己二腈制备方法的研究进展

doi:10.16085/j.issn.1000-6613.2024-0892

化工进展 ›› 2025, Vol. 44 ›› Issue (7): 3683-3696.DOI: 10.16085/j.issn.1000-6613.2024-0892

• 化工过程与装备 •

己二腈制备方法的研究进展

杜磊¹(), 曹志涛², 许浪¹, 张英杰², 孙宝昌¹^,³(), 邹海魁¹^,³, 初广文¹^,³, 陈建峰¹^,³

^1.北京化工大学有机无机复合材料国家重点实验室，北京 100029
^2.中国石油天然气股份有限公司辽阳石化分公司，辽宁辽阳 111003
^3.北京化工大学教育部超重力工程研究中心，北京 100029

收稿日期:2024-06-02 修回日期:2024-07-26 出版日期:2025-07-25 发布日期:2025-08-04
通讯作者: 孙宝昌
作者简介:杜磊（1995—），男，博士研究生，研究方向为超重力反应器工程。E-mail：2021400037@mail.buct.edu.cn。
基金资助:
国家自然科学基金(22288102);国家自然科学基金(U22B6011)

Progress research in preparation of adiponitrile

DU Lei¹(), CAO Zhitao², XU Lang¹, ZHANG Yingjie², SUN Baochang¹^,³(), ZOU Haikui¹^,³, CHU Guangwen¹^,³, CHEN Jianfeng¹^,³

^1.State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China
^2.PetroChina Liaoyang Petrochemical Company, Liaoyang 111003, Liaoning, China
^3.Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China

Received:2024-06-02 Revised:2024-07-26 Online:2025-07-25 Published:2025-08-04
Contact: SUN Baochang

摘要/Abstract

摘要：

己二腈作为生产聚酰胺（尼龙66）的主要原料之一，其生产工艺长期被国外公司垄断。近年来，随着尼龙66需求量的增加，己二腈的供需缺口逐渐增大，其高效的生产技术逐渐成为研究热点。本文介绍了己二腈的制备方法如丁二烯法、丙烯腈电解二聚法和己二酸氨化法的基础研究、工艺特点及发展方向等；从机理出发探讨了过程强化技术在丙烯腈电解二聚法和己二酸氨化法中的应用可行性，并对己二酸氨化法的动力学和热力学进行了总结。将过程强化技术应用于己二腈生产过程是推动己二腈高效绿色生产的关键，对己二腈生产技术的提升和自主化具有重要意义。

关键词: 己二酸氨化法, 丁二烯法, 丙烯腈电解二聚法, 己二腈, 过程强化, 有机化合物, 化学过程, 反应动力学

Abstract:

Adiponitrile, as one of the main raw materials for producing polyamide (nylon 66), has been long monopolized by foreign companies. In recent years, the research on the high efficiency production methods of adiponitrile has gradually become a hot topic because the increasing demand of nylon 66 helped bring about the growing gap between adiponitrile supply and demand. The basic research, process characteristics and development direction of the preparation methods for adiponitrile were introduced in the article, such as butadiene method, acrylonitrile electrolytic dimerization method and adipic acid ammoniation method. In addition, the application feasibility of process intensification technology in acrylonitrile electrolytic dimerization method and adipic acid ammoniation method were discussed in depth from the view of reaction mechanism in the review. Finally, the kinetics and thermodynamics of adipic acid ammoniation were summarized. The application of the process intensification technology would be the key to promoting efficient and green production of adiponitrile, which was of great significance for the improvement and autonomy of adiponitrile production technology.

Key words: adipic acid ammoniation method, butadiene method, acrylonitrile electrolytic dimerization method, adiponitrile, process intensification, organic compounds, chemical processes, reaction kinetics

中图分类号:

TQ226.6

杜磊, 曹志涛, 许浪, 张英杰, 孙宝昌, 邹海魁, 初广文, 陈建峰. 己二腈制备方法的研究进展[J]. 化工进展, 2025, 44(7): 3683-3696.

DU Lei, CAO Zhitao, XU Lang, ZHANG Yingjie, SUN Baochang, ZOU Haikui, CHU Guangwen, CHEN Jianfeng. Progress research in preparation of adiponitrile[J]. Chemical Industry and Engineering Progress, 2025, 44(7): 3683-3696.

图/表 14

图1 丁二烯氯化氰化法生产己二腈流程[6]1—预混合器；2—氯化反应器；3—储槽；4—水洗塔；5、6、11、14—蒸馏塔；7—氢氰化反应器；8—分离塔；9—萃取塔；10—汽提塔；12—蒸发器；13—常压加氢塔

图2 丁二烯直接氢氰化法生产己二腈流程[6]1—丁二烯氢氰化反应器；2、7、10—过滤器；3—蒸发器；4、5、11、13、14、15—精馏塔；6—蒸发装置；8—异构化装置；9—氢氰化反应器；12—溶剂回收塔

图3 丁二烯法制备己二腈反应机理

图4 丙烯腈电解二聚法生产己二腈生产流程[12]1—支撑电解质量槽；2—磷酸钾量槽；3—丙烯腈量槽；4—电解槽；5、14—冷却器；6、8—洗涤塔；7—相分离塔；9、11—精馏塔；10—丙烯腈/水共沸物收集器；12—蒸馏塔；13—丙腈收集器；15—己二腈收集器

图5 丙烯腈电解二聚法制备己二腈的反应机理

表1 丙烯腈电解二聚法生产己二腈的不同工艺条件的对比

时间/年	阴极材料	阳极材料	支撑电解质种类	电流密度/kA·m^-2	己二腈选择性/%	参考文献
1964	汞池/铅	铂丝	四乙基对甲苯磺酸铵	—	—	[25]
1984	铅	镀铂钛	四乙基硫酸铵	50	93	[26]
1990	铬	软钢	EDTA和四丁基氢氧化铵乳液	2	78	[37]
2011	铅	DSA-O₂^①	四甲基氯化铵乳液	1	65	[35]
2012	铅	DSA-O₂	四甲基氯化铵乳液	4	78	[29]
2020	铬	铂网	EDTA和TAA	-20	93	[34]

图6 己二酸氨化气相法制备己二腈工艺流程[42]

图7 己二酸氨化液相法制备己二腈工艺流程[43]

图8 己二酸氨化法制备己二腈的单分子反应机理

图9 己二酸氨化法制备己二腈的双分子反应机理

表2 中和反应体系中各物质在298.15K时的热力学参数[50]

物质	Δ_fH $m ⊖$ /kJ·mol^-1
己二酸	-983.298
氨气	-46.99
己二酰胺	-596.528
水	-242.66
己二腈	68.2

表2 中和反应体系中各物质在298.15K时的热力学参数[50]

物质	Δ_fH $m ⊖$ /kJ·mol^-1
己二酸	-983.298
氨气	-46.99
己二酰胺	-596.528
水	-242.66
己二腈	68.2

表3 在298.15K时己二酸氨化过程的ΔrHm⊖

反应过程	Δ_rH $m ⊖$ /kJ·mol^-1
中和反应	-4.57
脱水反应	179.408
总反应过程	174.838

表3 在298.15K时己二酸氨化过程的ΔrHm⊖

反应过程	Δ_rH $m ⊖$ /kJ·mol^-1
中和反应	-4.57
脱水反应	179.408
总反应过程	174.838

表4 中和反应体系中各物质在523.15K时的热力学参数

物质	Δ_fH $m ⊖$ /kJ·mol^-1
己二酸（液体）	-870.048
氨气	-36.49
己二酰胺（液体）	-503.28
水（气体）	-233.85
己二腈	139.45

表4 中和反应体系中各物质在523.15K时的热力学参数

物质	Δ_fH $m ⊖$ /kJ·mol^-1
己二酸（液体）	-870.048
氨气	-36.49
己二酰胺（液体）	-503.28
水（气体）	-233.85
己二腈	139.45

表5 在523.15K时己二酸氨化过程的ΔrHm⊖

反应过程	Δ_rH $m ⊖$ /kJ·mol^-1
中和反应	-27.95
脱水反应	175.03
总反应过程	147.08

表5 在523.15K时己二酸氨化过程的ΔrHm⊖

反应过程	Δ_rH $m ⊖$ /kJ·mol^-1
中和反应	-27.95
脱水反应	175.03
总反应过程	147.08

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己二腈制备方法的研究进展

Progress research in preparation of adiponitrile

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