木质素基芳香醛类化合物的制备及其转化研究进展

doi:10.3969/j.issn.0253-2417.2023.04.016

Abstract

Abstract:

Aromatic aldehydes were important raw materials for the synthesis of fine chemicals such as dyes, spices, pesticides and drugs. Lignin was the second largest component in lignocellulosic biomass, and was the only renewable resource for producing aromatic compounds. Catalytic oxidation could transform lignin into highly functionalized aromatic aldehydes(e.g., p-hydroxybenzaldehyde, vanillin, syringaldehyde, etc.) under mild conditions, which was regarded as one of the effective ways to realize the resource utilization of lignin. Firstly, the structural characteristics and depolymerization mechanism of lignin were introduced, and the effects of lignin structure on the production of aromatic aldehydes were summarized and discussed. Then, recent progress in the preparation of aromatic aldehydes by oxidative depolymerization of lignin was introduced in detail from the methods of catalytic oxidative depolymerization methods(e.g., wet oxidation and alkaline nitrobenzene oxidation, catalytic oxidative depolymerization with homogeneous and heterogeneous catalysts, photocatalytic oxidation and electrocatalytic oxidation) and types of catalysts(e.g., metal salts and metal porphyrins, heteropoly acids and other homogeneous catalysts, metal oxides and perovskite oxides and other heterogeneous catalysts). Moreover, the upgrading and conversion of aromatic aldehydes into high value-added products such as 2-methoxy-4-methylphenol, aromatic nitrile, aromatic amides and new organic polymer materials were further summarized. Finally, the existing problems in the current research on lignin oxidative depolymerization were summarized, and the possible development direction in the future was proposed, which laid a foundation for lignin oxidative depolymerization and high value-added utilization.

Key words: lignin, catalytic oxidation, aromatic aldehydes, synthesis, conversion

CLC Number:

TQ35

Geliang XIE, Xianjun ZHOU, Chengyu DONG, Wei CHEN, Lujiang XU, Zhen FANG. Progress in the Preparation and Transformation of Lignin-based Aromatic Aldehydes[J]. Chemistry and Industry of Forest Products, 2023, 43(4): 115-126.

Figures/Tables 6

Fig.1

Table 1

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Fig.2

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催化剂 catalyzer	原料 raw material	溶剂 solvent	转化率/% conversion	芳香醛产率¹⁾/% aromatic aldehyde yield			文献 ref.
催化剂 catalyzer	原料 raw material	溶剂 solvent	转化率/% conversion	PHA	VA	SA	文献 ref.
CuSO₄	桉木木质素磺酸盐eucalyptus lignosulfonate	NaOH	—	—	4.5	16.1	[12]
CuSO₄	松木木质素pine lignin	NaOH	100	5.0	12.5	6.9	[15]
CuSO₄	有机溶剂木质素organic solvent lignin	Na₂HPO₄+Na₃PO₄	100	4.7	13.6	7.5	[16]
CuSO₄	碱木质素alkali lignin	Na₂HPO₄+Na₃PO₄	100	5.0	14.2	7.4	[16]
CuSO₄+FeCl₃	杨木水解木质素poplar hydrolyzed lignin	NaOH	71.5	—	4.6	9.8	[17]
Co(TPPS₄)	玉米秸秆酶解木质素enzymatic hydrolysis of lignin from corn straw	NaOH-H₂O₂	75.1	5.5	4.7	2.7	[18]
CPTPPS₃Co		NaOH-H₂O₂	—	5.7	4.4	2.6	[19]

催化剂 catalyzer	原料 raw material	溶剂 solvent	反应条件 reaction conditions	产物(产率)¹⁾ product yield	文献 ref.
H₃PMo₁₂O₄₀	硫酸盐木质素Kraft lignin	CH₃OH/C₂H₅OH-H₂O	170 ℃, 20 min	VA(5.18%)+MV	[22]
H₃PMo₁₂O₄₀	棉秆木质素cotton stalk lignin	γ-戊内酯γ-pentalactone	150 ℃, 4 h	转化率92.6% conversion 92.6%	[23]
H₅PV₂Mo₁₀O₄₀	麦草碱木质素wheat straw alkali lignin	[BMIM]Cl	140 ℃, 4 h	VA(6.97%)	[23]
H₅PV₂Mo₁₀O₄₀	酶解木质素enzymatic lignin	[BMIM]Cl	120 ℃, 3 h	VA(10.32%)	[24]

催化剂 catalyst	原料 substrate	芳香醛产率¹⁾/% aromatic aldehyde yield			文献 ref.
催化剂 catalyst	原料 substrate	PHA	VA	SA	文献 ref.
CuO	造纸黑液木质素lignin obtained from black liquor	—	1.16	2.55	[26]
Cu₂O		—	2.44	3.12	[26]
CuO-Cu₂O		—	10.24 ^a
Cu/γ-Al₂O₃	麦秸、甘蔗渣木质素wheat straw, bagasse lignin	—	~11.3	~4.8	[27]
Co₅₀-Fe₅₀	小麦有机溶剂木质素wheat organic solvent lignin	0.2	3.33	9.74	[28]
LaFeO₃	玉米秸秆酶解木质素enzymatic corn straw lignin	1.89	4.10	8.77	[29]
LaMnO₃		2.03	4.32	9.33	[30]
LaCoO₃		2.23	4.55	9.99	[31]
LaCo_0.8Cu_0.2O₃		2.88	5.30	12.8	[34]
LaMn_0.8Cu_0.2O₃		2.90	5.07	14.6	[35]
LaFe_0.8Cu_0.2O₃		2.49	4.56	11.51	[36]

催化剂 catalyst	溶剂 solvent	反应条件 reaction conditions	转化率 conversion rate	MMP选择性/% selectivity of MMP	文献 ref.
Pd/CM170	水/十氢萘H₂O/decalin	100 ℃, 14 500 kPa H₂, 1 h	>99	52.0	[48]
Pd/C	蒸馏水distilled H₂O	3 000 kPa H₂, 30 min	100	95	[50]
Pd_SA+C/SAPO-31	C₂H₅OH+HCOOH	80 ℃, 30 min	99	99	[51]
Mo₂C/AC	去离子水deionized H₂O	150 ℃, 1 MPa H₂, 6 h	33.8	12.9	[52]
Co@NC@C	去离子水deionized H₂O	140 ℃, 0.5 h, 101.3 kPa H₂	100.0	47.4	[53]
Ni₃Co@NC@C	去离子水deionized H₂O	140 ℃, 0.5 h, 101.3 kPa H₂	97.0	41.6	[53]
Cu/Zn₁₅Al₄Sn-LDH	2-丙醇2-propanol	180 ℃, 4 h, N₂	100.0	98.5	[54]
Co/N-C-600	2-丙醇2-propanol	180 ℃, 1 MPa H₂, 4 h	95	96	[55]
Co/N-C-700	2-丙醇2-propanol	180 ℃, 1 MPa N₂, 4 h	98	85	[56]
Pd/Ru@GO	CH₃OH	30 ℃, 1 000 kPa H₂, 12 h	100.0	96	[58]
ClMPA@Pd/Al₂O₃	C₂H₅OH	40 ℃, 1 378 kPa H₂	>99	87	[59]
Pd₁/WO_2.72	C₂H₅OH	40 ℃, 101.3 kPa H₂	>99	>99	[60]

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Progress in the Preparation and Transformation of Lignin-based Aromatic Aldehydes

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