveny L, Cejka J
(2007) Appl Catal A: Gen 332:56
11. Pinna F, Menegazzo F, Signoretto M, Canton P, Fagherazzi G,
Pernicone N (2001) Appl Catal A: Gen 219:195
ˇ
12. Cerveny L, Belohlav Z, Hamed MNH (1996) Res Chem Intermed
´
ˇ
22:15
13. Song L, Li K, Li X, Wu P (2011) React Kinet Mech Catal 104:99
14. Ding Y, Li X, Pan H, Wu P (2014) Catal Lett 144:268
15. Song L, Li X, Wang H, Wu H, Wu P (2009) Catal Lett 133:63
16. Nijhuis TA, Kreutzer MT, Romijn ACJ, Kapteijn F, Moulijn JA
(2001) Catal Today 66:157
17. Liu W, Chen X, Yang J, Li Y, Zhou Y, Huang Z, Yi Z (2012)
Adv Mater Res 430–432:917
18. Saadi A, Merabti R, Rassoul Z, Bettahar MM (2006) J Mol Catal
A: Chem 253:79
19. Koopman PGJ (1980) Ruthenium hydrogenation catalysts. Delft
University Press, Delft
20. Zakumbaeva GD, Zakarina NA, Beketaeva LA, Naidin VA
(1982) Metallicheskie katalizatory (Metallic catalysts). Nauka,
Alma-Ata (in Russian)
Benzaldehyde conversion X (%) and benzyl alcohol
selectivity S (%) were determined as follows:
CB;0 ꢁ CB
21. Rylander PL (1967) Catalytic hydrogenation over platinum
metals. Academic Press, New York
X ¼
ꢂ 100
ð3Þ
CB;0
¨
22. Renner H, Schlamp G, Kleinwachter I, Drost E, Luschow HM,
Tews P, Panster P, Diehl M, Lang J, Kreuzer T, Knodler A, Starz
¨
CBA
¨
S ¼
ꢂ 100;
ð4Þ
X
KA, Dermann K, Rothaut J, Drieselmann R, Peter C, Schiele R
(2012) Platinum group metals and compounds. Ullmann’s ency-
where CB,0, CB, and CBA are the concentrations (wt%) of
benzaldehyde before the reaction, benzaldehyde after the
reaction, and benzyl alcohol, respectively.
´
23. Rodrıguez-Reinoso F (1998) Carbon 36:159
24. Toebes ML, van Dillen JA, de Jong KP (2001) J Mol Catal A:
Chem 173:75
Initial activities of the catalysts (1 h after the onset of
reaction) were calculated from benzaldehyde conversions
taking into account the dispersion of ruthenium estimated
by pulse chemisorption.
´
´
25. Rodrıguez-Reinoso F, Sepulveda-Escribano A (2009) In: Serp F,
Figueiredo JL (eds) Carbon materials for catalysis. John Wiley &
Sons, Hoboken
26. Zhu J, Holmen A, Chen D (2013) ChemCatChem 5:378
27. Nishimura S (2001) Handbook of heterogeneous catalytic hy-
drogenation for organic synthesis. John Wiley & Sons, New York
28. Vannice MA, Poondi D (1997) J Catal 169:166
Acknowledgments The authors are grateful to T. V. Kireeva, A.
V. Shilova, T. I. Gulyaeva, E. N. Kudrya, O. V. Maevskaya, and A.
B. Arbuzov for their help with experimental work. Characterization of
the catalysts and identification of reaction products by GC–MS were
performed using equipment of the Center of Collective Usage of the
Omsk Scientific Center, Siberian Branch of the Russian Academy of
Sciences. The study was financially supported by the Russian Foun-
dation for Basic Research (Project 12-03-00153-a).
29. Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA,
´
Rouquerol J, Siemieniewska T (1985) Pure Appl Chem 57:603
30. Belskaya OB, Mironenko RM, Likholobov VA (2013) Theor Exp
Chem 48:381
31. Pyanova LG, Luzyanina LS, Drozdov VA, Veselovskaya AV,
Arbuzov AB, Likholobov VA (2010) Prot Met Phys Chem Surf
46:320
32. Fanning PE, Vannice MA (1993) Carbon 31:721
33. Bansal RC, Goyal M (2005) Activated carbon adsorption. CRC
Press, Boca Raton
References
34. Ruhl T, Breitscheidel B, Henkelmann J, Henne A, Lebkucher R,
Knoll K, Naegele P, Gausepohl H, Weiguny S, Niessner N (2001)
Process for reacting an organic compound in the presence of a
1. Rase HF (2000) Handbook of commercial catalysts. Heteroge-
neous catalysts. CRC Press, Boca Raton
123