Alternate Preparation of Norbornene and Dimethanooctahydronaphthalene via Diels–Alder Reaction: Process Simulation and Experimental Verification

IF 3.8 3区工程技术 Q2 ENGINEERING, CHEMICAL

Industrial & Engineering Chemistry Research Pub Date : 2024-01-24 DOI:10.1021/acs.iecr.3c03986

Haofei Huang, Zehao Jing, Hui Guo, Tingting Ge*, Yanxia Zheng, Yuchao Li, Xinpeng Guo, Guangjun Cui*, Wenwen Zhang, Liran Ding and Cuncun Zuo*,

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Abstract

Synthesis of norbornene (NBE) and dimethanooctahydronaphthalene (DMON), respectively, via a Diels–Alder (D–A) reaction or consecutive D–A reaction with ethylene and cyclopentadiene (CPD) from dicyclopentadiene (DCPD) depolymerization as raw materials was an important process route for high value-added utilization of ethylene and C5 resources. The optimal reaction conditions (such as temperature, pressure, and raw material ratio) were obtained via sensitivity analysis, with the results showing that the reaction of ethylene and CPD was more difficult than that of NBE and CPD. Response surface analysis was applied to examine the effects of multiple factors (including temperature, molar ratio, and reaction time) on product results. The accuracy of the calculation results was verified through experiments, and the results were consistent with actual. The final selectivity of NEB reached 89%, and that of DMON reached over 95%.

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通过 Diels-Alder 反应替代制备降冰片烯和二甲烷八氢萘：过程模拟与实验验证

以乙烯和双环戊二烯（DCPD）解聚生成的环戊二烯（CPD）为原料，通过二元-阿尔德（D-A）反应或连续D-A反应分别合成降冰片烯（NBE）和二甲桥八氢萘（DMON），是乙烯和C5资源高附加值利用的重要工艺路线。通过灵敏度分析获得了最佳反应条件（如温度、压力和原料配比），结果表明乙烯与 CPD 的反应比 NBE 与 CPD 的反应更困难。应用响应面分析法考察了多种因素（包括温度、摩尔比和反应时间）对产品结果的影响。通过实验验证了计算结果的准确性，结果与实际相符。NEB 的最终选择性达到 89%，DMON 的最终选择性超过 95%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Industrial & Engineering Chemistry Research 工程技术-工程：化工

CiteScore

7.40

自引率

7.10%

发文量

1467

审稿时长

2.8 months

期刊介绍： ndustrial & Engineering Chemistry, with variations in title and format, has been published since 1909 by the American Chemical Society. Industrial & Engineering Chemistry Research is a weekly publication that reports industrial and academic research in the broad fields of applied chemistry and chemical engineering with special focus on fundamentals, processes, and products.