非均相金属催化剂催化醇类还原胺化合成伯胺的研究进展Advances in Primary Amine Synthesis by Reductive Amination of Alcohols Using Heterogeneous Metal Catalysts
刘迎新,舒慧敏,刘海燕,刘晓爽,曾茂,周阔,魏作君
摘要(Abstract):
综述了近年来非均相金属催化剂在醇与NH_3还原胺化制备伯胺体系中的应用研究,重点阐述了醇胺化(包括缩合胺化和还原胺化)的反应机理,以及还原胺化制备伯胺所需催化体系的研究进展。醇的脱氢步骤是醇与氨还原胺化制备伯胺反应中的速率控制步骤,不同金属组分由于对NH_3与有机胺的吸附能不同而导致脱氢活性不同。在醇还原胺化制备伯胺的体系中,开发适用于无氢气条件下氢转移胺化的非均相催化剂、选择合适的载体、开发生物质醇合成伯胺的催化技术具有广阔的前景。
关键词(KeyWords): 醇类物质;还原胺化;伯胺;非均相催化剂
基金项目(Foundation): 国家自然科学基金(21476211);; 浙江省自然科学基金(LY14B060003,LY18B060016)
作者(Author): 刘迎新,舒慧敏,刘海燕,刘晓爽,曾茂,周阔,魏作君
参考文献(References):
- [1]B?hn S,Imm S,Neubert L,et al.The catalytic amination of alcohols[J].Chem Cat Chem,2011,3(12):1853-1864.
- [2]Shen Q,Hartwig J F.Palladium-catalyzed coupling of ammonia and lithium amide with aryl halides[J].Journal of the American Chemical Society,2006,128(31):10028-10029.
- [3]Willis M C.Palladium-catalyzed coupling of ammonia and hydroxide with aryl halides:the direct synthesis of primary anilines and phenols[J].Angewandte Chemie International Edition,2007,46(19):3402-3404.
- [4]Laval S,Dayoub W,Favre-Reguillon A,et al.A mild and efficient method for the reduction of nitriles[J].Tetrahedron Letters,2009,50(50):7005-7007.
- [5]Liu Y X,Zhou K,Lu M,et al.Acidic/basic oxides-supported cobalt catalysts for one-pot synthesis of isophorone diamine from hydroamination of isophorone nitrile[J].Industrial&Engineering Chemistry Research,2015,54(37):9124-9132.
- [6]Yin B L,Hu T S,Wu Y L.Hydroamination of olefin in a special conjugated spiroketal enol ether system,diastereoselective synthesis of amino-containing tonghaosu analogs[J].Tetrahedron Letters,2004,45(9):2017-2021.
- [7]Klein H,Jackstell R,Kant M,et al.First catalytic hydroaminomethylation in supercritical ammonia[J].Chemical Engineering&Technology,2007,30(6):721-725.
- [8]Junge K,Wendt B,Shaikh N,et al.Iron-catalyzed selective reduction of nitroarenes to anilines using organosilanes[J].Chemical Communications,2010,46(10):1769-1771.
- [9]Lou X B,He L,Qian Y,et al.Highly chemo-and regioselective transfer reduction of aromatic nitro compounds using ammonium formate catalyzed by supported gold nanoparticles[J].Advanced Synthesis&Catalysis,2011,353(2-3):281-286.
- [10]Baiker A,Kijenski J.Catalytic synthesis of higher aliphatic amines from the corresponding alcohols[J].Catalysis Reviews-Science and Engineering,1985,27(4):653-697.
- [11]Hayes K S.Industrial processes for manufacturing amines[J].Applied Catalysis A:General,2001,221(1-2):187-195.
- [12]Wang T,Dong Z,Fu T,et al.Nickel embedded in N-doped porous carbon for the hydrogenation of nitrobenzene to p-aminophenol in sulphuric acid[J].Chemical Communications,2015,51(100):17712-17715.
- [13]Bassili V A,Baiker A.Catalytic amination of 1-methoxy-2-propanol over silica supported nickel:study of the influence of the reaction parameters[J].Applied Catalysis,1990,65(2):293-308.
- [14]Gunanathan C,Milstein D.Selective synthesis of primary amines directly from alcohols and ammonia[J].Angewandte Chemie International Edition,2008,47(45):8661-8664.
- [15]Imm S,Bahn S,Neubert L,et al.An efficient and general synthesis of primary amines by ruthenium-catalyzed amination of secondary alcohols with ammonia[J].Angewandte Chemie International Edition,2010,49(44):8126-8129.
- [16]Shimizu K,Kon K,Onodera W,et al.Heterogeneous Ni catalyst for direct synthesis of primary amines from alcohols and ammonia[J].ACS Catalysis,2013,3(1):112-117.
- [17]Kobayashi H,Ohta H,Fukuoka A.Conversion of lignocellulose into renewable chemicals by heterogeneous catalysis[J].Catalysis Science&Technology,2012,2(5):869-883.
- [18]Crews K,Reeves C,Thomas P,et al.Heterogeneous catalysis of C–O bond cleavage for cellulose deconstruction:a potential pathway for ethanol production[J].ISRN Nanotechnology,2014,2014:1-8.
- [19]Likhar P R,Arundhathi R,Kantam M L,et al.Amination of alcohols catalyzed by copper-aluminium hydrotalcite:a green synthesis of amines[J].European Journal of Organic Chemistry,2009,2009(31):5383-5389.
- [20]Veefkind V A,Lercher J A.Zeolite catalysts for the selective synthesis of mono-and diethylamines[J].Journal of Catalysis,1998,180(2):258-269.
- [21]Klyuev M V,Khidekel'M L.Catalytic amination of alcohols,aldehydes,and ketones[J].Russian Chemical Reviews,1980,49(1):14-27.
- [22]Sabatier P,Reid E E.Catalysis in organic chemistry[M].London:D.Van Nostrand Company,1922.
- [23]Segawa K,Ilao M C.Methanol amination over small-pore zeolite catalysts[J].Studies in Surface Science and Catalysis,1997,105:1219-1226.
- [24]Hu Z S,Wei L H,Chen S Y,et al.External modification of zeolite by metal surfactant for methanol amination[J].Microporous and Mesoporous Materials,1998,21(1-3):7-12.
- [25]Maeda N,Meemken F,Hungerbühler K,et al.Selectivity-controlling factors in catalytic methanol amination studied by isotopically modulated excitation IR spectroscopy[J].Acs Catalysis,2013,3(2):219–223.
- [26]Bui-The-Khai,Concilio C,Porzi G.A facile synthesis of symmetrical secondary amines from primary amines promoted by the homogeneous catalyst Ru Cl2(Ph3P)3[J].Journal of Organometallic Chemistry,1981,208(2):249-251.
- [27]Grigg R,Mitchell T R B,Sutthivaiyakit S,et al.Transition metal-catalysed N-alkylation of amines by alcohols[J].Journal of the Chemical Society,Chemical Communications,1981,12(12):611-612.
- [28]Fujita K I,Li Z Z,Ozeki N,et al.N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex[J].Tetrahedron Letters,2003,44(13):2687-2690.
- [29]Prades A,Corberán R,Poyatos M,et al.[Ir Cl2Cp*(NHC)]complexes as highly versatile efficient catalysts for the cross-coupling of alcohols and amines[J].Chemistry-A European Journal,2008,14(36):11474-11479.
- [30]Das K,Shibuya R,Nakahara Y,et al.Platinum-catalyzed direct amination of allylic alcohols with aqueous ammonia:selectivesynthesis of primary allylamines[J].Angewandte Chemie International Edition,2012,51(1):150-154.
- [31]Sewell G,O'Connor C,Steen E V.Reductive amination of ethanol with silica-supported cobalt and nickel catalysts[J].Applied Catalysis A:General,1995,125(1):99-112.
- [32]Ruiz D,Aho A,Saloranta T,et al.Direct amination of dodecanol with NH3 over heterogeneous catalysts.Catalyst screening and kinetic modelling[J].Chemical Engineering Journal,2017,307:739-749.
- [33]Guillena G,Ramón D J,Yus M.Alcohols as electrophiles in C-C bond-forming reactions:the hydrogen autotransfer process[J].Angewandte Chemie International Edition,2007,46(14):2358-2364.
- [34]Guillena G,Ramón D J,Yus M.Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles[J].Chemical Reviews,2010,110(3):1611-1641.
- [35]Dobereiner G E,Crabtree R H.Dehydrogenation as a substrate-activating strategy in homogeneous transition-metal catalysis[J].Chemical Reviews,2010,110(2):681-703.
- [36]Klinkenberg J L,Hartwig J F.Catalytic organometallic reactions of ammonia[J].Angewandte Chemie International Edition,2011,50(1):86-95.
- [37]Watanabe Y,Tsuji Y,Ohsugi Y.The ruthenium catalyzed N-alkylation and N-heterocyclization of aniline using alcohols and aldehydes[J].Tetrahedron Letters,1981,22(28):2667-2670.
- [38]Pridmore S J,Slatford P A,Daniel A,et al.Ruthenium-catalysed conversion of 1,4-alkynediols into pyrroles[J].Tetrahedron Letters,2007,48(29):5115-5120.
- [39]Defieber C,Ariger M A,Moriel P,et al.Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols:sulfamic acid as ammonia equivalent[J].Angewandte Chemie International Edition,2007,46(17):3139-3143.
- [40]Shimizu K.Heterogeneous catalysis for the direct synthesis of chemicals by borrowing hydrogen methodology[J].Catalysis Science&Technology,2015,5(3):1412-1427.
- [41]Fischer A,Mallat T,Baiker A.Amination of diols and polyols to acyclic amines[J].Catalysis Today,1997,37(2):167-189.
- [42]Schwoegler E J,Adkins H.Preparation of certain amines[J].Journal of American Chemical Society,1939,61(12):3499-3502.
- [43]Baiker A,Caprez W,Holstein W L.Catalytic amination of aliphatic alcohols in the gas and liquid phases:kinetics and reaction pathway[J].Industrial&Engineering Chemistry Product Research&Development,1983,22(2):217-225.
- [44]Kliger G A,Glebov L S,Shuikin A N,et al.Mechanism of amine formation in the amination of alcohols in the presence of metal catalysts[J].Russian Chemical Bulletin,1990,39(2):431.
- [45]Kliger G A,Shuikin A N,Glebov L S,et al.Mechanism of the hydroamination of alcohols and carbonyl compounds on a fused iron catalyst[J].Russian Chemical Bulletin,1990,39(8):1750-1753.
- [46]Bassili V A,Baiker A.Catalytic amination of 1-methoxypropan-2-ol over silica supported nickel:modelling of reaction kinetics[J].Applied Catalysis,1991,70(1):325-338.
- [47]Cho J H,Park J H,Chang T S,et al.Reductive amination of 2-propanol to monoisopropylamine over Ni/γ-Al2O3 catalysts[J].Catalysis Letters,2013,143(12):1319-1327.
- [48]Cho J H,Park J H,Chang T S,et al.Reductive amination of 2-propanol to monoisopropylamine over Co/γ-Al2O3 catalysts[J].Applied Catalysis A:General,2012,417-418:313-319.
- [49]Cui X J,Dai X C,Deng Y Q,et al.Development of a general non-noble metal catalyst for the benign amination of alcohols with amines and ammonia[J].Chemistry-A European Journal,2013,19(11):3665-3675.
- [50]Watson A J A,Williams J M J.The give and take of alcohol activation[J].Science,2010,329(5992):635-636.
- [51]Shimizu K,Kanno S,Kon K,et al.N-alkylation of ammonia and amines with alcohols catalyzed by Ni-loaded Ca Si O3[J].Catalysis Today,2014,232:134-138.
- [52]Sewell G S,O'Connor C T,Steen E V.Effect of activation procedure and support on the reductive amination of ethanol using supported cobalt catalysts[J].Journal of Catalysis,1997,167(2):513-521.
- [53]Zamlynny V,KubelkováL,Bab?rek E,et al.Amination of cyclohexanol over metallosilicate-based materials[J].Applied Catalysis A:General,1998,169(1):119-125.
- [54]Fischer A,Maciejewski M,Bürgi T,et al.Cobalt-catalyzed amination of 1,3-propanediol:effects of catalyst promotion and use of supercritical ammonia as solvent and reactant[J].Journal of Catalysis,1999,183(2):373-383.
- [55]Fischer A,Mallat T,Baiker A.Synthesis of 1,4-diaminocyclohexane in supercritical ammonia[J].Journal of Catalysis,1999,182(2):289-291.
- [56]Fischer A,Mallat T,Baiker A.Continuous amination of propanediols in supercritical ammonia[J].Angewandte Chemie International Edition,1999,38(3):351-354.
- [57]Fischer A,Mallat T,Baiker A.Nickel-catalyzed amination of 1,3-propanediols differently substituted at C2-position:influence of reactant structure on diamine production[J].Journal of Molecular Catalysis A:Chemical,1999,149(1-2):197-204.
- [58]Jenzer G,Mallat T,Baiker A.Cobalt-catalyzed amination of 1,3-cyclohexanediol and 2,4-pentanediol in supercritical ammonia[J].Catalysis Letters,1999,61(3-4):111-114.
- [59]Becker J,Niederer J P M,Keller M,et al.Amination of cyclohexanone and cyclohexanol/cyclohexanone in the presence of ammonia and hydrogen using copper or a group VIII metal supported on a carrier as the catalyst[J].Applied Catalysis A:General,2000,197(2):229-238.
- [60]Chary K V R,Seela K K,Naresh D,et al.Characterization and reductive amination of cyclohexanol and cyclohexanone over Cu/Zr O2 catalysts[J].Catalysis Communications,2008,9(1):75-81.
- [61]Zhang Y N,Zhang Y C,Feng C,et al.Amination of ethanol to acetonitrile over Ni-doped Co/γ-Al2O3 catalyst[J].Catalysis Communications,2009,10(10):1454-1458.
- [62]Zhao G L,Yu L,Yan X L,et al.The role of iron in the selective amination of 1,2-butanediol to 2-amino-1-butanol over Co-Ba-Fe/γ-Al2O3[J].Reaction Kinetics,Mechanisms and Catalysis,2010,100(2):449-457.
- [63]Takanashi T,Nakagawa Y,Tomishige K.Amination of alcohols with ammonia in water over Rh-In catalyst[J].Chemistry Letters,2014,43(6):822-824.
- [64]Takanashi T,Tamura M,Nakagawa Y,et al.Structure of catalytically active Rh-In bimetallic phase for amination of alcohols[J].RSC Advances,2014,4(54):28664-28672.
- [65]Cho J H,An S H,Chang T S,et al.Effect of an alumina phase on the reductive amination of 2-propanol to monoisopropylamine over Ni/Al2O3[J].Catalysis Letters,2016,146(4):811-819.
- [66]Hong E,Bang S,Cho J H,et al.Reductive amination of isopropanol to monoisopropylamine over Ni-Fe/γ-Al2O3 catalysts:synergetic effect of Ni-Fe alloy formation[J].Applied Catalysis A:General,2017,542:146-153.
- [67]Li Y,Cheng H Y,Zhang C,et al.Reductive amination of 1,6-hexanediol with Ru/Al2O3 catalyst in supercritical ammonia[J].Science China Chemistry,2017,60(7):920-926.
- [68]Niemeier J,Engel R V,Rose M.Is water a suitable solvent for the catalytic amination of alcohols?[J].Green Chemistry,2017,19:2839-2845.
- [69]Park J H,Hong E,An S H,et al.Reductive amination of ethanol to ethylamines over Ni/Al2O3 catalysts[J].Korean Journal of Chemical Engineering,2017,34(10):2610-2618.
- [70]LIU Ying-xin(刘迎新),ZHOU Kuo(周阔),LU Meng(卢蒙),et al.Synthesis of isophorone diamine and its reaction condition optimization(异佛尔酮二胺的合成及工艺优化)[J].Journal of Chemical Engineering of Chinese Universities(高校化学工程学报),2015,29(3):616-620.
- [71]Liu Y X,Zhou K,Shu H M,et al.Switchable synthesis of furfurylamine and tetrahydrofurfurylamine from furfural alcohol over Raney nickel[J].Catalysis Science&Technology,2017,7:4129-4135.