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Progress in Chemistry 2020, Vol. 32 Issue (2/3): 162-178 DOI: 10.7536/PC190711 Previous Articles   Next Articles

Special Issue: 电化学有机合成

Alcohol Amination for N-Alkyl Amine Synthesis with Heterogeneous Catalysts

Xinzhi Wang1,2, Hongli Wang1, Feng Shi1,**()   

  1. 1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
    2. University of Chinese Academy of Sciences, Beijing 100049, China
  • Received: Online: Published:
  • Contact: Feng Shi
  • About author:
    ** e-mail:
  • Supported by:
    National Natural Science Foundation of China(21633013)
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N-alkyl amines are an important class of molecules in the chemical industry and are extensively applied in the syntheses of dyes, pharmaceuticals, agrochemicals, surfactants, rubber ingredients, and functional materials. Given the importance of N-alkyl amines, the development of efficient synthetic methodologies to synthesize these amines is of broad interest. Among various methods, the catalytic alcohol amination has been viewed as effective and green method for synthesis of N-alkyl amines because alcohol is readily available, and water is generated as the sole by-product. This review describes developments and recent advances in the alcohol amination with different heterogeneous catalyst systems, including nickel, copper, palladium, platinum, cobalt, manganese, iron, gold, ruthenium, silver, and other catalyst systems. The frontiers and future of the topic are also given.

Key words: amine, alcohol, heterogeneous catalysis, alkylation
Scheme 1 The alcohol amination with borrowing hydrogen mechanism
Scheme 2 The N-alkylation of aniline and ethanol catalyzed by Ni[25]
Scheme 3 The N-alkylation of indole and secondary alcohol catalyzed by Raney Ni[30]
Scheme 4 N-alkylation of various aniline with various alcohols[31]
Fig.1 Ni precursor in presence of KOH, benzyl alcohol and aniline[31]
Fig.2 (a) XRD patterns of Ni/Al2O3 catalysts with different Ni loadings pre-reduced at 500 ℃.(b) Particle size distribution from TEM analysis.(c) TOF per surface Ni atom for N-alkylation of aniline with(○) 1-octanol or(▼) benzyl alcohol by Ni/θ-Al2O3 at 144 ℃ as a function of mean Ni particle size[32]
Scheme 5 Amination of various alcohols with NH3 catalyzed by Ni / A l 2 O 3 [ 33 ]
Scheme 6 The synthesis of primary amine from alcohol and ammonia catalyzed by NiCuFe O x [ 37 ]
Fig.3 TEM and HR-TEM images of NiCuFeO x (a),(b) before and (c),(d) after use. Scale bars: (a),(c) 50 nm; (b),(d) 2 nm[37]
Fig.4 XRD diffraction patterns of NiCuFe O x [ 37 ]
Scheme 7 N-acetonyl morpholine synthesis with amine and glycerol catalyzed by CuNiAl O x [ 38 ]
Scheme 8 Preparation of pyrazine by ethanolamine [40]
Scheme 9 The N-alkylation of aliphatic amines with aliphatic alcohols catalyzed by CuCr2 O 4 [ 41 ]
Scheme 10 The N-alkylation of dimethylamine with aliphatic alcohols catalyzed by CuO-Cr2O3-Si O 2 [ 43 ]
Fig.5 XPS spectra of CuLLM lines of Cu-ZnO-Al2O3 catalyst: (a) reduced at 500 ℃;(b) exposed to methanol for 10 min after reduction[50]
Scheme 11 The N-alkylation of benzylamine and aniline with benzyl alcohol catalyzed by CuAl-HT[53]
Scheme 12 The synthesis of asymmetrical tertiary amines catalyzed by Cu2Al3 O x [ 54 ]
Scheme 13 The synthesis of NMPD from BDO and MA catalyzed by 3%Cu-3%Ni/ZSM-5[62]
Fig.6 (a)XRD patterns of different catalysts;(b) H2-TPR curves of 3%Cu/ZSM-5, 3%Ni/ZSM-5 and 3%Cu-3%Ni/ZSM-5[62]
Scheme 14 The photocatalyzed N-alkylation of p-Cl-aniline with methanol [63]
Scheme 15 The N-alkylation of amine and alcohol catalyzed by copper powder[64]
Scheme 16 N-alkylation of benzyl alcohol with n-hexylamine[65]
Scheme 17 N-alkylation of aliphatic amines with benzyl alcohols catalyzed by Pd/AlO(OH) [66]
Fig.7 TEM image of Pd/MgO[67]
Scheme 18 One-pot synthesis of piperazine from 1,2-diamine and ethylene glycol catalyzed by Pd/MgO[67]
Scheme 19 N-alkylation of 2-methoxybenzyl alcohol with aniline[68]
Fig.8 Mechanism of palladium catalyzed N-alkylation of amines with alcohols[68]
Fig.9 Typical TEM image of Pd x /TiO2 catalysts and the size distributions of Pd particles on the respective catalysts[69]
Scheme 20 Synthesis of 4-chloro-N,N-dimethylaniline [70]
Scheme 21 N-alkylation of n-octanol and secondary amine using PdZn/Al2O3 catalyst[74]
Scheme 22 N-alkylation of 1-octanol with ammonia[75]
Scheme 23 N-alkylation of p-touidine and benzyl alcohol [76]
Fig.10 (a) XRD patterns of Pd@MIL-100(Fe), MIL-100(Fe), and calculated MIL-100(Fe);(b) XPS spectrum of Pd@MIL-100(Fe) in Pd 3d region;(c) TEM and (d) HRTEM images of Pd@MIL-100(Fe);(e) TEM and (f) HRTEM images of Pd/MIL-100(Fe)[76]
Fig.11 (a) TEM and (b) HRTEM images of Pd1Au1@MIL-100(Fe);(c) and (d) STEM-EDS mapping of Pd1Au1@MIL-100(Fe); (e) and (f) line-scanning profile across a PdAu nanocluster in Pd1Au1@MIL-100(Fe)[77]
Scheme 24 Synthesis of tertiary amines from piperidine and methanol [78,79]
Scheme 25 Synthesis of diamines from the reactions of diols and aniline[81,82]
Scheme 26 OABCO synthesis via aminocyclization of THFDM [83]
Scheme 27 N-alkylation of butanediamine and benzyl alcohol[84]
Scheme 28 N-alkylation of 1-phenylethan-1-amines and benzyl alcohol[85]
Scheme 29 N-alkylation of dibutylamine and benzyl alcohol catalyzed by Mn O 2 [ 87 ]
Scheme 30 N-alkylation of sulfonamide and benzyl alcohol catalyzed by Mn O 2 [ 89 ]
Scheme 31 N-alkylation of benzyl alcohol and aromatic heterocyclic amine catalyzed by Fe3 O 4 [ 90 ]
Scheme 32 Au-catalyzed N-alkylation of benzyl alcohol with aniline[94]
Fig.12 (a) HAADF-STEM images and(b) the size distributions of 2 wt% Au/Al-MIL53[94]
Scheme 33 N-alkylation of aniline with myrtenol catalyzed by Au/Zr O 2 [ 96 ]
Scheme 34 N-alkylation of amines with alcohols catalyzed by Au/TiO2-VS[101]
Fig.13 Representative TEM image and size distribution of (a) 0.5 wt% Au/TiO2-VS; (b) 0.5 wt% Au/TiO2-VS after three runs[101]
Scheme 35 Gold-catalysed alkylation of amine by alcohol[102]
Scheme 36 N-alkylation of aniline with primary alcohols catalyzed by Au/Ti O 2 [ 104 ]
Scheme 37 N-Alkylation of synergistic Cu-Au photocatalysis[105]
Fig.14 Representative BFTEM image of the mixed photocatalyst system after reaction for 20 h on a lacey carbon Cu grid(scale bar: 10 nm; ○Cu NPs and□Au NPs)[105]
Scheme 38 N-Alkylation of isopropylamine with benzyl alcohol catalyzed by Au/NiO[106]
Scheme 39 N-alkylation of aromatic amine with aromatic alcohol catalyzed by TTA-Au-NG[107]
Fig.15 SEM images of (a,b) NG and TEM images of(c,d) TTA-Au-NG[107]
Scheme 40 The N-alkylation of sulfonamides with alcohols[108]
Fig.16 TEM pictures of Ru/Fe3O4 (a) before and (b) after 5 runs[108]
Scheme 41 N-alkylation of heteroaromatic amines and benzyl alcohol[109]
Scheme 42 N-monoalkylation catalyzed by Ru(OH)3-Fe3 O 4 [ 111 ]
Scheme 43 N-alkylation of benzyl alcohol and aniline catalyzed by Ag/Al2 O 3 [ 115 ]
Fig.17 (a) Fourier transforms of Ag K-edge EXAFS for Ag foil and Cu0.95Ag0.05/Al2O3(Cu + Ag=10 wt%);(b) Ag K-edge XANES spectra;(c) The inverse Fourier transform of k3-weighted Ag K-edge EXAFS spectrum of(solid line) Cu0.95Ag0.05/Al2O3(Cu+Ag=10 wt%) and (·) its best fit derived from curve-fitting analysis[49]
Fig.18 (a) SEM and TEM images and selected-area electron diffraction patterns of Ag-Mo-22 catalyst;(b) XRD diffraction patterns of prepared catalysts[118]
Scheme 44 N-alkylation of benzyl alcohol and sulfonamide catalyzed by Ag6Mo10 O 33 [ 118 ]
Scheme 45 N-alkylation of aniline and ethanol catalyzed by silica gel[122]
Scheme 46 Carbon-catalyzed N-alkylation of amines with alcohols[124]
Fig.19 FT-IR spectra. FT-IR spectra of C-0 to C-5(a~f), 0.18 wt% Ni/C-1(g), 0.07 wt% Pd/C-1(h) and C-1 treated with oxygen and alcohol(a’: C-1; b’: C-1-O and C-1/KOH were treated with oxygen at 150 ℃ for 24 h; c’: C-1-O-R and C-1-O/KOH were treated with isopropanol at 150 ℃ for 24 h; d’:C-1-U and C-1 were reused for five runs in the coupling reaction of aniline and benzyl alcohol)[124]
Fig.20 SEM images of the carbon materials.(a) C-0,(b) C-1[124]
Scheme 47 Carbon-catalyzed N-alkylation of(E)-1,3-diphenylprop-2-en-1-ol with 4-methyl benzenesul-fonamide[125]
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