Chem. J. Chinese Universities ›› 2019, Vol. 40 ›› Issue (5): 1029.doi: 10.7503/cjcu20180668
• Physical Chemistry • Previous Articles Next Articles
DING Zhongxie1, LIANG Jinhua2, LIU Zhen1, SHEN Jiecan1, ZHANG Feng2, REN Xiaoqian1,*(), JIANG Min3
Received:
2018-09-29
Online:
2019-04-12
Published:
2019-04-12
Contact:
REN Xiaoqian
E-mail:xqren@njtech.edu.cn
Supported by:
CLC Number:
TrendMD:
DING Zhongxie,LIANG Jinhua,LIU Zhen,SHEN Jiecan,ZHANG Feng,REN Xiaoqian,JIANG Min. Functional Specific Heteropoly Acid Ionic Liquid Catalyzed Direct Esterification of Aqueous Succinate Solution†[J]. Chem. J. Chinese Universities, 2019, 40(5): 1029.
Fig.2 XRD patterns of [HMT-4PS][HPA](A) a. H3PMO12O40, b. [HMT-4PS]3[PMO]4; (B) a. H3PW12O40, b. [HMT-4PS]3[PW]4;(C) a. H4SiW12O40, b. [HMT-4PS][SiW].
Catalyst | ABET/(m2·g-1) | VT/(cm3·g-1) | AM/(m2·g-1) | VM/(cm3·g-1) |
---|---|---|---|---|
[HMT-4PS]3[PMO]4 | 33.334 | 0.026 | 12.887 | 0.006 |
[HMT-4PS]3[PW]4 | 48.777 | 0.028 | 35.559 | 0.018 |
[HMT-4PS][SiW] | 28.648 | 0.021 | 10.499 | 0.004 |
Table 1 Textural properties of the catalysts*
Catalyst | ABET/(m2·g-1) | VT/(cm3·g-1) | AM/(m2·g-1) | VM/(cm3·g-1) |
---|---|---|---|---|
[HMT-4PS]3[PMO]4 | 33.334 | 0.026 | 12.887 | 0.006 |
[HMT-4PS]3[PW]4 | 48.777 | 0.028 | 35.559 | 0.018 |
[HMT-4PS][SiW] | 28.648 | 0.021 | 10.499 | 0.004 |
Catalyst | Mass fraction(%, E/T*) | n(N)/n(S) | |||
---|---|---|---|---|---|
C | H | N | S | ||
[HMT-4PS]3[PMO]4 | 6.95/7.06 | 1.10/1.18 | 1.92/1.83 | 3.99/4.18 | 1.10 |
[HMT-4PS]3[PW]4 | 4.79/4.84 | 0.93/0.81 | 1.13/1.25 | 2.41/2.86 | 1.07 |
[HMT-4PS][SiW] | 6.28/6.16 | 0.92/1.04 | 1.75/1.60 | 3.44/3.65 | 1.16 |
Table 2 Elemental analysis results of the catalysts
Catalyst | Mass fraction(%, E/T*) | n(N)/n(S) | |||
---|---|---|---|---|---|
C | H | N | S | ||
[HMT-4PS]3[PMO]4 | 6.95/7.06 | 1.10/1.18 | 1.92/1.83 | 3.99/4.18 | 1.10 |
[HMT-4PS]3[PW]4 | 4.79/4.84 | 0.93/0.81 | 1.13/1.25 | 2.41/2.86 | 1.07 |
[HMT-4PS][SiW] | 6.28/6.16 | 0.92/1.04 | 1.75/1.60 | 3.44/3.65 | 1.16 |
Solvent | Solubility of catalyst | ||
---|---|---|---|
[HMT-4PS]3[PW]4 | [HMT-4PS]3[PMo]4 | [HMT-4PS][SiW] | |
Water | * | * | * |
Acetonitrile | * | * | * |
Methanol | * | * | * |
Ethanol | + | + | + |
Isopropanol | + | + | + |
Acetone | + | + | + |
1-Butanol | — | — | — |
Ethyl acetate | — | — | — |
Ethyl ether | — | — | — |
Dichloromethane | — | — | — |
1,2-Dichloroethane | — | — | — |
Benzene | — | — | — |
Cyclohexane | — | — | — |
Table 3 Solubility of various catalysts
Solvent | Solubility of catalyst | ||
---|---|---|---|
[HMT-4PS]3[PW]4 | [HMT-4PS]3[PMo]4 | [HMT-4PS][SiW] | |
Water | * | * | * |
Acetonitrile | * | * | * |
Methanol | * | * | * |
Ethanol | + | + | + |
Isopropanol | + | + | + |
Acetone | + | + | + |
1-Butanol | — | — | — |
Ethyl acetate | — | — | — |
Ethyl ether | — | — | — |
Dichloromethane | — | — | — |
1,2-Dichloroethane | — | — | — |
Benzene | — | — | — |
Cyclohexane | — | — | — |
No. | Catalyst | Conv.(%) | SD(%) | SM(%) | A/(mmol·g-1) | Reaction phenomenon |
---|---|---|---|---|---|---|
1 | [HMT-4PS]3[PMO]4 | 74.8 | 89.8 | 10.2 | 1.03 | Emulsion |
2 | [HMT-4PS]3[PW]4 | 79.3 | 92.9 | 7.1 | 1.16 | Emulsion |
3 | [HMT-4PS][SiW] | 77.1 | 90.9 | 9.1 | 1.08 | Emulsion |
4 | [MIMPS]3PMo12O40 | 57.6 | 76.5 | 23.5 | 1.04 | Heterogeneous |
5 | [MIMPS]3PW12O40 | 62.2 | 80.4 | 19.6 | 0.66 | Heterogeneous |
6 | [MIMPS]4SiW12O40 | 56.3 | 78.2 | 21.8 | 0.87 | Heterogeneous |
7 | H2SO4 | 46.8 | 68.5 | 31.5 | — | Homogeneous |
8 | — | 13.6 | 53.9 | 46.1 | — | Homogeneous |
Table 4 Catalytic performance of various catalysts*
No. | Catalyst | Conv.(%) | SD(%) | SM(%) | A/(mmol·g-1) | Reaction phenomenon |
---|---|---|---|---|---|---|
1 | [HMT-4PS]3[PMO]4 | 74.8 | 89.8 | 10.2 | 1.03 | Emulsion |
2 | [HMT-4PS]3[PW]4 | 79.3 | 92.9 | 7.1 | 1.16 | Emulsion |
3 | [HMT-4PS][SiW] | 77.1 | 90.9 | 9.1 | 1.08 | Emulsion |
4 | [MIMPS]3PMo12O40 | 57.6 | 76.5 | 23.5 | 1.04 | Heterogeneous |
5 | [MIMPS]3PW12O40 | 62.2 | 80.4 | 19.6 | 0.66 | Heterogeneous |
6 | [MIMPS]4SiW12O40 | 56.3 | 78.2 | 21.8 | 0.87 | Heterogeneous |
7 | H2SO4 | 46.8 | 68.5 | 31.5 | — | Homogeneous |
8 | — | 13.6 | 53.9 | 46.1 | — | Homogeneous |
Fig.4 Effects of reaction temperatures on conversion of SAReaction conditions: succinic acid(mass fraction of 8% in aqueous solution), n(methanol)∶n(succinic acid)=30∶1, catalyst(mass fraction of 5% based on SA aqueous solution).
Fig.5 Effects of catalyst amounts on conversion of SAReaction conditions: succinic acid(mass fraction of 8% in aqueous solution), n(methanol)∶n(succinic acid)=30∶1, 80 ℃.
Fig.6 Effects of molar ratio of SA to methanol on conversion of SAReaction conditions: succinic acid(mass fraction of 8% in aqueous solution), 80 ℃, 8 h, catalyst(mass fraction of 5% based on SA aqueous solution).
Fig.7 Reusability of catalyst [HMT-4PS]3[PW]4Reaction conditions: succinic acid(mass fraction of 8% in aqueous solution), 80 ℃, 8 h, n(methanol)∶n(succinic acid)=30∶1, catalyst(mass fraction of 5% based on SA aqueous solution).
Fig.8 Reaction phenomena(A) and reaction process(B) Catalyst esterification and recovery of low concentration succinic acid solution: a. Before esterification; b. catalytic esterification of low concentration succinic acid solution in emulsion droplets; c. after esterification; d. catalyst recovery.
[1] | Ouyang P.K., Bio-based Polymer Material, Chemical Industry Press, Beijing, 2012, 122—136 |
(欧阳平凯. 生物基高分子材料, 北京: 化学工业出版社, 2012, 122—136) | |
[2] | Bechthold I., Bretz K., Kabasci S., Kopitzky R., Springer A., Chem. Eng. Technol., 2008, 31(5), 647—654 |
[3] | Cheng K. K., Zhao X. B., Zeng J., Zhang J. A., Biofuels. Bioprod. Biorefin., 2012, 6(3), 302—318 |
[4] | Muzumdar A. V., Sawant S. B., Pangarkar V. G., Org. Process Res. Dev., 2004, 8(4), 685—688 |
[5] | Kondrashova M. N., Ljubimova T. B., Maevskij E. I., Method for Preparing Succinic Acid, RU 2237056,2004-09-27 |
[6] | Glassner D. A., Datta R., Process for the Production and Purification of Succinic Acid, US 5143834,1992-09-01 |
[7] | Guan G. F., Xu C., Yao H. Q., Environ. Prot. Chem. Ind., 2004, 24(4), 240—243 |
(管国锋, 徐晨, 姚虎卿. 化工环保, 2004, 24(4), 240—243) | |
[8] | Ye X. J., Gong L., Wang H. L., Wang X. J., Xu H. Z., Xue D. H., Chem. Bioeng., 2014, 31(4), 32—36 |
(叶小金, 宫莉, 王红蕾, 王晓俊, 徐洪章, 薛冬桦. 化学与生物工程, 2014, 31(4), 32—36) | |
[9] | Li Q., Wang D., Wu Y., Li W., Zhang Y., Xing J., Su Z., Sep. Purif. Technol., 2010, 72(3), 294—300 |
[10] | Sun X., Wang Q., Zhao W., Ma H., Sakata K., Sep. Purif. Technol., 2006, 49(1), 43—48 |
[11] | Zhao W., Sun X., Wang Q., Ma H., Teng Y., Biomass Bioenergy,2009, 33(1), 21—25 |
[12] | Budarin V., Luque R., Macquarrie D. J., Clark J. H., Chem. Eur. J., 2010, 13(24), 6914—6919 |
[13] | Delhomme C., Goh S. L. M., Kühn F. E., Weuster-Botz D. J., J. Mol. Catal. B: Enzym., 2012, 80, 39—47 |
[14] | Leng Y., Wang J., Zhu D., Ren X., Ge H., Shen L., Angew. Chem. Int. Ed.,2010, 48(1), 168—171 |
[15] | Cole A. C., Jensen J. L., Ntai I., Tran K. L. T., Weaver K. J., Forbes D. C., Davis J. H., J. Am. Chem. Soc., 2002, 124(21), 5962—5963 |
[16] | Liu S., Zhou H., Yu S., Xie C., Liu F., Song Z., Chem. Eng. J.,2012, 174(1), 396—399 |
[17] | Gai B. B., He H., Zhao Y. H., Mao Z., Fu H., Chem. Res. Chinese Universities,2016, 32(4), 527—529 |
[18] | Ma Q., Tong J. H., Su L. D., Wang W. H., Ma W. M., Bo L. L., Acta Phys. Chim. Sin., 2016, 32(12), 2961—2967 |
(马青, 童金辉, 宿玲弟, 王文慧, 马文梅, 薄丽丽. 物理化学学报, 2016, 32(12), 2961—2967) | |
[19] | Ilgen F., Ott D., Kralisch D., Reil C., Palmberger A., König B., Green Chem., 2009, 11(12), 1948—1954 |
[20] | Cheng M., Tian S., Guan H., Wang S., Wang X., Jiang Z., Appl. Catal. B,2011, 107(1), 104—109 |
[21] | Duan X., Sun G., Sun Z., Li J., Wang S., Wang X., Li S., Jiang Z., Catal. Commun., 2013, 42(4), 125—128 |
[22] | An Y., Lu L., Li C. M., Cheng S. F., Gao G. H., Chinese J. Catal., 2009, V30(12), 1222—1226 |
(安莹, 陆亮, 李才猛, 程时富, 高国华. 催化学报,2009, V30(12), 1222—1226) | |
[23] | Ramesh S., Lu S. C., J. Mater. Res., 2011, 26(23), 2945—2951 |
[24] | Nemanashi M., Noh J. H., Meijboom R. J., Mater. Sci., 2018, 53(18), 12663—12678 |
[25] | Park C., Lee J., Kim C., Chem. Commun., 2011, 47(44), 12042—12056 |
[26] | Tomalia D. A., Naylor A. M., Iii W. A. G., Angew. Chem. Int. Ed.,2010, 29(2), 138—175 |
[27] | Zhang F., Liang J. H., Hu X., Wang J. G., Chen L. L., Ren X. Q., Jiang M., J. Chem. Eng., 2015, 66(7), 2488—2497 |
(张锋, 梁金花, 胡曦, 王俊格, 陈刘龙, 任晓乾, 姜岷. 化工学报, 2015, 66(7), 2488—2497) | |
[28] | Kapoor M. P., Kuroda H., Yanagi M., Nanbu H., Juneja L. R., TopCatal., 2009, 52(6/7), 634—642 |
[29] | Duan X. X., Zhong S., Li X. Y., Wang X. H., Wang S. T., Li S. W., Energy Technol., 2015, 3(8), 871—877 |
[30] | Li H., Qiao Y., Hua L., Hou Z., Feng B., Pan Z., Hu Y., Wang X., Zhao X., Yu Y., Chem. Cat. Chem,2010, 2(9), 1165—1170 |
[31] | Li C., Jiang Z. X., Gao J. B., Yang Y. X., Wang S. J., Tian F. P., Sun F. X., Sun X. P., Ying P. L., Han C. R., Chem. Eur. J.,2010, 10(9), 2277—2280 |
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