Mechanistic insights into the hydrogenation of dimethyl oxalate to methyl glycolate over Ni-Ag/SiO2 catalyst

doi:10.11949/0438-1157.20250364

Abstract

Abstract:

Herein, a series of Ni-Ag/SiO₂ bimetallic catalysts with varying metal loadings were fabricated to investigate the synergistic mechanism of active sites in the selective hydrogenation of dimethyl oxalate (DMO) to methyl glycolate (MG). The morphology and active site structures of the catalysts were analyzed in detail by nitrogen physical adsorption, hydrogen temperature-programmed reduction, X-ray diffraction, and X-ray photoelectron spectroscopy. The results revealed that the Ni species in the prepared Ni-Ag/SiO₂ bimetallic catalyst mainly existed in the layered nickel phyllosilicate structure, and Ag particles were supported on its surface. Catalytic performance tests, combined with in situ Fourier-transform infrared spectroscopy and temperature-programmed desorption experiments, found that bimetallic catalysts with different Ni/Ag ratios exhibited significant differences in the adsorption and activation behavior of DMO and H₂. Specifically, increasing Ni content promotes the activation of DMO, while increasing Ag content is beneficial for H₂ activation, indicating that Ni⁰/Ni ^δ⁺interface sites and Ag species of Ni-Ag/SiO₂ bimetallic catalysts are responsible for the activations of DMO and H₂, respectively. By optimizing the Ni/Ag (mass ratio) to 5∶1, the catalyst achieved a remarkable DMO conversion of 99.6% and MG selectivity of 91.5% under mild reaction conditions, with no significant performance degradation observed over 350 h of stability test. This work provides critical insights into the design of efficient catalysts for the conversion of coal-based syngas to MG, and also highlights a rational strategy for balancing substrate activation and hydrogen in heterogeneous catalysis.

Key words: dimethyl oxalate, hydrogenation, bimetallic, methyl glycolate

摘要：

制备了系列不同金属负载量的Ni-Ag/SiO₂双金属催化剂，揭示了草酸二甲酯（DMO）选择性加氢制乙醇酸甲酯（MG）的活性位点协同机制。采用氮气物理吸附、氢气程序升温还原、X射线衍射、X射线光电子能谱等表征技术对催化剂的形貌和活性位点结构进行了详细分析。结果表明，制得的Ni-Ag/SiO₂双金属催化剂中Ni物种主要以层状硅酸镍结构存在，且Ag颗粒负载在其表面。结合催化性能测试与原位红外光谱、程序升温脱附等表征实验探究了催化剂的构-效关系，发现不同Ni/Ag的双金属催化剂表现出显著差异的DMO和H₂的吸附活化行为。其中，Ni含量增加促进了DMO吸附活化，而Ag含量增加有利于H₂吸附活化，表明Ni-Ag/SiO₂双金属催化剂中Ni⁰/Ni ^δ⁺界面位点和Ag位点可能分别与DMO和H₂吸附活化相关。当调控Ni/Ag（质量比）至5∶1，可有效平衡DMO与H₂吸附活化，其中5Ni-1Ag/SiO₂双金属催化剂上DMO转化率和MG选择性分别达到了99.6% 和91.5%，且连续运行350 h无明显衰减。研究结果可为煤基合成气制MG的高效催化剂设计提供借鉴。

关键词: 草酸二甲酯, 加氢, 双金属, 乙醇酸甲酯

CLC Number:

TQ 032.4

Yun SHEN, Dai ZHANG, Xiaofeng XU, Yueqiang CAO, Jinghong ZHOU, Wei LI, Xinggui ZHOU. Mechanistic insights into the hydrogenation of dimethyl oxalate to methyl glycolate over Ni-Ag/SiO₂ catalyst[J]. CIESC Journal, 2025, 76(10): 5101-5113.

沈赟, 张岱, 徐晓峰, 曹约强, 周静红, 李伟, 周兴贵. Ni-Ag/SiO₂催化草酸二甲酯加氢制乙醇酸甲酯反应机理研究[J]. 化工学报, 2025, 76(10): 5101-5113.

Figures/Tables 13

Table 1 Physicochemical properties of Ni-Ag/SiO2 catalysts

样品	负载量^①/%		S_BET^② / (m²/g)	V_pore^③/ (cm³/g)	D_BJH^③/ nm	Q_CO^④/ (mmol/g)	$Q H 2$ ^⑤/ (mmol/g)	$Q ∆ H 2$ ^⑥/ (mmol/g)
样品	Ni	Ag	S_BET^② / (m²/g)	V_pore^③/ (cm³/g)	D_BJH^③/ nm	Q_CO^④/ (mmol/g)	$Q H 2$ ^⑤/ (mmol/g)	$Q ∆ H 2$ ^⑥/ (mmol/g)
SiO₂	—	—	212	0.30	4.4	—	—	—
5Ni-1Ag	4.6	0.98	247	0.61	8.24	0.0027	0.1241	0.1214
10Ni-1Ag	9.8	0.98	267	0.58	7.00	0.0064	0.1289	0.1225
15Ni-1Ag	14.7	0.97	285	0.54	5.90	0.0102	0.1344	0.1242
10Ni-1.5Ag	9.8	1.5	261	0.58	6.88	0.0104	0.1913	0.1809
10Ni-2Ag	9.8	2	257	0.57	6.81	0.0121	0.2975	0.2854

Table 1 Physicochemical properties of Ni-Ag/SiO2 catalysts

样品	负载量^①/%		S_BET^② / (m²/g)	V_pore^③/ (cm³/g)	D_BJH^③/ nm	Q_CO^④/ (mmol/g)	$Q H 2$ ^⑤/ (mmol/g)	$Q ∆ H 2$ ^⑥/ (mmol/g)
样品	Ni	Ag	S_BET^② / (m²/g)	V_pore^③/ (cm³/g)	D_BJH^③/ nm	Q_CO^④/ (mmol/g)	$Q H 2$ ^⑤/ (mmol/g)	$Q ∆ H 2$ ^⑥/ (mmol/g)
SiO₂	—	—	212	0.30	4.4	—	—	—
5Ni-1Ag	4.6	0.98	247	0.61	8.24	0.0027	0.1241	0.1214
10Ni-1Ag	9.8	0.98	267	0.58	7.00	0.0064	0.1289	0.1225
15Ni-1Ag	14.7	0.97	285	0.54	5.90	0.0102	0.1344	0.1242
10Ni-1.5Ag	9.8	1.5	261	0.58	6.88	0.0104	0.1913	0.1809
10Ni-2Ag	9.8	2	257	0.57	6.81	0.0121	0.2975	0.2854

Fig.1 (a) N2 adsorption-desorption isotherms and (b) BJH pore size distributions of Ni-Ag/SiO2 catalysts

Fig.2 (a) H2-TPR patterns, (b) XRD patterns and [(c), (d)] XRD local amplified patterns of Ni-Ag/SiO2 catalysts

Table 2 Amount of hydrogen consumption corresponding to the H2-TPR peaks of Ni-Ag/SiO2 catalysts

样品	低温区还原峰耗氢量/(10^-3 mmol/g)	中温区还原峰耗氢量/(10^-2 mmol/g)	高温区还原峰耗氢量/(mmol/g)
5Ni-1Ag	4.380	3.375	0.465
10Ni-1Ag	4.311	4.915	0.831
15Ni-1Ag	4.368	8.149	1.166
10Ni-1.5Ag	5.948	5.893	0.818
10Ni-2Ag	6.534	5.825	0.815

Fig.3 TEM images of Ni-Ag/SiO2 catalysts with different Ni and Ag loadings

Fig.4 [(a),(b)] Ag XPS spectra and [(c),(d)] Ni 2p3/2 XPS spectra of Ni-Ag/SiO2 catalysts

Fig.5 Performance of Ni-Ag/SiO2 catalysts with (a)—(c) different Ni loadings and (d)—(f) different Ag loadings as a function of LHSV (reaction conditions: 220℃, 2.0 MPa, H2/DMO = 50)

Fig.6 Performance of Ni-Ag/SiO2 catalysts with (a)—(c) different Ni loadings and (d)—(f) different Ag loadings as a function of H2/DMO (reaction conditions: 220℃, 2.0 MPa, LHSV = 1 h-1)

Table 3 Performance evaluation results of Ni-Ag/SiO2 catalysts with different Ni and Ag loadings

催化剂	LHSV/h^-1	H/D	DMO 转化率/%	选择性/%			MG 收率%
催化剂	LHSV/h^-1	H/D	DMO 转化率/%	MG	EG	其他	MG 收率%
10Ni/SiO₂	0.5	50	12.6	83.1	0.5	16.4	10.5
10Ni/SiO₂	1	50	10.4	93.3	0.1	6.6	9.7
10Ni-0.5Ag/SiO₂	0.5	50	87.7	96.7	1.6	1.7	84.8
	0.75	50	70.6	97.5	0.8	1.7	68.9
	1	50	58.0	97.5	0.6	1.9	56.5
	1.25	50	47.9	97.4	0.5	2.1	46.6
	1.5	50	39.9	97.3	0.4	2.3	38.8
	1	100	73.5	97.9	0.9	1.3	71.9
	1	75	64.5	97.9	0.7	1.4	63.2
	1	50	55.0	97.5	0.7	1.9	53.6
	1	25	40.2	96.6	0.5	3.0	38.8

Fig.7 In-situ FTIR patterns of DMO adsorbed on Ni-Ag/SiO2 catalysts with different Ni and Ag loadings

Fig.8 (a) H2-TPD patterns and (b) DMO-TPD patterns of Ni-Ag/SiO2 catalysts with different Ni and Ag loadings

Table 4 TPD area of Ni-Ag/SiO2 catalysts with different Ni and Ag loadings

催化剂	H₂-TPD	DMO-TPD	A(H₂)/A(DMO)
5Ni-1Ag/SiO₂	0.70	0.35	1.98
10Ni-1Ag/SiO₂	0.88	0.67	1.31
15Ni-1Ag/SiO₂	0.95	0.78	1.23
10Ni-1.5Ag/SiO₂	1.07	0.68	1.59
10Ni-2Ag/SiO₂	1.27	0.69	1.85

Fig.9 5Ni-1Ag/SiO2 catalyst stability assessment results (reaction conditions: T=220℃, P=2.0 MPa, LHSV= 0.75 h-1, H2/DMO=50)

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Mechanistic insights into the hydrogenation of dimethyl oxalate to methyl glycolate over Ni-Ag/SiO₂ catalyst

Ni-Ag/SiO₂催化草酸二甲酯加氢制乙醇酸甲酯反应机理研究

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