N-Heterocyclic Carbene-Pyridine Molybdenum Complex Supported over SBA-15 for Converting of Carbon Dioxide into Cyclic Carbonates

doi:10.6023/cjoc202405037

Abstract

Synthesis of cyclic carbonates from carbon dioxide (CO₂) and epoxides is an effective pathway for the CO₂ utilization. Although various metal catalysts have been reported, it is highly desirable to develop a method for the reuse or recycling of catalysts. Herein, an N-heterocyclic carbene-pyridine molybdenum complex supported over SBA-15 (Mo@SBA- 15) was used as an efficient and recyclable catalyst for converting CO₂ and epoxides into cyclic carbonates. Mo@SBA-15 in combination with tetra-butylammonium bromide (TBAB) shows high catalytic activity in the synthesis of cyclic carbonates under 100 ℃ and 1 MPa CO₂ pressure. In addition, Mo@SBA-15 was reused seven times without any significant activity loss.

Key words: carbon dioxide, cyclic carbonate, molybdenum catalyst, CO₂ utilization, heterogeneous catalyst

Cite this article

Jianwen Li, Tao Wang, Sheng Tao, Fei Chen, Min Li, Ning Liu. N-Heterocyclic Carbene-Pyridine Molybdenum Complex Supported over SBA-15 for Converting of Carbon Dioxide into Cyclic Carbonates[J]. Chinese Journal of Organic Chemistry, 2024, 44(10): 3213-3222.

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Entry	Catalyst	C	N	H
1	SBA-15	0.46	—	1.52
2	Mo@SBA-15	7.79	1.01	0.954

Entry	Catalyst	C	N	H
1	SBA-15	0.46	—	1.52
2	Mo@SBA-15	7.79	1.01	0.954

Entry	Catalyst (mg)	Cocatalyst (mol%)	T/℃	p/MPa	Time/h	Yield/%
1	None	None	100	1	6	0
2	Mo@SBA-15 (50)	TBAB (3)	100	1	6	97
3	None	TBAB (3)	100	1	6	62
4	Mo@SBA-15 (50)	None	100	1	6	0
5	Mo complex 1a (50)	TBAB (3)	100	1	6	94
6	(3-Chloropropyl) trimethoxysilane (50)	TBAB (3)	100	1	6	46
7	SBA-15 (50)	TBAB (3)	100	1	6	71
8	Mo@SBA-15 (50)	TBAB (3)	30	1	6	27
9	Mo@SBA-15 (50)	TBAB (3)	60	1	6	52
10	Mo@SBA-15 (50)	TBAB (3)	80	1	6	73
11	Mo@SBA-15 (50)	TBAB (3)	100	0.5	6	70
12	Mo@SBA-15 (50)	TBAB (3)	100	1.5	6	88
13	Mo@SBA-15 (20)	TBAB (3)	100	1	6	87
14	Mo@SBA-15 (30)	TBAB (3)	100	1	6	94
15	Mo@SBA-15 (40)	TBAB (3)	100	1	6	96
16	Mo@SBA-15 (30)	TBAB (1)	100	1	6	49
17	Mo@SBA-15 (30)	TBAB (2)	100	1	6	82
18	Mo@SBA-15 (30)	TBAB (3)	100	1	2	71
19	Mo@SBA-15 (30)	TBAB (3)	100	1	4	82
20	Mo@SBA-15 (30)	TBAB (3)	100	1	10	97

Entry	Catalyst (mg)	Cocatalyst (mol%)	T/℃	p/MPa	Time/h	Yield/%
1	None	None	100	1	6	0
2	Mo@SBA-15 (50)	TBAB (3)	100	1	6	97
3	None	TBAB (3)	100	1	6	62
4	Mo@SBA-15 (50)	None	100	1	6	0
5	Mo complex 1a (50)	TBAB (3)	100	1	6	94
6	(3-Chloropropyl) trimethoxysilane (50)	TBAB (3)	100	1	6	46
7	SBA-15 (50)	TBAB (3)	100	1	6	71
8	Mo@SBA-15 (50)	TBAB (3)	30	1	6	27
9	Mo@SBA-15 (50)	TBAB (3)	60	1	6	52
10	Mo@SBA-15 (50)	TBAB (3)	80	1	6	73
11	Mo@SBA-15 (50)	TBAB (3)	100	0.5	6	70
12	Mo@SBA-15 (50)	TBAB (3)	100	1.5	6	88
13	Mo@SBA-15 (20)	TBAB (3)	100	1	6	87
14	Mo@SBA-15 (30)	TBAB (3)	100	1	6	94
15	Mo@SBA-15 (40)	TBAB (3)	100	1	6	96
16	Mo@SBA-15 (30)	TBAB (1)	100	1	6	49
17	Mo@SBA-15 (30)	TBAB (2)	100	1	6	82
18	Mo@SBA-15 (30)	TBAB (3)	100	1	2	71
19	Mo@SBA-15 (30)	TBAB (3)	100	1	4	82
20	Mo@SBA-15 (30)	TBAB (3)	100	1	10	97

Entry	Cat.	Nucleophile (mol%)	Epoxide	T/℃	Time/h	p/MPa	Yield/%	Runs
1^[51]	MoCl₅ (0.5 mol%)	PPh₃(3)	PO	r.t.	168	0.1	79.0	0
2^[52]	MoO₃ (2 mol%)	[Bu₄P]Br (2)	EMO	100	16	5	98.0	0
3^[53]	Mo catal. (1 mol%)	TBAB (7.2)	PO	25	24	0.1	97.5	0
4^[54]	Mo catal. (0.1 mol%)	Neat	ECH	100	3.5	1	56.3	0
5^[55]	Mo catal. (0.5 mol%)	TBAI (2)	EB	30	24	0.5	94.0	0
6^[56]	Mo catal. (0.15 mol%)	TBAB (5)	ECH	70	3	0.1	99.9^b	5
7^[57]	Mo catal. (0.1 mmol)	TBAB (1)	SO	50	48	0.5	99.0^b	3
8^[49]	Mo catal. (0.5 mol%)	TBAI (2)	EB	80	20	0.5	91.0	0
9 (our work)	Mo@SBA-15 (30 mg)	TBAB (3)	EB	100	6	1	94.0^b	7

SBA-15负载的N-杂环卡宾-吡啶钼配合物在二氧化碳转化制备环状碳酸酯中的应用