Methanolysis of amides under high-temperature and high-pressure conditions with a continuous tubular reactor

被引:3
作者
Zou, Pengcheng [1 ]
Wang, Kai [1 ]
机构
[1] Tsinghua Univ, Dept Chem Engn, State Key Lab Chem Engn, Beijing 100084, Peoples R China
来源
CHINESE JOURNAL OF CHEMICAL ENGINEERING | 2023年 / 58卷
基金
中国国家自然科学基金;
关键词
Amide methanolysis reaction; Flow chemistry; Continuous reaction; Process intensification; BASIC METHANOLYSIS; CATALYZED ESTERIFICATION; ACIDS; MICROREACTORS; DECOMPOSITION; RATES;
D O I
10.1016/j.cjche.2022.10.009
中图分类号
TQ [化学工业];
学科分类号
0817 ;
摘要
The methanolysis of amides, which is widely employed in the synthetic organic chemistry, hardly occurs under mild conditions. To safely and controllably intensify the methanolysis reaction with high -temperature and high-pressure environment, a continuous tubular reaction technology is developed, whose space-time yield is over twice of that of the conventional batch reaction. The methanolysis of acetanilide is selected as the representative reaction, and the influences of temperature, pressure, reac-tant and catalyst concentration, and residence time on the reaction performances are systematically investigated. Taking the advantages of precise temperature and reaction time control by the tubular reac-tor, the kinetics of acetanilide methanolysis are determined and compared to the kinetics of acetanilide hydrolysis reaction. The tubular reaction method is also employed to test a variety of other amides to show the effects of substituents, steric hindrance, and alkalinity on the reaction rate of methanolysis.(c) 2022 The Chemical Industry and Engineering Society of China, and Chemical Industry Press Co., Ltd. All rights reserved.
引用
收藏
页码:170 / 178
页数:9
相关论文
共 40 条
  • [1] Albert A., 1984, The Determination of Ionization Constants. A Laboratory Manual, V3rd
  • [2] SYNTHESIS OF ISOQUINOLINE ALKALOIDS .2. THE SYNTHESIS AND REACTIONS OF 4-METHYL-3-PYRIDINECARBOXALDEHYDE AND OTHER 4-METHYL-3-SUBSTITUTED PYRIDINES
    BOBBITT, JM
    SCOLA, DA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) : 560 - 564
  • [3] MECHANISM OF BASIC METHANOLYSIS OF BENZANILIDES
    BROXTON, TJ
    DEADY, LW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (18) : 2767 - 2769
  • [4] SUBSTITUENT EFFECTS ON THE BASIC METHANOLYSIS OF A SERIES OF SUBSTITUTED N-METHYL-PARA-TOLUANILIDES
    BROXTON, TJ
    DUDDY, NW
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (04) : 903 - 906
  • [5] RATES OF BASIC METHANOLYSIS OF SOME N-ALKYL-PARA-NITROACETANILIDES AND 4-(N'-ALKYLACETAMIDO)PYRIDINES
    BROXTON, TJ
    DEADY, LW
    WILLIAMS.PR
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (05) : 1053 - 1057
  • [6] Direct Preparation of Nitriles from Carboxylic Acids in Continuous Flow
    Cantillo, David
    Kappe, C. Oliver
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) : 10567 - 10571
  • [7] Fe-catalyzed esterification of amides via C-N bond activation
    Chen, Xiuling
    Hu, Siying
    Chen, Rongxing
    Wang, Jian
    Wu, Minghu
    Guo, Haibin
    Sun, Shaofa
    [J]. RSC ADVANCES, 2018, 8 (09): : 4571 - 4576
  • [8] Direct Catalytic Alcoholysis of Unactivated 8-Aminoquinoline Amides
    Deguchi, Toru
    Xin, Hai-Long
    Morimoto, Hiroyuki
    Ohshima, Takashi
    [J]. ACS CATALYSIS, 2017, 7 (05): : 3157 - 3161
  • [9] Continuous synthesis of isobutylaluminoxanes in a compact and integrated approach
    Feng, Yirong
    Zhang, Mengbo
    Zhang, Haomiao
    Wang, Jingdai
    Yang, Yongrong
    [J]. CHEMICAL ENGINEERING JOURNAL, 2021, 425
  • [10] Liquid phase oxidation chemistry in continuous-flow microreactors
    Gemoets, Hannes P. L.
    Su, Yuanhai
    Shang, Minjing
    Hessel, Volker
    Luque, Rafael
    Noel, Timothy
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (01) : 83 - 117