醋酸(甲酯)与甲醛羟醛缩合生成丙烯酸(甲酯)催化剂的研究进展
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摘要
综述了醋酸(甲酯)与甲醛羟醛缩合生成丙烯酸(甲酯)路线所用的催化剂,主要包括V-P-O、碱金属/碱土金属型、离子液体类型催化剂的结构特性、催化性能等方面的最新研究进展,认为开发新型催化剂是该工艺路线的核心技术。
This paper supplies an overview of latest progress in structural features and catalytic performance of the catalysts for aldol condensation reaction between acetic acid(methyl acetate) and formaldehyde to synthesize acrylic acid(methyl acylate),mainly including V-P-O,alkali metal/alkaline earth metals and ionic liquids catalysts.It is pointed out that the development of new type catalysts is the core technology for the synthesis of acrylic acid(methyl acylate) via aldol condensation route.
This paper supplies an overview of latest progress in structural features and catalytic performance of the catalysts for aldol condensation reaction between acetic acid(methyl acetate) and formaldehyde to synthesize acrylic acid(methyl acylate),mainly including V-P-O,alkali metal/alkaline earth metals and ionic liquids catalysts.It is pointed out that the development of new type catalysts is the core technology for the synthesis of acrylic acid(methyl acylate) via aldol condensation route.
引文
[1]郑承旺.2005年中国丙烯酸行业发展概况[J].丙烯酸化工及应用,2006,(1):1-12.
[2]Pu Y J,Yu Y L,Zhu X X.Progress in research of catalyst for propane oxidation to acrylic acid[J].Petrochemical Technology&Application,2014,32(3):270-274.
[3]孙彦民,李贺,曾贤君,等.合成丙烯酸催化剂研究进展[J].工业催化,2016,24(8):12-19.
[4]朱桂生,邵守言,黄诚,等.丙烯酸(酯)生产现状与醋酸甲醛羟醛缩合制备丙烯酸研究进展[J].安徽化工,2017,43(2):15-19.
[5]胡靖,殷恒波.丙烯酸市场状况及其生产技术状况[J].乙醛醋酸化工,2016,(4):4-11.
[6]陈晓华,毛震波,张华西,等.醋酸甲醛法制丙烯酸技术进展[J].乙醛醋酸化工,2017,(11):4-7.
[7]Tanner K,Gill E,Wells R.Aldol consensation reactions of acetone and formaldehyde over vanadium phosphate catalysts:Comments on the acid-base properties[J].Physical Chemistry Chemical Physics,2002,4:688-695.
[8]Ai M.Formation of methyl methacrylate by condensation of methyl propionate with formaldehyde over silica-supported cesium hydroxide catalysts[J].Applied Catalysis A,2005,288:211-215.
[9]Feng X Z,Sun B,Yao Y,et al.Renewable production of acrylic acid and its derivative:New insights into the aldol condensation route over the vanadium phosphorus oxides[J]. Journal of Catalysis,2014,314:132-141.
[10]Wang A,Hu J,Yin H,et al.Aldol condensation of acetic acid with formaldehyde to acrylic acid over Cs(Ce,Nd)VPO/SiO2catalyst[J].RSC Advances,2017,7:48475-48485.
[11]Yang D,Sararuk C,Suzuki K,et al.Effect of calcination temperature on the catalytic activity of VPO for aldol condensation of acetic acid and formalin[J]. Chemical Engineering Journal,2016,300:160-168.
[12]Herrmann J M,Vernoux P,Bere K E.In situ study of redox and of p-type semiconducting properties of vanadyl pyrophosphate and of V-P-O catalysts during the partial oxidation of n-butane to maleic anhydride[J].Journal of Catalysis,1997,167(1):106-117.
[13]Ai M.Vapor-phase aldol condensation of formaldehyde with acetic acid on V2O5-P2O5Catalysts[J]. Journal of Catalysis,1987,107:201-208.
[14]Yang D,Li D,Yao H Y,et al.Reaction of formalin with acetic acid over vanadium-phosphorus oxide bifunctional catalyst[J].Industrial&Engineering Chemistry Research,2015,54:6865-6873.
[15]Guo X P,Yang D,Zuo C C,et al.Catalysts,process optimization,and kinetics for the production of methyl acrylate over vanadium phosphorus oxide catalysts[J]. Industrial&Engineering Chemistry Research,2017,56:5860-5871.
[16]Hu J,Lu Z,Yin H,et al. Aldol condensation of acetic acid with formaldehyde to acrylic acid over SiO2-,SBA-15-,and HZSM-5-supported V-P-O catalysts[J]. Journal of Industrial and Engineering Chemistry,2016,40:145-151.
[17]Zhao H,Zuo C C,Yang D,et al. Effects of support for vanadium phosphorus oxide catalysts on vapor-Phase aldol condensation of methyl acetate with formaldehyde[J]. Industrial&Engineering Chemistry Research,2016,55:12693-12702.
[18]Wang F,Dubois J L,Ueda W.Catalytic dehydration of glycerol over vanadium phosphate oxides in the presence of molecular oxygen[J].Journal of Catalysis,2009,268:260-267.
[19]Wang X H,Nie W Y,Ji W J,et al. A good performance VPO catalyst for partial oxidation of n-butane to maleic anhydride[J].Chemistry Letters,2001,30(7):696-697.
[20]Vitcha J F,Sims V A.Vapor phase aldol reaction-acrylic acid by reaction of acetic acid and formaldehyde[J].Industrial&Engineering Chemistry Product Research and Development,1966,5:50-53.
[21]荆涛,田景芝,郑永杰,等.二步法合成笼状大孔/介孔三维有序Cs2O-Sb2O5/SiO2[J].黑龙江大学自然科学学报,2011,28(2):213-217.
[22]Wang Y,Lang X,Zhao G,et al.Preparation of Cs-La-Sb/Si O2catalyst and its performance for the synthesis of methyl acrylate by aldol condensation[J].RSC Advances,2015,5:32826-32834.
[23]Jiang S F,Li C S,Chen H N,et al.One-step synthesis of methyl acrylate using methyl acetate with formaldehyde in a fluidized bed reactor[J]. Industrial&Engineering Chemsitry Research,2017,56:9322-9330.
[24]Zhang G L,Zhang H H,Yang D,et al. Catalysts,kinetics and process optimization for the synthesis of methyl acrylate over Cs-P/γ-Al2O3[J].Catalysis Science&Technology,2016,6:6417-6430.
[25]Bao Q,Bu T,Yan J,et al.Synthesis of methyl acrylate by aldol condensation of methyl acetate with formaldehyde over Al2O3-supported barium catalyst[J]. Catalysis Letters,2017,147:1540-1550.
[26]Bao Q,Zhu W,Yan J,et al. Vapor phase aldol condensation of methyl acetate with formaldehyde over a Ba-La/Al2O3catalyst:The stabilizing role of La and effect of acid-base properties[J].RSC Advances,2017,7:52304-52311.
[27]Wang G,Wang H,Li C S,et al.One-step and in-situ catalytic synthesis of acrylates from acetates(or propionates)and trioxane at room temperature[J].Journal of Industrial and Engineering Chemistry,2017,55:173-182.
[28]Wang G,Li Z X,Li C S,et al.Kinetic and thermodynamic studies on one-step synthesis of methyl acrylate promoted by generated ionic liquid at mild temperature[J].Chemical Engineering Journal,2017,319:297-306.
[29]Wang G,Sararuk C,Li Z X,et al.Studies on mild catalytic synthesis of methyl acrylate via one-step aldol reaction[J]. AIChE Journal,2018,64(4):1359-1372.
[2]Pu Y J,Yu Y L,Zhu X X.Progress in research of catalyst for propane oxidation to acrylic acid[J].Petrochemical Technology&Application,2014,32(3):270-274.
[3]孙彦民,李贺,曾贤君,等.合成丙烯酸催化剂研究进展[J].工业催化,2016,24(8):12-19.
[4]朱桂生,邵守言,黄诚,等.丙烯酸(酯)生产现状与醋酸甲醛羟醛缩合制备丙烯酸研究进展[J].安徽化工,2017,43(2):15-19.
[5]胡靖,殷恒波.丙烯酸市场状况及其生产技术状况[J].乙醛醋酸化工,2016,(4):4-11.
[6]陈晓华,毛震波,张华西,等.醋酸甲醛法制丙烯酸技术进展[J].乙醛醋酸化工,2017,(11):4-7.
[7]Tanner K,Gill E,Wells R.Aldol consensation reactions of acetone and formaldehyde over vanadium phosphate catalysts:Comments on the acid-base properties[J].Physical Chemistry Chemical Physics,2002,4:688-695.
[8]Ai M.Formation of methyl methacrylate by condensation of methyl propionate with formaldehyde over silica-supported cesium hydroxide catalysts[J].Applied Catalysis A,2005,288:211-215.
[9]Feng X Z,Sun B,Yao Y,et al.Renewable production of acrylic acid and its derivative:New insights into the aldol condensation route over the vanadium phosphorus oxides[J]. Journal of Catalysis,2014,314:132-141.
[10]Wang A,Hu J,Yin H,et al.Aldol condensation of acetic acid with formaldehyde to acrylic acid over Cs(Ce,Nd)VPO/SiO2catalyst[J].RSC Advances,2017,7:48475-48485.
[11]Yang D,Sararuk C,Suzuki K,et al.Effect of calcination temperature on the catalytic activity of VPO for aldol condensation of acetic acid and formalin[J]. Chemical Engineering Journal,2016,300:160-168.
[12]Herrmann J M,Vernoux P,Bere K E.In situ study of redox and of p-type semiconducting properties of vanadyl pyrophosphate and of V-P-O catalysts during the partial oxidation of n-butane to maleic anhydride[J].Journal of Catalysis,1997,167(1):106-117.
[13]Ai M.Vapor-phase aldol condensation of formaldehyde with acetic acid on V2O5-P2O5Catalysts[J]. Journal of Catalysis,1987,107:201-208.
[14]Yang D,Li D,Yao H Y,et al.Reaction of formalin with acetic acid over vanadium-phosphorus oxide bifunctional catalyst[J].Industrial&Engineering Chemistry Research,2015,54:6865-6873.
[15]Guo X P,Yang D,Zuo C C,et al.Catalysts,process optimization,and kinetics for the production of methyl acrylate over vanadium phosphorus oxide catalysts[J]. Industrial&Engineering Chemistry Research,2017,56:5860-5871.
[16]Hu J,Lu Z,Yin H,et al. Aldol condensation of acetic acid with formaldehyde to acrylic acid over SiO2-,SBA-15-,and HZSM-5-supported V-P-O catalysts[J]. Journal of Industrial and Engineering Chemistry,2016,40:145-151.
[17]Zhao H,Zuo C C,Yang D,et al. Effects of support for vanadium phosphorus oxide catalysts on vapor-Phase aldol condensation of methyl acetate with formaldehyde[J]. Industrial&Engineering Chemistry Research,2016,55:12693-12702.
[18]Wang F,Dubois J L,Ueda W.Catalytic dehydration of glycerol over vanadium phosphate oxides in the presence of molecular oxygen[J].Journal of Catalysis,2009,268:260-267.
[19]Wang X H,Nie W Y,Ji W J,et al. A good performance VPO catalyst for partial oxidation of n-butane to maleic anhydride[J].Chemistry Letters,2001,30(7):696-697.
[20]Vitcha J F,Sims V A.Vapor phase aldol reaction-acrylic acid by reaction of acetic acid and formaldehyde[J].Industrial&Engineering Chemistry Product Research and Development,1966,5:50-53.
[21]荆涛,田景芝,郑永杰,等.二步法合成笼状大孔/介孔三维有序Cs2O-Sb2O5/SiO2[J].黑龙江大学自然科学学报,2011,28(2):213-217.
[22]Wang Y,Lang X,Zhao G,et al.Preparation of Cs-La-Sb/Si O2catalyst and its performance for the synthesis of methyl acrylate by aldol condensation[J].RSC Advances,2015,5:32826-32834.
[23]Jiang S F,Li C S,Chen H N,et al.One-step synthesis of methyl acrylate using methyl acetate with formaldehyde in a fluidized bed reactor[J]. Industrial&Engineering Chemsitry Research,2017,56:9322-9330.
[24]Zhang G L,Zhang H H,Yang D,et al. Catalysts,kinetics and process optimization for the synthesis of methyl acrylate over Cs-P/γ-Al2O3[J].Catalysis Science&Technology,2016,6:6417-6430.
[25]Bao Q,Bu T,Yan J,et al.Synthesis of methyl acrylate by aldol condensation of methyl acetate with formaldehyde over Al2O3-supported barium catalyst[J]. Catalysis Letters,2017,147:1540-1550.
[26]Bao Q,Zhu W,Yan J,et al. Vapor phase aldol condensation of methyl acetate with formaldehyde over a Ba-La/Al2O3catalyst:The stabilizing role of La and effect of acid-base properties[J].RSC Advances,2017,7:52304-52311.
[27]Wang G,Wang H,Li C S,et al.One-step and in-situ catalytic synthesis of acrylates from acetates(or propionates)and trioxane at room temperature[J].Journal of Industrial and Engineering Chemistry,2017,55:173-182.
[28]Wang G,Li Z X,Li C S,et al.Kinetic and thermodynamic studies on one-step synthesis of methyl acrylate promoted by generated ionic liquid at mild temperature[J].Chemical Engineering Journal,2017,319:297-306.
[29]Wang G,Sararuk C,Li Z X,et al.Studies on mild catalytic synthesis of methyl acrylate via one-step aldol reaction[J]. AIChE Journal,2018,64(4):1359-1372.