期刊
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
卷 7, 期 3, 页码 2980-2988出版社
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.8b04310
关键词
Plasticizers; Diacetone alcohol; Fumarates; Dehydration/Diels-Alder reaction; Hydrogenation; 1,2-Cyclohexanedicarboxylate
资金
- National Natural Science Foundation of China [21690082, 21776273, 21721004, 21801239]
- DNL Cooperation Fund, CAS [DNL180301]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB17020100]
- National Key Projects for Fundamental Research and Development of China [2016YFA0202801]
- Dalian Science Foundation for Distinguished Young Scholars [201511005]
1,2-Cyclohexanedicarboxylates, which are one of the most commonly used plasticizers in the poly(vinyl chloride) (PVC) industry, are generally prepared via the oxidation/esterification/hydrogenation of o-xylene (or naphthalene). Herein, we develop an alternative route toward cyclohexane-based plasticizers using diacetone alcohol and fumarates as the starting materials. The process includes a mild Raney Ni-catalyzed hydrogenation of diacetone alcohol, an one-step dehydration/Diels-Alder reaction of resulting 2-methyl-2,4-pentandiol and fumarates in a choline chloride (ChCl) based deep eutectic solvent (DES), and a further Pd/C-catalyzed hydrogenation. The toxicological tests indicate that the as-synthesized di(2-ethylhexyl) 3,5-dimethylcyclohexane-1,2-dicarboxylate can serve as a safe plasticizer for PVC materials.
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