Sustainable Production of Safe Plasticizers with Bio-Based Fumarates and 1,3-Dienes,Industrial & Engineering Chemistry Research

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Sustainable Production of Safe Plasticizers with Bio-Based Fumarates and 1,3-Dienes
Industrial & Engineering Chemistry Research ( IF 3.8 ) Pub Date : 2020-03-19 , DOI: 10.1021/acs.iecr.9b05840
Yancheng Hu ₁ , Chunwei Liu _{1,

2} , Pan Wang _{1,

3} , Guangyi Li ₁ , Aiqin Wang ₁ , Yu Cong ₁ , Xinmiao Liang _{1,

3} , Wei Li ₄ , Xiuli Zhang _{1,

3} , Ning Li _{1,

5}

Affiliation

1,2-Cyclohexanedicarboxylates (e.g., di(isononyl) 1,2-cyclohexanedicarboxylate, DINCH) are widely used as safe plasticizers in the polyvinylchloride (PVC) industry, and they are industrially manufactured from petroleum-derived o-xylene. To reduce the reliance on the limited fossil resources, we herein develop a sustainable alternative to 1,2-cyclohexanedicarboxylates with bio-based fumarates and 1,3-dienes. The Diels–Alder (D–A) cycloaddition and subsequent Pd/C-catalyzed hydrogenation are combined into a one-pot fashion, and notably they can take place efficiently under solvent-free conditions (>98% yield). The 1,2-cyclohexanedicarboxylates obtained in this work have similar physical properties to DINCH and do not show evidence of toxicity (LD₅₀ > 5 g/kg), which make them suitable candidates as safe plasticizers.

中文翻译：

使用生物基富马酸酯和1,3-二烯可持续生产安全增塑剂

1,2-环己二羧酸酯（例如，二（异壬基）1,2-环己二羧酸酯，DINCH）在聚氯乙烯（PVC）工业中被广泛用作安全的增塑剂，并且它们是由石油衍生的邻二甲苯工业生产的。为了减少对有限化石资源的依赖，我们在此开发了一种具有生物基富马酸酯和1,3-二烯的1,2-环己烷二羧酸酯的可持续替代品。Diels–Alder（D–A）环加成反应和随后的Pd / C催化加氢反应以一锅法的方式结合在一起，并且值得注意的是，它们可以在无溶剂条件下（> 98％的收率）高效地进行。在这项工作中获得的1,2-环己烷二甲酸酯具有与DINCH相似的物理性质，并且没有显示出毒性证据（LD ₅₀ > 5 g / kg），使其成为安全的增塑剂的合适选择。

更新日期：2020-04-24

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