Hierarchical manganese-containing TS-1 zeolite for the direct oxidation of cyclohexane to adipic acid with molecular oxygen: Synergy between matrix Ti and Mn species

doi:10.1016/S1872-2067(25)64822-4

Abstract

Abstract:

The direct oxidation of cyclohexane to adipic acid (AA) without the use of HNO₃ is important but still challenging. Herein, hierarchical manganese-containing TS-1 zeolite (HMTS) was prepared using an improved direct synthesis method, in which titanium and manganese coexist within the zeolite matrix, as characterized by X-ray diffraction, X-ray photoelectron spectroscopy, transmission electron microscopy, ultraviolet, extended X-ray absorption fine structure etc. The introduction of matrix Mn species (Mn³⁺, Mn⁴⁺) not only increased the surface oxygen vacancies, but also generated medium-strong acid sites, which endowed HMTS catalysts with the ability to efficiently activate oxygen and facilitate substrate coordination. On HMTS-3, one-pot oxidation of cyclohexane at 140 °C and 2 MPa O₂ gave 81.6% conversion and 71.5% AA selectivity, the highest value obtained at present. Control experiments with single-component samples confirmed that matrix Ti⁴⁺ catalyzed the conversion of cyclohexane to a mixture of cyclohexanone and cyclohexanol (KA oil), and matrix Mn favored the conversion of KA oil to AA. The synergy between matrix Ti and Mn inside the hierarchical structure were the key factor for the superior activity. Specifically, the matrix Ti⁴⁺ might activate oxygen to form Ti-O₂^2- which facilitated the activation of the C-H bond of cyclohexane. The activation of O₂ on matrix Mn³⁺ formed Mn⁴⁺-O₂^- favoring the breaking of the C-C bond of cyclohexanone. The hierarchical structure not only exposed more active sites and promoted mass transfer, but also provided a better microenvironment for the matrix Mn to synergize with the matrix Ti, which facilitated the overall reaction. This work demonstrated the practical application potential of HMTS and provided useful insights into the direct oxidation of cyclohexane to AA.

Key words: Cyclohexane oxidation, Matrix Mn species, Hierarchical TS-1 zeolite, Synergic effect, O₂oxidation, Adipic acid

Mingdong Zhang, Xueshuang Wu, Guiying Li, Changwei Hu. Hierarchical manganese-containing TS-1 zeolite for the direct oxidation of cyclohexane to adipic acid with molecular oxygen: Synergy between matrix Ti and Mn species[J]. Chinese Journal of Catalysis, 2025, 79: 127-147.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(25)64822-4

https://www.cjcatal.com/EN/Y2025/V79/I12/127

Figures/Tables 19

Scheme 1. Comparison of current industrial process (A) and green approach to produce AA described in this work (B).

Scheme 2. Synthesis process of HMTS by an improved one-step hydrothermal method.

Fig. 1. (a) Survey spectra of TS-1, MTS-1, HTS-1, HMS-3, and HMTS-3. XPS spectra of Ti 2p (b), Mn 2p (c) and O 1s (d) of samples.

Table 1 Surface chemical composition determined by XPS (mol%).

Sample	O	Si	Ti	Mn	Ti^b (wt%)	Mn^b (wt%)
TS-1	56.71	43.28	0.01^a	—	0.02	—
MTS-1	62.70	34.42	0.67	2.21	1.51	5.73
HTS-1	61.61	38.20	0.19	—	0.44	—
HMTS-1	62.18	37.21	0.21	0.40	0.48	1.06
HMTS-2	62.63	36.44	0.16	0.77	0.39	2.04
HMTS-3	64.02	34.54	0.16	1.28	0.38	3.40
HMTS-4	66.85	31.11	0.16	1.88	0.37	5.04
HMS-3	63.86	34.62	—	1.12	—	2.62
HMTS-3^c	62.68	35.61	0.41	1.30	0.94	3.41
HMTS-3^d	62.55	35.82	0.45	1.18	1.01	3.10
HMS-3^c	63.58	35.23	—	1.19	—	3.15
HMS-3^d	63.40	35.34	—	1.26	—	3.33

Table 2 The Ti and Mn contents in different chemical states on the surface.

Sample	Framework Ti species (%)	Extra-framework Ti species (%)	Mn²⁺ (%)	Mn³⁺ (%)	Mn⁴⁺ (%)
TS-1	100.0	—	—	—	—
MTS-1	41.6	58.4	51.3	37.8	10.9
HTS-1	100.0	—	—	—	—
HMTS-1	100.0	—	39.7	34.8	25.5
HMTS-2	100.0	—	35.2	44.6	20.2
HMTS-3	100.0	—	24.5	54.2	21.3
HMTS-4	61.4	38.6	34.4	42.8	22.8
HMS-3	—	—	21.6	56.1	22.3

Fig. 2. (a) N2 adsorption-desorption isotherms of all samples. (b) Pore diameter distribution of all catalyst samples.

Table 3 Physicochemical properties of different catalysts.

Sample	S_BET^a (m² g^-1)	S_mic (m² g^-1)	S_ext (m² g^-1)	Vp^total (cm³ g^-1)	V_mic (cm³ g^-1)
TS-1	415.59	284.16	131.43	0.21	0.12
MTS-1	384.65	258.58	126.08	0.20	0.11
HTS-1	517.82	255.80	262.02	0.34	0.12
HMTS-1	511.15	245.74	265.41	0.35	0.11
HMTS-2	501.15	237.86	263.29	0.35	0.12
HMTS-3	478.65	234.20	244.45	0.33	0.11
HMTS-4	421.97	230.46	191.51	0.29	0.10
HMS-3	483.51	239.73	243.78	0.33	0.12

Fig. 3. (a) XRD patterns of catalyst samples. (b) Enlarged scale between 2θ = 7.4° and 9.7° of (a) for HMS-3, HTS-1, HMTS-1, HMTS-2, HMTS-3, and HMTS-4.

Fig. 4. TEM of catalyst samples prepared using different methods. (a-c) TS-1; (d-f) MTS-1; (g-i) HTS-1; (j-l) HMTS-3. (m) The corresponding EDS mapping of Fig. 4(e). (n) The corresponding EDS mapping of Fig. 4(k).

Fig. 5. (a) UV-vis spectra of TS-1, MTS-1, HTS-1, HMTS-3 and HMS-3 (no significant offset). (b) UV-vis spectra of HMTS-1, HMTS-2, HMTS-3, HMTS-4 and HMS-3 (no significant offset). (c) FT-IR spectra of TS-1, MTS-1, HTS-1 and HMTS-3. (d) FT-IR spectra of HMTS-1, HMTS-2, HMTS-3, HMTS-4 and HMS-3.

Fig. 6. (a) Mn K-edge XANES spectra of HMTS-3, HMS-3 and different reference samples. (b) Ti K-edge XANES spectra of HMTS-3, HTS-1 and different reference samples. (c) Fourier transform k3-weighted Mn EXAFS spectra in the R-spacing of different samples. (d) Fourier transform k3-weighted Ti EXAFS spectra in the R-spacing of different samples.

Fig. 7. WT-EXFAS spectra of Mn species. (a) Mn foil; (b) MnO2; (c) Mn3O4; (d) HMTS-3; (e) HMS-3. WT-EXFAS spectra of Ti species. (f) Ti foil; (g) TiO2; (h) HMTS-3; (i) HTS-1.

Table 4 Catalytic performance of different catalystsa.

Entry	Catalyst	Conv. (%)	Selectivity (%)
Entry	Catalyst	Conv. (%)	A	B	KA oil^b	C	D
1	Blank	trace	—	—	—	—	—
2	TS-1	18.2	40.2	25.7	65.9	20.5	13.6
3	MTS-1	26.4	34.7	20.8	55.5	30.5	14.0
4	HTS-1	43.4	30.2	18.3	48.5	41.1	10.4
5	HMS-3	35.1	27.2	16.5	43.7	46.3	10.0
6	HMTS-1	58.3	22.1	13.4	35.5	54.7	9.8
7	HMTS-2	74.4	19.0	7.3	26.3	62.2	11.5
8	HMTS-3	81.6	11.5	3.6	15.1	71.5	13.4
9	HMTS-4	79.1	11.9	2.6	14.5	68.3	17.2
10^c	HMS-3 & HTS-1	61.2	17.3	10.6	27.9	65.7	10.4
11^d	HMTS-3	—	—	—	—	—	—
12^e	HMTS-3	—	—	—	—	—	—

Fig. 8. Effect of temperature (0.05 g of catalyst, 2.34 g substrate, 27 mL acetonitrile, 2.0 MPa O2, 6 h) (a), reaction pressure (0.05 g of catalyst, 2.34 g substrate, 27 mL acetonitrile, 140 °C, 6 h) (b), catalyst amount (2.34 g substrate, 27 mL acetonitrile, 2.0 MPa O2, 140 °C, 6 h) (c) and reaction time (0.05 g of catalyst, 2.34 g substrate, 27 mL acetonitrile, 2.0 MPa O2, 140 °C) (d) on the conversion of cyclohexane and AA vs. KA oil selectivity over HMTS-3 catalysts (“others” were mainly glutaric acid and succinic acid).

Fig. 9. (a) Reaction results of HTS-1, HMS-3 and HMTS-3 with different substrates. (b) O2-TPD patterns of all catalysts (significant offset can be observed at 100?140 °C). (c) EPR spectra for oxygen vacancy. (d). NH3-TPD patterns of all catalysts. (e) Py-IR patterns of all catalysts. (f) Enlarged scale between wavenumbers = 1510 and 1560 cm?1 of Fig. 9(e).

Table 5 Acidity properties of different samples.

Sample	Total acidity^a (mmol g^-1)	B/L ratio ^b	C_BAS^c (mmol g^-1)	C_BAS^d (mmol g^-1)
TS-1	0.27	0.06	0.015	0.018
MTS-1	0.25	0.04	0.009	0.008
HTS-1	0.25	0.04	0.009	0.011
HMTS-1	0.28	0.05	0.013	0.014
HMTS-2	0.35	0.05	0.017	0.016
HMTS-3	0.42	0.04	0.017	0.019
HMTS-4	0.31	0.04	0.012	0.013
HMS-3	0.35	0.04	0.014	0.016

Fig. 10. In-situ DRIFTS experiments of oxygen adsorption on TS-1 (a), MTS-1 (b), HTS-1 (c), HMS-3 (d), and HMTS-3 (e).

Fig. 11. Mechanistic pathway for oxidative conversion of cyclohexane to AA, (2), (3), (4), (6), (7), (8) represent the possible catalytically active species shown in Scheme 1.

Fig. 12. (a) Recyclability tests of HMTS-3 catalyst for cyclohexane oxidation. XRD patterns (b), and Ti 2p (c) and C 1s (d) XPS spectra of recycled catalysts, of recycled catalysts.

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