Heterogeneous catalytic reduction of substituted 5-acyl-1,3-dioxanes

Author:

Musin A. I.1ORCID,Borisova Yu. G.2ORCID,Raskil’dina G. Z.2ORCID,Daminev R. R.2ORCID,Davletshin A. R.2ORCID,Zlotskii S. S.2ORCID

Affiliation:

1. Institute of Chemical Technology and Engineering, Ufa State Petroleum Technological University, Sterlitamak

2. Ufa State Petroleum Technological University

Abstract

Objectives. To study the hydrogenation of substituted 5-acyl-1,3-dioxanes in the presence of metal-containing catalysts (Pt/Re, Pd/C, Ni/kieselguhr, and Ni/Mo).Methods. In order to determine the qualitative and quantitative composition of the reaction masses, the following analysis methods were used: gas-liquid chromatography (using the Kristall 2000 hardware complex); mass-spectroscopy (using Chromatec-Kristall 5000M device with NIST 2012); nuclear magnetic resonance (NMR) spectrometry (using Bruker AM-500 device with operating frequencies of 500 and 125 MHz).Results. Hydrogenation of substituted 5-acyl-1,3-dioxanes obtained by condensation of carbonyl compounds with paraformaldehyde and sulfuric acid was used to synthesize heterocyclic alcohols in the presence of metal-containing catalysts with a conversion of the initial ketones of 60–90% and a formation selectivity of target products of 70–90%. Substances were analyzed and confirmed by gas-liquid chromatography, mass spectrometry and NMR spectroscopy.Conclusions. The best catalyst for the reduction of substituted 5-acyl-1,3-dioxanes is Pd/C. By using this catalyst, it is possible to achieve a high selectivity for the formation of the corresponding heterocyclic alcohols at a conversion rate of the initial ketones of 60–90%.

Publisher

RTU MIREA

Subject

Inorganic Chemistry,Organic Chemistry,Fluid Flow and Transfer Processes,Process Chemistry and Technology

Reference19 articles.

1. Gafarov N.A., Kushnarenko V.M., Bugai D.E. Ingibitory korrozii: v 2 t. T. 2. Diagnostika i zashchita ot korrozii pod napryazheniem neftegazopromyslovogo oborudovaniya (Corrosion Inhibitors: in 2 v. V. 2. Diagnostics and Protection against Corrosion under Stress of Oil and Gas Equipment). Moscow: Khimiya; 2002. 367 p. (in Russ.).

2. Yakovenko E.A., Baimurzina Yu.L., Raskil’dina G.Z., Zlotskii S.S. Synthesis and herbicidal and antioxidant activity of a series of hetero- and carbocyclic derivatives of monochloroacetic acid. Russ. J. Appl. Chem. 2020;93(5):712–720. https://doi.org/10.1134/S1070427220050122

3. Kuz’mina, U.S., Raskil’dina, G.Z., Ishmetova, D.V., et al. Cytotoxic activity against SH-SY5Y neuroblastoma cells of heterocyclic compounds containing gemdichlorocyclopropane and/or 1,3-dioxacycloalkane fragments. Pharm. Chem. J. 2022;55(12):1293–1298. https://doi.org/10.1007/s11094-022-02574-6 [Original Russian Text: Kuz’mina, U.S., Raskil’dina, G.Z., Ishmetova, D.V., et al. Cytotoxic activity against SH-SY5Y neuroblastoma cells of heterocyclic compounds containing gem-dichlorocyclopropane and/or 1,3-dioxacycloalkane fragments. Khimiko-Farmatsevticheskii Zhurnal. 2022;55(12):27–32 (in Russ.). https://doi.org/10.30906/0023-1134-2021-55-12-27-32]

4. Maximov A.L., Nekhaev A.I., Ramazanov D.N. Ethers and acetals, promising petrochemicals from renewable sources. Pet. Chem. 2015;55(1):1–21. https://doi.org/10.1134/S0965544115010107 [Original Russian Text: Maximov A.L., Nekhaev A.I., Ramazanov D.N. Ethers and acetals, promising petrochemicals from renewable sources. Neftekhimiya. 2015;55(1):3–24 (in Russ.). https://doi.org/10.7868/S0028242115010104]

5. Samoilov V., Goncharova A., Zarezin D., Kniazeva M., Ladesov A., Maximov A. Bio-based solvents and gasoline components from renewable 2,3-butanediol and 1,2-propanediol: synthesis and characterization. Molecules. 2020; 25(7):1723. https://doi.org/10.3390/molecules25071723

Cited by 3 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

同舟云学术

1.学者识别学者识别

2.学术分析学术分析

3.人才评估人才评估

"同舟云学术"是以全球学者为主线,采集、加工和组织学术论文而形成的新型学术文献查询和分析系统,可以对全球学者进行文献检索和人才价值评估。用户可以通过关注某些学科领域的顶尖人物而持续追踪该领域的学科进展和研究前沿。经过近期的数据扩容,当前同舟云学术共收录了国内外主流学术期刊6万余种,收集的期刊论文及会议论文总量共计约1.5亿篇,并以每天添加12000余篇中外论文的速度递增。我们也可以为用户提供个性化、定制化的学者数据。欢迎来电咨询!咨询电话:010-8811{复制后删除}0370

www.globalauthorid.com

TOP

Copyright © 2019-2024 北京同舟云网络信息技术有限公司
京公网安备11010802033243号  京ICP备18003416号-3