Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO

doi:10.1016/j.cjche.2015.06.006

Chin.J.Chem.Eng. ›› 2016, Vol. 24 ›› Issue (1): 126-131.DOI: 10.1016/j.cjche.2015.06.006

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Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO

Song Zhang, Zhibao Huo, Dezhang Ren, Jiang Luo, Jun Fu, Lu Li, Fangming Jin

School of Environmental Science and Engineering, The State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China

Received:2014-09-21 Revised:2015-04-19 Online:2016-02-23 Published:2016-01-28
Contact: Zhibao Huo, Fangming Jin
Supported by:
Supported by the National Natural Science Foundation of China (21277091), the State Key Program of National Natural Science Foundation of China (21436007), Key Basic Research Projects of Science and Technology Commission of Shanghai Municipality (14JC1403100), the Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning (ZXDF160002), and the Project-sponsored by SRF for ROCS, SEM (BG1600002).

Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO

Song Zhang, Zhibao Huo, Dezhang Ren, Jiang Luo, Jun Fu, Lu Li, Fangming Jin

School of Environmental Science and Engineering, The State Key Laboratory of Metal Matrix Composites, Shanghai Jiao Tong University, Shanghai 200240, China

通讯作者: Zhibao Huo, Fangming Jin
基金资助:
Supported by the National Natural Science Foundation of China (21277091), the State Key Program of National Natural Science Foundation of China (21436007), Key Basic Research Projects of Science and Technology Commission of Shanghai Municipality (14JC1403100), the Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning (ZXDF160002), and the Project-sponsored by SRF for ROCS, SEM (BG1600002).

Abstract

Abstract: An efficient conversion of biomass-derived ethyl lactate to 1,2-propanediol (1,2-PDO) over CuO was investigated. Among the catalysts we tested, CuO, Cu₂O and Co showed excellent catalytic activity for the conversion of ethyl lactate to 1,2-PDO in water, and CuO was more active and gave the best result. The 1,2-PDO yield of 93.6% was achieved when Zn acted as a reductant. The results indicated that in situ formed hydrogen by the oxidation of Zn in water is more effective than gaseous hydrogen, which failed to produce the 1,2-PDO from ethyl lactate. From a practical point of view, the present method may provide a useful route for the production of 1,2-PDO from ethyl lactate.

Key words: Biomass, 1,2-propanediol, Ethyl lactate, CuO, Hydrothermal reactions

摘要： An efficient conversion of biomass-derived ethyl lactate to 1,2-propanediol (1,2-PDO) over CuO was investigated. Among the catalysts we tested, CuO, Cu₂O and Co showed excellent catalytic activity for the conversion of ethyl lactate to 1,2-PDO in water, and CuO was more active and gave the best result. The 1,2-PDO yield of 93.6% was achieved when Zn acted as a reductant. The results indicated that in situ formed hydrogen by the oxidation of Zn in water is more effective than gaseous hydrogen, which failed to produce the 1,2-PDO from ethyl lactate. From a practical point of view, the present method may provide a useful route for the production of 1,2-PDO from ethyl lactate.

关键词: Biomass, 1,2-propanediol, Ethyl lactate, CuO, Hydrothermal reactions

Song Zhang, Zhibao Huo, Dezhang Ren, Jiang Luo, Jun Fu, Lu Li, Fangming Jin. Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO[J]. Chin.J.Chem.Eng., 2016, 24(1): 126-131.

Song Zhang, Zhibao Huo, Dezhang Ren, Jiang Luo, Jun Fu, Lu Li, Fangming Jin. Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO[J]. Chinese Journal of Chemical Engineering, 2016, 24(1): 126-131.

References

[1] G.X. Xu, C. Shao, Z.L. Xiu, Optimizing control of bio-dissimilation process of glycerol to 1,3-propanediol, Chin. J. Chem. Eng. 16 (2008) 128-134.

[2] R.J. van Putten, J.C. van derWaal, E. de Jong, C.B. Rasrendra, H.J. Heeres, J.G. de Vries, Hydroxymethylfurfural, a versatile platform chemical made from renewable resources, Chem. Rev. 133 (2013) 1499-1597.

[3] Y. Roman-Leshkov, C.J. Barrett, Z.Y. Liu, J.A. Dumesic, Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates, Nature 447 (2007) 982-985.

[4] C.S. Zhou, X.J. Yu, H.L. Ma, R.H. He, V. Saritporn, Optimization on the conversion of bamboo shoot shell to levulinic acidwith environmentally benign acidic ionic liquid and response surface analysis, Chin. J. Chem. Eng. 21 (2013) 544-550.

[5] R.K. Saxena, P. Anand, S. Saran, J. Isar, L. Agarwal, Microbial production and applications of 1,2-propanediol, Indian J. Microbiol. 50 (2010) 2-11.

[6] D.C. Cameron, N.E. Altaras, M.L. Hoffman, A.J. Shaw, Metabolic engineering of propanediol pathways, Biotechnol. Prog. 14 (1998) 116-125.

[7] E.S. Lipinsky, R.G. Sinclair, Biodegradable materials: state of art and future perspectives, Chem. Eng. Prog. 82 (1986) 26-29.

[8] A. Corma, S. Iborra, A. Velty, Chemical routes for the transformation of biomass into chemicals, Chem. Rev. 38 (2007) 2411-2502.

[9] J.H. Clark, The home of cutting-edge research on the development of alternative sustainable technologies, Green Chem. (2006) 17-21.

[10] Z. Han, L. Rong, J. Wu, L. Zhang, Z. Wang, K. Ding, Catalytic hydrogenation of cyclic carbonates: a practical approach from CO₂ and epoxides to methanol and diols, Angewandte 51 (2012) 13041-13045.

[11] G. Fan, Y. Zhang, Y. Zhou, R. Li, H. Chen, X. Li, Synthesis of ZnO and ZnO₂ nanoparticles by the oil-in-water microemulsion reaction method, Chem. Lett. 37 (2008) 132-134.

[12] G. Luo, S. Yan,M. Qiao, J. Zhuang, K. Fan, Effect of tin on Ru-B/γ-Al₂O₃ catalyst for the hydrogenation of ethyl lactate to 1,2-propanediol, Appl. Catal. 275 (2004) 95-102.

[13] L. Huang, Y. Zhu, H. Zheng, M. Du, Y. Li, Vapor-phase hydrogenolysis of biomassderived lactate to 1,2-propanediol over supported metal catalysts, Appl. Catal. 349 (2008) 204-211.

[14] J. Feng, W. Xiong, Y. Jia, J. Wang, D. Liu, R. Qin, Hydrogenation of ethyl lactate over ruthenium catalysts in an additive-free catalytic system, React. Kinet. Mech. (2008) 89-97.

[15] N. Akiya, P.E. Savage, Roles of water for chemical reactions in high-temperature water, Chem. Rev. 102 (2002) 2725-2750.

[16] M. Watanabe, T. Sato, H. Inomata, R.L. Smith, K. Arai, A. Kruse, E. Dinjus, Chemical reactions of C1 compounds in near-critical and supercritical water, Chem. Rev. 104 (2004) 5803-5822.

[17] R.W. Shaw, Y.B. Brill, A.A. Clifford, C.A. Eckert, E.U. Franck, Dissipative hydrodynamics of rigid spherical particles, Chem. Eng. 23 (2010) 23-26.

[18] W.L. Marshall, E.U. Frank, Ion product of water substance, 0-1000 ℃, 1-10,000 bars New International Formulation and its background, J. Phys. Chem. Ref. Data (1981) 295-304.

[19] L.L. Xu, Z.B.Huo, J. Fu, F.M. Jin,Highly efficient conversion of biomass-derived glycolide to ethylene glycol over CuO in water, Chem. Commun. 50 (2014) 6009-6012.

[20] F. Jin, A. Kishita, T. Moriya, H. Enomoto, Kinetics of oxidation of food wastes with H₂O₂ in supercritical water, Supercrit. Fluids 19 (2001) 251-262.

[21] Y. Li, G. Xu, C. Liu, B. Eliasson, B. Xue, Gram-scale synthesis of zinc oxide nanorods in basic ethanol solutions, Energy Fuel 15 (2001) 299-302.

[22] D. Larcher, R. Patrice, Preparation of metallic powders and alloys in polyol media: a thermodynamic approach, J. Solid State Chem. 154 (2000) 405-411.

[23] F.L.P. Resende, P.E. Savage, Effect on metal on superficial water gasification of cellulose and lignin, Ind. Eng. Chem. Res. 49 (2010) 2694-2700.

[24] D.C. Elliott, Catalytic hydrothermal gasification of biomass, Biofuels Bioprod. Biorefin. 2 (2008) 254-265.

[25] Z.P. Yan, L. Lin, S. Liu, Synthesis of γ-valerolactone by hydrogenation of biomassderived levulinic acid over Ru/C catalyst, Energy Fuel 23 (2009) 3853-3858.

[26] A.P.G. Kieboom, F. van Rantwiik, Hydrogenation and Hydrogenolysis in Synthetic Organic Chemistry, Science Press, Beijing, China, 1981. 295-300.

Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO

Catalytic conversion of ethyl lactate to 1,2-propanediol over CuO

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