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Efficient production of adipic acid from 2-methoxycyclohexanone by aerobic oxidation with a phosphotungstic acid catalyst
Green Chemistry ( IF 9.3 ) Pub Date : 2020-06-24 , DOI: 10.1039/d0gc01277g Kosuke Hatakeyama 1, 2, 3, 4, 5 , Yoshinao Nakagawa 1, 2, 3, 4, 5 , Masazumi Tamura 1, 2, 3, 4, 5 , Keiichi Tomishige 1, 2, 3, 4, 5
Green Chemistry ( IF 9.3 ) Pub Date : 2020-06-24 , DOI: 10.1039/d0gc01277g Kosuke Hatakeyama 1, 2, 3, 4, 5 , Yoshinao Nakagawa 1, 2, 3, 4, 5 , Masazumi Tamura 1, 2, 3, 4, 5 , Keiichi Tomishige 1, 2, 3, 4, 5
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Oxidative cleavage reaction of 2-methoxycyclohexanone (2-MCO) to adipic acid (AA) and methanol with O2 in water solvent was investigated. 2-MCO and AA are one of the lignin-based compounds produced via hydrogenation of guaiacol and an important monomer in industry, respectively. Various vanadium compounds and heteropolyacids were tested as homogeneous catalysts because vanadium compounds, especially phosphomolybdovanadic acids, have been known to be active in various oxidative cleavage reactions with O2. Simple vanadium-free phosphotungstic acid (H3PW12O40), which has not been regarded as an oxidation catalyst using O2 as the oxidant, showed good catalytic activity and excellent selectivity to AA. The carbon-based AA yield reached 74% (86% in molar basis) and this value was higher than those obtained with vanadium-based catalysts. A reuse test and 31P NMR confirmed that the H3PW12O40 catalyst was stable and reusable. Kinetic studies and the reaction test using a radical inhibitor suggested that the reaction mechanism is not auto-oxidation involving free radicals. Instead, the substrate was first activated by one-electron oxidation by H3PW12O40 catalyst and then reacted with O2.
中文翻译：
通过磷钨酸催化剂的好氧氧化由2-甲氧基环己酮高效生产己二酸
研究了O 2在水溶剂中2-甲氧基环己酮（2-MCO）对己二酸（AA）和甲醇的氧化裂解反应。2-MCO和AA是分别通过愈创木酚和工业上的重要单体加氢生成的木质素基化合物之一。已测试了各种钒化合物和杂多酸作为均相催化剂，因为已知钒化合物（尤其是磷钼钒酸）在与O 2的各种氧化裂解反应中具有活性。简单的无钒磷钨酸（H 3 PW 12 O 40），尚未被视为使用O 2的氧化催化剂作为氧化剂，具有良好的催化活性和对AA的优异选择性。碳基AA的收率达到74％（以摩尔计为86％），该值高于钒基催化剂。重复使用测试和31 P NMR证实H 3 PW 12 O 40催化剂稳定且可重复使用。动力学研究和使用自由基抑制剂的反应测试表明，反应机理并非涉及自由基的自氧化作用。取而代之的是，首先通过H 3 PW 12 O 40催化剂通过单电子氧化活化衬底，然后使其与O 2反应。
更新日期：2020-08-04
中文翻译：
通过磷钨酸催化剂的好氧氧化由2-甲氧基环己酮高效生产己二酸
研究了O 2在水溶剂中2-甲氧基环己酮（2-MCO）对己二酸（AA）和甲醇的氧化裂解反应。2-MCO和AA是分别通过愈创木酚和工业上的重要单体加氢生成的木质素基化合物之一。已测试了各种钒化合物和杂多酸作为均相催化剂，因为已知钒化合物（尤其是磷钼钒酸）在与O 2的各种氧化裂解反应中具有活性。简单的无钒磷钨酸（H 3 PW 12 O 40），尚未被视为使用O 2的氧化催化剂作为氧化剂，具有良好的催化活性和对AA的优异选择性。碳基AA的收率达到74％（以摩尔计为86％），该值高于钒基催化剂。重复使用测试和31 P NMR证实H 3 PW 12 O 40催化剂稳定且可重复使用。动力学研究和使用自由基抑制剂的反应测试表明，反应机理并非涉及自由基的自氧化作用。取而代之的是，首先通过H 3 PW 12 O 40催化剂通过单电子氧化活化衬底，然后使其与O 2反应。
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