二氧化硅负载的不同碱金属硝酸盐催化乳酸缩合反应制备2, 3-戊二酮的催化性能比较研究

doi:10.3866/PKU.WHXB201606225

Abstract

Abstract:

The production of 2, 3-pentanedione from lactic acid over SiO₂-supported alkali metal nitrates under various conditions was investigated. Using nitrate (NO₃^-) as the anion, the effect of alkali metal cations on Claisen condensation of lactic acid into 2, 3-pentanedione was focused on. Among precursors such as LiNO₃, NaNO₃, KNO₃, and CsNO₃, CsNO₃ displayed the best catalytic performance. Characterization of the fresh and used catalysts by X-ray diffraction (XRD) and Fourier transform infrared (FT-IR) spectroscopy revealed that all MNO₃ (M=Li, Na, K, Cs) salts were transformed into alkali metal lactates during the reaction. Alkali metal lactates were identified as active species for catalytic Claisen condensation of lactic acid into 2, 3-pentanedione. CO₂ temperature-programmed desorption (TPD) results of the used catalysts showed that the CsNO₃/SiO₂ catalyst was the most alkaline. For that reason, the CsNO₃/SiO₂ catalyst displayed the highest catalytic performance of those examined. The effects of reaction temperature and loading amount of CsNO₃ on reaction performance were also discussed. Over the 4.4% (x, molar fraction) CsNO₃/SiO₂ catalyst, a 54.1% yield of 2, 3-pentanedione was achieved at 300 ℃.

Key words: Lactic acid, 2, 3-Pentanedione, Condensation, Alkali metal nitrate, Lactate

MSC2000:

O643

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Liang-Wei SUN,Xin-Li LI,Cong-Ming TANG. Comparative Study on Catalytic Performance of the Production of 2, 3-Pentanedione from Lactic Acid Condensation over SiO₂-Supported Alkali Metal Nitrates[J].Acta Phys. -Chim. Sin., 2016, 32(9): 2327-2336.

References

1	Sushkevich V. L. ; Ivanova I. I. ; Ordomsky V. V. ; Taarning E. ChemSusChem 2014, 7, 2527.
2	Redina E. A. ; Greish A. A. ; Mishin I. V. ; Kapustin G. I. ; Tkachenko O. P. ; Kirichenko O. A. ; Kustov L. M. Catal. Today 2015, 241, 246.
3	Takei T. ; Iguchi N. ; Haruta M. Catal. Surv. Asia 2011, 15, 80.
4	Nakamura Y. ; Murayama T. ; Ueda W. ChemCatChem 2014, 6, 741.
5	Santacesaria E. ; Carotenuto G. ; Tesser R. ; Di Serio M. Chem. Eng. J 2012, 179, 209.
6	Kannan S. ; Sen T. ; Sivasanker S. J. Catal 1997, 170, 304.
7	Sun J. M. ; Zhu K. K. ; Gao F. ; Wang C. M. ; Liu J. ; Peden C.H. F. ; Wang Y. J. Am. Chem. Soc 2011, 133, 11096.
8	Tang C. M. ; Peng J. S. ; Li X. L. ; Zhai Z. J. ; Bai W. ; Jiang N. ; Gao H. J. ; Liao Y. W. Green Chem 2015, 17, 1159.
9	Beerthuis R. ; Rothenberg G. ; Shiju N. R. Green Chem 2015, 17, 1341.
10	DeWilde J. F. ; Czopinski C. J. ; Bhan A. ACS Catal 2014, 4, 4425.
11	Katryniok B. ; Paul S. ; Dumeignil F. Green Chem 2010, 12, 1910.
12	Gao M. X. ; Liu Z. Z. ; Zhang M. H. ; Tong L. Catal. Lett 2014, 144, 2071.
13	Yan B. ; Tao L. Z. ; Liang Y. ; Xu B. Q. ACS Catal 2014, 4, 1931.
14	Yan B. ; Tao L. Z. ; Liang Y. ; Xu B. Q. ChemSusChem 2014, 7, 1568.
15	Tang C. M. ; Peng J. S. ; Fan G. C. ; Li X. L. ; Pu X. L. ; Bai W. Catal. Commun 2014, 43, 231.
16	Peng J. S. ; Li X. L. ; Tang C. M. ; Bai W. Green Chem 2014, 16, 108.
17	Blanco E. ; Delichere P. ; Millet J. M. M. ; Loridant S. Catal. Today 2014, 226, 185.
18	Ghantani V. C. ; Lomate S. T. ; Dongare M. K. ; Umbarkar S. B. Green Chem 2013, 15, 1211.
19	Sun P. ; Yu D. H. ; Fu K. M. ; Gu M. Y. ; Wang Y. ; Huang H. ; Ying H. H. Catal. Commun 2009, 10, 1345.
20	Zhang X. H. ; Lin L. ; Zhang T. ; Liu H. O. ; Zhang X. F. Chem. Eng. J 2016, 284, 934.
21	Blanco E. ; Lorentz C. ; Delichere P. ; Burel L. ; Vrinat M. ; Millet J. M. M. ; Loridant S. Appl. Catal. B: Environ 2016, 180, 596.
22	Tang C. M. ; Peng J. S. ; Li X. L. ; Zhai Z. J. ; Jiang N. ; Bai W. ; Gao H. J. ; Liao Y. W. RSC Adv 2014, 4, 28875.
23	Chai S. H. ; Yan B. ; Tao L. Z. ; Liang Y. ; Xu B. Q. Catal. Today 2014, 234, 215.
24	Chai S. H. ; Tao L. Z. ; Yan B. ; Vedrine J. C. ; Xu B. Q. RSC Adv 2014, 4, 4619.
25	Tao L. Z. ; Yan B. ; Liang Y. ; Xu B. Q. Green Chem 2013, 15, 696.
26	Tao L. Z. ; Chai S. H. ; Zuo Y. ; Zheng W. T. ; Liang Y. ; Xu B. Q. Catal. Today 2010, 158, 310.
27	Wang F. ; Dubois J. L. ; Ueda W. J. Catal 2009, 268, 260.
28	Katryniok B. ; Paul S. ; Capron M. ; Dumeignil F. ChemSusChem 2009, 2, 719.
29	Chai S. H. ; Wang H. P. ; Liang Y. ; Xu B. Q. Appl. Catal. AGen 2009, 353, 213.
30	Chai S. H. ; Wang H. P. ; Liang Y. ; Xu B. Q. Green Chem 2008, 10, 1087.
31	Chai S. H. ; Wang H. P. ; Liang Y. ; Xu B. Q. Green Chem 2007, 9, 1130.
32	Chai S. H. ; Wang H. P. ; Liang Y. ; Xu B. Q. J. Catal 2007, 250, 342.
33	Wang Y. L. ; Deng W. P. ; Wang B. J. ; Zhang Q. H. ; Wan X.Y. ; Tang Z. C. ; Wang Y. ; Zhu C. ; Cao Z. X. ; Wang G. C. ; Wan H. L. Nat. Commun 2013, 4, 2141.
34	Chen L. ; Ren S. J. ; Ye X. P. Fuel Process. Technol 2014, 120, 40.
35	Ramirez-Lopez C. A. ; Ochoa-Gomez J. R. ; Gil-Rio S. ; Gomez-Jimenez-Aberasturi O. ; Torrecilla-Soria J. J. Chem. Technol. Biotechnol 2011, 86, 867.
36	de Clippel F. ; Dusselier M. ; Van Rompaey R. ; Vanelderen P. ; Dijkmans J. ; Makshina E. ; Giebeler L. ; Oswald S. ; Baron G.V. ; Denayer J. F. M. ; Pescarmona P. P. ; Jacobs P. A. ; Sels B. F. J. Am. Chem. Soc 2012, 134, 10089.
37	Esposito D. ; Antonietti M. ChemSusChem 2013, 6, 989.
38	Tam M. S. ; Gunter G. C. ; Craciun R. ; Miller D. J. ; Jackson J. E. Ind. Eng. Chem. Res 1997, 36, 3505.
39	Wadley D. C. ; Tam M. S. ; Kokitkar P. B. ; Jackson J. E. ; Miller D. J. J. Catal 1997, 165, 162.
40	Gunter G. C. ; Langford R. H. ; Jackson J. E. ; Miller D. J. Ind. Eng. Chem. Res 1995, 34, 974.
41	Gunter G. C. ; Miller D. J. ; Jackson J. E. J. Catal 1994, 148, 252.
42	Tam M. S. ; Craciun R. ; Miller D. J. ; Jackson J. E. Ind. Eng. Chem. Res 1998, 37, 2360.
43	Schutyser W. ; Koelewijn S. F. ; Dusselier M. ; Van de Vyver S. ; Thomas J. ; Yu F. ; Carbone M. J. ; Smet M. ; Van Puyvelde P. ; Dehaen W. ; Sels B. F. Green Chem 2014, 16, 1999.
44	Zhang J. F. ; Feng X. Z. ; Zhao Y. L. ; Ji W. J. ; Au C. T. J. Ind. Eng. Chem 2014, 20, 1353.
45	Zhai Z. J. ; Li X. L. ; Tang C. M. ; Peng J. S. ; Jiang N. ; Bai W. ; Gao H. J. ; Liao Y. W. Ind. Eng. Chem. Res 2014, 53, 10318.
46	Zhang J. F. ; Zhao Y. L. ; Pan M. ; Feng X. Z. ; Ji W. J. ; Au C.T. ACS Catal 2011, 1, 32.
47	Zhang J. F. ; Lin J. P. ; Cen P. L. Can. J. Chem. Eng 2008, 86, 1047.
48	Tang C. ; Zhai Z. ; Li X. ; Sun L. ; Bai W. J. Catal 2015, 329, 206.
49	Tam M. S. ; Jackson J. E. ; Miller D. J. Ind. Eng. Chem. Res 1999, 38, 3873.
50	Tang C. M. ; Peng J. S. ; Li X. L. ; Zhai Z. J. ; Gao H. J. ; Bai W. ; Jiang N. ; Liao Y. W. Korean J. Chem. Eng 2016, 33, 99.
51	Tang C. M. ; Zhai Z. J. ; Li X. L. ; Sun L.W. ; Bai W. J. Taiwan Inst. Chem. Eng 2016, 58, 97.
52	Behrens M. ; Studt F. ; Kasatkin I. ; Kuhl S. ; Havecker M. ; Abild-Pedersen F. ; Zander S. ; Girgsdies F. ; Kurr P. ; Kniep B.L. ; Tovar M. ; Fischer R.W. ; Norskov J. K. ; Schlogl R. Science 2012, 336, 893.
53	Holm M. S. ; Saravanamurugan S. ; Taarning E. Science 2010, 328, 602.
54	Guan Y. ; Hensen E. J. M. J. Catal 2013, 305, 135.
55	N?fe G. ; López-Martínez M. A. ; Dyballa M. ; Hunger M. ; Traa Y. ; Hirth T. ; Klemm E. J. Catal 2015, 329, 413.
56	Deiana L. ; Jiang Y. ; Palo-Nieto C. ; Afewerki S. ; Incerti-Pradillos C. A. ; Verho O. ; Tai C.W. ; Johnston E. V. ; Cordova A. Angew. Chem. Int. Edit 2014, 53, 3447.
57	Jin X. J. ; Yamaguchi K. ; Mizuno N. Angew. Chem. Int. Edit 2014, 53, 455.

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Comparative Study on Catalytic Performance of the Production of 2, 3-Pentanedione from Lactic Acid Condensation over SiO₂-Supported Alkali Metal Nitrates

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Comparative Study on Catalytic Performance of the Production of 2, 3-Pentanedione from Lactic Acid Condensation over SiO₂-Supported Alkali Metal Nitrates