CO2/C2H4耦合制备丙烯酸及其衍生物的研究进展

doi:10.6023/cjoc202110040

摘要/Abstract

二氧化碳(CO₂)不仅仅是一种温室气体, 更是一种重要的、有效的碳一资源, 其来源丰富、无毒、无污染、不易燃烧, 可用于生产有机化学品、材料、糖类等. 由于CO₂分子中的碳处于最高氧化态, 且其分子具有热力学和动力学惰性, 因此人们不断探索新型反应途径, 以及新型的催化体系来有效资源化利用CO₂. 近年来, 利用各种不饱和烃类, 在过渡金属催化剂协助下催化CO₂与烯烃生成不饱和羧酸及其衍生物引起了极大关注. 其中, 催化CO₂/C₂H₄耦合反应制备丙烯酸及其衍生物因其原子经济性而备受瞩目. 以镍系催化体系为主的过渡金属催化CO₂/C₂H₄偶联反应是CO₂化学转化与高值利用非常重要的研究热点之一. 综述了近年来CO₂/C₂H₄偶联反应的最新进展, 对相应的催化反应机理进行了评述. 从多个角度对各位学者的研究进行分析比较, 并对各研究方向进行了展望.

关键词: 二氧化碳, 丙烯酸, 耦合反应, 反应机理

Carbon dioxide (CO₂) is not just a greenhouse gas, but also an important and effective one-carbon resource, which is abundant in nature and can be used to produce organic chemicals, materials, and sugars etc. CO₂ is thermodynamically and kinetically inert because the carbon atom in CO₂ molecule is in its highest oxidation state. In the past decades, several catalytic systems have been developed for the utilization of CO₂. The catalytic conversion of CO₂ to unsaturated carboxylic acids and their derivatives has attracted great attention. Among them, the so-called “dream reaction” of coupling CO₂/C₂H₄ is 100% atom efficient. Transition metal-based catalysts are developed for catalytic transformation of CO₂/C₂H₄ into acrylic acid and its derivatives, including Ni, Pd, Fe, and Ru etc. In addition, the additives play an important role in improving the catalyst performance. In this review, the recent advances on transition metal complex catalyzed CO₂/C₂H₄ coupling reaction are summarized on the basis of catalyst activity and reaction mechanisms, including both the experiment and theoretical calculation. Furthermore, the challenges and perspectives in the catalytic transformation of CO₂/C₂H₄ are also discussed.

Key words: carbon dioxide, acrylic acid, coupling reaction, reaction mechanism

引用此文

朱有财, 丁欣欣, 孙莉, 刘振. CO₂/C₂H₄耦合制备丙烯酸及其衍生物的研究进展[J]. 有机化学, 2022, 42(4): 965-977.

Youcai Zhu, Xinxin Ding, Li Sun, Zhen Liu. Advances in the Production of Acrylic Acid and Its Derivatives by CO₂/C₂H₄ Coupling[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 965-977.

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图/表 27

图式1. CO2/C2H4耦合形成五元环镍内酯的反应

Scheme 1. Formation of five-membered nickelalactone ring via CO2/C2H4 coupling

图式2. 五元环镍内酯的形成机理

Scheme 2. Formation mechanism of five-membered nickelalactone ring

图式3. 五元环镍内酯与含氮或膦配体的反应

Scheme 3. Reaction of five-membered nickelalactone ring with N- or P-containing ligands

图式4. CO2/C2H4耦合制备丙烯酸机理

Scheme 4. Mechanism of acrylic acid production by coupling CO2/C2H4

图式5. 丙烯酸还原消除的可能途径

Scheme 5. Possible pathways for reductive elimination of acrylic acid

图式6. 镍系催化剂的C—C耦合能垒(kJ/mol)

Scheme 6. C—C coupling barriers (kJ/mol) in the Ni-catalyzed reaction

图1. Ni(L)(ethylene)配合物的空间图(L=dmpe, dcpe, dtbpe)

Figure 1. Steric maps of the Ni(L)(ethylene) complex (L=dmpe, dcpe, dtbpe)

图式7. CO2/C2H4在碘甲烷作用下耦合制备丙烯酸甲酯机理

Scheme 7. Mechanism of methyl acrylate production by coupling CO2/C2H4 in the presence of methyl iodide

图2. CO2/C2H4在碘甲烷作用下耦合制备丙烯酸甲酯的吉布斯自由能(实线)和焓(虚线) (kJ/mol)

Figure 2. Gibbs free energy (solid line) and enthalpy (dashed line) for the preparation of methyl acrylate by coupling CO2/C2H4 in the presence of MeI (kJ/mol)

图3. 应用于Ni—O键断裂以及释放丙烯酸甲酯的甲基化试剂

Figure 3. Application of methylation reagents for Ni—O bond cleavage and release of methyl acrylate

图4. 溶剂对丙烯酸甲酯形成的影响

Figure 4. Effect of solvents on methyl acrylate formation

图式8. Ni—O键断裂的可能途径(kJ/mol)

Scheme 8. Possible pathways for Ni—O bond cleavage (kJ/mol)

图式9. CF3I诱导镍内酯开环的机制

Scheme 9. Proposed mechanism of CF3I-induced ring opening of nickelalactones

图式10. CO2/C2H4在碘化烷基作用下耦合制备丙烯酸酯机理

Scheme 10. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of alkyl iodides

Entry	Base	Additive	Time/h	Temp./℃	Yield/%
1	NaO^tBu	—	0.25	25	90
2	NaHMDS	—	0.25	25	87
3	NaOMe	—	24	50	51 (71)^a
4	NaOH	—	24	50	0 (70)^b
5	NaOPh	—	72	70	0
6	NBu₄OMe	—	72	50	0
7	NBu₄OMe	NaOAr_F	72	50	47
8	DBU	—	72	70	0
9	DBU	NaOAr_F	72	70	0
10	P1	—	72	50	0
11	P1	NaOAr_F	72	50	40

表1. 碱作用下[Ni{(CH2)2CO2}(dtbpe)]转化为[Ni(η2-CH2=CHCO2Na)(dtbpe)]

Table 1. Base-mediated transformation of [Ni{(CH2)2CO2}- (dtbpe)] into [Ni(η2-CH2=CHCO2Na)(dtbpe)]

图式11. CO2/C2H4在碱作用下耦合制备丙烯酸盐机理

Scheme 11. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of base

图式12. CO2/C2H4在LiI作用下耦合制备丙烯酸盐机理

Scheme 12. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of LiI

图式13. 碱作用下镍内酯的裂解

Scheme 13. Cleavage of nickelalactone under the action of base

图式14. CO2/C2H4在碱作用下耦合制备丙烯酸盐机理

Scheme 14. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of base

图式15. 大环二膦配体的制备

Scheme 15. Production of macrocyclic diphosphine ligands

图式16. CO2/C2H4在碱作用下耦合制备丙烯酸盐机理

Scheme 16. Mechanism of acrylate production by coupling CO2/C2H4 in the presence of base

图5. 新型双膦配体

Figure 5. Novel bisphosphine ligands

图式17. 丙烯酸酯在钯中心的释放

Scheme 17. The release of acrylates in the palladium center

图式18. CO2/C2H4在钯系催化剂作用下的耦合机理

Scheme 18. Coupling mechanism of CO2/C2H4 under the action of palladium-based catalyst

Entry^a	Ligand	TON^c	Pd leaching/(mg•L^–1)
1^b	none	0	n.d.^d
2	PCy₃	0	<1
3	dcpm	0	13
4	dcpe	106	1
5	dcpp	22	<1
6	dcpb	9	<1
7	dppe	0	<1
8	dmpe	0	49
9	dtbpe	17	14

表2. 不同配体条件下CO2/C2H4在碱基作用下直接制备丙烯酸盐

Table 2. Direct production of acrylates by CO2/C2H4 in the presence of bases under different ligand conditions

图式19. CO2/C2H4在钌系催化剂作用下的耦合机理

Scheme 19. Coupling mechanism of CO2/C2H4 under the action of Ruthenium-based catalyst

图式20. CO2/C2H4在铁系催化剂作用下的耦合机理

Scheme 20. Coupling mechanism of CO2/C2H4 under the action of iron-based catalyst

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CO₂/C₂H₄耦合制备丙烯酸及其衍生物的研究进展

Advances in the Production of Acrylic Acid and Its Derivatives by CO₂/C₂H₄ Coupling

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