Catalytic Materials

Study on preparation of copper-based materials and its catalytic performance for hydrogenation of dimethyl succinate

  • WANG Peng ,
  • ZHAO Shanshan ,
  • LU Yanfei ,
  • LI Shisong ,
  • WANG Chunlei ,
  • SHU Chang ,
  • ZHANG Dongsheng
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  • 1.School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China
    2.CenerTech Tianjin Chemical Research and Design Institute Co. , Ltd. , Tianjin 300131, China

Received date: 2022-12-22

  Online published: 2023-10-16

Abstract

At present,acetylene aldehyde method,maleic anhydride method,butadiene method and propylene oxide method are used in the industry to produce 1,4-butanediol(BDO).However,due to the high energy consumption and pollution,the use of more green biological method to produce BDO gradually shows more advantages.At present,there are few researches on the hydrogenation of dimethyl succinic acid(DMS),which can be obtained from the esterification of succinic acid platform molecule,to BDO.Three inorganic materials of copper nitrate,zinc nitrate and aluminum nitrate,were selected to prepare the copper catalyst for the hydrogenation of dimethyl succinic acid(DMS) to 1,4-butanediol(BDO) by coprecipitate method.The products were characterized by XRF,BET,H2-TPR,XRD and XPS.And the catalytic material properties were tested in order to obtain catalytic materials with good performance,providing ideas for subsequent research.The results showed that the catalytic material with copper mass fraction of 20% and zinc-aluminum molar ratio of 0.3 had good hydrogenation performance at 185 ℃,5 MPa,hydrogen-ester ratio of 150 and space velocity of 1 h-1,with DMS conversion rate of 98.6% and BDO selectivity of 87.3%.And it had good stability after 1 000 h continuous operation which showed good industrial prospect.

Cite this article

WANG Peng , ZHAO Shanshan , LU Yanfei , LI Shisong , WANG Chunlei , SHU Chang , ZHANG Dongsheng . Study on preparation of copper-based materials and its catalytic performance for hydrogenation of dimethyl succinate[J]. Inorganic Chemicals Industry, 2023 , 55(10) : 145 -152 . DOI: 10.19964/j.issn.1006-4990.2022-0751

References

1 YIM H, HASELBECK R, NIU Wei,et al.Metabolic engineering of Escherichia coli for direct production of 1,4-butanediol[J].Nature Chemical Biology20117(7):445-452.
2 LIU Haolan, JIANG Yuanyuan, ZHAO Huaiyuan,et al.Preparation of highly dispersed Cu catalysts from hydrotalcite precursor for the dehydrogenation of 1,4-butanediol[J].Journal of Industrial and Engineering Chemistry2021102:251-259.
3 刘响,廖启江,张敏卿.1,4-丁炔二醇加氢过程研究进展[J].化工进展201736(8):2787-2797.
  LIU Xiang, LIAO Qijiang, ZHANG Minqing.Research progress of 1,4-butynediol hydrogenation process[J].Chemical Industry and Engineering Progress201736(8):2787-2797.
4 TAMURA M, NAKAGAWA Y, TOMISHIGE K.Recent developments of heterogeneous catalysts for hydrogenation of carboxylic acids to their corresponding alcohols[J].Asian Journal of Organic Chemistry20209(2):126-143.
5 黄佩佩.1,4-丁二醇的生产现状和发展[J].当代化工研究2022(1):48-50.
  HUANG Peipei.Production status and development of 1,4-butanediol[J].Modern Chemical Research2022(1):48-50.
6 BURGARD A, BURK M J, OSTERHOUT R,et al.Development of a commercial scale process for production of 1,4-butanediol from sugar[J].Current Opinion in Biotechnology201642:118-125.
7 李庆远,王超,许世佩,等.PBS前体1,4-丁二醇合成的反应工艺和催化剂研究进展[J].化工进展202241(11):5771-5782.
  LI Qingyuan, WANG Chao, XU Shipei,et al.Research progress on reaction process and catalysts for PBS precursor of 1,4-butanediol synthesis[J].Chemical Industry and Engineering Progress202241(11):5771-5782.
8 WU Mengying, SUNG L Y, LI H,et al.Combining CRISPR and CRISPRi systems for metabolic engineering of E.coli and 1,4-BDO biosynthesis[J].ACS Synthetic Biology20176(12):2350-2361.
9 LEE Y, KIM Y T, KWON E E,et al.Biochar as a catalytic material for the production of 1,4-butanediol and tetrahydrofuran from furan[J].Environmental Research2020184:109325.
10 FORTE A, ZUCARO A, BASOSI R,et al.LCA of 1,4-butanediol produced via direct fermentation of sugars from wheat straw feedstock within a territorial biorefinery[J].Materials20169(7):563.
11 GUO Hui, LIU Huan, JIN Yuhan,et al.Advances in research on the bio-production of 1,4-butanediol by the engineered microbes[J].Biochemical Engineering Journal2022185:108478.
12 SILVA R G C, FERREIRA T F, BORGES é R.Identification of potential technologies for 1,4-Butanediol production using prospecting methodology[J].Journal of Chemical Technology & Biotechnology202095(12):3057-3070.
13 BRANDS D S, POELS E K, BLIEK A.Ester hydrogenolysis over promoted Cu/SiO2 catalysts[J].Applied Catalysis A:General1999184(2):279-289.
14 ZHU Yulei, YANG Jun, DONG Genquan,et al.An environmentally benign route to γ-butyrolactone through the coupling of hydrogenation and dehydrogenation[J].Applied Catalysis B:Environmental200557(3):183-190.
15 DAKHEL A A.Creation of room-temperature DMS carbon-incorporated ZnO[J].Journal of Optoelectronics and Advanced Materials202123(1/2):58-62.
16 DAKHEL A A.Comparative study of the hydrogenation of Cu and TM(Mn,Fe,Ni)-codoped ZnO nanocomposite DMS[J].Journal of Superconductivity and Novel Magnetism201528(7):2039-2045.
17 EL-HILO M, DAKHEL A A, YACOOB Z J.Magnetic interactions in Co2+ doped ZnO synthesised by co-precipitation method:Efficient effect of hydrogenation on the long-range ferromagnetic order[J].Journal of Magnetism and Magnetic Materials2019482:125-134.
18 KANG K H, HAN S J, LEE J W,et al.Effect of boron content on 1,4-butanediol production by hydrogenation of succinic acid over Re-Ru/BMC (boron-modified mesoporous carbon) catalysts[J].Applied Catalysis A:General2016524:206-213.
19 YAO Yaqi, WU Xiaoqian, GUTIéRREZ O Y,et al.Roles of Cu+ and Cu0 sites in liquid-phase hydrogenation of esters on core-shell CuZn x @C catalysts[J].Applied Catalysis B:Environmental2020267:118698.
20 LIU Hanwen, HU Qi, FAN Guoli,et al.Surface synergistic effect in well-dispersed Cu/MgO catalysts for highly efficient vapor-phase hydrogenation of carbonyl compounds[J].Catalysis Science & Technology20155(8):3960-3969.
21 ZUO Jianliang, CHEN Zhihang, WANG Furong,et al.Low-temperature selective catalytic reduction of NO x with NH3 over novel Mn-Zr mixed oxide catalysts[J].Industrial & Engineering Chemistry Research201453(7):2647-2655.
22 郜宪龙,莫文龙,马凤云,等.助剂对Ni-Al合金和Raney-Ni催化剂结构及1,4-丁烯二醇加氢性能的影响[J].无机化学学报202036(5):958-968.
  GAO Xianlong, MO Wenlong, MA Fengyun,et al.Effect of promoter on the Ni-Al alloy & the corresponding Raney-Ni catalyst and hydrogenation performance of 1,4-butylenedioi[J].Chinese Journal of Inorganic Chemistry202036(5):958-968.
23 HU Qi, YANG Lan, FAN Guoli,et al.Hydrogenation of biomass-derived compounds containing a carbonyl group over a copper-based nanocatalyst:Insight into the origin and influence of surface oxygen vacancies[J].Journal of Catalysis2016340:184- 195.
24 王振宇.高附加值手性醇的不对称合成研究[D].北京:北京化工大学,2017.
  WANG Zhenyu.Study on asymmerty of high value chiral alcohols[D].Beijing:Beijing University of Chemical Technology,2017.
25 HONG U G, KIM J K, LEE J,et al.Conversion of succinic acid to 1,4-butanediol via dimethyl succinate over rhenium nano-catalyst supported on copper-containing mesoporous carbon[J].Journal of Nanoscience and Nanotechnology201414(11):8867-8872.
26 HUANG Xiumin, MA Meng, MIAO Shu,et al.Hydrogenation of methyl acetate to ethanol over a highly stable Cu/SiO2 catalyst:Reaction mechanism and structural evolution[J].Applied Catalysis A:General2017531:79-88.
27 WANG Yue, LIAO Junyu, ZHANG Jian,et al.Hydrogenation of methyl acetate to ethanol by Cu/ZnO catalyst encapsulated in SBA-15[J].AIChE Journal201763(7):2839-2849.
28 DI Xin, LI Chuang, LAFAYE G,et al.Influence of Re-M interactions in Re-M/C bimetallic catalysts prepared by a microwave-assisted thermolytic method on aqueous-phase hydrogenation of succinic acid[J].Catalysis Science & Technology20177(22):5212-5223.
29 VARDON D R, SETTLE A E, VOROTNIKOV V,et al.Ru-Sn/AC for the aqueous-phase reduction of succinic acid to 1,4-butanediol under continuous process conditions[J].ACS Catalysis20177(9):6207-6219.
30 KEELS J M, CHEN Xiao, KARAKALOS S,et al.Aqueous-phase hydrogenation of succinic acid using bimetallic Ir-Re/C catalysts prepared by strong electrostatic adsorption[J].ACS Catalysis20188(7):6486-6494.
31 OHLINGER C, KRAUSHAAR-CZARNETZKI B.Improved processing stability in the hydrogenation of dimethyl maleate to γ-butyrolactone,1,4-butanediol and tetrahydrofuran[J].Chemical Engineering Science200358(8):1453-1461.
32 STEIN J, KABASCI S.Hydrierung von diethylsuccinat zu γ-butyrolacton,1,4-butandiol und tetrahydrofuran[J].Chemie Ingenieur Technik201688(5):600-606.
33 DING Guoqiang, ZHU Yulei, ZHENG Hongyan,et al.Study on the reaction pathway in the vapor-phase hydrogenation of bioma-ss-derived diethyl succinate over CuO/ZnO catalyst[J].Catalysis Communications201011(14):1120-1124.
34 LE S D, NISHIMURA S.Highly selective synthesis of 1,4-butanediol via hydrogenation of succinic acid with supported Cu-Pd alloy nanoparticles[J].ACS Sustainable Chemistry & Engineering20197(22):18483-18492.
35 KANG K H, HONG U G, BANG Yongju,et al.Hydrogenation of succinic acid to 1,4-butanediol over Re-Ru bimetallic catalysts supported on mesoporous carbon[J].Applied Catalysis A:General2015490:153-162.
36 DI Xin, LI Chuang, ZHANG Bingsen,et al.Role of Re and Ru in Re-Ru/C bimetallic catalysts for the aqueous hydrogenation of succinic acid[J].Industrial & Engineering Chemistry Research201756(16):4672-4683.
37 TAKEDA Y, TAMURA M, NAKAGAWA Y,et al.Hydrogenation of dicarboxylic acids to diols over Re-Pd catalysts[J].Catalysis Science & Technology20166(14):5668-5683.
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