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Study on the selective hydrogenation of isophorone
RSC Advances ( IF 3.9 ) Pub Date : 2021-1-22 , DOI: 10.1039/d0ra08107h Lei Xu 1 , Shaoyin Sun 2 , Xing Zhang 2 , Haofei Gao 2 , Wei Wang 2
RSC Advances ( IF 3.9 ) Pub Date : 2021-1-22 , DOI: 10.1039/d0ra08107h Lei Xu 1 , Shaoyin Sun 2 , Xing Zhang 2 , Haofei Gao 2 , Wei Wang 2
Affiliation
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3,3,5-Trimethylcyclohexanone (TMCH) is an important pharmaceutical intermediate and organic solvent, which has important industrial significance. The selective hydrogenation of isophorone was studied over noble metal (Pd/C, Pt/C, Ir/C, Ru/C, Pd/SiO2, Pt/SiO2, Ir/SiO2, Ru/SiO2), and non-noble metal (RANEY® Ni, RANEY® Co, RANEY® Cu, RANEY® Fe, Ni/SiO2, Co/SiO2, Cu/SiO2, Fe/SiO2) catalysts and using solvent-free and solvent based synthesis. The results show that the solvent has an important effect on the selectivity of TMCH. The selective hydrogenation of isophorone to TMCH can be influenced by the tetrahydrofuran solvent. The conversion of isophorone is 100%, and the yield of 3,3,5-trimethylcyclohexanone is 98.1% under RANEY® Ni and THF. The method was applied to the selective hydrogenation of isopropylidene acetone, benzylidene acetone and 6-methyl-5-ene-2-heptanone. The structures of the hydrogenation product target (4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one) were characterized using 1H-NMR and 13C-NMR. The yields of 4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one were 97.2%, 98.5% and 98.2%, respectively. The production cost can be reduced by using RANEY® metal instead of noble metal palladium. This method has good application prospects.
中文翻译：
异佛尔酮选择性加氢的研究
3,3,5-三甲基环己酮（TMCH）是一种重要的医药中间体和有机溶剂，具有重要的工业意义。在贵金属（Pd/C、Pt/C、Ir/C、Ru/C、Pd/SiO 2、Pt/SiO 2、Ir/SiO 2、Ru/SiO 2）和非金属上研究了异佛尔酮的选择性加氢。 -贵金属（RANEY® Ni、RANEY® Co、RANEY® Cu、RANEY® Fe、Ni/SiO 2、Co/SiO 2、Cu/SiO 2、Fe/SiO 2) 催化剂和使用无溶剂和基于溶剂的合成。结果表明，溶剂对TMCH的选择性有重要影响。异佛尔酮选择性氢化为 TMCH 可能受四氢呋喃溶剂的影响。在RANEY® Ni和THF下，异佛尔酮的转化率为100%，3,3,5-三甲基环己酮的收率为98.1%。该方法应用于异丙叉丙酮、亚苄基丙酮和6-甲基-5-烯-2-庚酮的选择性加氢。使用1 H-NMR 和13C-核磁共振。4-甲基戊-2-酮、4-苄基丁-2-酮和6-甲基-庚烷-2-酮的收率分别为97.2%、98.5%和98.2%。使用 RANEY® 金属代替贵金属钯可以降低生产成本。该方法具有良好的应用前景。
更新日期：2021-01-22
中文翻译：
异佛尔酮选择性加氢的研究
3,3,5-三甲基环己酮（TMCH）是一种重要的医药中间体和有机溶剂，具有重要的工业意义。在贵金属（Pd/C、Pt/C、Ir/C、Ru/C、Pd/SiO 2、Pt/SiO 2、Ir/SiO 2、Ru/SiO 2）和非金属上研究了异佛尔酮的选择性加氢。 -贵金属（RANEY® Ni、RANEY® Co、RANEY® Cu、RANEY® Fe、Ni/SiO 2、Co/SiO 2、Cu/SiO 2、Fe/SiO 2) 催化剂和使用无溶剂和基于溶剂的合成。结果表明，溶剂对TMCH的选择性有重要影响。异佛尔酮选择性氢化为 TMCH 可能受四氢呋喃溶剂的影响。在RANEY® Ni和THF下，异佛尔酮的转化率为100%，3,3,5-三甲基环己酮的收率为98.1%。该方法应用于异丙叉丙酮、亚苄基丙酮和6-甲基-5-烯-2-庚酮的选择性加氢。使用1 H-NMR 和13C-核磁共振。4-甲基戊-2-酮、4-苄基丁-2-酮和6-甲基-庚烷-2-酮的收率分别为97.2%、98.5%和98.2%。使用 RANEY® 金属代替贵金属钯可以降低生产成本。该方法具有良好的应用前景。
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