Research progress on alkyl naphthalene synthesis catalysts

doi:10.16085/j.issn.1000-6613.2025-0373

Abstract

Abstract:

Alkyl naphthalenes, as important organic chemical intermediates and high-performance materials, are primarily synthesized through alkylation reactions. Conventional liquid acid catalysts are limited by their strong corrosiveness and environmental pollution. In contrast, solid acid catalysts like zeolites have become research hotspots due to their environmental-friendliness and recyclability. This paper reviews the research progress of alkyl naphthalene synthesis catalysts, focusing on zeolite catalysts and their performance regulation. Comparisons of different catalysts’ adaptability to reaction conditions reveal that reactions catalyzed by liquid acids and ionic liquids require milder conditions, while those by solid acids usually need higher temperatures and longer reaction times. For zeolites, acid treatment improves mass transfer and modulates acidity, while high-temperature water vapor treatment enhances mass transfer and coke-resistance and metal modification enables synergistic regulation of acidity and pore structure. Future research should focus on developing low-cost, high-activity, and long-life zeolite catalysts, and solving their regeneration problems to promote green alkyl naphthalene synthesis.

Key words: alkyl naphthalene synthesis, catalyst, molecular sieves, optimal design, green synthesis technology

摘要：

烷基萘是重要有机化工中间体和高性能材料，用途广泛，合成主要依靠烷基化反应。传统液体酸催化剂因腐蚀性强、环境污染等问题受限，而固体酸催化剂如分子筛等因其环保、可循环使用等优点成为了研究热点。本文综述烷基萘合成催化剂研究进展，重点阐述分子筛催化剂及其优化设计。通过对不同催化剂反应条件适应性比较，发现液体酸和离子液体反应条件较温和，而固体酸则通常需要更高的反应温度和更长的反应时间。针对分子筛，酸处理能够改善其传质性能并调变酸性；高温水蒸气处理可提升其传质与抗积炭能力；金属改性可实现对酸性和孔道结构的协同调控。未来需要开发低成本、高活性、长寿命的分子筛催化剂，并解决其再生问题，以推动烷基萘绿色合成技术的发展。

关键词: 烷基萘合成, 催化剂, 分子筛, 优化设计, 绿色合成技术

CLC Number:

TQ241.5

LIU Zhe, ZHOU Shunli, LI Yongxiang, ZHANG Chengxi, LIU Yipeng. Research progress on alkyl naphthalene synthesis catalysts[J]. Chemical Industry and Engineering Progress, 2025, 44(S1): 144-158.

刘哲, 周顺利, 李永祥, 张成喜, 刘宜鹏. 烷基萘合成催化剂研究进展[J]. 化工进展, 2025, 44(S1): 144-158.

Figures/Tables 13

催化剂类型	催化剂名称	烷基化试剂	反应温度/℃	反应压力/MPa	反应时间/h	参考文献
无机酸	AlCl₃	十一烯/十二烯	40	0	0.5	[29]
有机酸	CH₃SO₃H	辛烯	80	0	3	[31]
有机酸	CF₃SO₃H	十二烯	80	0	1	[33]
离子液体	Et₃NHCl-AlCl₃	辛烯	60	0	1	[35]
离子液体	Et₃NHCl-AlCl₃	十四烯	60	0	0.5	[36]
固体超强酸	SO $4 2 -$ /TiO₂	十四烯	100	0	5	[39]
杂多酸	硅钨酸/ZrO₂	辛烯	80	0	4	[41]
杂多酸	磷钨酸/SiO₂	十六烯	130	0	1	[42]
分子筛	HY	十一烯/十二烯	130	1	6	[51]
分子筛	HY	十四烯	175	1	3	[52]
分子筛	HY	十四烯	175	0.5	6	[22]
分子筛	HY	十二烯	210	0	4	[53]
分子筛	HY	十八烯	190	0	4	[53]

催化剂类型	催化剂名称	烷基化试剂	反应温度/℃	反应压力/MPa	反应时间/h	参考文献
无机酸	AlCl₃	十一烯/十二烯	40	0	0.5	[29]
有机酸	CH₃SO₃H	辛烯	80	0	3	[31]
有机酸	CF₃SO₃H	十二烯	80	0	1	[33]
离子液体	Et₃NHCl-AlCl₃	辛烯	60	0	1	[35]
离子液体	Et₃NHCl-AlCl₃	十四烯	60	0	0.5	[36]
固体超强酸	SO $4 2 -$ /TiO₂	十四烯	100	0	5	[39]
杂多酸	硅钨酸/ZrO₂	辛烯	80	0	4	[41]
杂多酸	磷钨酸/SiO₂	十六烯	130	0	1	[42]
分子筛	HY	十一烯/十二烯	130	1	6	[51]
分子筛	HY	十四烯	175	1	3	[52]
分子筛	HY	十四烯	175	0.5	6	[22]
分子筛	HY	十二烯	210	0	4	[53]
分子筛	HY	十八烯	190	0	4	[53]

改性方法	分子筛名称	酸性质调控	孔结构调控	催化性能影响	适用范围	参考文献
盐酸处理	HM	总酸量减少，强酸量占比提高	介孔体积与平均孔径增加、介孔孔径分布变宽	活性大幅提高，但不利于小分子产物的选择性生成	分子尺寸相对较大的烷基萘的合成	[57]
盐酸处理	HY	总酸量减少，强酸量占比提高	介孔体积与平均孔径增加、介孔孔径分布变宽	活性大幅提高，但不利于小分子产物的选择性生成	分子尺寸相对较大的烷基萘的合成	[58]
草酸处理	HY	酸量与酸强度均降低	—	活性降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[58]
高温水蒸气处理	HY	总酸量减少，强酸量占比提高	介孔体积与平均孔径增加、介孔孔径分布变宽	活性与稳定性大幅提高	长链烷基萘及多烷基萘的合成	[60-61]
钨金属改性	HY	总酸量减少，弱酸量占比提高，B酸和L酸比值降低	总孔体积与介孔体积均减小	活性与单烷基萘选择性均提高	单烷基萘的选择性生成	[64]
镁金属改性	USY	酸量与酸强度均降低	平均孔径减小	活性降低，但对2,6-二仲丁基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[65]
锌金属改性	USY	弱酸量增加，强酸量尤其是外表面强酸量大幅减少	介孔体积与平均孔径减小	活性提高，对2,6-二异丙基萘的选择性提高	2,6-二烷基萘的选择性生成	[66]
铜金属改性	HY	L酸量增加	孔径收缩	活性提高，对2,6-二异丙基萘的选择性提高	2,6-二烷基萘的选择性生成	[67]
铁金属改性	HY	强酸量与弱酸量均减少，中强酸量增加	总孔体积与平均孔径略微增加	活性略微降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[68]
铈金属改性	HY	酸量与酸强度均减少	总孔体积与介孔体积均减小，平均孔径减小	活性降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[69]
铈金属改性	HM	有效钝化外表面酸性位点	介孔体积均减小、平均孔径略微减小	活性降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[70-71]

改性方法	分子筛名称	酸性质调控	孔结构调控	催化性能影响	适用范围	参考文献
盐酸处理	HM	总酸量减少，强酸量占比提高	介孔体积与平均孔径增加、介孔孔径分布变宽	活性大幅提高，但不利于小分子产物的选择性生成	分子尺寸相对较大的烷基萘的合成	[57]
盐酸处理	HY	总酸量减少，强酸量占比提高	介孔体积与平均孔径增加、介孔孔径分布变宽	活性大幅提高，但不利于小分子产物的选择性生成	分子尺寸相对较大的烷基萘的合成	[58]
草酸处理	HY	酸量与酸强度均降低	—	活性降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[58]
高温水蒸气处理	HY	总酸量减少，强酸量占比提高	介孔体积与平均孔径增加、介孔孔径分布变宽	活性与稳定性大幅提高	长链烷基萘及多烷基萘的合成	[60-61]
钨金属改性	HY	总酸量减少，弱酸量占比提高，B酸和L酸比值降低	总孔体积与介孔体积均减小	活性与单烷基萘选择性均提高	单烷基萘的选择性生成	[64]
镁金属改性	USY	酸量与酸强度均降低	平均孔径减小	活性降低，但对2,6-二仲丁基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[65]
锌金属改性	USY	弱酸量增加，强酸量尤其是外表面强酸量大幅减少	介孔体积与平均孔径减小	活性提高，对2,6-二异丙基萘的选择性提高	2,6-二烷基萘的选择性生成	[66]
铜金属改性	HY	L酸量增加	孔径收缩	活性提高，对2,6-二异丙基萘的选择性提高	2,6-二烷基萘的选择性生成	[67]
铁金属改性	HY	强酸量与弱酸量均减少，中强酸量增加	总孔体积与平均孔径略微增加	活性略微降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[68]
铈金属改性	HY	酸量与酸强度均减少	总孔体积与介孔体积均减小，平均孔径减小	活性降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[69]
铈金属改性	HM	有效钝化外表面酸性位点	介孔体积均减小、平均孔径略微减小	活性降低，但对2,6-二异丙基萘的选择性显著提高	2,6-二烷基萘的选择性生成	[70-71]

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