丰产金属催化的聚烯烃氧化降解研究进展

doi:10.6023/cjoc202603020

有机化学 ›› 2026, Vol. 46 ›› Issue (7): 2544-2562.DOI: 10.6023/cjoc202603020 上一篇下一篇

综述与进展

丰产金属催化的聚烯烃氧化降解研究进展

严睿杰^a, 俞亦涵^a, 石宏伟^a^,^*(), 焦宁^a^,^b^,^c

^a 北京大学药学院新基石科学实验室北京 100191
^b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
^c 香港创新科技署Health@InnoHK 合成化学与化学生物学实验室有限公司香港 999077

收稿日期:2026-03-15 修回日期:2026-05-17 发布日期:2026-06-03
基金资助:
国家自然科学基金(22401010); 国家自然科学基金(22293014); 国家自然科学基金(22131002); 国家自然科学基金(22161142019); 国家重点研发计划(2021YFA1501700)

Recent Advances in Earth-Abundant Metal-Catalyzed Oxidative Degradation of Polyolefins

Ruijie Yan^a, Yihan Yu^a, Hongwei Shi^a^,^*(), Ning Jiao^a^,^b^,^c

^a State Key Laboratory of Natural and Biomimetic Drugs, New Cornerstone Science Laboratory, Chemical Biology Center, School of Pharmaceutical Sciences, Peking University, Beijing 100191
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
^c Laboratory for Synthetic Chemistry and Chemical Biology Limited, Health@InnoHK, Innovation and Technology Commission, Hong Kong 999077

Received:2026-03-15 Revised:2026-05-17 Published:2026-06-03
Contact: *E-mail: hwshi@bjmu.edu.cn
Supported by:
National Natural Science Foundation of China(22401010); National Natural Science Foundation of China(22293014); National Natural Science Foundation of China(22131002); National Natural Science Foundation of China(22161142019); National Key R&D Program of China(2021YFA1501700)

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摘要/Abstract

聚烯烃的催化氧化降解是实现塑料资源循环利用的重要途径之一. 近年来, 地球丰度金属催化剂在该领域展现出显著优势, 能够实现聚烯烃的高效、高选择性氧化转化, 为发展绿色、经济、可规模化的塑料化学回收新工艺提供了可能. 本综述系统总结了基于地球丰度金属的聚烯烃催化氧化降解研究进展, 并着重探讨了其在实际塑料废弃物转化中的应用案例. 最后, 对当前该领域面临的挑战及未来发展方向进行了展望.

关键词: 丰产金属催化, 聚烯烃, 塑料降解, 氧化反应, 碳碳键活化

Catalytic oxidative degradation of polyolefins represents one of the important pathways for achieving resource recycling of plastics. In recent years, earth-abundant metal catalysts have demonstrated significant advantages in this field, enabling efficient and highly selective oxidative transformation of polyolefins. This offers promising potential for developing green, economical, and scalable novel chemical recycling processes for plastics. This review systematically summarizes recent advances in the catalytic oxidative degradation of polyolefins using earth-abundant metals, with a focus on their application examples in the conversion of actual plastic waste. Furthermore, the current challenges and future research directions in this field are outlined and discussed.

Key words: earth-abundant metal catalysis, polyolefins, plastic degradation, oxidation reaction, carbon-carbon bond activation

引用此文

严睿杰, 俞亦涵, 石宏伟, 焦宁. 丰产金属催化的聚烯烃氧化降解研究进展[J]. 有机化学, 2026, 46(7): 2544-2562.

Ruijie Yan, Yihan Yu, Hongwei Shi, Ning Jiao. Recent Advances in Earth-Abundant Metal-Catalyzed Oxidative Degradation of Polyolefins[J]. Chinese Journal of Organic Chemistry, 2026, 46(7): 2544-2562.

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图/表 28

Scheme 1. Earth-abundant metal-catalyzed oxidative degradation of polyolefins (a) Transformation of polyolefin waste into functionalized oxygenates and nitrogenates; (b) Overview of proposed key reaction mechanisms for earth-abundant metal catalysis processes; (c) Summary of earth-abundant metal catalysts used in polyolefin oxidative degradation.

Catalyst	Conditions	Plastic	Product (Yield/%)	Ref.
PSA-1-TiO	O₂ (0.1 MPa), 370 nm, r.t., 4 h	PS	BA (18~40)	[33]
TS-1	Air (1.5 MPa), H₂O, 140~200 ℃, 12 h	PP/PE	Oil-DA (59~85)	[39]
VO(acac)₂/MBTB	PEG-400, 400~440 nm, NaOAc, 120 ℃, 24 h	PS	BA (58~89)	[30]
VO(acac)₂	O₂ (101 kPa), White LED, DCM, r.t., 1~7 d	PE/PP/ PS/PVC	FA (3.1~28.9); AA (20.7~35.5); BA (24.1~27.9); FA (82)	[32]
Mn₂O₃ aerogel	O₂, CO₂ (10 MPa), 135 ℃, 24 h	PP	AA (8); BA (2)	[27]
Mn(OAc)₂	O₂(1.5 MPa), NHPI, EA/AcOH (V∶V=2∶1), 150 ℃, 5 h	PS	BA (32~46); TA (7~11)	[38]
Co(NO₃)₂/Mn(NO₃)₂	O₂(0.2~0.4 MPa), NHPI, AcOH, 150 ℃, 12 h	PE/PS	BA (21~71); DA (22~39)	[34,35]
CoCl₂/MnSO₄	O₂(101 kPa)/air flow, HBr, ⁿBuOAc, 120 ℃, 1~3.5 d	PE/PP/PS	FA (41~77); AA (>100); BA (60~65); DA (5~26)	[21]
FeCl₂	CH₃(CH₂)₈N₃, DDQ, H₂O, TFA, 60 ℃, 5 h	PS	PhNH(CH₂)₈CH₃ (17)	[26]
FeCl₃	O₂(101 kPa)/air flow, 390 nm, acetone, TBACl, TCE, r.t., 5 d	PS	BA (54~67)	[28]
FeCl₂	O₂(101 kPa), 400 nm, DCE/MeCN or acetone, r.t., 20 h	PS	BA (56~67)	[29]
FeCl₂	O₂(101 kPa)/air flow, white LED, acetone, r.t., 20 h	PS	BA (2~16)	[31]
Fe(acac)₂	O₂(2 MPa), urea, ^tBuOH, 180 ℃, 24 h	PP	MeCN (5~18); MeCONH₂ (16~36); (Me)₂CO (13~15)	[22]
Fe(TPP)Cl, LiClO₄	O₂(101 kPa), undivided cell, 8 mA, DCM/ MeCN (V∶V=2∶1), AcOH, r.t., 24 h	PS	BA (6~11)	[36]
Fe(TPP)Cl, LiClO₄	O₂ (101 kPa), 390 nm, undivided cell, 4 mA, 1, 2-DCB/MeCN V∶V=2∶1), AcOH, r.t., 18 h	PS/PE/ PVC/PVDF	BA (38~56); FA (11~19)	[37]
CuBr	O₂(2 MPa), H₂O, MeCN, 200 ℃, 15 h	PS	PhCN (15~32); PhCONH₂ (26~42); PhCOOH (3~12)	[24]
(1) CuCl₂, CaCl₂; (2) Cu(NO₃)₂	(1) O₂ (101 kPa), Blue LED, MeCN/benzene, r.t., 72 h; (2) MeCN, 140 ℃, 24 h	PS	BA (46~65)	[40]
C₃N₄/MoS₂	Xe lamp, H₂O, r.t., 24 h	PE/PP	ROH (80); CO_x (3); RCOOH (17)	[41]
NiO/TiO₂	Air (1 MPa), H₂O, 200 ℃, 18 h	PS	PhCOOH (39~52)	[23]
NiO/CeO₂	(1) Air (2.5 MPa), NH₃(0.5 MPa), 220 ℃, 2 h; (2) N₂, 280 ℃, 4 h	PS	PhCN (43~53)	[42]

Catalyst	Conditions	Plastic	Product (Yield/%)	Ref.
PSA-1-TiO	O₂ (0.1 MPa), 370 nm, r.t., 4 h	PS	BA (18~40)	[33]
TS-1	Air (1.5 MPa), H₂O, 140~200 ℃, 12 h	PP/PE	Oil-DA (59~85)	[39]
VO(acac)₂/MBTB	PEG-400, 400~440 nm, NaOAc, 120 ℃, 24 h	PS	BA (58~89)	[30]
VO(acac)₂	O₂ (101 kPa), White LED, DCM, r.t., 1~7 d	PE/PP/ PS/PVC	FA (3.1~28.9); AA (20.7~35.5); BA (24.1~27.9); FA (82)	[32]
Mn₂O₃ aerogel	O₂, CO₂ (10 MPa), 135 ℃, 24 h	PP	AA (8); BA (2)	[27]
Mn(OAc)₂	O₂(1.5 MPa), NHPI, EA/AcOH (V∶V=2∶1), 150 ℃, 5 h	PS	BA (32~46); TA (7~11)	[38]
Co(NO₃)₂/Mn(NO₃)₂	O₂(0.2~0.4 MPa), NHPI, AcOH, 150 ℃, 12 h	PE/PS	BA (21~71); DA (22~39)	[34,35]
CoCl₂/MnSO₄	O₂(101 kPa)/air flow, HBr, ⁿBuOAc, 120 ℃, 1~3.5 d	PE/PP/PS	FA (41~77); AA (>100); BA (60~65); DA (5~26)	[21]
FeCl₂	CH₃(CH₂)₈N₃, DDQ, H₂O, TFA, 60 ℃, 5 h	PS	PhNH(CH₂)₈CH₃ (17)	[26]
FeCl₃	O₂(101 kPa)/air flow, 390 nm, acetone, TBACl, TCE, r.t., 5 d	PS	BA (54~67)	[28]
FeCl₂	O₂(101 kPa), 400 nm, DCE/MeCN or acetone, r.t., 20 h	PS	BA (56~67)	[29]
FeCl₂	O₂(101 kPa)/air flow, white LED, acetone, r.t., 20 h	PS	BA (2~16)	[31]
Fe(acac)₂	O₂(2 MPa), urea, ^tBuOH, 180 ℃, 24 h	PP	MeCN (5~18); MeCONH₂ (16~36); (Me)₂CO (13~15)	[22]
Fe(TPP)Cl, LiClO₄	O₂(101 kPa), undivided cell, 8 mA, DCM/ MeCN (V∶V=2∶1), AcOH, r.t., 24 h	PS	BA (6~11)	[36]
Fe(TPP)Cl, LiClO₄	O₂ (101 kPa), 390 nm, undivided cell, 4 mA, 1, 2-DCB/MeCN V∶V=2∶1), AcOH, r.t., 18 h	PS/PE/ PVC/PVDF	BA (38~56); FA (11~19)	[37]
CuBr	O₂(2 MPa), H₂O, MeCN, 200 ℃, 15 h	PS	PhCN (15~32); PhCONH₂ (26~42); PhCOOH (3~12)	[24]
(1) CuCl₂, CaCl₂; (2) Cu(NO₃)₂	(1) O₂ (101 kPa), Blue LED, MeCN/benzene, r.t., 72 h; (2) MeCN, 140 ℃, 24 h	PS	BA (46~65)	[40]
C₃N₄/MoS₂	Xe lamp, H₂O, r.t., 24 h	PE/PP	ROH (80); CO_x (3); RCOOH (17)	[41]
NiO/TiO₂	Air (1 MPa), H₂O, 200 ℃, 18 h	PS	PhCOOH (39~52)	[23]
NiO/CeO₂	(1) Air (2.5 MPa), NH₃(0.5 MPa), 220 ℃, 2 h; (2) N₂, 280 ℃, 4 h	PS	PhCN (43~53)	[42]

Table 1. Overview of earth-abundant metal-catalyzed oxidative degradation of polyolefins for efficient valorization

Scheme 2. TS-1 zeolite-catalyzed oxidative degradation of polyolefins of PS

Scheme 3. Proposed Ti-catalyzed pathway for the oxidative degradation of plastic

Entry	Plastic	Oil/PE feedstock
1	PP	59%
2	LLDPE	72%
3	LDPE	85%
4	HDPE/LDPE/LDPE/PP (V/V/V/V=1/1/1/1)	68%
5	SF Bag	82%
6	White Bag	61%

Table 2. TiO2 particles-catalyzed oxidative degradation

Scheme 4. V/MBTB-catalyzed thermal oxidative degradation of polyolefins under visible light

Scheme 5. VO(acac)2-catalyzed oxidative degradation of polyolefins under visible light.

Scheme 6. Proposed V-catalyzed pathway for the oxidative degradation of plastic waste.

Entry	Condition	Selectivity/%
Entry	Condition	FA	AA	PA	Acetone
1	O₂/PP (V∶V ≈ 1.5)	68	14	6	12
2	sc CO₂, O₂/PP (V∶V ≈ 1.5)	34	28	10	28
3	Mn₂O₃, O₂/PP (V∶V ≈ 1.5)	82	8	2	8

Table 3. Mn2O3 aerogel-catalyzed oxidative degradation of poly-olefins

Scheme 7. Proposed Mn-catalyzed pathway for the oxidative degradation of polypropylene.

Scheme 8. MnO2-catalyzed upcycling of polyolefins into nitrogenated chemicals

Scheme 9. Mn(OAc)2-catalyzed oxidative degradation of alkylated or acylated PS into nitrogenated chemicals

Scheme 10. Proposed Co/Mn-catalyzed pathway for the oxidative degradation of polyolefins.

Scheme 11. Co/Mn/NHPI-catalyzed oxidative degradation of polyolefins.

Scheme 12. Co/Mn/Br-catalyzed oxidative degradation of polyolefins

Scheme 13. FeCl2-catalyzed nitrogenative degradation of polystyrene

Scheme 14. Fe-catalyzed oxidative degradation of polystyrene plastics under visible light

Scheme 15. Possible mechanism proposed for polystyrene degradation with Fe/light system

Scheme 16. Fe-catalyzed thermal oxidative degradation of PP plastics

Scheme 17. Fe-electrocatalyzed oxidative degradation of polyolefins

Scheme 18. Proposed mechanism for Fe-porphyrin-mediated photoelectrocatalytic degradation of polystyrene.

Scheme 19. Cu-catalyzed nitrogenative degradation of polystyrene

Scheme 20. Proposed mechanism for Cu-catalyzed nitrogenative degradation of polystyrene

Scheme 21. Cu-catalyzed oxidative degradation of polystyrene under visible light

Entry	Catalyst	Plastic	Yield/%
Entry	Catalyst	Plastic	OH	COOH	CO_x
1	C₃N₄	PP		47.0	53.0
2	MoS₂/C₃N₄-20%	PP	67.6	21.3	11.1
3	MoS₂/C₃N₄-50%	PP	69.8	26.3	3.9
4	MoS₂/C₃N₄-100%	PP	80.3	17.1	2.6
5	C₃N₄	PE		27.2	72.8
6	MoS₂/C₃N₄-100%	PE	54.3	22.5	23.2

Table 4. Photocatalytic oxidative degradation of polyolefins with C3N4/MoS2

Scheme 22. Proposed mechanism for generation of reactive oxygen species under C3N4 and C3N4/MoS2 catalysis

Scheme 23. Ni-catalyzed oxidative degradation of polystyrene

Scheme 24. Ni-catalyzed oxidative degradation of polystyrene

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丰产金属催化的聚烯烃氧化降解研究进展

Recent Advances in Earth-Abundant Metal-Catalyzed Oxidative Degradation of Polyolefins

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