SnCl2促进的Pt1/PS-PPh2催化剂高选择性催化高碳烯烃氢甲酰化反应

doi:10.1016/S1872-2067(24)60029-X

催化学报 ›› 2024, Vol. 60: 316-326.DOI: 10.1016/S1872-2067(24)60029-X

SnCl₂促进的Pt₁/PS-PPh₂催化剂高选择性催化高碳烯烃氢甲酰化反应

虞周楠^a^,^b, 张磊磊^a^,^*(), 谈源龙^a^,^b, 井日峥^a^,^b, 曹宏晨^a^,^b, 楼才溢^b^,^c, 格日乐^a^,^d, 王军虎^a^,^d, 王爱琴^a^,^*(), 张涛^a

^a中国科学院大连化学物理研究所, 中国科学院应用催化科学技术重点实验室, 辽宁大连 116023
^b中国科学院大学, 北京 100049
^c中国科学院大连化学物理研究所, 低碳催化技术国家工程研究中心, 辽宁大连 116023
^d中国科学院大连化学物理研究所, 穆斯堡尔谱数据中心, 辽宁大连 116023

收稿日期:2024-02-07 接受日期:2024-03-28 出版日期:2024-05-18 发布日期:2024-05-20
通讯作者: *电子信箱: aqwang@dicp.ac.cn (王爱琴), zhangleilei@dicp.ac.cn (张磊磊).
基金资助:
国家重点研发计划(2023YFA1506603);国家自然科学基金(22132006);国家自然科学基金(22172159);国家自然科学基金基础科学中心项目(22388102);中国科学院稳定支持基础研究领域青年团队计划(YSBR-022);中国科学院青年创新促进会(2022185)

PS-PPh₂ tethered Pt single atoms promoted by SnCl₂ as highly efficient and regio-selective catalysts for the hydroformylation of higher α-alkenes

Zhounan Yu^a^,^b, Leilei Zhang^a^,^*(), Yuanlong Tan^a^,^b, Rizheng Jing^a^,^b, Hongchen Cao^a^,^b, Caiyi Lou^b^,^c, Rile Ge^a^,^d, Junhu Wang^a^,^d, Aiqin Wang^a^,^*(), Tao Zhang^a

^aCAS Key Laboratory of Science and Technology on Applied Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^bUniversity of Chinese Academy of Sciences, Beijing 100049, China
^cNational Engineering Research Center of Lower-Carbon Catalysis Technology, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China
^dMössbauer Effect Data Center, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2024-02-07 Accepted:2024-03-28 Online:2024-05-18 Published:2024-05-20
Contact: *E-mail: zhangleilei@dicp.ac.cn (L. Zhang), aqwang@dicp.ac.cn (A. Wang).
Supported by:
National Key R&D Program of China(2023YFA1506603);National Natural Science Foundation of China(22132006);National Natural Science Foundation of China(22172159);National Natural Science Foundation of China Center for Single-Atom Catalysis(22388102);CAS Project for Young Scientists in Basic Research(YSBR-022);Youth Innovation Promotion Association CAS(2022185)

摘要/Abstract

摘要：

氢甲酰化作为工业上制备醛、醇等含氧化合物的重要反应, 广泛应用于制备洗涤剂、增塑剂、表面活性剂和香料等. 目前, 氢甲酰化反应主要使用HCo(CO)₄, HCo(CO)₃(PR₃)和HRh(CO)(PPh₃)₂等配合物作为催化剂. 尽管Co基催化剂可以将高碳烯烃、内烯烃以及支链烯烃高选择性地转化为直链醛, 但其反应条件 (5‒30 MPa, 140‒200 °C)较苛刻, 且容易发生烯烃加氢等副反应. 相比之下, Rh催化剂的活性比Co基催化剂高1‒2个数量级, 且反应条件较为温和. 但Rh储量稀少, 价格昂贵, 而且对于高碳烯烃氢甲酰化反应, Rh催化剂难以分离和循环使用. 因此, 研究者开展了其他金属催化剂的研究, 其中Pt-Sn催化剂因其出色的区域选择性而备受关注. 但目前Pt-Sn催化剂多局限于均相催化体系, 而且Sn助剂的作用尚不明确.

本文采用商业化三苯基膦嫁接的聚苯乙烯小球为载体, 通过浸渍法制备了SnCl₂-Pt₁/PS-PPh₂单原子催化剂, 考察了其在长链-烯烃氢甲酰化反应中的催化性能, 并研究了Sn的促进作用. 首先, 以1-己烯氢甲酰化为探针反应, 对催化剂的组成以及反应条件进行了优化. 当Pt/P/Sn=1/2/5时, 催化剂表现出最高的催化活性, 在90‒120 °C和4‒6 MPa合成气条件下, 催化剂转化频率(TOF)为40 h^‒1, 产物醛的正异比> 42. 随后, 考察了催化剂的底物适用性. 结果表明, C₆‒C₁₂的高碳烯烃均可被高选择性地转化为相应的醛(正异比> 20). 然而, 在循环使用实验中, 由于SnCl₂不能稳定锚定在载体上, 第二次循环时催化活性降低. 但通过补加SnCl₂, 催化活性可以完全恢复. 高压热过滤实验及元素检测结果表明, 反应过程中Pt没有流失. X-射线吸收光谱(XAFS)表征结果表明, 反应后Pt仍以单原子形式存在, 说明Pt₁/PS-PPh₂具有良好的稳定性. 通过准原位X-射线吸收谱、Mössbauer谱和红外光谱表征对反应过程中Pt和Sn的电子性质和配位结构进行了研究. 结果表明, SnCl₂在反应过程中逐渐转化为Sn(dioxane)Cl₃^‒物种(1,4-二氧六环为反应溶剂), 并与Pt原子形成Pt-Sn键. 当反应体系中没有Sn时, Pt(II)会被合成气过度还原并发生团聚. 当没有膦配体时, Pt原子也会发生聚集, 而且SnCl₂会在Pt(II)的催化作用下发生水解生成SnO. 因此Sn(dioxane)Cl₃^‒与膦配体共同抑制了Pt(I)在反应过程中的还原与聚集. 最后, 通过XAFS表征深入研究了反应机理. 分析结果表明, CO在催化剂上具有较强的吸附作用, 而H₂则可能以异裂的方式在催化剂上被活化. 据此提出可能的反应机理: 首先, H₂在催化剂上活化先形成Pt-H物种; 随后, 烯烃插入Pt-H, 形成Pt-烷基物种; 接着, CO迁移并插入, 生成Pt-酰基物种; 最后, 经过还原消除步骤, 得到最终的产物醛.

综上, 本文制备了一种对高碳烯烃氢甲酰化反应具有良好催化性能的SnCl₂-Pt₁/PS-PPh₂单原子催化剂, 为低成本非Rh基催化剂的开发提供借鉴. 同时, 揭示了催化体系中Sn的促进作用, 为通过Lewis酸来调控催化剂的性能提供了参考.

关键词: 氢甲酰化反应, 铂-锡催化剂, 高碳烯烃, 区域选择性, 单原子催化剂

Abstract:

Rh-P complexes have been widely used as catalysts for hydroformylation reactions. The extremely high price of Rh and its scarce reserves have prompted the exploration of the alternatives. In this study, we reported that Pt/PS-PPh₂ single-atom catalysts promoted by SnCl₂ were highly efficient and selective for the hydroformylation of higher α-alkenes. A broad scope of substrates (i.e., C₆‒C₁₂) were smoothly converted to the corresponding linear aldehydes with high yields under reaction conditions of 90‒120 °C and 4‒6 MPa syngas. The turnover frequency (TOF) was comparable to homogeneous Pt-Sn catalysts, and the linear/branched ratio reached as high as > 20. In addition, the catalyst could be reused with the extra addition of SnCl₂. The promotional role of SnCl₂ was elucidated by quasi-in situ X-ray adsorption fine structure, Fourier transform infrared, and Mössbauer spectroscopy. It was discovered that SnCl₂ was transformed into Sn(dioxane)Cl₃^‒ species coordinated to Pt as a moderately electron-donating ligand, which, together with the phosphine group, stabilized mononuclear Pt (I) species against reduction and aggregation.

Key words: Hydroformylation reaction, Platinum-tin catalyst, Higher alkenes, Regio-selectivity, Single-atom catalyst

虞周楠, 张磊磊, 谈源龙, 井日峥, 曹宏晨, 楼才溢, 格日乐, 王军虎, 王爱琴, 张涛. SnCl₂促进的Pt₁/PS-PPh₂催化剂高选择性催化高碳烯烃氢甲酰化反应[J]. 催化学报, 2024, 60: 316-326.

Zhounan Yu, Leilei Zhang, Yuanlong Tan, Rizheng Jing, Hongchen Cao, Caiyi Lou, Rile Ge, Junhu Wang, Aiqin Wang, Tao Zhang. PS-PPh₂ tethered Pt single atoms promoted by SnCl₂ as highly efficient and regio-selective catalysts for the hydroformylation of higher α-alkenes[J]. Chinese Journal of Catalysis, 2024, 60: 316-326.

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Entry	Pt loading (wt%)	Sn: Pt (molar ratio)	Conv. (%)	Yield (%)					l:b	δ (%)
Entry	Pt loading (wt%)	Sn: Pt (molar ratio)	Conv. (%)	Hexane	Isomer	a	b	c	l:b	δ (%)
1	0	—^b	0.9	0	0.6	0	0	0	—	−0.3
2	0.9	5	1.5	0	0.5	0	0	0	—	−1.0
3	2.9	5	19.2	0.3	1.7	10.7	0	0	linear	−6.4
4	4.7	5	93.2	3.6	13.1	70.8	1.7	0	42.2	−4.2
5	7.7	5	91.3	3.9	12.8	76.9	1.2	0	64.6	3.5
6	4.7	0	6.9	0	0.6	0	0	0	—	−6.3
7	4.7	2.5	65.8	1.2	4.4	55.4	0	0	linear	−4.8
8	4.7	10	83.1	2.3	7.7	71.1	0.6	0	118	−1.3
9	4.7	5(Fe)	4.7	0	0.6	0	0	0	—	−4.1
10	4.7	5(Au)	7.1	0	0.6	0	0	0	—	−6.5
11	4.7	5(Zn)	4.1	0	0.7	0	0	0	—	−3.4
12	8(Pd) ^c	5	91.1	0	85.9	0	0	0	—	−5.2
13	8(Pd) ^c	5(Fe)	18.2	0.1	12.2	0	0	0	—	−6.0
14	8(Rh) ^c	—	96.6	0.2	1.4	75.6	23.3	0	3.2	+3.9
15	8(Rh) ^c	5	99.6	0.2	17.2	54.4	30.0	7.7	1.1	−2.7

Entry	Pt loading (wt%)	Sn: Pt (molar ratio)	Conv. (%)	Yield (%)					l:b	δ (%)
Entry	Pt loading (wt%)	Sn: Pt (molar ratio)	Conv. (%)	Hexane	Isomer	a	b	c	l:b	δ (%)
1	0	—^b	0.9	0	0.6	0	0	0	—	−0.3
2	0.9	5	1.5	0	0.5	0	0	0	—	−1.0
3	2.9	5	19.2	0.3	1.7	10.7	0	0	linear	−6.4
4	4.7	5	93.2	3.6	13.1	70.8	1.7	0	42.2	−4.2
5	7.7	5	91.3	3.9	12.8	76.9	1.2	0	64.6	3.5
6	4.7	0	6.9	0	0.6	0	0	0	—	−6.3
7	4.7	2.5	65.8	1.2	4.4	55.4	0	0	linear	−4.8
8	4.7	10	83.1	2.3	7.7	71.1	0.6	0	118	−1.3
9	4.7	5(Fe)	4.7	0	0.6	0	0	0	—	−4.1
10	4.7	5(Au)	7.1	0	0.6	0	0	0	—	−6.5
11	4.7	5(Zn)	4.1	0	0.7	0	0	0	—	−3.4
12	8(Pd) ^c	5	91.1	0	85.9	0	0	0	—	−5.2
13	8(Pd) ^c	5(Fe)	18.2	0.1	12.2	0	0	0	—	−6.0
14	8(Rh) ^c	—	96.6	0.2	1.4	75.6	23.3	0	3.2	+3.9
15	8(Rh) ^c	5	99.6	0.2	17.2	54.4	30.0	7.7	1.1	−2.7

Entry	Reactant	T (°C)	Conv. (%)	Yield (%)					l:b	δ(%)
Entry	Reactant	T (°C)	Conv. (%)	Alkane	Isomer	a	b	c	l:b	δ(%)
1		90	37.8	1.2	4.6	30.6	0	0	linear	−1.4
2		90 ^b	93.2	3.6	13.1	70.8	1.7	0	42.2	−4.2
3		120 ^c,d	24.0	0.5	2.8	16.9	0	0	linear	−3.9
4		120 ^e	26.0	0.2	4.1	20.5	0.9	0	22.8	−0.3
5		90	27.1	2.5	3.0	18.5	0	0	linear	−3.0
6		120	71.1	7.6	23.4	34.8	1.6	0	22	−3.7
7		120 ^c,d	23.7	1.7	5.9	11.9	0.3	0	39.7	−3.9
8		90	20.8	2.7	2.7	11.1	0	0	linear	−4.3
9		120	72.5	7.0	29.1	29.9	1.5	0	20	−4.9
10		120 ^c,d	23.1	2.2	7.1	11.1	0.3	0	37.0	−2.3
11		90 ^f	74.5	10.7	29.9	34.2	3.1	0	10.9	+3.4
12		120 ^f	65.4	4.9	6.8	56.9	2.9	0	19.6	+5.1
13		120 ^d,g	31.8	5.3	6.5	21.0	1.1	0	19.6	+2.0
14		120 ^h	85.6	12.5	50.2	23.9	2.7	0	8.8	+3.8
15		120 ⁱ	56.4	3.8	3.0	49.0	2.0	0	25	+1.4
16		90 ^b	99.7	2.8	8.1	36.9 ^j 54.1 ^k	0	0	linear	+2.1
17		90 ^b	5.6	4.7	0	0	0	0	—	−0.9

Entry	Reactant	T (°C)	Conv. (%)	Yield (%)					l:b	δ(%)
Entry	Reactant	T (°C)	Conv. (%)	Alkane	Isomer	a	b	c	l:b	δ(%)
1		90	37.8	1.2	4.6	30.6	0	0	linear	−1.4
2		90 ^b	93.2	3.6	13.1	70.8	1.7	0	42.2	−4.2
3		120 ^c,d	24.0	0.5	2.8	16.9	0	0	linear	−3.9
4		120 ^e	26.0	0.2	4.1	20.5	0.9	0	22.8	−0.3
5		90	27.1	2.5	3.0	18.5	0	0	linear	−3.0
6		120	71.1	7.6	23.4	34.8	1.6	0	22	−3.7
7		120 ^c,d	23.7	1.7	5.9	11.9	0.3	0	39.7	−3.9
8		90	20.8	2.7	2.7	11.1	0	0	linear	−4.3
9		120	72.5	7.0	29.1	29.9	1.5	0	20	−4.9
10		120 ^c,d	23.1	2.2	7.1	11.1	0.3	0	37.0	−2.3
11		90 ^f	74.5	10.7	29.9	34.2	3.1	0	10.9	+3.4
12		120 ^f	65.4	4.9	6.8	56.9	2.9	0	19.6	+5.1
13		120 ^d,g	31.8	5.3	6.5	21.0	1.1	0	19.6	+2.0
14		120 ^h	85.6	12.5	50.2	23.9	2.7	0	8.8	+3.8
15		120 ⁱ	56.4	3.8	3.0	49.0	2.0	0	25	+1.4
16		90 ^b	99.7	2.8	8.1	36.9 ^j 54.1 ^k	0	0	linear	+2.1
17		90 ^b	5.6	4.7	0	0	0	0	—	−0.9

Sample	Path	R (Å)	N	ΔE₀ (eV)	σ² (10^-3 Å²)	R factor (%)
Pt foil	Pt-Pt	2.77+/−0.00	12 ^b	7.9+/−0.3	5+/−0	0.2
PtSn₂	Pt-C/O	2.02+/−0.01	7 ^c	5.0+/−0.9	4+/−1 ^d	1.4
	Pt-Sn	2.63+/−0.02	1.0+/−0.3		4+/−1 ^d
	Pt-(C)-Pt	2.93+/−0.02	2.2+/−0.6		5+/−1
Pt(PPh₃)₂	Pt-C/O	2.03+/−0.02	4 ^c	5.1+/−1.5	9+/−2	1.8
	Pt-P	2.25+/−0.02	1 ^c		9+/−3 ^d
	Pt-Pt	2.75+/−0.02	2.4+/−0.5		9+/−3 ^d
PtSn₂(PPh₃)₂	Pt-C/O	2.02+/−0.02	4 ^c	4.4+/−1.4	9+/−3 ^d	2.1
	Pt-P	2.35+/−0.02	1 ^c		9+/−3 ^d
	Pt-Sn	2.64+/−0.02	1.2+/−0.4		9+/−3 ^d
Sn foil	Sn-Sn	3.00+/−0.01	8 ^b	5.2+/−0.7	10+/−1	0.5
PtSn₂(PPh₃)₂	Sn-C/O	2.09+/−0.02	0.7+/−0.3	6.5+/−2.1	7+/−1 ^d	1.1
	Sn-Cl	2.42+/−0.02	3 ^c		7+/−1 ^d
	Sn-Pt	2.66+/−0.05	0.5+/−0.1		7+/−1 ^d

SnCl₂促进的Pt₁/PS-PPh₂催化剂高选择性催化高碳烯烃氢甲酰化反应

PS-PPh₂ tethered Pt single atoms promoted by SnCl₂ as highly efficient and regio-selective catalysts for the hydroformylation of higher α-alkenes

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