分子筛稳定的Lewis酸稀土中心在醛自缩合反应中的应用

doi:10.1016/S1872-2067(20)63675-0

催化学报 ›› 2021, Vol. 42 ›› Issue (4): 595-605.DOI: 10.1016/S1872-2067(20)63675-0

分子筛稳定的Lewis酸稀土中心在醛自缩合反应中的应用

颜婷婷^a, 姚思凯^a, 戴卫理^a^,^*(), 武光军^a, 关乃佳^a^,^b, 李兰冬^a^,^b^,^#()

^a南开大学材料科学与工程学院, 天津300350
^b南开大学先进能源材料化学教育部重点实验室, 化学化工协同创新中心, 天津300071

收稿日期:2020-05-17 接受日期:2020-06-28 出版日期:2021-04-18 发布日期:2021-01-22
通讯作者: 戴卫理,李兰冬
基金资助:
国家自然科学基金(21872072);天津市自然科学基金(18JCZDJC37400);天津市自然科学基金(18JCJQJC47400);中国石化(419040)

Self-aldol condensation of aldehydes over Lewis acidic rare-earth cations stabilized by zeolites

Tingting Yan^a, Sikai Yao^a, Weili Dai^a^,^*(), Guangjun Wu^a, Naijia Guan^a^,^b, Landong Li^a^,^b^,^#()

^aSchool of Materials Science and Engineering, Nankai University, Tianjin 300350, China
^bKey Laboratory of Advanced Energy Materials Chemistry of the Ministry of Education, Nankai University, Tianjin 300071, China

Received:2020-05-17 Accepted:2020-06-28 Online:2021-04-18 Published:2021-01-22
Contact: Weili Dai,Landong Li
About author:^#Tel/Fax: +86-22-23500341; E-mail: lild@nankai.edu.cn
^*Tel/Fax: +86-22-85358536; E-mail: weilidai@nankai.edu.cn;
Supported by:
National Natural Science Foundation of China(21872072);Municipal Natural Science Foundation of Tianjin(18JCZDJC37400);Municipal Natural Science Foundation of Tianjin(18JCJQJC47400);SINOPEC(419040)

摘要/Abstract

摘要：

羟醛缩合是重要的C-C键偶联反应, 可以增长碳链, 降低O/C比, 用于生产很多大宗化学品, 在生物质转化和生物油升级中广受关注. 本文以丙醛分子自缩合反应作为模型反应, 对比研究了稀土分子筛和稀土氧化物在醛自缩合反应中的催化性能, 发现稀土分子筛的活性远高于稀土氧化物, 其中Y/Beta活性最佳, 并且具有良好的循环性能. 随后采用程序升温表面反应(TPSR)、原位漫反射红外光谱(in situ DRIFTS)和原位漫反射紫外光谱(in situ UV-vis DRS)对Y/Beta和Y₂O₃催化丙醛缩合反应过程进行对比研究. TPSR结果表明, Y/Beta催化剂的反应能垒比Y₂O₃低; 通过原位DRIFTS和UV-vis DRS谱结果发现, Y/Beta催化剂上Lewis酸位点对丙醛分子具有较强的吸附能力, 利于缩合反应的进行, 而Y₂O₃上几乎没有产物的特征峰, 但出现芳香烃物种的吸收峰, 表明Y₂O₃比Y/Beta催化剂更容易形成积碳物种, 从而造成催化剂失活. 我们还通过密度泛函理论(DFT)对Y/Beta分子筛的结构及其催化羟醛缩合反应过程进行计算模拟, 揭示了羟醛缩合的主要反应步骤, 即醛经历烯醇异构化、亲核加成和羟醛二聚体脱水等关键步骤, 其中羟醛二聚体脱水是决速步. 此外, 具有开放结构的Y中心的催化活性比闭合结构的更高, 其羟基可以通过氢键有效稳定羟醛二聚体的过渡态, 从而降低其转化能垒, 并且羟基的数量越多, 能垒越低. 因此, 具有Lewis酸位点的Y(OSi)(OH)₂是羟醛缩合反应的主要活性中心.
综上, [Si]Beta分子筛对活性位点Y-OH的稳定作用, Y-OH是反应的活性位点, 能够显著降低反应的能垒, 而分子筛的限域作用可以有效控制中间物种的扩散, 从而进一步促进羟醛缩合反应的进行. 醛在反应过程中首先吸附在Y-OH位点上, 经历α-C-H键的裂化, 转变成烯醇式结构; 裂化产生的氢原子和Y-OH中的羟基作用能够大大降低活化能垒; 烯醇式离子和另一分子醛自发发生亲核加成反应生成醇盐离子, 生成的醇盐离子与烯醇异构化反应中裂化的氢原子发生质子化反应, 从而得到羟醛二聚体; 最后, 羟醛二聚体吸附在Y-OH上, 通过氢键稳定过渡态, 降低了活化能垒, 诱发脱水反应生成最终产物.

关键词: 羟醛自缩合反应, 醛, 稀土中心, 分子筛, Lewis酸

Abstract:

The self-aldol condensation of aldehydes was investigated with rare-earth cations stabilized by [Si]Beta zeolites in parallel with bulk rare-earth metal oxides. Good catalytic performance was achieved with all Lewis acidic rare-earth cations stabilized by zeolites and yttrium appeared to be the best metal choice. According to the results of several complementary techniques, i.e., temperature-programmed surface reactions, in situ diffuse reflectance infrared Fourier transform spectroscopy, ultraviolet-visible diffuse reflectance spectroscopy, the reaction pathway and mechanism of the aldehyde self-aldol condensation over Y/Beta catalyst were studied in more detail. Density functional theory calculations revealed that aldol dehydration was the rate-limiting step. The hydroxyl group at the open yttrium site played an important role in stabilizing the transition state of the aldol dimer reducing the energy barrier for its hydration. Lewis acidic Y(OSi)(OH)₂ stabilized by zeolites in open configurations were identified as the preferred active sites for the self-aldol condensation of aldehydes.

Key words: Self-aldol condensation, Aldehyde, Rare-earth cations, Zeolite, Lewis acid

颜婷婷, 姚思凯, 戴卫理, 武光军, 关乃佳, 李兰冬. 分子筛稳定的Lewis酸稀土中心在醛自缩合反应中的应用[J]. 催化学报, 2021, 42(4): 595-605.

Tingting Yan, Sikai Yao, Weili Dai, Guangjun Wu, Naijia Guan, Landong Li. Self-aldol condensation of aldehydes over Lewis acidic rare-earth cations stabilized by zeolites[J]. Chinese Journal of Catalysis, 2021, 42(4): 595-605.

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链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(20)63675-0

https://www.cjcatal.com/CN/Y2021/V42/I4/595

图/表 16

Fig. 1. Self-aldol condensation of propyl aldehyde over different catalysts. Reaction conditions: 0.16 g catalyst, WHSV = 1.0/h, T = 573 K, TOS = 2 h.

Fig. 2. Propyl aldehyde conversion with time-on-stream of Y/Beta, La/Beta, Sc/Beta and Ce/Beta catalysts. Reaction conditions: 0.16 g catalyst, WHSV = 1.0/h, T = 573 K; Regeneration conditions: calcination in flowing air at 773 K for 4 h.

Table 2 Summary of IR bands observed and their assignments.

IR bands	Assignments
3734 cm^-1	O-H stretching vibrations of Si-OH
3672 cm^-1	O-H stretching vibrations of Y-OH
3000-2700 cm^-1	C-H stretching vibrations of methyl and methylene groups
1741 cm^-1	C=O stretching vibrations of chemisorbed aldehydes
1765 cm^-1	C=O stretching vibrations of gas phase aldehydes
1687 cm^-1	C=O stretching vibrations of α,β-unsaturated carbonyl groups
1643 cm^-1	C=C stretching vibrations of α,β-unsaturated carbonyl groups
1608 &1597 cm^-1	C=C stretching vibrations of carbonaceous or aromatics species
1462 cm^-1	C-H bending vibrations of aromatic ring
1456 & 1404 cm^-1	C-H bending vibrations of aldehyde or aldol dimer
1305 & 1174 cm^-1	Aldehyde molecules coordinated to Lewis acid sites

Table 1 Physicochemical properties of zeolites.

Catalyst	n_si/n_Al^a	Surface area ^b (m²/g)	Pore volume ^c (cm³/g)
H-Beta	14	562	0.194
[Si]Beta	> 1800	581	0.206
Y/Beta	> 1800	527	0.171
La/Beta	> 1800	524	0.170
Ce/Beta	> 1800	532	0.174
Sc/Beta	> 1800	531	0.172

Fig. 3. DRIFTS in the hydroxyl regions of selected zeolite samples.

Fig. 4. 13C CPMAS NMR spectra of zeolite samples after acetone-2-13C adsorption.

Fig. 5. In situ DRIFTS recorded during propyl aldehyde conversion over Y/Beta and Y2O3 for TOS of 60 min. Reaction conditions: WHSV = 1.0/h, T = 573 K.

Fig. 6. In situ UV-vis DRS recorded during propyl aldehyde conversion over Y/Beta and Y2O3 for TOS of 60 min. Reaction conditions: WHSV = 0.3/h, T = 573 K.

Fig. 7. TPSR profiles of propyl aldehyde conversion over Y/Beta and Y2O3 catalysts. Reaction conditions: 0.16 g catalyst, WHSV = 1.0/h.

Fig. 8. Optimized structures of Y/Beta. The active sites in Y/Beta-I and Y/Beta-II are Y(OSi)3 and Y(OSi)2(OH), respectively. (cyan: Y; yellow: Si; red: O; white: H).

Table 3 Energy barriers (Ea) and reaction energies (ΔE) for keto-enol tautomerization of various models.

Entry	Model	E_a (eV)	ΔE (eV)
P1	Y/Beta-I	1.07	0.10
P2	Y/Beta-II^a	1.01	0.49
P3	Y/Beta-II^b	0.82	0.38

Table 4 Energy barriers and reaction energies of alkoxy anion hydrogenation on various models.

Entry	Model	E_a (eV)	ΔE (eV)
P1	Y/Beta-I	0.61	0.01
P2	Y/Beta-II^a	0.33	-0.31
P3	Y/Beta-II^b	—	-0.32

Table 5 Energy barriers and reaction energies for aldol dimer dehydration on various models.

Entry	Model	E_a (eV)	ΔE (eV)
P1	Y/Beta-I	2.24	0.35
P2	Y/Beta-II^a	2.30	0.37
P3	Y/Beta-II^b	1.63	0.15
Gas phase		2.00	0.19

Fig. 9. Configurations of initial and transition states of aldol dimer dehydration on Y/Beta-I and Y/Beta-II. (cyan: Y; yellow: Si; red: O; gray: C; white: H).

Fig. 10. Energy profiles of acetaldehyde self-aldol condensation over Y/Beta. Three distinct reaction pathways (P1, P2 and P3) are considered.

Scheme 1. Reaction pathway and mechanism of the self-aldol condensation of aldehydes over Y/Beta.

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分子筛稳定的Lewis酸稀土中心在醛自缩合反应中的应用

Self-aldol condensation of aldehydes over Lewis acidic rare-earth cations stabilized by zeolites

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