Citation: Li Rongrong, Zhao Jia, Han Deman, Li Xiaonian. Pd/C modified with Sn catalyst for liquid-phase selective hydrogenation of maleic anhydride to gamma-butyrolactone[J]. Chinese Chemical Letters, ;2017, 28(6): 1330-1335. doi: 10.1016/j.cclet.2017.04.028 shu

Pd/C modified with Sn catalyst for liquid-phase selective hydrogenation of maleic anhydride to gamma-butyrolactone

Li Rongrong ^a,b ,
Zhao Jia ^a ,
Han Deman ^b,, ,
Li Xiaonian ^a,,

a.
Industrial Catalysis Institute of Zhejiang University of Technology, Hangzhou 310014, China
b.
School of Pharmaceutical and Chemical Engineering, Tai Zhou University, Taizhou 317000, China

Corresponding author: Han Deman, hdm@tzc.edu.cn Li Xiaonian, xnli@zjut.edu.cn
Received Date: 5 March 2017
Revised Date: 20 April 2017
Accepted Date: 24 April 2017
Available Online: 27 June 2017

Figures(5)

Pd catalysts suffered from poor selectivity and stability for liquid-phase hydrogenation of maleic anhydride (MA) to gamma-butyrolactone (GBL). Thus, Pd/C catalysts modified with different Sn loadings were synthesized, and characterized by XRD, XPS, TEM and elemental mapping. The types of alloy phase and the amounts of the surface Pd-SnOx sites altered along with Sn/Pd mass ratios from 0-1.0 synthesized in the process of preparation. The maximum reaction rate was 0.57 mol-GBL/(mol-Pd min) and selectivity was 95.94% when the Sn/Pd mass ratio was 0.6. It might be attributed to the formation of Pd₂Sn alloy and less amounts of Pd-SnOx sites.
- Bimetallic catalysts,
- Sn/Pd mass ratio,
- Maleic anhydride,
- Selective hydrogenation,
- Gamma-butyrolactone
1. [1]
  Zou Y., Leng Y., Huang C.. Measurement and correlation of solubility of succinic anhydride in pure solvents and binary solvent mixtures[J]. J. Chem. Thermodyn., 2017,104:82-90. doi: 10.1016/j.jct.2016.09.025
2. [2]
  Chen L.F., Guo P.J., Zhu L.J.. Preparation of Cu/SBA-15 catalysts by different methods for the hydrogenolysis of dimethyl maleate to 1, 4-butanediol[J]. Appl. Catal. A, 2009,356:129-136. doi: 10.1016/j.apcata.2008.12.029
3. [3]
  Harris N., Tuck M.W.. Butanediol via maleic anhydride[J]. Hydrocarbon Process, 1990,69:79-82.
4. [4]
  Intra B., Euanorasetr J., Nihira T.. Characterization of a gammabutyrolactone synthetase gene homologue (stcA) involved in bafilomycin production and aerial mycelium formation in Streptomyces sp. SBI034[J]. Appl. Microbiol. Biotechnol., 2016,100:2749-2760. doi: 10.1007/s00253-015-7142-8
5. [5]
  Brownstein A.M.. 1, 4-Butanediol and tetrahydrofuran:exemplary smallvolume commodities[J]. Chem. Technol., 1991,21:506-510.
6. [6]
  Hong U.G., Kim J.K., Lee J.. Hydrogenation of succinic acid to tetrahydrofuran (THF) over ruthenium-carbon composite (Ru-C) catalyst[J]. Appl. Catal. A, 2014,469:466-471. doi: 10.1016/j.apcata.2013.10.029
7. [7]
  Huang Y., Ma Y., Cheng Y.. Active ruthenium catalysts prepared by cacumen platycladi leaf extract for selective hydrogenation of maleic anhydride[J]. Appl. Catal. A, 2015,495:124-130. doi: 10.1016/j.apcata.2015.02.014
8. [8]
  Ma Y., Huang Y., Chen Y.. Selective liquid-phase hydrogenation of maleic anhydride to succinic anhydride on biosynthesized ru-based catalysts[J]. Catal. Commun., 2014,57:40-44. doi: 10.1016/j.catcom.2014.08.001
9. [9]
  Zhang B., Zhu Y., Ding G.. Modification of the supported Cu/SiO₂ catalyst by alkaline earth metals in the selective conversion of 1, 4-butanediol to γ-butyrolactone[J]. Appl. Catal. A 443-, 2012,444:191-201.
10. [10]
  Bertone M.E., Regenhardt S.A., Meyer C.I.. Highly selective Cumodified Ni/SiO₂-Al₂O₃ catalysts for the conversion of maleic anhydride to -butyrolactone in gas phase[J]. Top. Catal., 2016,59:1-9. doi: 10.1007/s11244-015-0511-9
11. [11]
  Zhang D., Yin H., Xue J.. Selective hydrogenation of maleic anhydride to tetrahydrofuran over Cu-Zn-M (M=Al, Ti, Zr) catalysts using ethanol as a solvent[J]. Ind. Eng. Chem. Res., 2009,48:11220-11224. doi: 10.1021/ie9013875
12. [12]
  Kannapu H.P.R., Neeli C.K.P., Rao K.S.R.. Unusual effect of cobalt on Cu-MgO catalyst for the synthesis of γ-butyrolactone and aniline via coupling reaction[J]. Catal. Sci. Technol., 2016,6:5494-5503. doi: 10.1039/C6CY00397D
13. [13]
  Zhang D., Yin H., Ge C.. Selective hydrogenation of maleic anhydride to gbutyrolactone and tetrahydrofuran by Cu-Zn-Zr catalyst in the presence of ethanol[J]. J. Ind. Eng. Chem., 2009,15:537-543. doi: 10.1016/j.jiec.2009.01.010
14. [14]
  Regenhardt S.A., Meyer C.I., Garetto T.F.. Selective gas phase hydrogenation of maleic anhydride over Ni-supported catalysts:effect of support on the catalytic performance[J]. Appl. Catal. A, 2012,449:81-87. doi: 10.1016/j.apcata.2012.09.023
15. [15]
  Bertone M.E., Meyer C.I., Regenhardt S.A.. Highly selective conversion of maleic anhydride to γ-butyrolactone over Ni-supported catalysts prepared by precipitation-deposition method[J]. Appl. Catal. A, 2015,503:135-146. doi: 10.1016/j.apcata.2015.07.013
16. [16]
  Li J., Tian W., Shi L.. Hydrogenation of maleic anhydride to succinic anhydride over Ni/HY-Al₂O₃[J]. Ind. Eng. Chem. Res., 2010,49:11837-11840. doi: 10.1021/ie101072v
17. [17]
  Li J., Tian W.P., Wang X.. Nickel and nickel-platinum as active and selective catalyst for the maleic anhydride hydrogenation to succinic anhydride[J]. Chem. Eng. J., 2011,175:417-422. doi: 10.1016/j.cej.2011.09.023
18. [18]
  Wei S., Pan C., Yang X.. Coupling reaction of 1, 4-butanediol with maleic anhydride over Cr-Cu/SiO₂ catalysts[J]. Acta Chim. Sin., 2008,661287.
19. [19]
  Li S., Wang X., Liu X.. Aqueous-phase hydrogenation of biomass-derived itaconic acid to methyl-γ-butyrolactone over Pd/C catalysts:effect of pretreatments of active carbon[J]. Catal. Commun., 2015,61:92-96. doi: 10.1016/j.catcom.2014.12.017
20. [20]
  Zhang C., Chen L., Cheng H.. Atomically dispersed Pd catalysts for the selective hydrogenation of succinic acid to γ-butyrolactone[J]. Catal. Today, 2016,276:55-61. doi: 10.1016/j.cattod.2016.01.028
21. [21]
  Jin Z., Yu C., Wang X.. Liquid phase hydrodechlorination of chlorophenols at lower temperature on a novel Pd catalyst[J]. J. Hazard Mater., 2011,186:1726-1732. doi: 10.1016/j.jhazmat.2010.12.058
22. [22]
  Kopinke F.D., D. Angeles-Wedler, Fritsch D.. Pd-catalyzed hydrodechlorination of chlorinated aromatics in contaminated waterseffects of surfactants, organic matter and catalyst protection by silicone coating[J]. Appl. Catal. B Environ., 2010,96:323-328. doi: 10.1016/j.apcatb.2010.02.028
23. [23]
  Rong H., Cai S., Niu Z.. Composition-dependent catalytic activity of bimetallic nanocrystals:AgPd-catalyzed hydrodechlorination of 4-chlorophenol[J]. ACS Catal., 2013,3:1560-1563. doi: 10.1021/cs400282a
24. [24]
  Pillai U.R., Sahle-Demessie E.. ChemInform abstract:selective hydrogenation of maleic anhydride to γ-butyrolactone over Pd/Al₂O₃ catalyst using supercritical CO₂ as solvent[J]. Chem. Commun., 2002,33:422-423.
25. [25]
  Pillai U.R., E. Sahle-Demessie, Young D.. Maleic anhydride hydrogenation over Pd/Al₂O₃ catalyst under supercritical CO₂ medium[J]. Appl. Catal. B, 2003,43:131-138. doi: 10.1016/S0926-3373(02)00305-3
26. [26]
  Vaidya S.H., Rode C.V., Chaudhari R.V.. Bimetallic Pt-Sn/γ-alumina catalyst for highly selective liquid phase hydrogenation of diethyl succinate to γ-butyrolactone[J]. Catal Commun., 2007,8:340-344. doi: 10.1016/j.catcom.2006.06.026
27. [27]
  Furukawa S., Endo M., Komatsu T.. Bifunctional catalytic system effective for oxidative dehydrogenation of 1-butene and n-butane using Pd-based intermetallic compounds[J]. ACS Catal., 2014,4:3533-3542. doi: 10.1021/cs500920p
28. [28]
  O. Lidor-Shalev, Zitoun D.. Reaction mechanism of amine-borane route towards Sn, Ni Pd, Pt nanoparticles[J]. RSC Adv., 2014,4:63603-63610. doi: 10.1039/C4RA11483C
29. [29]
  Esmaeili E., Mortazavia Y., Khodadadi A.A.. The role of tin-promoted Pd/MWNTs via the management of carbonaceous species in selective hydrogenation of high concentration acetylene[J]. Appl. Surf. Sci., 2012,263:513-522. doi: 10.1016/j.apsusc.2012.09.095
30. [30]
  Esmaeili E., Rashidi A.M., Khodadadi A.A.. Palladium-tin nanocatalysts in high concentrationacetylene hydrogenation:a novel deactivation mechanism[J]. Fuel Process Technol., 2014,120:113-122. doi: 10.1016/j.fuproc.2013.12.015
31. [31]
  Du W., Mackenzie K.E., Milano D.F.. Palladium-tin alloyed catalysts for the ethanol oxidation reaction in an alkaline medium[J]. ACS Catal., 2012,2:287-297. doi: 10.1021/cs2005955
32. [32]
  Zhao J., Xu X., Li X.. Promotion of Sn on the Pd/AC catalyst for the selective hydrogenation of cinnamaldehyde[J]. Catal. Commun., 2014,43:102-106. doi: 10.1016/j.catcom.2013.09.019
33. [33]
  Jung S.M., Godard E., Jung S.Y.. Liquid-phase hydrogenation of maleic anhydride over Pd-Sn/SiO₂[J]. Catal. Today, 2003,87:171-177. doi: 10.1016/j.cattod.2003.10.010
34. [34]
  Esmaeili E., Mortazavi Y., Khodadadi A.A.. The role of tin-promoted Pd/MWNTs via the management of carbonaceous species in selective hydrogenation of high concentration acetylene[J]. Appl. Surf. Sci., 2012,263:513-522. doi: 10.1016/j.apsusc.2012.09.095
35. [35]
  Modibedi R.M., Masombuka T., Mathe M.K.. Carbon supported Pd-Sn and Pd-Ru-Sn nanocatalysts for ethanol electro-oxidation in alkaline medium[J]. J. Hydrogen Energy, 2001,36:4664-4672.
36. [36]
  Lee A.F., Baddeley C.J., Tikhov M.S.. Structural and electronic properties of Sn overlayers and Pd/Sn surface alloys on Pd(111)[J]. Surf. Sci., 1997,373:195-209. doi: 10.1016/S0039-6028(96)01160-0
37. [37]
  Kovnir K., Osswald J., Armbrüster M.. Etching of the intermetallic compounds PdGa and Pd₃Ga₇:an effective way to increase catalytic activity[J]. J. Catal., 2009,264:93-103. doi: 10.1016/j.jcat.2009.03.007
38. [38]
  Kovnir K., Armbrüster M., Teschner D.. A new approach to well-defined, stable and site-isolated catalysts[J]. Sci. Technol. Adv. Mater., 2007,8:420-427. doi: 10.1016/j.stam.2007.05.004
39. [39]
  Teschner D., Pestryakov A., Kleimenov E.. High-pressure X-ray photoelectron spectroscopy of palladium model hydrogenation catalysts. Part 1:effect of gas ambient and temperature[J]. J. Catal., 2005,230186. doi: 10.1016/j.jcat.2004.11.036
40. [40]
  Teschner D., Pestryakov A., Kleimenov E.. High-pressure X-ray photoelectron spectroscopy of palladium model hydrogenation catalysts. Part 2:hydrogenation of trans-2-pentene on palladium[J]. J. Catal., 2005,230:195-203. doi: 10.1016/j.jcat.2004.11.035
41. [41]
  Jung S.M., Godard E., Jung S.Y.. Liquid-phase hydrogenation of maleic anhydride over Pd-Sn/SiO₂[J]. Catal. Today, 2003,87:171-177. doi: 10.1016/j.cattod.2003.10.010
42. [42]
  Sales E.A., Jove J., Mendes M.J.. Palladium, palladium-tin, and palladium-silver catalysts in the selective hydrogenation of hexadienes:TPR, mössbauer, and infrared studies of adsorbed CO[J]. J. Catal., 2000,195:88-95. doi: 10.1006/jcat.2000.2967
43. [43]
  Vilella I.M.J., S.R. deMiguel, Scelza O.A.. Pt, PtSn and PtGe catalysts supported on granular carbon for fine chemistry hydrogenation reactions[J]. J. Mol. Catal. A, 2008,284:161-171. doi: 10.1016/j.molcata.2008.01.017
44. [44]
  Haghofer A., Föttinger K., Girgsdies F.. In situ study of the formation and stability of supported Pd₂Ga methanol steam reforming catalysts[J]. J. Catal., 2012,286:13-21. doi: 10.1016/j.jcat.2011.10.007
45. [45]
  Dandekar A., Vannice M.A.. Crotonaldehyde hydrogenation on Pt/TiO₂ and Ni/TiO₂ SMSI catalysts[J]. J. Catal., 1999,183:344-354. doi: 10.1006/jcat.1999.2419
46. [46]
  Tauster S.J., Fung S.C., Garten R.L.. ChemInform abstract:strong metal-support interactions Group 8 noble metals supported in titanium dioxide[J]. J. Am. Chem. Soc., 1978,100:170-175. doi: 10.1021/ja00469a029
47. [47]
  Clarke J.K.A., Dempsey R.J., Baird T.. Selectivities for hydrocarbon reactions on SMSI titania-supported platinum formed by high-temperature reduction[J]. J. Catal., 1990,126:370-380. doi: 10.1016/0021-9517(90)90005-5
48. [48]
  Tauster S.J., Fung S.C.. Strong metal-support interactions:occurrence among the binary oxides of groups ⅡA-VB[J]. J. Catal., 1978,55:29-35. doi: 10.1016/0021-9517(78)90182-3
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