journal article·2020-08

Cu-MOF/Au–Pd composite catalyst: preparation and catalytic performance evaluation

Mingjun Zhong, Shizhen Zhang, Anwang Dong, Zhuyin Sui, Lijuan Feng, Qi Chen

Journal of Materials Science· Volume 55· Issue 24
Publisher page

Abstract

Heterogeneous metal–organic framework composites are widely used to catalyze the synthesis reaction of organic materials. Here, we report the use of a heterogeneous catalyst to catalyze the reaction of alcohols and amines to synthesize imines directly using a one-pot method. A low-dimensional Cu-MOF prepared by a simple surfactant-assisted method shows the morphology of nanorods. Cu-MOF nanorods provide an ideal support for preparing supported metal nanocatalysts. A reduction method was applied to immobilize the ultrafine noble metal Au and Pd nanoparticles on the surface of Cu-MOF nanorods to form a Cu-MOF/Au–Pd composite catalyst. Cu-MOF/Au–Pd catalyst is used to catalyze the reaction between alcohols and amines to form imines. Due to the synergy between different metal nanoparticles, it can effectively catalyze the reaction to form imines. In addition, Cu2+ in Cu-MOF/Au–Pd catalyst facilitates the adsorption of substances by excess electrons and promotes product formation. After 12 h of catalytic reaction, the yield of imine is as high as 95%.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Metal-Organic Frameworks: Synthesis and Applications · Catalysis and Hydrodesulfurization Studies · Nanomaterials for catalytic reactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (62)

Show source-provided references
1. Sheberla D, Bachman JC, Elias JS, Sun CJ, Shao Horn Y, Dincă M (2017) Conductive MOF electrodes for stable supercapacitors with high areal capacitance. Nat Mater 16(2):220–22410.1038/nmat4766 ↗
2. Rubio Martinez M, Avci Camur C, Thornton AW, Imaz I, Maspoch D, Hill MR (2017) New synthetic routes towards MOF production at scale. Chem Soc Rev 46(11):3453–348010.1039/C7CS00109F ↗
3. Zheng B, Wang H, Wang Z, Ozaki N, Hang C, Luo X, Huang L, Zeng W, Yang M, Duan J (2016) A highly porous rht-type acylamide-functionalized metal–organic framework exhibiting large CO2 uptake capabilities. Chem Commun 52(88):12988–1299110.1039/C6CC06734D ↗
4. Wang Z, Luo X, Zheng B, Huang L, Hang C, Jiao Y, Cao X, Zeng W, Yun R (2018) Highly selective carbon dioxide capture and cooperative catalysis of a water-stable acylamide-functionalized metal-organic framework. Eur J Inorg Chem 11:1309–131410.1002/ejic.201701404 ↗
5. Wang S, Ye B, An C, Wang J, Li Q (2019) Synergistic effects between Cu metal–organic framework (Cu-MOF) and carbon nanomaterials for the catalyzation of the thermal decomposition of ammonium perchlorate (AP). J Mater Sci 54(6):4928–4941. https://doi.org/10.1007/s10853-018-03219-410.1007/s10853-018-03219-4 ↗
6. Yun R, Cui R, Qian F, Cao X, Luo S, Zheng B (2015) Formation of a metal–organic framework with high gas uptakes based upon amino-decorated polyhedral cages. RSC Adv 5(4):2374–237710.1039/C4RA14607G ↗
7. Ding M, Flaig RW, Jiang HL, Yaghi OM (2019) Carbon capture and conversion using metal–organic frameworks and MOF-based materials. Chem Soc Rev 48(10):2783–282810.1039/C8CS00829A ↗
8. Zou JY, Li L, You SY, Liu YW, Cui HM, Cui JZ, Zhang SW (2018) Two luminescent lanthanide (III) metal–organic frameworks as chemosensors for high-efficiency recognition of Cr (VI) anions in aqueous solution. Dalton Trans 47(44):15694–1570210.1039/C8DT03050B ↗
9. Ning S, Chen H, Zhang S, Cheng P (2018) A 2D water-stable metal–organic framework for fluorescent detection of nitroaromatics. Polyhedron 155:457–46310.1016/j.poly.2018.09.001 ↗
10. Zhu W, Xiang G, Shang J, Guo J, Motevalli B, Durfee P, Agola JO, Coker EN, Brinker CJ (2018) Versatile surface functionalization of metal-organic frameworks through direct metal coordination with a phenolic lipid enables diverse applications. Adv Funct Mater 28(16):170527410.1002/adfm.201705274 ↗
11. Zhao X, Zhang S, Yan J, Li L, Wu G, Shi W, Yang G, Guan N, Cheng P (2018) Polyoxometalate-based metal–organic frameworks as visible-light-induced photocatalysts. Inorg Chem 57(9):5030–503710.1021/acs.inorgchem.8b00098 ↗
12. Li G, Liu Q, Xia B, Huang J, Li S, Guan Y, Zhou H, Liao B, Zhou Z, Liu B (2017) Synthesis of stable metal-containing porous organic polymers for gas storage. Eur Polym J 91:242–24710.1016/j.eurpolymj.2017.03.014 ↗
13. Chen L, Ding X, Huo J, El Hankari S, Bradshaw D (2019) Facile synthesis of magnetic macroporous polymer/MOF composites as separable catalysts. J Mater Sci 54(1):370–382. https://doi.org/10.1007/s10853-018-2835-x10.1007/s10853-018-2835-x ↗
14. Zheng B, Huang L, Cao X, Shen S, Cao H, Hang C, Zeng W, Wang Z (2018) A highly porous acylamide decorated MOF-505 analogue exhibiting high and selective CO2 gas uptake capability. Cryst Eng Comm 20(13):1874–188110.1039/C8CE00103K ↗
15. Gou L, Ma L, Zhao MJ, Liu PG, Wang XD, Fan X, Li DL (2019) Co-based metal–organic framework and its derivatives as high-performance anode materials for lithium-ion batteries. J Mater Sci 54(2):1529–1538. https://doi.org/10.1007/s10853-018-2892-110.1007/s10853-018-2892-1 ↗
16. Chen L, Luque R, Li Y (2017) Controllable design of tunable nanostructures inside metal–organic frameworks. Chem Soc Rev 46(15):4614–463010.1039/C6CS00537C ↗
17. Shen K, Zhang L, Chen X, Liu L, Zhang D, Han Y, Chen J, Long J, Luque R, Li Y (2018) Ordered macro-microporous metal-organic framework single crystals. Science 359(6372):206–21010.1126/science.aao3403 ↗
18. Zhan G, Hua CZ (2015) General strategy for preparation of carbon-nanotube-supported nanocatalysts with hollow cavities and mesoporous shells. Chem Mater 27(3):726–73410.1021/cm504050x ↗
19. Wu HB, Lou XW (2017) Metal-organic frameworks and their derived materials for electrochemical energy storage and conversion: promises and challenges. Sci Adv 3(12):eaap925210.1126/sciadv.aap9252 ↗
20. Dong SY, Peng L, Wei WB, Huang TL (2018) Three MOFs-templated carbon nanocomposites for potential platforms of enzyme immobilization with improved electrochemical performance. ACS Appl Mater Interfaces 10(17):14665–1467210.1021/acsami.8b00702 ↗
21. Gotthardt MA, Schoch R, Wolf S, Bauer M, Kleist W (2015) Synthesis and characterization of bimetallic metal–organic framework Cu–Ru-BTC with HKUST-1 structure. Dalton Trans 44(5):2052–205610.1039/C4DT02491E ↗
22. Li Y, Hu J, Ma D, Zheng Y, Chen M, Wan H (2018) Disclosure of the surface composition of TiO2-supported gold-palladium bimetallic catalysts by high-sensitivity low-energy ion scattering spectroscopy. ACS Catal 8(3):1790–179510.1021/acscatal.7b03839 ↗
23. Khan SA, Arshad T, Faisal M, Shah Z, Shaheen K, Suo H, Asiri AM, Akhtar K, Khan SB (2019) Al–Sr metal oxides and Al–Cd layered double hydroxides for the removal of Acridine orange dye in visible light exposure. J Mater Sci Mater Electron 30(16):15299–1531210.1007/s10854-019-01903-y ↗
24. Huda M, Minamisawa K, Tsukamoto T, Tanabe M, Yamamoto K (2019) Aerobic toluene oxidation catalyzed by subnano metal particles. Angew Chem Int Ed 58(4):1002–100610.1002/anie.201809530 ↗
25. Kim H, Moon HS, Sohail M, Yoon YN, Shah SFA, Yim K, Moon JH, Park YC (2019) Synthesis of cyclic carbonate by CO2 fixation to epoxides using interpenetrated MOF-5/n-Bu4NBr. J Mater Sci 54(18):11796–11803. https://doi.org/10.1007/s10853-019-03702-610.1007/s10853-019-03702-6 ↗
26. Hoseini SJ, Bahrami M, Sadri N, Aramesh N, Fard ZS, Iran HR, Agahi BH, Maddahfar M, Dehghani M, Arabi AZB (2018) Multi-metal nanomaterials obtained from oil/water interface as effective catalysts in reduction of 4-nitrophenol. J Colloid Interface Sci 513(1):602–61610.1016/j.jcis.2017.11.068 ↗
27. Mai HD, Rafiq K, Yoo H (2017) Nano metal-organic framework-derived inorganic hybrid nanomaterials: synthetic strategies and applications. Chem Eur J 23(24):5631–565110.1002/chem.201604703 ↗
28. Zhang Y, Yi Q, Deng Z, Zhou X, Nie H (2018) Excellent electroactivity of ternary Pd–Ag–Sn nanocatalysts for ethanol oxidation. Catal Lett 148(4):1190–120110.1007/s10562-018-2335-2 ↗
29. Zheng B, Luo X, Wang Z, Zhang S, Yun R, Huang L, Zeng W, Liu W (2018) An unprecedented water stable acylamide-functionalized metal–organic framework for highly efficient CH2/CO2 gas storage/separation and acid–base cooperative catalytic activity. Inorg Chem Front 5(9):2355–236310.1039/C8QI00662H ↗
30. Falcaro P, Ricco R, Yazdi A, Imaz I, Furukawa S, Maspoch D, Ameloot R, Evans JD, Doonan CJ (2016) Application of metal and metal oxide nanoparticles@ MOFs. Coord Chem Rev 307(2):237–25410.1016/j.ccr.2015.08.002 ↗
31. Gao T, Dong BX, Sun Y, Liu WL, Teng YL (2019) Fabrication of a water-stable luminescent MOF with an open Lewis basic triazolyl group for the high-performance sensing of acetone and Fe3+ ions. J Mater Sci 54(15):10644–10655. https://doi.org/10.1007/s10853-019-03638-x10.1007/s10853-019-03638-x ↗
32. Xu C, Fang R, Luque R, Chen L, Li Y (2019) Functional metal–organic frameworks for catalytic applications. Coord Chem Rev 388(1):268–29210.1016/j.ccr.2019.03.005 ↗
33. Cohen SM (2017) The postsynthetic renaissance in porous solids. J Am Chem Soc 139(8):2855–286310.1021/jacs.6b11259 ↗
34. Lu SL, Hu YM, Wan S, McCaffrey R, Jin YH, Gu HW, Zhang W (2017) Synthesis of ultrafine and highly dispersed metal nanoparticles confined in a thioether-containing covalent organic framework and their catalytic applications. J Am Chem Soc 139(47):17082–1708810.1021/jacs.7b07918 ↗
35. Shang TY, Lu LH, Cao Z, Liu Y, He WM, Yu B (2019) Recent advances of 1, 2, 3, 5-tetrakis (carbazol-9-yl)-4, 6-dicyanobenzene (4CzIPN) in photocatalytic transformations. Chem Commun 55(38):5408–541910.1039/C9CC01047E ↗
36. Pitzer L, Schwarz JL, Glorius F (2019) Reductive radical-polar crossover: traditional electrophiles in modern radical reactions. Chem Sci 10(36):8285–829110.1039/C9SC03359A ↗
37. Wang T, Ibañez J, Wang K, Fang L, Sabbe M, Michel C, Paul S, Pera Titus M, Sautet P (2019) Rational design of selective metal catalysts for alcohol amination with ammonia. Nat Catal 2(9):773–77910.1038/s41929-019-0327-2 ↗
38. Biswas S, Dutta B, Mullick K, Kuo CH, Poyraz AS, Suib SL (2015) Aerobic oxidation of amines to imines by cesium-promoted mesoporous manganese oxide. ACS Catal 5(7):4394–440310.1021/acscatal.5b00325 ↗
39. Cao X, Cui L, Liu B, Liu Y, Jia D, Yang W, Razal JM, Liu J (2019) Reverse synthesis of star anise-like cobalt doped Cu-MOF/Cu2+1O hybrid materials based on a Cu(OH)2 precursor for high performance supercapacitors. J Mater Chem A 7(8):3815–382710.1039/C8TA11396C ↗
40. Ramaraj S, Sakthivel M, Chen SM, Ho KC (2019) Active-site-rich 1T-phase CoMoSe2 integrated graphene oxide nanocomposite as an efficient electrocatalyst for electrochemical Sensor and energy storage applications. Anal Chem 13(91):8358–836510.1021/acs.analchem.9b01152 ↗
41. Samanta P, Desai AV, Sharma S, Chandra P, Ghosh SK (2018) Selective recognition of Hg2+ ion in water by a functionalized metal–organic framework (MOF) based chemodosimeter. Inorg Chem 57(5):2360–236410.1021/acs.inorgchem.7b02426 ↗
42. Sankar M, He Q, Dawson S, Nowicka E, Lu L, Bruijnincx PC, Beale AM, Kiely CJ, Weckhuysen BM (2016) Supported bimetallic nano-alloys as highly active catalysts for the one-pot tandem synthesis of imines and secondary amines from nitrobenzene and alcohols. Catal Sci Technol 6(14):5473–548210.1039/C6CY00425C ↗
43. Shim SY, Choi Y, Ryu DH (2018) Asymmetric synthesis of cyclobutanone via lewis acid catalyzed tandem cyclopropanation/semipinacol rearrangement. J Am Ceram Soc 140(36):11184–11188
44. Zhao YH, Luo Y, Zhu Y, Wang H, Zhou H, Tan H, Zhou Z, Ma YC, Xie W, Tang Z (2018) Synthesis of potential anticancer 1-(1H-Indol-3-yl) isoquinolines by silver nitrate mediated tandem reactions of 2-alkynylbenzaldehyde azines and indoles. Synlett 29(06):773–77810.1055/s-0036-1591743 ↗
45. Gong W, Chen X, Jiang H, Chu D, Cui Y, Liu Y (2019) Highly stable Zr(IV)-based metal-organic frameworks with chiral phosphoric acids for catalytic asymmetric tandem reactions. J Am Chem Soc 141(18):7498–750810.1021/jacs.9b02294 ↗
46. Shen R, Zhu W, Yan X, Li T, Liu Y, Li Y, Dai S, Gu ZG (2019) A porphyrin porous organic polymer with bicatalytic sites for highly efficient one-pot tandem catalysis. Chem Commun 55(6):822–82510.1039/C8CC08918C ↗
47. Wu S, Sun W, Chen J, Zhao J, Cao Q, Fang W, Zhao Q (2019) Efficient imine synthesis from oxidative coupling of alcohols and amines under air atmosphere catalysed by Zn-doped Al2O3 supported Au nanoparticles. J Catal 377:110–12110.1016/j.jcat.2019.07.027 ↗
48. Chen B, Wang L, Gao S (2015) Recent advances in aerobic oxidation of alcohols and amines to imines. ACS Catal 5(10):5851–587610.1021/acscatal.5b01479 ↗
49. Zhang M, Wu S, Bian L, Cao Q, Fang W (2019) One-pot synthesis of Pd-promoted Ce–Ni mixed oxides as efficient catalysts for imine production from the direct N-alkylation of amine with alcohol. Catal Sci Technol 9(2):286–30110.1039/C8CY01857J ↗
50. Geng L, Jian W, Jing P, Zhang W, Yan W, Bai FQ, Liu G (2019) Crystal phase effect of iron oxides on the aerobic oxidative coupling of alcohols and amines under mild conditions: a combined experimental and theoretical study. J Catal 377:145–15210.1016/j.jcat.2019.06.018 ↗
51. Reddy PL, Deshmukh K, Chidambaram K, Ali MMN, Sadasivuni KK, Kumar YR, Lakshmipathy R, Pasha SK (2019) Dielectric properties of polyvinyl alcohol (PVA) nanocomposites filled with green synthesized zinc sulphide (ZnS) nanoparticles. J Mater Sci Mater Electron 30(5):4676–468710.1007/s10854-019-00761-y ↗
52. Zhu L, Wang LS, Li B, Li W, Fu B (2016) Methylation of aromatic amines and imines using formic acid over a heterogeneous Pt/C catalyst. Catal Sci Technol 6(16):6172–617610.1039/C6CY00674D ↗
53. Furukawa S, Suzuki R, Komatsu T (2016) Selective activation of alcohols in the presence of reactive amines over intermetallic PdZn: efficient catalysis for alcohol-based N-alkylation of various amines. ACS Catal 6(9):5946–595310.1021/acscatal.6b01677 ↗
54. Serna P, Corma A (2015) Transforming nano metal nonselective particulates into chemoselective catalysts for hydrogenation of substituted nitrobenzenes. ACS Catal 5(12):7114–712110.1021/acscatal.5b01846 ↗
55. Chen X, Liu K, Zhang ZZ, Wang CR, Li BH, Zhao HF, Zhao DX, Shen DZ (2016) Self-powered solar-blind photodetector with fast response based on Au/β-G2O3 nanowires array film schottky junction. ACS Appl Mater Interfaces 8(6):4185–419110.1021/acsami.5b11956 ↗
56. Tamura M, Tomishige K (2015) Redox properties of CeO2 at low temperature: the direct synthesis of imines from alcohol and amine. Angew Chem Int Ed 54(3):864–86710.1002/anie.201409601 ↗
57. Zhu P, Zhang J, Wang J, Kong P, Wang Y, Zheng Z (2019) Photocatalytic selective aerobic oxidation of amines to nitriles over Ru/γ-Al2O3: the role of support surface and the strong imine intermediate adsorption. Catal Sci Technol 22(9):2356–2362
58. Quadri SAI, Das TC, Jadhav S, Farooqui M (2018) Efficient synthesis of tertiary amine by direct N-alkylation of secondary amine with carboxylic acid using Ni(0) encat catalyst. Synth Commun 48(3):267–27710.1080/00397911.2017.1396613 ↗
59. Le NT, Byun A, Han Y, Lee KI, Kim H (2015) Preparation of 2, 5-bis (aminomethyl) furan by direct reductive amination of 2, 5-diformylfuran over nickel-raney catalysts. Green Sustain Chem 5(03):115–12710.4236/gsc.2015.53015 ↗
60. Pan C, Gu H, Dong L (2016) Synthesis and electrochemical performance of polyaniline@MnO2/graphene ternary composites for electrochemical supercapacitors. J Power Sources 303(30):175–18110.1016/j.jpowsour.2015.11.002 ↗
61. Zhang W, Xiao Z, Wang J, Fu W, Tan R, Yin D (2019) Selective aerobic oxidation of alcohols over gold-palladium alloy catalysts using air at atmospheric pressure in water. ChemCatChem 11(6):1779–178810.1002/cctc.201900015 ↗
62. Deng C, Li Y, Sun W, Liu F, Zhang Y, Qian H (2019) Supported AuPd nanoparticles with high catalytic activity and excellent separability based on the magnetic polymer carriers. J Mater Sci 54(17):11435–11447. https://doi.org/10.1007/s10853-019-03701-710.1007/s10853-019-03701-7 ↗