| 刘传卓,李志坚,汤易天,李永刚,董开武.铑催化7-辛烯醛氢甲酰化反应合成1,9-壬二醛[J].分子催化,2024,38(2):160-170 |
| 铑催化7-辛烯醛氢甲酰化反应合成1,9-壬二醛 |
| Synthesis of 1,9-Nonanedial via Oct-7-enal in Rhodium-catalyzed Hydroformylation |
| 投稿时间：2023-12-24 修订日期：2024-01-15 |
| DOI：10.16084/j.issn1001-3555.2024.02.009 |
| 中文关键词: 1,9-壬二醛 7-辛烯醛 氢甲酰化 Xantphos 铑 |
| 英文关键词:1,9-nonanedial oct-7-enal hydroformylation Xantphos Rhodium |
| 基金项目: |
| 作者 | 单位 | E-mail | | 刘传卓 | 上海中化科技有限公司, 上海, 201315
华东师范大学 化学与分子工程学院, 上海, 200062 | | | 李志坚 | 上海中化科技有限公司, 上海, 201315 | | | 汤易天 | 上海中化科技有限公司, 上海, 201315 | | | 李永刚 | 上海中化科技有限公司, 上海, 201315 | liyonggang03@sinochem.com | | 董开武 | 华东师范大学 化学与分子工程学院, 上海, 200062 | |
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| 中文摘要: |
| 脂肪族二醛是一类重要的工业化学品中间体, 可以经过氧化、还原、还原酯化、还原胺化等反应获得二酸、二醇、二酯、二胺等各种重要的化学品. 我们报道了一种以丁二烯下游中间体—7-辛烯醛为原料的铑催化氢甲酰化反应合成1,9-壬二醛的方法, 考察了不同膦配体对催化剂性能的影响, 对反应工艺条件进行了研究和优化. 使用Rh(I)/Xantphos催化剂, 较优工艺条件下, 7-辛烯醛转化率>99%, 直链壬二醛收率86%, 醛产物正异比27, TON可达49 500. 最后, 对7-辛烯醛的氢甲酰化主反应和副反应机理进行了探讨. |
| 英文摘要: |
| As important chemical intermediates, aliphatic dialdehyde are synthesized by hydroformylation, normally, and can be further transformed to diacid, diol, diester, diamine and other important chemicals through oxidation, reduction, reductive esterification, reductive amination and other processes. Herein, we report the rhodium-catalyzed hydroformylation of oct-7-enal to prepare 1,9-nonanedial. The effects of the phosphine ligands and the reaction conditions on the catalytic performance in the hydroformylation were investigated in detailed. Under the Rh(I)/Xantphos catalytic system and the optimal reaction conditions, the oct-7-enal was almost completely conversed and 1,9-nonanedial in 86% yield was produced. Notably, the ratio of linear/branched aldehyde reached 27 and the TON reached 49 500. Meanwhile, the mechanisms of hydroformylation and side reactions were discussed. |
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