Producing of cinnamyl alcohol from cinnamaldehyde over supported gold nanocatalyst

doi:10.1016/S1872-2067(20)63678-6

Abstract

Abstract:

Chemoselective hydrogenation of unsaturated aldehyde to unsaturated alcohol has attracted growing interests in recent years due to its widespread applications in fine chemicals. However,the hydrogenation of the C=O bond was thermodynamically and kinetically unfavorable over the hydrogenation of the C=C bond. Thus,to obtain the unsaturated alcohol from the unsaturated aldehyde is very difficult in most of the catalytic systems. In this work,ZnAl-hydrotalcite-supported cysteine-capped Au25 nanoclusters were used as the precatalysts for chemoselective hydrogenation of cinnamaldehyde to cinnamyl alcohol. The catalyst showed stable high selectivity (~ 95%) at prolonged reaction time and complete conversion of the substrate. According to the results of the control experiments,the in-situ DRIFTS of the substrate under high pressure of hydrogen and the 27Al MAS-NMR spectroscopy,we proposed that the difference of the preferential adsorption of the C=O bond to that of the C=C bond was derived from the nature of the support of the gold catalysts.

Key words: Gold nanocluster, Support effect, Cinnamyl alcohol, Selective hydrogenation, Cinnamaldehyde

Yuan Tan, Xiaoyan Liu, Leilei Zhang, Fei Liu, Aiqin Wang, Tao Zhang. Producing of cinnamyl alcohol from cinnamaldehyde over supported gold nanocatalyst[J]. Chinese Journal of Catalysis, 2021, 42(3): 470-481.

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https://www.cjcatal.com/EN/Y2021/V42/I3/470

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Entry	Catalyst	Size (nm)	Conv. (%)		Sel. (%)
Entry	Catalyst	Size (nm)	Conv. (%)		COL	HCAL		HCOL
1	1.1%Au₂₅/ZnAl-300	1.7 ^b	98.3	95.4			0	4.5
2	1.0%Au₂₅/MgAl-300	2.2 ^b	99.2		39.5	13.6		38.4
3	1.0%Au₂₅/NiAl-300	3.2 ^b	100		0	0		86.7
4	1.0%Au/ZnAl-300(DP) ^a	2.6 ^b	61.5		85.9	3.7		3.6
5	1.0%Au/ZrO₂^c	3.3	75.7		50.0	17.3		16.8
6	0.8%Au/Fe₂O₃^c	1.8	93.0		45.4	4.9		3.6
7	1.5%Au/TiO₂^d	4.1	51.9		14.6	0		0
8	1.1%Au₂₅/ZnAl-HT	1.4	26.8		43.6	1.6		0
9	ZnAl-300	—	9.6		23.9	3.1		0
10	1.1%Au₂₅/ZnAl-300^e	1.7	28.4		35.2	0		0

Entry	Catalyst	Size (nm)	Conv. (%)		Sel. (%)
Entry	Catalyst	Size (nm)	Conv. (%)		COL	HCAL		HCOL
1	1.1%Au₂₅/ZnAl-300	1.7 ^b	98.3	95.4			0	4.5
2	1.0%Au₂₅/MgAl-300	2.2 ^b	99.2		39.5	13.6		38.4
3	1.0%Au₂₅/NiAl-300	3.2 ^b	100		0	0		86.7
4	1.0%Au/ZnAl-300(DP) ^a	2.6 ^b	61.5		85.9	3.7		3.6
5	1.0%Au/ZrO₂^c	3.3	75.7		50.0	17.3		16.8
6	0.8%Au/Fe₂O₃^c	1.8	93.0		45.4	4.9		3.6
7	1.5%Au/TiO₂^d	4.1	51.9		14.6	0		0
8	1.1%Au₂₅/ZnAl-HT	1.4	26.8		43.6	1.6		0
9	ZnAl-300	—	9.6		23.9	3.1		0
10	1.1%Au₂₅/ZnAl-300^e	1.7	28.4		35.2	0		0

Catalyst	Reaction conditions					Conv. (%)	Sel. (%)	Ref.
Catalyst	Solvent	Au (mol%)	Tem. (°C)	P_H2 (MPa)	t (h)	Conv. (%)	Sel. (%)	Ref.
Au₂₅/ZnAl-300	isopropanol	1.0	130	1.5	5 15	98.3 100	95.4 95.7	This work
Au/ZnO-CP	isopropanol	1.0	110	2	0.8	100	~92	[19]
Au/MgAlO	ethanol	2.4	120	1	5	96	40	[30]
Au/meso-CeO₂	H₂O/ethanol	1.0	100	1	0.5	48	97	[31]
Au₂₅/Fe₂O₃ Au₂₅/TiO₂	toluene/ethanol	5.1	0	0.1	3	49 46	100 100	[32]
Au/DMF	amide	1.0	60	4	56	94	94	[33]
Au/Mg₂AlO	ethanol	0.2	120	1	2	78	85	[34]
Au/5FeAl Au/HDAE	isopropanol	0.7 0.6	100	1	3	20 28	67 88	[35]
Au/TiO₂	ethanol	6.3	60	0.1	—	50	47	[36]
Au/FeOOH	ethanol	14.8	60	0.1	—	50	91	[37]
Au/Al₂O₃	ethanol	0.1	100	8.5	2.8	94	89	[38]

Catalyst	Reaction conditions					Conv. (%)	Sel. (%)	Ref.
Catalyst	Solvent	Au (mol%)	Tem. (°C)	P_H2 (MPa)	t (h)	Conv. (%)	Sel. (%)	Ref.
Au₂₅/ZnAl-300	isopropanol	1.0	130	1.5	5 15	98.3 100	95.4 95.7	This work
Au/ZnO-CP	isopropanol	1.0	110	2	0.8	100	~92	[19]
Au/MgAlO	ethanol	2.4	120	1	5	96	40	[30]
Au/meso-CeO₂	H₂O/ethanol	1.0	100	1	0.5	48	97	[31]
Au₂₅/Fe₂O₃ Au₂₅/TiO₂	toluene/ethanol	5.1	0	0.1	3	49 46	100 100	[32]
Au/DMF	amide	1.0	60	4	56	94	94	[33]
Au/Mg₂AlO	ethanol	0.2	120	1	2	78	85	[34]
Au/5FeAl Au/HDAE	isopropanol	0.7 0.6	100	1	3	20 28	67 88	[35]
Au/TiO₂	ethanol	6.3	60	0.1	—	50	47	[36]
Au/FeOOH	ethanol	14.8	60	0.1	—	50	91	[37]
Au/Al₂O₃	ethanol	0.1	100	8.5	2.8	94	89	[38]

Catalyst	Size (nm)	Conv. (%)
Catalyst	Size (nm)	Styrene ^a	Styrene ^b		Benzaldehyde ^b
1.1% Au₂₅/ZnAl-300	1.7	3.8	5.1		77.7
1.0% Au₂₅/MgAl-300	2.2	67.5	58.2	95.1
1.0% Au/ZrO₂	3.1	71.4	97.2		100