Cu-Mn催化剂制备方法对苯乙酮加氢制苯乙醇催化性能的影响

曹媛; 贺洋; 刘宇飞; 王康军; 刘蝈蝈

doi:10.12434/j.issn.2097-2547.20240503

您当前的位置：

首页 >

文章列表页 >

Cu-Mn催化剂制备方法对苯乙酮加氢制苯乙醇催化性能的影响

低碳分子转化合成 | 更新时间：2025-10-22

- Cu-Mn催化剂制备方法对苯乙酮加氢制苯乙醇催化性能的影响
- Effects of preparation methods of Cu-Mn catalysts on catalytic performances of acetophenone hydrogenation to phenylethanol
- 低碳化学与化工 2025, 50(10): 27-35.
- 作者机构：
  
  沈阳化工大学化学工程学院，辽宁沈阳 110142
- 作者简介：
  
  曹媛（1998—），硕士研究生，研究方向为碳一化工与催化剂，E-mail：694929675@qq.com。
  刘蝈蝈（1988—），博士，副教授，研究方向为碳一化工与催化剂，E-mail：lguoguo@syuct.edu.cn。
- 基金信息：
  
  辽宁省自然科学基金(2021-NLTS-12-03);辽宁省教育厅项目(LJKZ0439);辽宁省教育厅青年项目(LJKQ2021068);沈阳化工大学优青托举计划(2019YQ01)
- DOI：10.12434/j.issn.2097-2547.20240503
  中图分类号： TQ426.8
- 收稿：2024-12-19，
  
  修回：2025-02-10，
  
  纸质出版：2025-10-25
- 稿件说明：
移动端阅览
曹媛,贺洋,刘宇飞等.Cu-Mn催化剂制备方法对苯乙酮加氢制苯乙醇催化性能的影响[J].低碳化学与化工,2025,50(10):27-35.

CAO Yuan,HE Yang,LIU Yufei,et al.Effects of preparation methods of Cu-Mn catalysts on catalytic performances of acetophenone hydrogenation to phenylethanol[J].Low-Carbon Chemistry and Chemical Engineering,2025,50(10):27-35.
曹媛,贺洋,刘宇飞等.Cu-Mn催化剂制备方法对苯乙酮加氢制苯乙醇催化性能的影响[J].低碳化学与化工,2025,50(10):27-35. DOI： 10.12434/j.issn.2097-2547.20240503.

CAO Yuan,HE Yang,LIU Yufei,et al.Effects of preparation methods of Cu-Mn catalysts on catalytic performances of acetophenone hydrogenation to phenylethanol[J].Low-Carbon Chemistry and Chemical Engineering,2025,50(10):27-35. DOI： 10.12434/j.issn.2097-2547.20240503.

摘要

苯乙醇作为重要的化工原料，可由苯乙酮催化加氢反应制备。然而，目前使用的苯乙酮加氢制苯乙醇催化剂存在产物选择性较低、稳定性较差和成本较高等问题。分别采用熔融法和共沉淀法制备了Cu-Mn催化剂（Cu-MnO

-MT和Cu-MnO

-CP），通过XRD和H

-TPR等表征了催化剂的结构，研究了催化剂的催化性能，并优化了反应条件。结果表明，与Cu-MnO

-CP相比，Cu-MnO

-MT具有更丰富的氧空位活性位点，这有利于增强表面氧的迁移，提高苯乙酮在催化剂表面的吸附能，降低反应能垒，促进苯乙酮活化，从而提高苯乙酮转化率。在反应温度为100 ℃、反应压力为2.5 MPa、苯乙酮液时空速为1.8 h

-1

和

(苯乙酮)为15:1的最优条件下反应8 h，Cu-MnO

-MT表现出更好的催化性能，其苯乙酮转化率为99.75%，苯乙醇选择性为99.83%。此外，Cu-MnO

-MT在最优反应条件下连续反应40 h，其苯乙酮转化率维持在99%以上。

Abstract

As an important chemical raw material

phenylethanol can be prepared by catalytic hydrogenation of acetophenone. However

the currently used catalysts for hydrogenation of acetophenone to phenylethanol have problems such as low product selectivities

poor stabilities and high costs. Cu-Mn catalysts (Cu-MnO

-MT and Cu-MnO

-CP) were prepared by melting method and co precipitation metho

respectively. The structures of catalysts were characterized by XRD

-TPR

etc. The catalytic performances of catalysts were studied and the reaction conditions were optimized. The results show that compared with Cu-MnO

-CP

Cu-MnO

-MT has more abundant oxygen vacancy active sites

which are conducive to enhancing the migration of surface oxygen

increasing the adsorption energy of acetophenone on the catalyst surface

reducing the reaction energy barrier

promoting the activation of acetophenone

and thus improving the acetophenone conversion rate. Under the optimal conditions of reaction temperature of 100 ℃

reaction pressure of 2.5 MPa

liquid space velocity of 1.8 h

-1

and

(acetophenone) of 15:1

Cu-MnO

-MT exhibits better catalytic performance with the acetophenone conversion rate of 99.75% and phenylethanol selectivity of 99.83% after reacting for 8 h. In addition

after continuously reacting under optimal reaction conditions for 40 h

the acetophenone conversion rate of Cu-MnO

-MT remains above 99%.

关键词

Keywords

references

杜松山 , 杨彦红 . 以苯乙酮为原料制备 α -苯乙醇方法研究 [J ] . 科技信息 , 2014 , ( 2 ): 109 - 110 .

DU S S , YANG Y H . Research on the preparation method of α -phenylethanol from acetophenone [J ] . Science and Technology Information , 2014 , ( 2 ): 109 - 110 .

PEI F Y , WANG Z M , LV J H , et al . Efficient catalytic transfer hydrogenation of acetophenone to 1-phenylethanol over Cu-Zn-Al catalysts [J ] . Industrial & Engineering Chemistry Research , 2022 , 61 ( 16 ): 5419 - 5428 .

LV Z G , WANG J M , ZHANG S Y , et al . Highly selective hydrogenation of acetophenone over supported amorphous alloy catalyst [J ] . Applied Organometallic Chemistry , 2020 , 34 ( 4 ): e5555 .

YOU P Y , WU L M , ZHOU L , et al . Impact of oxygen-containing groups on Pd/C in the catalytic hydrogenation of acetophenone and phenylacetylene [J ] . Catalysts , 2024 , 14 ( 8 ): 545 .

柳凡玲 , 王嗣鑫 , 刘蝈蝈 , 等 . 用于苯乙酮催化加氢制 α -苯乙醇高稳定Cu/SiO 2 催化剂的研究 [J ] . 当代化工 , 2024 , 53 ( 4 ): 802 - 808 .

LIU F L , WANG S X , LIU G G , et al . Research on high stability Cu/SiO 2 catalyst for acetophenone hydrogenation to α -phenylethanol [J ] . Contemporary Chemical Industry , 2024 , 53 ( 4 ): 802 - 808 .

吴静 . 高效低污染糠醛选择加氢催化剂的研究 [D ] . 大连 : 大连理工大学 , 2009 .

WU J . Study on high efficiency and low pollution catalysts for selective hydrogenation of furfural [D ] . Dalian : Dalian University of Technology , 2009 .

JAYAKUMAR S , MODAK A , GUO M , et al . Ultrasmall platinum stabilized on triphenylphosphine-modified silica for chemoselective hydrogenation [J ] . Chemistry: A European Journal , 2017 , 23 ( 32 ): 7791 - 7797 .

SU N , GAO X Y , CHEN X Y , et al . The enantioselective hydrogenation of acetophenone over pd concave tetrahedron nanocrystals affected by the residual adsorbed capping agent polyvinylpyrrolidone (PVP) [J ] . Journal of Catalysis , 2018 , 367 : 244 - 251 .

YUKI Y , TOUGE T , NARA H , et al . Selective asymmetric transfer hydrogenation of α ‐substituted acetophenones with bifunctional oxo-tethered ruthenium (II) catalysts [J ] . Advanced Synthesis & Catalysis , 2018 , 360 ( 3 ): 568 - 574 .

刘全遥 . 高分散铜基催化剂制备及其加氢草酸二甲酯制备乙二醇催化性能研究 [D ] . 北京 : 北京化工大学 , 2012 .

LIU Q Y . Synthesis and catalytic performance of highly dispersed copper based catalysts for dimethyl oxalate to ethylene glycol [D ] . Beijing : Beijing University of Chemical Technology , 2012 .

崔新悦 , 李英霞 , 黄崇品 , 等 . 助剂Co对Ni/SBA-15分子筛催化剂催化苯乙酮加氢反应性能的影响 [J ] . 石油化工 , 2012 , 41 ( 11 ): 1258 - 1263 .

CUI X Y , LI Y X , HUANG C P , et al . Effect of Co cocatalyst on Ni/SBA-15 molecular sieve catalysts for hydrogenation of acetophenone [J ] . Petrochemical Technology , 2012 , 41 ( 11 ): 1258 - 1263 .

李志伟 , 谌其亭 , 李江胜 , 等 . “苯乙酮的制备”实验方法的改进 [J ] . 化学教育 , 2018 , 39 ( 18 ): 32 - 34 .

LI Z W , CHEN Q T , LI J S , et al . Improvement of the experiment method in the preparation of acetophenone [J ] . Chemistry Education , 2018 , 39 ( 18 ): 32 - 34 .

UMMEY R , ZANNATUL K , NURUL I M , et al . A review on the recent advances in the reductions of carbon-carbon/oxygen multiple bonds including aromatic rings using raney Ni-Al alloy or Al powder in the presence of noble metal catalysts in water [J ] . Topics in Catalysis , 2018 , 61 ( 7/8 ): 1 - 15 .

柳凡玲 . 用于苯乙酮催化加氢制备1-苯乙醇Cu基催化剂性能的研究 [D ] . 沈阳 : 沈阳化工大学 , 2023 .

LIU F L . Study on the performance of Cu based catalysts for the catalytic hydrogenation of acetophenone to 1-phenylethanol [D ] . Shenyang : Shenyang University of Chemical Technology , 2023 .

WANG B , JING M M , AN H , et al . Hydrogenation performance of acetophenone to 1-phenylethanol on highly active nano Cu/SiO 2 catalyst [J ] . Catalysis Letters , 2020 , 150 : 56 - 64 .

廖湘洲 , 卢磊 , 宁春利 , 等 . 草酸二甲酯加氢制乙醇酸甲酯反应铜基催化剂的失活原因分析 [J ] . 复旦学报（自然科学版） , 2012 , 51 ( 6 ): 773 - 776+782 .

LIAO X Z , LU L , NING C L , et al . Deactivation analysis for copper-based catalysts in hydrogenation of dimethy oxalate to methyl glycolate [J ] . Journal of Fudan University (Natural Science) , 2012 , 51 ( 6 ): 773 - 776+782 .

JIANG X , HAN B , FU J W . The Preparation of copper-manganese catalysts using a sequentially feeding microreactor [J ] . Industrial & Engineering Chemistry Research , 2024 .

ZHAO L M , YANG Y J , LIU J , et al . Oxidation mechanism of HCHO on copper-manganese composite oxides catalyst [J ] . Chemosphere , 2023 , 330 : 138754 .

VENKATALAXMI A , PADMAVATHI B S , AMARANATH T . A general solution of unsteady stokes equations [J ] . Fluid Dynamics Research , 2004 , 35 ( 3 ): 229 - 236 .

PHOKA S , LAOKUL P , SWATSITANG E , et al . Synthesis, structural and optical properties of CeO 2 nanoparticles synthesized by a simple polyvinyl pyrrolidone (PVP) solution route [J ] . Materials Chemistry and Physics , 2009 , 115 ( 1 ): 423 - 428 .

CHEN H , RUAN H H , LU X L , et al . Efficient catalytic transfer hydrogenation of furfural to furfuryl alcohol in near-critical isopropanol over Cu/MgO-Al 2 O 3 catalyst [J ] . Molecular Catalysis , 2018 , 445 : 94 - 101 .

VILLAVERDE M M , GARETTO T F , MARCHI A J . Liquid-phase transfer hydrogenation of furfural to furfuryl alcohol on Cu-Mg-Al catalysts [J ] . Catalysis Communications , 2015 , 58 : 6 - 10 .

BERTERO N M , APESTEGUÍA C R , MARCHI A J . Catalytic and kinetic study of the liquid-phase hydrogenation of acetophenone over Cu/SiO 2 catalyst [J ] . Applied Catalysis A: General , 2008 , 349 ( 1/2 ): 100 - 109 .

TRASARTI A F , BERTERO N M , APESTEGUIA C R , et al . Liquid-phase hydrogenation of acetophenone over silica-supported Ni, Co and Cu catalysts: Influence of metal and solvent [J ] . Applied Catalysis A: General , 2014 , 475 : 282 - 291 .

CHONG S Y , ZHAO S , LI J Y , et al . Enhanced the dehydrocyclization of 1,4-butanediol to γ -butyrolactone via the regulation of interface oxygen vacancies in Cu/MgO-CeO 2 catalyst [J ] . Chemical Engineering Journal , 2024 , 489 : 151366 .

徐长青 , 朱大建 , 李光兴 . Ni-B/SiO 2 非晶态催化剂对苯乙酮的催化加氢研究 [J ] . 分子催化 , 2004 , 18 ( 4 ): 281 - 285 .

XU C Q , ZHU D J , LI G X . Study on the hydrogenation of acetophenone catalyzed by Ni-B/SiO 2 amorphous catalyst [J ] . Molecular Catalysis , 2004 , 18 ( 4 ): 281 - 285 .

PARIDA S K , MOHAPATRA J , MISHRA D K . Structural and magnetic behavior of spinel CuMn 2 O 4 synthesized by co-melting technique [J ] . Materials Letters , 2016 , 181 : 116 - 118 .

ZHAO S , YUE H R , ZHAO Y J , et al . Chemoselective synthesis of ethanol via hydrogenation of dimethyl oxalate on Cu/SiO 2 : Enhanced stability with boron dopant [J ] . Journal of Catalysis , 2013 , 297 : 142 - 150 .

LIU M M , FAN B B , SHI X F , et al . Ru/ZIF-8 with a chiral modifier for asymmetric hydrogenation of acetophenone [J ] . Catalysis Communications , 2013 , 42 : 20 - 24 .

LEÓN-GUTIÉRREZ YASNA , CÁRDENAS-TRIVIÑO G . Catalyst characterization Ni-Sn nanoparticles supported in Al 2 O 3 and MgO: Acetophenone hydrogenation [J ] . Nanomaterials and Nanotechnology , 2022 , 12 : 18479 .

韩利华 , 芮玉兰 , 郭绍义 , 等 . 共沉淀法制备铜系催化剂及其稳定性的研究 [J ] . 环境科学与技术 , 2006 , ( 8 ): 10 - 11 .

HAN L H , RUI Y L , GUO S Y , et al . Stability of copper catalysts prepared by Co-precipitation [J ] . Environmental Science and Technology , 2006 , ( 8 ): 10 - 11 .

浏览量

下载量

CNKI被引量

文章被引用时，请邮件提醒。

提交

工具集

关联资源

V-SBA-15催化氧化乙苯制苯乙酮反应

镍铁双金属催化剂的制备及其催化甲烷裂解性能评价